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New Think about it from management's side
They only deal with developers at the beginning and end of a project. In the beginning one guy sounds confident and decisive, the other keeps talking about problems and challenges. Some time later the first guy says it's ready for pilot and the second guy says he still has questions about requirements.

I really don't need to flesh this out any more to make the point, do I?

What I can't decide is whether the first guy might be right. Fail faster ... Release early, release often ... Minimum viable product ...

We talk about doing the smallest thing that could possibly work, but when someone tries to go faster than we're comfortable with, they're reckless and overconfident.

New Different situation with this guy
He wouldn't work with anyone unless they did exactly what he told them to, started major projects completely by himself without the Chief Software Architect (me) even knowing about them, and so on.

Fail faster at this place meant hours of downtime on a Monday where each hour had at least 7 digits attached to it.
Welcome to Rivendell, Mr. Anderson.
New But what about small teams?
Remember I started this from Joel's post about getting the best developers at a very small company, where each person might be working on a project solo. In those cases maybe you don't care so much about personality and teamwork.

As for always doing things his way, which is better: a half-dozen people spending several days trying to reach a compromise on the best direction, or that same group all going in a reasonable direction set down by the most forceful personality?

Obviously someone should see those expensive Mondays you describe and do something about it. But with enough prior reputation someone could survive one or two of those as the cost of being aggressive.

New You do care about it.
Because small companies become (hopefully) big companies, and by that time the asshole is too deeply ingrained to get rid of. And now that the company is big, his asshattery is causing bigger, more expensive problems, and he isn't (supposed to be) working on solo projects any more.
Welcome to Rivendell, Mr. Anderson.
New One could argue that you should care *more* in small company cases.
While the potential damage may be greater in a larger company, in that case you have the potential to "route around the damage" by, say, getting other managers involved. When the company is small, each piece has relatively more of the company resting on it.

     Grub2 zero day bug - Hit backspace 28 times... - (Another Scott) - (20)
         if they can get to your console you have more problems than that - (boxley) - (3)
             Been there for a while longer than 2012 - (scoenye) - (2)
                 Red China is behind it. - (a6l6e6x) - (1)
                     Well, Netscreen was Chinese. Maybe someone got creative with git... -NT - (scoenye)
         Well, damn! - (a6l6e6x) - (15)
             Somebody needs to pay for it. :-( -NT - (Another Scott)
             ESR was wrong - (pwhysall) - (13)
                 It's the high notes - (drook) - (12)
                     Yeahbut... - (Another Scott) - (11)
                         Some insight, some questionable strategy - (drook) - (10)
                             Here's the thing: - (malraux) - (9)
                                 had one of those at a previous place, my last job as an FTE - (boxley)
                                 There is a connection, though - (drook) - (7)
                                     team the two tegether, that gets all of the I's dotted and leaps of faith dissected -NT - (boxley)
                                     I know more highly productive people who aren't toxic, however. - (malraux) - (5)
                                         Think about it from management's side - (drook) - (4)
                                             Different situation with this guy - (malraux) - (3)
                                                 But what about small teams? - (drook) - (2)
                                                     You do care about it. - (malraux) - (1)
                                                         One could argue that you should care *more* in small company cases. - (Another Scott)

I invited her up to my place for a little midnight bait. I said, "Come on, baby. It'll only take a few minnows." She threw me that same old line: "Not tonight, I've got a haddock."
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