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Janna Bastow (Mind the Product, ProdPad)16 October 2022

Building better product roadmaps

7Frameworks
14Insights

Episode overview

Janna Bastow explains why a roadmap should be treated as a prototype for strategy rather than a fixed delivery plan. She describes creating the Now-Next-Later framework after discovering that product teams repeatedly failed to meet timeline-roadmap dates. The conversation also covers community and conference building, public speaking, product-team culture, organizational transformation, and the transition from product manager to founder.

Key ideas

  • The value of a roadmap lies in the collaborative roadmapping process, where teams expose and test strategic assumptions.
  • Now-Next-Later reflects increasing uncertainty over time and avoids assigning artificial dates to every initiative.
  • Dates remain appropriate for genuine constraints such as regulation, seasonal demand, or the school year, but require added planning and buffer.
  • Separating a development team's soft launch from marketing's hard launch prevents two different project timelines from being unnecessarily coupled.
  • Strong product teams emphasize continuous discovery, psychological safety, retrospectives, and accountability for experiments rather than predictions.
  • Large-company culture changes incrementally: begin with a supportive leader and a small organizational pocket, then let successful practices spread.
  • Effective presentations begin with narrative and story points before slides, and improve through rehearsal, recording, coaching, and audience connection.
  • Product-management experience prepares prospective founders through cross-functional exposure, but founders still benefit from a strong network of advisers.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Leadership5 steps

Culture as Calcification: The Pocket Rollout

You cannot melt an enterprise's culture — you chip it, one advocate-led pocket at a time.

Read →
Marketing5 steps

Soft Launch / Hard Launch Decoupling

Let engineering ship when it's ready and let marketing launch when they're ready — never on the same date.

Read →
Communication7 steps

The Conference Talk Prep Loop

Narrative before slides, rehearse until it's automatic, then own the room before anyone is in it.

Read →
Strategy5 steps

The Elevator-Pitch Product Vision Template

Fill six slots — customer, need, name, category, reason to buy, differentiation — and you have a vision statement.

Read →
Strategy6 steps

The Now-Next-Later Roadmap

Replace the Gantt timeline with three confidence buckets so plans get vaguer as they get further out.

Read →
Strategy4 steps

The Roadmap as a Prototype for Your Strategy

Treat the roadmap like a design mock-up: its value is in the feedback it provokes, not the document itself.

Read →
Influence4 steps

The Sales Team Parity Argument

Ask for exactly the accountability sales gets: budget, experiments, and outcomes — not named deals on named dates.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 12

  • Janna BastowMentionsI'm a product manager by background

    “today my guest is Janet basto”

    ▶ Watch at ~1:00approx.
  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “welcome to Lenny's podcast I'm Lenny”

    ▶ Watch at ~1:00approx.
  • Janna BastowCoinedI'm a product manager by background

    “she's also the inventor of the road mapping framework now next later”

    ▶ Watch at ~1:30approx.
  • Shishir MehrotraMentionsshashir marocha is the co-founder and ceo of koda before starting koda shashir led the youtube product engineering and design teams

    “shashir the CEO of Coda”

    ▶ Watch at ~3:30approx.
  • Shreyas DoshiMentionsHe reflects on roughly 20 years in product work and leadership roles at Google, Twitter, and Stripe.

    “including resources from many guests on this podcast including shreyas Gokul and shashir”

    ▶ Watch at ~3:30approx.
  • Gokul RajaramMentionsa tactic gokule shared on this podcast about one of his best tricks

    “including resources from many guests on this podcast including shreyas Gokul and shashir”

    ▶ Watch at ~3:30approx.
  • Simon CastCoinedmentioned

    “myself and Simon my co-founder at broadpatch and we sat down and we came up with uh three column roadmap”

    ▶ Watch at ~24:30approx.
  • John CutlerMentionsI talked to John Cuddler actually and he gave me this framework that is like completely stuck in my mind

    “I'm excited to chat with my friend John Cutler from podcast sponsor amplitude”

    ▶ Watch at ~27:00approx.
  • Geoffrey MooreCoinedJeffrey is the author of maybe the most influential and important book on go to market ever written crossing the chasm

    “you might actually recognize it from the Jeffrey Morse Crossing the chasm book it's the elevator pitch template”

    ▶ Watch at ~47:00approx.
  • Neil GaimanMentionsmentioned

    “oh it is British yes Neil Gaiman”

    ▶ Watch at ~51:00approx.
  • Rob WallingCoinedmentioned

    “it's Rob Wallings podcast”

    ▶ Watch at ~51:30approx.
  • Christina WodtkeRecommendsChristina is a multi-time author, speaker, and lecturer at Stanford, where she teaches product management, game design, and a few other topics.

    “I've got to give a shout out to Christina wodka”

    ▶ Watch at ~52:00approx.

Resources · 26

  • Now-Next-LaterCoinedother · Janna Bastow and Simon Cast

    “she's also the inventor of the road mapping framework now next later”

    ▶ Watch at ~1:30approx.
  • SegmentMentionssoftware · Twilio

    “send data to destinations like postgres bigquery and segment”

    ▶ Watch at ~2:30approx.
  • BigQueryMentionssoftware · Google

    “send data to destinations like postgres bigquery and segment”

    ▶ Watch at ~2:30approx.
  • PostgreSQLMentionssoftware

    “send data to destinations like postgres bigquery and segment”

    ▶ Watch at ~2:30approx.
  • FormsortRecommendssoftware

    “you can sign up for a free account on formstore.com and use promo code Lenny for twenty percent off”

    ▶ Watch at ~3:00approx.
  • CodaUsessoftware · Coda

    “I actually use Coda every single day it's my home base for organizing my newsletter writing”

    ▶ Watch at ~3:00approx.
  • CodaRecommendssoftware · Coda

    “make your life better and start using Coda”

    ▶ Watch at ~4:00approx.
  • Mind the ProductCoinedcompany · Janna Bastow and co-founders

    “one of my co-founders who I also happened to start mine the product with”

    ▶ Watch at ~5:00approx.
  • ProdPadCoinedsoftware · Janna Bastow and Simon Cast

    “that tools that I was talking about turned into prodpad which is software for product people”

    ▶ Watch at ~5:30approx.
  • ProductTankMentionsevent · Mind the Product

    “always being there every month holding a product tank every year holding an event”

    ▶ Watch at ~6:30approx.
  • Microsoft PowerPointUsessoftware · Microsoft

    “I used to sit down with a PowerPoint and start writing my deck in PowerPoint”

    ▶ Watch at ~16:00approx.
  • jQueryUsessoftware · John Resig

    “this is all built in jQuery”

    ▶ Watch at ~24:00approx.
  • Now-Next-LaterUsesother · Janna Bastow and Simon Cast

    “people went oh wait I can just say What's Happening Now what's happening next and what's happening later”

    ▶ Watch at ~25:30approx.
  • AmplitudeMentionssoftware · Amplitude

    “I'm excited to chat with my friend John Cutler from podcast sponsor amplitude”

    ▶ Watch at ~27:00approx.
  • AmplitudeRecommendssoftware · Amplitude

    “head to amplitude.com to get started”

    ▶ Watch at ~27:30approx.
  • GDPRMentionsother · European Union

    “when gdpr came down everyone had a due date on the road map”

    ▶ Watch at ~31:30approx.
  • HSBCMentionscompany

    “take HSBC versus all the companies who are coming up with”

    ▶ Watch at ~39:00approx.
  • ProdPadUsessoftware · Janna Bastow and Simon Cast

    “you just go to sandbox.prodpad.com where it's got example versions of roadmaps best practice roadmaps that you can just start playing with”

    ▶ Watch at ~42:00approx.
  • ProdPadRecommendssoftware · Janna Bastow and Simon Cast

    “you can start a free trial in broadpad you can start playing around with it”

    ▶ Watch at ~42:00approx.
  • Crossing the ChasmCoinedbook · Geoffrey Moore

    “you might actually recognize it from the Jeffrey Morse Crossing the chasm book it's the elevator pitch template”

    ▶ Watch at ~47:00approx.
  • The SandmanRecommendstv show · Neil Gaiman

    “oh Sandman”

    ▶ Watch at ~51:00approx.
  • Startups for the Rest of UsRecommendspodcast · Rob Walling

    “ooh startups for the rest of us”

    ▶ Watch at ~51:30approx.
  • Startups for the Rest of UsCoinedpodcast · Rob Walling

    “it's Rob Wallings podcast”

    ▶ Watch at ~51:30approx.
  • Apple PodcastsRecommendssoftware · Apple Inc.

    “you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”

    ▶ Watch at ~53:00approx.
  • SpotifyRecommendssoftware · Spotify

    “you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”

    ▶ Watch at ~53:00approx.
  • Lenny's Podcast websiteRecommendswebsite · Lenny Rachitsky

    “you can find all past episodes or learn more about the show at lennyspodcast.com”

    ▶ Watch at ~53:30approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 4

Hot Take08:30

Why Running Conferences Is the Least-Lean Thing a Product Person Can Do

Bastow warns that conferences are one of the most expensive and un-lean things you can run, because you can't iterate — a mistake has to wait a full year to be fixed. She recounts caterers under-delivering, venues going bust weeks before the event, and speakers cancelling after their flights were paid for.

  • Conferences can't be run lean or iteratively; a screwed-up detail can't be fixed until next year
  • One year the caterers under-delivered, so volunteers bought out local sandwich shops and sent attendees cash cards
  • A single cancelled speaker means thousands of pounds lost on already-booked business-class flights
  • Community goodwill built up over years is what let them survive when things went wrong

“when running a conference it's one of the most expensive and unleanest things you can possibly do it's really difficult as a product person to…”

Janna Bastow · 08:30
#conferences#events#community
Hot Take25:00

Why Timeline (Gantt) Roadmaps Are Just Wrong

Bastow argues the timeline roadmap is fundamentally broken: putting time on the x-axis forces every item to be assigned a due date and duration, which assumes a certainty that doesn't exist. The further out you plan, the more you're making it up — so penalizing yourself with a date on everything is a mistake.

  • A timeline turns the roadmap into a Gantt chart with time on the x-axis and tasks on the y-axis
  • The format itself forces a due date and duration onto everything, whether or not it deserves one
  • The further out you plan, the more you're guessing
  • Dropping the timeline doesn't mean no dates — you still add a date when something genuinely needs one

“it assumes that everything that you do has a due date and a duration just by the Format of the roadmap which is painful it's…”

Janna Bastow · 25:30

“the further out you plan the more you're making it up we know this”

Janna Bastow · 25:30
#roadmaps#product-management#planning
Hot Take42:30

A Roadmap Is a Prototype for Your Strategy

Bastow reframes the roadmap: it's not a plan, it's a prototype for your strategy. Just as a design mock-up's value is in the prototyping process rather than the artifact, the value of a roadmap is in the road-mapping process — laying out your assumptions about the problems you're solving and sharing them to check you're on the right path.

  • A roadmap is not designed to be your plan; treat it as a strategy prototype
  • Like a feature mock-up you share and throw away, the value is in the process, not the artifact
  • The real activity is laying out your assumptions about which problems you're solving
  • Sharing those assumptions early and getting feedback makes the strategy stronger

“the value isn't the Prototype the values in the prototyping process the value isn't in your roadmap the values in the road mapping process”

Janna Bastow · 43:00
#roadmaps#strategy#product-management
Hot Take44:30

Product Isn't Asking for More Leeway Than Sales Gets

Bastow's argument for why fewer deadlines can fly at your company: product is the only function pinned to concrete delivery dates. A VP of Sales never promises exactly which deals will close, only that a process of experiments (calls) will hit the number. PMs should be accountable for the experiments they run, not for knowing what will work before they run it.

  • Product people are uniquely required to give concrete dates for when things ship
  • Sales promises a number via a process, not named deals — treat calls as experiments
  • PMs likewise spend a budget running experiments; some fail, some succeed, moving the numbers
  • Be accountable for the experiments you ran, not for predicting outcomes before you know them

“product people are the only ones who seem to be pinned down to be required to give concrete dates as to when things are going…”

Janna Bastow · 44:30

“you shouldn't be accountable for saying what is going to work before you know it's going to work yet”

Janna Bastow · 46:30
#deadlines#product-management#accountability

Explainer· 2

Explainer28:30

Separating Soft Launch From Hard Launch to Unblock Marketing

To ship without dated roadmaps while still serving marketing and sales, Bastow separates the developer-convenient soft launch from the marketing-driven hard launch. Development ships when ready, marketing gets a working version to make videos and gather testimonials, then plans the big hard launch on its own schedule while dev moves to the next thing.

  • Developers launch on the date convenient for them; slipping from September to October doesn't matter
  • Marketers are busy promoting last month's launches, so the exact soft-launch date is fine to slip
  • Once soft-launched, marketing has a real working version for videos and beta testimonials
  • The hard launch is then planned separately while development cracks on with the next thing

“one of the other things that you can be doing for your marketing and sales teams is separating your hard launch from your soft launch”

Janna Bastow · 28:30

“there's nothing worse than the marketers trying to Market something based on pictures from the designers that have vastly changed by the time they go…”

Janna Bastow · 29:30
#launches#marketing#product-management
Explainer37:00

Culture as Calcification: Changing How Big Companies Build

Bastow describes company culture as calcification — limestone built up over time that you can only chip away at, never fix in one go. The tactic is to find a small pocket with a capable leader, let them prove the new way of working, then spread it section by section. But it requires buy-in from above, whose incentives are often misaligned.

  • Culture is like calcification: you chip it off over time rather than fixing it all at once
  • Start with a small pocket or 'startup lab' led by someone who knows what they're doing
  • That pocket teaches the next section, and the next, rather than a company-wide change
  • It needs top-down buy-in, but leadership incentives to keep the company stable often work against it

“I think of culture as calcification so calcification being the Limestone that you know is built up”

Janna Bastow · 37:00

“you don't have to go and change the whole company all at once but it does take buy-in from above”

Janna Bastow · 38:00
#culture#change-management#enterprise

Story· 3

Story06:00

How Mind the Product Grew Into the World's Largest Product Community

Janna Bastow explains that Mind the Product was never designed as a community-building play. It started as a few product people getting together to learn from each other, and grew through relentless consistency and by recruiting others to curate speakers and content beyond the founders' own network.

  • The community began from a sense of sharing and learning together, not a deliberate strategy
  • Consistency was the key input: holding a product tank every month and an event every year
  • The founders' own network was limited, so they recruited others to find speakers and blog writers
  • Mind the Product was sold earlier in 2022; at peak, ProductTank ran in nearly 300 cities worldwide

“it wasn't so much that we set out to build a community it was that we got together with some product people with the idea…”

Janna Bastow · 06:00
#community#product-management#founders
Story19:30

Blanking in Front of 200 People — And Why the Audience Is Rooting for You

Bastow tells the story of freezing and forgetting everything in front of 200 people at an early ProductCamp. She simply apologized and started over, and the audience was completely fine with it. The lesson: people are rooting for you, and screwing up on stage is humanizing rather than fatal.

  • At an early ProductCamp she tripped over her words, blanked, and restarted from the top
  • The audience didn't think anything of it and just rolled with it
  • The feared worst-case scenario almost never actually happens
  • If you freeze, take a breath, pick up where you last remembered, and keep going

“people in the audience are rooting for you like they they were totally cool with this they didn't think anything of it”

Janna Bastow · 20:30
#public-speaking#confidence#storytelling
Story24:30

The Customer Feedback That Killed the Timeline Roadmap

Bastow recounts how early ProdPad customers kept asking to shift all their roadmap items over by a month. Instead of just building bulk drag-and-drop, she asked five whys and discovered no one was actually delivering roadmaps on the dates they set — which raised the question of why a dated roadmap existed at all.

  • Early ProdPad was a digitized timeline roadmap with drag-and-drop items
  • A month in, customers kept asking to move everything over by a month
  • Digging into 'why' revealed nobody was hitting the dates on their roadmaps
  • That insight led her and co-founder Simon to the three-column now/next/later structure

“we found out that no one was actually delivering the road map in the time frame that they were saying they were”

Janna Bastow · 24:30
#roadmaps#customer-discovery#product-management

Q&A· 1

Q&A49:30

Advice for PMs Who Want to Become Founders

Asked what PMs aiming to be founders should work on, Bastow says the PM role already builds much of the needed background — cross-team exposure and seeing how a business works up close. Founding is both easier and harder than it looks; the key is to surround yourself with people you can go to for each type of problem and figure it out as you go.

  • Being a PM gives you exposure to many teams and the underpinnings of how a business works
  • Founding is not as hard as it looks — no one stops you and there's lots of freedom and resource
  • It's also harder than it looks: unexpected problems will sideswipe you, just as in a PM role
  • Surround yourself with people so you have someone to go to for each kind of problem

“certainly don't stop yourself from starting a business or starting your own thing just because you don't think that you know how to do it…”

Janna Bastow · 50:30
#founders#career#product-management

Tool· 1

Tool47:30

Use the Crossing the Chasm Elevator Pitch Template for Product Vision

Bastow's go-to for articulating a product vision is the elevator pitch template from Geoffrey Moore's Crossing the Chasm. It answers the same questions a vision needs: target customer, statement of need or opportunity, product name and category, reason to buy, the alternative it's unlike, and the statement of differentiation.

  • The template comes from Geoffrey Moore's Crossing the Chasm elevator pitch
  • It prompts: for [target customer], who [need/opportunity], the [product] is a [category]
  • It continues: [reason to buy], unlike [alternative], our product [differentiation]
  • It overlaps with a positioning exercise, so positioning work can feed the vision

“you might actually recognize it from the Jeffrey Morse Crossing the chasm book it's the elevator pitch template”

Janna Bastow · 47:30
#product-vision#positioning#frameworks

Takeaway· 3

Takeaway16:00

Write the Story First, the Slides Second

Bastow shares what a Mind the Product speaker coach taught her about presenting. The biggest habit change was to stop opening PowerPoint first — instead she starts from story points and narrative, then builds slides to follow, and forces herself to record and replay her talk despite hating it.

  • She used to start in PowerPoint and bend her narrative to fit the slides; now she starts with story points
  • A great narrative should come first and the slides should follow naturally from it
  • Recording yourself and playing it back is uncomfortable but improves delivery
  • For a big talk you should be able to deliver it flawlessly in the shower and on your walk to work

“now what I now do is I start with my story points I start with my narratives I try to figure out what I'm actually…”

Janna Bastow · 16:00
#public-speaking#storytelling#communication
Takeaway16:30

The Power Pose and Talking Only to Your Fans in the Audience

Bastow offers concrete stage-nerves tactics: strike a power pose with hands on hips before going on, walk the empty stage the day before during the tech check, and once presenting, ignore the disengaged people and deliver your whole talk to the few audience members who are nodding and smiling.

  • The power pose (hands on hips) genuinely boosts confidence before going on stage
  • During the tech check, walk the empty stage and imagine it full to reduce next-day stress
  • Some audience members will be on their phones — ignore them
  • Find the people nodding and smiling and deliver the talk to them; no one notices

“one of the things that actually really does work is the power pose standing with your hands on your hips and it really does”

Janna Bastow · 16:30

“find the people who are nodding along and smiling and going yeah yeah that's me that's me and just speak to them”

Janna Bastow · 18:00
#public-speaking#confidence#stage-craft
Takeaway34:30

Discovery, Psychological Safety, and Retrospectives Separate the Best Teams

Beyond process, Bastow points to two things that mark the best product teams: a focus on discovery (spending time asking customers questions and iterating) and psychological safety (people feel free to question decisions at any level). She names retrospectives as the single highest-leverage practice because they are indicative of that safety.

  • The best teams spend real time in discovery, constantly iterating on customer input
  • Psychological safety lets people question decisions across teams and seniority levels
  • Retrospectives make a big difference because they signal psychological safety
  • Teams with these traits naturally drift toward discovery and now/next/later on their own

“retrospectives make such a big difference because they are indicative of psychological safety which underpins so much”

Janna Bastow · 35:30
#product-teams#psychological-safety#discovery