What Happened When I Stopped Trying To Out-Man The Men At Work

Kirsten Wolberg is the Chief Technology Officer at DocuSign. The views expressed are her own.
Yet for a long time, I didn’t think about being a woman in a male-dominated field. I just focused on being the best.
I grew up in Alaska playing basketball and ice hockey. In the classroom, I ‘set the curve.’ I am competitive on every level, but mostly with myself. When I entered the very male-dominated worlds of financial services and technology, I didn’t give a thought to gender or that I was often the only woman in the room. I knew how to compete. I studied how my peers succeeded and modelled their behaviour. I started dressing like a man (blue suit with that God-awful silk bow tie), swearing like a man, dominating conversations like a man. And it worked. Until it didn’t.
I hit the wall when I took a role as a senior technology leader at a large Bay Area company. I was the first and only female leader on the team. I approached the job with the playbook that had served me so well – shoulders back and chin up, ready to tackle anything. I was driven, ambitious, and wanted to make an impact.
Quickly, I was labeled “too aggressive” and “constantly posturing for the boss’s job” – actual quotes from a very negative performance review. The feedback didn’t sit well with me. My truth was nothing like what I was hearing. The more I fought like a man, the worse my situation became.
It was a turning point for me. I realised then that I can’t ‘out man’ the men on my teams, and I shouldn’t have to. It took me more than 20 years to grasp: I will never be seen as a man, treated like a man, or have the same rules as a man – so I need to embrace my feminine, authentic self. I need to celebrate the innate and unique gifts I bring to every workplace and every problem. When I made this shift, it didn’t change the environment I was working in, but it made it easier for me.
I stopped fighting so hard. I listened to Deborah Gruenfeld, a professor at the Stanford School of Business, talk about power and influence and how our bodies speak louder than our words. I realised that I could try to soften my words, or change my language and it wouldn’t matter. So, I stopped physically posturing as a man, and I finally gave myself permission to relax my body. Suddenly conversations could be conversations versus confrontations.
I tapped into all the emotions that lived within me – joy, fear, love, anger, surprise, disgust, sadness, courage and shame – and learned they all had a place, and that I could bring them to work. And I did. My peers responded, my staff responded, my boss responded. Best of all, I finally felt like myself. In honouring my femininity, I was able to be a better leader, and influence to greater impact.

"I will never be seen as a man, treated like a man, or have the same rules as a man – so I need to embrace my feminine, authentic self."

Kirsten Wolberg, CTO at DocuSign
Fortunately, my own revelations came as the world started to wake up to the depth and breadth of unconscious bias in tech. The environment is changing, albeit slowly.
The boss that gave me the harsh feedback went through unconscious-bias training. After class he came to me and apologised, realising the feedback directed at me had been rooted in the fact that I was the only woman on the team rather than in my specific behaviour.
Bias shows up everywhere in the workplace. It’s in the way job descriptions are written (the more specific and technical, the fewer female candidates apply); the make-up of the interview panel (if diversity candidates don’t see anyone like them on the panel, they’ll be less likely to accept the job); and in salary negotiation (women, who historically have earned less than men, start negotiating from a lower position, perpetuating the delta).
And all of this bias happens before a woman even joins a company. Bias continues into the job, as managers use language to describe men as leaders and risk takers, and more communal language to describe women as relationship oriented and empathetic, which leads to promotion at faster rates for men.
Changing how you show up as a female tech leader in the office will not break through all of this inherent bias. Clearly, we still have significant work to do to change the statistics. As women, we have a responsibility around how we are showing up – and how we are asking men to show up for us. When we truly live into our power, we will be best positioned to make it happen.
I have just taken a new role as Chief Technology and Operations Officer at DocuSign and this unapologetic woman is going to use every ounce of her power to make a difference for women here and everywhere.
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