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?

— Auntie Authoritarian

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Dear Auntie Authoritarian,

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.

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.

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.

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.

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.

This is the first lesson of leadership: you have to win at business.

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:

• Are we building the right thing?
• Who are we building for, and do we know how to reach them?
• Do we know what they want? Will they pay for it? How much?
• Who are we competing against, and how are we positioning against them?
• What do our users like and dislike about our product?

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.

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.

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.

This is a lovely sentiment. But putting people’s subjective experience first is putting the horse before the cart. Feelings are outputs and trailing indicators, and management is about inputs.

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.

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.

But their diagnosis was usually off base.

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.

The problem was that engineering was not aligned with the field on what problems were highest priority and should get fixed first.

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.

The problem was not that there was micromanaging or changing plans or people getting upset. The problem was that there was no shared understanding of who made the decision, what the constraints or criteria would be involved, or who the stakeholders were—or when or if a decision had been made at all.

I believe that humane, empathetic, compassionate leaders can build a better business than sociopaths or authoritarians can. Ordering people around and treating people like objects or subjects might be effective in the short term, but they are not long term winning strategies. They do not draw people in, they do not make people feel warmly disposed towards you.

I believe people do their best work when they have agency and autonomy, when they feel creatively inspired by the work, when they feel attached to the mission and emotionally attached to their collaborators. I have experienced this for myself so many times.

But having agency and autonomy, feeling creatively inspired, loving the language or the technology, feeling attached to the mission and collaborators—these things are good, but they do not add up to “good at running the business,” ipso facto.

It is totally possible to be a humane, empathetic, compassionate, caring human being…and a really sloppy operator who is terrible at business.

Being good at running the business is not optional. The most effective leaders are the ones who are kind, caring humans and skilled business operators. The second most effective leaders are the ones who are crappy humans but skilled business operators. After that comes everyone else.

This is why I always tell new managers they should focus on learning the business. If they were an engineer, they probably love building tech and systems. If they signed up for management, they probably love running people and teams. It’s the business side that’s a real gaping hole in the track record of most new engineering managers’ experience.

You asked what advice I had for advancing to the director level. Two things. First, the hardest part may be sussing out the right opportunity. At each level of hierarchy, there are approx. 1/10th as many people as the previous level. That’s true even when we aren’t going through a prolonged phase of flattening org charts and enlarging team sizes.

Your best bet is being promoted from within; companies are usually quite resistant to hiring someone into a higher-level management role if they have not already done the role.

Second, this. Managers are notorious for thinking everyone on their team is THE BEST. Managers are always trying to insist that everyone on their team is a 5/5 or a 4.5/5, and going to bat for them to get raises and promotions every cycle. (It would be very endearing if it wasn’t so counterproductive.)

If you’re sitting here thinking, my team is awesome, they are the best, we are the best, everything is great—honey, you are not serving them well. Your job is not to be back-patter in chief.

If you really want to make your team feel good, the best thing you can possibly do for them is turn them into a high-performing team, as Patrick Lencione defines it. High-performing teams are ones people will look back on fondly and wistfully for the rest of their career. But you cannot build these teams by cheerleading. You have to nurture a restless hunger for improvement in every one of you. You have to set the pace, and show the way.

That takes systems thinking, courage, and credibility. And it is what executives look for when tapping managers to be directors.

The experiences people carry around as “the manager I never want to be” are often things like the time their project got shut down and thrown out after months of work, their team got re-orged without notice, a beloved leader got fired, layoffs happened or happened poorly, new management was brought in and wrecked a culture they held dear, etc.

We tend to blame “the manager” in these situations. Sometimes it is warranted, but more often it is not. It is often a sign of underlying weakness in the business.

Twitter had 7500 employees in 2022 when the Elon Musk hurricane blew in.

I have nothing kind to say about what Elon Musk did to Twitter. But I also look at that situation and think, “Twitter’s leaders had 16 years to figure that out, and they didn’t. It was only a matter of time before someone was going to take it out of their hands.”

Twitter’s beloved culture, its cushy policies, perks, and freebies; the work/life balance, the lengthy, consensus-based decision-making protocols and innumerable veto points, the 1700 engineers, the famously lax policies…They acted like they had won, they were comfortable. They hadn’t won.

The job of every manager is to set a high standard for themselves and their teams, to run the business efficiently and with excellence. This is how we earn the privilege of serving in our role.

If we don’t do it, it will be done to us.