How to Spot a Broken Roadmap

And what it tells you about your product leadership

Not all broken roadmaps look broken. Some are beautifully organized. Clean formatting, clearly defined themes, and nice alignment to company OKRs. They make for a great board deck. They check all the boxes. But if you look closer, something’s off. The roadmap is full, but the business isn’t moving. Revenue is flat. Engagement is stalled. Engineering is delivering, but it doesn’t feel like anything is landing.

When I am brought in as a fractional Chief Product Officer, this is one of the most common scenarios I encounter. The team is shipping. There’s activity. But the roadmap isn’t working. Here’s why, and what you should do about it.

Roadmaps Are a Mirror of Your Strategy

Let’s get this out of the way: the roadmap isn’t the strategy. But it’s one of the clearest signals of whether a strategy exists. Because the roadmap shows what you're willing to spend on time, people, and risk tolerance.

So when I look at a roadmap, I’m not just scanning for features, I’m looking for signs of strategic health:

• Are we solving real customer problems?

• Are we placing meaningful bets?

• Are we investing in the future or just reacting to the present?

When those signs are missing, it’s usually because the roadmap is broken. And a broken roadmap means the strategy itself is lacking.

The Telltale Signs of a Broken Roadmap

Here are the patterns I see again and again:

1. No Real Tradeoffs

If everything made the cut, you probably didn’t prioritize. You compromised.

Great roadmaps are full of painful “no’s” that make the “yes” decisions count. If nobody is upset, you’re not being bold enough.

2. Everything Is Low-Risk, Low-Reward

You’re building lots of things that are easy to ship and unlikely to move the needle. This shows up as:

• Lots of UX polish and edge-case fixes

• Minor enhancements to mature features

• Rebuilding tools customers already tolerate

These aren’t inherently bad. But if that’s the majority of your roadmap, you’re not playing to win, you’re playing not to lose.

3. No Clear Company Bets

You ask the team what the company is betting on this quarter, and you get blank stares or five different answers. High-performing product organizations are built around having focus.

There should be 1–3 clearly articulated, company-level product bets. If those don’t show up on the roadmap, you’re either not making them or not backing them.

4. PMs Can’t Explain the “Why”

If you ask a PM why something is on the roadmap, and they say:

• “Stakeholders asked for it”

• “Sales said it was blocking deals”

• “It’s part of the quarterly OKRs”

That’s a red flag. They’re not thinking like product leaders. They’re acting like backlog managers.

Great PMs can explain how each roadmap item ladders up to a customer problem, a business opportunity, and a strategic outcome in plain English.

The Three-Bucket Roadmap: A Simple Framework

One of the fastest ways to stress-test your roadmap is to run it through the Three-Bucket Framework:

1. Defend: Things you must do to protect your current business; infrastructure, compliance, customer retention work, etc.

2. Expand: Efforts to deepen value with your current customers, increase engagement, cross-sell/upsell features, and reduce churn.

3. Explore: Bets on new value, new segments, new products, and new capabilities that could create future growth.

Now go through your roadmap and label each item. If everything is in the "Defend" or “Expand” bucket, you’re not building a future.  You’re just protecting the present. If “Explore” exists, but gets deferred every quarter, you’re not committed to growth. You’re just pretending to innovate.

Healthy product orgs have a portfolio. They don’t put all their chips in one bucket, and they don’t fear risk, they manage it.

Why This Happens: Executive Avoidance

Let’s talk about the real reason roadmaps break. It’s not your PMs. It’s not your engineers. It’s not JIRA. It’s executive avoidance. At some point, your leadership team stopped making the hard decisions. Or never started.

• You didn’t define clear product bets.

• You prioritized harmony over clarity.

• You kept saying “maybe” when you needed to say “no.”

That ambiguity trickles down into the roadmap. The product team fills the vacuum with what’s safe, what’s expected, or what’s politically least painful.

The result? A roadmap that looks busy but doesn’t build momentum.

How to Fix It

If you're in the C-suite or leading product, here's what to do next:

1. Declare Your Bets

Sit down with your exec team. Ask: “What are the 2–3 product bets we’re willing to stake this quarter on?” If you can’t name them, you don’t have a product strategy.

2. Re-score the Roadmap

Take every item on the roadmap and tag it:

• Defend

• Expand

• Explore

What’s the mix? What’s missing? What’s overrepresented? Then ask: does this mix match our strategy?

3. Re-empower Your PMs

Make it clear: PMs are not ticket-takers. They are problem-solvers and customer advocates. Help them connect roadmap items to what and why it matters, and permit them to say no to noise.

4. Commit to Risk

Not recklessly. But intentionally. Innovation isn’t magic. It’s a portfolio. You will have misses. But you will never build something transformative if you’re not willing to bet.

Final Thought: A Roadmap Is a Leadership Tool

Your roadmap is more than a plan. It’s a leadership signal. It tells your team what matters. It shows them where to focus. And, it reflects whether your company is bold enough to build the future or just trying to protect the past. So next time you're reviewing the roadmap, don’t ask “Is this realistic?” Ask: “Is this worth it?”