When teams lose sight of the user, the roadmap starts lying to you

There’s a moment I’ve seen in many growing teams and companies. Work is getting done, sprints are full, the roadmap keeps moving and yet something feels slightly off. Progress is happening, but the connection to the user’s reality feels thinner than it should.

It’s subtle at first, but once the user shifts from a daily reference point to an occasional consideration, decisions start happening inside a vacuum. That’s when the roadmap stops telling the truth about what actually matters.

I’ve watched this happen in early stage companies and in large organisations. And in many conversations with founders, the same worry always surfaces: the team is capable, but not as close to the user as they used to be. When that happens, alignment slips quietly in the background.

How drift happens

It rarely begins with a big mistake. It starts with small compromises, fewer discovery calls, research postponed because delivery feels more urgent, assumptions replacing real user behaviour.

From the outside, everything still looks productive. Internally, things start to feel harder to explain, decisions take longer, prioritisation feels shaky and features that seemed promising land without much impact.

Founders can sense this drift even if they can’t articulate it. They’ll often say, “We’re building, but I’m not sure we’re building the right things.”

That is the User Distance Problem, it grows quietly until outcomes reveal the gap.

What it looks like

When teams lose proximity to the user, a few patterns appear almost everywhere:

• Priorities are chosen based on intuition rather than recent insight.

• Conversations focus more on internal opinions than observed behaviour.

• Features are measured on delivery instead of impact.

• The reasoning behind roadmap items becomes harder to defend.

• Debates stretch on because no one has current user evidence to anchor decisions.

None of this means the team is failing, it simply means the foundation they’re making decisions on isn’t as fresh as it needs to be.

Why it matters

A roadmap not grounded in user reality doesn’t just become inaccurate, it becomes misleading. You get the sense of progress without the substance, momentum without direction, activity without learning.

Teams still work hard, but the product stops moving forward in a meaningful way.

Founders feel this shift first: that uncomfortable sense that something is off, even if nothing looks obviously broken.

A simple test

Ask yourself one question: when was the last time your team heard something from a real user that changed a decision?

If the answer isn’t “recently”, the roadmap is operating on memory, not insight.

And memory fades fast in a scaling team.

The good news

You don’t fix this with a six-month research project, the fastest improvements come from a few lightweight product habits:

• Weekly user touchpoints, 2–3 short conversations or calls, enough to keep the team anchored in real behaviour instead of internal opinions.

• A living, current definition of your core user, not personas from two years ago. A simple, shared description of who you are building for today and what matters to them right now. This alone eliminates 30–40% of roadmap debates.

• A clear value proposition you revisit every quarter: teams drift when the “why” becomes stale. When you keep the value prop current, prioritisation becomes dramatically easier.

• A decision rule that forces proof: before adding something to the roadmap: “What user behaviour change are we expecting, and what evidence points to it?” This one habit prevents feature bloat more than any prioritisation framework.

• Small, fast learning loops: before building big: prototype, test a slice, validate a behaviour. Teams that learn weekly outrun teams that ship blindly every month.

Once teams reconnect with users, everything sharpens. Prioritisation gets easier, debates shorten, and the roadmap becomes honest again.

If this feels familiar, you’re not alone. Almost every scaling company hits this point at some stage. It’s a sign that your team needs a clearer system for staying close to the user as complexity grows.

If you want to see how this shows up in your own product organisation, you can get a quick diagnostic here: Find your Product Chaos Score with the Tech Chaos Scorecard