In nearly every technology project—regardless of size, sector, or sophistication—there’s a familiar tension: the need for early estimates to unlock funding and planning, versus the hesitation to provide them when many details are still unknown.
While this challenge often surfaces between delivery teams (like developers or architects) and those responsible for approvals and oversight (such as sponsors or project managers), it’s not about competing priorities. It’s about psychology—and perceived risk.
Why Estimating Early Feels So Uncomfortable
Delivery teams are typically detail-oriented and deeply committed to quality. When asked to provide estimates before the scope is clear, there’s often a strong reluctance—and for good reason.
Behavioral science offers useful explanations.
The planning fallacy, a concept introduced by Kahneman and Tversky, shows that people routinely underestimate how long complex tasks will take—even when they’ve done them before. Developers, aware of this trap, may hesitate to make the same mistake again.
Loss aversion also plays a role. The pain of being wrong—especially if it leads to blame, rework, or overtime—can outweigh the perceived benefit of estimating at all.
And perhaps most importantly, psychological safety is often lacking. When early estimates are treated as commitments rather than evolving inputs, teams don’t feel safe to guess. Estimating becomes a reputational risk rather than a planning tool.
Two Approaches That Build Momentum and Trust
At Dura Digital, we believe this common tension can be resolved—not by demanding more certainty upfront, but by shifting how we work with uncertainty.
1. Use High-Level Estimation to Set Direction
At the early stages of a project, the goal isn’t precision—it’s orientation. Tools like t-shirt sizing (S/M/L/XL), effort ranges, or confidence-based forecasting help teams express relative effort and complexity without overcommitting.
This gives decision-makers just enough clarity to support funding, scheduling, and resource alignment—without requiring every detail upfront.
2. Create a Safe Environment for Uncertainty
The more psychologically safe a team feels, the more willing they are to engage in early estimation—even when the information is incomplete.
That safety is built when leaders consistently reinforce that estimates are collaborative and provisional. This can include:
- Capturing key assumptions alongside estimates
- Reassessing effort as new information becomes available
- Focusing on learning and adjustment, rather than blame
When teams know that early estimates are a starting point—not a promise—they’re far more willing to participate in the process.
Let’s Build Better Estimation Habits—Together
Estimation doesn’t have to be a source of friction. With the right tools and environment, it becomes a powerful way to align expectations, unlock funding, and build momentum—faster.
At Dura Digital’s Business Growth Studio, we help organizations overcome this challenge by reviewing current processes, facilitating estimation workshops, and building roadmaps and project plans that reflect the realities of modern delivery.
If your team is stuck in the cycle of “we can’t estimate until we start” vs. “we can’t start until we estimate,” let’s talk. We can help you move forward—with clarity, trust, and a path that works for everyone.
