Women in Leadership 2020: A powerful journey in a single day

Women in Leadership 2020 was the first event of its kind for Vistage.

Bringing together a national, virtual audience of hundreds of female Chairs, members and member candidates, the event on Aug. 21, 2020, raised the bar on the depth and value attendees can experience within the “new reality.” And it illuminated with heartfelt clarity the sisterhood that thrives within the Vistage community.

In informal networking sessions, targeted learning breakouts and guided discussions, 700+ women gathered in small groups with peers they’d never met previously, to speak candidly about what it means to be a woman in leadership. With laughter and an outpouring of honesty, the women of Vistage shared professional challenges and triumphs, and some lighter insights too — connecting as never before with their female peers across the U.S.

Below find three key learnings from a game-changing day, each packed with supporting takeaways.

1. With the right mindset, you can harness headwinds to make you a better, stronger leader.

Self-doubt. Change. The unexpected. As for a pilot in flight, headwinds arise for business leaders that are very much beyond your control. What is in your control, is how you respond. “Risk is required for growth,” shared our first keynote, Col. Nicole Malachowski, USAF (Ret.).

Col. Nicole Malachowski, USAF (Ret.)

For Nicole, the headwinds in the sky never held her back. It was with feet firmly on the ground she faced challenges like overcoming gender bias to become the first female Thunderbird pilot, redefining “work/life” balance, and persevering through grave illness.

“Choose an unscripted life,” Nicole declared. And take caution to not write yourself out of it. “The only way you’ll figure out what you’re capable of, is if you try.”

That’s not to say you should over-extend yourself. In a suggestion many attendees found novel, Nicole shared a secret to her success was in setting clear boundaries, and in working to 85% — not 100%. She explained, “You can’t live your life to 100% every day in peace time. You need to reserve something for war.”

At the peak of her success, illness left Nicole bedridden — unable to move, speak or talk for nine months. When facing unexpected hardship, “yield to overcome,” Nicole advised. “It’s not about resilience, it’s about resurgence.”

As the event chat panel filled with comments and personal anecdotes from attendees, it was clear Nicole had struck a chord, sparking lively guided discussions on harnessing headwinds of their own.

“Believe those who believe in you,” Nicole urged. “You are surrounded by those women right now.”

2. Care personally, while challenging directly.

Our second keynote speaker Kim Scott was the yang to Nicole Malachoswki’s yin. Presenting a tangible framework drawn from her best-seller, “Radical Candor: Be a Kickass Boss without Losing your Humanity,” Kim pulled no punches as she shared good, bad and ugly personal anecdotes, including how her first experience with Radical Candor™ came from a frank exchange with Sheryl Sandberg.

Kim Scott, Best-selling author and co-founder, Candor Inc.

In no uncertain terms, Sheryl told Kim just what she needed to do to improve as a speaker. Her feedback was direct, it was actionable and it was heartfelt. And this is the core of Radical Candor.

An intersection of art and science, Radical Candor is in large part about avoiding the following leadership pitfalls:

  • Obnoxious Aggression™ Challenging directly, without caring personally.
  • Ruinous Empathy™ Not being honest, in order to spare short-term feelings. 
  • Manipulative Insincerity™ Backstabbing. Passive aggressive behavior. Insincere praise. 

“Common human decency is something you can offer to everyone in your organization,” Kim countered. “At the core of management, is a good relationship.” 

The best way to introduce Radical Candor into your organization, is to ask for feedback: 

  • Ask a question that invites engagement.
  • Wait for a response.
  • Listen with intent to understand.
  • Reward the candor!

Kim explained, “Your job as a leader is to paint a picture of what’s possible for people.”

As attendees broke out to discuss, the wheels were turning — Kim’s challenge of being human vs. professional resonating. Coupled with Nicole’s declaration, “all you have is the runway ahead of you,” attendees now had tools to optimize their leadership AND the motivation to fuel it.

3. Be the pebble in the pond.

Sarita Maybin, Communications expert and author

Following an extended break, Women in Leadership 2020 attendees reunited to close the day in gratitude. Communications expert Sarita Maybin led an interactive journey through how to stay positive and hopeful even in challenging times, and real-time insights poured in.

The women of Vistage freely shared just what is keeping them going, with an overarching feeling — we’re all truly in this together. Sarita challenged attendees to “be the pebble in the pond,” continuing to support one another in embrace of the notion, even one small move can make big ripples.

Thank you to all who joined us on Aug. 21, and thank you to our event sponsors.  In the words of Vistage member and event attendee, Tamera Wobbe, “Let’s do it again!”

We most surely will.

Vistage members may visit the post-event page here to access all of the day’s presentations, resources and more.

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