My approach to managing up

or, “does Jean have her shit together?”

Jean Hsu
Jean Hsu

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When you work with someone, either as their peer, or as a lead, you generally have an opinion or feeling of how they make you feel. Seeing someone might give you a sense of dread because you don’t know what they’re doing but you also don’t want to nag by interrupting them to ask for a status update. Seeing another person may give you a sense of well-being and confidence in your team and work. Or maybe you think “ugh not again” when someone starts to speak (harsh, but true).

When I think about managing up, I try to put myself in my manager’s (or the company’s, or the CEO’s) shoes. What is their communication style, and what is ideal for them? And then I try to figure out exactly what I need to do in communicating with them so that in their interactions with me, they think, “Wow, Jean really has her shit together.”

A few years ago, when I was working on a project and felt like I needed to get sign-off for something, I thought about who I was emailing. I knew that he wanted people to take more initiative, but he also wanted to know what was going on. He was also very busy, but I knew that he read all his email. So I sent an email with a few short sentences to provide context, included a few bullet points of my plan, and ended the email with, “I’m going to proceed with this plan tomorrow unless I hear any objections or concerns I haven’t thought of.” In this case, I never got a response, but sometimes I would just get a “sounds good, thanks.” I heard later that he really loved this mode of communication as it kept him in the loop but he didn’t have to take any action (or respond to a series of in-depth questions), and it deepened his trust that the communicator had thought through issues and would make good decisions. I later read about this technique in Turn the Ship Around, which I highly recommend.

Another time, I was working on an infrastructure project. After a few weeks, I checked in with my manager for feedback on how I was doing. He looked a bit embarrassed and said that honestly he wasn’t paying much attention to it, but he figured it was going fine. Rather than feeling like I was working on something that had been overlooked or unimportant, this felt like a success. I was working on something I already knew was important for the company, and I had built up enough trust with my manager that if I didn’t raise any issues directly or in the weekly updates sent out to the team, he trusted that things were going well.

I’ve met a lot of people who prefer to be…let’s say, comprehensive, in their communications. Over-communicating can seem like a safe bet, like a firehose of information — if the recipient doesn’t digest it all, you can place the blame on them. But communicating at the right level of detail and granularity for your audience is critical. If someone non-technical asks you how long something will take, and your answer is 5 minutes long and includes function names, that person will probably avoid talking to you in the future.

If you’ve ever read a 10 paragraph long email, sat through an 80-slide presentation, or been in meetings with a chronic rambler, you know that information overload is not effective. You tune out, feel badly because you’re not paying attention, and groan inwardly when those individuals speak in meetings or at all-hands. I learned to trust those instincts. Now I try to explore why that person made me feel that way — and then figure out how I can improve my communication and managing up so that I don’t do that to others.

What makes someone think “Jean has her shit together” really depends on the person — how busy they are, how involved they want to be in what I’m working on, if they want to be consulted or just informed, their personal communication preferences. There’s no one-size-fits-all, like sending a daily update, or only asking for forgiveness not permission. Asking myself that question helps me figure what will be effective for the specific person or audience.

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VP of Engineering at Range. Previously co-founder of Co Leadership, and engineering at @Medium, Pulse, and Google.