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Q: Paging Charity! Our industry tends to espouse the value of collaboration, but then places on pedestals the worst models of authoritarian leadership. You have a strong following of people who view you as an alternative voice to this tendency. What advice would you give to newer managers trying to promote different values? And what advice would you have for a manager who is interested in moving into the director role?<br>— Auntie Authoritarian<br>———————————————-<br>Dear Auntie Authoritarian,<br>I was going to protest that hey, do we really put the worst authoritarian leaders on pedestals? But then I remembered all the guys who get mentioned daily in the business press, and then I remembered the whole “founder mode” groan-a-thon, and well, okay. Point taken.<br>Except I don’t think it’s so much that we celebrate authoritarianism and sociopathy—none of these guys are exactly beloved—as we cultivate it.<br>The number of things that need to go right to get a business off the ground is astronomical; over 90% of VC backed startups will fail. There are exceedingly few winners, so every winner gets celebrated and venerated. We humans crave our heroes, so we bend over backwards to retcon their mythology.<br>There’s a flattening that happens, where everything ever done by a company with hundreds or thousands of employees gets rounded up and ascribed to one man (it is nearly always a man). The company becomes just an extension of his will to power in the eyes of the public and the press, and he can do no wrong.<br>This is not healthy, as you might imagine. Even Elon Musk didn’t start off like a Bond villain. He became one after many years of this slavering hero worship.<br>Being a leader or manager is about running the business<br>This is the first lesson of leadership: you have to win at business .<br>This is the number one job of every single manager, director, VP, C-level, and every staff+ individual contributor as well. Your job is to build the business and make it win. Which means wrestling with existential questions like:<br>Are we building the right thing?<br>Who are we building for, and do we know how to reach them?<br>Do we know what they want? Will they pay for it? How much?<br>Who are we competing against, and how are we positioning against them?<br>What do our users like and dislike about our product?<br>You need to be an oasis of context and clarity for the people around you, which means you need to really, truly understand the strategy, and help devise meaningful goals in that direction.<br>If you want your values to spread throughout the industry, the best thing you can possibly do is succeed and make others want to imitate you.<br>Why people become managers<br>A lot of folks go into engineering management because interactions with their own managers left them feeling devalued, unsupported, and unmotivated, and they want to make sure nobody else ever feels that way. I’ve heard a lot of managers describe the job as being “all about the people”—how they feel, how you support them, how you help remind them to go on vacations and log off at 5pm and take plenty of vacation time.<br>This is a lovely sentiment. But putting people’s subjective experience first is putting the cart before the horse. Feelings are outputs and trailing indicators, and management is about inputs.<br>I actually agree that managers have a tremendous amount of influence over how people feel from day to day, and that it matters a great deal how we feel at work. But I think people underestimate the structural influence of circumstance.<br>I have seen so many inexperienced managers reason that the problem with past jobs was that they kept having to do work over and over, or they weren’t able to choose their work with autonomy, or their manager was micromanaging. So when they became a manager themselves, they swore they would always protect their team’s ability to move on, work autonomously, and work without them hovering.<br>But their diagnosis was usually off base.<br>The problem was that they did not have product-market fit, so the solution they were trying to build kept changing, and they kept having to go back and redo discovery work.<br>The problem was that engineering was not aligned with the field on what problems were highest priority and should get fixed first.<br>The problem was that two different leaders elsewhere in the company were not aligned on what they wanted from this team, so they kept pingponging back and forth with their demands, forcing this team to pick up work and put down work.<br>The problem was not that there was micromanaging or changing plans or people getting...