Lenny's PodcastBuilding better roadmaps | Janna Bastow (Mind the Product, ProdPad)
CHAPTERS
- 4:47 – 6:13
Janna Bastow’s path: from accidental PM to building ProdPad and Mind the Product
Janna shares her product management origin story and how she ended up founding two major product-focused ventures in parallel: ProdPad (a product management tool) and Mind the Product (a global community). She sets the context for why roadmapping and community building became central themes in her career.
- •Fell into product management and rose to Head of Product at a London startup
- •Spotted a gap in product management tooling and began building ProdPad
- •Co-founded Mind the Product, which grew into a massive product community
- •ProdPad’s core jobs: roadmaps, OKRs, feedback/ideas capture, and organizing PM work
- 6:13 – 7:42
How Mind the Product grew: grassroots learning, consistent cadence, and shared ownership
Rather than setting out to manufacture a community, Janna describes how Mind the Product started as product people learning together. Consistency (monthly meetups, annual events) and distributed contribution helped it scale while keeping quality high.
- •Started as informal peer learning: “we didn’t know what we were doing”
- •Maintained a reliable rhythm (monthly ProductTank, yearly events)
- •Scaled by surrounding themselves with the right people and curators
- •Brought in speakers/writers beyond founders’ immediate networks
- 7:42 – 8:22
Scale and evolution: global chapters, COVID shifts, and the sale of Mind the Product
Janna explains the approximate scale of ProductTank and how the community changed during COVID, with some chapters going virtual and later returning in-person. She also notes Mind the Product was sold, which changed how closely she tracks current metrics.
- •At peak: ~200–300 cities running ProductTank chapters
- •COVID caused fluctuation: up/down, with a mix of digital and in-person today
- •Thousands participate globally across meetups and conferences
- •Mind the Product was sold, so she’s less connected to exact current numbers
- 8:22 – 10:49
Why conferences are brutally hard: logistics failures and expensive surprises
The conversation turns to the operational reality of conferences as a non-lean, high-stakes endeavor. Janna recounts concrete failure modes (catering shortfalls, vendors collapsing, speaker changes) and how community goodwill helped them recover.
- •Events are “un-lean”: you can’t iterate quickly once the day arrives
- •Failures are costly at the thousands-of-dollars level (travel, printing, venues)
- •Real examples: under-delivered catering, venue/afterparty venue going bust
- •Goodwill and community support can help you survive inevitable mishaps
- 10:49 – 12:58
Are conferences profitable? The risk profile and what makes them work
Janna breaks down the business model: events can monetize well at scale, but early on they’re highly risky and easy to kill through underselling or external shocks. A strong pre-existing community becomes the primary “marketing engine.”
- •Conferences can be profitable, but typically only at meaningful scale
- •Ticket undersales can kill an event series immediately
- •Hard to insure against tail risks (e.g., COVID)
- •Community-building years ahead is what makes ticket sales achievable
- 12:58 – 16:43
Becoming a great speaker: learn by watching, then invest in coaching and rehearsal
Janna describes how exposure to many top-tier talks helped her develop strong taste for what works on stage. A speaker coach helped her tighten structure, jokes, delivery, and posture—and rehearsal plus playback became key to improving.
- •Learning loop: observe many talks and note what audiences respond to
- •Speaker coaching: rewriting, delivery, posture, phrasing, and “landing” points
- •Start with narrative/story beats before building slides
- •Record and play back your talk; rehearse until it’s fluent anywhere
- 16:43 – 19:23
Managing stage anxiety: power posing, stage familiarization, and audience ‘anchors’
Janna shares practical techniques to reduce performance anxiety, including confidence-boosting physical routines and early exposure to the stage environment. She also recommends focusing on supportive audience members rather than distracted faces.
- •Use a power pose pre-talk (even if it’s ‘placebo,’ it can work)
- •Walk the stage during tech check; visualize the room full
- •Ignore bored/phone-checking attendees; find “fans” who are engaged
- •Deliver the talk to a few friendly faces across the room for stability
- 19:23 – 22:12
Screwing up is survivable—and often humanizing: how to recover mid-talk
Janna recounts freezing during an early ProductCamp welcome and restarting on the spot. The key learning: audiences generally root for you, and small mistakes can make you more relatable—just breathe, reset, and continue.
- •Early experience: blanked on stage, apologized, restarted cleanly
- •Audiences are typically supportive, not adversarial
- •Simple recovery tactic: pause, breathe, return to last remembered point
- •Visible imperfection can encourage others and make you more relatable
- 22:12 – 24:31
Why traditional timeline/Gantt roadmaps fail: the false certainty problem
Janna explains how she originally used and even built timeline roadmaps—until customer feedback revealed a systemic issue: nobody hits those dates. The timeline format forces artificial precision and turns a strategy conversation into a due-date negotiation.
- •Early ProdPad was a digitized timeline roadmap with drag-and-drop features
- •Customers wanted bulk-shift features because their timelines constantly slipped
- •Root cause: teams weren’t delivering to those dates; the roadmap became fiction
- •Timelines imply everything has duration/due dates, which is wrong farther out
- 24:31 – 28:04
Now/Next/Later: a roadmap that respects the cone of uncertainty (and still allows dates)
Janna describes the three-column approach (current/near-term/future) that became Now/Next/Later. It removes the default pressure to date everything, while still permitting dates when truly necessary, aligning roadmaps with real-world uncertainty.
- •Three buckets: Now, Next, Later (less certainty as you go outward)
- •Optional dates for specific items that truly require them
- •Designed to prevent “date-by-default” behavior caused by timeline formats
- •Frames roadmapping as an ordering/prioritization tool, not a calendar promise
- 28:04 – 32:57
Operating without full timelines: communication rhythms and soft vs. hard launches
The discussion tackles the biggest objection: how Sales/Marketing plan without dates. Janna proposes regular communication and separating development ‘soft launches’ from marketing ‘hard launches’ so each function can work with real artifacts and less schedule coupling.
- •Use ongoing communication and launch readiness meetings to maintain alignment
- •Soft launch when engineering ships; hard launch when marketing is ready
- •Marketing benefits from real product artifacts (not outdated design mocks)
- •Reduces stress of trying to synchronize two different project types perfectly
- 32:57 – 36:46
What great product teams do differently: discovery, psychological safety, and retrospectives
Janna shares cross-team signals of strong product organizations: continuous discovery and psychological safety to challenge assumptions and raise issues. Retrospectives are highlighted as a practical mechanism that builds safety and continuous improvement over time.
- •Strong teams invest in discovery and frequent customer learning
- •Psychological safety enables questioning across levels and reduces silos
- •Retrospectives reinforce safety and create a habit of iterative improvement
- •Avoids ‘pinning teams down’ to fake certainty for leadership comfort
- 36:46 – 40:33
Changing culture in large companies: ‘calcification,’ small pockets, and executive buy-in
Janna frames large-company culture as calcified—requiring gradual chipping away rather than a big-bang transformation. Successful change often starts with a small team or innovation pocket, then spreads through advocates, though incentives at the top can work against risk-taking.
- •Culture change is incremental: chip away rather than overhaul instantly
- •Start with a small pocket (startup lab, a capable leader, one department)
- •Advocates and multiple groups create momentum for broader rollout
- •Misaligned incentives: stability/quarterly growth vs. innovation and risk
- 40:33 – 42:05
How ProdPad reinforces better PM practice: forcing functions for outcomes and learning
Janna explains ProdPad’s philosophy: it’s not just a documentation tool—it nudges teams into better habits. The product makes it harder to default to feature+date roadmaps and prompts teams to clarify problems, desired outcomes, and success measurement.
- •Tooling as behavior design: makes timeline/feature-date habits harder
- •Prompts for problem framing, outcomes, and rationale behind ideas
- •Encourages post-delivery learning: capture results and success measures
- •Positions ProdPad as an enabler in broader transformations and maturity
- 42:05 – 53:39
Resources, vision, and founder lessons: sandbox, Geoffrey Moore template, and PM-to-founder advice
Janna shares how to start using Now/Next/Later (including a sandbox and even Post-its), then reframes roadmaps as prototypes for strategy. She closes with a product vision template inspired by Geoffrey Moore and advice for PMs aspiring to become founders, followed by a short lightning round and where to find her.
- •Try Now/Next/Later via ProdPad trial, sandbox, or simple Post-its
- •Roadmap as a ‘prototype for strategy’: value is in the roadmapping process
- •Geoffrey Moore-style vision/elevator pitch template (target, need, category, differentiation)
- •PM-to-founder: leverage cross-functional exposure, expect surprises, build an advisor network
