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Challenge 02

Uncertainty
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Build a tool that helps a team commit to a concrete next step under uncertainty, using Affordable Loss instead of expected return.

The problem

Enterprise teams keep building generative AI pilots under conditions where the input data for a proper business case does not exist. They cannot reliably know return, duration, or long-term adoption before they start.

The expected ROI calculation becomes a guess. Yet teams still build, demo, and launch pilots as though prediction were possible, often learning only months later that the work produced no measurable business impact.

Your tool should make Affordable Loss the primary decision driver: what is the smallest thing we can put on the table to find out if this is real, while being genuinely fine losing it?

Focus 01

Make loss explicit

Help a team define what they can put on the table without regret: budget, time, attention, reputation, data access, and leadership patience.

Focus 02

Force a next step

End with a concrete commitment that can test whether the approach is real, not another open-ended business case or speculative forecast.

Focus 03

Protect the decision

Surface when the team is drifting back into expected-return guesses that uncertainty cannot support.

What you are building

A decision tool that changes what teams commit to.

Design and build a tool, in any form, that makes Affordable Loss the primary decision driver when teams face high uncertainty. It can be a web app, mobile app, AI assistant, browser plug-in, Slack bot, or another form that fits the workflow.

The point is not to replace ROI with another score. The tool should give the Affordable Loss question genuine weight in real-world decision-making, make commitments visible to the team and leadership, and end with a concrete next step.

The criterion that matters is whether the tool would actually change what a team decides and help prevent the pilot-failure pattern from repeating.

Provided resources

Starter material

These documents provide background and examples for teams designing around Affordable Loss, uncertainty, and internal venture decisions.