Raise your hand if you’ve ever had a conversation like this: “We would have loved to bring in a woman [fill in the blank: on the management team, as an independent director, as our new Partner] but we couldn’t find one.
Enough is enough; let’s go 50/50.
C.A. Webb

They don’t care that they don’t look.

They don’t care that they don’t know how to look. It’s ludicrous that outcomes would change unless attitude does.

I once worked for a startup whose CEO insisted that he was technical and would serve as a filter for tech candidates because “you’re already working so hard”. The one candidate who we hired based on his filtering turned out to be a disaster, and it was only three full years on that the reasons became inescapable: instead of filtering for the needs of the team, the needs of the company, he filtered for guys he could wow with his spiel and who were culturally, ethnically, linguistically more like him than like our customers or our team to date — and that caused us to blow our market window through a combination of egregious understaffing and enforced equally egregious overwork that led to serious health issues, followed by burnout that incapacitated me for well over a year. “If you’re working more than 40–45 hours a week, you’re kidding yourself” is something that both the science folks and successful software folks have been telling us for decades, and yet the Sili Valley mythology of the Hero Programmer and of the mythological startup that cracks 100-hour weeks for a year and Gets Shit Done. If you work 100-hour weeks, or even 60, you’re getting shit done, all right, but that’s a qualitative assessment rather than a colloquialism. If you keep that up for a year, you’ll lose all your good people who can leave, will leave; and the people you have left are too insecure about their abilities to find more sane employment and/or too shell-shocked/burnt out to be even minimally creative.

I learned a lot on that job, after having already put over 30 years into my software-development career. A lot of what I learned was Neat Tech Stuff, but I would have learned most of that anyway, given the nature of the craft and the pandemic of change rampant at the time. I’ve also become far less trusting of and impressed by amazing ideas and compelling presentations: I hear your value proposition, now convince me you’re not just smoke and mirrors. At the last consulting project I had before taking that position, people called me that Russian writer (my actual background is Scot/Dutch/First Nations) because “you’re always warning about the worst possible case, in a very pessimistic way”. Sometimes that’s a very useful thing.

Getting back to diversity: one of the things I relearned at that self-labelled startup is that when you don’t hire people unless they think like you, talk like you, look like you…you’ll run into a situation where none of your team will be able to see a solution to a problem that’s stopped you cold. Companies have been known to die of such diseases, and not all of them were three-guys-in-a-garage startups. We can, should, and must do better.