Our roadmap has no dates after six weeks. Sales survived. Here is how

Six months ago our roadmap was a Gantt chart with quarter-end dates on everything for the next 12 months. Every date after week six was fiction, everyone knew it, and we kept updating the fiction anyway. Some notes on what we replaced it with, at a 40-person health tech startup.

The format

• Now (next 6 weeks): committed, with dates. The team has estimated it and it is in a sprint plan.
• Next (roughly 6 weeks to 3 months): the problems we intend to solve, in order. No dates. A confidence level instead: high, medium, low.
• Later: problems we believe matter but have not validated. Explicitly allowed to disappear.

Every item is written as a problem, not a feature. "Clinics lose referrals when the receiving clinic does not respond within 48 hours" instead of "Referral reminders v2".

The sales conversation

The fear was sales. Our customers are clinics and regions, and procurement wants dates. What we actually did:

• Sales gets the Now column with dates, and can promise those.
• For Next, sales can say "this is the problem we are working on next, high confidence it lands this half". Our head of sales said it was easier than defending dates that moved every month.
• For a customer who needs a date to sign, the decision goes to the leadership team, explicitly, as a trade-off: if we date this, what moves? That made the cost of a promise visible. We have done it twice in six months instead of every week.

What did not work

• Confidence levels drifted towards "high" because nobody wanted to say "low" in front of the CEO. We now write one sentence of reasoning next to each confidence level.
• Our board still wants a 12-month view. They get a themes slide, not a feature list. It is lagom satisfying for everyone, which is to say nobody loves it.

Not a revolution, and plenty of people have written about Now/Next/Later before. But it changed how often we lie to ourselves, which is a decent outcome for a slide. Happy to be proven wrong!