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Disclaimer: I was Will's direct report, and then Will became my skip level in a past life. I'd rate him as better than average manager, who was surrounded by a lot of well under average managers. I'd love to hear longer stories on your opinion here, because I have theories on the issues with Will's advice, but nobody sees quite enough organizations to quite be certain. The more stories we hear, the more likely we are to get things right. My hypothesis is that Will's advice is a lot of recipes to create change in organizations, but lacks focus on when to apply them, and how to be sure you aren't bungling it all up by fixing the wrong problem. This makes the ideas more attractive to the dashing, aggressive, confident executive, whether he has a good pulse on the problems, or he is the kind to trust on the wrong people, and fail to see that they are building enemies (as all agents of change do), without getting sufficient number of fans in the right places. So people that like his advice will tend to fail by overstepping. I know some executive who have an entire career like this, company after company: Seeing themselves as the protagonist of every story, and acting like bulls in a china shop, therefore failing politically even if their diagnosis was somehow right, and their changes made sense. Ultimately the best advice is 'make sure your manager likes you'. Which works just as well if you are a CTO reporting to a CEO, or an engineer reporting to a line manager. It's trivially easy for executives to think this isn't the case, and then be surprised when the reorg comes. |
The gap between theory and practice - tacit knowledge - is probably a factor here. It seems quite likely that a lot of really good managers in software have theories about why they are good managers. Those theories could all easily be wrong and they are actually experts at communication or weird technical details that happen to make great managers. A manager's theoretical base is always built on a large tacit "I know how to X, Y, Z in a social setting".
If we look at this article through a very abstract lens, software managing advice fits the pattern of "at the appropriate moment, do the appropriate thing". Obviously the advice he gives is heavily tinged by the managers ability to identify the appropriate moment to do something unusual. He's pointing out some times where the appropriate action seemed to be the counter-intuitive one, which is fair and interesting. But I wouldn't ever trust a random manager to be able to pick the moment to do a counter-intuitive action; unless they were mentored with extreme care.