Many of us dream of the day when we’ll become managers. Finally, a chance to be the boss, have your voice heard, and do shit the way you want to. Getting the promotion is a huge deal, and even if it’s extremely nerve-wracking, it’s also a major career milestone. But how do you actually learn to be a boss? When you step into that role, it’s unlikely you’ll have had any training, and chances are, you’re going to make some mistakes.
One way to learn how to be a good manager is to take advice from the smart women who’ve come before you. Ahead, we interview six women who told us about the mistakes they made as first-time managers, and offer advice on how you can avoid similar disasters. One thing to keep in mind as you read this, everyone messes up — even if you read this article and take every bit of advice we offer here. That’s okay. Because that’s really how you’ll learn how to be an excellent manager: by seeking advice, learning from your mistakes, and being willing to admit when you’re wrong or you need help. It might be scary, but you’ve got this.
The first thing to remember is that just because you’ve been promoted to a management role doesn’t mean you automatically know everything about being the boss.
“A lot of people don’t get training in management, you just kind of have to wing it,” says Emily McInerney, the director of marketing at Tapjoy, a mobile app monetisation company and the co-president of Women in Wireless. This can leave many women feeling like they’re just not cut out for management, McInerney says, when instead they may just need a little help.
“You could be a great salesperson and you’re promoted because you’re good, but that doesn’t mean you’ll be a good manager. There’s a lot of different skills you need to learn,” she says. In order to get what you need, you must speak up. “Actively ask for help, guidance, and advice. Ask your company if they’ll sponsor you to get a business coach or do some management or leadership training. This company put you in that role, they want you to be better at your job. Even if they won’t sponsor it, think about investing in that kind of training on your own. It will leapfrog you to the next level in your career,” McInerney says.
Illustrated by Abbie Winters.
Some of those qualities that got you promoted — being a perfectionist, excelling at your job, and a desire to help people — could land you in a classic first-time manager trap: micromanaging. And everyone knows there are few things worse than a micromanager for a boss.
“One of the hardest things I’ve had to learn is to step back and watch when an employee is potentially making the wrong move,” says Katie Jansen, CMO for the marketing platform AppLovin, who has 12 years of management experience. At first, Jansen, 35, says, she was more of a task giver. While this method worked to get things done, she quickly figured out that she wasn’t thinking about the big picture — how she was helping to shape the careers of her direct reports.
Then, as her team’s responsibilities grew, micromanaging became untenable. “There just wasn’t enough time to do that every day,” Jansen says. “If we were going to get everything done, I needed them to think on their own, and figure out their own strategies without me telling them exactly what to do.” Jansen found the best way to help her direct reports grow into leaders was to pull back. “It was a little scary. You’re thinking, ‘What if they mess up?’ or ‘They’re not going to do it the way I would do it,’ but if it’s low impact to the business, even if they do make a mistake, you have to let them do that in order for them to learn.”
It can seem like it’s easier to just control what everyone else is doing, but in fact, you’ll be a better manager if you don’t have such a tight grip on day-to-day tasks. It will not only make your team happier, it will free up your time for more important tasks.
Illustrated by Abbie Winters.
A whole team of people exactly like you might sound fabulous and unstoppable at first, but multiplying your strengths throughout your team also means multiplying your weaknesses.“I’m a multitasker and I move really fast,” says AppLovin’s Jansen. “And I think naturally, but you tend to want to hire people just like you.”
No one is good at everything, even if you’ve done a really good job of faking it so far. The great thing about being a manager is you can hire people to help fill in your skill gaps. Jansen wasn’t sure at first if the person she hired to be her director of communications was the right fit for her pace. “He’s a very, very mellow guy. When I first hired him, I just kept thinking, ‘Is he even listening to me? I need this quickly!’ But it’s his nature to take things at a certain pace and he always gets it done and gets it done on time, and I’ve actually really learned to appreciate him and the vibe he brings to the team. It’s quite calming. He mellows me out.”
Hiring employees who have strengths that are different than you will make a team stronger, Jansen says, and keeps you from feeling like you have to do it all.
Illustrated by Abbie Winters.
Sarah Gibson Tuttle faced a steep management learning curve when she first opened Olive & June, a group of Los Angeles nail salons. Owning her own business was Tuttle’s first foray into a leadership role after working an equity sales trader at JP Morgan and Morgan Stanley for 10 years. “About three days into Olive & June, I walked outside and just started hysterically crying because I just wanted everyone to be happy all the time and it was so hard,” says Tuttle. A major issue for Tuttle was that she was trying to communicate with her staff the way she communicated in her old industry.
She realised pretty quickly how different things were on Wall Street. “Everyone is very Type A, and insanely driven and they all talk to each other very directly and have very little emotion about it,” she says. But that method was not flying in her new gig. “Beauty is an industry of art and design. When people are creative, they feel more and things are more personal. It was a struggle because I didn’t know how to act with a ton of warmth at work at first, I wasn’t used to it. I finally realised I needed to learn how the professionals in this field interact and how to motivate them.” Tuttle went to her employees for feedback, and they taught her a lot about the beauty world.
Learning to warm up at work really paid off for Tuttle. “People sometimes worry that the only result that matters is the profit margins. Personally, I think that a happy team is more important because they’re the ones that will produce what you’re after.”
Illustrated by Abbie Winters.
At first Tuttle thought being a boss meant she was always right. Eventually some stress over a chair taught her a very important lesson. "The chairs I ordered for the salons are unique. They’re not typical comfy lounge chairs like most nail salons have. They’re not plush. They’re sling leather and I loved them. Then I started to hear that some people didn’t think they were comfortable, and I was like, ‘What are they talking about? They’re so comfortable, I love them!’
“But then I thought, ‘If this is what customers want, then change something.’ I ended up getting a ton of pillows and now I use the pillows with the chairs,” she says. But Tuttle regrets she didn’t start listening earlier. “I should have taken some of those manicurists out in the beginning and asked what they thought about everything, but I was scared they would tell me something bad and I just wanted them to stay.”
Sure, you’re the boss. Your opinion does matter. But you should also listen to what your employees have to say. Chances are, they are witness to things you never see. And if you build trust with them, they can offer invaluable feedback that will make you a better manager.
Illustrated by Abbie Winters.
Jaclyn Johnson was just 24 when she started her own marketing agency, No Subject, and was faced with bringing on staff. “When I hired people in my own company, I immediately tried to be friends with them. It seemed obvious that we would be: I liked them and we were going to hang out all the time.”
But even though being friends seemed natural at first, Johnson says she realised it could lead to trouble when you’re the boss. “There can't be a sense of ‘favourites’ or a ‘buddy-buddy’ mentality in the office,” she says. That can lead to anything but a friendly environment.
“Now that my company is bigger and has more of a corporate structure, it was a culture shock because I realised I really wanted to set up those boundaries. But then you also don’t want to create a culture of fear, so it’s a super tricky balance.” Now, Johnson sets up that boss and employee boundary from the beginning. “You can be friendly with your employees...but there needs to be a thorough divide and respect in place on both ends to make [the relationship] work.”
Illustrated by Abbie Winters.
Managers learn quickly that the one thing worse than receiving criticism is giving it. But it’s also an essential job of a good manager. “One of my first bosses would reprimand me over something as small as not having a period at the end of a sentence, he’d bring me into his office and tell me I’d screwed up,” Johnson says. “I didn’t get it at the time, but that feedback made me so meticulous. Now I’ve become him, you have to go over your employees work and provide feedback. Even if at the time they feel offended, it will be lucrative for them in the long run.”
This can be tough when you’re a young manager, says Johnson, but the key is confidence. "When I hire people older than me, it’s bizarre, but one thing I’ve learned is they’re not trying to compete with me. They want to work with me because they see my vision and want to be a part of it.”
Critical feedback shouldn’t be given via email, Gchat, or Slack. If you’re nervous before you go into an awkward conversation, jot down some notes so you don’t lose your train of thought. Have the meeting in a private space, take a deep breath, remain friendly but firm, and make sure you give your employee some advice on how they can improve, rather than just being entirely negative.
Illustrated by Abbie Winters.
When Tracy D’Inunzio, 37, started the online clothing resale shop Tradesy, it wasn’t just her first time in a management position, it was her first real job. “We’ve gone from me in my living room to 125 people in the last three-and-a-half years,” D’Inunzio says.
There was a lot to learn, and D’Inunzio admits she made mistakes along the way. Trusting the wrong people impacted her team's overall performance. After a series of bad hires, she reassessed how she chose her staff. “I just wish someone would have told me to hire slower and fire faster. Nobody wants to be in a position where they’re not succeeding, so ultimately it’s the right thing to do for the person, the team, and the company. Eventually I got bolder about firing faster and better at hiring, and that makes being a manager much easier, you can get out of their way while they make magic,” D’Inunzio says.
Illustrated by Abbie Winters.
Some truths about being a manager exist no matter your industry. One big one: Once you become the boss, you’ll need to start paying more attention to your image. Mandana Dayani should know, she started her career in law, worked for years as the vice president of Rachel Zoe, Inc. and then last year switched over into the tech startup world joining Everything But the House, an online estate sale market, as their chief brand officer.
“Early on you need be thoughtful about the perception you create, in the office, and on social media,” says Dayani. “You need to be mindful of the pictures you put online, how you dress, how you speak to people, because everything plays into the way you’re perceived. And when you’re working in management, that means how the company is perceived as well.”
That doesn’t mean you need to wear a suit every day, she says. And it doesn’t mean you have to quit social media, just be more mindful of what you’re putting out into the world. Now that you’re a manager, you’re naturally a role model and it’s important to put your best self forward in every situation.
Illustrated by Abbie Winters.
“When I was pregnant with my daughter [and working at Rachel Zoe], my nesting hormones were getting the best of me,” says Dayani. “I wanted everything in a perfect place before I left for maternity leave so I was pushing really hard. I was putting a lot of unfair pressure on our team, I was expecting too much of them. At some point, my husband just looked at me and said the very important words: ‘It’s going to be okay.’ That really helped me let go.”
Now that she has her daughter, Dayani says, that lesson about exemplifying balance has sunk in even more. “Maintaining your own balance and having your own boundaries will help you be better as a manager,” she says. “If you work too much, your team thinks they have to too, and space from work is helpful for everyone.”
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