🎯 🤝 Building Roadmaps that don't collect dust.

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The Hard Truth About Product Roadmaps

Let’s be honest—most product roadmaps are fiction. They’re packed with hopeful guesses, political compromises, and features that will never see the light of day. By the time they’re approved, the market has already moved on.

But here’s what no one tells you: A great roadmap isn’t a plan—it’s a weapon.

The best PMs use roadmaps to:

• Force hard decisions before a single engineer writes code.

• Expose resource gaps that executives pretend don’t exist.

• Kill zombie projects that suck the life out of teams.

• Align disjointed departments around what really matters.

This week, we’re throwing out the tired advice about “keeping it simple” or “staying agile.” Instead, you’ll get:

1. The 5 Roadmap Archetypes—and which one will get you fired at your company.

2. The Stress Test that 90% of roadmaps fail

3. The Anatomy of a Killer Roadmap.

4. Real Roadmap Disasters—and how to avoid them.

By the end, you’ll have a roadmap that actually works, not one that collects dust until the next planning cycle.

Let’s begin.

🔍 Introduction

What Even Is a Roadmap?

At its core, a product roadmap is a strategic communication tool not a project plan, not a backlog, and certainly not a promise.

What a Roadmap Is (And Isn’t)

If your roadmap looks like the right column, you’re setting yourself up for failure.

Why This Matters:

67% of product teams rebuild their roadmaps every quarter because they become irrelevant (Gartner 2023). The best roadmaps aren’t just plans; they’re strategic communication tools that align teams and adapt to change.

Why Roadmaps Fail (And Why Yours Doesn’t Have To)

Most roadmaps end up ignored because they:

1. Focus on outputs (features) instead of outcomes (impact)

   • Example: "Add AI chatbot" instead of "Reduce support tickets by 30%."

2. Ignore resource realities

   • 78% of teams overcommit by 2-3x (Jira, 2023). No truer words!

3. Lock in assumptions

   • Markets change faster than roadmap cycles.

The Cost of Bad Roadmaps:

Bad roadmaps don’t just waste time—they erode trust, burn out teams, and stall growth.

• Wasted effort: 40% of features built are rarely or never used (Pendo).

• Stakeholder whiplash: Constant reprioritization makes leadership question your judgment. ("Why did you promise this if it wasn’t possible?")

• Engineer frustration: Teams slog through low-impact work while real opportunities slip away.

• Missed market windows: Rigid plans leave no room to pivot when customers or competitors move faster.

• Team burnout: Constantly pivoting [This!!!!! 😠 ]

A broken roadmap isn’t just a planning failure; it’s a strategic liability. The longer you tolerate it, the more it costs you.

The Anatomy of a Stellar Roadmap

A great roadmap isn’t just a list of features—it’s a strategic blueprint that keeps teams focused, aligned, and adaptable. Think of it like a GPS for your product: it tells you where you’re going, why it matters, and how to adjust when roadblocks appear.

Here’s what makes a roadmap actually work:

1. The Foundation: Strategic Goals

A roadmap without clear ties to business objectives is just a to-do list in disguise. The best roadmaps start by anchoring every initiative to a measurable outcome—whether it’s "Increase enterprise revenue by 20%" or "Reduce churn to under 5%." This forces hard choices upfront: If an item doesn’t directly drive a goal, it doesn’t belong.

Pro tip: Use backward planning—define the goal first, then work retroactively to identify the fewest, highest-leverage bets to get there.

• Every item must trace back to a company objective (e.g., "Increase enterprise revenue").

2. The Framework: Choose Your Type

Roadmaps come in flavors—pick the one that matches your company’s stage and culture. Early-stage startups thrive with Now-Next-Later’s flexibility, while enterprises need theme-based roadmaps to align cross-functional teams. The key is avoiding "Frankenroadmaps" that try to be everything at once.
Rule of thumb: If your roadmap requires a 10-minute explanation to new hires, it’s too complex.

5 Roadmap Archetypes

💡 Company stage dictates roadmap type more than preference.

3. The Secret Sauce: Adaptive Elements

Static roadmaps fail because reality isn’t static. Build in mechanisms for change: expiration dates, "if-then" triggers, and a public "parking lot" for ideas you’re explicitly deprioritizing. This isn’t indecision, it’s intellectual honesty. Example: A SaaS company added a "Sunset Clause" to roadmap items, auto-archiving anything untouched for 90 days. Result? 30% fewer zombie projects within a quarter.

• "If-Then" Rules: "If DAU grows <10% this quarter, we deprioritize experimental features."

• Parking Lot: A public list of what’s not being worked on (and why).

• Expiration Dates: "This roadmap is valid until Q3 pending market conditions."

The roadmap Test: (90% Fail)

Ask these five questions about your current roadmap:

1. "Could a new engineer look at this and understand how their work matters?"

2. "Does sales know which deals to pursue based on this?"

3. "If we only did 50% of this, would we still hit our goals?"

4. "What’s the first item we’d cut if resources shrank?"

5. "When was the last time we killed a roadmap item?"

Scorecard: 

0-2 "Yes" = Redo your roadmap.

3-4 "Yes" = Needs tweaks.

5 "Yes"= You’re a roadmap Jedi.

Can You Combine Roadmap Types?

Yes—but with rules. Hybrid roadmaps work when you:

1. Layer Time + Themes

• Example:

  • Q3 2024: Improve Monetization

    • Outcome: Increase ARPU by $5

    • Initiatives:
      • Tiered pricing (Aug)
      • Usage analytics (Sept)

• Why It Works: Time provides structure, themes provide flexibility.

2. Use "Horizons" for Innovation

• Now (0-6mo): Time-based (Q1/Q2) for execution

• Next (6-18mo): Theme-based for growth

• Future (18+mo): No dates, just exploratory bets

3. Segment by Audience

• Executives: Quarterly themes + financial outcomes

• Engineering: Now-Next-Later with technical milestones

• Customers: High-level public roadmap (no dates)

Warning: Avoid "Frankenroadmaps" where:

• Stakeholders see conflicting versions.

• Dates are added to speculative work.

• No one knows which layer is authoritative.

💡 Pro Tip: The "Roadmap of Roadmaps"

Document the types of roadmaps you use for which decisions:

Final Thoughts

"A roadmap is a hypothesis, not a prophecy. The best PMs spend as much time invalidating their roadmaps as building them."

Next Week: We’ll expose how top PMs say "no" without losing political capital, using prioritization techniques that actually work. 

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