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I Interviewed the Best Boss I Ever Had, and Here's What She Told Me

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Jennifer Romolini is a badass boss lady. As Chief Content Officer of Shonda Rhimes’ new site Shondaland.com, and a former Editor-in-Chief at HelloGiggles and Yahoo, she makes running the Internet look easy, even when it’s not. 

In her hilarious and heartfelt new workplace memoir out June 6th—Weird in a World That’s Not: A Career Guide For Misfits, F*ckups, and FailuresJenn recounts her road to success, paved with menial jobs, insecurities and a revolving door of bosses.

So for #MentorshipMonth, Levo asked Jenn about the best boss she ever had. That's when she told us all about her former boss-turned-mentor, Facebook executive Jessica Jensen. Then, she interviewed her. Trust us, you need to read this.

My former boss Jessica is unlike any woman I’d met at corporate jobs or any other job. She’s smart, fast, unrelenting, disarming. She’s enviably accomplished, has held most of the impressive-sounding job titles at the most impressive tech companies and earned more-than-she-needs impressive-sounding degrees. She speaks several languages, has lived and worked all over the world. She is folksy and charming, a liberal-minded Kansas girl who spouts Dan Rather-like aphorisms like she came up as a ranch hand but still knows how to artfully throw the “fucks” around. She also scuba dives, does amateur improv and knows everything about bourbon. I’d hate her if I didn’t love her so much. As my boss, I watched her dominate rooms, eviscerate men trying to give us a bad deal in big partnership negotiations and then, before walking out, crack a perfectly-timed joke and leave the meeting giving everyone a high five. Her confidence was contagious, she made me like business, made it seem fun, helped me stop feeling like an awkward freak and more like the smart, savvy business woman she saw in me. She was every single thing I needed at the time and I have tried to emulate her best qualities ever since. She was, and remains to this day, everything a mentor should be.

Jessica came into my life as a boss during a time when was deflated, angry and had lost my way. She became a professional partner and a guide. She did the hard work of managing and never backed down from it, zeroing in on my strengths and helping me address my weaknesses. When I first met her, I was all ambition and fight, rough around the edges. She taught me not to soften my edges, but to sand them, to keep them sharp enough to assert myself, but not so sharp that they would hurt me or anyone else. She helped me focus and nail down a new path for my career, one that was far more business-y than I ever imagined. She did this through weekly feedback sessions that I did not like and by critiquing my work honestly in ways that were often painful to hear. I gave back to her by working hard and being the best version of myself, not only when I was under her charge, but long after I’d moved on.

When we mentor well and intimately, our reach goes far beyond a particular job and particular circumstances. We form long-lasting professional tribes. We build each other up. We stand on each other’s shoulders. We never want to let each other down. As women, supporting other women is among the most powerful and long-lasting impacts we can have —expanding far beyond the more myopic goals of a particular job. Jessica made a profound difference in my life. She didn’t save me, but she gave me a path to save myself, again and again. We haven’t worked together for years, but her influence stays with me, I hear her voice in my head as I make almost every important professional decision. I heard her voice as I was writing my book, too, especially as I was trying to sort out the mechanics of managing, of being a great boss. So I decided to give her a call. This is what we talked about.

Jennifer Romolini: Hi. As I’ve told you many times, you are the best boss I’ve ever had. You are a natural manager—you’re compassionate but tough, you don’t tolerate bullshit, you have amazing boundaries, you are always fair. I wanted to work harder for you than I’d ever worked before. Part of that was because I knew you were always in it too, working as hard as I was, part of it was because I never wanted to let you down. And it wasn’t just me: Everyone who worked for you felt that way, like you gave a shit, like you inspired them and brought out their best work selves. Since we worked together, I have tried to model your managing style, which always felt fresh and exciting and unconventional and I want to hear from you what you think that management style is—because I think it could be really instructive for people and also because I wish everyone had you as a boss. So here goes. Did you always want to be a boss?

Jessica Jensen: I don't think so. I wanted to be a leader — but I didn't know what a boss really was until my 20s. As a kid, I wanted to be a diplomat. I loved foreign travel and languages and politics. I was a massive dork. In high school, I decided I wanted to be a Japanese art historian. Then I worked in a museum and I was like, damn, this is lonely and I actually really like talking to people, not handling ancient scrolls. So then I pursued business and finally learned that having a good boss was, like, the most important thing to anyone in any business setting. The content of the work and the co-workers were really important, but it was really your boss that made you like or hate your job. So I wanted to figure out how to do that well.

JR: Who did you learn from? How did you learn how to manage people? (And if you tell me corporate management training I will believe you, but will also want to cry and stab things because that shit is so inorganic-feeling and weird.)

JJ: So my first "real job" was in management consulting in LA in the '90s. The company took management and development super seriously. We got feedback up down and sideways every two weeks. Every manager met with every direct report at least monthly to share "three good things to build on and three development areas." It was super honest and people were caring and invested in their team's success. It was an awesome learning ground and I think the time I spent there taught me 70 percent of what I use today. Then I also had a fantastic boss who invested in me, allowing me to stretch and grow and do really hard, scary things. She had endless confidence in me. She told me when I did well and when I messed up — but she did that with love and humor. I have tried to model myself on her ever since.

JR: Early on, what were some of your biggest managing mistakes?

JJ: I was a total helicopter-mom-manager. "You're stuck? I'll fix it!" "You are having a conflict with someone — I'll meet with them for you!" "That strategy document isn't good enough? I'll write it for you!" I didn't let people learn and grow. One of the best pieces of management advice I ever got was "Give back the pen." When a person is stuck or struggling, ask them "What do you think you should do? Go try it and I'll give you some ideas and then you see how it goes." I always try now to give people the pen. But sometimes I want to grab it and I have to slap my own hand.

I was also a big "net exporter of stress." I didn't draw a boundary between my own worries/anxieties and the emotional health of my team. I do this more now but it's still a struggle. I am an emotive person and I need to be very careful to not share every emotion or worry I have. I try to be a net importer.

JR: What do you like about managing people?

JJ: This is not BS—it is meeting and getting to know amazing people like you and seeing you find your own magical leadership groove and rocking the house. Helping people discover how they can be fantastic workers or leaders and go on to climb new hills. It is just the most heart-warming, inspiring thing I do. (Outside of being with my family and drinking bourbon.)

Okay and I also really like growing companies and making them win — and the only way that happens is through fantastic people who are loving their jobs and rowing the boat together, hard, through calm and choppy waters.

JR: Besides the fact that it is hard and sucks, what do you hate about managing?

JJ: I hate people who don't take responsibility for their own happiness or effectiveness. People who throw their hands up and are like "This place sucks!" YOU are part of the solution — or you are part of the problem. I hate lazy, defeatist people. I also can't stand passive-aggressive behavior. If you have a beef with someone or something, put it on the table. Okay, I'll stop ranting now.

JR: How do you identify an employee’s strengths?

JJ: Well, I certainly ask them and listen to their own insights, and 70 percent of the time they are right. Sometimes people WANT to be good at something but they just aren't, sadly!

I also go to meetings with them and watch and listen. How do they persuade people? How do they use data? Are they good speakers? Are they decisive or super consensus-oriented? And I also talk to other people about them. [footnote: God, I hated it when she first did this to me, but I got used to it.] Whenever someone new joins my team, I ask three to four people who have worked with them before what their "super powers" are and what they need to work on. Then I do that a second time about four to five months later because my own perspective will have evolved by then. Also, when I see someone really having FUN doing something at work, it's usually because they are good at it. That's a key sign.

JR: How do you know when an employee can’t be saved? (This was something you always knew so instinctively, but I really struggled with, especially in the beginning, I was really soft and hopeful and let people take advantage of me.)

JJ: When I have coached someone carefully and repeatedly, but they can't improve, that's the first sign. Then when I see that their co-workers are frustrated and avoid the person, that's the sign the ship has left the harbor. When a person can't gain the respect of others on the team, that's when I know they have to go. This is a really hard lesson to learn. I used to wait nine months to a year trying and trying to coach someone through something. Now if I'm expending huge amounts of energy and seeing no return in three to four months, I make the call. It's really best for everyone in the end.

JR: I talk about boundaries in the book —how they’re critical and everyone tells you to get them, but sometimes this can be easier in theory and harder in practice. How do you create boundaries, i.e. find a balance between nurturing your staff versus letting them rely on you too much so they’re not actually learning for themselves?

JJ: Well, this is really different for everyone — for every manager and for every employee. For more junior people they need a lot more coaching and are insecure and you can't just say, "Hey, figure it out" in all cases. But managers, in general, coddle people too much. I tell everyone on my team, "You are very welcome to come say to me ‘I just want to vent for a minute.’ But if you are bringing a problem to me that you want me to help SOLVE, then you better have some ideas how. You better have asked yourself, "What are 2-3 options here to work through this?" and you should explain them to me in addition to laying out the problem. If you don't, I'm going to say, "Well, what do YOU think you should do?" It's amazing how shocking that question can be to some people.

JR: What are the biggest mistakes you see young employees make?

JJ: Wanting to move too fast. Thinking there is a right "fast track" career path and they need to get on it. I always tell people "Unless you are independently wealthy or start a very successful company you're likely going to work for 30 to 40 years. That is a hell of a long time. Try on a lot of sweaters and see which suits you best!" Then I also see people wanting to seem perfect. They can't say "I made a mistake" or "I don't know how to do this — can you help me?" This is even hard for 50-year-olds! But we all have to learn to do this. Honesty and self-reflection are the only roads to business success — well, really, life success.

JR: How do you turn around bad morale—especially when you’ve inherited a team?

JJ: Identify people who have gone toxic and are spreading bad energy. Tell them to turn it around or leave. Find people with talent and a good attitude and promote them. And lead by example — I expect positive action and I will bring it to you. Would you like to join me? If not, you're on the wrong bus.

JR: What are the most important qualities of a great employee?

JJ: Hustle. That's the single most important quality. Then willingness to try new things, admit failure, learn and move on. A desire to work with other people honestly and openly. If you can't put your ego in a box and row the boat for the larger team, we're all going to lose. And taking your WORK seriously, but not taking yourself too seriously.

JR: So what are the most important qualities of a great manager? I have an idea, but I want to hear yours. 

JJ: I think it is a very delicate balance of hard and soft. A manager needs to be caring and kind. People will only follow a manager if they think that person wants them to win. But on the hard side, a manager needs to give tough, clear, fair feedback. They can't sugar-coat or sit on problems. When something is going wrong with a team or if a person screws up, a manager has to talk it out immediately and very openly with the people. And then they have to be able to rise above the daily chaos of the business and ask, "Are we doing the right things? Are we seeing the forest from the trees clearly? Is there a better way we should operate?" Then they have to identify the right people to help them answer those questions.

JR: I am going to navel-gaze for a bit here, so forgive me, but… Looking back, I realize I was kind of a pain in the ass when we first started working together, I had a chip on my shoulder from my previous boss and from bosses before her—I’d been mismanaged for a long time. By the time we met, I was down on the company, I was pissed a lot of the time and had an attitude problem—the kind that is totally annoying for a manager to have to deal with. I had the potential to become great at my job, but I don’t think I was showing this to you. In fact, we worked together for several months before I really started pulling my weight and showing you what I could do. But you kept encouraging me, you kept checking me, you told me when I was inappropriate, you set high expectations and specific goals and you praised and rewarded me when I did something great. My performance reviews from you were concrete and specific and sometimes even harsh but they made me want to get better. You changed my life professionally—and arguably personally too. I guess my question is: How did you know that I had potential? How did you know how to manage me under all of my bullshit? And more broadly: How do you motivate disgruntled employees?

JJ: People are generally pissed off in a job for one of two reasons: Either they are not good at what they do and they secretly know it and everyone else knows it and they are stuck and angry, OR they are smart and hungry and they have had shit managers and want to contribute more but don't feel they can. When I met you, I knew you were the latter in about 48 hours. When I talked to you, I saw passion immediately. I asked you questions about the team and the business and you were animated and had strong opinions. You clearly cared about quality work and you told me "I want to win." And I knew you would work your ass off to do so. I could also see that you had not had good managers who cared about your ideas and also held you accountable. I thought if I did that — and if you saw me do that for the broader team — I could win some of your faith back. But mainly I just let you do what you knew in your heart that you could do: Identify good people, hold a high-quality bar for work, set clear goals, and then work to surpass those goals. You did that in spades in record time. And you always had a sense of humor and were quick to make a joke, which makes working so goddamn hard tolerable. In fact, it makes it fun.

Jessica Jensen is the Head of Products, Platforms & Insights for Business Marketing for Facebook. Jennifer Romolini's Weird in a World That's Not, comes out June 6th. They're both kickass bosses.

Want more good boss advice? Check out Jenn Romolini's Office Hours Interview.

(Lead Image via Getty; Additional Images courtesy of Jennifer Romolini and Jessica Jensen)

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