open thread – May 19-20, 2023 — Ask a Manager

Ran out of nesting, so replying to Chipmunk here:

“Ok, I was thinking your boss has been knowingly struggling this whole past year, rather than for just a couple of days.”

I’ve been pointing out intermittently for a year that he should TELL people what the deadlines are, but he’s been thinking that another reasonable solution is to conclude that the project was too hard for them, to tell them “good job”, and to assign them to another project that they can be more successful on, in hopes of allowing them to play to their strengths. I kept telling him in a low-key way that that wasn’t a great solution, but his anxiety kept telling him it would be way easier than learning to communicate directly (scary!), so he kept convincing himself it was a great and totally viable approach to management.

Only last month, after a year of trying different projects and concluding that one particular report is good at some things but not others, but we really need someone who can do the things he was hired for, did my boss start thinking out loud at me about whether we should fire the report because he can’t do the most important things we need, or keep him because he does do a lot of really good work elsewhere, including in places where we didn’t expect.

I said that I didn’t think we could judge how good the report was at the biggest projects, since I was convinced that the report was doing exactly what he thought he was supposed and allowed to do. I said if he wasn’t making certain decisions and acting on them, it’s because he thought he had to wait for Boss to make the final decisions. I got Boss to promise to put any discussion of firing on hold until I came back from vacation.

I came back this week, and on Wednesday I talked to the report. I told him he was authorized to make these decisions, because Boss isn’t an IC any more and doesn’t have time. (The other problem with promoting the best IC without training is that they keep doing hands-on IC work, which blurs the boundaries.)

Report went, “Oh, I’m supposed to actually build these products? I thought my job was just R&D! I was wondering why no one was ever building the things I researched. I would love to build them!”

Me: “Well, that explains why Boss keeps saying that you’re finding lots of good information but the projects aren’t moving forward.”

That same day, I told Boss about this. He was flabbergasted, I was not. Yesterday, the three of us met, agreed to start with a mutual clean slate, and and we proceeded to establish clearly defined expectations (i.e. did project management). Report knows he was expected to do things he wasn’t told about despite positive feedback, but he doesn’t know he was almost fired, and he knows that I’ll be working closely with him and Boss to train them both to communicate better.

Right after that, I grabbed Boss, and said, “So, are we clear on the fact that if this high-visibility project didn’t get done FOR A YEAR because of lack of communication, and our report almost got fired, your acknowledged communication issues are no longer a nice-to-have for you to improve someday, but something that urgently needs to improve asap?”

And he said yes, and agreed with everything I said, and asked for training video recs. This was 24 hours ago, so, yes, I’m willing to help.

I also may have used too impersonal language when I said “people were fired/almost fired/not promoted”: he’s the one making the decisions here, now with my input. So as long as I’ve got him convinced he’s the main problem, no one gets fired/almost fired any more without my say-so. So it’s not like people are in danger of getting fired until he gets better at this. I’m the safety net here.

“I don’t necessarily think that having the requirement of being a self starter is bad…but you’ve already seen how that can weed out staff from diverse backgrounds, such as the employee from a different culture.”

It’s always been pretty common to enter this field with little to no relevant education and very little training, just tinkering in your spare time, so I wouldn’t describe that as a “different culture.” I think part of the problem is that’s exactly what my boss (and I, and his boss, and probably everyone else in the history of the team) did, so the really successful people largely think no mentoring or training should be necessary, because they certainly didn’t need it!

Now, if someone really *did* enter from a legitimately different culture, yes, not understanding corporate norms, for example, could be a hindrance. So there is an argument to be made there.

“And what field are you in? I’m great at figuring stuff out on my own and would love to get paid to solve problems and teach myself.”

Systems and database administration, increasingly transitioning to devops engineering, in this brave new world of ~The Cloud~. The thing is that you can totally come into tech with a degree in history and one year of software school, and have all the technical skills you need to get hired. Because there is no school that will teach you what you actually need to know on the job, i.e. the specific error messages you encounter (you have to google them, read stackoverflow, and use your brain) or the legacy code of the specific company you work at, so formal education in computer science is usually expensive and pointless. And if you can teach yourself tech on the job, you can make oodles of money.

BUT. What they don’t teach you in software school is that there are a dozen different soft and “soft hard” skills you need to actually keep your job, such as:
– Excruciating, character-level attention to detail.
– Ability to tinker successfully with software. This is made up of several components that come naturally to some people and don’t to others.
– A sense of the sweet spot of when to ask for help and when to troubleshoot on your own.
– A sense of the sweet spot of how far “above and beyond” to go. If you only do what you’re explicitly asked to do, you will be fired within 3 years, but if you’re a perfectionist, you’ll only get one or two things done when you should be getting 10 done.
– Risk assessment skills, so that you don’t break too many things but also don’t get paralyzed and never accomplish anything.
– Estimating unknowns (it’s dark magic, basically).
– A dozen little communication habits, which you wouldn’t think neurodivergent nerds would be notable for, but there are some very specific things that we successful ones do naturally, and some people need coaching on.
– Etc.

They don’t teach you this in school. They teach you code syntax, and then they send you out into the wild feeling pretty good about your As, and then you realize it’s sink or swim with all the personality traits and unspoken expectations. (I’m not talking about deadline expectations like my boss, I’m talking about the soft skill expectations I described above.)

If you’re missing too many of those skills, you will get fired. If you’re missing just certain ones, you will not rise as high as your technical skills warrant.

What I’m doing is telling people on my team about those unspoken skills, and giving them the chance to see if they can pick skills up with effort if they don’t come naturally. Aka, I am mentoring (the only manager in the history of my team that has ever seen the point of doing so). This is in *addition* to the fact that my boss isn’t doing effective project management and isn’t even telling people about deadlines they need to know about to succeed, which I’m coaching *him* on. (In addition to telling the team members that aren’t already spontaneously doing it that they need to *ask*, and they need to *keep asking*.)

Part of the problem is that there are almost no hard deadlines in the field, and they fluctuate constantly. So it’s never “this must be done by X date.” It’s more, “work on this, and I will judge your performance by how long it takes you in proportion to how hard it turns out to be and how much other work you’re doing.” You never know how hard a technical problem is going to be when you set out to solve it, and your priorities shift from day to day, sometimes hour to hour. There’s always new external asks coming in, and you’re always finding more stuff that needs to be fixed/updated/documented.

So what I’ve been training Boss to communicate is, “I will be surprised if X isn’t done by Y date and I don’t know why.” Because everything’s flexible, but his performance evaluation is based on his level of surprise at how long someone is taking to do something. This is why I also have to train my reports that a key factor for success in this field, and not just with this boss, is communicating when something is taking longer than expected because it turned out to be surprisingly complicated, and when it’s because you were assigned a bunch of other work. Because if you don’t, your boss will think it’s down to your skills and/or motivation.

But if your boss doesn’t communicate that he’s hoping to see X by Y date, you might not get it done because you don’t know that’s what he’s hoping for, and you might choose to prioritize something else. We have a backlog of 200 things to do at any given time, and a lot of autonomy to decide what to work on.

So the communication gap is understandable in terms of how it arose; it’s just a massive, massive failure in effective management, given that we do work in an environment like this and have to be able to manage in it!

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