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Asking for a Friend: How Do You Learn to Manage People?

In the second installment of our advice roundup with the co-founders of Of a Kind: doing the job no one teaches you.

By Erica Cerulo and Claire Mazur

Illustration by Tram Nguyen

ulo ran the design-minded e-commerce business Of a Kind, they learned a lot—and a lot of it the hard way. To spare you some of the head- and heartaches they experienced, they’re answering a couple Qs about creative entrepreneurship to help you on your way. Here’s the second installment

Q. How do I become a good manager? There’s no one showing me the way, and I don’t want to screw it up. Getting good guidance feels especially fraught these days.

Congrats on wanting to get this right! That’s a heck of a start. It seems so many people just jump into a management role without dedicating much headspace to how they want things to function, and unfortunately our thoroughly modern work culture doesn’t do much to set anyone up for success on this front (Management training?! LOL.).
When we hired our first employees, we made a slew of mistakes. You will too—but hopefully what follows will keep you from making some of the same ones we did. You will also get better at it with practice, so cut yourself some slack when you flounder. While you’re at it, try to do the same for the person you’re managing, too.

Set Some Boundaries

There’s a difference between being friends with someone who reports to you and being friendly with someone who reports to you. If you want this to be smooth sailing, you’re aiming for the latter. Where’s the line exactly? For us, it’s the difference between knowing the name of an employee’s significant other and knowing every detail of their WFH routine. Camaraderie is important—talk about an illustrator you discovered, a book you’ve been meaning to read, a recipe you’ve been cooking all you want!—but developing a too-familiar bond can, among other challenges, make it hard (on both of you) when you need to have a tough conversation. Suddenly, your employee can feel like you turned on them when you’re just doing your job, and the conversation can have a more personal undercurrent than it needs to.
But this doesn’t mean that everything personal ought to stay private. Say there’s a big thing happening in your life that affects your day-to-day, like a sick parent or a pregnancy. Share it in a way that feels authentic to you and appropriate to the setting—and encourage anyone on your team to do the same. Definitely tell people who work for you that you want to hear these things from them—but also lead by example. That’s what sets the tone to make someone comfortable sharing, and you’ll save your reports a lot of stress if they know that you seeming distracted in a meeting has absolutely nothing to do with the project they’re presenting. Navigating these conversations can be harder when they’re mediated by a screen, but that also presents an opportunity to lean into the literal visibility you have into people’s home lives to get (just the right amount of) personal.

Prioritize—and Systematize—Face-to-Face Communication

How lucky are we to have Slack, email, and all of the collaborative tools we do?! Hugely. But as wonderful as they are, they’re not the best forum for everything you have to say. We hate a waste-of-time meeting as much as the next person, but a weekly check-in with someone who reports to you is never a waste; even if you don’t think you have so much to catch up on, it’s worth doing.
Our take: Create a shared agenda that you both have access to and can update. Ask your employee to drop in all of the projects they’re working on—whether they’re short-term or long-term. For starters, this gives you a full sense of what’s on their plate. Beyond that, it prevents things from slipping through the cracks. You’re much less likely to forget that you need the first round of design materials for the winter symposium in October if “Winter Symposium” has been on the agenda since August. Then, as you both go about your days, you can drop any item into the doc that needs addressing at your next sit-down. We’ve found this wards off poorly timed interruptions from someone wanting your input on something right now—because there’s already time set aside for all that.
When you get in the same room—or the same Zoom—make your way through that agenda, glossing over anything that doesn’t need to be dealt with immediately (but not deleting those things!!) and, even more importantly, use the face time to get a sense of how your report feels about what’s on their plate, what their priorities are, how the broader team is working together. As in: Actually ask those questions, and phrase them in ways that don’t allow for a “yes” or “no” answer. You’ll get very different responses by posing the Q “Are you stressed?” versus “What project are you most stressed about right now?” This will give you a head start on dealing with potential issues. It will tip you off to minor grievances or scenarios that could go sideways—the smoke before the fire, if you will—and you can figure out how to solve them before they blow up.

Give Feedback Fast

When the person who works for you knocks your socks off, tell them. That’s confidence-boosting and just plain nice—and it also helps soften the blow when you (inevitably) have to tell them they screwed something up. When that happens—and it will happen!—address it stat. Ask if you can chat for 10 minutes. Say something like, “Hey, I’m disappointed in how this went down. Why did that happen, and how can we prevent it from happening again?” And actually say these things: Don’t type them. Tone is key.
Don’t let the issue fester for a week and then try to deal with it. By giving it days to stew, you make it into something bigger than it needs to be (and likely leave your employee thinking, “Wait, you’ve been upset about that this whole time?”). Plus, being direct eliminates detective work. You don’t want someone spending their working hours searching for signs you’re mad, reading into any curt chat messages, and wondering when another talking-to might be around the bend.
If the “Uh, we need to talk” conversations are happening on a regular basis, well, that’s a separate topic.

Practice Managing Up

One of the very best ways to get good at management is having a boss—good or bad!—and learning to manage them. It might teach you how to best structure an efficient team meeting…or it might show you just how terrible many people are at setting expectations or giving clear direction.
Sure, it can be frustrating to work for someone who’s not telling you what they want from you, but you can, in fact, ask. “How do you like to receive information?” and “When’s the best time of day for me to run things by you?” and “How do you see me being involved with this client?” are all A+ questions, and getting adept at posing them will remind you what you really should be conveying to someone who works for you. Because it turns out being a good boss and a good employee aren’t so different after all.

August 11, 2020

Erica Cerulo and Claire Mazur founded the e-commerce site Of a Kind in 2010, sold the company to Bed Bath & Beyond in 2015, and grew their business until 2019. They’re the authors of the book Work Wife: The Power of Female Friendship to Drive Successful Businesses and have grown a diehard following for their newsletter and companion podcast, A Thing or Two and members-only hub Secret Menu. You can find them on Instagram @ericacerulo and @clairemazur.