The average tenure of a Chief Revenue Officer today is between 18 and 25 months. Harvard Business Review reports the CRO average at 25 months, among the shortest in the C-suite. Analysis of 14,000 executives by Pave puts the median at 1.8 years for both CROs and CMOs, with 32 percent annual turnover. Gong’s research on tech VP Sales tenure shows it has fallen from roughly 26 months to 19 months over a seven-year stretch. Compare that to CEOs at 4.3 years and CTOs at 3.7. Go-to-market leadership has the shortest tenure of any executive function in the company, by a wide margin.

The official explanation is that sales leaders miss their number. Technically true. And it’s almost never the actual reason.

The actual reason, and I’m quite opinionated on the topic, is that most companies are not built to support the work that produces revenue. They are built to support the work that looks like revenue is being produced. The gap between those two things is where every sales leader I have known, including the ones I respect most, has eventually run out of road.

What Companies Actually Measure

Walk into almost any B2B sales organization and look at what is on the dashboard.

Meetings booked. Opportunities created. Pipeline coverage ratio. Demos delivered. Outbound activity. MEDDIC or MEDDPICC fields populated. Stage progression velocity. Forecast call accuracy at the deal level. Weekly hygiene scores.

Every one of these is countable. Every one of these can be reviewed in a weekly pipeline meeting and produce the sense that real work is being done. Every one of these can be reported up to a board with a chart that trends in a direction. Not one of those, by itself, produces a closed deal.

What produces a closed deal is the buyer’s willingness to change.

That’s it. Nothing else. The moment when a senior person on the buyer’s side decides that the cost of staying where they are is higher than the cost of doing the work to move. Until that moment arrives, no demo, no proposal, no follow-up, no nurture sequence will move the deal forward. After that moment arrives, almost any execution will close it.

This is not new. Mike Bosworth named it in the 1990s. MEDDPICC literature calls poor pain discovery a massive hidden cost of B2B sales. A piece published on CustomerThink in late 2025 stated plainly that when sales teams are incentivized on activity, salespeople prioritize speed over understanding and rush through discovery to hit their activity targets. A clinical sales firm documented replacing “new meetings per month” with “new cross-functional contacts added per account,” watching pipeline volume shrink and close rate jump 30 percent.

The research has been clear for decades. But the behavior has not changed. And LinkedIn is full of influencers shilling out useless metrics and activities. Why?

Because Pain Discovery Is Uncomfortable

That’s it. Nothing else. Sitting with a prospect long enough to surface what they have not yet admitted to themselves requires the seller to do three things that human beings instinctively avoid.

Ask a question they do not already know the answer to.

Stay silent after the buyer gives any response.

Ask a harder follow-up that makes the cost of the buyer’s current situation real enough that the buyer feels it in the room.

Most sellers will not do this. They retreat to the demo. They retreat to the feature list. They retreat to the follow-up email. These are activities that can be completed without anyone feeling anything. They move the dashboard. They do not move the buyer.

And This Brings Me To The Sales Leader.

A sales leader who has not done the personal work to tolerate this discomfort cannot coach it. They cannot sit in a deal review and watch a rep fail to articulate the buyer’s pain without rescuing them. They cannot push back on the CRO or CEO when the request is “more activity” and the right answer is “deeper qualification.”

So they build the team they can manage. Which is the team that produces the activity dashboard. Which is the team that misses the number. Which is the team whose leader gets replaced in 18 to 25 months.

Three scenarios I have seen

Scenario one. The pipeline review.
A rep is walking the team through a deal in stage three. The economic buyer has not been in a meeting yet. The rep says “they’re really engaged” four times. The manager asks about next steps. The rep says a follow-up demo is scheduled for next Thursday with the original champion. The manager moves to the next deal. The deal stays in stage three for two more quarters. It eventually goes to closed-lost with the reason “no decision.”

What did not happen in that pipeline review. Nobody asked what the buyer was trying to accomplish in their own words, and what it was costing the buyer to not have it today. Nobody made the rep sit in the discomfort of not knowing. Nobody made the manager sit in the discomfort of a rep not knowing. The review rewarded motions and metrics. It did not reward depth.

Scenario two. The QBR with the board.
The CRO presents pipeline coverage at 4.2x. The board nods. Coverage is the headline. Nobody asks how many of those opportunities have a documented, quantified business pain attached to them. Nobody asks the win rate by depth-of-qualification. The CRO has been trained that 4.2x is the answer to the question. When the quarter closes at 60 percent of plan, the diagnosis is “execution issues at the rep level.” Six months later the CRO is gone. The next CRO inherits a 4.2x coverage ratio and the same conversion problem.

Scenario three. The hire who tried to slow it down.
A new VP of Sales joins. Within 90 days they propose narrowing the ICP, killing two-thirds of the pipeline, and rebuilding discovery to surface quantified pain before any deal advances past stage two. Pipeline volume drops 40 percent in the first quarter. The board asks questions. The CEO panics. The VP defends the methodology, points to early conversion improvements, asks to see the year through. They do not get it. They are replaced in Q3 by someone who promises to “rebuild pipeline aggressively.” Pipeline rebuilds. Conversion stays where it was. The cycle continues.

The Discomfort Problem

Most companies have a discomfort problem.

Asking about pain, and the impact of that pain on the buyer, their department, their career, and the overall business, is uncomfortable for the seller. Coaching to depth is uncomfortable for the manager. Forecasting fewer, deeper opportunities is uncomfortable for the CRO. Watching pipeline volume drop while conversion improves is uncomfortable for the CEO. Explaining to the board that quality is going up while quantity is going down is uncomfortable for everyone.

Activity is the escape. Activity lets every layer of the company seem productive without anyone having to feel anything. The price is paid in two places. Buyers do not change. And every 18 to 25 months, the sales leader gets replaced for failing to produce a result the company was never built to produce.

The leaders who break this cycle, the ones I have seen thrive and build revenue teams that hold up over time, have one thing in common. They are willing to be uncomfortable.

They will defend a smaller pipeline in a board meeting. They will let a rep struggle in a deal review. They will ask the buyer the question that makes the room go quiet. They will slow deals ready to sign, because when they win deals, they make sure the buyer actually changes. (Read “renewal”)

This is not a methodology. You cannot install it from a deck. It is a leadership posture. It starts with whether the person at the top can sit in the discomfort themselves, or whether they need the dashboard to tell them everything is fine.

In 30 years of various roles, I’ve gotten comfortable with one thing – discomfort. The teams that win are the ones whose leaders are comfortable with discomfort. Everything else is theater.

And yes, our teams have crushed quotas.
Just ask them.

The post Why Sales Leaders Keep Getting Replaced appeared first on Allen Adjamian.

I was in cold sweats, shaking, covered in hives. I could barely speak. I kept whispering the same two words into the phone in my hand. It’s over. It’s over. It’s over.

On the other end of the line, our Head of Infrastructure was on a three-way call with top-tier support at Dell and Citrix. Our cloud servers had crashed. We had lost mail and file data for clients. And then I learned the thing I was not prepared to hear. We didn’t have a backup. The people in charge of running them had not run them. The reports that should have surfaced this had not surfaced it. The odds of catastrophic failure were low, so the work of verifying had gotten passive across an entire chain of roles.

In that moment on the floor, I thought I knew what was falling apart. Fifteen years of my life’s work. The exit strategy I had been quietly building toward. The reputation I had built with every client. A future I thought I had earned.

I was wrong about what was falling apart. All those things survived the calamity. It took me years to understand why I had fallen apart as if the ground had opened up beneath me.

What I Told Myself

I told myself the story most CEOs would tell. The infrastructure team failed. The process failed. We will rebuild, we will install controls, we will never be here again.

That story was convenient. It located the problem outside of me. It also kept me from seeing what had actually happened.

The crash, however, was the result of the company culture I had built. I had bought the company. I had merged its people into mine. I had set the reporting lines, the responsibilities, the pace. I had hired the Head of Infrastructure. The people who reported up through that role, the ones who were supposed to run the backups and verify the reports. Everyone in the company had learned the same thing. The careful, detailed, unglamorous work was the kind of work nobody noticed when it got done and nobody enforced when it did not. I had assumed they would care about it the way I cared about it. They had not. They were not negligent in any outright way of their own reasoning. They simply did not bring to the work the level of attention that work required.

The crash was not a moment of negligence by one person. It was the natural result of a system of trust I had spent fifteen years building.

Why did I build it that way?

That is the question that took me years to ask.

The Belief

I named the company Alpha Actual. The name had two meanings.

In the military, when someone calls for help on the radio and the person who can actually make the decision and see the thing through answers, they say Houston Actual. The actual person. The one whose word can carry the action. Alpha is also a financial term for the active return an investment delivers, the performance above and beyond a benchmark. I used those words to convey that what you expected from us was what you got. The actual matched the alpha.

I did not consciously know I was naming the company after a belief. I do now.

I grew up in an environment I could not trust to keep me safe. What offered love also offered harm. Two truths sat in the same place, and I learned young that what people said had little to do with what they did.

The belief that formed in me, slowly, over years, was this. When I am older, I will build a world made of responsible adults. The people around me will be reliable in a way the adults of my childhood were not. The promise and delivery will be the same thing.

I do not want to be cute about that. An eight-year-old who concludes that the adults around him cannot be trusted, and decides he will one day build his own world made of people who can be trusted, is doing survival work. The belief that took root was not a character flaw. It was my lifeline.

The company name was that belief stated to the world. I hired with the belief. I trained the company on it. I rewarded people who held it. And when people fell short of it, I took it personally, because the belief was personal. Much of my life played out the way it did because of my childhood experiences that had remained blind to me and unprocessed.

Therapists call it repetition compulsion.

If the people you hire are responsible adults, you should not need to check on every little thing. You should not have to doubt their word or reports. You should not need to verify the verifiers. The whole point of the belief is that you should not have to live the way you lived as a child, watching every little thing because you could not trust anyone.

So I trusted. And the company succeeded and fell apart by way of it. There were not enough checks on the people verifying backups because the belief did not let me see the need for them. Building them would have meant admitting the adults I had hired could not be trusted to be responsible and accountable, which would have meant admitting the belief itself could not hold. I could not admit that consciously then. I had organized my life around it.

The crash was my belief clashing against reality. A negative alpha of catastrophic proportions, actualized. As everyone knows, reality always wins.

How Beliefs Work

A belief taking hold in childhood does not just announce itself. It does not speak in the language of belief. It speaks in the language of what is obvious, what is logical, what any reasonable person would do. By the time you are an adult, the belief is not a belief to you. It is your reality, the way you see the world.

Depth psychology has a word for the part of the psyche that holds these unexamined operating principles. It calls them complexes. They are not pathologies. They are what we built to survive what we could not yet understand. And they keep running, long after the conditions that produced them have changed. The eight-year-old who concocted the belief does not get the news that you are thirty-five now and running a multi-million dollar company. He is still in the bedroom, curled up, trying to survive. That work of survival is just the wrong work for the life you are now living.

There is a line in the Tao Te Ching: To grasp is to lose. When I first read it, I understood it as a metaphor. I read it the way founders read wisdom literature, looking for a tactic. Be less attached to outcomes. Hold things lightly. Don’t micromanage.

That is not what it means.

What it means is that the hand trying to hold the world cannot do anything else with itself. It cannot receive. It cannot build. It can only grip. And the gripping produces the loss. Not because the universe punishes control.

Because a closed hand has stopped participating in what makes anything grow.

The grip of that belief was also the thing I was least able to see, because it felt like competence. It felt like leadership. It felt like the reason we were succeeding at all!

But the belief that keeps you safe is almost always the belief that keeps you small.

What I See Now

I have done decades of inner work through a Jungian lens. I now spend my time in coaching conversations with founders and executives. I see their beliefs now.

They built companies on beliefs they cannot see. The beliefs show up in everything: the hiring, the org chart, the culture, the products, the strategy. The companies are now showing many of them the limits of their beliefs, and they are confused about what is happening. The way I was confused for a long time.

I sit with founders who are running on hidden childhood beliefs, and I witness them slowly take notice.

Noticing is the work.

Our beliefs don’t fall away just because we notice them. But they do stop running us in the dark.

More Than A Decade Later

It has been more than a decade since I sold the company, which is its own story. The belief is still in me. It will be there until I die. That is not pessimism. That is honesty about a belief installed at eight and reinforced for forty years.

What has changed, however, is my relationship to it.

I can feel it now, when it is active. I can feel the pull to expect more responsibility from someone than they can give, and to register the gap as their character flaw rather than human nature. I can feel the impulse to lash out when an adult around me is not what the belief says they should be. I can hold the impulse now, instead of being run by it. I can sit in the tension between that belief and the nature of reality. I can ask whether the situation in front of me is reality, or whether the eight-year-old is looking at it.

Most of the time I can tell the difference. Sometimes I still cannot. My work is not to eliminate the belief. The work is to meet the child who built it, to thank him for helping me survive, and to let him know that the world he has prepared me for is not the world I am actually living in. The adults around me now are not the adults of his childhood. Or they are. It no longer matters. He does not have to keep watching for them as I now know how to watch over and take care of him.

He does not always believe me. I keep telling him and showing him anyway.

That is what I mean when I talk about transformation. A different relationship with the beliefs that took root before you had any say in the matter. The beliefs stay. Their grip on you loosens. The world becomes a place you are living in, instead of a place trying to match a child’s expectations from a long time ago.

Whatever is in front of you right now may also probably not be the thing. That thing may be older. And underneath. And the work, when you feel called to it, is not to fix what you see. It is to meet the part of you that needed the world to be different than it is, and to introduce that part to the life you have actually built, which is more than enough, and which has been waiting for you to arrive in it, for a long time.

The Thing Beneath the Thing: Questions Founders Ask Me

What does “the thing is never the thing” mean?

The crisis in front of you is rarely the real one. When my company’s servers crashed with no backups, I thought I was losing fifteen years of work. What had actually failed was a belief I had built the whole company on. The surface problem is usually the visible edge of something older and underneath.

Why do the same problems keep happening in my company?

Because a company quietly takes the shape of its founder’s beliefs, including the ones you cannot see. The hiring, the org chart, the culture, all of it carries them. When the same pattern keeps returning across teams and years, it is usually pointing at something in you, not bad luck.

How do childhood beliefs shape how someone leads?

More than we like to admit. I built a company around a belief formed at eight, that I would surround myself with people reliable in a way the adults of my childhood were not. It worked until it didn’t. These beliefs do not feel like beliefs. They feel like plain reality, which is exactly why they run us unseen.

Can you get rid of a limiting belief?

In my experience, no. The belief installed in childhood stays. What changes is your relationship to it. I can feel mine now when it is active, and hold it instead of being run by it. That shift, from being run by a belief to being able to see it, is the real work.

What does transformation actually mean in coaching?

Not fixing the problem in front of you. It is meeting the part of you that needed the world to be different than it is, and slowly loosening its grip. The belief may stay, but it stops running you in the dark, and your life becomes something you live in rather than something braced against an old fear.

On why the same problems keep returning until the deeper layer changes: Identity-Level Coaching for Founders.

The post The Thing Is Never The Thing appeared first on Allen Adjamian.

At first, I didn’t want to say anything. I played it off with platitudes and a bunch of “meh, you’ll be fiiinne”. I am often asked for advice, yet I have a long-standing reluctance about giving advice. I’ll spend most of this post explaining why. But this was my friend. Someone I love and care for. And his fear was so raw, so present on his face that I saw him like I see my own son, and my reluctance gave way. I told him to lean in. To stop managing the situation from a safe distance and instead be fully present in it — authentic, vulnerable, speak this truth gently but remain boundaried. I gave him my observation, which I preceded with the fact that I am looking from the outside and I can’t truly diagnose the situation, but I told him to sit with the uncertainty and stay in for as long as he could. How long, he asked. Give it time, six months I proffered. I believed, and still believe, that this was the right orientation for a person struggling with what he was going through.

What happened next slapped me in the face like a bag of bricks.

Over the following days, something shifted in him. Not towards patching up this pillar of his life. Toward clarity. The man who had come to me terrified of losing this amazing thing he had built, decided to unravel it himself. He went from gripping the pillar with both hands to letting it go. Completely.

I still don’t know what to make of it. I’m not sure it was wrong. I’m not sure it was right. What I know is that I watched my own advice travel through another person’s life and arrive somewhere I never anticipated, carrying weight I didn’t intend, touching parts of him I couldn’t see.

That’s the thing about advice. It never stays the shape you gave it.

Why People Ask

Before we talk about what happens when advice lands, it’s worth sitting with why people seek it in the first place.

The simple answer we like to go to is that people want guidance. They’re facing something hard, they don’t know what to do, and they hope someone else does. But I’ve come to believe that’s rarely the full picture. It’s the lie believed to preserve the hidden truth.

When someone asks for advice, they are almost always also asking to be relieved of something — the weight of not knowing, the discomfort of sitting with an open question, the anxiety of genuine uncertainty.

Advice feels like solid ground. A path paved by someone else can be stood on, at least for a moment, without the whole body shaking.

The psychologist Erich Fromm called this the “escape from freedom.” His insight was that genuine freedom (the freedom to choose, to author your own life) is experienced by most people not as liberation but as burden. It produces isolation and anxiety. And one of the most reliable ways to escape that anxiety is to hand your path forward over to someone else. An authority, an expert, a wise friend with a beard.

This is not weakness. It’s deeply human. But it means that the moment someone asks you for advice, they are often not really asking you to solve their problem. They are asking you to take the weight of their uncertainty off them, even briefly. And if you take it, if you give the advice, you have done something to them that neither of you fully recognizes. You’ve made their path yours. And however that path goes, some part of you will carry that. Not because it’s your fault. But because you made it your business.

The Invisible Lens: Projection

Carl Jung gave us a word for something that happens constantly in human relationships, mostly without anyone noticing: projection.

In simple terms, projection is the unconscious act of placing something from inside yourself onto someone outside.

In projecting, you attribute to another person a quality, a feeling, or a capacity that is actually a reflection of your own inner world.

We all do it. It’s not pathology. It’s the method of how the psyche manages what it cannot yet hold consciously.

When someone projects wisdom onto you, the mechanics are roughly this: they encounter something in you (your history, your willingness to sit with hard questions, your stature) that resonates with a quality they sense but haven’t fully claimed in themselves. Something in them knows their path. But they haven’t yet trusted that knowing. So they place it outside themselves. They put it on you. And then they ask you for it back.

“Everything that irritates us about others can lead us to an understanding of ourselves.” — C.G. Jung

The reverse is equally true: everything we idealize in others, the wisdom, the clarity, the groundedness we seek, is often a quality we are not yet willing to own in ourselves.

This is why people in my circles tend to come to me for advice. I don’t think it’s because I’m wiser than they are. It’s because something in the way I engage (the questions I ask, the pace I keep, the willingness to name hard things directly) reflects back a quality they are reaching toward. They project onto me a certainty I do not possess. And then they ask me to hand it back to them.

The trouble is: when you accept the projection, when you play the wise, bearded elder, you don’t give them the thing they actually need. You deprive them of it.

Because the thing they actually need is to find their way to their own knowing. To stop borrowing clarity from someone else’s face and find it in their own.

Advice, received through the lens of projection, almost never does what it appears to do. It doesn’t transfer wisdom. It confirms the receiver’s belief that the wisdom lives somewhere outside them. And that belief is the very thing keeping them stuck. And that’s a wild, wild thing to say and to see. And yet, that’s exactly why people go to motivational seminars and listen to the amazing Tony Robbins tell them they can do it! So they can package that feeling from their projection, handed back neatly by Tony, for them to carry into their lives for a little bit and then go right back to where they were before, and then repeat the cycle the next time his circus is back in town.

The Shape of Uncertainty

There is an old story from the Taoist tradition that I find myself returning to often. It goes something like this:

An old farmer’s horse ran away. His neighbors came to console him. “Such bad luck,” they said. The farmer replied: “We will see.”

The next morning, the horse returned, and with it came a dozen wild horses. The neighbors rushed back: “What wonderful luck!” The farmer said: “We will see.”

That afternoon, the farmer’s son tried to tame one of the wild horses and was thrown. He broke his leg. “Such terrible luck,” said the neighbors. “We will see,” said the farmer.

The following week, soldiers came through the village to conscript young men for war. The farmer’s son, with his broken leg, was spared. “How fortunate,” the neighbors said. The farmer said: “We will see.”

What makes this story worth reading again and again is not the twist. It’s the farmer’s refusal to give-in to the uncertainty prematurely. He doesn’t know if things are good or bad. Not because he’s passive or detached, but because he understands that life unfolds across a longer horizon than any single moment can reveal. The neighbors, always certain, do not sway the farmer’s resolve to stay in uncertainty.

I’m living my own version of this right now. My son is five. We’ve applied to six private schools — the kind where if he gets in, he’ll likely be there from kindergarten through twelfth grade. All six give their answers on the same day. Our first choice feels like the right fit, the porridge is just right – it’s got a little bit of everything we value. And it’s the closest drive for daddy and daddy cares a lot about that. The others are all genuinely great — one has a campus built for athletics, one is academically intense, one is deeply rooted in community and diversity. We want what’s right for him. We just don’t know what right looks like yet. And here’s what I keep coming back to: even if we get our first pick, I still won’t know. His life will unfold the way it will unfold, shaped by teachers and friendships and moments I can’t anticipate, inside whatever walls he ends up in. The school we’re hoping for might be exactly right. It might be the thing that costs him something we can’t currently see. So, we will see.

My friend pulling apart his own pillar in life might be the worst thing that ever happened to him and everyone involved. It might be the moment that saves a life. It might bring people closer, it might pull people apart. I genuinely do not know. I have my own strong feelings and I’m contending with it. But I have stopped pretending to myself, that the advice I gave was right or wrong. It moved through him and became something altogether unrecognizable to either of us from that moment we shared. That’s all I know.

This is not a comfortable place to stand. But I think it’s an honest one.

Why Advice is Two Cents

I’ve arrived, through years of reflection on my experiences with adversity and loss, at a position that life advice has very little value. I work hard to give very little of it and I seldom ask anyone for it.

This isn’t false modesty. It’s not that I think I have nothing to offer. It’s that I’ve watched advice, my own and others’, move through people’s lives and consistently land somewhere other than intended. The problem isn’t the person giving it, but rather the very nature of advice.

First: advice is always drawn from someone else’s life. When I tell you what I would do, I am telling you what I, with my history, my wounds, my particular relationship to risk and loss and love, would do. That person is not you. The advice that saved me might undo you, not because it’s wrong in the abstract, but because it was built for a different soul.

Second: advice, by its nature, skips the most important part. The most important part is not the answer. It’s the process of arriving at the answer — the sitting with uncertainty that the rockstar Jungian analyst, Marion Woodman, described as “holding an inner or outer conflict quietly instead of attempting to resolve it quickly.” The slow and uncomfortable clarification of what you actually value takes time. When someone gives you their answer, they rob you of that priceless process. You get the destination without the journey, and the journey was the thing that would have transformed you into who you sought to be all along.

Third: as we’ve already seen, advice passes through the distorting lens of projection. The person receiving it is not hearing what you said. They’re hearing it through who they believe you to be, which is mostly a fiction their own psyche constructed. We don’t see things as they are. We see them as we are. So the advice gets filtered, magnified, twisted. It arrives in a different shape than you sent it.

“I would like to beg you, dear Sir, as well as I can, to have patience with everything unresolved in your heart and to try to love the questions themselves as if they were locked rooms or books written in a very foreign language.” — Rainer Maria Rilke

He was saying, with great care, that the answer is not the point. Learning to live with the question is.

The Advisor Question

I want to draw a distinction here, because I think it matters.

There is a real and legitimate role for advisors, and it’s worth being precise about what that role is and where its limits are.

A good advisor is someone with deep expertise in a specific domain: M&A Finance, contract litigation, SaaS product strategy, consumer electronics go-to-market, cloud security architecture. When you bring an advisor into your orbit, you’re not asking them to weigh in on who you are or what your life should look like. You’re asking them to apply a concentrated body of knowledge to a well-defined problem. That should be genuinely useful. The best advisors I’ve known are extraordinarily disciplined about the limits of their expertise. They know what they know and they know where it ends and to say so.

But I watch founders reach for advisors — and mentors, and investors, and friends like me — for questions that are not domain specific to their tenured skillset. They’re sitting with something that doesn’t have a right answer. Something about whether to push forward or let go, whether a relationship has run its course, whether the company they built still fits the person they’ve become. They ask for advice on these questions because the questions feel unbearable, and because having someone else weigh in makes the unbearable feel momentarily more manageable.

No advisor can help with these questions. Not because advisors aren’t smart. Many of them are extraordinarily smart. But because these questions are not information problems. They’re not solved by more data or a better framework. They live in territory that expertise cannot reach.

This is where the advisor role ends and something else begins.

The Mirror

I became a coach not despite my reluctance to give advice, but because of it.

I have spent years sitting with people in the hardest moments of their work and their lives. Founders who built something real and then felt it slowly hollowing them out, myself included. CEOs who couldn’t understand why they kept recreating the same conflicts with different people, myself included. Leaders who had every external marker of success and felt, underneath, like they were running from something they couldn’t name, myself included.

What I noticed, repeatedly, was that these people (myself included) didn’t need other peoples’ answers.

They needed to see themselves more clearly.

They needed someone to hold up a mirror, not a flattering one, not a cruel one, but an honest one, so they could see the patterns they were living inside, the beliefs they were defending without knowing it, the story they’d been telling about themselves that had stopped being true.

That’s what coaching, at its best, is. Not advice. Not answers. Not even guidance in the conventional sense. It’s a particular quality of attention, rigorous, unhurried, willing to sit with what’s difficult, that allows another person to see what they couldn’t see alone.

Jung understood this. His whole psychology was built around the idea that what we cannot see in ourselves does not disappear. It reappears in our life, in the form of the circumstances we keep recreating, the relationships we keep damaging, the patterns we swear we’ve broken that keep returning – and of course, of course, it greatly impacts our careers. The work of becoming more conscious, more aware of what’s actually driving you, is not intellectual work. You can’t think your way to it. You need a relationship, a genuine encounter with another person, to bring the full you into clear view in the form of a mirror.

The Tao Te Ching puts it differently, and perhaps more simply:

“To the mind that is still, the whole universe surrenders.”

The coach’s job is not to speak wisdom into the room. It is to create enough stillness, enough safety, enough honest presence, that what the client already knows can surface. Most people are so busy managing their own anxiety, keeping up appearances, seeking validation, running from uncertainty, that they never get quiet enough for their deeper knowing to be heard.

The coach doesn’t give you anything you don’t already have. The coach helps you hear yourself.

What Changes, and How

I want to be specific about this, because I think it’s misunderstood.

When people imagine coaching, they often imagine something like a sophisticated version of advice: a smart person helping you think through decisions, offering frameworks, asking good questions that lead somewhere the coach already sees. And perhaps some coaching is like that – it’s a free market. That’s not the intent of my coaching work.

The kind of coaching I’m drawn to, and the kind I practice, goes to a different layer. It starts from the premise that the struggles leaders bring to coaching are rarely what they appear to be on the surface. The co-founder conflict is rarely just a conflict about decisions. The burnout is rarely just exhaustion. The inability to delegate is rarely just a management problem. These are the outer expressions of something happening at the level of identity — who the person believes themselves to be, what they believe they deserve, what they’re afraid to want, what they’re using the company to prove.

Working at that layer is slower. It asks more of the person. There are sessions that feel like nothing happened, and then something shifts weeks later in a conversation with a board member, co-founder, or a spouse and the person can’t explain why. The changes are not always traceable. But they tend to last, because they’re rooted in something real and the person goes through a transformation.

I’ve watched founders stop recreating the same conflict with different people, myself included. I’ve watched CEOs release a grip on control that had been slowly strangling their companies for years, not because someone told them to delegate, but because they’d done enough inner work that the compulsion to hold everything simply loosened, myself included. I’ve watched people whose companies were performing well finally let themselves feel it, instead of moving immediately to the next threat – myself included.

These are not small things. They’re the things that change how a person leads, how they love, how they inhabit their own life.

One Last Note on Advice

I still don’t know if what I told my friend was right.

I’ve turned it over many times. I’ve looked at the advice itself, lean in, be authentic, speak truth, be gentle but boundaried, and I believe those things. I still believe them. But I also know that my belief in them, and my love for him, and my reading of his situation, were all limited by who I am and what I can see from where I stood. He took what I said and carried it into his own interior, where it mixed with everything I couldn’t see, and arrived somewhere I didn’t expect.

Like the farmer, I will see, over time, what happened in my friend’s life and whether the path he’s on is one he can build something good from. So will he. And we will see what happens with my dear son, as we soon accept some school as our second home for the next thirteen years. Nobody knows yet.

What I do know is that the most useful thing I can offer, to my friend, to the founders I work with, to anyone sitting with something genuinely hard, is not my answer. It’s my presence. My willingness to sit with them in the not-knowing. My refusal to hand them a certainty I don’t possess.

That willingness is a different kind of help. It’s slower, and less satisfying in the moment, and it doesn’t let either person off the hook. But it points toward the place where real change actually lives: inside the person asking the question.

Further Reading

Memories, Dreams, Reflections – C.G. Jung

Letters to a Young Poet – Rainer Maria Rilke

Holding the Tension of the Opposites – Marion Woodman

Escape from Freedom – Erich Fromm

Tao Te Chin – Lao Tzu

On Advice: Questions Founders Ask Me

Why don’t you give advice?

Because I have watched advice, my own included, travel through someone’s life and land somewhere I never intended. It is always drawn from my history, not theirs, and it skips the part that actually changes a person: the slow work of arriving at their own answer. I would rather help you find yours.

Why do people really ask for advice?

Rarely just for guidance. Usually they are asking to be relieved of the weight of not knowing, the discomfort of an open question. Advice feels like solid ground to stand on for a moment. But handing your path to someone else, however wise, keeps the knowing outside you, which is the very thing keeping you stuck.

Why doesn’t advice work?

Three reasons. It is built for the giver’s life, not yours. It robs you of the process of arriving at the answer, which was the part that would have changed you. And it gets filtered through how you see the person giving it, so it arrives in a different shape than it was sent.

What is the difference between advice and coaching?

Advice hands you an answer. Coaching holds up an honest mirror so you can see the patterns and beliefs you are living inside, and hear what you already know. The coach does not give you anything you do not have. They help you get quiet enough to hear yourself.

How do you make a decision when you cannot know the right answer?

You learn to hold the question instead of rushing to resolve it. There is a Taoist farmer who meets every turn with ‘we will see,’ because life unfolds over a longer horizon than any moment reveals. The work is not forcing certainty. It is staying honest and present inside the not-knowing.

More on why I do not lead with advice, and what coaching does instead: What Is a CEO Coach?.

The post Notes on Advice appeared first on Allen Adjamian.

Most founders I work with don’t lack support. They lack the right kind of support for what they’re actually going through.

They have advisors giving them playbooks. Friends telling them they’re crushing it. Board members asking for updates. Maybe a mentor they grab lunch with once a quarter. And yet, something isn’t moving. The same patterns keep showing up. The same friction. The same quiet weight that no amount of tactical advice seems to touch.

The issue is rarely a lack of help. It’s a mismatch between the kind of help they’re receiving and the kind of problem they’re facing.

I learned this the hard way over three decades of entrepreneurship. I spent years leaning on the wrong type of support for what I was actually dealing with — and the cost was measured not just in dollars but in years I can’t get back.I’ve written about that reckoning before, and it’s something I come across often in the entrepreneurial community.

The terms mentor, advisor, and coach get used interchangeably. They shouldn’t. Each serves a fundamentally different purpose, and knowing the difference can save you years of spinning your wheels with the wrong person in your corner.

Mentors Tell You What They Did

A mentor is typically an accomplished professional some steps ahead of you on a similar path. They’ve been where you are. They can help you see around corners, warn you about potholes, and offer the reassurance that what you’re feeling is normal.

The value of a great mentor is their business pattern recognition. They draw from lived experience and can say, “Here’s what I saw when we faced something similar.” When you know you have a specific, identifiable challenge — stalling in your target market, navigating a specific board scenario, structuring a fundraise with a specific VC — a mentor who has already walked that road can be quite helpful.

But mentorship has structural limits. It tends to be informal and unstructured, which works well when you know what you’re dealing with. It breaks down when the problem is something you can’t yet name — or when the issue isn’t strategic at all, but deeply personal. And mentors, with the best of intentions, can fall into a trap of assuming that what worked for them will work for you. Different era, different market, different person. The principles may translate. The playbook often doesn’t.

Advisors Tell You What You Should Do

Advisors are subject-matter experts. They operate in a specific domain — sales, product, finance, legal, go-to-market — and they bring deep, narrow expertise to a clearly defined problem. When you know the domain of your problem, a good advisor will get you to a tactical solution faster than anyone else. Fast answers. Laser focus. Over the course of my career, I built a bench of advisors for exactly this reason and have served as an advisor when it comes to revenue.

Where advisory falls short is when the real problem isn’t in the domain at all or is far more encompassing. Sometimes what looks like a sales problem is actually a leadership problem. What looks like a hiring gap is actually a boundaries problem. What looks like a strategy issue is actually an identity issue. Advisors have a hammer, and they’re excellent at finding nails — but they can miss the structural cracks in the foundation.

I’ve lived this. I once spent considerable capital hiring expensive talent on advisor recommendations to solve what appeared to be a capacity problem. The numbers supported it. The logic was sound. But the real issue was something no advisor was equipped to see — it was a human problem hiding beneath the org chart. I wrote about this in detail because the lesson cost millions, and it’s one I never want another founder to learn the hard way.

Coaches Help You Grow So You Connect To Your Wisdom Within

A coach — a good one — doesn’t tell you what to do. They help you see what you cannot see on your own. They work at the level beneath behavior, surfacing the assumptions, identities, and emotional patterns that quietly, but powerfully, govern your decisions.

Where a mentor shares their experience and an advisor shares their expertise, a coach holds up a mirror.

They ask questions that no one in your orbit would think to ask — questions that bypass the business problem and go straight to the human pattern driving it.

Founders don’t walk around saying, “I’m living out my unexamined childhood survival strategy.” They say things like, “It’s faster if I just do it myself” or “My team isn’t ready for more responsibility.” or “We aren’t ready for a sales leader yet.” Those sentences sound rational. Underneath them is something far more primal: a story about who you must be in order to feel safe, valued, or in control. That invisible architecture is where your years disappear — and it’s precisely what coaching is designed to make visible.

The results of good coaching show up in the business, but they originate in the leader. Decisions that once felt paralyzing become doable. Conversations that once felt dangerous become clarifying. Patterns that repeated for years — sometimes decades — finally break. In my own journey, a coach asked me questions that fundamentally changed how I structured my company, my team, and my life. No mentor or advisor would have gone there, because no mentor or advisor was trained to see what was operating beneath the surface.

Where coaching shines: When the real issue isn’t what’s happening in the business, but what’s happening in the leader. When the same patterns keep repeating across different teams, different quarters, different companies. When you suspect the ceiling on the company is actually a ceiling inside you. That may look like you’ve got all the right people in the company but the company just isn’t firing on all cylinders. Coaching works at the root, not the symptom.

Where it demands caution: Anyone can call themselves a coach these days, which makes finding a great one challenging. Low-quality coaching might feel good in the moment, but it can delay you from meaningful growth. A great coach has a clear theory of change, does deep work, and is along for your transformation – one that you can feel in your life and in your business. If it doesn’t change how you lead under pressure, it isn’t working.

So Which Do You Need?

Probably more than one, at different times.

When I look back at my own three-decade journey, the honest answer is that I needed all three — and the cost of not knowing the difference cost me years.

Here’s a simple frame:

You need a mentor when you’re facing a challenge someone else has already navigated and you want to hear how they navigated their terrain. The value is in their experience. In sharing their past experience, you may find a way forward for yourself.

You need an advisor when you have a domain-specific problem that requires specialized expertise. The value is in their knowledge. A great advisor will provide a solution to your specific challenge in the moment so you don’t have to spend more time pondering options. Adopt it, move on.

You need a coach when the barrier to strategic progress is something within — a pattern, a belief, an identity — that you can’t see clearly from the inside. The value is in their ability to reveal what’s been invisible and work with you to become who you need to become to make your future vision a reality.

The deepest work — the kind that changes not just what you achieve but who you become — that’s coaching territory. Mentors and advisors tend to the branches. But if the roots are not well nourished, no amount of pruning will save the tree.

If any of this resonates with where you are in your journey, I’d welcome getting to know you.

Mentor, Advisor, or Coach: Questions Founders Ask Me

What is the difference between a mentor, an advisor, and a coach?

A mentor tells you what they did, drawing on a road they have walked. An advisor tells you what to do in their domain, fast. A coach does neither. They hold up a mirror and ask the questions that surface what you cannot see in yourself. Most founders need all three at different moments.

Do I need a coach or a mentor?

It depends on the problem. If you are facing something a peer has already navigated, you want a mentor’s experience. If the barrier is something inside you, a pattern or belief you cannot see from where you stand, that is coaching. The clue is when the same friction keeps returning no matter the advice.

What does a coach do that a mentor or advisor cannot?

Mentors share experience, advisors share expertise, and both work on the business in front of you. A coach works on the leader underneath it. The same patterns repeating across teams and quarters usually mean the ceiling on the company is a ceiling inside you. That is the ground only coaching reaches.

How do I know if I need a coach?

When you have the right people and the company still is not firing on all cylinders. When the same conversation keeps feeling dangerous and the same decision keeps feeling impossible. When you suspect what is holding the business back is something in you. That suspicion is usually right, and it is exactly where we would start.

How do I find a good executive coach?

Carefully. Anyone can call themselves a coach now, and the weak kind feels good in the moment while quietly costing you time. Look for a clear theory of change, real depth, and someone in it for your transformation. The test is simple: if it does not change how you lead under pressure, it is not working.

More on what a coach actually is, and what separates one from a mentor or advisor: What Is a CEO Coach?.

The post Do You Need a Mentor, an Advisor, or a Coach? appeared first on Allen Adjamian.

My co-founder was the quintessential “Servant Leader”—genial, calm, tireless, and always the first to jump into the trenches. He believed he was building a high-trust, flat culture. I watched as he eroded his own sovereignty, allowing the normalized audacity of his team to treat him as a safety net rather than operationalizing our vision at scale.

And I let it happen because it was convenient for me.

This didn’t make me a passive bystander; it made me an accomplice. My clean hands were actually a form of negligence. I was so focused on protecting my own comfort that I kept quiet on the fact that my trusted partner – a man I genuinely liked – was setting the building on fire with his heroism.

At some point, I knew my options. As majority shareholder, I could:

Fire him.
Demote him.
Hire more under him.

I wanted to avoid the conflict of the first two, so we kept hiring.

In failing to make the decision I knew I should have made, I did a massive disservice to the company. I should have fired him and replaced him with someone who could rebuild the team. But in my role driving revenue, I was “crushing it”—having fun, making friends, being interviewed—and I didn’t want to pivot into such a crucial, painful conversation.

The Costs of Avoiding Confrontation

Because I chose personal comfort over conflict, the rot in the organization didn’t just stay static; it metastasized. My decision to hire more under him was the exact moment the business model broke. I threw capital at a structural problem, increasing the velocity of our dysfunction. The results were devastating.

A Culture of Learned Helplessness

By hiring expensive talent under a “Hero,” we added to his work. Because my co-founder couldn’t set a boundary, he couldn’t delegate. The new hires quickly realized that they didn’t actually have to deliver excellence—they just had to cry for help and have it escalated to him. We were paying top salaries for people to watch my co-founder burn himself out.

This sent a silent but lethal message: “I don’t actually trust you to handle this.” The result wasn’t a supported or empowered team; it was a culture of learned helplessness.

The Skill Gap: Engineers stopped learning how to solve complex problems because they knew the boss would swoop in and do it for them. They got stuck in their skillsets and delayed their own promotions and career advancements. That later brewed resentment that showed up with sudden departures, sabotaged work, or simply checked-out employees.

The Ownership Void: Work was no longer seen through to the end; it was merely “started” and then “escalated” for the boss to finish. The team wasn’t owning their work; they were merely funneling the hard labor off to the equity holder.

The Hostility Pivot: As the stakes grew, the “high-trust” culture soured. Because no one was truly responsible for their own results, “dropping the ball” became the norm. They had the normalized audacity to say “Well, he wasn’t around to help us, he is always too busy.”

Writing this I just remembered how we had a long list of items under a ridiculous status “Waiting for Executive”.

Revenue Subsidized Risk

This is where my culpability cuts the deepest. Because I was crushing it on revenue, I masked the operational bleeding and increasing risk.

Every big deal I closed bought us more time to ignore the broken machine. My success created a false sense of security. I looked at the P&L and saw growth; I downplayed the spiraling risk of catastrophe of having reduced competency down to one person.

My poor boundaries around conflict avoidance blinded me. I told myself this chaos “was just part of being a successful startup.” Even though by any metric, we should have been operating like a mature organization. Revenue growth served as justification for my silence.

The Cost of Lost Clients

Eventually, the bill came due. Client deliveries began to miss their marks—massive, high-six-figure misses. Then catastrophe struck. Major outage – 100% caused by the environment we had allowed to take shape.

Millions lost overnight.

The genial atmosphere evaporated, replaced by defensive finger-pointing. Since the co-founder had touched every project, he took the blame for every failure. It was the antithesis of what I had envisioned. We lost years of sales efforts in a week, all because our COO was unable to focus on his role, and because I had allowed it to continue.

All this was a painful lesson more than a decade ago, but one I’ll never forget:

Leaders with poor boundaries are bottlenecks who prevent their people from growing up.

The Invisible Perimeter: How Boundaries Define Leadership

I experienced this in my company, but I see it everywhere. Lacking boundaries manifests in many ways across the C-Suite:

The Vague Visionary: Has poor boundaries around their own curiosity. They change the company strategy often, creating “Strategic Whiplash” for the team.

The Filterless Communicator: Has poor emotional boundaries. The leader “over-shares” their anxieties or half-baked ideas with the entire staff, causing unnecessary panic because they haven’t learned to use their board or a coach as a perimeter.

The Approval Seeker: Has poor boundaries around time. Because they haven’t set a boundary around their deep-work time, they become a high-paid administrator reacting to every department’s priorities.

And so on, and so forth with countless examples.

The Impact of Poor Boundaries

A boundary is the psychological and operational perimeter that protects a founder’s most valuable asset: Clarity of Judgment.

You are not measured by tasks completed, but by the quality of your decisions regarding Vision, Capital, and People.

Impact on Vision: The Competence Trap

Vision requires a CEO to look at the horizon. When you lack strong boundaries, you succumb to the gravitational pull of “doing what you’re good at.” Rewriting copy or debugging code feels safe—it provides a dopamine hit of “value.”

But when you do this, you are a symphony conductor who has sat down in the string section. You might hit the right notes, but the orchestra has lost its cohesion. You have traded the podium for a chair, and the music suffers.

Impact on Capital: The Dilution of Velocity

Without clear boundaries, your capital becomes a humidifier—misting the air in ten directions instead of a laser cutting through your target market. A leader who says “yes” to marginal ideas wastes the velocity of capital. The result may be a product that is feature-rich but profit-poor, sold in markets you have no business being in.

Impact on People: The Culture of The Shadow

When you have poor boundaries around role—answering Slacks at 2 AM or jumping into channels you don’t belong in—you cast a destructive shadow. You create a “theatre of productivity” where people stay online just to be seen. High performers leave for autonomy; those who tolerate micromanagement stay for the paycheck.

The Identity Trap: You Can’t Just “Read” This Into Practice

If you are nodding your head right now, be careful. That’s probably just a dopamine hit, not transformation.

Boundaries are tied to identity beliefs held for decades. “My value is my utility,” or “I am a good person because I help.” The list goes on.

Deep work is required.

Without the deep work, the brain will revert to its old identity the moment pressure spikes. You will justify stepping back into the trenches as “necessary” when in reality, it is a retreat to a comfortable, destructive identity.

True change doesn’t happen by learning a new “hack”; it happens in transformative work where you rewrite your identity and safely get to strengthen and practice it.

The Boundary Audit: A Process of Inquiry

If you want to move from “nodding” to “being,” you must audit your life through the lens of open, curious, self-inquiry. Often! I did the work for many years myself, and still do, and didn’t know it would lead me to eventually helping other founders and executives.

A great coach ask questions to your blind spot and holds space for you to show up and do the work. Coaching questions show up uniquely to every person, but some examples to uncover old beliefs might look like:

“How am I complicit in creating the conditions I say I hate?”
“What is the ‘payoff’ I get from jumping in?”
“Does solving this fire make me feel more valuable than the long-term work of strategy?”
“If I died tomorrow, which of these processes would stop immediately?“
“Why have I built a system where I am so needed all the time?”
“Am I actually helping my team, or am I stealing their opportunity to become competent so I can stay relevant?”

Examples of Boundaried Responses

Once your identify changes, your language changes. Leaders who go through the deep work learn to attune to their intuition and consequently develop language that helps them show up healthy under pressure. Again, from my own experience, I can share some examples:

The Shift

There is no hack. True change doesn’t happen in the reading. It happens in the deep work of transformation. You become who you need to be, or you revert to who you were.

Boundaries make the difference between a founder who “hustles” and a CEO who “leads by vision.” By defining where you end and the company begins, you don’t just save your sanity—you give your people the space they need to grow. And if you build a culture where your people grow, by extension and consequence and good fortitude, your company will grow and thrive.

Leadership Boundaries: Questions Founders Ask Me

What happens when a leader has poor boundaries?

It looks different on everyone. Strategy that changes monthly and whiplashes the team. Oversharing every worry. For me, it was avoiding a conflict I knew I had to have. However it shows up, you become the bottleneck, and the people around you never get room to grow.

Why can a servant leader end up hurting the team?

I watched it with a co-founder everyone loved. Genial, tireless, first into every fire. A leader who cannot hold a boundary cannot delegate, so the team learns to escalate instead of deliver. We paid top salaries to watch a good man burn out while no one underneath him grew.

What is the real cost of avoiding a hard conversation?

Higher than the conversation ever would have been. I avoided one I knew was right because I wanted my own comfort, and the dysfunction spread while my revenue masked it. Then an outage hit. Millions gone overnight, years of sales gone in a week. My clean hands were a form of negligence.

What is a leadership boundary?

It is the line that protects the one thing only you can give: clear judgment about vision, capital, and people. Lose it and you drift into the work that feels good, rewriting copy, fixing bugs, while the bigger calls go unmade. A CEO doing that is a conductor who sat down in the strings.

How do I know if I am the bottleneck?

Sit with a few honest questions. How am I complicit in the very thing I complain about? What do I get out of rushing in to save the day? If I vanished tomorrow, what would simply stop? And the hard one: am I helping my team, or keeping them dependent so I stay needed?

On what happens when you have become the bottleneck your company cannot grow past: When Scaling Your Company Is Breaking You.

The post Boundaries: The Invisible Perimeter to Scale appeared first on Allen Adjamian.

“I’ll get to it later, I have time” was a very seductive lie I told myself throughout my tenure as a CEO. I would get in great shape when my net worth hit X and I would hire a personal trainer, I had time. I would enter a meaningful, heartfelt relationship when the executive team could run the day-to-day without me, I had time. I would learn guitar (for my third attempt) and record my music, I totally had time. I’d start a family, plenty of time for that. I would spend more time doing what I loved.

I believed that circumstances would one day align when my calendar and bank account finally cooperate – which makes me chuckle now writing that. Over 17 years as a Founder and CEO, I paid the price for putting my dreams off, despite a lot of financial and outward success. And life looked as such for other founders in my network. They were gaining unwanted weight, getting depressed, withdrawn, cynical, divorced and disconnected from the vibrant life force that got them into entrepreneurship in the first place. And the companies were struggling, stagnating and the exit strategy had become a mirage.

As is the case, most leaders survive on deferred maintenance. Founders have normalized it. Executives institutionalized it. The drift away from what matters most is subtle, but the cost is absolute and very palpable.

The things that matter most – health, relationships, creativity, meaning – generally do not collapse suddenly. They erode. They degrade not through crisis, but through postponement. Health withers, relationships drift while purpose dissolves into mere output. It happens via the quiet internal whisper that says “I’ll tend to this when things calm down. When the product ships. When the round closes. When my net worth hits X.“

But that is not valid reasoning, it is a protective narrative hard at work. It is a psychological veil that shields you from confronting old beliefs you were trained to obey – beliefs about worth, safety, and what you’re truly allowed to experience out of life. I wore that veil for many, many years.

Because “later” is a soothing anesthesia.

It lets you avoid the exploration with the part of you that is afraid of deep change, afraid of your heart’s calling, or afraid of taking yourself and your life’s purpose very seriously.

But anesthesia always has an invoice.

You think you are investing in a better future as a leader, but you are making payments to your past.

“Later” compounds over time. Like interest on a loan, the cost rises quietly until one day the beliefs that no longer serve you have foreclosed on your dreams.

It’s commonplace that we discover these insights too late. The old stories of waking up to symbols of success with no meaning, no vitality and often depressed. So many founders and executives feel it as an inescapable fatigue, a hollowing gap between external success and internal stagnation. They assumed life would expand when success did. It didn’t for me and many in my entrepreneurial circles. It never does. The outside scales. The inside does not — unless you proactively work on it.

If you want a life you enjoy later, the only material you will ever have to build it with is how you act today. Not when you feel ready, not when the company stabilizes, and not when you have more money or more confidence.

Working on managing the psyche is the only point of leverage we have. It is the only environment where change is real rather than conceptual. Because we do not see things as they are, rather we see things as we are. And if what you see is no longer serving you, well.. what are you going to do with that awareness?

Whatever can be done about it is probably going to require ongoing support and resources to make a lasting impact. For me, it was having someone trusted and experienced in my corner – and it still is.

The work we do is not about forcing discipline. It is about dissolving the beliefs that keep you postponing your own high quality life and the success of your entrepreneurship. It is about identifying and growing out of the narratives that once kept you safe but now keep you stagnant. The coaching work we do together is to interrupt the automatic payments you keep making to your past and start cultivating the life you do want and deserve.

Later is too late. Your future is shaped only by what you intentionally put into practice today.

If you are feeling called to explore deeper, I’d welcome getting to know you.

Deferred Living: Questions Founders Ask Me

Why do founders keep putting off the things that matter?

Because the word later is a soothing anesthesia. Telling yourself you will tend to your health, relationships, or creativity once the round closes or the product ships lets you avoid the part of you that is afraid of real change. It feels like reasoning. It is a protective story, and I wore it for years.

Why does outward success start to feel empty?

Because the outside scales and the inside does not, unless you work on it. Many founders assume life will expand when success does. It does not. You can wake up to every symbol of success and still feel a hollow gap between the achievement and any sense of vitality or meaning.

What does it actually cost to keep saying I’ll do it later?

It compounds, like interest on a loan. The cost rises quietly until the beliefs that no longer serve you have foreclosed on your dreams. Health withers, relationships drift, and purpose dissolves into output. None of it collapses at once. It erodes through postponement.

How do you stop deferring your real life?

The work is dissolving the beliefs that keep you postponing your life, the narratives that once kept you safe and now keep you stagnant. It is not about forcing discipline. The only material you have to build a better life is how you act today, not when you feel ready or when the company stabilizes. For me, that meant someone trusted and experienced in my corner.

On what it costs to keep deferring the things that matter most: What to Do When You’ve Lost the Fire for Your Startup.

The post Later is Too Late appeared first on Allen Adjamian.

“Increase revenue 30%.”
“Improve employee engagement by 15%.”
“Increase NPS to 50”
“Execute product launches 20% faster.”

The CEO presents them confidently. Leadership nods. They cascade into OKRs. Employees update dashboards. Slack fills with optimism.

By April, execution is uneven.
By July, priorities have drifted to the shores of status quo.
By October, the goals are quietly revised or rationalized. PIPs rumble through the organization.
By December, everyone agrees the goals were “directionally right” but unrealistic given the year.

This cycle repeats so often that failure itself becomes normalized.

The problem is not effort.
The problem is how goals are conceived.

How CEOs Typically Set Goals

Most CEOs set goals using one of three approaches.

1. Goals as Numeric Targets

Revenue. Headcount. Market share.

These goals are easy to measure and easy to defend to a board. They are also emotionally inert, therefore they narrow staff attention to outcomes. But numbers do not guide people on who they need to be become in order to achieve these outcomes. Managers translate lofty targets into pressure. Employees respond by negotiating, optimizing locally, gaming metrics, or blaming unclear instructions. Fear replaces true ownership. Respect is lost. Culture becomes competitive instead of cooperative. And in the spirit of Peter Drucker – culture snacks on strategic goals all year long. Execution fails from fear-driven behavior implicitly embedded in the system to hit a new goal.

2. Goals as Aspirational Statements

“We will be best-in-class in support.”
“We will retain 95% of clients”
“We will execute faster across all departments.”

These statements sound motivating, but they do not change how work is done. They express intent without specifying what decisions, behaviors, or tradeoffs must change as a result.

Because nothing concrete is defined, each function fills in the gaps for itself. Product interprets “execute faster” as shipping more. Sales interprets it as pushing deals sooner. Marketing interprets it as launching campaigns earlier. No one is wrong, but no one is aligned.

Since no behavior is modeled or enforced, there is nothing to reinforce. The statements appear in decks and all-hands meetings, then quietly disappear from daily work.

With no change to decisions or incentives, energy returns to the existing way of operating. The goal fades, not because people disagreed with it, but because it never affected what they actually did.

3. Goals as Cascaded Tasks

The CEO defines objectives. Leadership breaks them into OKRs. Managers translate those OKRs into narrow, local metrics. Employees work to satisfy the metrics tied to their role.

This creates the appearance of alignment, but the original goal is fragmented into disconnected targets, to be optimized in isolation.

Because performance is evaluated locally, people prioritize what they can control and measure. When tradeoffs arise, they choose the metric over the intent behind it.

Over time, the system stops responding to the goal itself and starts responding to the measurements created in its name. Coordination breaks down. Teams succeed locally while the organization stalls globally. That means many OKR targets are hit and the company still misses its goal.

Execution suffers not because people ignore the goal, but because cascading it converted intent into competing incentives.

Why Goals Do Not Stick in Company Culture

Goals fail for structural reasons because the system they are placed into is not designed to support them. Effort increases, intent is clear, but the underlying mechanics of decision-making, incentives, and authority remain unchanged.

Goals Bypass Identity

People do not change behavior just because a goal exists. People change behavior when a goal fits how they see themselves and how they believe success is achieved.

When a goal conflicts with identity, people comply outwardly and resist inwardly. They follow the letter of the goal while preserving the behaviors that have kept them successful and safe.

Example.
A company may declare a goal to “move faster,” but if promotions, praise, and credibility have historically gone to those who avoid mistakes and maintain polish, the real identity remains being “risk-averse”. Under pressure, people revert to caution, escalation, and over-analysis.

The stated goal fails because it never became part of who the organization believes it is.

Goals Ignore Internal Conflict

Inside every organization are competing priorities, fears, and incentives. Leaders want growth and stability. Managers want clarity and protection. Employees want autonomy and safety. These needs can coexist, but they pull in different directions when pressure rises.

Traditional goals assume these tensions will resolve themselves. They declare a shared outcome without addressing what each group risks by pursuing it.

Example.
CEO announces a goal to “move faster.” In the meeting, everyone agrees. No one objects. Afterward, managers keep extra reviews in place to avoid mistakes. Employees escalate decisions instead of owning them. Teams move cautiously to protect their metrics and roles.

Publicly, the goal was accepted. Privately, the system made speed impossible.

Goals Are Detached from Real Decision-Making

Most goals live in documents. Decisions live in meetings. When goals do not change how tradeoffs are made in those meetings, they have no effect on behavior.

Example.
A company goal states customer retention is a priority. In a planning meeting, the team must choose between fixing a reliability issue or shipping a feature tied to a big sales deal. They choose the feature to protect the revenue number.

Under pressure, people fall back on familiar decision patterns, and the organization returns to the status quo precisely when it matters most.

Goals Are Treated as Outcomes, Not Constraints

CEOs often define what they want without defining what they will no longer tolerate. When CEOs define goals without setting boundaries on time, attention or capacity, teams try to do everything at once. No work is stopped, tradeoffs are avoided, and capacity is silently exceeded. The system becomes overloaded, and effort increases without progress.

Example.
A CEO says growth, reliability, and innovation all matter this year. No projects are cut. Teams stretch to deliver everything. Deadlines slip, quality drops, and people burn out.

Nothing changed because no constraints were introduced. The reward is burnout and frustration.

The Frustration Loop

When goals fail structurally, a predictable emotional loop forms.

CEOs see missed targets and conclude the organization is not stepping up. Managers feel trapped between ambitious goals and unchanged constraints. Employees experience shifting priorities and growing cynicism.

Each group reacts rationally to its position, but in isolation. CEOs push harder. Managers buffer and reinterpret. Employees disengage.

Each group blames a different layer. No one questions the goal-setting model itself.

The Principle That Changes Everything

Goals do not drive behavior.
Conditions drive behavior.

People act consistently with how they make meaning under pressure.

That means they act consistently with how decisions are rewarded, how risk is treated, and what feels safe under pressure. Meaning is not abstract. It is shaped by incentives, authority, and past consequences.

When pressure rises, people don’t consider the company goals. They follow the rules the system has taught them through experience.

Effective company goals change how decisions are made, who has authority, and who owns the outcome.

An Effective Way to Set Company Goals

The CEOs who break the cycle do something fundamentally different. They stop asking, “What should we achieve?” and start asking, “Who must we become for this goal to be inevitable?”

Step 1: Start With the Truth, Not the Vision

Before setting goals, the CEO surfaces the unspoken realities of the organization.

Where do decisions stall?
Where is accountability diffused?
Where does fear masquerade as professionalism?
Where do incentives quietly contradict stated values?

This requires restraint from fixing too quickly, defending past decisions, or softening the truth to keep things comfortable. The tradeoff is discomfort now versus failure later.

Until these truths are named, goals are fantasy.

Step 2: Define the Few Conditions That Matter

When too many goals exist, teams decide for themselves which ones matter in the moment. That creates inconsistency, politics, and slow execution.

Instead of many objectives, effective CEOs define a small number of non-negotiable conditions that govern how work gets done.

Examples:
Decisions are made with full ownership, not consensus. For any decision within a defined threshold, one person owns the call. Input is welcome. Agreement is not required. Once the decision is made, it is final unless materially new information appears.

Information flows directly to decision-makers, not through hierarchy. Customer data, risks, and failures are surfaced directly to the people who can act. Information is not summarized, softened, or delayed to protect layers of management.

Leaders trade personal comfort for organizational clarity. Leaders address conflict early, make unpopular calls when needed, and remove ambiguity even when it creates discomfort.

These are not slogans. They are constraints on behavior.

Step 3: Translate Conditions Into Observable Behavior

Each condition is translated into specific, visible changes in how work happens.

What meetings change?
What decisions move faster?
What behavior is no longer acceptable, even if results are good?

Examples:
If decisions are made with full ownership:
Which decisions are final unless materially new information appears?
Who owns those decisions and is expected to explain them when outcomes are poor?

If information flows directly to decision-makers:
What information now bypasses layers of management?
How quickly is it expected to reach someone who can act?

If leaders trade personal comfort for clarity:
Which conversations happen sooner instead of being deferred?
What behavior is no longer acceptable, even if short-term results look good?

Step 4: Model the Cost Personally

New conditions may ask people to take risks they were previously punished for taking. If the CEO does not publicly take those risks first, the organization will not believe the conditions are real. That risk is rarely financial. It shows up as reduced control, greater exposure, or delayed personal wins.

Who will the CEO become so that their organization thrives as it progresses towards those goals?

Examples:
Reduced control The CEO stops acting as the final decision-maker on product calls and lets an executive own the outcome, even when the decision is uncomfortable.

Increased exposure The CEO openly names a failed decision they made and explains the reasoning, without blame, signaling that mistakes are discussable rather than punishable.

Delayed personal wins The CEO supports a long-term product fix over a short-term revenue boost, even though it weakens a quarter’s narrative.

When the CEO takes that cost first, fear drops. Ownership rises. Authority stops enforcing compliance and starts making it safe to decide.

Step 5: Let Outcomes Emerge

When conditions are stable, outcomes follow. You cannot force growth through pressure any more than you can PIP a tree into growing faster. Pressure may increase activity, but it does not change what the system can produce.

Growth becomes inevitable only when the conditions that produce it are in place.

When decisions are clear and owned, teams stop revisiting the same issues and move forward faster. For example, a product decision made once and held allows Sales, Marketing, and Customer Success to align instead of hedging or constantly revisiting.

When behavior is healthy and consistent, culture strengthens. People stop guessing what is safe and start acting with confidence because expectations do not change week to week.

When ownership is real, execution accelerates. Work does not stall in review cycles or escalation loops. Problems surface earlier and get resolved by the people closest to them.

At that point, the goal is no longer chased. It emerges as a byproduct of a system designed to produce it.

A Goal Barometer

A company goal is well-set if the answer to this question is clear:

“When pressure hits, what will we do differently without needing to be reminded?”

If the answer is vague, the goal will fail.
If the answer is embodied, the goal will stick.

That is how effective company goals are set in a way that actually works. Of course, every company is unique and their goal setting must be unique. The examples provided are universal enough to drive the point but it is important to treat each company as its own – the goal setting methodology is universal, the solutions that come as a result are highly specific.

And if you need someone to talk to, I’d welcome getting to know you.

Setting Company Goals: Questions Founders Ask Me

Why do company goals fail every year?

Not for lack of effort. They fail because the system underneath them never changes. You can write the targets, cascade the OKRs, rally everyone in January, and when pressure hits people still do what the old incentives taught them. The goal was never the problem. The conditions were.

Why do teams hit their OKRs but the company still misses its goal?

Because cascading a goal slices it into local targets everyone optimizes alone. People protect the number they are measured on, and when it conflicts with the real intent, the number wins. Everyone succeeds in their lane while the company stalls. I have watched it happen and helped leaders untangle it.

How should a CEO set effective company goals?

Stop asking what we should achieve and ask who we must become for it to be inevitable. Name the truths no one says out loud, set a few non-negotiable conditions for how decisions get made, and model the cost yourself first. The outcome follows the system you build.

What is the difference between goals and conditions?

A goal is a target you point at. A condition is what actually governs how people decide when you are not in the room. Goals do not drive behavior. Conditions do. Most founders are setting targets and quietly hoping the behavior follows. It rarely does.

How do I know if a company goal is well set?

Ask yourself one thing: when pressure hits, what will we do differently without anyone needing to be reminded? If the answer is vague, the goal will not hold. If it is already lived in how people decide, it will.

When growth itself starts breaking you, the goals are rarely the real issue: When Scaling Your Company Is Breaking You.

The post How to Set Effective Company Goals appeared first on Allen Adjamian.

The quiet ache of aging is discovering how many of my limits were self-authored.

I could have…

Three deceptively simple words that sit at the center of every leader’s private post-mortem. Every founder, every executive, every high-achiever eventually arrives at this same realization: the great barrier was never time, talent, funding, or circumstance. It was the narrative architecture of the self—identity, fear, inherited scripts, unconscious beliefs.

The pattern is universal because the mechanism is universal. People don’t fail because they’re incapable. They fail because they cannot see the story they’re living inside.

Coaching names this directly: the human psyche is built on protective narratives that once kept us safe and now keep us small. They operate automatically. They feel factual. They define the possible without announcing themselves.

Executives don’t walk around saying, “I’m living out my unexamined childhood survival strategy.”
They say things like:

“I’ll take care of it.”
“It’s faster if I just do it myself.”
“I need more data before I make the call.”
“This decision has to be perfect.”
“My board won’t support that direction.”
“My team isn’t ready for more responsibility.”
“I shouldn’t ask for help.”
“I’ll deal with it when things slow down.”

These sentences sound rational. They sound mature. They sound like leadership.

Underneath them is something far more primal: a story about who you must be in order to be safe, respected, valued, or in control.

This is where your years disappear.

A founder spends three extra years avoiding a necessary executive hire—not because the candidate isn’t good enough, but because somewhere in his internal logic, delegating authority threatens his very identity as the one who holds everything together.

An executive waits too long to address a toxic VP—not because she doesn’t know what needs to be done, but because a lifetime of conflict-avoidant conditioning interprets direct confrontation as danger.

A leader endures chronic overwork—not because the business requires it, but because the belief “I am only worthy when producing” has been running in the background since adolescence.

These are not operational challenges. These are identity constraints disguised as business decisions.

No one notices when the shift happens. It’s quiet. Gradual. It looks like routine. Deadlines, meetings, investor updates, product cycles. Another quarter. Another year. And then, during a rare moment of stillness—vacation, illness, burnout, a failed raise, a board conflict, a resignation—reflection sharpens into a painful clarity:

I could have hired earlier.
I could have spoken up sooner.
I could have trusted my instincts.
I could have listened instead of defended.
I could have slowed down before the crash.
I could have asked for support instead of white-knuckling everything.
I could have become someone different far earlier than I did.

It’s not regret. It’s revelation. The human equivalent of discovering a door you never noticed in a room you’ve lived in for decades.

This is the work we do in coaching: widening the field of vision beyond the stories that once felt like truth.

This is deep work to shift from subject to object. What once owned you becomes something you can see, name, and work with.

The belief “I am responsible for everything” becomes “I am carrying responsibility to avoid feeling unnecessary.”

The belief “I must prove myself” becomes “I learned early that love was conditional on performance.”

The belief “I cannot be vulnerable” becomes “I am protecting the parts of me I’ve never allowed into the light.”

When leaders begin to examine these foundations, their range expands. Decisions that once felt paralyzing become simple. Conversations that once felt dangerous become clarifying. Directions that once felt impossible become obvious.

You could have turns into you can.
And eventually, into you are.

You can not rationalize and nod your way into it, anymore than you can read a book on how to swim and become a swimmer – it must be a lived experience.

Executives and founders don’t hire coaches for tactics. They hire coaches to expose the internal architecture shaping their tactics. They hire coaches to interrupt the unconscious flow of “you could have” before it ossifies into years lived on the wrong narrative. Trust me, I lost a lot of years before I learned these lessons and how to live by them.

Coaching is not about fixing. It is about revealing—what you’re carrying, why you’re carrying it, and what becomes possible when you stop mistaking old beliefs for current reality.

That is the pivot point – where “I could have” becomes “I did.”

If you feel coaching would benefit where you are in your journey, I welcome a chat.

The Stories Behind Our Decisions: Questions Founders Ask Me

Why do founders wait too long to make obvious decisions?

Because the thing in the way is rarely the decision. It is who you would have to become to make it. I waited years on calls I knew were right because making them threatened how I saw myself. We work on exactly that, the identity underneath the delay.

What do executive coaches actually do?

Founders do not come to me for tactics. They come because the same patterns keep producing the same results and they cannot see the story they are living inside. My work is to help you see it, name it, and choose differently. I am not fixing you, I am revealing what is already there.

Can you learn this from a book instead of coaching?

I wish. You cannot read your way into it any more than you can read a book about swimming and then swim. It has to be lived, in real time, with someone holding the space. That is why this work happens in the room, not on the page.

What is the shift from I could have to I did?

It is the moment a belief that ran you becomes something you can see and choose about. Suddenly the decision that felt impossible is simple, and the conversation that felt dangerous just clarifying. That shift is what I hold space for in coaching.

More on the stories we tell ourselves about what was possible, and the work of changing them: Identity-Level Coaching for Founders.

The post You Could Have… appeared first on Allen Adjamian.

Coaching operates in a space between potential and willingness. I can walk beside someone, ask the right questions, create space for reflection, but if they’re not ready to look inward and do the work, the process doesn’t land. Coaching isn’t about performance tricks or productivity hacks. It is not advice, nor consulting – those are mutually exclusive of coaching. It’s about confronting long-held and unaddressed beliefs and patterns, which requires courage, vulnerability, and a resolute, internal readiness.

So how do you know when you’re ready for coaching? Usually, it’s not from a book or a podcast. It shows up in lived experience. External signs emerge first: the nights where sleep won’t come because your mind keeps replaying the same decision; the creeping dissatisfaction even in success; the team that feels off; the company culture that doesn’t resemble the one you thought you were building; the results that no longer feel worth the cost; a desire to bow out of a company that’s doing well.

Then there are the internal signs. The silent weight of stress that no amount of strategy fixes. The dull fatigue that lingers under every achievement. The strain in your relationships. The loss of meaning, of purpose. The repeating thought, I can’t keep doing this like this. These are not failures. They are signals. Blaring signals, the psyche’s way of inviting you to take action towards growth.

Every single word I write, I have lived deeply. In addition to many roles and ventures, I was CEO of the same company for 15+ years. I’ve been in the deep trenches of founder burnout and I’ve also come out the other side, healthy and grateful.

If any of this resonates, coaching can help. It’s not about fixing what’s wrong; it’s about uncovering what’s true, beautiful and meaningful within you. The readiness isn’t about having answers; it’s about finally being willing to explore your deeper questions on this amazing journey you are on.

Coaching Readiness: Questions Founders Ask Me

How do I know if I am ready for coaching?

Usually you feel it before you can name it. Sleepless nights replaying a decision, dissatisfaction sitting underneath your success, the quiet thought that you cannot keep doing this the way you have been. When that arrives, you are ready. That is exactly what we explore together.

What is the difference between coaching and consulting or advice?

I am not here to hand you a playbook or tell you what to do. Consulting and advice do that. Coaching is different: I walk beside you and ask the questions that surface what you already know but have not let yourself see. That distinction is the whole thing.

What does coaching actually work on?

Not productivity hacks. The long-held beliefs and patterns running quietly underneath your choices, the ones that take real honesty to face. Less about fixing what is wrong, more about uncovering what is true and meaningful in you. That is the ground we cover together.

Why do you only coach people who are ready?

Because I cannot persuade someone into change, and I would not want to. I spent my career in sales and I am good at it, but coaching is not something to sell. When someone is genuinely ready to look inward, the work moves. When they are not, it does not.

If you’re weighing whether this kind of work fits where you are, here is how I work with founders: How Coaching With Me Works.

The post I Only Coach Those That… appeared first on Allen Adjamian.

I walked into therapy that year not because I wanted to grow as a person, but because I believed everyone else was the problem and I needed to know how to better control the outcomes I sought. It wasn’t even seeking help about my anxiety, just anger-led to go see the bearded therapist to fix the problems of my life. That first step began a seventeen-year commitment to my interior work—a journey that would eventually lead me from the practical tools of the present, to the deep archetypes of my past, and finally to the strategic design of my future.

The Early Years of Therapy

My initial years were spent in the world of Cognitive Behavioral Therapy (CBT). As a CEO, I treated therapy like any other optimization problem. My therapist got into my dense head that at the very least, I can’t think clearly when I’m angry and so I bought into some CBT resources. I wanted a quick fix for anger and stress to gain better focus and make sharper decisions. CBT provided a structured, actionable framework that felt familiar enough to a business mind.

The Benefits of CBT as a Founder:

Immediate Grounding: It provided “battlefield” tools to manage my anger in the middle of a high-stakes meeting.

Identifying Distortions: It helped me recognize when I was “catastrophizing” a missed quarterly goal or simply one lost prospect, allowing me to return to a more rational baseline.

Habit Restructuring: It offered a way to challenge the immediate, negative thought patterns that led to reactive decision-making.

However, as the company continued to scale and I acquired another company, I began to hit the boundaries of what this approach could offer. For a founder responsible for the culture and strategy of a large organization, the limitations became clear.

The Limitations of CBT from a Business Perspective:

Symptom-Focused, Not Future-Oriented: CBT is designed to get you back to a baseline so you don’t feel so anxious. But as a leader, I needed to move toward “times ten.” I needed a vision and a methodology for the future, not just a way to survive the afternoon.

Individual vs. Organizational: CBT gave me a breathing exercise for my stress, but it had nothing to say about how to handle a co-founder who, I felt, was undermining the company’s mission.

The “Why” vs. the “What”: It could help me change a thought, but it didn’t help me understand the deep-seated belief system that created that thought in the first place. It patched the leak but didn’t address the structural integrity of the dam.

The Descent: Jungian Analysis & the Shadow

My search for deeper answers eventually led me to a Jungian Analyst. If CBT was about managing the surface, Jungian therapy was an archaeological excavation. I spent more than a decade in this work, which is rooted in depth psychology and the process of “Individuation”, or becoming a whole, integrated human being.

Working with an analyst is a rigorous process. It involves looking into the “Shadow”—the parts of ourselves we have suppressed or denied because they didn’t fit our image of a “successful leader.” For much of my life I had relied on a rigid need for control and feared and rejected vulnerability, believing that combination was the engine of my success. In reality, they were the sources that fueled my exhaustion and my problems in the company.

As Carl Jung famously observed:

“Until you make the unconscious conscious, it will direct your life and you will call it fate.”

In the context of leadership, this is profound. The parts of a founder that remain unconscious will eventually run the company.

If you have an unconscious need for validation, you will build a culture of “yes-men.”

If you have an unconscious fear of conflict, you will allow toxic behaviors to persist. And so forth…

My years in Jungian analysis allowed me to stop calling my patterns “fate” and start leading from a place of conscious choice. This work took deep root in me; it changed the very nature of my presence in the office.

When Therapy Met Mentor

The transition toward coaching began during a lunch at Killer Shrimp in Marina Del Rey with my mentor Fred — a former C-level executive at IBM and Mattel. For the first time in our long history, I didn’t talk about revenue, scale, or product-market fit. I talked about the internal toll. I told him about the migraines, the anxiety, and the feeling that success was starting to feel like confinement.

Fred listened with the perspective of someone who had seen the same patterns in the boardrooms of global giants. He shared his own struggles with burnout during the high-pressure years at Mattel, back when toys were built to last with die-cast metal, he would tell me. That conversation opened a new branch in my life. It was the realization that while therapy was tending to my soul, I needed a different kind of partnership to redesign my entrepreneurial journey.

Questions Only a Coach Asks

While therapy often asks, “Where does this feeling come from?”, coaching might ask, “What is this feeling costing your vision?”

The inclusion of coaching wasn’t a replacement for therapy; it was an expansion. My coach asked me questions that a therapist, focused on my psychological well-being, never would have considered.

Here are a few examples of how that coaching lens changed my company:

1. The Question of Identity vs. Role

The Question: “You say you ‘have’ to make every final decision to ensure quality. If you were to die tomorrow, would the company fail because of a lack of talent, or because you’ve designed a system that requires your permission to exist?”

The Application: This hit my need for control directly. We looked at the “methodology of permission” I had built and how approvals all routed to me (with a nifty workflow that I thought was efficient but all it did was funnel more problems my way faster).

The Change: I dismantled my “NASA-style” dashboard of 50 metrics and narrowed it to 3. I empowered my team to make decisions without my input. We created a committee that could arrive at their own decisions and justification and act on it. The result? Decisions were made faster, employee morale improved because they felt trusted, and I finally stopped got room to breathe and spend time doing what was truly my role – getting more clarity on our vision and our long term direction.

2. The Question of Value Alignment

The Question: “You are optimizing for ‘Scale,’ but your stress suggests you value ‘Peace.’ What would happen if you optimized for ‘Peaceful Scale’ instead of ‘Growth at all Costs’?”

The Application: This forced me to look at our sales strategy. We were taking on “toxic” clients who paid well but drained our team’s spirit.

The Change: We fired our most difficult clients and we fired our bottom of the barrel clients and repeated it every single year. It felt like professional suicide at the time, but it cleared the air and made space for more lasting and sustainable growth. We replaced them with partners who aligned with our values. Our customer service improved, our referrals increased and customer loyalty went through the roof. Later when I came to sell the company, we saw that our client retention average was an astounding 12 years.

3. The Question of the “Founder’s Shadow” in Culture

The Question: “Your team is hesitant to give you bad news despite you insisting its ok. What is it about your reaction to ‘failure’ that has made silence feel safer than honesty for them?”

The Application: Through my Jungian work, I knew I hated failure. My coach helped me see how that internal hatred was manifesting as a “culture of fear.”

The Change: I started a regular lessons learned forum where I shared my own mistakes first. By making vulnerability a leadership methodology, I unlocked the creativity of the team. I didn’t expect it but issues that had been lingering for months were solved because people were finally brave enough to speak the truth.

The Synthesis of Therapy & Coaching

I stayed in deep therapeutic work years after my company was acquired, for what would be over 17 years. I’m a big advocate for everyone doing deep work. The only journey worth taking, in my humble opinion, is the one within.

Therapy is the work of the roots—it ensures the tree is healthy and grounded. Coaching is the work of the fruit. It is about the harvest—the strategy, the methodology, and the design of the future.

For the modern founder and CEO, the two are not mutually exclusive; they are interdependent. Here is it how I have experienced it:

If you are building something significant and feel the pressure stretching you thin, remember: the business can only grow as far as you do. Seeking support is not a sign of weakness; it an act of leadership. If you ever feel you need someone in your corner that’s been through it, I’d welcome getting to know you.

Therapy and Coaching: Questions Founders Ask Me

Do entrepreneurs need therapy?

I think the inner work matters more than almost anything we build. I started therapy at 30, anxious and migraine-ridden while the company thrived, and stayed with it 17 years. Whether it is therapy, coaching, or both, the only journey worth taking is the one inward.

Is CBT enough for a founder?

It helped me catch myself mid-spiral and get back to baseline. But baseline was never where I wanted to lead from, and it had nothing to say about the co-founder dynamic that was quietly breaking me. In coaching we go past coping, into who you are being as a leader.

What is the difference between therapy and coaching for a CEO?

Therapy tended my roots, the why behind how I am. Coaching is the harvest, how I lead from here. For me they were never either-or, I did both. In coaching we take what you understand about yourself and turn it into how you actually show up under pressure.

What is shadow work for a leader?

It is meeting the parts of yourself you buried to look like a strong leader. For me that was a grip on control and a fear of being vulnerable. The parts you will not look at end up running the company. Bringing them into the light is much of the work we do together.

More on the difference between healing the past and changing how you lead in the present: Identity-Level Coaching for Founders.

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