Five practices to transform from a founder to a CEO
“The difference between an amateur and a professional is in their habits. An amateur has amateur habits. A professional has professional habits.” – Stephen Pressfield
Every successful founder starts out as an amateur. They have an idea, the gumption to think they might be able to pull it off, and the willingness to throw themselves fully into the sauce. The mountain of things they don’t know is matched only by their enthusiasm, so despite the fact that they make a lot of wrong turns, their hustle more than makes up for it. All this is the reason for the startup ethos, coined by Brad Feld in the early 2010s, to “Do more Faster.” The more they can do in a given cycle, the more data they’ll get and the quicker they’ll learn what they’re building.
But if it all goes well, at a certain point in the startup journey, everything flips.
They find product/market fit, they raise some capital, and they start to actually build their companies. Suddenly “do more faster” stops working. New projects or initiatives, previously the lifeblood of the process, start to cause more harm than good, and the startup risks drowning from trying to take on too much. At this point, “do less better” becomes a wiser plan.
Most founders’ first reaction is to jump into action. They apply their well-honed skill at defining and solving problems to the challenge of “how do I scale a company?” and in doing so begin to implement all sorts of solutions. Meeting structures. Values. OKRs. Complete company Operating Systems.
Some of these work, but more often the results are underwhelming. If I had a nickel for every founder who’s told me they’ve tried OKRs and they didn’t work, I’d have at least enough for a lemon-twist cone from Frosty Boy. The reason these tools and frameworks aren’t enough isn’t because of the tools themselves; it’s because the founders implementing them are not yet prepared to do so effectively. They’re not yet the right people.
The key to making this transition well is this: before making a fundamental shift in how the company operates, make a fundamental shift in how the founder operates.
And as Pressfield advises, the key to changing yourself into a professional is in adopting professional habits. You can’t become a great CEO without deliberate practice, any more than you can learn to bench-press 250-lbs without first lifting 135-lbs over and over again.
Each journey is different because each person is different, but in my work with dozens of hypergrowth founder/CEOs, I’ve identified five practices that can rapidly accelerate the process of transforming from a person who gets mountains of shit done to a person who consciously leads teams of teams toward shared success.
The five practices of an evolving leader
1. Meditation
“This is the very essence of meditation: we reprogram unconscious mental processes by repeating basic tasks over and over with a clear intention.”
– John Yates, Matthew Immergut, Jeremy Graves, The Mind Illuminated
I’ve written before about meditation - I believe it’s more important to leaders than business school. Meditation is the most direct way to become intimately familiar with how your mind works, and as such, is the most effective foundation for changing it.
The transition from founder to CEO requires shifting the patterns of your mind. From hustle to precision. From being superman to deliberately not solving problems so as to create space for reports to develop their own superpowers. From gaining your sense of success from individual accomplishments to establishing a nexus of self worth around your team’s success. From pinching every penny to spending aggressively against the right metrics. None of this feels good, at first, and your well honed instincts as a scrappy founder will tell you to pull back from the ledge.
But with practice, you can change your instincts to more closely match those that suit the stage of your company.
Meditation allows you to develop the skill of seeing your unique thought patterns in real time, and, eventually, to change them. I’ve written about this process before, so I’ll refer you to the two articles below for detailed “how-to” guides on meditation for leaders.
2. Journaling
“It is not enough to be busy; so are the ants. The question is: What are we busy about?” ― Henry David Thoreau
The only logical endpoint of the “do more faster” phase is a chock full calendar and to-do list. However, the very thing that makes a founder successful in the early stages – the ability to chop down enormous numbers of trees – can keep her stuck chopping trees on one side of the forest all day, while the other side burns. To develop a proactive, intentional approach to work and your own thinking, you have to zoom out, spend time with the big picture, and stop reactively chasing the latest fire or opportunity.
Zooming out is a learned skill, and the best method I’ve found to develop that skill is a daily (morning) journaling practice. The act of writing blends the best parts of linear, intentional deep thinking and the best parts of talking with a thought partner, into a single act that reliably clarifies a person’s thinking. Its effects compound over time; I’ve yet to meet a person who journals regularly that is not also exceedingly thoughtful in the way they conduct their lives. Good writers are good thinkers.
There are many ways to journal, but the one I most often suggest is Morning Pages, originally created by creativity guru Julia Cameron. The instructions are simple: write three pages of anything you want, longhand or typed (Julia is a strict longhander, but in my experience clients find either works. If you really like digital, here’s a fun way to gamify the process), every morning. You can even write “I don’t know what to write” over and over again for three pages if you like. Just don’t stop before you’ve filled three pages.
Cameron suggests Morning Pages because of its ability to prime a person’s creative pump (this video of John Mayer’s creative process illustrates). I can attest to its creative power, but I’ve also found it’s a cheap and effective way to examine your thinking, clarify your beliefs and goals, wrestle with difficult topics, and develop accountability, all on a daily basis. In other words, it’s cheap, timely executive coaching. Either way, both Julia and I agree on one thing, “Morning Pages will change you.”
3. Say no to important things every day
“The more you believe you might succeed in “fitting everything in,” the more commitments you naturally take on, and the less you feel the need to ask whether each new commitment is truly worth a portion of your time—and so your days inevitably fill with more activities you don’t especially value.” – Oliver Burkeman, Four Thousand Weeks
If the first two practices can be a challenge to implement, this third one is downright threatening. It also may be the least negotiable of all of them. To evolve from a hustler to a leader, you have to make choices. And because the number of good ideas grows apace with the company, you have to develop the ability to say no to good ideas if you want to have any hope of consistently executing the great ones.
“Startups don’t starve, they drown.” That axiom resonates because saying no to things is incredibly hard. At the beginning, you never know what will be the key to making the whole company work, so there’s always a good case to keep projects going. In fact, saying no to something is the only, final way to ensure that that thing will never be the silver bullet. But saying no to the right things is perhaps the most important skill for a leader to develop.
The best foundational practice to develop that skill? Time-constraining your to-do list.
Here’s how you do it:
Weekly:
Create your weekly to-do list with ONLY the items you are confident you’ll have time to complete that week, leaving buffer room for shit that comes up. If you’re unsure you’ll have time to get that thing done, it CANNOT be on the list for that week.
Daily:
Create a daily to-do list the same way. The only things allowed are the things you will create time to address that day. Any uncertainty as to whether you’ll have time, the item must be removed from today’s list. Working on something too big to fit in a day? Chunk it down.
This practice does two things, both of which are wonderful.
First, it forces you to prioritize everything that you have going on, and to practice saying no to worthwhile things. This is the muscle you need to develop to be able to confidently and skillfully say no to larger things as your company grows. This is the daily reps at 135lbs that build you up to the 250lb lift.
Second, this builds personal momentum by ending each day with a sense of accomplishment. A sense that you did what you needed to do that day, and of the work actually being done. An unfortunate side effect of “do more faster” is a large number of founders who are never finished with their work. At some point they just stop to sleep, if nothing else. You might get away with working until exhaustion every day in the early days, but scaling a company is a marathon, not a sprint.
As Oliver Burkeman person says in “Four Thousand Weeks: Time Management for Mortals” (which is an amazing book that you should read): "You'll do what you can, you won't do what you can't, and the tyrannical inner voice insisting that you must do everything is simply mistaken."
4. Pick a learning focus
“What you aim at determines what you see.” – Jordan B Peterson
If the first three practices are the engine of the vehicle that will take you from a founder to a CEO, then the fourth practice is the steering wheel.
If you’ve spent any amount of time in the business world, you’ve come across the saying “begin with the end in mind.” This idea, that developing a clear vision of what success would look like for your business is vitally important to achieving it, has been so effective for so long that it’s almost faded into the background of conventional wisdom on growing a business.
Perhaps because of this ubiquity in the strategic context, most leaders never think of applying this tenet to their own personal evolution, but it’s every bit as powerful in that context as well.
Consider two founders.
Founder A wants to level up into a CEO, so they read a bunch of books on CEOing and talk to mentors and generally work hard to do a good job.
Founder B also wants to level up, but instead starts by distilling their evolution into a series of practical transformations they’ll need to make to get where they want to go. They select the first of those (say: “become a strong delegator”), and apply themselves to a deep dive in that specific direction. Once they become a strong delegator, they move to the next focus area on their list.
Who do you think makes more progress?
Just like you can’t build an app without breaking it down into its component parts, you can’t build a leader without doing the same. And since every leader is a human being, with different skills and experiences, every path to transforming from a founder to a CEO is distinct. The most successful at navigating this transition do so by narrowing their focus to only one growth area at a time, and nailing it.
Here’s how to put this approach into practice:
Solicit feedback from those with whom you work closely about your strengths and weaknesses. You can hire some coaches to conduct a comprehensive 360 review, or I’ve written about a simplified way to do it yourself here.
Stack rank your areas for improvement based on impact and difficulty of implementation, and start with the biggest bang for your development buck.
Once you’ve determined your growth area (what Bob Kegan, adult development chair at Harvard calls your “One Big Thing”), share your focus on improving in that area with those you work with (especially those who participated in your 360), and ask for their support.
For example, tell your team that you’ve realized you must become a stronger delegator, and that you’ll be consciously looking for opportunities to practice. Ask them to alert you to opportunities to delegate more thoroughly, and to provide feedback at a set future date.
Solidifying a concrete goal for your personal growth, and then sharing that goal with those who will be impacted most by it, generates creative tension that pulls you toward success.
5. Self reflection
With an engine and a steering wheel, you’re well on your way. The last practice, deliberate self-reflection, functions like a GPS. It allows you to chart your location in relation to your goal, and adjust your heading based on real-time feedback.
When you’re training to lift 250lbs, your goal is clear and unchanging, and you can chart your progress toward that goal empirically. Every week you max out, and you see just how much farther you have to go. Evolving from a founder to a leader is harder, because the process is nonlinear and the outcome changes with context.
Sounds like building a startup, right? And just like building a startup, charting progress and reorienting around new data is critical. Just like successful projects include retrospectives – which allow the team involved to learn from their performance and do better the next time – successfully navigating the transition from founder to CEO includes intentionally observing oneself practicing new behaviors, and then iterating based on the results those new behaviors actually produce.
Again, there’s no one right framework to use in implementing a habit of self observation. The important thing is that you make a habit of doing it. Regularly. That said, once you’ve implemented the four tools above, the easiest structure I’ve found to begin intentionally conducting self observations is by dedicating a part of your morning journaling to self-reflection.
For example, you might have established that to get where you need to go, you need to become a better delegator. Great. That’s the current stage of your growth. Then each day, you’ll endeavor to delegate well, and the next morning during your morning journaling you’ll ask yourself how you did. Be brutally honest, with a focus on learning.
I’ve found these four questions to be illuminating:
In what situations did I have the opportunity to delegate?
Did I delegate well (whatever you’ve made “well” mean) in those situations?
What patterns do I notice about those situations and my reactions to them (actions/thoughts/emotions)?
How could I have handled those situations differently?
Self reflecting in this way does two things. First, nearly every session you’ll find new insights about your particular growth path that are different from anyone else’s, and you can iterate your approach based on those insights. It’s the build/measure/learn Lean Startup feedback loop applied to executive (ultimately human) development. And second, as you bring conscious attention to your behavior each morning, you train yourself to naturally bring attention to that same behavior throughout the day, creating opportunities in the moment to consciously practice new habits.
This sounds great, but I don’t have time for practice
I get it. Believe me. Growing a company takes a million hours per week and you’re already sacrificing hobbies and a social life. There’s just no way to fit in an hour of practice every morning (the amount of time it takes me to complete all these practices each day). Besides, isn’t spending all this time on myself just a bit selfish when the business has all these issues?
Short answer: no. Self care is not selfish. Self care is sharpening the saw.
Longer answer, if you’re so busy you don’t have time to invest in your own growth, you need to ask yourself if your response would be the same if your star employee came to you and asked for resources to invest in making himself more impactful. If so, you have bigger problems. If not, you’re falling into a really popular trap, but a painful trap nonetheless. Here’s how it works, from my previous work, Why We Struggle to Make the Leap (from founder to CEO):
I see this particular inconsistency of thought all the time in entrepreneurs, particularly those navigating the chasm between the resourceful startup founder and the CEO of a growth company (and mostly men, which might say something as well). We make very sane, logical, ROI-driven investments to grow every area of our company…except ourselves.
When it comes to our own professional development, we disregard the investment frameworks that we use (successfully) everywhere else, and underinvest in areas that would make us more effective, or make our job easier, out of a misguided expectation that we should simply be Superman. Rather than addressing our professional development needs as we would any other issue in the business — namely, solving for them — we believe that our shortcomings mean we’re not good enough in some core, primal way, so we can’t justify investing in our own development. Instead we need to simply “be better.” To not need the help in the first place.
As the founder and CEO of the organization, investing in yourself is the highest leverage thing you can do.
The importance of practice to developing as a leader
The person that builds a company from scratch is very rarely the same person who can scale that company to become a dominant player in its industry. The skills, instincts and temperament required for the former are often at odds with those required for the latter.
Successfully navigating this transition requires more than just adding leadership tools and techniques to a worldview fundamentally oriented to the hustle and chaos of early stage startups. The founder must change the way they think.
To make that kind of change, it’s not enough to simply know what to do. You have to practice. Intentionally. Every day.
Because that’s what separates the pros from the amateurs.