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Dreambuilding as a CEO

When I started managing about a decade ago I was terrible for the reasons many founders are: I’m my own biggest critic. I have extremely high expectations for myself, and as a result have high expectations for others. The frustration of incompetence blinded me from seeing the problem for what it was.

It took me years to learn that there’s a separation between the words you want to say and the words that get the job done. I realized humans are systems, and if someone isn’t performing, I needed to fix the root cause, not complain about the proximal issue. Also, while actions might be globally irrational, they are always locally rational to the actor. The employee thinks they’re doing the right thing.

Rage doesn’t work. What I learned does work (after years of trying) is curiosity. Curiosity about what caused the person to make a mistake.

It becomes interesting not just to understand the deeper issue, but to brainstorm how you might construct the most compelling reality for them. A CEO is like a dream architect in Inception, and your “IC work” is designing a thrilling environment for everyone to dream in.

A good prompt I use is just that – “How can I make this awesome for X?”. Try it next time instead of complaining. It works!


I’ve also swung in the opposite direction, constantly feeling insecure that – heaven forbid – an engineer might find their work boring for an hour or two.

While you do need to direct a movie for your team that’s broadly exciting, it does not need to be a Christopher Nolan $500M epic thriller. Even the CEO does boring work. Boring work is fine.

It took me a while to understand that I’m allowed to say things like “I need you to do X for me”. This is even ideal at certain moments. People want a leader that comports themselves with gravitas and authority. (These “sudo” moments have a certain cost to them. It shouldn’t be the majority of your interactions, but it certainly can be some.)

And if not, there is plenty of capable engineering talent around the world that will happily be paid to do the work. Silicon Valley, while mostly being a tremendously positive cultural exporter, has also bred a generation of talent that has an adversarial relationship with work. A cohort of developers that grew up with so much excess, it views work as something to do the bare minimum of, instead of take pride in. (I find these people very easy to screen for: they’re simply unhappy in general.)


If they aren’t performing, take a breath, quell the rage, and ask yourself “why”. And feel free to ask people to work if you employ them.