Surviving being senior (tech) management.

As a CTO one of the most consistently challenging responsibilities to feel like I was doing well was supporting the senior leaders who reported to me. They were universally high performing people, with difficult jobs, who cared passionately about their teams and outcomes. We spent plenty of time talking tactics and strategy, technology, and management, but one topic that was always key, was self care. The topic is infinitely varied, but it got to the point that I had some standard advice I gave, and this is it.

Being an engineering leader is different

  • Senior management is a job where your ability to cope with your demons is critical to the success of everyone who works for you. Ben Horowitz writes about this in, “What’s The Most Difficult CEO Skill? Managing Your Own Psychology”
  • Most people doing the work (at least in tech) are transitioning from maker to manager, and while a few special people are both good at management and enjoy it (and also a few sociopaths), most of us find it a difficult transition: rewarding but also filled with doubts and uncertainty.

Some Advice

1. Get some exercise

2. Have someone to talk to

It can be a coach, a therapist, a good friend, potentially a very patient and saintly spouse (not recommended). Ongoing, trusted and good at listening are the characteristic you’re looking for.

3. Talk with peers

What you’ll find out is everything is fucked up everywhere. And you’ll feel better about your own job. Your problems suck, but boy are you super glad you don’t have their problems. And they’ll feel the same way about you, and your problems.

Perspective is the thin line between a challenging but manageable problem, and chittering balled up in the corner.

4. Have a personal mastery project

You’re almost certainly doing it for the wrong reason. Cut it the fuck out.

There are lots of good reason to stay close to the day to day work (including, but not limited to, you’re an early stage startup, and everybody has to pitch in), and even more failure modes in that directions. But none of those good reasons are about you feeling better, or more in control, or like you “did something real”. You’ve got a real job, it’s called being a leader.

But that doesn’t mean the need you felt to learn, grow, acquire new skills, and generally stretch yourself that were hopefully key traits to getting you this far just go away. Or that the sometimes maddeningly elusive accomplishments of making your team better can be swapped in for that personal satisfaction. For that you need a personal mastery project. Something, quite probably not related to work, where you can prove to yourself that you aren’t actually getting dumber every day (just older), and can still think, reason, and learn.

A side coding project might be it. Or learning a (human) language, taking a class, practicing classical piano. Something. Something that stretches you, and you can master. By yourself.

Put your own oxygen mask on first, before assisting others

You aren’t useful to anyone if you aren’t taking care of yourself. There is an unbound set of things you could be doing better in order to help insure the success of your team. That set will constantly expand to fill up all the time. The most important thing you need to be doing is making sure your own oxygen mask is on first.

(I also have been writing on this topic, and other topics for the last 15 years over at my personal blog)

Onward. Previously SVP at Blink Health, CTO at Etsy, Flickr Architect. Interested in engineering positive change.

Onward. Previously SVP at Blink Health, CTO at Etsy, Flickr Architect. Interested in engineering positive change.