Open Letter to First-time ...


Dear First-time CEO of a Startup,

I know it’s intoxicating.

Take a breath.

Maybe you’re 26 with a killer idea that melts Facebook- and Yelp-like functionality into a travel app. Or you’re 40ish and finally – after shelling out a fortune for that MBA with the promise of a career catapult – getting the chance to run the show.

It’s doesn’t matter how you got here.

You’re here.


Now let’s get down to business.

You’re about to do the one thing that will sabotage your company and retard personal growth. You’re about to do everything humanly possible to show your employees, consultants and anyone, for that matter, who crosses your path that you are NOT a first-time CEO.

You can say it. You’re feeling pangs of insecurity. It’s OK. This is just between you, me and whomever reads my blog (trust me, it’s a modest audience).

Absent a Ph.D. in psychology, I turn to the line from the original Shrek when he comes upon Lord Farquaad’s castle: “Do you think he’s compensating for anything?”

All of those wonderful leadership qualities that prompted the Board to pick you reconfigure themselves into a case of acute micro management.

Of course, you recognize the intellectual argument for empowerment. But you’ve concluded that you can achieve “the best of the both worlds”: pretend to listen and pretend your team has a say, yet still end up being the one calling the shots down to whether the Zen master comes to the office on Wednesday or Thursday.

You’re not fooling anyone. Your team will discern a pattern in which its judgments align with decisions only when you’re in agreement. This triggers commiseration giving way to backbiting and attrition. You’ll rationalize departures as “not being a good fit” with the insinuation being they weren’t smart enough or couldn’t handle the pace or both.

To be plugged into the minutia of the company, you ask your management team to copy you on emails. Your explanation – “The work is mission-critical. By understanding what’s going on, I can better support you.” Nice try. Your team will perceive this for what it is: a lack of trust.

You can invest hundreds of hours in studying successful CEOs. Allow me to save you some time. Nothing inspires like the simple act of trust. Not just trusting others to make decisions, but doing what you can to help make those very decisions a success. That’s part of leadership. And you suffocate others’ desire to go above and beyond when you don’t trust.

Perhaps the most visible manifestation of the I-am-not-a-first-time-CEO act will come during your executive management team reviews. The only thing missing from what resembles an interrogation is the single light bulb, no shade, dangling from above. Machine gunning questions at each executive to supposedly uncover weakness – and reveal your “brilliance” in that particular executive’s domain – does not advance the cause.

You may have absorbed the Walter Isaacson biography on Steve Jobs as a form of finishing school for CEOships. It’s not. As a general rule of thumb, being an asshole to others hurts your ability to lead.

Look, you can still be tough. To push for the extraordinary is the only way a startup can dislodge the status quo.

You just don’t have to be a jerk.

And it’s OK to periodically let people in, to show them the real you.

They won’t think less of you.

Actually, just the opposite happens.

People will run through walls for you.

Note: Obviously, not every first-time CEO falls into this trap. Still, I’ve seen a pattern over the years which prompted this post.


  • Dude

    “Madden is on the field. He wants to know if it’s real. They said yes, get your big butt out of here! He does!”
    — Bill King

    The best jockeys have a light touch on the reins.”
    — Anon

    “Nothing is more effective than sincere, accurate praise, and nothing is more lame than a cookie-cutter compliment.”

    “You have to be very sure of yourself. You have to be able to say, look, there’s a risk here and we’re willing to accept the risk. If it doesn’t work, it’s just part of doing business.”
    — Bill Walsh

    The challenge for CEOs (founder, first-timer, or even turnaround positions), is that in most cases, they don’t know what they don’t know.

    The trick, to use a football metaphor, is to be a Bill Walsh-style head coach, and let the experts manage and the players (workers) get the job done. Take the blame for the losses. Criticize privately — unless a public admonishment is warranted (rarely if ever). Prepare methodically — even for the challenging situations — and teach others that level of preparation.

    Show passion for your solution, but be realistic. Nobody likes or believes a BSer. Give credit when and where it’s due. Lots of it. If your choice is being cheap or being solid, what do you think people (and the Internet) will remember? Nobody cares how fast you got it done. Only how good it is.

    If you think tweeting and (anti-) social media is going to sell your products. Think again. Nothing works better than solid PR/Marketing “Blocking and Tackling.”

    And, except for warmups and after the gun sounds, get your big butt off the field.

    (Watch the “Holy Roller” play here:

    • hoffman

      Incredible list.

      Love it!

      I think this one goes to the top of the list:

      “Nothing is more effective than sincere, accurate praise, and nothing is more lame than a cookie-cutter compliment.”



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