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Dear Founder,

If you opened this letter, you might be wondering if your company needs you anymore, or if you are making enough of an impact. Or, you may be crossing into a new stage of growth and it may be new or uncomfortable. Some of your new responsibilities may involve work that isn’t appealing to you.

The sense of being outgrown may be driven by a number of different factors.

Maybe you’ve started to feel as though you’re holding the organization back.

You notice decisions aren’t being reached, and you feel overwhelmed (re-read that letter!). Further, your direct reports, who may have more experience than you, seem to be getting antsy.

You’ve transitioned from managing an idea to managing a company. You may feel a little dislocation and wonder if you are up for this new challenge.

  • First, I firmly believe in founders. We should do everything we can to make founders successful. As long as they stay true to the vision and fully committed to showing up, being present and executing beautifully, it’s the best of all worlds. We’ve seen CEOs ousted or convinced to leave by ambitious direct reports, and it almost never proves to be in the company’s best interest. Particularly if this is your first time running a business, you should be using your direct reports as resources to help you to become the CEO they need you to be. Asking them for mentorship is a Judo move that helps you, gets them invested in your success, and recognizes their experience.
  • I’m also a big fan of coaching. The Valley is filled with former operators ready and willing to mentor leaders like you. I promise they’ve seen plenty of cases just like yours.
  • But becoming a great manager and leader can take time, and sometimes your business grows much faster than you can handle. That’s okay, too. If you feel you’ve exhausted options, the more you can gracefully lead through this, the better. Help select and onboard a new CEO, take on a new role closer to your passion and expertise, and step out of the way when necessary in order to keep the ship moving in a straight line. Check out “Becoming Steve Jobs” by Brent Schlender for a better retelling of Jobs’s journey from founding Apple, to stepping aside, to being ousted, to developing into the CEO we celebrate.

Maybe your organization is doing well and you wonder if you’re needed anymore.

In some cases, you may feel like you’ve done your job and now the team is operating effectively. You wonder what your unique contributions are.

  • I’ve felt the same thing before. When I was the head of technology at eBay, after a couple of years of hard work and after the crisis was over, we had things largely under control around the stability of the systems and around R&D. I was gone over the holidays with my family, and on the flight home I seriously wondered if the business could progress just fine without me. And then during our Monday morning staff meeting, we had a huge systems crisis. I quickly snapped out of it.
  • As much as you might not feel as needed as you were in the early startup days, you may be underestimating how inseparable you are from the business. Marc Benioff stepped aside as CEO very early at Salesforce. But he found out that in order for Salesforce to reach its destiny, he was needed to run it. Seventeen years later, he’s still delivering extraordinary value and impact and the Salesforce we know would be impossible to imagine without him.

Can you pinpoint the moment when you no longer felt needed? Is this coming from an external source or from you?

  • If it’s from you, what is the cause and is it solvable?
  • If it’s from an external source, what are you going to do next to gain skills, confidence, and buy-in from the team?
  • Can you rearrange your duties so that you spend more time on the things that energize you, and less on the things that aren’t soul food?

I firmly believe that founders should stay for as long as they can. They had the vision and idea for their companies, and they know better than anybody where these organizations are intended to go. The truth is, there’s no such thing as autopilot for a business. And as the founder of a company, you have the greatest ability to survey the landscape and continuously reassess what your business is and how it fits into the world. If things are running well, take pride in that. Now think about how you and the company can keep getting bigger and better.

We all can grow and adapt. Please think long and hard about what’s troubling you and why. Talk to someone about it. If ultimately you feel that you must leave, please do so with as much grace and dignity as possible. Take pride in all that you’ve accomplished to date.

But to be clear, we’d like to see you stay and keep making an enormous impact—it’s why we bet on you in the first place.

All the best,

Maynard