Do a Black Sky brainstorm to find out and save your startup. This year I cofounded a company called to administer high-value health insurance plans for freelancers. We use blockchain to make healthcare more affordable, transparent, and fair. As I told , “We’re tackling the most regulated industry in the country with the most overhyped technology in the world. What could go wrong?” Decent seed investors 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 to find out what the team is worrying about, along with some of our smartest investors from , and turn all that anxiety into a plan. Black Sky brainstorm Maverick 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. 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. Schedule a meeting with some or all of your team. 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. Share your definition of failure. Make sure everyone has post-it notes and a pen. 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! Start the timer (I recommend 5 to 10 minutes). I recommend that each participant gets one vote per participant (so if there are 5 participants, each gets 5 votes). When time is up, put up your post-its on a worry wall and vote on what you’re most worried about. 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. Talk about each threat with at least 1 vote, in declining order of votes. 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. If you found a headshot, pivot. If you didn’t, celebrate! Here’s a Black Sky worry wall, pre-voting. Squint and you might see why healthcare is messed up. What will you get? 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 learn what your team is (and isn’t) worried about. Ready, aim, fire should apply to worrying as well. You’ll get a prioritized list of where to point your anxiety. Google found that psychological safety is a . When you’ve shared your worries, it’s much easier to talk about mistakes. You’ll create a safe psychological space for people to open up. top trait of high-performing teams It’s amazing what happens when you point several smart brains at a problem. You’ll work through some concerns in the meeting. You know that feeling. Ahhh, yeah. You’ll all get that nice buzz that comes from making a good plan. I’m excited to see what people do with this. If you have questions or ideas, email me at . nick@decent.com

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Your team knows what’s going to kill you.

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Your team knows what’s going to kill you.

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