Your team knows what’s going to kill you.

Do a Black Sky brainstorm to find out and save your startup.

This year I cofounded a company called Decent to administer high-value health insurance plans for freelancers. We use blockchain to make healthcare more affordable, transparent, and fair. As I told seed investors, “We’re tackling the most regulated industry in the country with the most overhyped technology in the world. What could go wrong?”

These days I have some pretty good answers to that question.

Half the time I spend worrying about my startup is wasted; the trouble is I don’t know which half. I believe we’ll succeed, but there are so many ways we might fail. Will we build something no one wants? Struggle to scale? Get stomped by a competitor? We could spend years in deep, unspoken anxiety — and many startup teams do.

But there’s a better way.

Last week we did what I call a Black Sky brainstorm to find out what the team is worrying about, along with some of our smartest investors from Maverick, and turn all that anxiety into a plan.

Who is a Black Sky brainstorm good for?

All working or would-be startuppers, at any stage of their journey. Especially the ones with too much to do and the sometimes-blinding optimism it takes to think you can change the world. If that sounds like you, read on.

What is a Black Sky brainstorm?

A Black Sky brainstorm is an exercise where you work with people on your team (and optionally others) to think of all of the different things that could make your startup fail. It combines the free exploration of blue sky thinking with a clear-eyed focus on what could go wrong. Here’s how you do it.

1. Schedule a meeting with some or all of your team. I recommend at least 1 hour, and at least 3 team members with unique accountabilities. Make sure to include voices who don’t always chime in on strategy.
2. Share your definition of failure. For us it was “Not being a beloved and fast-growing health insurance company in the next 3 years.” You could choose something nearer-term too, like a product launch or partnership.
3. Make sure everyone has post-it notes and a pen.
4. Start the timer (I recommend 5 to 10 minutes). Have everyone work silently to come up with all the threats they can think of to your business. You’re going for volume — no threat is too ridiculous!
5. When time is up, put up your post-its on a worry wall and vote on what you’re most worried about. I recommend that each participant gets one vote per participant (so if there are 5 participants, each gets 5 votes).
6. Talk about each threat with at least 1 vote, in declining order of votes. If you run out of time, this ensures you cover the top vote getters, but I recommend touching on anything with a vote, so all big concerns are heard. You’ll probably come up with questions and follow up research.
7. If you found a headshot, pivot. If you didn’t, celebrate! A headshot is a risk that participants agree is insurmountable, in the meeting or after research. It’s a good idea to look hard for them, especially early on.

Here’s a Black Sky worry wall, pre-voting. Squint and you might see why healthcare is messed up.

What will you get?

• You’ll learn what your team is (and isn’t) worried about. This is about both uncovering new problems and prioritizing known ones. Early stage startups require sustained optimism, and nothing kills optimism faster than an elephant in the room, especially one leaders can’t seem to see.
• You’ll get a prioritized list of where to point your anxiety. Ready, aim, fire should apply to worrying as well.
• You’ll create a safe psychological space for people to open up. Google found that psychological safety is a top trait of high-performing teams. When you’ve shared your worries, it’s much easier to talk about mistakes.
• You’ll work through some concerns in the meeting. It’s amazing what happens when you point several smart brains at a problem.
• You’ll all get that nice buzz that comes from making a good plan. You know that feeling. Ahhh, yeah.

I’m excited to see what people do with this. If you have questions or ideas, email me at [email protected].