Managing your manager

Emma: This week, we’re going to talk about having a bad boss.

Andy: Yes we are. As much as The Bent is written with managers in mind, pretty much everyone reading it is also being managed — often by someone who drives them crazy.

Emma: Or disappoints them, or takes them for granted, or is trying hard but doesn’t seem to quite know what they’re doing. This one’s for you!

Andy: I used to think the boss I got was the boss I got, kind of like getting assigned to an Intro to World Civ class: “Oh, you got DeSpain? Luckkkyy. I got Roberts, wamp wamp.” I hadn’t learned yet that I teach my boss how to treat me.

Emma: And that I get to ask them for what I want, not simply accept what they are offering and nothing more.

Knowing what you want and asking for what you need is Communication 101. I don’t think we’re blowing anyone’s mind here. But it blows my mind when I think back on how many disappointing 1-on-1s I’ve had because I relied on a bad manager to guide the conversation. Or how often I’ve been frustrated because my boss wasn’t as invested in me and my work as I wanted them to be.

It drives me nuts. “I shouldn’t have to manage you!” I want to shout. “IT’S YOUR JOB to manage ME!” But waiting around for a boss to tell me what they think I should want or what they think I should be doing, or to one day magically give me what I’ve been quietly craving all along, isn’t a strategy I recommend. I have more agency than that.

Agency isn’t going to help me much if I have a truly terrible boss.

Andy: That’s what HR is for.

Emma: But once I figured out that managing is a two-way relationship — that I can respond to it — I had way more control over what was happening to me.

Andy: Yes! I had a manager once who’d email me at 11pm, at 1am, at 4am. I hated it. Waking up to a bunch of emails and responding to them before I’d done my morning routine filled my whole day with anxiety. “Doesn’t he know that humans need to sleep at night?” I’d complain to anyone listening.

Managing my manager meant saying no to the feeling that I had to live with it just because “he’s the boss.” It also meant giving up complaining.

Emma: Ha! You get to either bitch and quit, or quit bitching and stay.

Andy: Lol it’s so true!

To get there, I had to remind myself again and again that I’m responsible for making the office the best place for me to work. That meant clarifying expectations and asking my manager for what I needed: Permission to not look at those emails until I was in the office.

Emma: How’d it go??

Andy: He said, “My god, Andy. I have insomnia, but I hope you’re sleeping and please please please do not read them until you are in the office.”

Emma: Victory!

Andy: Some of the big problems I’ve had communicating with my bosses come from one wrong idea: That it’s my job to impress my boss, not request things of them.

Emma: Totally. But you can still project “I got this!” while admitting where you’re weak or confused or kind of a disaster.

Andy: And it’s impressive to ask for what you need and to admit what you don’t know. That takes self-awareness! Strong communication! Risk-taking!

Emma: Risk-taking for sure, especially when your boss is scary or intimidating or particularly unhelpful. But I’ve found that asking those bosses for help tends to make them less scary, less intimidating, and more helpful. And if they just dismiss me, again and again, that’s good information to know, too.

Andy: All managers start out less than ideal. Your off-the-rack boss isn’t going to fit perfectly. You’ve got to tailor them.

When I first became a manager, I was so grateful for reports who helped me manage them better. I still am! Thank you for asking me how to get what you need, and for getting yourself what you need. Thank you for not just suffering through something I can change until one day you leave for a better place.

Emma: Or stay, miserable and bitching.

Andy: Yikes.

Asking Your Boss For What You Need

Part 1: Knowing What You Want

You might already know exactly what you wish was different — maybe you also dislike responding to emails before you have a cup of coffee. Often, though, the frustration that comes from being poorly managed blends together into a sort of general dissatisfaction. If you have trouble articulating what you actually want, start by answering these five questions.

What do you complain about when you get home?
What don’t you know how to do?
Where are you stuck on your projects?
What do you dread doing?
What do you wish for?

Part 2: Asking For It

If you’ve never asked for anything from your boss before, we recommend starting small and simple, like specific help on a project or better instructions on a confusing request. Remember, you’re learning how to ask for something. Go easy on yourself. (Your boss is probably also going to be learning how to give you that thing. Go easy on them, too.)

Add your ask to the agenda of your next 1-on-1. Lead with warmth, empathy, and humor — this isn’t a dump where you complain about everything your boss has ever done wrong. Keep it simple by directly and specifically asking for what you need. Bonus points for providing context. Here are some examples from our own lives:

• Learning something new: Can we save 5 minutes at the end of this 1-on-1 for you to show me how to pull the weekly report?

• Figuring out next steps: I’m feeling stuck on this project. I have three ideas for where to go and would love your take on which direction you think is best.

• Asking for permission: When you send a late-night email, does it work for me to answer it by noon the next day? That way I can come in, get my team started on the day, and then send a focused reply.

• Changing your boss’s habits: I’m loving pulling the reports for the monthly recap. One of my goals is to be able to spot and tell the story in the numbers. Can I take a crack at drafting next month’s recap with you?

• Requesting specific feedback: I’m working on being a sharper, more articulate writer. Can you review this piece and provide feedback on where the voice and organization is strongest and weakest?