People say you get to wear different hats in startups. I learned this when I joined Forward as an engineer in 2016.
I’d walked out of a design review. We’d spent the meeting discussing architecture and technical risks. I was getting things, feeling in sync with my teammates. My next discussion was with clinicians building care plans. A few minutes in I was missing cues, and wasn’t asking good questions.
Over the next weeks I noticed members of each team have issues collaborating. They spanned engineering, medicine, product, design, operations. I also saw them struggle to adapt to the sheer amount of change that comes from rapid building.
It took us a while to find our groove. Each conversation required a different version of our outlooks, backgrounds, and skills. Each project required different execution. When we did it right we built a shared understanding of products, technology, and medicine. When we didn’t we failed in confusion.
I found it useful to build intentional approaches to these problems. I started imagining them as the proverbial hats. I thought about what they are, what they let us do, and when we’d wear them.
Let’s see how far I can stretch this metaphor.
The Hats
Communication Hats
Successful teams communicate well. Here are some hats that help.
The listener’s hat
Skills: Listen and learn.
Wear when: All the time.
The presenter’s hat
Skills: Tell a relevant story, to the right audience, with style.
Wear when: it’s time to sell, to inspire, and entertain.
The writer’s hat
Skills: Encapsulate knowledge, and make it available in words.
Wear when: When you find reusable knowledge that takes work to assemble.
Don’t wear when: When the knowledge isn’t reusable, or is redundant.
The debater’s hat
Skills: Make your best case. Compare it with the best versions other cases.
Wear when: Discussing important points in good faith.
Don’t wear when: When the point is irrelevant.
The editor’s hat
Skills: Streamline communication. Highlight important details.
Wear when: Information isn’t clear, or is overwhelming.
Don’t wear when. You’re forcing your opinions onto others.
Care Hats
Startups take a toll on you and those around you. The hours, ambiguity, learnings, and failures aren’t easy. Some hats nourish your body, mind, and spirit.
The humble hat
Skills: Humility. Allowing yourself to learn. Releasing ego.
Wear when: All the time. Startups will make you learn. You will be wrong a lot. It’s ok.
The feedback hat
Skills: Honestly observe yourself and your team.
Wear when: You see behavior that needs a change or reward.
Don’t wear when: You like your voice more than you care to improve.
The rester’s hat
Skills: Sleeping. Going on walks. Pausing notifications. Meditating…
Wear when: When you want to be creative, and yourself, the next day.
Don’t wear when: You have reserves and it makes sense to dive in.
The hard hat
Skills: Grit. Persevering when the hard knocks come.
Wear when: You’re taking on the right kinds of problems.
Don’t wear when: conducting Sisyphean tasks.
Execution hats
As countless posts from SV-ers will tell you, execution counts for most of a startup’s success. I’ve found these useful.
The leverage hat
Skills: Make systems do work for you. Gain through equity, not effort.
Wear when: You’re solving frequent problems — shipping, listening, learning, getting rewarded. But really, ideally all the time.
The builder’s hat
Skills: Go deep, and create something.
Wear when: You understand the problem.
Don’t wear when: When you don’t understand the problem. When the thing’s built and working.
The race driver’s hat.
Skills — go fast, at the right speed.
Wear when — you’ve charted the course, and you’ve got a full tank, or battery.
Don’t wear when — When you think every turn requires the same speed.
The planner’s hat.
Skills: make things run on time. To plan a complex movement.
Wear when: You need to run and evolve a process.
Don’t wear when: It’s busywork. You’re overcomplicating things.
The accountant’s hat
Skills: Make sure the numbers foot.
Wear when: Measuring a valuable resource. Time and money come to mind.
Don’t wear when: Measuring a meaningless resource.
Clarity Hats
Startups throw teams into ambiguity. This leads us to…
The dreamer’s hat
Skills: Combining imagination and optimism.
Wear when: You need vision
Don’t wear when: You dream only because it’s convenient.
The captain’s hat
Skills: The ability to lead. To be the single responsible individual.
Wear when: When you’re the right person for the job.
Don’t wear when: you’re chasing prestige, are unwilling to own failures.
The thinker’s hat
Skills: Focused, uninterrupted thoughts. Ask questions. Build judgement.
Wear when: You don’t understand the problem at hand.
Don’t wear when: You’re sacrificing well-scoped action.
The arbiter’s hat
Skills: Weigh all sides of an argument. Manage decisions.
Wear when: A decision has significant consequences. When well-meaning parties block each other.
Don’t wear when: Your judgement says the decision is meaningless.
Celebration Hats
Countless sprints, launches, pivots make celebrating milestones a necessary good. The act gives us closure and perspective. It lets us reflect with each other. This means we need…
The party hat!
Skills: Kicking back, sharing stories with your team, framing memories.
Wear when: you’ve crossed a milestone — whether a success or a failure.
Don’t wear when: the moment isn’t proportionate to the achievement.
The reflection hat
Skills: Remembering the good and the bad. Not reliving those events.
Wear when: It’s time to learn from your experiences.
Don’t wear when: The present’s running by you!
The thank you hat
Skills: Thanking your teammates for a job well done.
Wear when: Someone does something meaningful.
Don’t wear when: You don’t mean it.
Hats, not masks.
Hats are a forced, imperfect metaphor. We wear many of them at the same time. We shouldn’t wear too many. This isn’t a complete list.
I still like “hats” as a metaphor. They show everyone your “face” — who you are. They show your intent. Your teammates see you use different skills, and know why. I view the opposite as “masks”. These promote secrecy and mistrust.
Hats rule. I hope you find the right ones to wear.
Thanks Aubrey Blanche, Jessica Venticinque, Kate Jenkins, and Will Larson for shaping this essay.
