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Janna Bastow: Your roadmap format is training stakeholders to ask the wrong question.

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Interview · Janna Bastow · Oct 16, 2022

Building better product roadmaps | Janna Bastow (Mind the Product, ProdPad)

Start from the original episode or newsletter, then use the ideas below in the reps.

Key ideas to remember

  1. 01 A Gantt chart is structurally a delivery commitment — not a hypothesis about what to build or why — so switching formats is not cosmetic, it's a change in what questions you and your stakeholders optimize for.
  2. 02 The Now/Next/Later format replaces dates with confidence levels: Now is scoped and in-flight, Next is directionally known but loose, Later is a recognized problem space not yet ready to scope.
  3. 03 When a stakeholder asks 'when?', the right reframe is 'what would we have to learn to make this a Now item?' — moving progress from calendar-driven to evidence-driven.
  4. 04 The best product teams maintain active discovery and psychological safety alongside the right format; without both, even a good roadmap format gets executed as a fixed list no one questions.
  5. 05 Treat the roadmap as the artifact of an ongoing conversation — something updated as your understanding improves — not as an authoritative source of truth to be delivered.
3-minute summary

Your roadmap format is a behavior-shaping tool — and Gantt charts are shaping the wrong behavior

Janna Bastow, co-founder of ProdPad and Mind the Product, spent years as a PM doing what most PMs do: building colorful Gantt-chart roadmaps, lining features up against due dates, and getting praised for hitting them. Then she noticed the problem wasn't her delivery — it was the format itself.

A Gantt chart is not a plan. It's a commitment. The moment you attach a feature to a date, you've ended the conversation about whether that feature is the right thing to build. The only question that remains is whether you hit the date. And when you reward date-hitting over problem-solving, you train everyone in the room — including yourself — to optimize for the wrong thing.

The Now / Next / Later format is the structural fix. It replaces calendar dates with confidence levels. Now is what you're building this quarter — high-confidence, scoped, in flight. Next is the problem you expect to tackle next — directionally known but scope is still loose. Later is the problem space you know matters but haven't scoped yet. This isn't a cosmetic rebrand of the same roadmap. It literally changes the question stakeholders ask. Hand someone a Gantt chart and they ask, 'When will it be done?' Hand them a Now/Next/Later board and they ask, 'What outcome are we chasing, and why is this next?'

Progress through the board is earned by evidence, not calendar. When a stakeholder asks 'when will X ship?', the right answer isn't a date padded with buffer — it's: 'What would we have to learn to make that a Now item?' A Later item becomes Next when you've reduced uncertainty enough to believe it's the right problem. Next becomes Now when you've scoped it tightly enough to commit. The roadmap becomes a living record of your confidence, not a delivery schedule.

The best product teams pair this format with two other habits. First, active discovery: continuously questioning customers, testing hypotheses, iterating based on what you learn — not executing blindly against a fixed feature list. Second, psychological safety: team members have the standing to question the roadmap mid-flight, to say 'this might be the wrong thing,' without it becoming personal. When both are present, the roadmap stays honest. When neither is present, the team executes a plan no one believes in and nobody says so.

The roadmap is an artifact of an ongoing conversation, not a source of truth. Thriving teams don't treat the roadmap as the authority that dictates work. They treat it as the output of continuous discussion — something that gets updated as understanding improves. That shift in mental model changes how PMs present roadmaps, how they defend prioritization decisions, and how they respond when evidence contradicts the plan.

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