Category: Coaching

Get an inside look at our methods and discover how coaching can help you overcome obstacles and reach your full potential.

  • Later is Too Late

    Later is Too Late

    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 They were gaining unwanted weight, getting depressed, withdrawn, cynical, divorced and disconnected from the vibrant life force that got them into entrepreneurship in the first place.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.

  • How to Set Effective Company Goals

    How to Set Effective Company Goals

    Every January, CEOs set ambitious goals. They gather at retreats with their executive team and come up with entirely unique goals. I’ll use a few common examples I’ve personally experienced – from $5M to $1B companies – to illustrate my points below:

    “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.

  • You Could Have…

    You Could Have…

    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.

  • I Only Coach Those That…

    I Only Coach Those That…

    I only coach those that are ready for coaching. That might sound selective, but after decades in leadership and sales, I’ve learned that true change doesn’t begin with persuasion; it begins with readiness. I spent most of my career convincing people to buy, to try, to act – I am extremely good at sales. Coaching is different. It’s not something to sell and I have no inclination to try. There is truth in the old adage, when the student is ready…

    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.

  • Later is Too Late

    Later is too late. Learn what it takes to cultivate the life you want now without waiting for…

    Later is Too Late
  • How to Set Effective Company Goals

    Every January, CEOs set ambitious goals. They gather at retreats with their executive team and come up with…

    How to Set Effective Company Goals
  • You Could Have…

    The most universal human regret is realizing too late that the barriers were internal, not external. The stories…

    You Could Have…
  • I Only Coach Those That…

    I only coach those that are ready for coaching. That might sound selective, but after decades in leadership…

    I Only Coach Those That…