Adaptive Planning

Preparation Is Where Adaptability Comes From

Projects rarely fail because the original plan was imperfect. They fail when the team has no way to respond once reality starts editing the plan.

Ben Griswold
Ben GriswoldAugust 11, 2025 · 2 min read

No meaningful project runs on the plan you wrote at the start.

That does not make planning useless. It makes preparation more important than prediction. The point is not to guess every surprise in advance. The point is to build a team that can absorb the surprise without turning every change into a new emergency.

Endurance racing makes this obvious. You train, pack, study the route, and still end up with two right socks or a dead watch. The question is whether that breaks the race or just becomes part of the race. Technology work is not different enough to make the analogy cute. Budget cuts happen. Scope changes. A key person leaves. A vendor constraint shows up late and acts like it was there the whole time.

Teams that survive those moments usually did the boring work early. They understood the mission. They knew what to measure. They had support outside the person carrying the most load. They treated rest as part of capacity instead of a reward for exhaustion.

Execution gets the drama, but discovery and preparation decide how much drama the team has to endure.

The broken watch is not the problem. The problem is building a delivery model that needs the watch to work perfectly.

Related episode: Two Right Socks and a Broken Watch... Consulting Lessons from the Trail.