I’ve been a founder and ceo for the last 16 years. Almost all of it self taught.

Over that time I’ve come to believe that founders can become great ceos. The only way to get there is by doing it. Yes you can get a coach but that only takes you so far. At the end of the day you need time on the field making decisions, fucking up, and learning from your mistakes.

What makes this transition hard is it takes time. You acquire the hard skills by running enough companies with enough varying scenarios that you can build recognition patterns. The soft skills develop by leading people and making a lot of personal mistakes, many of them causing additional emotional stress. All of this often takes more time than your current startup wants to give you.

You see a similar development happen with sports coaches. First time head coaches often fail, get fired, and connect the dots in their next head coaching role. Even Bill Belichick, the most successful NFL coach of all time, went from being a hugely successful assistant to a failed head coach tp a record setting head coach. He just needed more time and more chances to learn how to be great.

Back to startups.

The intensity to start a company is so great that people don’t do it for decades. They do it long enough to succeed or fail and then they stop founding because it’s too hard. The end result is a network of fellow founders who can share broad learnings, but who haven’t has the time to create their own methodology on developing from a founder to a ceo.

So I collected feedback from several who have made this transition and combined it with my own 16 years of making this transition. If I were to develop a founder into a CEO here is how I’d think about it.

Development Triangle

I think of developing from a founder to a CEO like this….

• Self – the personal foundation you need, no different than if you are trying to become a professional athlete.
• People – the people skills, without them no one will follow you.
• Functional – the functional skills, these are specific to your market and business model.

The assumption is that you already have the personal foundation in place before you take the role. Developing all three parts of the triangle at the same time is really difficult.

Time

The overall thread to developing as a ceo is this transition takes time and energy. It’s not for everyone.

An alternative path is focusing on how to be a great founder. Understanding customer needs, building products that gain traction, and willing people to believe are very hard skills to master. You then have to get great at finding and hiring the right ceo to take it from a product to a company. Garrett Camp is a modern day version of being a successful founder, starting StumbleUpon, Uber, and Expa. I haven’t met Garrett but from the outside it appears he’s obsessed about founding new ideas and teams.

I provide this context so people understand there is no shame in just being an awesome founder. To found, start, and hand off companies can be personally rewarding and financially lucrative (i.e. Garrett is a billionaire).

If you do want to be a great ceo you have to recognize this is a life’s work. You will need your founding ideas to be successful enough that you can learn to be a ceo or you’ll need to join fledging product ideas that need a ceo. You’ll also have to be wiling to try it again if you fail the first time.

The Self

Being a ceo is a long game. It takes time to develop a company and even longer to develop your ceo philosophy. Therefore I believe in foundational building blocks that you will need to stay committed over the long term.

1. Discipline
Cus D’amato was Mike Tyson’s coach. His philosophy was that will is more important than skill. You aren’t born with skill therefore you have to practice and train to become the best.

This only happens with discipline. And no one can generate this for you. You have to find it and harness it until discipline becomes a personal habit.

Mine started as a kid with soccer. I wasn’t always the fastest therefore I had to be the hardest worker. I’d train before school, after school, and then go to team practice. Fortunately this created a set of habits that I now heavily rely upon.

It’s important to note that with discipline it doesn’t mean that you can’t be creative. I find the opposite to be true in that the more disciplined you have the better your creative sessions become. You create with purpose that keeps you from getting burned out.

2. Physical Exercise
This is hard to do consistently. It becomes easy with stress and travel to ignore how exercise is tied to your very survival. But it is.

Consistent physical exercise is very much tied to your discipline so find a way to make it foundational to your life.

3. Emotional Outlet
You are going to need a place, or person, or a set of people that become your emotional outlet. You should recognize this before you even start.

If you are founding a company and have a significant other, they are also founding the company with you. You should talk about the why behind founding the company and what success looks like for the two of you. And you’ll have to keep this conversation going as you level up in the ceo game. Each new level gets harder than the previous one and without the emotional support you will break.

A therapist is also a good way to go. The role is stressful, especially when it’s not going well. Money and expectations are a heavy burden to bear.

Another route is a psychology coach. Ideally you can find a coach who actually develops ceo (ie has been a founder to ceo). Unfortunately the startup industry is full of “coaches,” ie people who listen really well but haven’t been a ceo.

The People Skills

Leading people is emotionally difficult. It’s even harder if you don’t have a methodology for how you organize and run your teams. The analogy would be like coaching a sports team but not having any method for how you prefer to practice, prepare for games, play the games, and analyze the results.

Giving people the structure they need is critical to reducing the emotional stress involved. It’s better to start with something and modify it over time than to start with nothing.

1. Compensation Philosophy
How you pay people matters. Are you going with the traditional negotiated model (hiring manager versus the employee) or are you going with a formula model?

I have moved to a formula model, emulated from Buffer’s salaries.

I have found that a formula model removes a lot of the emotion around hiring, especially ‘renegotiating’ when people leave. It treats everyone the same so the team can focus on the work and not try to figure out why someone is making more than them.

Your compensation philosophy speaks to how you think about the people on the team.

2. Team Structure
You should have a way you like to organize and run teams. This includes the when (daily, weekly, monthly, etc) and the how (functional vs non-functional).

In sports this is similar to having a consistent schedule and a formation by which you play the game. Both of these threads can change over time as the team becomes more sophisticated.

By having a preferred structure you give people clarity on when to work and who owns what. This helps people focus on the work and not be distracted by hierarchies.

3. Feedback
You have to develop how people give feedback within the company. This is both at a peer and structural level.

The biggest challenge in developing feedback is that people are terrible at it within a business environment. This is because no one has taught them how to give and receive feedback. Plus they haven’t learned what kind of feedback they need through out a project. The feedback you need at the problem definition stage is very different from the shipping stage.

Beyond the day to day level of feedback you also have to establish the formal process for feedback, both when and how. This gives people the stability they need in knowing how they are doing at their job.

4. Taking Teams Apart
Unfortunately learning how to put teams together also means that you need to learn to take them apart. This can be at an individual level (moving or changing people) or at a team level (layoffs).

The best resource I have read is Ben Horowitz and The Hard Thing About Hard Things.

Anything Ben puts down on this subject is worth picking up.

The Functional Skills

Many of the functional ceo skills you need are business model and market specific. Most of them are developed by fucking up before learning the right approach.

The nice things is these functional skills get easier over time.

1. Editing
Editing is the most important skill you have to develop.

As a founder you write, but as a ceo you edit. This means being able to listen, cut to the core, and then pull out the key insights. It doesn’t matter if it’s a product, customer, or team issue you have to learn how to cut to the core problem and communicate it.

I use a few tools to learn how to edit…

• Customer Journey – it’s a mental map of before, during, and after. It helps you quickly map out process to understand the core problems. It’ helps you to identify what you don’t understand.

• Visual Hierarchy – a core element to design thinking, it stresses that arrangement of information implies importance. Getting good at this helps you structure the most important information up front with the problem, the why, and the what.

• Skimming – if you can skim and still understand it then the information is well organized. You can’t skim everything but it’s a skill set that helps you to focus on what is most important. If something is too complicated to skim then something is wrong.

• Malcolm Gladwell – he is incredibly succinct. Reading and listening to his podcasts you can learn from someone that is able to distill complex topics in simple ways. If not Malcolm find other communicators who you believe are great editors.

2. Communicating
What you say matters. Learning this is painful as you transition from the early days (everyone personally knows you) to the later days (very few people know you). People will start reading everything you do and making assumptions.

The energy you bring. What you say. When you say it. Even who you say it to and in what order. It becomes overwhelming to worry about.

Communicating is harder when you are wearing multiple hats. Especially as you build out a leadership team, there are times when you will hold dual roles and people will struggle to understand if you are speaking as the ceo or as the functional leader. It’s your job to clarify.

What people want is…

• Consistency. They don’t like all your new ideas or changes to plans they already executed.
• Clarity. They need you to be succinct and to the point so they can make decisions from what you say.
• Confidence. Being calm throughout the peaks and valleys gives people the confidence that they are making the right decisions.
• Transparency. Don’t underestimate the decisions people will make if they have the same information you do. I’ve always found that if you are totally transparent and provide clarity around the why, people will follow you. When you start hiding stuff people will bounce.

3. How You Win
You have to figure out what quadrant you can own in the market. This skill takes practice in looking at how the market traditionally competes without you and how you can win on a new paradigm. I call this finding your quadrant.

You learn to do this at a product level (i.e. how you differentiate) and at a business level (i.e. how do we win the market). From this clarity you then learn how to communicate and adjust resources to execute against your opportunity.

4. Decision Making
You have to learn how to make ceo decisions. Keith has a decision framework I agree with. It’s based on your level of confidence and the impact of getting the decision wrong.

As your company scales you move from lots of small decisions to a few, very large decisions. These become the decisions that keep you up at night.

The learning skill here is to figure out which decisions you need to make and which ones you don’t. The less you can make and and still deliver, the better.

5. Have Capital It’s your job to make sure the team has the money it needs to execute their plan. This can come from debt, equity, or by being profitable. It’s on you to pick the right strategy and then find the right partners.

Finding the right partners gives you rocket fuel. While finding the wrong partners is death by a thousand cuts.

The skill set to master is story and investor speak. Learning how to simplify your business and then find people who are excited about the title wave you are trying to ride.

Conclusion

This is a work in progress as I develop my own philosophies on making this transition. A lot of what I have learned has come through struggle. It’s a struggle I love and try to get better at every day.

If you need anything please dm me @marcbarros.