How I...
Want to understand how I approach problems? How I learn new things?
How I... is the place for you! There are the posts where I explain how I do what I do.
These techniques work for me. You do you.
A question I often get from direct reports is roughly:
I watch you set people up to take action on their own, even if it seems like they’re going to fail. I want to get better at this as a manager, how do I do it?
I love this question because it’s a critical moment of growth for all managers and leaders. As we have (hopefully) all learned from Andy Grove, your impact as a manager is the total of your impact plus the total of all your reports, and in my experience, there’s no stronger way to help teams succeed than being comfortable with potential failure.
I used to be terrible at this. Early on at Linden I would solve problems by working all-nighters, writing initial implementations with bullshit passive-aggressive names (‘StupidSpaceServer’ was a classic.) Fortunately, I was lucky to work with and for a series of great leaders like Philip and Schrep who — in the very best of ways — gave me no end of rope to hang myself with but who would then react to failure not with anger or frustration but with an immediate desire to celebrate what we had learned. It didn’t really click until Facebook, but once it did I was a far more effective manager and leader.
I wish I could point to the first time I did it, but as long as I can remember I’ve had a habit when faced with an either-or choice:
Go for a run or lift?
Hiroshima- or Osaka-style okonomiyaki?
Should we build it fast or reliably?
Why not both?
It’s been my experience that in most situations, when someone presents an either-or decision, the most useful way to understand the decision is to imagine how you would do both. Experience both. Try both.
It might be too costly or time consuming. You might not have the resources or expertise.
Or, it might lead you to a new position. Take the “fast or reliable?” question that every engineer uses to bludgeon managers into either forgiving sloppiness or giving them more time or resources. Except, here’s the thing.
It’s total BS. The whole reason we have prod infra or pick efficient platforms/technologies is that so we can deliver products fast and reliably. If that isn’t your reality, fix it! Worse, if you allow teams to operate in the space of this tradeoff, suddenly everyone accepts that slowness is the price of being good. Charity’s “In Praise of Normal Engineers” is another dichotomy buster.
At Google while I was Sundar’s Tech Advisor, I built a tiny team called TAG, the Tech Advisory Group. Our mission was to support Sundar and Google’s most strategic endeavors, from improving how we used OKRs and KPIs (despite Google’s history with OKRs, many teams struggled to use them effectively) and staying up-to-date on technical advances, to long-term visioning and risk analysis. It was a thrilling and tense job during the creation and emergence Large Language Models. It’s a real source of satisfaction to look at products and strategies today that came out of our work.
Birds on a wire
By far the hardest part of the job — and the most challenging to teach — was managing the limited time and misaligned incentives of senior leaders. At Big Tech companies, senior leaders are running Fortune 500-sized businesses. Unlike those CEOs, internal leaders also have to navigate strategy taxes, align with the overall company vision, and navigate peer teams with overlapping responsibilities.
TAG was often responsible for finding solutions that cut across those senior leaders — and all of their differing incentives and goals. Our friend Fred had a great comment about the position we were in:
You are birds on a wire. You’re between incredibly powerful people and like a bird on the wire, if you touch either pole you’re going to get fried.
A friend and former colleague reached out after reading the mobile transition and other posts with a good suggestion:
The “what happened” is fun, but I’d be more interested to read about how you do what you do.
I thought it was a really good suggestion! I’ve added a new section “How I...”
And to get things started:
How I...Become a Regular
I don’t know about you, but as a kid, one of the coolest moments in movies was when our hero walked into a restaurant, got greeted by name, and taken to a great table. Inevitably, the chef would come out and casually mention that they were “working on something special” and offer to give them a taste. Billions’ showrunner, Brian Koppelman, captures this with Axe brilliantly.
To me, this always seemed magical and unattainable — like the surfing and skydiving in Point Break. But, as I’ve gotten older, I discovered I have a real knack for it. Being a food fanboi helps, of course, but when a SmartNews colleague asked how the hell I already knew so many chefs in Tokyo — a city I had never spent time in — it felt worth writing up.
Because, like anything else, there’s a playbook.