Thoughts for founders
This is a redacted email I sent to a first-time founder grappling with difficult feedback from his team.
First things first: your work is not your worth. Your company does not define you. Whether it succeeds or fails does not mean you are good or bad.
It’s important to diversify your identity. Most founders’ identities are deeply enmeshed with their companies. It makes sense: it’s the reason founders achieve the seemingly impossible. But perverse things can happen if your company starts to swallow up your identity, from stress and anxiety to less effectiveness across the team, to more serious issues.
The only antidotes I know of are 1) intentionally building up the other parts of your identity by investing in relationships and interests outside of work, and 2) regularly getting distance from your company—physically, mentally and emotionally—on various intervals (daily, weekly, monthly, quarterly).
This might seem counterintuitive, but most founders I know find that they come back more energized and with fresh, useful perspectives on the business.
No one will ever be as obsessed about your company as you. I’ve seen many founders struggle until they accept this. They lament that no one works as hard as they do or even cares as much as they do.
The vision, will and grit needed to bring a company into the world makes it an extension of you. Founders are the only ones who think about its vision, the abstract story of what it means in the world and where it’s going (read more here). It’s not realistic to expect others to experience it in the same way.
Once you can accept that a company is a collection of people with different life experiences, personalities, skills and personal dreams working together to create something, and that it’s not necessary for everyone to feel the exact way you do about your company, things might get easier.
You are not responsible for anyone’s emotions other than your own. This one is big. You are only responsible for your actions and the meaning you attach to things.
Another person’s happiness is not something you control. And striving for 100% happiness across a group of people is a recipe for disaster. You can do things that communicate a concern for someone’s well-being and happiness, and even if your intention is there sometimes your actions won’t have the impact you want. How someone interprets your actions is up to them.
Meaning > happiness. Happiness is a shitty goal to strive for (see hedonic treadmill). It’s well documented that we adjust to things we think will make us happy—perks, promotions, purchases. Meaning or purpose—creating something bigger than yourself, being in community and serving others etc—is far more powerful. By definition there are challenges along the way. People find meaning in different ways and one part of leadership is uncovering individual “recipes” and aligning them in the direction of the company’s vision.
Investigate your own reactions. Just as you can’t ensure 100% happiness for everyone on your team, you will never be all things to all people. As the company grows, this will become even more true.
However, it’s worth delving into what it means to you to be well-liked. How do you know when you’re well-liked? Why is it important? Longer topic, but this is where a therapist or coach can really help.
Notice the stories and learn to reframe. You choose how you interpret feedback; it’s just data. Our language is rife with distortions, deletions and generalizations — as humans, we need to do this in order to function efficiently. But this creates all sorts of communication problems. Notice how you talk about your concerns, about your employees and about yourself. When you reference “the problem”, practice asking yourself “what is the problem, specifically?” When you say, “I should do this…",” ask “according to whom?” These are all useful ways to examine the validity of knee-jerk thoughts and consider other possibilities.
Feelings are not facts. Any statement starting with, “I feel like…” indicates a thought, not a feeling. Most likely, it’s is a story you’re telling yourself. Our emotions, especially in the moment, very often lead us astray—so taking a step back to actually assess what’s happening with a clear head and facts is important. (Also: ask “so what?” if someone prefers you weren’t CEO? If you keep asking this question, like the “5 whys,” you may end up uncovering a belief that may not be serving you well).
Develop empathy. Remember that there is no reality, only how we each interpret it through our unique lens. One useful mental model is to assume positive intent in others, including your team. Try to see the world through their eyes and understand that if you were in their shoes (I mean, having had their upbringing and experiences and personality etc), you might act the same way.
This post by Daniel Gross touches on how seeing the world through an employee’s eyes helps you move the company forward.
Care and accountability are not mutually exclusive. Some founders have the opposite of the “asshole” situation: they think of the team as a family and care a lot about people—to the point where it can hurt the company. They struggle to have direct conversations about performance and to hold people accountable to results.
Balancing the two is what leadership is ultimately about. Radical Candor is one well-known framework for this. And since companies are just collections of individuals, the same tension between care and accountability manifests as a tension between the “how” of culture and the “what” of performance (more on culture later).
Understanding ≠ agreement. Strive to become curious and learn to really listen. Why do certain people appear pessimistic and negative? Where are they coming from? You can listen to someone on the team and validate their experience/feelings without agreeing with the content of their idea or argument. It might feel difficult to do at first; listening with the intent to understand, not interrupting and correcting etc—this doesn’t come naturally to the vast majority of humans.
Making the other person feel heard is a superpower. This is one of the most useful articles I’ve read on this topic, and Nonviolent Communication is one of my favorite practical books.
Culture is not stuff. Some founders view culture is an output or a prize for achieving performance. The reality is that you already have a culture. Every organization does. It comprises the behaviors you reward. Many founders are unintentional about what they incentivize vs. discourage.
As I mentioned above, you may find that demonstrating care for your team, rather than adding perks, can unblock a lot because it hits on a more fundamental need than yoga or salads ever can.
Your role will be the loneliest. No one will ever have the picture that you do. CEO roles are notoriously lonely because you have more people and information to deal with than anyone else. You have the power and the responsibility. There will always be information you can’t disclose to others, sometimes even your co-founder.
This is why developing close, trusted relationships with other founder-CEOs is critical. Often they’re the only ones who will really understand what you’re going through.
But realize that you will also never have the unique perspective, experiences and personality that any one person on your team does. And remember that everyone is experiencing their own difficult stuff, whether at home or at work or with health or something else.
Finally you need to decide what is important to you: seeking truth? Being right? Develop the skills to notice when you are reacting from fear or anger and straying from your ultimate objectives. This is just human nature: everyone is wired this way, and it’s a lifelong process to manage.
Leadership is learned on the job. We can read all the theoretical stuff we want about how to manage and lead, but putting it into practice is a different thing entirely. First-time founder-CEOs are forced to figure this out as they go. You will make mistakes, that’s inevitable. What matters is whether you develop the capacity to reflect on them, seek other perspectives, no matter how difficult they might be to hear, and evolve in the direction of your values. Again, you will find that every other founder-CEO has learned many interpersonal lessons the hard way. Hopefully, this reminds you that you are not broken nor alone in what you’re going through.
I’ll end with one of the best threads I’ve ever seen on being a first-time, venture-backed founder/CEO: