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

Janna Bastow is a former product manager, and currently the CEO and co-founder of ProdPad. She also co-founded Mind the Product, a community for PMs, which has grown to 300,000 members across the world. In today’s podcast, Janna discusses the limitations of timeline-based Gantt charts and her “Now/Next/Later” framework. She also shares stories about hosting conferences and gives some great tips on how to improve your presentation skills and cope with performance anxiety. Find the full transcript here: https://www.lennyspodcast.com/building-better-product-roadmaps-janna-bastow-mind-the-product-prodpad/#transcript — Where to find Janna Bastow: • Twitter: https://twitter.com/simplybastow • LinkedIn: https://www.linkedin.com/in/jannabastow • The ProdPad newsletter: https://www.prodpad.com/newsletter/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Thank you to our wonderful sponsors for making this episode possible: • Formsort: https://formsort.com/lenny • Coda: http://coda.io/lenny • Amplitude: https://amplitude.com/ — Referenced: • Mind the Product: https://www.mindtheproduct.com/ • The Trouble with Traditional Roadmaps: https://www.prodpad.com/resources/guides/ditch-the-timeline-roadmap/the-trouble-with-traditional-timeline-roadmaps/ • ProdPad’s Sandbox: https://www.prodpad.com/sandbox/ • Geoffrey Moore’s product vision template: https://www.prodpad.com/blog/product-vision-template/ • The Art of Profitability: https://www.amazon.com/Art-Profitability-Adrian-Slywotzky/dp/0446692271 • The Sandman on Netflix: https://www.netflix.com/title/81150303 • Startups for the Rest of Us podcast: https://www.startupsfortherestofus.com/ • Christina Wodtke on Twitter: https://twitter.com/cwodtke — In this episode, we cover: (00:00) Janna’s background (05:28) How the community evolved at Mind the Product (08:22) The tricky logistics of putting together a conference (10:48) Are conferences profitable? (13:00) How Janna developed her storytelling and presentation skills (16:44) How to fight performance anxiety (19:25) Mistakes are humanizing—how to power through and deliver your presentation (22:11) The limitations of traditional timeline roadmaps (25:00) Janna’s Now/Next/Later framework (28:08) How to work without the structure of dated timelines, and why soft launches are important (32:57) What great product teams are doing well (35:05) The importance of retrospectives (36:45) How to shift the culture at larger companies (39:43) How ProdPad creates better product management practices (42:04) How to learn the Now/Next/Later framework (46:59) Geoffrey Moore’s product vision template (48:36) Lessons for PMs interested in becoming founders (50:48) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Janna BastowguestLenny Rachitskyhost
Oct 15, 202253mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Roadmaps As Strategy Prototypes: Janna Bastow Redefines Product Planning

  1. Janna Bastow, co‑founder of Mind the Product and founder of ProdPad, argues that roadmaps should be treated as evolving prototypes of strategy, not fixed delivery plans. She explains her popular Now–Next–Later framework as an alternative to date-driven Gantt charts, emphasizing learning, discovery, and outcome-focused planning over rigid commitments.
  2. The conversation ranges across community building (Mind the Product’s growth and conference war stories), public speaking and storytelling tactics, and the realities of transforming product culture in large organizations. Janna also shares how tools and processes can enforce better product habits, such as continuous discovery, retrospectives, and psychological safety.
  3. She positions modern product work as experimentation similar to sales: teams should be accountable for running smart experiments and moving outcomes, not for magically predicting exact delivery dates. Finally, she offers advice for PMs who want to become founders and how to craft practical, clear product visions.

IDEAS WORTH REMEMBERING

5 ideas

Treat your roadmap as a prototype of your strategy, not a contract.

Janna frames the roadmap as a way to surface and test assumptions about problems and priorities; its value lies in the roadmapping process—sharing, challenging, and refining—rather than the artifact itself.

Replace rigid timelines with a Now–Next–Later roadmap for most work.

By organizing work into ‘Now, Next, Later’ instead of assigning dates to everything, teams acknowledge uncertainty, reduce pressure to hit arbitrary deadlines, and keep focus on sequencing and learning; dates are reserved only for truly date-constrained initiatives.

Separate soft launches from hard launches to align product and marketing.

Ship when development is ready (soft launch), then let marketing plan a separate, better-prepared hard launch once they can see and use the real product, avoiding misaligned timelines and rushed campaigns.

High-functioning product teams invest heavily in discovery and retrospectives.

Teams that regularly talk to customers, question assumptions, and run honest retros create psychological safety and continuous improvement, which naturally leads to better prioritization, experimentation, and more realistic roadmaps.

Use tools and process nudges to enforce good product habits.

ProdPad is intentionally designed to make bad practices hard (e.g., feature-only, date-locked roadmaps) and good practices easy (defining problems, outcomes, experiments, and success measures), showing how tooling can shape culture.

WORDS WORTH SAVING

5 quotes

The value isn’t in your roadmap. The value is in the roadmapping process.

— Janna Bastow

I think about a roadmap as being a prototype for your strategy.

— Janna Bastow

We don’t live in la-la land. If something has a regulatory date, it should absolutely have a date on the roadmap.

— Janna Bastow

You’re not asking for any more leeway than your salesperson.

— Janna Bastow

People in the audience are rooting for you. No one is rooting for you to fall over and have a bad time.

— Janna Bastow

Roadmaps as strategy prototypes vs fixed delivery plansNow–Next–Later roadmapping framework and problems with Gantt chartsCo-founding and scaling the Mind the Product community and conferencesPublic speaking, storytelling, and managing stage anxietyTraits of high-performing product teams (discovery, retrospectives, psychological safety)Driving product culture change in large organizationsUsing tools (ProdPad) to enforce better product management practicesCareer progression from product manager to founder and product vision frameworks

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