How to Prepare Yourself to Be a Great CEO

Being a founder is easy.  You just start something.  Grab a smart friend, hop on over to WeWork, hit 99 Designs for the logo, and you’re off to the races.

hugeofficeBeing a CEO is tough.  You have to convince people to join you.  To drag the troops up the hill.  To invest in you when there’s no logical reason to.  To do the impossible.  You probably haven’t done it before.

Turns out, first-time CEOs are often the most successful.  Because they don’t know it’s impossible.

But they are often just awful managers.  Or at least, far worse than they are the second time.  This means more employee churn, friction, drama than you need.

You’ll grow faster, with less stress, and more success, if you’re a better CEO earlier in your career.  Especially in SaaS.  Because SaaS is so cross-functional.

And it turns out, you can train now to be a better CEO when the time comes.

To help, my top 5 suggestions for CEOs-in-waiting.

  • Manage People.  This is one of the best things you can do, because 50% of the job of a CEO is recruiting a team, leading a team, empowering a team, convincing a team.  This team will include investors, the public, press, PR, etc. — but it’s all a team.  Manage anyone you can, even if it’s not perfect.  My first management job was managing HR.  I didn’t want to learn HR as a function, I turned it down at first.  And then I realized I was wrong, apologized, and went back and took the reports.  I was lucky I got the opportunity.
  • Work for The Best One You Can.  This may be obvious, but try to do this at least once if you can.  The best way to do this is to join the management team of the best start-up that will have you.  Even if you get topped 12-24 months down the road, it’s worth it to have reported to (and thus worked directly with) the best CEO you can.
  • Try to Care More About People.  And Show It.   This is one of the top mistakes I see in first-time CEOs.  They care so much about the company, but they forget to care about the people, the team.  They just assume everyone should be as committed as they are.  But everyone else can’t be.  You aren’t going to double your EQ overnight.  But try a few things.  Say “Thank You” more often.  Give raises more often.  Give spot bonuses more often.  Give 20% more shares to your top 10% employees, without them asking.  Take the team on outings.  Do a retreat for the whole company when you hit $5m ARR.  Do stuff together.  Do dinners.  Stay late with the sales team when they’re trying to close the last deals of the quarter, and take ’em out for drinks after.  Do it all.  Again — if nothing else — SAY THANK YOU!
  • Hire People Better Than You (and That Aren’t Your Friends).  Whatever you do, don’t hire executives that aren’t better than you.  You can hire up-and-comers, that’s OK.  But as CEO the key is everyone on the team should be better than you if possible.  This isn’t a threat.  It’s a way to make your equity worth 100x more.  Before you are a CEO yourself, experiment here.  Don’t just hire your friends, and don’t hire people that make you look good.  Hire people materially better than you, and that look, act and feel different. But that you 100% believe in.  Amazing things will happen.  You will learn so much here.

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There are 9 comments

  1. John Saddington

    Getting a “coach” or “trainer” is so critical… how often we confuse these with “board members” or just friends. The top-performing athletes have them… we should have them in business (and in life)!

    Love that.

  2. Bushair

    Great Jason. I always like your approach in briefing.
    Meanwhile, you missed spreading vision and culture without delegation? Even if we have best team, if CEO is not in charge, I think the culture collapse.

    1. Jason Lemkin

      No. You can train yourself to be extroverted where necessary. It’s like public speaking. Every CEO ends up being a pretty good public speaker, even if they start off scared as heck and terrible at it.

  3. Jason Evanish


    I’m surprised you didn’t mention 1 on 1s when you talked about caring about people, especially since you’ve written about it before. It’s amazing how often little problems can blow up over time all because they’re not getting talked about and fixed. Employee happiness and satisfaction is a moving target and many seem to overlook the need to spend time on a 1 on 1 basis to address it.

    I spoke to a CEO of a Valley startup a few months ago and he mentioned he had to keep giving his best people raises so they won’t quit; turns out, he rarely checked in with them and then by the time they came to him they either were already interviewing for other jobs or threatening to (which is another thing you wrote about).


    1. Jason Lemkin

      Yeah 1-on-1s are super important — super important — just one level of detail down from this post. Agreed it’s something to 100% learn and practice to train to be a great CEO.

  4. Jai Rawat

    Great post. Having been part of the startup eco-system for a while, I would say #4 (Try to Care More About People) is the what get ignored most often. A little care goes a long way. We had recently invited Jack Welch as a keynote speaker for a conference and interestingly this was one of his top points as well ! Truly care about your employees and help them become rock stars.

    1. Guillaume Lerouge

      Agreed. It’s just so easy to assume that everyone will be (or even worse, should be!) as motivated as you are. Taking time to thank and acknowledge their success will go a long way towards building successful long-term relationships, faith in the company and happiness from the team.

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