Leading through uncertainty is hard because most of the information around us produces feelings, not decisions. Descript’s CEO, Laura Burkhauser, has a simple tool for turning a shapeless worry into something you can act on: the sandwich bet. Here’s how it works and how to use it with your team.
Going in with aplomb
The word that stayed with me after my conversation with Laura on Slideshow with Dave Hayward was intrepid.
If you haven’t come across it, Descript lets you edit video and audio like a document: you edit the transcript, and the video edits itself. It’s become a tool of choice for podcasters, marketers and video teams. Laura took over as CEO in 2025, after being identified as a successor almost from the day she joined. (Yes, the episode was recorded and edited on Descript. A bit meta.) Her German literature degree, class of 2008, and my fine arts degree, class of 2000, got us off to a flying start.
Intrepid people go into uncertain territory with aplomb. They suspect there might be adventure in the unknown, as well as danger. It’s the attitude Laura says you need to lead a business through a disruptive moment, and right now most businesses are in one.
Why uncertainty is so hard to lead through
The problem with uncertainty isn’t a lack of information. It’s that most of the information is designed to produce a feeling rather than a decision. The worry sits there, shapeless and hard to act on.
The sandwich bet: a tool for decisions under uncertainty
You name what you think will happen, and by when. If you’re right, the other person owes you a sandwich. If you’re wrong, you owe them one.
That’s it. But making the bet does something important. It forces you to turn a shapeless worry into a specific, testable claim, and a specific claim is something you can think about, plan around and revisit.
Laura uses it at Descript to align her team when she makes a call they weren’t expecting. It works for AI predictions, hiring decisions, pricing calls and market bets: anywhere you have conviction but not certainty. (I first wrote about sandwich bets on AI and jobs earlier in the year.)
Three bets from the same information
When I asked readers for their sandwich bets on AI and jobs, three stood out:
- Mark Laurence, AI literacy educator: by the end of 2027, entry-level job openings will be down 10% relative to senior roles.
- Javier Yebenes, B2B marketing strategist: by 2028, marketing teams will shrink sharply, and generalists who can think and use the tools will thrive. He’s set a calendar reminder for December 2028.
- Andrea Halal, tech marketing leader: AI’s productivity gains will show up in how we live as well as in output, with more time for health, focus and the things that matter.
Three different conclusions from the same information. That’s the other thing Laura likes about the tool: it makes visible that the future isn’t fixed and reasonable people can disagree. Which means your read on what’s coming is worth something.
Try it this week
Pick something in your business that’s sitting in the “not sure about this” category. Write one sentence: what do you think will happen, and by when? Then tell someone.
The intrepid move is going on record before you know how it ends.
If you’d like help turning a big uncertain call into a plan, book 30 minutes with me.
Questions people ask
What is a sandwich bet?
A light-hearted prediction with a specific outcome and date. If you’re right, the other person buys you a sandwich; if you’re wrong, you buy theirs. It turns vague worry into a testable claim.
How do leaders make decisions under uncertainty?
By making their assumptions specific and dated, so they can be tested and revisited. Writing a prediction down and sharing it is a simple way to do that.
Can sandwich bets work with a team?
Yes. Laura Burkhauser uses them at Descript to align her team behind unexpected calls, and to make disagreement visible and useful.
This article first appeared in Bright Objects, my fortnightly newsletter on brand, marketing strategy and AI for business and tech leaders. Subscribe here.
Sources and further reading
- Slideshow with Dave Hayward, Laura Burkhauser (Season 2, Episode 4): YouTube
- Descript
- What’s your AI sandwich bet?, europa.nz
If you know your business is all steak and needs some sizzle….. we’d love to hear from you.
Dave Hayward
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Warm personal stories wrapped around solid business, revenue and marketing strategy, how-tos, technology discussion (especially AI), philosophies and tactics. Occasionally, we’ll talk about personal productivity and things important to us (like astronomy and dogs).
