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Leadership as continuous improvement

Eighteen months back when I wrote a piece on authenticity at work, I had just come off a series of challenging project environments and was feeling stifled. Despite recent professional successes, I still felt the pressure to cover—to downplay my differences from the mainstream— rather than risk a possible discord with colleagues and clients around my identity. This apprehensiveness of “being myself” (a queer, childless woman with a transgender partner) was only amplified as the United States and many other countries around the globe became further politically polarized. As water cooler chit chat on current events became dicey and many arenas recommended “avoiding politics at work” altogether, I struggled to find the line between speaking my truth and picking my battles.  

1.5 years later the political climate feels about the same (or worse? It’s hard to tell), but I know that I’ve evolved. I’ve launched a few projects, led two fantastic teams, and got promoted to a Principal consultant (exhale.) As a result, I’ve had many up and coming Thoughtworkers approach me for advice.

Just last week I had a coaching conversation with a TWer; it was mid-afternoon, and I was coming out of a 2-hour video meeting. Sitting in the New York office lounge with a colleague (another thirty-something white woman), I was feeling drained. I was tempted to reschedule our lunch, but it was the only open slot on my calendar that week, and I had already canceled once. I knew she was interested in investing in a technology career, so I put on my ‘benevolent mentorship’ face and tried to compose myself as she asked for “honest guidance” on “anything that feels relevant to share.”

I turned the conversation back to her and asked what was motivating her career investment. Over lettuce wraps and unsweetened iced teas, she spoke about her art degree and various creative affiliations, dissecting the headspace she had been in as each life phase unfolded. As she moved on to discuss her market campaigning experience, I realized we had a lot in common and began reflecting on my own experiences earlier in my career. Her explanation went on, and I started getting impatient, remembering the many moments that I overshot a conversation or blew a negotiation in feeling the need to explain myself; or a sense that all of the details mattered. As the minutes ticked by I went from interested to amused to frustrated and finally blurted out:

“One thing you could consider if you want to be seen professionally is to figure out how to condense your statements.”

The words hung in the air. I’m still not sure if the content of the message was necessarily wrong, but it definitely felt bad as it came out, and looking across the table I could see that it had struck a negative chord.

The awkwardness shifted our conversation, which turned to network building, but I remained distracted by the exchange. Did I overstep? After all, she asked me for some real honest advice. Her verbosity was surely going to create an issue for her in her career. Wasn’t it my duty as a mentor to speak up?

Later that night it was still gnawing at me, so I tried to put myself in her shoes. I thought back on some dialogues from my early working years. I remembered one time that a director commented on my clothing, and another time a manager gave me feedback on my presentation style in meetings. Both incidents were presented as “advice,” but one had felt helpful and the other felt icky and judgmental. Similarly to my weird interaction with my mentee, the words themselves weren’t inherently bad, but there was something about the vibe that was off. I can still remember the feeling, the body language, of this subtle attack “trojan-horsed” into a weekly check-in meeting.

But why would I want to attack a fellow Thoughtworker?

I’ve come to the conclusion that it’s due to covering. As a woman working in the tech world, the past 15+ years have included a lot of self-censorships. Out of fear of being seen as long-winded, I edited my words. Out of concern of not being taken seriously, I adapted my wardrobe. Sitting on the other side of a table from someone (seemingly) without those concerns, I felt two things; fear that she wouldn’t be successful as a woman in business and jealousy that she had gotten this far without making those sacrifices.

There was still a voice inside my head, saying “Well, everyone has to conceal some part of themselves at work, regardless of identity or even what they do.” But while that may be true, it’s also true that there are many ways to be successful. We all know verbose people or controversial dressers who are still successful. And while most of those people are white men (at least in my world), that is beginning to change. And I want it to change.

I want her, and other people that may face discrimination in tech, to feel like they can be a part of that wave—or at least that it’s up to them to decide how to navigate their environment and what compromises are right for them. My advice-turned-microaggression likely stemmed from the pain of feeling I had no choice but to sacrifice out of fear of discrimination; and the retrospective questioning of just how true that was.

Here’s the bottom line: for a woman entering tech today, I have a responsibility as a leader. I want her to understand the obstacles she’s up against, but also to trust her instincts on what she needs to retain her authenticity at work. Or, as my mentee put it, “to exploit strengths instead of focusing on weaknesses.”

I went back to my colleague a few days later, acknowledged my error, and apologized. I also asked her permission to write about the incident. Between those two conversations we were able to connect at a level that was much deeper than where we started, and when she thanked me for my vulnerability, I felt relieved, more in line with where I wanted to be—acting in her best interest.

So as Thoughtworks looks back on 25 years, I’m looking back on myself, seeing both the ways that I’ve progressed and other aspects that still need time to mature. I’m so grateful to be in a professional community of people who are open to examining complex topics and pushing through the messiness. Here’s to another 25 years of experimenting, growing, and logging more time towards continuous improvement.

Disclaimer: The statements and opinions expressed in this article are those of the author(s) and do not necessarily reflect the positions of Thoughtworks.

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