Founder to CEO: Mastering the Unnatural

by Tim Henningsen on January 21, 2013

You are the CEO of your life, always have been. But now you have started a company. What will you do? I’ve seen a lot of founders the last several months as an entrepreneur — different styles, different strategies — and have tried to gauge how they would be as CEOs of their growing companies.

Two recent blog posts caught my attention on this topic which I’ll discuss further below. Their themes are very similar and share a common thread. You’ve got a shot at finding your legs as a founder-turned-CEO if you can master the art of taking great comfort in what typically feels unnatural to you. And then training those existential muscles for maximum, long-term effectiveness.

“Learning to make this unnatural motion feel natural takes a great deal of practice. If you do what feels most natural as a CEO, then you may also get knocked cold.” — via Ben’s Blog

Here are three “natural” tendencies I’ve seen that leaders should learn to check at the door, when it just feels oh-so-right not to.


This is a big one. It’s never done, EVER. So don’t beat yourself up trying to craft the perfect pitch or build the perfect product. You do better without notes? Be yourself and tell a good story. You’re a lean startup? Ship the beef and iterate.

I led a team of front-end web developers back in the days of the browser wars. This was when IE5 and 6 were battling it out with Netscape 4 and 6 (5 was scrapped!) for the top spot. We had lots of time and money to perfect different ways of slinging CSS and pushing pixels depending who was visiting our sites. We also spent an inordinate amount of time accommodating a bunch of browsers hardly anybody was still using. Supporting these third-world browsers just held up the business from pushing the limits for our customers and partners.

Today this would be like holding up your mobile strategy because, even though iOS is ready to ship, burning development cycles on every flavor of Android still feels like the natural thing to do. Always be thinking Big Picture.


In his blog, Ben Horowitz of Andreessen Horowitz writes about being authentic. “Be authentic. It’s extremely important that you believe in the feedback that you give and not say anything to manipulate the recipient’s feelings. You can’t fake the funk.” What Ben is referring to here is the proverbial “Shit Sandwich” most managers have been taught to serve their employees. I’ve had this feeling on both ends. Whenever I hear it now (or am tempted to prepare the sandwich for somebody else) it feels like nails on chalkboard.

When you’re stuck on a 24×7 all-expenses-paid placation with your team, instead of providing direct and useful feedback, you’re hosed. There’s no forward motion anymore. It might feel right at the time, but even your youngest talent are picking up the subtle vibe. You also risk keeping people around (including yourself) that would rather play a game of culture poker than move the culture forward. Lay your cards on the table. Always be Authentic.


In his blog, Mark Suster of GRP Partners writes about thinking vs. doing and how entrepreneurs don’t think enough.

“Stop planning while you’re doing. Start planning while you’re thinking.” — Both Sides of the Table

It feels natural to always be planning, especially if you’ve had the axiom “failing to plan is planning to fail” beaten into your head. Having a plan is essential to execution. But I think Mark’s point here is don’t let planning get in the way when you’re busy doing. Instead, start doing more planning when you’re focused on thinking — well ahead of the doing.

You need to be thinking about the unthinkable, ALL the time. This is unnatural for most people. CEOs should “do one other job, exactly one other job…” For most companies, that’s probably product or sales. If you’re fortunate to have a trusted and talented product or sales executive at your side, then consider becoming Chief Contingency Officer — think and plan for the stuff your employees don’t have time to think about. Share it with your team. If the moment ever strikes, your company is ready with a swift response. Always be Built for Speed.

Tim HenningsenAbout the Author
Tim is a technology business developer based in Silicon Prairie, USA. He is co-founder of SquareOffs, and blogs with soul at Follow him @gimmetim on Twitter.



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