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Your Roadmap Is a Lie (And That's the Point)

How should you approach roadmap planning and commitment?

Every PM has lived this moment: a stakeholder pulls up the roadmap from six months ago and asks why Feature X isn't shipped yet. The PM stammers. The stakeholder fumes. And the roadmap -- which was supposed to be a strategic communication tool -- becomes a weapon.

The roadmap debate isn't really about dates vs. no dates. It's about what a roadmap is for. Is it a commitment? A prediction? A prototype? A political document? The answer determines whether your roadmap helps your team or handcuffs it.

Janna Bastow, who literally invented the Now/Next/Later framework, calls roadmaps "prototypes for your strategy." Shopify's roadmap comes from a 100-year CEO vision. Captions runs two roadmaps -- one public, one secret. These aren't minor tactical differences. They reflect fundamentally different beliefs about the relationship between planning and execution.

Should roadmaps have specific dates and commitments, or should they be flexible, outcome-oriented documents? And what belongs on a roadmap in the first place?

The 4 Positions

1 / 4

Roadmaps Are Strategy Prototypes, Not Plans

Janna Bastow (ProdPad · Mind the Product)

Advocates: Janna Bastow (ProdPad, Mind the Product)

Janna Bastow co-founded Mind the Product and invented the Now/Next/Later framework, which has become the dominant alternative to date-based roadmaps. Her core claim is radical: a roadmap is a prototype for your strategy, and like any prototype, it should be disposable.

"The whole point about a roadmap is that it's not designed to be your plan. I think about it as being a prototype for your strategy."
Janna Bastow
▶ 00:00:00

"The value isn't in your roadmap, the value is in the roadmapping process. What you're actually doing is laying out your assumptions of the problems that you're solving."
Janna Bastow
▶ 00:00:47

The Now/Next/Later framework replaces dates with time horizons of certainty. "Now" items are well-understood problems with defined solutions. "Next" items are validated problems without solutions yet. "Later" items are hypotheses worth exploring. The resolution decreases as you move further out -- which maps to how much you actually know.

The deeper value of Now/Next/Later isn't just avoiding dates. It's forcing honest conversations about uncertainty. When a PM says "this is a Later item," they're saying "we believe this is important but we haven't validated the problem yet." That honesty prevents the most common roadmap pathology: committing to solutions before understanding problems. Date-based roadmaps make this worse because they force teams to estimate timelines for work they haven't yet scoped, which creates false confidence in both the problem and the solution.

Bastow's framework also changes how roadmaps are consumed. Stakeholders reading a Now/Next/Later roadmap understand that the level of certainty decreases as you move right. Stakeholders reading a Gantt chart assume every bar is a commitment. The format shapes the conversation.

Example: A PM using Now/Next/Later can tell a stakeholder "payment optimization is a Now problem we're actively solving" without committing to a date that becomes a political liability. They can simultaneously say "AI-powered reconciliation is a Later hypothesis we're exploring" without triggering resource allocation debates.

When This Applies

Revisit Bastow's core insight. If your roadmap is creating more conflict than alignment, the problem isn't the format -- it's the roadmapping process. Are you having the right conversations? Are assumptions being surfaced? Is the team aligned on what you're trying to learn, not just what you're trying to build?

Run Two Roadmaps -- Public (Reactive) and Secret (Conviction)

Gaurav Misra

Advocates: Gaurav Misra (Captions)

Gaurav Misra at Captions draws a distinction most product leaders miss: the roadmap based on user feedback is table stakes. Your competitors know about those same needs. The real strategic advantage comes from a separate, conviction-based roadmap of bets on where the world is going.

"We have what we think of as the public roadmap. This is basically what people have asked us for... And then they have the secret roadmap, which is completely not informed by users or data -- it's just them making bets on where the world is going."
Gaurav Misra
▶ 00:00:50

This isn't about secrecy for its own sake. It's about maintaining space for proactive, vision-driven work alongside the necessary reactive work. Most teams fill their entire roadmap with user requests and competitive responses, leaving zero room for the conviction bets that create category-defining products.

The two-roadmap approach solves a problem that most product leaders feel but can't articulate: the tension between responsiveness and vision. If your roadmap only has user-requested features, you're building a better version of what exists. If your roadmap only has conviction bets, you're ignoring the customers who pay your bills. Misra's insight is that you need both, and trying to put them on the same roadmap creates confusion about what's a commitment and what's a bet.

The secret roadmap also creates organizational space for risk-taking. Items on the public roadmap have implicit accountability -- users expect them. Items on the secret roadmap are explicitly experimental -- the team knows they might fail. That psychological safety is essential for the kind of bold product work that creates category-defining moments.

Example: Captions' public roadmap might include "better subtitle editing" (user request). Their secret roadmap might include "AI-generated video from text" (conviction bet on where video creation is heading). Both are valid. Only one is differentiated. And putting them on the same roadmap would force the team to prioritize table-stakes work over breakthrough work every time.

When This Applies

One roadmap, outcome-oriented, Now/Next/Later. You don't know enough for dates to be meaningful.

Varying Resolution -- Detailed Near-Term, Directional Far-Term

Shishir Mehrotra

Advocates: Shishir Mehrotra (Coda)

Shishir Mehrotra at Coda takes the most pragmatic approach. Plan two quarters ahead, but with different levels of detail. Q1 gets a detailed project list with clear prioritization. Q2 gets high-level bullet points that provide direction without false precision.

"It's not a committed plan, it gives the team and the broader company a look at the longer arc and helps them contextualize your current quarter's OKRs."
Shishir Mehrotraon Lenny's Podcast (balancing detail with direction in roadmaps)

The insight is that stakeholders don't actually need dates for everything -- they need enough context to understand why you're doing what you're doing right now. The far-term roadmap serves a narrative purpose, not a commitment purpose.

Example: A Coda team's roadmap might show "Launch collaborative AI features" as a Q2 bullet point, giving the company directional clarity without the false precision of "Ship AI co-editing by March 15."

When This Applies

Two roadmap styles. Vision-driven for core product. Structured and data-driven for growth.

Vision-Driven Roadmaps -- Let the CEO's 100-Year Vision Lead

Archie Abrams

Advocates: Archie Abrams (Shopify)

Shopify's approach is the most iconoclastic. Core product teams don't have metrics-driven roadmaps. Their priorities come from Tobi Lutke's 100-year vision for the company. Taste and intuition drive decisions, not quarterly OKR cycles.

"Their priorities in product roadmap are driven by a 100-year vision that comes from Tobi, the CEO."
Lenny Rachitsky
▶ 00:01:12

Importantly, this doesn't mean Shopify ignores data. The growth team has a structured, experimentation-driven roadmap. But the core product team operates from vision. This acknowledges that different types of product work need fundamentally different planning approaches.

This split is the most underappreciated organizational design insight in Shopify's model. It acknowledges that the people building the core product and the people optimizing growth are doing fundamentally different types of work. Core product teams need space for intuition and long-term thinking. Growth teams need tight feedback loops and measurable outcomes. Giving both groups the same roadmap format forces one to operate in the other's mode -- and both suffer.

The limitation is obvious: this only works with a visionary CEO who has earned the team's trust. Telling your core product team "just follow the CEO's vision" without a Tobi Lutke is a recipe for confusion and learned helplessness. But for companies that do have that leader, the vision-driven roadmap liberates product teams from the tyranny of quarterly feature requests.

Example: Shopify's core commerce tools are built toward Tobi's vision of democratized entrepreneurship, not toward quarterly feature requests. Growth experiments on checkout conversion use an entirely different, data-driven roadmap. The two teams sit in the same company but operate on different planning rhythms.

When This Applies

You need a public roadmap with time horizons (not specific dates) for customers, plus an internal conviction roadmap for strategic bets.

Evidence from the Archive

Mind the Product, ProdPad

ProdPad's first version was a digitized timeline roadmap -- users requested multi-select drag to 'move everything by...

ProdPad's first version was a digitized timeline roadmap -- users requested multi-select drag to 'move everything by a month,' revealing that no one was hitting their dates

Janna Bastow · Co-founder, inventor of Now/Next/Later ▶ Watch

Captions

Eye contact feature: Captions was the first to build AI-powered eye contact correction for video creators, working...

Captions does quarterly company-wide brainstorming where everyone (engineering, recruiting, marketing) contributes ideas and votes, feeding the secret roadmap

Gaurav Misra · CEO and co-founder ▶ 00:00:50

Coda

Coda's Dory/Pulse ritual: in every meeting and write-up, everyone writes opinions simultaneously (hidden from...

Bing Gordon (EA co-founder) articulated the golden ritual framework: Amazon has six-pagers, Google has OKRs, Salesforce has V2MOM -- each is named, known by the first Friday, and templated

Shishir Mehrotra · CEO ▶ Watch

Shopify

Shopify's core product group operates with no KPIs or metrics -- they are literally banned -- relying instead on...

Shopify's core product group operates with no KPIs or metrics -- they are literally banned -- relying instead on Tobi's 100-year vision for commerce

Archie Abrams · VP Product, Head of Growth ▶ 00:01:12

The Synthesis

The non-obvious pattern across these approaches is that the best roadmaps have multiple layers operating at different speeds and levels of commitment. No single roadmap philosophy works for all types of product work within the same company.

Multi-Speed Layers

Why does no single roadmap philosophy work for an entire company?

Process Over Artifact

Is the roadmap document or the roadmapping process more valuable?

Cadence Matters Most

What practical consequence follows from process-over-artifact?

The best roadmaps have multiple layers operating at different speeds and levels of commitment. Core product work needs outcome-oriented roadmaps with no dates. Growth, platform, and infrastructure work needs more structure and shorter time horizons. Applying one philosophy across the board is the fatal mistake.

The value is in the roadmapping process, not the roadmap artifact. The conversation about assumptions, priorities, and tradeoffs is the real product. A team that revisits and debates monthly gets more value than a team with a beautiful but static annual roadmap.

If the process is the real value, then cadence matters more than format. A regular cycle of questioning assumptions and reprioritizing is the constant across successful companies. The roadmap that sits on a shelf for six months is not a strategic tool -- it is a historical artifact.

Which Approach Fits You?

Answer 3 questions about your situation. We'll match you to the right approach.

Question 1

What stage is your product at?

Question 2

Is your roadmap creating more alignment or more conflict?

Question 3

How far ahead can you reliably plan?

Notable Absences

The Bottom Line

This process-over-artifact distinction has a practical consequence that most teams miss. If the roadmapping process is the real value, then the cadence of that process matters more than the format of the document. A team that revisits and debates its roadmap monthly is getting more value than a team that creates a beautiful but static annual roadmap. The companies cited here -- Coda, Shopify, Captions -- all have frequent roadmap review cycles. The specific format varies, but the regular process of questioning assumptions and reprioritizing is constant. The roadmap that sits on a shelf for six months isn't a strategic tool. It's a historical artifact.

And Bastow's deepest insight applies universally: the value is in the roadmapping *process*, not the roadmap *artifact*. The conversation about assumptions, priorities, and tradeoffs is the real product. The document is just a receipt.

Sources

Janna Bastow — "Building better product roadmaps | Janna Bastow (Mind the Product, ProdPad)" — Lenny's Podcast, October 16, 2022
Gaurav Misra — "How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions)" — Lenny's Podcast, March 27, 2025
Archie Abrams — "Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify)" — Lenny's Podcast, November 7, 2024