The hardest management problem in tech

December 5, 2018

Abstract multi-coloured painting

Photo by Steve Johnson.

The hardest management problem in tech is spackle

We work with a lot of tech companies and there’s a pattern that comes up over and over. We’ll be talking about 1:1s, or feedback, or putting someone on a performance plan. These are the things that get a room full of managers to sit forward in their chairs. Voices get quieter and, if you pay attention, you can feel the temperature of the room go up.

We talk about little things. Like why you choose the seat facing the (inevitably) glass walls instead of your direct report. (Because if they need to cry it shouldn’t be on display). Or why you ask “Anything else?” (Because many things won’t get added to an agenda ahead of time. Because sometimes they aren’t sure if they’re going to say them or not.)

But we also talk about big things. Like how to give feedback that is direct and unflinching, without making it an attack. Or how to promote someone. Or how to establish and negotiate expectations for a new hire coming into a role. Or what it feels like when you fire someone.

And that’s when someone says it.

“Our office meeting rooms aren’t very soundproofed.”

Sometimes it comes out almost as a gotcha. Like: yes, those techniques and management tools are all well and good, but they won’t work here. Our meeting room walls are thin and our drop ceiling is missing a tile. So we go to a coffee shop. And a lot of the stuff you’re talking about can’t happen in a coffee shop.

Now, my favourite version of “There’s a Hole in the Bucket” is Odetta and Harry Belafonte doing it live. But whichever version you like, the punchline doesn’t change: “Then fix it, Dear Henry.”

In most tech companies, an average fully-costed employee is north of $100k/yr. Often well, well, well north. Fixing the meeting rooms so your people can develop some psychological safety? Hell, even total demolition and rebuild is a drop in the bucket. 

But you know, no one ever argues the cost of it. They just hadn’t considered that this was a problem they could fix before. The walls were a given. A constant to navigate around, not a part of the culture of the business. When you point it out to them, they get a faraway look and nod and say, “Yeah. Let’s fix that.”

Maybe your office has the same problem. Or maybe for you the walls are a metaphor. Do you have some other thing you’ve been assuming is constant, but is actually negotiable? Either way, we recommend everyone go listen to Odetta and Harry again.

— Melissa & Johnathan


What Melissa’s On About

When the Tech Mythology Collapses
The dangers of unleashing unmitigated goodness on the world

Last week I left the house for an evening event at a fancy law firm. We’ve talked about it before. I’ve got a fondness for my couch that borders on unhealthy. I’m writing this right now from said couch. But every so often it’s good to get out of the house and go see the world. And despite my tendencies toward introversion, I’ve got a good friend who goes to all the parties, is part of all the clubs, and is chair of all the committees. So when she messaged to see if I wanted to go to a panel about cannabis legalization, I said sure. 

“I expect I’ll be a pretty soft audience,” I joked. “After all, I did live in San Francisco for most of my adult life, and in the Haight for a good chunk of that.”

I went expecting to nod a lot. But I didn’t…

The first thing I noticed was that the panel was all dudes. The second thing was that while delivering quick bios, it became clear these folks do business together – either in the form of partnerships or more explicitly as investors. I leaned over and whispered the third thing to my friend, “This panel has no tension. All of these people agree with each other. No one here is going to dissent.

There’s nothing worse than a panel where everyone agrees. What the fuck is the point of the panel if we all just nod at each other? Worse than all agreeing, this panel couldn’t come up with a single potential downside about the legalization of cannabis. The uncontested message from the group was that this was an unmitigated win with zero potential downsides.

I come from tech and I’ve grown highly suspicious of unmitigated wins with zero downsides. These wins are at best under-examined and at worst catastrophic. In 2007, I was building the web at Mozilla. I could only see the amazing power of a more connected world. That foregone conclusion limited my own exploration. I was late to think about weaponization – and while there were sinister parts of the web back in the early 2000s, my energy was elsewhere.

Alexis Madrigal has a piece in The Atlantic about what happens when tech’s mythology collapses. Christina Farr has a CNBC piece about quitting Facebook and Instagram and how she’s happier without them. The Verge has a piece on how cell phones might be great or really awful for kids but the debate about kids and cell phones is universally awful for parents.

Whatever you’re building right now, be it pot or tech or scooters, I encourage you to get skeptical about unmitigated good. Get creative. Extend your timeline. Bring in people who don’t look like you. Put people on your panel who are likely to dissent. Find the tension.


What Johnathan’s Reading

Jason Fried, On being a bad manager

Jason Fried seems like a sensible person and I’ve enjoyed his writing on management before. This is a quick little 5-minute jaunt he wrote over a year ago, but it’s still mostly good. It’s an essay about why there are so many bad managers, and why there seems to be an evergreen supply of new bad ones. For those of you who like excerpts,

“But professional managers don’t start as managers. They’re generally promoted to management. They’ve actually spend most of their lives, and careers, doing something else. So by the time they’ve made manager, they’re beginners again. 3000 days into their career, they’re actually on day one. So, when they start, they’re probably not going to be very good. No different from the first day you pick up a guitar.”

What Johnathan Will Probably End Up Reading

While we’re on the subject of Jason Fried: he and his co-author/co-founder DHH have a new book out and I suspect it will have good parts. I could do without the mental health shaming in their title, but we might not have the moral high ground on book naming. Speaking of which, it launched one year after our own book almost to the day, so clearly brilliant management writing is a Libra.

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