Diane Flynn leads a seminar that helps women to identify professional strengths that also fulfill them.

Focus on the Upside With Diane Flynn

7 Author Insights on Diversity in Business from ReBoot Accel CEO

Elisheva Marcus
Published in
5 min readJul 27, 2020

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In March 2020, our lives were globally disrupted. One positive occurrence on March 6th though was the independent publication of The Upside: Better Outcomes when Everyone Plays, by a power author team of Diane Flynn and Patty O’Brien White.

The book’s two authors are the cofounders of Reboot Accel, empowering women to lead lives of impact and influence. Having helped thousands of women so far, they know first-hand about the importance of women in the workforce.

This article features an interview with one of the authors. Read on!

In The Upside, the authors posit that businesses perform better when gender diversity and gender equity are involved. Typically, at every level of an organization but particularly at the top. So the natural question is: what circumstances best facilitate that? Flynn and O’Brien White consulted mid to Fortune 500 companies throughout the US, public and privately owned, across a spectrum of industries, as well as culled from their own experience supporting women to achieve career growth to find out.

Diane leads an interactive workshop through ReBoot Accel’s programs

They draw upon a breadth of combined expertise: both women received MBAs from Harvard and together have decades of experience at companies like BCG, Electronic Arts, HP, and IBM. As executive coaches, they inspire leaders to maximize results and personal fulfillment. Beyond their work with corporations, they’ve also facilitated leadership workshops for audiences at SXSW, the Stanford Business School, and Harvard Alumni Association, just to name a few.

Their new book explores how diversity drives innovation, engagement, retention, and bottom-line performance. It shares how the most diverse companies are benefiting, along with pitfalls to avoid.

The Upside: Better Outcomes When Everyone Plays

I recently wrote about Diane’s inspiration to start Reboot Accel and how you can overcome obstacles when returning to work. So check that out.

In the interview below, you’ll get deeper insights into Diane Flynn’s thinking and future plans, as well as definitions of useful terms to know. Let’s dive into seven questions for Diane as she provides examples and growth tips.

1. Why is it so vital to amplify female voices?

DF: It’s critical to amplify the voice of anyone in the room whose voice isn’t heard, and in large part, that’s women. “Amplification” was developed during the Obama administration when the women on his team realized they were either being talked over or dismissed by men. They realized they needed to amplify each other by repeating what was said or insisting the conversation return to the dismissed comment. If teams want to benefit from diverse voices around the table, these voices must be heard.

2. What’s the impact of women on a company’s board or C-level?

DF: Several studies show that having women on boards provided better acquisition and investment decisions and less aggressive risk-taking, yielding benefits for shareholders. Research from HBR suggests one potential reason: Having female board members helps temper the overconfidence of male CEOs, improving the overall decision making for the company. I joined a corporate board recently and find that my voice brings cognitive diversity — as a woman, a mom, and as someone who works in the gender equity space.

3. How can we keep chipping away at imposter syndrome?

DF: Lack of confidence is the single greatest struggle I see women face, whether they’re new in their careers or have executive status. I’m not entirely sure why this is the case, as these women have so much to offer and excellent experience as proof. To address this, I suggest reframing self-limiting beliefs and revisiting positive feedback. Instead of saying “I’m too old,” try saying “I bring valuable wisdom, pattern recognition, and connections.” I encourage women to post positive affirmations in visible places so they can remind themselves of the skills they bring. Sometimes it’s helpful to do a deep dive into what’s behind this lack of confidence. Asking “5 levels of Why” can help peel the onion and get to the root cause of any insecurity.

4. How can people best brand themselves for the career they want?

DF: We have a number of free resources on our rebootaccel.com to address one’s personal brand. It starts with an audit — what strengths do I bring? What impact do I want to have? Who do I want to reach? Then build a 30-second “elevator pitch” that encapsulates these. Make sure all your social media profiles reflect this brand in a strong and consistent way. And be sure to “live” your brand in how you dress, speak, and post.

5. Can you explain what reverse mentorship is and offer an example?

DF: Reverse mentorship is when two people of different generations mentor each other. Many companies have tried this with great success. Jack Welch popularized the concept when he led GE and discovered that it increased millennial retention, promoted a competitive advantage in innovation, and cultivated a climate of inclusivity. It’s a way to blend digital IQ with experiential EQ, providing mutual benefits to both mentor and mentee.

6. What do you mean when you talk about “capitalizing on luck”?

DF: I’m a believer that one frequently manifests what’s put out there in the universe, providing you have the skillset and drive to deliver. By envisioning it, speaking it, and sharing it with others, opportunities often open up for me. I’m an extrovert and enjoy speaking with and learning from people. This informal networking is key to capitalizing on luck, as I’m continually amazed by the serendipity and new opportunities that emerge from seemingly random conversations.

Participants at a ReBoot Accel event mingling during a break.

7. What’s next for you or for ReBoot Accel?

DF: This recent awareness around social justice has caused me to do some deep soul-searching. I desperately want to be part of the solution, and I’ve spent a great amount of time reading, listening, seeking to understand, and trying to determine how I can supply a piece of the puzzle. This has led to many new initiatives for ReBoot Accel, including bringing in a Diversity Director who conducts Conscious Inclusion Training, along with partnering with four organizations that serve underrepresented groups. My goal is to bring our services to a broader audience and to drive positive social change in organizations. Black lives matter, and there are far too few women of color in corporate America, especially in leadership. I hope to extend our services to help correct this imbalance and create a world of justice for all.

To learn more, visit Reboot Accel on Twitter and Facebook.

Thank you for your insights and time, Diane. Hopefully this impacts and uplifts many people!

If you appreciated this article, please clap 👏🏽 for it so more people discover it. Feel free to follow me Elisheva Marcus for more stories on founders and innovation.

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Elisheva Marcus

Reporting from within a Venn diagram of health, tech and empowerment. Berlin-based. Internationally minded. Comms @ Earlybird Venture Capital