Over Christmas, I read The Hard Thing About Hard Things by Ben Horowitz. My friend Todd Wade, an excellent Chief Information Security Officer, gave it to me for my birthday.
It's a warts-and-all account of how hard it is to be a CEO and the junk you have to deal with as part of the job. And you probably suck at it as everyone does.
There are many times his company is hanging by a thread and he has to make tough decisions to keep it alive. Horowitz nearly went bankrupt, had to lay off a third of his staff and rebuild. The book is him talking about the bits that actually keep you up at night, and he doesn't pretend there are clean answers.

As business owners and CEOs, you will almost certainly relate to this. I don't know about you, but I have met a lot of Executive Committee members on a diet of beta blockers and Zopiclone to keep anxiety at bay and sleep at night. It is not as easy as people think.
I have met a lot of Executive Committee members on a diet of beta blockers and Zopiclone to keep anxiety at bay and sleep at night. It is not as easy as people think.
I really like the way Horowitz masters the art of hard conversations and runs at difficult things. He categorises 'war-time' CEOs - the brawler, get-things-done fast-and-embrace-the-chaos type - and 'peace-time' CEOs - who bring hygiene, steadiness and longer-term ways of working.
(I'm sure you know both. Which one are you?)
I have seen many corporate friends step into their first CEO role and fail because it is just so different to any other thing they have faced.
Horowitz calls this out and says, you have to be kind of nuts to want to do it as there are no guarantees of success.
Firing People
There's a great section on how to fire someone.
"The reason you have to fire your head of marketing is not because he sucks; it's because you suck."
He says, if you're going to fire someone, make it a proper decision. Don't say "I think we've got to let you go." Too much wiggle room.
Make it a firm decision. Do it as early as you can or you'll regret it later.
But more than anything, be human.
If someone is surprised they're being let go, you've already failed. You failed to set expectations, failed to have the conversation when it might have made a difference, failed to act when you knew it wasn't working. The firing isn't the failure - everything that came before it was.
You do it yourself, ideally first thing in the morning so they're not sitting through a day of meetings wondering why you've blocked out time at 4pm. You tell them why, plainly, without scripts or corporate language designed to protect the company rather than respect the person.
Then you try to help them on their next move as much as possible. An introduction, a reference and a great story. Something that shows respect.
The rest of the team is watching to see how you handle it.
Most of the time someone has to go because you got it wrong and they are carrying your mistake.
Knowing that doesn't make the conversation easier but it should make you do it properly.
There's a line about how the wrong way to think about firing is "what's the best way to protect the company?" The right way is "what do I owe this person given that I'm about to take away their livelihood?"
If you run a company long enough, you'll face this so go and read it.
Dan
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