Principled Executives: Cryptids?
I have a half-dozen half-assed drafts spanning the seven years since One-on-ones are Mandatory.
That was a mistake. I have no shortage of lessons after I left Cerner (now Oracle, RIP) to join ngrok and later Rippling. But I wrote in private without finishing my drafts.
As I've grown, my bar for informative blogs skyrocketed. Why would I write a lesson that wasn't near earth-shattering? I had figured it out, surely you had too. That's the error, though: I often find lessons in the mundane.
Hell, today I'm unemployed by choice, riding a ferry to Seattle, and sitting on two offers. I'm lucky... and just generally lukewarm.
Is general disillusionment about opportunities the new phase of my career? Much like how an eager, early career Billy thought Ruby was the solution to every problem. Mid-career Billy sports a language denylist by problem space.
At the behest of a Rust recruiter and despite having plenty in flight, I took an additional meet-and-greet with an additional startup.
They're a small shop with a good product, delightful team, and a decent business. Their CTO did an interview where he was asked "what do you look for when hiring?"
What we value most is kindness. On one hand, it's because I think kindness is virtuous, but on the other hand, there are real benefits to it. When everyone on the team is operating in good faith, you can accomplish things you couldn’t otherwise. There are parts of the solution space you can’t explore unless people are all on the same page.
Kindness!
I haven't seen a picture of this man. Could be that any photos are questionably real.
Sharing core principles with leadership is uncommon. Somewhere in the ascension to the C-suite, perhaps on the profitability switchback, important principles can get lost. While this small shop is decent in every other dimension too, those all will change: business, team, product, etc.
Executive roles don't come with a self-growth feedback loop. What you see is what you get. Any leftover principles are then magnified and inflicted on the whole company.
When I worked at Rippling, our COO was Matt MacInnis. I respect the man a great deal; he generally has solid takes and is principled. He spoke on his framework in this interview at length.
I'm going to do him dirty here-- it's impossible to succinctly capture seventy minutes of nuance in a quote. Below, MacInnis is a few layers deep, discussing what I've coined "leadership harm reduction" when making decisions at a rocketship startup:
This sort of takes me to a framework that I use as an executive. You will never get it right. And when I say it, I mean, literally anything you can think of. Will I get this executive's compensation exactly, right? You know, will I staff this team against this project exactly right? Yeah, the answer is like, no, I won't get it exactly right.
I'll be wrong in some direction all the time. And the question you have to ask is like, is it better to be wrong in this direction or in that direction?
[...]
So all of our teams at Rippling are pretty deliberately understaffed, and people feel it, and they'll complain about resourcing, but like, at the end of the day, a team of five that ought to be seven, uh, is way better than a team of nine or 10 that ought to be seven.
I too felt the understaffing squeeze at Rippling. I was one of the people who complained about it over two years. And I largely agree with this take too: given too many or too few people, I'll take the latter.
MacInnis is wrong on this one. I'm sure he'd agree, given the framework.
A year ago, Natasha Jarus and I were returning from a gelato run. She was rocking some new knee-high platform boots on a wet, dark Seattle winter night. Fortunately for her, she had driven us there.
Unfortunately for Natasha, her new 1980's truck had been boxed in while parallel parked on a steep hill. I should also mention it was a manual and didn't have power steering.
I had the joy of watching her attempt to reverse out in those platform boots, using all four limbs. While she moved the tires with great effort, I gleefully acknowledged how ridiculous the situation was; she'd stacked most of these constraints up all on her own. Natasha agreed with me!
She succeeded despite her self-imposed extenuating circumstances.
Natasha could drive an automatic modern car with normal shoes.
MacInnis could staff his teams, getting it right on average and adjusting dynamically.
I could finish a mundane blog post.
- Previous: One-on-Ones Are Mandatory