The Roadmap Estimation Crisis That Shook My Confidence
Engineering estimation failure has a specific chill, and I felt it in one brutal QBR. I was an engineering leader overseeing several product teams, presenting a roadmap that I knew, deep down, was fantasy. We had spent a single "planning week" hammering out estimates for a dozen initiatives, all loosely defined, all jockeying for priority. The slide deck looked polished, but I had almost zero confidence it would survive first contact with reality.
In that moment, looking across the table at executives, customer success, and sales, all hungry for clear answers, I realized the process was broken. We were betting the company's commitments on a handful of hurried conversations and gut feel. The teams deserved better, and so did the stakeholders who relied on us. Talk to any engineering leader in our industry and you'll hear the same worry: confident roadmaps are the exception, not the rule.
Why Quarterly Planning Weeks Fail Engineering Teams
The cadence was always the same: pile up projects, squeeze definition work into whatever fragments of time the teams could spare, then demand firm estimates by Friday. We asked teams to predict the unknown. They had barely any discovery time. Naturally, the numbers skewed optimistic, dependencies went unnoticed, and scope risk hid in the corners. By the time Sprint Two arrived, we were already renegotiating deadlines.
Every quarterly planning week was supposed to give us a confident roadmap planning baseline. Instead, it turned project estimation into a guessing game. We over-indexed on slide-ready narratives and under-valued the messy validation steps that make engineering estimation honest.
Because the estimates were generated in a single burst, we never had a living picture of capacity. Each new idea required heroic reshuffling. Stakeholders lost faith. Engineers dreaded planning week because it meant context switching into a thicket of half-baked projects. We were burning trust with every update.
That churn set the stage for what came next: every review felt like a test we were destined to fail.
When Roadmaps Lose Credibility With Stakeholders
The most painful part was the cascade of follow-up conversations. As soon as one project slipped, I could see eyes in the room asking, "What else is inaccurate?" One missed commitment can be explained away; a pattern signals that the process itself is unreliable. That erosion of trust is slow, but it is devastating. Teams stop raising risks because they feel doomed to disappoint. Stakeholders start gaming the system, inflating requests just to get a slice of the pie.
Within one quarter, six of the eight initiatives on that deck slipped by at least a sprint. I remember the humiliation of returning to the same stakeholders with yet another revised timeline. No matter how carefully I framed the changes, the real message they heard was, "You can't count on us."
The Personal Toll of Low-Confidence Planning
Those quarters took a toll. I lost sleep rerunning scenarios in my head, hoping I hadn't overlooked a critical dependency. I spent evenings drafting mitigation plans instead of finding clarity with the teams. Worst of all, I watched talented engineers question their own execution because leadership kept announcing targets we could not hit.
The irony is that everyone involved wanted the same thing: honest visibility and predictable delivery. But our rituals were tuned for speed over truth, and the debt piled up. Confidence became a fragile veneer rather than a shared reality, and every roadmap planning conversation felt like we were stacking cards on a shaky table.
Why I'm Telling This Story About Estimation
I'm sharing this because the pain wasn't isolated. It was systemic, grounded in the way we treated estimation and capacity as chores instead of continuous practices. If you recognize yourself or your teams in this story, know that you are not alone. Many of us have stood in front of a roadmap we did not believe in and felt the weight of letting people down.
This essay is about that feeling and the cost it carries. In my next post, I'll talk about the practices that pulled us out of the spiral and what finally restored confidence for our teams and stakeholders.
Until then, the ScopeCone homepage has a short overview of the iterative planning rituals we're rebuilding, for anyone who wants a preview of the direction we're heading.