How do you know if a product strategy is working?

THE SHORT ANSWER

A strategy is working when it produced a no this week that cost something a named person wanted. Tim Herbig's test, per Aakash Gupta's October 14, 2026 write-up, is whether most of the team's energy goes to work connected to the strategy. That is an input measure and it passes when the strategy was never asked: I said yes to 39 agent builds in 80 days, every one connected to the plan and minutes to build, and 13 ended with zero references anywhere else in the system. Keep a ledger of the nos with the date, what was refused, who wanted it, what it cost, and what it protected, published next to the yes count and its orphan rate. Use Roger Martin's flip to test whether a strategy line can produce a no at all.

Herbig's test for a strategy line is right: if the opposite is stupid, it was never a choice. His test for whether the whole strategy is working is the one I would replace, because mine passed it for an entire spring in which the strategy refused nothing and 13 of 39 builds ended up as orphans.

The ledger format, the flip applied to the two lines most AI strategy decks open with, and why three writers landed on the same point in one week are in A Strategy Is Working When It Said No This Week. Count the Nos.. The loop that fills the ledger is One Problem a Week, and the 39 builds are counted in Twenty Minutes Is Not a Reason to Build.

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THE LONG VERSION

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Last reviewed 2026-10-16 · 1 min read