Rock and a hard place: why estimating turns into a squeeze play

I wasn’t ever a very good bridge player, and it’s been decades since I played. Hence, using this analogy may be stretching matters, but as is typical, I took away some key metaphors from my time with the game. One is the squeeze play, where you force your opponent to discard a vital card. It’s similar in a way to what’s called Zugzwang in chess, which describes a situation where one player is put at a disadvantage because he has to make a move, and by doing so (any move, in other words) will force himself into a weaker position.

How does all this relate to CTOs and CIOs? Consider the case of having to estimate how long a specific project will take, particularly early on, usually before any kind of detailed requirements are even remotely fathomed. Note that this kind of estimating is among the most critical activities that you and your organization will do, because it feeds into the organization’s whole prioritization and costing process as a whole. Unfortunately, it gets you into exactly this kind of squeeze situation. If you say a project is going to take what’s considered to be “too long”, you’ll get beaten down about why you can’t do it faster. If you blithely “sign up” for doing it too fast (say, as fast as they want it), there’s a huge risk that you won’t be able to deliver.

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