I started selling in 1994. I was a kid. Since then, I’ve been a rep, a manager, an RVP, a CEO. I’ve hired and fired sales leaders. Now I’m the Head of Enterprise Sales at Dify. I still coach select founders, CEOs, CROs, and other executives. Just not our competitors. Across 30 years and a dozen revenue roles, one thing has become apparent to me. Most sales leaders have short careers.

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.

It was close to midnight when my assistant and her husband rushed through my front door and found me collapsed on the floor.

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.

In one of my past ventures, my business lost millions, because I allowed a “Hero” to occupy the C-Suite. This is a hard truth to admit because I pride myself on my boundaries. But, I used his clear lack of boundaries as a buffer to avoid enforcing my own and to keep my peace – a peace that eluded me.

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.