Why your least favorite manager got promoted
Author's note: I hesitated writing this one because it talks about stuff that isn’t necessarily “right” or “good” but is — I believe — the way things work. In some contexts, the stuff I talk about leads to gross, toxic, inequitable environments. But being good at this isn’t inherently wrong, and gives you more tools to get what you want at work. I believe you can use those tools to build amazing things.
If you’ve been in the workforce for at least 5 years, you’ve worked with people and thought “how did you get this job,” or — if it was rull bad — “...really?”
Maybe you’ve been able to avoid being managed by them directly, but at some point everyone is going to look around and think “I don’t get it” about someone they work with.
Your least favorite manager was probably your least favorite for one of two reasons:
They’re genuinely very good at what they do, but working for them is terrible because they’re not good at managing, they’ve started to manage things they’re not good at, and/or they’re mean
They’re clueless and well-meaning, or clueless and opinionated, or just straight up clueless
There’s no great mystery behind the first manager’s career — they were good at something, so they got promoted — but what about the clueless one?
Career growth is based on performance, except when it has nothing to do with performance
“The lesson from cases of people both keeping and losing their jobs is that as long as you keep your boss or bosses happy, performance really does not matter that much and, by contrast, if you upset them, performance won’t save you.” – Jeffrey Pfeffer, Power
I think career growth comes down to 4 things:
The company you choose
Performance / subject matter expertise
Your ability to operate within an org
Whether or not people like working with you
This is a sketchy model (in the sense that it’s a sketch, not in the sense that you’d cross to the other side of the street at night), and there’s a lot it doesn’t capture. In my head, I can hear my stats/psych professors talk about mediators and moderators, and it’s pretty clear that 4 has an effect on 3 (and 3 affects performance).
All true. Life circumstances are different for different people — also true. There are many types of career success. More truth!
Still, for the person trying to jump from IC to manager or manager to director — or just wondering how the hell {boss} managed to rise to the level of {boss’ level}, these 4 are pretty good.
I’ve written about the company you choose, and why its product/market/growth are going to impact your ability to get promoted. Most of what I write here is about how to operate within an organization — the skills of a manager, how to ask for things from other teams, the right amount of process, and generally how to get things done — which I think is a gate on growth for lots of people.
This newsletter is pretty explicitly not about how to get better at your work (it’s about soft skills, not hard ones), but I put a lot of effort into hard skills and believe in getting better skills and better performance. This guy writes some good stuff on that topic.
So what about this fourth factor? How does being great to work with — in a particular way that bosses like — help people get and keep high-level jobs, sometimes independent of their performance?
The “huh” managers are usually good at managing their boss (for better or for worse)
“Be polite, on time, and work really fucking hard until you are talented enough to be blunt, a little late, and take vacations and even then . . . be polite.” – Ashton Kutcher
The title of this piece is about your least favorite manager because, unfortunately, direct reports are the people most likely to be negatively affected by a clueless manager.
A manager’s influence in an organization is related to the output of their team — but only insofar as the output of their team serves to benefit their boss and their peers. Ideally, that output is also in the service of the organization, the customer, and the direct reports. It is not always, and even high-performing orgs are going to have outputs that serve internal stakeholders more than external stakeholders. This is why MBA-style textbooks talk a lot about silos and “alignment.”
If you’re at a high level in an organization, you serve there at the pleasure of your boss and your boss’ boss (if applicable). Your relationship with your peers is next most important after that, because it affects your ability to do the things your boss wants.
Is the goal to “do the things your boss wants?” Yes and no. It’s not, in general, my goal (although in fairness, my bosses and I tend to want the same things at the moment). But if the big boss wants things, there’s a limit to how many times you can avoid giving them those things and stay in a high-ranking position.
Compare these two situations:
The big boss comes to you with stuff they want on a regular basis. You think the stuff they want is misguided at best, so you push back on every ask. Every conversation with the boss turns into a battle — picture the deep breath they take before they step into the room with you — and eventually they come to you less and less.
The big boss comes to you with stuff they want on a regular basis. You think the stuff they want is misguided at best, but you go ahead and do it to make the boss happy. The performance of the org suffers because the org is working on the wrong things. But results don’t tank immediately (they decline over time), performance of an org has lots of factors, and you and the boss have good long conversations where you hang out and make each other laugh.
These are both bad situations. But in which situation are you going to get fired faster?
People who are able to reach and keep jobs at the level of director or above are good at finding the balance of things that need to be done and things that the boss wants done — or at least they index on things the boss wants done enough so that the boss keeps them around.
A poor leader in a faltering org might get fired, but it’s going to take longer than you would expect it to based on performance alone (if they’re chummy with the boss).
If used appropriately and alongside strong performance, I think managing the boss is a great skill that can ultimately get better results for everyone involved.
So how do these people do it?
They do it by following advice from a book about parenting (not even clickbait)
3 ways:
Smile and take an interest in other people
“Yes and” – avoid “no, but, however, that said, yet.”
Show you care about what the boss cares about
1. Smile and take an interest in other people. Everything in my career got better when I started smiling more and trying to make things more fun. “Smile more,” as a statement, is loaded af and missing all sorts of context. It’s not the big idea. The big idea is that you want to be a person people want to be around.
When someone has a meeting with you on their calendar, do they think “dammit, gotta get through this,” “hm” (neutral), or “oh this should be a good time?”
If people look forward to talking to you — if your boss looks forward to it — they’re going to want to work with you more. You’ll find it easier to operate in the org. Shit, you’ll make friends and work will be more fun.
There’s some risk in being too playful or goofy if it comes in the absence of performance, in which case I’d say reign it in a bit and increase performance. I reign in my silliness in work conversations in the same way I’ve learned to reign in my intensity — overall, I want to have fun at work, I want other people to have fun at work, and it has the benefit of helping to get things done.
But it’s not about a particular style of being well liked. Some people you like working with because they’re genuine and heartfelt. Some people are playful. Some people are motivated and ambitious.
Some people are so clear in their respect for other people.
You have your own qualities you can bring to work.
2. “Yes and” – avoid “no, but, however, that said, yet.” I see so much more advice about “pushing back” than I do about yes anding. Why do we need to push back? Shouldn’t we all be on the same side and working towards the same goals?
You’re going to hear plenty of ideas that you think are silly. And people — maybe your boss — will ask for things from your team that you think are dumb or that you’re frustrated you have to make time for.
These are opportunities. You can learn to identify the ask behind the ask, and you can learn to channel the things people actually want (vs what they say they want) into efforts that you also want.
What you don’t want to do is hit them with a “no” or “that’s not a priority” or “I like that idea, buuuuuuuuuuuut.” It’s slamming the brakes on your relationship with them.
In his book What Got You Here Won’t Get You There, Marshall Goldsmith lists this as one of the twenty habits that prevents smart leaders from continuing to rise:
“When you start a sentence with “no,” “but,” “however,” or any variation thereof, no matter how friendly your tone or how many cute mollifying phrases you throw in to acknowledge the other person’s feelings, the message to the other person is'' You are wrong.” It’s not, “I have a different opinion.” It’s not, “Perhaps you are misinformed.” It’s not, “I disagree with you.” It’s bluntly and unequivocally, “What you’re saying is wrong, and what I’m saying is right.””
No, but, and however are what we’d call “blocks” in improv. Instead, you want to take the energy that led someone to suggest an idea and redirect it — either to a different idea that serves the same purpose (but better) or back onto their own idea to improve it.
This takes practice and a strong understanding of what other people want.
A simple trick to get the “buts” out of your vocab is to just replace them with “ands” and then rephrase your response until it makes sense.
3. Show you care about what the boss cares about. I think this is the big one. In any given org, the boss is more incentivized to care about things than the direct report, and so bosses are used to being the person that cares most.
When I was at my last company, I had a boss who showed me how they managed up. They pulled up this spreadsheet that showed every competitor in every market that was even slightly related to ours. For each competitor, it included:
Total funding
Headcount
Growth
Revenue numbers (as available)
Major product features
Major marketing campaigns
Followings across every social media platform
And loads of other stuff I can’t remember. Seriously, this thing was huge.
Did we need this information? Did any of this really change our decision-making processes at the time? Not really. It was interesting, but not a dealbreaker by any means.
What it did do is show just how much my boss cared about the things the big boss cared about. As they said to me “He [the big boss] thinks about this all the time. And even if he doesn’t say anything, it has to be frustrating that other people don’t care about it as much as he does.”
Imagine that you missed your targets this quarter by something small — let’s say 5% is small in the context of your org. The CEO asks you what’s up. Which of these responses is going to build more trust long term?
“We just don’t have the resources to hit this target. Sales keeps asking us for things and the devs said they would release this feature but didn’t, which threw us off. Either we need to not get all these other asks or we’re going to need more headcount.”
“I’m pissed we missed the target! I think we should be doing double that number. We’ve got to coordinate things to make sure we’re serving sales and devs in a way that lets us hit this target too — can I work with you on that?”
The first response is asking for something (resource, headcount) the CEO probably has to say no to, which no one likes doing. The second asks for their buy-in on solving the situation — which you know they’re interested in (because they’re asking) and can scope to be a small amount of work.
The first response is spreading blame. The second is showing how much you care.
Here’s an exchange from the book How to Talk So Kids Will Listen and Listen So Kids Will Talk. The context is a 5 year-old (Jennifer) who keeps coming into her parents’ bed at night and waking them up.
I am not saying that CEOs are like 5 year-olds. I am saying that everyone, at every age and every stage of life, wants to feel understood and respected.
Here’s another story from the same book (emphasis mine):
“A father told us about his nine-year-old daughter who had developed a passion for horses. One day she asked him if he would buy her a horse. He said it took some effort not to tell her that it was out of the question because of money, space, and town ordinances.
Instead, he said, “So you wish you could have a horse of your own. Tell me about it.”
Then he listened as she went into long detail about how she’d feed her horse and groom him and take him for rides every day. Just talking about her dream to him seemed to be enough for her. She never pressed him again actually to buy the horse. But after that conversation, she took books out of the library about horses, drew sketches of horses, and started saving part of her allowance to buy land one day for her horse.
A few years later she applied for a job helping out at a local stable, where she traded her services for occasional rides. By the time she was fourteen, her interest in horses had waned. One day she announced that she was buying a ten speed bike with her “horse money.””
This, overwhelmingly, is the thing “huh” managers are good at. Your CEO probably doesn’t want to buy a horse, and they may not be talked down from the things they do want so easily.
It’s by showing you understand what they want — showing you care about what they want — that gives you the latitude to make suggestions and nudge towards what you think is best. Or at least stick around in your high-level job for longer than you would otherwise.
I like to be at a company that values performance and with bosses who want things that make sense, and I am at the company like that. If you don’t feel like you are, you can consider leaving or you can stick it out.
No matter what you decide, you’ll be more likely to get what you want if you show how much you care.