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All Managed Up

How to help your boss see around blind spots.

I used to hate people managing up to me. I’d feel like I was being shepherded, but over time I started noticing that a lot of the time it wasn’t people trying to control me as much as people trying to figure out how to communicate with me. Me! I’m a really good communicator! What’s the problem?

Turns out it was me (it always is). A lot of things that make me a good writer make me a weird, discursive, introspective manager. It’s not like I’m going to become a different person. But as I’ve written before, you have to admit, and accept, that you’re in charge, and help people meet you halfway. And part of that is acknowledging, and accepting, that other people are going to manage up to you.

We’ve had Kellan Elliott-McCrea on our podcast before. He’s a technology leader in New York City. He recently gave a talk on managing up. What I especially like about the talk is that he’s the manager: “Cards on the table,” he says, “I am the person you are managing up to.”

There’s a part in here about making your boss look good that I want to call out:

This is probably the most important skill of the whole section of making your boss look good and managing up, help them see around blind spots. Management breeds blind spots; it is the nature of the work that we don’t know what we don’t know. We are divided, we are scattered, we’re the boss, we make snap decisions all the time, we are often the least-informed people in the room, and we don’t know it. Our job requires us to go on making those decisions. This is one of the frames that I really like to use when I think about managing up. The best managers need to be managed up….The best managers are the ones that are inviting you to manage up to them. They’re the ones who know they have blind spots, who need help. One of the phrases that someone said to me at one point that I really liked, it has been echoing in my head now for 20 years, “It’s my job to be pushing. I need you to tell me if I’m pushing us off a cliff.”

A little over a year ago I took over the front-line growth in Postlight. My co-founder Rich is really good at shaping larger engagements, so I focus on bringing attention to our firm and driving in more opportunity. I don’t design or build software; I simply work with a management team to create an environment in which software can be designed and built. But I’m also responsible to our clients, and they can ping me at any time. They have the expectation that I’ll know roughly as much about how things are going as anyone working on their project.

That’s tricky. There are 10–20 projects running at different paces at any time in our firm. So that requires me to know a lot of things, such as what stack we’re using for a given piece of software, when things are expected to be completed, and any flare-ups or concerns that should be expected. I read Slack and run growth meetings where we review every live engagement twice a week. On top of that, I get a staffing report.

A lot of time I’m operating on instinct, a pit-of-the-stomach feeling about how the client feels. A big part of client service is a sort of proactive empathy. So sometimes people are pretty sure things are good and I start asking them about what’s up and where the risks are, which feels invasive. Sometimes The client is going through an upheaval mid-project and can’t tell us what they need or even return our phone calls. Sometimes the right thing to do is keep going and figure it out later and sometimes the right thing to do is just chill out and wait for the next steps to come into focus, because anything you do will be wasted work. And it’s a coin flip, really. Pure instinct. Meanwhile, we’re in a project-based environment, where leadership means delivering work on time. As a result, my instincts, liberally shared, are basically guaranteed to drive everyone who works with me bananacakes. But my instincts are also pretty good.

When I look at my last year, building out the Growth and Partnerships functionality inside of a mid-sized digital product studio—well first, I never in the world expected to do such a thing. But second, I can see pretty clearly that I’ve been teaching the people I work with to manage up to me, and that across the organization I’ve been trying to share the reasoning behind my instincts with people. I’m still confusing, I think, but hopefully less so. One day I hope I’m not confusing at all. The whole thing makes me squirm, but a big part of management is getting used to everything making you squirm.

Paul Ford is the CEO of Postlight. Send him an email: [email protected].

Story published on Sep 11, 2019.