Product Roadmaps: The Good, The Bad, and The Ugly

The energy in the room is growing. Sales Kickoff is in full swing. Big music, big energy, bigger targets.

And now, the room quiets. It’s time for that moment… “Let’s welcome our Chief Product Officer, here to walk us through the roadmap.”

There’s polite applause, a few hopeful smiles, and more than a few sales execs already drafting emails for features that haven’t even been mentioned yet.

The CPO steps up. Smiles. And takes a breath.

Because the roadmap slide isn’t just a slide. It’s loaded. Not just with dates and features, but with expectations, assumptions, interpretations, and more than a little wishful thinking.

Here we go.

Before the roadmap ever hits the screen…

The truth is, the roadmap doesn’t start the week before SKO. It doesn’t get thrown together in a panic to fill a slide deck.

It starts months earlier. In messy workshops, multiple review meetings. In conversations with customers, colleagues, and cross-functional teams.

Throughout the year, product, design, engineering, sales and professional services have been working behind the scenes, sometimes in heated debates to understand which problems actually matter. Not the loudest complaints or the biggest client requests. But the real, valuable, meaningful problems customers face. The ones that are worth solving.

That discovery work looks different in every company. It might be customer interviews. It might be ethnographic research, co-discovery sessions, field observations, or digging through data. It’s not glamorous, but it is foundational.

And what comes out of that work isn’t just “ideas.” It’s alignment. That’s where the roadmap earns its value. Not from what's on it, but from the thinking behind it.

The Good

So when a roadmap is rooted in that kind of deep, collaborative effort, it shows.

It becomes more than a list of features. It becomes a story. Something that helps teams step back and remember why we’re all here.

Sales gets clarity. Engineering gets purpose. Leadership sees a plan that’s grounded in reality, not just ambition.

And when it works, it works well. Everyone feels like they’re pulling in the same direction. Not because a slide told them to, but because they were part of the thinking that developed it.

The Bad

But this is also where things can start to go wrong.

Because the moment that roadmap hits the big screen, with quarters, dates, feature names. It transforms.

What was meant to be a directional guide now feels like a delivery schedule.

What was “we’re exploring this in Q3” becomes “we’re shipping this in Q3.”

And just like that, discovery becomes delay. Trade-offs turn into excuses. And suddenly the roadmap starts driving decisions instead of reflecting them.

You start building for the roadmap, not for the customer. And that's when things get sticky.

The Ugly

And then there’s the ugly version. The version no one wants to admit, but many of us have seen.

The roadmap that gets tailored to please a room. That’s shaped more by internal stakeholder pressure or big-client demands than by customer insight or product strategy.

Features get added because someone “needs something to show.” Priorities shift to win a deal. Teams get blindsided because they weren’t in the loop.

And suddenly, that roadmap isn’t guiding anyone. It’s covering tracks. It’s setting unrealistic expectations. It becomes theatre.

And eventually, that catches up with you. Sales gets frustrated. Customers feel misled. Trust breaks down. And the roadmap, once a symbol of alignment, becomes a source of tension.

What great product leaders do

The best product leaders I know don’t use roadmaps as a shield or a showpiece. They use them as a conversation. Easy to say, sometimes very difficult to do.

They walk into SKO and tell the real story. They explain how the roadmap came to be… the discovery work, the customer insight, the messy, iterative journey of figuring out where the value lies.

They are clear about what’s in flight, what’s still being explored, and what might change and why that’s not failing, but a sign that we’re still learning.

They talk about value. Not just for the business, but for the people using what we build. And they remind the room: when we get that right, the business value WILL follow.

Final thought

At the end of the day, a roadmap isn’t just a plan. It’s a reflection of how your company makes decisions. How it listens. How it learns.

If it’s built with care, shaped by real insight, and shared with honesty, it becomes one of the most powerful tools you have.

If it’s not, it’s just a slide with some boxes and dates.

So when you step up at SKO or whenever you are asked to share the roadmap… take a moment. Share the story behind the roadmap. Invite people into the thinking. And remind them: the map may change, but the intent stays the same.

We’re here to solve meaningful problems that delivers real value for customers.