Thursday, August 21, 2008

The problem with "would you bet your job on that?"

[This was originally posted at]

Here's a story:

Bob the developer is plugging away on his feature. He's made a detailed estimate. Bob's manager, Monty, asks for the estimate. "I expect 4 weeks," Bob answers, explaining the reasons for the proposed schedule. Bob is a developer, he just wants to dutifully get the project done, and he knows that the boss wants it done yesterday.

Monty is one of those managers who can squeeze the most from his employees, so he pushes back (half jokingly) with "Really, are you sure? Would you bet your job on that?"

Visibly flustered, Bob squirms in his seat, "Um, ah, I'm not fully sure, I can recheck things..."

"Aha," Monty quietly assures himself, "No developer is going to pull a shoddy estimate past me!"

As everyone leaves, Monty feels puffed up, and Bob feels like he's not worth two cents.

I've actually seen this sort of nonsense happen before (thankfully never at Paylocity). Sure, occasionally there are do-or-die decisions where the company goes under if the wrong action is taken. But the vast majority of the time, it's a hot-shot manager thinking that they're going to show "those developers" who really sees the big picture. After all, the manager is merely asking for a proper estimate (or feature, or technical component, or bug fix, etc...).


The problem with this managerial approach is that it's not a fair wager. The developer essentially puts up $100,000 (their job, which may include benefits and multiple year's worth of work), whereas the manager only puts up a nickel. Even if the developer is incredibly confident, it's still not worth the bet.


I'm sure somewhere out there, there is a perfect comeback. The best I can think of is (1) leaving that project (with a manager like that, the project is probably doomed anyway), or (2) calling out the manager and remaining confident "No, I'm not betting my job, I'm giving you a detailed estimate. Do you think there's an error in the estimate, or would you like to shrink the feature scope?" That puts the focus back on objective facts, pulls you back to the same side (you're both working together to get the project done), shows the manager that you're above silly games, and avoids an ego match.

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