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

During the nine years Claire Mazur and Erica Cerulo 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 of a two-part series. You can follow their weekly newsletter and podcast for more intel—business, design, and otherwise.

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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.

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Asking for a Friend: What Does It Take to Build a Successful Partnership?

During the nine years Claire Mazur and Erica Cerulo 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. This is the first installment of a two-part series. You can follow their weekly newsletter and podcast for more intel—business, design, and otherwise.

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Q. I’m thinking about starting a business with a friend because now, weirdly, is feeling like the right time to go for it. We’ve known each other a long time, but we’ve never worked together. Before we dive into this uncharted territory, what should we know about building a successful partnership?

First things first: We’re so excited for you! About a decade ago (during a recession, it’s worth noting), we were contemplating making this move ourselves, and taking the plunge was one of the best professional and personal decisions we’ve ever made. We feel so strongly about the partnership we’ve built and the life-changing magic of solid business partnerships in general that we wrote a whole book on the topic called Work Wife: The Power of Female Friendship to Drive Successful Businesses. That said, we also very much understand that teaming up with a pal doesn’t always work out the way it has for us. There are plenty of friendship-to-business breakups to look to—Steve Jobs and Steve Wozniak, Paul Simon and Art Garfunkel, and Lena Dunham and Jenni Konner come to mind—and probably at least as many people in your life advising you to never go into business with a friend because you’re putting the relationship on the line.

The fact of the matter is that we can’t imagine starting a company with someone who doesn’t know us in the way we know each other. How different would it be if we couldn’t glimpse across the table in a meeting and say a thousand words with just one look or if we didn’t have the context to help one another navigate the family drama that inevitably weasels its way into the work day? But making the transition from friend to partner takes a ton of trust and plenty of work. Below, our checklist for getting it right.

Kick the Tires on Your Relationship Before You Make Anything Official

You might not have worked together in an official capacity, but have you planned another pal’s birthday together or coordinated a big group trip? If so, were your communication styles similar? Did this potential future business partner do things during that process that made your eyes bulge or your head spin? Because you better believe the same is bound to happen in a high-stress work setting. Be honest with yourself about the clues your friend has given you about the ways they operate in the world—and the ways those things affect you. If your would-be partner dominated the conversation during a Zoom baby shower and you wanted to shout “MUTE!,” trust that the same is likely to happen during business calls. Also remember that if you find yourselves professionally incompatible, it says absolutely nothing about the value of your friendship.

Make Sure You Both Feel a Sense of Ownership

If you do decide to move forward with this pursuit (hey, congrats!), discuss who’s in charge of what early and often. Having clarity on this will keep you from stepping on each other’s toes and also ensures that you both feel like you have authority. As wonderful as collaboration is, you need to be able to divide and conquer—and you need a structured way to make decisions when you have differing opinions.

Our approach: Make an oh-so-simple spreadsheet with your names in two columns and everything that needs to be done to run your business in the rows. Divvy up the responsibilities, and, in doing so, determine that the person with the X by their name is the one who gets final say. This doesn’t mean that the other can’t and shouldn’t weigh in about, say, pricing strategy or social media—just that you’re not going to make every single call by committee and that you trust one another to make good decisions about something, even if it’s not the one you might have made.

Welcome the Power of “We”

A key to establishing a strong partnership is putting egos aside. This is hard! You will fail at it time and time again! One of the best ways we’ve found to remind ourselves—and everyone we’ve worked with, internally and externally—is to lean hard on the word “we,” as in “We’ll get back to you” or “We really appreciate your support.” It’s an itty-bitty, two-letter trick that hammers home that we’re doing this together, and that even if one of us didn’t sign the contract or deliver a piece of hard news, we are both on board. Over the years, we’ve been surprised by the number of people who try to play us off one another or figure out who’s really in charge (talk about infuriating), and this language guards against that, too.

Be Vulnerable

Listen, all of these tips are important, but we might have saved the best for last: You have to be willing to share your feelings, fears, and hang-ups with one another. Expressing that you feel insecure about your role in a project or that your personal finances are in a precarious, anxiety-inducing state is not a to-do list item any of us wants to tackle. But if your partner doesn’t know the things that are keeping you up at night—or the side projects you need to bite off to keep the bills paid—you can’t support each other and make sure this bond is serving both of you. 

One tactic that works for us is to end weekly check-ins (you’re having these, right?) by asking, “How are you feeling about everything?” This is a question that creates an opening for someone to voice any concerns or discontent—related to the partnership or otherwise. It can often feel hard or awkward to know when it’s the right time to bring up something tense. But creating this routine means there’s always an opportunity to do so, and if nothing tough needs to be addressed, great. It’s an opening to hear how the other person is doing, which is just as important.

We understand the instinct to put on a brave face and to want to prove how competent you are, but acting like everything is just peachy when it’s not serves no one. Over time, that will create distance between the two of you and take its toll. And we all (the two of us perhaps more than anyone!) want your partnership to last for the long haul.

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