writing / Always be Pitching

While I was managing the Growth team at Figma I worked from home. We lived in a small, downstairs one-bedroom with two rooms. I worked in the bedroom and my wife worked in the everything-else room.

Every day I would have one-on-ones and interviews that Courtney would inevitably overhear through our bedroom door. These are what I miss most now when I'm not managing. I loved that an important part of my job was chatting with people about work and life.

One day at dinner Courtney was like "It's fun hearing you tell the same stories all day long." I was immediately on guard because roasting me is one of Courtney's favorite hobbies. I was ready for some clever burn about how repetative and annoying I am but it turned out she was sincere. "You have your point for the day it's funny to hear you react to different people, wonder what they're saying and hear you adjust the story based on who you're talking to."

Courtney's totally right. My first explanation of an idea is always bad. Sometimes it's because the idea is bad and other times I'm being confusing. Often I haven't understood everyone's perspective or missed a key detail. However after a week of one-on-ones, I've refined the idea to it's core or discarded it. Or even more likely, someone else gave me a new even better idea to start pitching.

Great engineering leaders are always pitching. They fill blank space in meetings with ideas and make time to share their thinking with others before it's fully baked.

This kind of pitching is NOT about convincing people. When you're too focused on being right, you miss the point and waste the team's time. The most important part is listening to how your audience responds to your pitch and encorporating that in your thinking.

In practice this can look a lot of different ways. A few examples are:

• Proactively sharing what you're worried about with your reports in one-on-ones, even if it's not directly relate to their work.
• Slacking a peer to say "hey I had this idea, what do you thinkg?"
• Explaining a sense you have that something is going wrong to your boss even though you don't have the perfect answer yet.
• Repeating yourself over and over and over again with different people even after you feel good about the idea and pitch, just to see how they respond.

In exchange for the time spent repeating yourself, there are a lot of perks:

• You get feedback and improve the idea. Its important to pitch up, sideways and down for different perspectives.
• The pitch becomes much clearer and more compelling. Interesting ideas often require sharing a lot more of your internal context than you expect.
• Teammates get transparency about what the leadership team is thinking about. When then team provides feedback on your rough thoughts, they become part of the team decision making process.
• It's super fun to talk about fresh ideas! Everyone wants to be on a creative team bubbling over with potential for awesomeness.

When you do this successfully, your team will make better decisions faster and the team will be part of the process.