What Happened When I Stopped Trying To “Out-Man” The Men I Work With

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Several years ago, Kirsten Wolberg was interviewing with a major Bay Area company when the hiring manager urged her to try for a different role than the one she was gunning for. It was an executive technology role, and there were no other women at leadership levels at the time, Wolberg recalls; even the HR manager was a man. Still, she says, “I didn’t get the sense in the interview process that there was a specific focus on hiring a woman. I think it was very specifically tied to the skills that I brought to the table.”


So when Wolberg got the job, she hit the ground running, only to halt in her tracks a few months later after receiving her first 360-degree feedback review, based on anonymous input from her coworkers.

In her own words, condensed and lightly edited for clarity, Wolberg, who’s now chief technology and operations officer at DocuSign (and has held tech positions at PayPal, Salesforce, and Charles Schwab), tells Fast Company how unprepared she was for the criticism she received–and for her colleagues’ changed attitudes after the unconscious bias training that followed.

Related: I Was The Only Woman In My Company For Two Long Years

“A Punch In The Stomach”

I was pretty oblivious to a lot of what was going on. This particular company would do 360-stakeholder reviews roughly after the first hundred days on the job, just to make sure the executives were onboarding in a positive way. When I sat down with the readout of my 360, I realized that things were not great, and in fact they were quite bad.

Kirsten Wolberg [Photo: courtesy of Kirsten Wolberg]It was the first time in my career I ever heard this kind of feedback. I had heard other women in technology tell me they were getting this kind of feedback, but it never happened to me. The things that I heard most frequently were that I was too ambitious and I was trying to position myself as a successor to my boss, [which] was deemed as inappropriate and “too aggressive.”

The other thing I heard was that I really was focused on me and not the team. One of the things I’ve always prided myself on–and I’ve always focused on–is the team. So to hear that was like a punch in the stomach. And then the final [criticism] was just a lot of style points on “abrasiveness,” “too brash,” “not listening,” and “talking too much.”

There were two individuals who were peers of mine who actively said, in every forum, that they were trying to be a successor for my boss’s role, and I never expressed [anything similar]. It wasn’t my ambition. So to hear over and over that people have this perception that this is how I was positioning myself was like, “Wow! It has zero truth, but what must I be saying, what must I be doing, to be giving this impression?”

Related: The One Word Men Never See In Their Performance Reviews

I really started to second-guess myself. Every time I opened my mouth I was like, “How is this coming across?” I wrote out bullet point by bullet point: “These are the things that I’m going to do to address this feedback.” I focused on changing my style, being a lot quieter, and being clear about what my career ambitions were.

[But] I also started looking for a new job, because I really felt like I was in a place that didn’t get me. I’d just taken the job, and I was super excited about it, [but] if I wasn’t going to be able to be myself and I had to constantly think about everything before I opened my mouth, I wasn’t in the right place.

“I Think I Owe You An Apology”

That was about the time when the company brought in a professional organization that has done a lot of unconscious bias training. What the organizer recommended was that instead of bringing all the women together, we should actually bring the men into this conversation and really start focusing on educating the men around these biases.

My boss and my peers were part of this training, and–literally to the points that were on my 360 feedback–[the training experts] said, “Well, this is what a woman will hear, and this is what’s driving it,” through the entire two days of the training.

My boss came up to me afterward and he said, “I think I owe you an apology because I think that a lot of the feedback that I gave you through this stakeholder-review process was actually more about the unconscious bias that exists and the fact that you’re a woman.”

I felt vindicated. And also, I felt like I had permission to be my authentic self–to really show up as a woman in that space. That’s not to say that all unconscious bias went away after that–because it still existed–but I had my confidence back because I had reinforcement, if you will, that what I was feeling wasn’t just me.

Related: “I Felt Like I Was Representing Every Black And Young Person”

But even though we [had] the unconscious bias training, this leadership team [later] went on an offsite [where] one of the team-building activities we did was that we raced cars on a racetrack using high-performance vehicles. I got out onto the racecourse and they’re all flying around at 160–170 miles per hour, and I’m driving the inside of the track at 55 miles per hour. It was clear that I wasn’t enjoying it. Then, as we were getting on the bus to go back to the hotel, one of my peers said to me, “Don’t worry, next time we’ll just get a mani-pedi with you.” Those kinds of things just continue to happen.

I do think the overwhelming majority of men want to do the right thing and think they are doing the right thing. It’s not until they get the training, [and] see what they’re doing and how they’re doing it and how unconscious it is, that the changes can really happen.

“To Out-Man The Men”

I’ve been in technology and financial services most of my career, two of the most male-dominated industries. I always felt like the only way I was going to be able to compete was to out-man the men–dress like a man, swear like a man, talk like a man, shoulders back like a man, just constantly fighting like a man. It is absolutely exhausting. And over the long run, it’s not successful.

It wasn’t until this happened that I realized I’m never going to be a man, I’m never going to out-man the men. To truly be an authentic leader, I need to be a woman. I need to embrace all that. How I engage in debate is different, in the sense that it’s not as in-your-face as it used to be. I also show more emotion and vulnerability in the workplace than I ever did.

My boss at the former company [who had apologized to me] turned out to be my biggest cheerleader, my biggest ally, and to this day is one of my greatest mentors. There’s a lot of space for men who can continue to help women at every level to continue to grow in their careers. And even though they could start out in a very biased place, men can turn out to be some of the greatest allies for women across the board.

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