How to outline a bet

We’ve seen how important taking on the right bets is to long term success. To properly compare them against one another, we need an agreed format. The format should have less information than a full blown business case, and more information than a User Story. The Goldilocks template if you will.

Great things happen on a single page. One-pagers hit the sweet spot on a number of levels. It forces authors to be succinct, no fluff. They are easier to compare side-by-side. They can be printed out and stuck on the wall. They balance the value of information and the cost of getting it. They exist to communicate the data, insights and hypothesis of a bet.

One-pagers also have a clear and measurable outcome
(Cutler, 2018). The outcome may range from a full-blown feature or moving the needle on a problem or metric (with the solution TBD).

They have also have step-goals. A one-pager may span multiple sprints. These step-goals are not meant as traditional, overbearing stage-gates, but more as a chance to pivot. This is to ensure teams don’t go blindly adding lipstick to a pig, or move on too quickly when the goal hasn’t reached it’s true outcome.

The true outcome of any one-pager should be behavioural change. In building new software, you ultimately want the User to change the way they do something.

  • Do something new
  • Do something faster
  • Stop doing something bad
  • No longer a need to do it (automation)

You’re changing their behaviour in some way. If you build a feature that doesn’t end up changing behaviour, you lost your bet.

The Goldilocks Template

  • Title
  • Mission: Who + Current Behaviour + Future Behaviour + Benefits to User + Benefits to Business
  • Key data points
  • Key insights
  • Hypothesis
  • Pivot and proceed points
  • Keys to success
  • Assumptions to validate
  • Impact
    • SMS sent to business revenue?
    • 50 * 300 * .18 = $2,700 a month in SMS revenue
  • Confidence?
  • Estimate?

Notes on using the template

You don’t have to have all the answers up front. The one-pager should encourage spirited discussion. It might inspire missions to go find the missing answers.

One-pagers will evolve, with layers of detail being added over time.

Survival of the Fittest

One-pagers will also die. Don’t be afraid to kill off a one-pager. If you find enough evidence to kill off a one-pager, you should celebrate (perhaps with a ceremonial burning?). Avoiding bad bets saves everyone weeks of heartache and the company a lot of money.

The best way to promote evolution between bets is competition.

Make sure you have at least 3 different one-pagers of comparable detail.

Now assess them against these trials by combat and see which one is victorious:

  1. Which one-pager would you bet your own paycheck on to succeed? Why? What might we learn early on that would encourage you to double-down? Or decrease your bet by half?
  2. Have we tried to solve any of these in the past? What happened?
  3. What is the status quo we are hoping to disrupt?
  4. Which one-pager has had efforts taken to defeat confirmation bias, the availability heuristic, information bias, the IKEA effect, and other cognitive biases? How might a less-biased person view these bets?
  5. Describe the “good news” you hope to elicit as a result of this effort. How might you describe it in a company-wide presentation in a non-success-theater, non-fluffy way? Write the dream customer feedback tweet. How might the good news change in the short, mid, and long term as we realize the benefits?
  6. Explain how this connects to the broader company strategy. Why is this a critical part/piece of the puzzle? Together with other initiatives, are we telling a cohesive story?
  7. Why now? Why is this the most important problem to solve right now? How might the financial outcome be different if we did this in six months, one year, or never? Explain how it “beats” a handful of other things you are considering.
  8. You’re about to occupy some % of the careers of a couple fellow human beings. Why should they come along for this adventure?
  9. What early indicators might indicate that we’ve placed a good bet and would signal that it is safe to move on to other things?
  10. Let’s say we don’t do this. What will actually happen to the business in the short, mid, and long term? To our customers/users/partners/team?
  11. Does this effort rely on other efforts to be successful? Describe how the efforts are related. If they are truly dependent, can/should we pursue them concurrently, or combine them somehow?
  12. Challenge yourself to cut the scope here by 75%. Would that deliver some value? Should we pursue that first, even if it expands the overall scope a bit?
  13. How much money are we losing each week (new opportunities or cost savings) by not solving this problem? How does that compare to the money we are losing each week by not solving other problems?
  14. In the spirit of challenging the sunk-cost fallacy, what might happen part-way through this effort that would persuade you to stop work?
  15. Describe the various forces and shifts that must come together to make this successful? What do we control? What don’t we control? What can we influence?
  16. Play your own Devil’s Advocate for a moment. Give me three good reasons why this isn’t a good idea. Now give me three good reasons why solving another problem is a better idea.
  17. Who will this impact? Say I wanted to identify the customers/users this will impact, what query would I run? How might I quantify the impact over time?
  18. Can we design some safe-to-fail experiments to help us solve this problem? Overall, how can we expand our “portfolio” of bets here, and get faster feedback?
  19. What are the known unknowns here?
  20. Where are you making leaps of faith in terms of user behavior? What is your plan to close the learning gap? When will you get this into the hands of real humans, with real data, trying to do their real job?
  21. Do you have a plan for regular usability testing? How often? How early? Have you set aside time to act on what you learn during these tests?
  22. How will you instrument your solution to measure outcomes and learn?
  23. What’s your plan to work “end-to-end” across the problem and the solution, such that we don’t arrive, finally, at a solution and discover the parts don’t fit together as expected?
  24. What is the behavior you hope to change? What will customers/users do more of, less of, start doing, and stop doing as a result of this work? How will that behavior change benefit the customer/user and the company?
  25. What information would make solving this problem easier? Are we missing insights that might improve our “batting average” here? How might we obtain that information?
  26. What problem might we solve, such that this problem would be a non-factor? Why aren’t we trying to solve that problem?
  27. How will we measure the impact and success of this effort in the short, mid, and long term?
  28. What is your plan to regularly reduce “benefits risk” (the risk this effort will not achieve the desired benefits) as the effort progresses?
  29. How might you describe the various other risks in this effort? How will you incrementally reduce those risk levels?
  30. What must we “get right” to succeed at this effort? Where can we be less-than-awesome, and still succeed? What should we ignore? What can we “suck at”?
  31. Who do we need involved to make this a success? Any special skills? Any special insights?
  32. What assumptions must hold true for this initiative to remain the most important thing we can work on?
  33. Is this the lowest hanging fruit? If I asked your team to spend the next week fixing “small things with a big impact” would this top the list? Would it have a greater cumulative value? Say you only had two weeks to solve the problem (or chip away at the problem)…what would you try?
  34. Can you commit to a “pivot/proceed” decision point? When will we stop iterating on this? Please draw a line in the sand.
  35. It is a six months from now and this effort has failed. Describe three plausible reasons why it failed. Tell a good story.
  36. What is the leap of faith here? What must I believe without supporting data?


Cutler, J. (2018). Great One-Pagers. [online] Medium. Available at: [Accessed 8 Jan. 2019].

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