I'm sorry to disappoint those who want this to be true, but in my experience the role of leadership is in fact to make as few decisions as possible, and to make the decisions that you are forced to make utterly mundane. Here are some of the mundane decisions I've made this year:
The first pass of a seating chart
Perfunctory approvals around uncontroversial hiring
Rubber stamping of well-thought-out architectural decisions
Signoff on budgets for vendor products we clearly need
I set up a lot of policies over the past few years. Some of them I've blogged about, for example, promotion committees. But I've also created policies around how new languages and frameworks are introduced, on-call rotations, even how we buy office equipment (oh the glamorous job of a CTO!). The goal of pretty much all of these policies is to make future decisions easier, and to empower various people on my team to make decisions without me.
So, I don't believe that good leadership is heavy on decision-making. That being said, you can't be a leader without occasionally setting a direction, which leads me to The Best Decision I Made in 2014. It started with a twitter conversation about continuous delivery, on January 3. I have been thinking about continuous delivery forever, and trying to move Rent the Runway in that direction for as long as I've been running engineering. At the end of 2013, we created a task force to make our deployments, then-weekly and taking up to 6 hours to do, faster and less painful. The team was well on their way to success by January 3. And so, inspired by my conversation, I sent this email:
Starting in Feb
That's it. I held my breath to see the responses. And as they rolled in, one by one, all of the engineers agreed. They were excited, even! So I started to tell others. Our Head of Product. My CEO. I told them "this might cause some pain, the first couple of weeks, as we figure out how to do this safely, but it's important."
And so, come February, we began releasing every work day. And it was glorious.
What made this decision so successful? What did I learn from this?
A great decision is often not a revolutionary move. We were doing the technical work to enable this already. The team wanted to be deploying more frequently. All I did was provide the push, to raise the bar just a little bit higher and express my confidence that we would easily clear it.
The thing I learned from making this call wasn't anything about the decision itself. It was about the process that got me there. You see, this came about right after new year's, when things were quiet at work and I had some time to sit alone and think (or, in this case, tweet). All the sudden, I had ideas again! And it hit me: I need regular time alone, away from meetings and people, in a quiet room with a whiteboard.
So I started blocking my calendar every Wednesday afternoon, and things started to change for me. In those Wednesday afternoons, I thought through the next evolution of our architecture. I thought through our engineering ladder, and our promotions process. I thought about problems I was having with people and how I could make those relationships better. I did some of the foundational work to create the 7 completely new talks that I wrote and delivered in 2014. I made time for the important but not urgent. In short, I grew from a head of engineering focused on the day-to-day into a CTO who thought a lot about the future.
The best decision I made in 2014 wasn't, actually, to tell my team to release every day. That's just the story I've been telling myself all year. The best decision, really, was to make time to think.