The Pros and Cons of Working Directly for the CEO

I remember the first time I worked directly for a CEO.  I’d reported to leaders before, and a VP before, but never the CEO.

It was also my first start-up job.  The start-up I joined had about 60 people and just 1 office, a big shared office like a fishbowl.  My desk was in there.  In one big open office in the center of the company sat the CEO, the President, the Controller, and as of my first day … me.  The four of us in that fishbowl.

It was quite a way to begin your first start-up job.  By being in that office with the CEO and President, almost every time the “door closed” for a conversation, I was in it.  I always asked if they wanted me to step out, but they almost always wanted me to stay.  I guess if it was a conversation they didn’t want me involved in, they could have met down the hall or in a conference room or at Starbucks or wherever.

And the intimacy of immediately being part of so many “CEO things” was fascinating, and enriching, and … weird.  They started to quickly trust me to do things outside of what I thought my job description was.  Quickly, I was called in to resolve a big issue with one member of the senior team that needed to be moved out.  I handled it, and learned a lot.  I was also quickly dragged into M&A offers, not just the transactional parts, but the strategic side.  “Jason, should we sell for $300 million?”  I didn’t even know I had a stake in that decision (vs just implementing it).

And then I remember the first time I sort of breached the implicit trust in reporting directly to the CEO and the founders.  I had a college roommate in town for a convention and we’d carefully planned a dinner together that evening.  We were good friends, and seeing him was important to me.  And that same deal, a big deal heated up.  And the CEO asked me to put together an important presentation for the deal.

I only had until 7pm to get that presentation done before the dinner with my old roommate.  I did a B+ job on the presentation, and gave it to the CEO by 8pm, while my friend had been waiting for an hour in the lobby.  The CEO looked at it, and knew it was B+ too.  He said I could do what I wanted, but this really wasn’t “up to my traditional standards.”

Boy — that hit me hard.  He was right.  It was a B+.  But it was 8pm, I hadn’t seen my old friend in years, and he’d been waiting in the lobby for over an hour.  Aren’t we entitled to a life? 🙂

I sent my friend home, and we had a crummy breakfast the next morning.  I finished the presentation, and made it an A.

Importantly, my CEO never criticized me or brought that up again.  But nor did he say much of a thank you.  It was an A, we knew it was an A, that it had to get done, and we moved on to the next A.

So … that’s a bit of a long story on How it’s Great Reporting to a CEO.  You learn so much, you get to be a stakeholder, your responsibilities and influence accelerate at an unprecedented rate.  But it’s also hard.  You don’t get credit for Best Efforts or Trying or Doing The Best You Could by 5pm.  You also don’t always get the kudos and appreciations you are used to.  You get them.  But not always how and where you are used to.

If it’s your first time reporting to a CEO, thicken your skin up a bit.  Expect to always have to deliver, even if it doesn’t always seem fair.  Expect to be appreciated, but not always where and where you need it.

And expect to be a partner.  Not an equal partner, but a partner of some sort.  Expect to advance faster, and grow more quickly.  And own more.  And be valued, for real (even if you don’t always get that pat on the back you were used to before). That’s what you deserve back.  If you’re up for it.

Published on August 4, 2020

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