Scoping at the start of a project is messy. The clock is ticking, the right people aren’t always in the room, and the deliverables are more sketch than blueprint. Still, an estimate is expected because someone has to decide whether to move forward.
Breaking the work into tasks and hours at this point creates the illusion of precision. What proves more useful is mapping the terrain: which deliverables feel well understood, which ones carry fog, which ones demand coordination across half the org. That map does not deliver a tidy number, but it does reveal where confidence exists and where risk is hiding.
As you move into more senior roles, you learn to live with this ambiguity. Context, architecture, operating models, all of it evolves in parallel. Estimation shifts away from calculating effort and toward sensing readiness. Are people aligned? Do they even share the same picture of the work? Those judgments shape reality far more than any hour count.
When ambiguity is high, my goal is not to pin down a number but to get a feel for shape and scale. T-shirt sizing helps make that conversation concrete. Labeling work as Small, Medium, Large, or XL captures a mix of effort, ambiguity, and dependency. A Small might be well understood and contained within one team. A Large might involve multiple teams, unclear ownership, or unknowns that will only surface once the work begins. My goal is not clarity not precision. As understanding grows, sizes can shift, and plans can adapt without pretending that certainty ever existed.
In this environment it is more about being honest about what is solid, what is shifting, and how the work is likely to change once it starts to move, and taking those factors into account when estimating.
