Women at Docusign: Why Confidence is a Critical Trait for Female Leaders

By Kayleigh Kahlefeldt - Marketing Director, APAC.

Today, I joined a gathering in our Sydney office to meet our visiting CTO, Kirsten Wolberg. It’s always exciting for us to have the chance to get closer to the roles that define the direction we take in the work that we do. And, I should point out that, despite the distance, we’re not short of executive visitors here in APAC. But, the reason I was personally excited to have an opportunity to hear from and question Kirsten is because of something I recalled her saying during a similar audience – this time in front of a global marketing crowd – at our annual kick off. Asked a question on whether she was going to prioritise a certain project, Kirsten simply answered; “No”, elaborating briefly that the challenge was notoriously impossible to resolve in a way that would satisfy everyone. She talked instead about what we would be focusing on, and encouraged active discussion around this. Far from appearing dismissive, she came across as decisive; which I found immensely reassuring.

It occurred to me that excessive empathy sometimes manifests as indecisiveness. And, it seems to be largely a female affliction. In the same situation as Kirsten I might have (ok would have) taken a more apologetic approach. And, through being conciliatory I undoubtedly would have appeared unsure. New York Times bestseller The Confidence Code [theconfidencecode.com], calls out this issue exactly: that women spend a great deal of time unintentionally undermining themselves.

Kirsten’s visit to Sydney revealed a little of why she refuses to fall into this trap.

She spoke of the importance of displaying confidence, as a female leader. And, to demonstrate how confidence factored in the building of her career, shared a few stories from her journey. She talked about her massive ambition and determination as a youth growing up in Alaska, which ultimately took her to San Francisco. She shared the peaks and troughs of her pursuit of a career in the male-dominated (as it was) finance sector, including the collapse of the banking and loans industry leaving countless roles without hope. Her response? To become a consultant, advising to these roles. (If you’re not part of the solution you become part of the problem)

Kirsten recounted her path through curve ball after curve ball, including the dot com disaster, family sickness and the need to juggle a high-stress career with young children. These are events that knock women down every day in the climb to the top. Kirsten, however, repeated the same phrase after each tale - “…and, this turned out to be very lucky for me…” – as she went on the explain the incredible opportunity she spotted and pursued from among the ‘wreckage’.

What became clear is that Kirsten had backed herself all the way. And, when she told the story of how she interviewed for a technical role with Salesforce, jumping up to whiteboard her thinking to address a current challenge the company was facing in its early growth stages and then following up with a three page proposal on how to address it specifically, it’s hardly surprising she landed the top role of CIO instead.

I found a great deal of inspiration to bolster my very British demeanour during Kirsten’s visit, which I can crystalise into the following pieces of advice for women looking to climb the leadership ladder:

  1. There’s always a way forward – find it. Never give up until you run out of what Kirsten Wolberg refers to as “Alaskan grit”. If you have turned over your current challenge, backwards and sideways, and still cannot glimpse opportunity then by all means give up. But truly, has that ever happened to anyone willing to put in the effort?
  2. Take advice. And, sometimes leave it. Have confidence in your own opinion, own it and see it through. If you’re wrong, there will undoubtedly be a big opportunity waiting for you in that learning. And if you’re right, you’re on the fast track to success! Had Kirsten been swayed by her friends and family in the early days, perhaps she might never have left Alaska in pursuit of her dreams.
  3. Be decisive. For many of us, the urge to please everyone can be the show stopper to our career. Instead, focus on communicating your decisions with confidence and place your energy into bringing those around you on board instead of fueling the fire of discontent through protracted discussion on what didn’t happen.

If you would like to join the Docusign team in Sydney, check out our careers page for available positions.

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