How to run a difficult meeting with executives

The other day I had a difficult meeting where I was under a tremendous amount of pressure from our engineering directors. My boss J was sitting in it for the first time — J didn’t say anything during the meeting, but after the meeting, he gave me a step-by-step rundown of how the meeting went, the things I said, and how if I had framed things a certain way, I would have been more effective. Two things I learned from our debrief:

(1) Use detail as a tool to build trust.

There are little things, that when phrased differently, can have a big impact. In the meeting, I was under a lot of pressure to reach alignment with an Autopilot manager to decide whether his features were shipping with this release, but I was having trouble getting in contact with him all morning. You could explain the situation to the executive team in two ways:

Less useful: “I couldn’t get a hold of them.” (your bias for action is abstract)

More useful: “I tried calling them, but they didn’t pick up.” (your bias for action is concrete)

It’s a small difference in word choice but a big difference in how people perceive you as someone who is capable of driving results.

(2) Being decisive about the world enables you to make progress faster.

Most people who ask someone to make a decision, ask for a decision in an open-ended way. e.g. “what are you going to do about X?” Even the directors fell into this trap when they asked Autopilot manager, “What are we doing about these new features?” It’s much more useful to instead, define the world for them, and ask them to answer the question in the context of the world you have defined.

Less useful: “What are you doing about this new feature?” (the conversation goes on for 30m+ as we navigated through all the assumptions that needed to be made in order to answer this question)

More useful: “We are shipping this firmware in 5 days. Are you going to be on the train or not?” (by indicating when you are going to ship the firmware, you define the world for them)

You can always change the context later, but defining the world makes it easier for them to make a call, because you are scoping down the unknowns.

It was refreshing to get this level of feedback — most feedback at work is about overall performance than at a day to day level. I remember when I first started playing rugby at Brown, which went undefeated in the Ivy league for several years, I was amazed at how quickly I picked it up. At first, I arrogantly attributed it to my athletic dexterity — then I realized it was the nature of the training program — the immediate feedback from our coach on all the micro-drills created the perfect feedback loop. I was being given targeted guidance on exactly what I was doing wrong and why. And wasn’t just rugby — the same dynamic also helped me in coding. And it’s not just me — as people, we are beholden to making progress in environments with tight loops.