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Simplicity Is a Leadership Discipline, Not Just a Design Principle

The KISS principle , Keep It Simple, Stupid , originated as a design philosophy, most often attributed to Kelly Johnson at Lockheed’s Skunk Works. The idea was that a jet aircraft should be repairable by an average mechanic in field conditions with basic tools. If the design was too complex for that, it had failed regardless of how elegant it looked on paper. I’ve found that this framing is far more useful than people give it credit for, and not just in software architecture or product design. The principle applies with equal force to how we structure organizations, communicate strategy, and decompose business problems. In fact, I’d argue that the ability to simplify is one of the most underrated skills a technology executive can develop.

There’s a reason simplicity is hard, though. It requires a deeper understanding of the problem than complexity does. Anyone can add layers : more process, more roles, more abstractions, more slides in the deck. Removing layers demands that you truly understand what’s essential and what’s incidental. I’ve seen this play out dozens of times: a leadership team confronted with a messy business problem will instinctively add structure to manage the mess, when what’s actually needed is the courage to cut through it. The best executives I’ve worked with share a common trait : they can take a sprawling, ambiguous situation and reduce it to a small number of things that actually matter. That’s not oversimplification. That’s clarity.

Simplicity in Organizational Design

Org design is one of the areas where the KISS principle pays the highest dividends and is most frequently ignored. When companies grow, they accumulate organizational complexity the way a ship accumulates barnacles : slowly, one reasonable decision at a time, until the drag becomes significant. Every dotted-line reporting relationship, every matrix structure, every committee that exists to coordinate between other committees adds cognitive overhead for the people doing the actual work. I’ve found it useful to periodically ask a brutally simple question: can every person in the organization explain who they report to, what they’re responsible for, and how their work connects to the company’s goals? If the answer is no, your org design has become too complex.

This doesn’t mean org structures should be naive or flat for the sake of flatness. There are legitimate reasons for complexity : regulatory requirements, geographic distribution, the need to balance functional expertise with product alignment. The point isn’t to avoid all complexity but to ensure that every layer of complexity is earning its keep. Some practical ways I’ve applied this:

  • When adding a new team or role, articulate what specific problem it solves that cannot be solved by an existing team or role. If you can’t do this in one or two sentences, that’s a signal.
  • Favor clear ownership over shared ownership. Shared ownership sounds collaborative but in practice it often means no one is truly accountable, and accountability gaps create more organizational complexity down the road as people try to compensate.
  • Revisit org structures at least annually with fresh eyes. What made sense eighteen months ago during a rapid scaling phase may be adding unnecessary friction now.
  • Be wary of creating coordination roles to manage the complexity caused by other coordination roles. This is a classic sign that the underlying structure needs to be simplified rather than managed.

Communicating Strategy with Clarity

The second area where simplicity proves essential is communication, particularly when rolling out new strategies or plans. I’ve observed a pattern throughout my career: the leaders who have the deepest understanding of a strategy are the ones who can explain it most simply. Conversely, when a strategy presentation requires forty-five minutes and thirty slides to convey, it’s often because the thinking behind it hasn’t been fully resolved. Complexity in communication frequently masks uncertainty in thought. This is worth being honest with yourself about : if you can’t explain your plan simply, you may not understand it well enough yet.

There’s a practical dimension to this as well. When you communicate a plan to your organization, every person who hears it will interpret it through the lens of their own role, their own concerns, their own priorities. The more complex the message, the more surface area there is for misinterpretation. I’ve found that the most effective strategic communications share a few characteristics:

  • They can be summarized in a single sentence that captures the why, not just the what. “We’re consolidating from three platforms to one because our customers need a unified experience and our engineers need to stop maintaining redundant systems” is far more useful than a detailed migration roadmap.
  • They use concrete language rather than abstract terminology. “We’re going to reduce our time-to-deploy from two weeks to two days” lands harder and more clearly than “we’re investing in operational excellence.”
  • They acknowledge what’s not changing alongside what is. People absorb change more effectively when they have stable reference points.
  • They’re short enough that a manager three levels down can relay them accurately without a script.

Decomposing Problems to Their Essence

Perhaps the most valuable application of the KISS principle is in problem decomposition. The business problems that land on a CTO’s desk are almost never simple on their surface : they involve competing priorities, technical constraints, organizational dynamics, and market pressures all tangled together. The instinct in these moments is to try to solve the whole thing at once, to build a comprehensive plan that addresses every dimension simultaneously. I’ve learned, sometimes painfully, that this instinct is almost always wrong. The better approach is to break the problem down until you find the smallest meaningful pieces, then solve those pieces in sequence.

This is where the word “stupid” in KISS actually earns its place. It’s a reminder that our tendency toward complexity is often an ego-driven behavior : we want to demonstrate that we understand how complicated things are, that we can hold all the variables in our heads at once. But the mark of genuine expertise isn’t the ability to manage complexity; it’s the ability to eliminate it. When I encounter a problem that feels overwhelmingly complex, I force myself to answer three questions: What is the single most important outcome we need? What is the smallest action that moves us toward that outcome? What can we explicitly choose to ignore for now? Those three questions have saved me from building elaborate solutions to problems that didn’t require them more times than I can count.

Simplicity is not a destination you arrive at ; it’s a discipline you practice. Systems, organizations, and strategies all tend toward complexity over time because every individual decision to add something feels reasonable in isolation. The accumulated weight of all those reasonable decisions is what eventually slows companies down. The executives who keep things simple aren’t the ones who avoid complexity; they’re the ones who are vigilant about pruning it, who understand that every layer they add creates a maintenance burden that extends far beyond the immediate problem it was meant to solve. In my experience, the best technology leaders treat simplicity not as a nice-to-have but as a responsibility : to their teams, their customers, and to the future version of the organization that will have to live with today’s decisions.

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The Work Never Ends, and That’s Not the Problem

One of the most destructive mental patterns I’ve observed in technology leaders, and one I’ve fallen into myself more times than I’d like to admit, is the belief that relief is just around the corner. If I can just get through this launch. If I can just close this quarter. If I can just navigate this reorg, hire this key person, resolve this production incident, get past this board meeting. Then things will calm down and I can finally breathe.

This thinking feels rational in the moment. It’s a coping mechanism, a way to endure difficulty by promising ourselves a future reward. But it’s fundamentally flawed because it’s built on a premise that almost never holds: that the current pressure is an aberration, and that normalcy, some sustained period of calm, is waiting on the other side.

The Treadmill of Relief That Never Comes

In my experience, the work never ends. Not in any role worth having, and certainly not in technology leadership. The nature of our work is that we’re building things that don’t exist yet, solving problems that haven’t been solved before, and operating in markets that shift constantly. There is no steady state. The moment one major effort concludes, another emerges to take its place. Sometimes it’s already been waiting in the wings; sometimes it materializes from nowhere.

When you orient your entire mental and emotional framework around the idea that you just need to survive until the current crisis passes, several harmful things happen:

  • You give yourself permission to operate in an unsustainable way, burning reserves you’ll need later
  • You defer recovery, relationships, health, and reflection to a future that keeps receding
  • You experience the completion of each effort not as satisfaction but as brief respite before the next wave of anxiety
  • You train yourself to associate your work with suffering rather than meaning

I’ve watched executives operate this way for years, always on the verge of a breakthrough to some calmer existence. They become brittle. Their judgment suffers because they’re perpetually depleted. And perhaps most tragically, they miss the actual experience of their professional lives because they’re always looking past the present moment to some imagined future relief.

Finding Satisfaction in the Process Itself

The alternative is not to pretend the work is easy or that every day is enjoyable. Some days are genuinely hard. Some problems are genuinely draining. The alternative is to recognize that the texture of difficulty is the texture of the work itself, and that meaning has to be found within it rather than after it.

This requires a fundamental reorientation. Instead of asking “when will this be over?” you have to ask “how can I be present in this?” Instead of treating each challenge as an obstacle between you and some peaceful future, you have to see the challenge as the thing itself: the actual substance of what you’ve chosen to do with your professional life.

I’ve found that this shift becomes easier when I focus on smaller units of time. A quarter, a month, even a week can feel overwhelming when viewed as a block to be endured. But an hour? A single conversation? A specific decision? Those can be engaged with fully. Those can be satisfying in their own right, even when they’re part of a larger effort that’s stressful.

  • The satisfaction of helping someone think through a hard problem clearly
  • The small pleasure of writing something well, even if it’s just an internal memo
  • The engagement of debugging a complex issue with your team
  • The connection that comes from being honest with a colleague about a difficult situation

These moments are available constantly, but only if you’re actually present for them rather than mentally fast-forwarding to some future state.

Sustainability as a Practice, Not a Destination

I think many of us treat sustainability as a condition we’ll achieve once external circumstances allow it. We’ll exercise regularly once this project ships. We’ll spend more time with family once we’ve hired the right team. We’ll read more, think more, rest more, later. But later never comes, or when it does, new demands have already filled the space.

Sustainability has to be built into how you operate now, not deferred to some future configuration of your life. This doesn’t mean working less hard or caring less about outcomes. It means recognizing that you’re playing a long game, measured in decades, not quarters, and that how you engage with the work today is how you’ll engage with it for years to come.

The leaders I most admire have figured this out. They’re fully engaged with their work, often in demanding and high-pressure situations, but they’re not waiting for it to end. They’ve made peace with the reality that the work is the thing, and they’ve found ways to be present for it rather than enduring it. They’re not martyrs grinding through until some reward arrives. They’re practitioners who have found meaning in the practice itself.

Every day, every hour, every conversation can be satisfying in its own right if you’re actually there for it. But you have to give up the fantasy that the pressure is temporary and that relief is coming. The pressure is the job. The question is whether you can find a way to be fully alive within it.

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The Art of Calibrated Effort: Doing Exactly What’s Required

One of the principles I return to most often is deceptively simple: use the minimum amount of effort necessary to achieve the results you want. Not the minimum effort you can get away with, and not maximum effort as a matter of pride, but precisely the right amount. This sounds obvious, perhaps even lazy, but in practice it’s one of the hardest calibrations a leader can make. Most people err dramatically in one direction or the other, either grinding themselves into dust on problems that don’t require it, or convincing themselves that shortcuts won’t catch up with them.

The key word in this principle is necessary. Sometimes the minimum necessary effort is everything you have, every ounce of energy, every late night, every difficult conversation. When you’re navigating a critical product launch, managing a genuine crisis, or building something that will define your organization’s trajectory, half-measures will fail. The minimum necessary might be total commitment. But other times, the minimum necessary is literally zero personal effort because someone else is already handling it, the solution is obvious and doesn’t require your involvement, or the problem will resolve itself if you simply get out of the way. Both of these scenarios demand the same amount of effort from you: exactly what’s required, no more and no less.

The Two Failure Modes

I’ve observed two distinct patterns in how capable people miscalibrate their effort, and both are equally destructive to their effectiveness.

The first failure mode is unnecessary heroics. These are the people who treat every problem as worthy of their full attention and energy. They stay late to perfect things that were already good enough. They insert themselves into decisions their teams could make independently. They research exhaustively when a quick conversation would suffice. On the surface, this looks like dedication, and organizations often reward it because effort is visible while efficiency is not. But this pattern leads to burnout, creates bottlenecks, and paradoxically produces worse outcomes because finite energy gets spread across problems that don’t equally deserve it. I’ve known many leaders who wore their exhaustion as a badge of honor while their most important initiatives languished because they had no reserve capacity left.

The second failure mode is premature optimization—convincing yourself that things require less time, energy, or attention than they actually do. This is the person who ships before the code is ready because testing is tedious. Who has a difficult conversation in their head instead of out loud because it’s uncomfortable. Who skips the stakeholder alignment because they’re confident they already know what everyone thinks. This pattern is seductive because it feels efficient, and sometimes you get lucky and the shortcut works. But the compounding cost of cutting corners is severe: technical debt, broken relationships, misaligned teams, and problems that metastasize while you’re not looking.

Calibrating Correctly

The skill, then, is accurate assessment: understanding what a situation actually requires before deciding how much to invest. Several questions help me make this calibration:

  • What’s the cost of being wrong? High-stakes, irreversible decisions deserve maximum diligence. Low-stakes, reversible ones can tolerate faster, lighter approaches.
  • Who else can or should handle this? If someone on your team is capable and this falls within their domain, your involvement may actively harm the outcome by disempowering them.
  • What’s the real deadline? Not the artificial urgency, but the actual point at which delay causes harm. Many things feel urgent that aren’t.
  • Am I the bottleneck? Sometimes the fastest path is removing yourself from the process entirely.
  • What would good enough look like? Perfection is rarely the standard that matters. Understanding what sufficient actually means prevents both over-investment and under-investment.

These questions sound straightforward, but answering them honestly requires a particular kind of self-awareness. You have to notice when your ego is inflating a problem’s importance, when your anxiety is driving unnecessary activity, or when your discomfort is rationalizing shortcuts.

The Discipline of Restraint

What I’ve come to appreciate is that both kinds of miscalibration usually stem from the same root cause: discomfort with uncertainty. Overwork is often an anxiety response. If I just do more, surely that will guarantee success. Cutting corners is also an anxiety response: if I just declare this done, I don’t have to sit with the discomfort of ongoing effort. Neither actually addresses the uncertainty; they just provide the illusion of control.

The mature approach is to tolerate the uncertainty while making your best assessment of what’s actually required. This means sometimes watching a problem unfold without intervening, trusting that it will resolve without you. It means sometimes committing fully to something exhausting because you’ve accurately judged that this is one of the moments that demands it. And it means being willing to revisit your calibration when new information suggests you got it wrong. The goal isn’t to always be right about how much effort something needs — that’s impossible. The goal is to have a clear-eyed process for making the assessment and the flexibility to adjust.

Don’t make things more difficult or take longer than they have to. But don’t convince yourself that difficult things are easy just because you wish they were. The leaders I respect most have developed this calibration over time, and they apply their energy with intention rather than habit. They know when to push and when to wait, when to dive deep and when to delegate, when the minimum necessary is everything and when it’s nothing at all.


This is not laziness dressed up as wisdom; it’s the recognition that your capacity is finite and the demands on it are not, so spending that capacity wisely is itself a form of excellence.

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Never make the same mistake twice

One of my most important principles is to strive to never make the same mistake twice. We all make mistakes, and though it’s important to be accepting and understanding of these failures in ourselves and our team members, it’s equally important to extract as much educational value as possible from mistakes in order to improve. A goal and commitment of never making the same mistake twice is guide that can help us to extra maximum value from these learning experiences.

“Never make the same mistake twice” is a mantra that resonates with most people, because most people recognize that making the same mistake repeatedly is detrimental to personal growth and development. Every mistake we make is an opportunity for growth and self-improvement, as long as we take the time to reflect on what went wrong and how we can avoid making the same mistake in the future. By consistently learning from our mistakes, we can make steady progress towards our goals and become more efficient and effective in everything we do.

Another benefit of avoiding the repetition of mistakes is that it helps to build our credibility and trust with others. When we make the same mistake over and over again, it can cause others to question our ability and judgment. On the other hand, when we take the time to learn from our mistakes and make an effort to avoid repeating them, we demonstrate to others that we are reliable and trustworthy. This can be especially important in professional settings, where our reputation and credibility can significantly impact our success.

For these reasons, the principle of never repeating the same mistake has broad implications on a larger journey toward success and improvement, and can be a guiding light that leads to patience, a better work ethic, increase objectivity, humility, and open mindedness.

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Fearful decision making leads to bad outcomes

Making important decisions when afraid, in any context, can have negative consequences. This is as true for a business or technology team as it is in nature. When an organization is dealing with negative market trends and poor performance, fear can take hold among its employees and leadership. This fear can cause decision-making to be clouded by emotion, leading to rash and potentially harmful choices.

When this happens, it’s critically important for leaders to remain calm and focused. They must avoid making decisions based on fear and instead maintain focus on facts and logical thinking. Seeking out advice from trusted people in your network and outside sources can also be helpful in making well-informed decisions.

It’s crucial for businesses to recognize the potential negative effects of fear on decision-making and take steps to mitigate them. For example, finding ways to reduce stress within the group will promote clearer thinking and lead to better decisions. This can be a difficult challenge when there is mounting internal and external pressure and an atmosphere of increasing uncertainty, but by doing so, businesses can avoid making decisions that may exacerbate negative market trends and further harm their performance.

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Before you ask a question, make sure you’re prepared for the answer

Before you ask a question that may have a damaging answer, mentally double check to make sure you are prepared and ready to accept the worst possible answer. If you’re not, don’t ask the question.

Often people will ask me a sensitive question without fully realizing the ramifications of an unexpected answer. This could be an opinion of a person, or an evaluation of a project that the asker has championed. A positive, emotionally supportive answer is expected. If instead the answer is negative, the questioner will usually get defensive and the conversation will become strained.

That is an outcome that no one wants and that produces no value for either participant or for the organization. Before getting into that situation it’s far better to either frame your question in a way that leads to the type of answer you’re looking for, or to let unspoken criticisms remain unspoken.

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The things that frustrate us the most in others are often our own biggest weaknesses or fears

Repeatedly throughout my life, when I’ve met someone who had a particularly pronounced intolerance, for example against hypocrites or procrastinators or conceited personalities, it would turn out that one of that person’s own greatest character flaws would be that exact thing.

I don’t know why there is a connection but I’m certain that there is a connection, and being aware of it can help in navigating relationships. If someone I do not know well expresses a personality or cultural annoyance, I recognize that they are likely to exhibit this same behavior at a later time and can prepare for it.

Similarly, if I find myself becoming frustrated or annoyed by someone else’s character flaw, I first ask myself if it’s my own weakness in that area that is frustrating me, or something close to it. In those cases, sometimes by determining how to improve myself I can improve life for the other person as well.

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If you’re going to say something, first understand what you’re trying to accomplish

It’s easy to speak without thinking, leading to unintended consequences. Before you release words into the world and into other people’s ears, consider what you want them to accomplish. If you want to change another person’s mind, or to help them understand something, or to elicit sympathy then stop to consider if what you’re about to say actually will accomplish that or if you should tailor your communication.

Conversely, sometimes speaking is more about releasing something that is bottled up inside of you and less about having a specific impact on another person. If that is the case, consider if you want to do that next to someone whose relationship you value, or somewhere else, possibly alone.

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Navigation

In some ways this job is like a maze: where we wind up is rarely where we think we’re headed from the start. We also have limited information with which to navigate and, though there are methods and skills we develop to help us make the best decisions possible, sometimes the lack of information leaves us with nothing better than a gamble.

I’ve had several big successes in my career and honestly I’m less responsible for those successes than people would like to believe. Likewise, I’ve had some failures, and honestly I’m less responsible for those failures than it would seem to a casual observer. Certainly there are ways to measure CTO abilities and outcomes, but usually you have to dig in deeper than the resume bullet points or anecdotes that are often the only things communicated.

You can go through your maze and make all the best decisions and still hit a wall, or you can go through and make all the wrong decisions or act chaotically and get through in record time. Over a large enough sample size outcomes will normalize, but few of us do this long enough to get there, and usually early outcomes lead us into the mazes of our future.

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Management vs Leadership

A lot has been written on the subject of management vs leadership when it comes to guiding teams. I’ve heard it argued that great executives lead whereas poor executives manage. I think this fails to recognize that management and leadership are equally important and that success is not likely unless both are done well.

Peter Drucker has said that “management is doing things right; leadership is doing the right things.” The idea of managing people should not always imply micromanagement. Like nearly every other executive skill there are both strategic and tactical aspects of people management, and different levels of involvement ranging from deeply immersing yourself in a team member’s day-to-day to only framing success conditions for a project or role.

When I think of what management means as opposed to leadership, I think of setting constraints. There is a perception that setting constraints on mature, professional people is a waste of their abilities or even insulting, but I believe quite the opposite: failing to set constraints, or to put it another way, expectations, reduces the likelihood that people will find their way to success and makes it harder for them to succeed.

People know how to do their jobs better than you do (hopefully) but they don’t necessarily know what the broader group, or the rest of the organization, or the CEO, or the board, or your users, or the market really needs from them. It’s up to you to manage these expectations by setting very clear success criteria whenever possible, and to manage their paths to meeting those expectations by course correcting early and often if they begin to drift off course, because though everyone on the team should have the ability  to succeed on their own, almost no one will have the perspective to know how they’re doing at all times.