Friday Book Club | The Upside: Better Outcomes When Everyone Plays.

October 16, 2020

Friday Book Club | The Upside: Better Outcomes When Everyone Plays.

May 29, 2023

Diane Flynn and Patty White are co-conspirators of mine and they’re popular MEA guest faculty. Their book, “The Upside,” showcases the business case for gender diversity and specific actions each stakeholder can take to build more inclusive cultures.

They have facilitated workshops around leadership and personal branding for audiences at the Stanford Business School, Harvard Alumni Association, Visa, Cisco, MEA, and other industry leaders. Helping women live lives of influence is their passion, and they approach their clients with support, confidentiality, and care. It’s an honor to sit down with them to talk about this book.

What surprised you most in your research for the book?

So many companies we work with are progressive and enlightened when it comes to gender equity that sometimes it’s easy to think we’ve solved the problem. Yet in researching the book, we hosted groups of highly accomplished women at our homes to hear their stories. We were shocked by how much is still happening on a daily basis--both consciously and unconsciously -- to hold women back. Women, and all underrepresented groups in the workplace, still have a long road to travel until we truly achieve parity.

What was particularly surprising to us was what we learned about performance evaluations. The words used to describe the work of men and women performing arguably the same work in the same manner were very different. Men’s evaluations included the words “accomplished, high-performing, and assertive”; Women’s called them out for being “abrasive, aggressive, and bossy.” Until we recognize the gender bias that shows up in performance reviews (and job descriptions, but that’s another story), advancement (and recruitment) of women will be shortchanged. Men are still largely promoted based on potential, while for women, it’s proven performance.

Let's talk about flexible work arrangements. Much has changed since you wrote the book. Has the Work From Home (WFH) experience during the pandemic changed the way you would describe/recommend flexible work arrangements?

We devote a whole chapter to flexible work arrangements. We believe this is one of the five most impactful levers that improve a company’s ability to attract and retain women. Back in February, before the shelter-in-place mandates, most clients were skeptical. One client specifically asked us, at the start of the year as our book was about to be released, that we not discuss flexible work when meeting with their leadership team. This client is an older, white male -- the exact demographic that, according to BCG’s research, shows the most skepticism regarding flexible work arrangements. In April when we closed out a video meeting with a question about how he felt WFH was working, he developed a sheepish grin and replied, “Best thing ever.”

Most companies have seen that WFH has not impacted productivity, and many companies envision fully distributed or hybrid workplaces in the future. While this is a positive trend for women, the sad reality right now is that women are experiencing a lopsided burden of caregiving and home-schooling. This untenable arrangement is the reason 27% of working moms are reportedly considering leaving the workforce right now and 61% are considering a job pivot, largely to something entrepreneurial.

While flexible work is desired by most employees and the pandemic has proven its many benefits, we are stuck in challenging times with the full benefits not being realized. In the short-term, we may sadly backtrack on the positive momentum of gender parity in the workplace.

The last 'lever' you offer is the idea of visible role models. How do you ensure when a visible role model is an 'only' that she is not considered/treated as a token?

Many women worry about being the token woman in the boardroom, C-Suite, or on the leadership track. We encourage women to reframe this. They should consider themselves to be trailblazers rather than tokens. Someone has to be first, and we need more women to step up and provide the example of how cognitive diversity positively impacts teams. The women we coach often admit to some version of “Impostor Syndrome,” that feeling of being a fraud and with the concern that sooner or later, someone will find out. Addressing this lack of confidence is often a key first step in helping women understand that their leadership will both inspire and pave the way for many young women.

How does unconscious bias hold women back in the workplace?

Unconscious bias holds women back in a similar but perhaps more insidious way than the conscious biases that women have been up against for years. We see it in hiring situations when objective criteria get overshadowed by ‘culture fit’ which in many cases can translate into ‘looks like us’ or ‘the kind of person I’d want to have a beer with/play golf with after work.’ There are even some very seemingly innocuous situations like when a male manager purchased roses for the women employees attending a business dinner, or that they receive jewelry as a corporate gift at the same time as men are receiving books on the latest leadership practices. Men who notice these biases and discrepancies in treatment can play an important role as an ally, by pointing out what they see. Similarly, women need to be open to considering and welcoming feedback about biases and stereotypical judgements they may unwittingly make. The nature of unconscious bias makes all of us unintentional offenders at one time or another so a best practice when you see it is to extend the grace that you’d like to receive.

You have a whole chapter aimed at men? What's the best advice for men?

The best advice for men is the best advice for everyone --- be human, compassionate, vulnerable, and seek to understand. Our Inclusive Leadership Training Program has four key modules. We start with one’s mindset. One must commit and be intentional about making a difference and creating a more just and equitable workplace. Next, it’s important to listen. Understanding other perspectives can open pathways for new thinking. Thirdly, speak, even while knowing that you’ll sometimes get it wrong. Be willing to be vulnerable on the path to new learning. The worst action is inaction. Finally, commit to being an ally. Mentor other women, speak up when they are overspoken and underheard, address unconscious bias when observed. All of these steps will help produce a workplace where employees thrive and the best work gets done.


Diane Flynn and Patty White, co-founders of ReBoot Accel, have helped thousands of women develop skills to lead with impact and influence. They also consult with companies around creating diverse and inclusive cultures. They received their MBA’s from Harvard and coaching training from CTI, and their work has been featured on The Today Show, WSJ, Forbes, ABC News, NBC, PRI's The TakeAway, and the HuffPost.

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