Podcast: Diane Flynn, How Companies Should Respond to Changing Workplace Demographics

Diane Flynn, Co-Founder and CEO of ReBoot Accel, talks with Chris Riback for Working Capital Conversations
Diane Flynn, Co-Founder and CEO of ReBoot Accel

From gender-based pay gaps to leadership roles, advancement opportunity to corporate culture, the treatment of women in the workplace – and how to enhance growth opportunities for women executives – is and has been under continual focus.

But now this focus is frequently combined with a new, and growing trend: The aging and multigenerational workforce. The numbers may surprise you: The number one growing demographic in today’s workplace is women over 55. In fact, the number of people over 55 is going to be 25% of our workforce in five years.

The statistics come from Diane Flynn, Co-Founder and CEO of ReBoot Accel, accelerating the careers of women in the workplace and consulting with high-growth and Fortune 500 companies, as she puts it, “interested in creating workplaces where women thrive.”

It’s also why – with companies like Airbnb, Udemy, Visa and Gap, Flynn has launched The Silicon Valley Longevity Project, which seeks to bring together companies recognizing that “How companies prepare for and respond to changing workplace demographics will have a profound influence on their ability to compete in the global marketplace and will affect the communities in which they operate.”


More background: Flynn previously served as Chief Marketing Officer of GSVlabs, a marketing executive at Electronic Arts, and an associate consultant at The Boston Consulting Group. Like many professional women, she also left the workforce for a period to raise her family.

So what can and should companies do? And what lessons can be learned from executives and firms who have succeeded – and from those who have failed?


Transcript: Diane Flynn, How Companies Should Respond to Changing Workplace Demographics

Chris Riback: Diane, thanks for joining me. I appreciate your time.

Diane Flynn: You’re welcome. Delighted to be here.

Chris Riback: A conversation with you I think should start with the big picture. As we come to the end of the second decade of the millennium, in other words, the end of 2019, how would you characterize the state of the playing field for women in the workplace?

Diane Flynn: That is a great question, Chris and I have mixed emotions on it. I think on the one hand there are a lot of positives for women that have evolved, especially in recent years. I think there’s been women using their voice much more than they used to. I think some atrocities of the past have come to light, which is a great thing for women.

A lot of companies that we work with are initiating support mechanisms and through mentorship and in women’s employee resource groups, and executive coaching, and all kinds of interventions to really support women which are needed. Taking unconscious bias out of the hiring process to the extent that they can has been helpful.

However, I temper that with the fact that a recent study said that 60% of men now as opposed to 40% about three years ago are afraid to mentor women. And I think that’s doing women a huge  disservice, and men, because men are then not benefiting from the voice of women. And we know from a lot of the great studies done by BCG and McKinsey and Deloitte that women on your team contribute to the bottom line.

And so to the extent that companies can really maximize the voices of all diverse groups, they benefit. And so when men are afraid to mentor women or support women in some ways because of what they might be accused of, or who knows what’s holding them back, it hurts everybody.

Diane Flynn: So that’s why I say I think there’s been a lot of positive traction, and I think there’s been some steps backward at the same time.

Chris Riback: And in addition to that, I don’t know if that would be called a cultural component, but I’m also interested in the numeric component. And so often success or progress in the workplace is measured in pay and in the pay gap. And that may not be fair and that may not be the only metric, but let’s talk a bit because you just described one that’s certainly not moving in a totally constructive direction.

But talk to me about the pay aspect because in the end that’s highly measurable. And PayScale ran a study or a survey and released its State Of The Gender Pay Gap for 2019. I was interested in what they differentiated as the uncontrolled gender pay gap versus the controlled gender pay gap, and I need to explain what I mean.

On the uncontrolled gender pay gap, which takes the ratio of median earnings of all women to men, so all the women working versus all the men that are working, and there  are survey showed that women still make only 79% of every dollar that men make in in 2019. I’ve seen stats like that, I’m sure you have as well, you see those stats around 80% that type of thing.

A lot of companies that we work with are initiating support mechanisms and through mentorship and in women’s employee resource groups, and executive coaching, and all kinds of interventions to really support women which are needed. Taking unconscious bias out of the hiring process to the extent that they can has been helpful.

And they say that uncontrolled wage gap represents the… That women are less likely to hold high level high paying jobs than men, and there are structural barriers which keep women from advancing in the workplace. And they call that the opportunity gap.

They then looked at something and took survey data on the controlled gender pay gap, which controls for a number of factors such as job title, years of experience, industry and location, and the only differentiation if they’re running their survey correctly between workers is their gender.

And on that, so same job, different gender, same I guess in a sense same everything, different gender. They claim that women now make 98 cents for every dollar that an equivalent man makes. So two questions out of that extensive preamble. One on that opportunity gap, on that 80%, on that women being less likely to hold high level, high paying jobs than men. Why can that not close?

We all have been hearing about that for so long. Why does that remain in your experience so vast? And then two, from your experience, do you buy the other part, same job, everything controlled, woman versus man, do you buy that it’s 98 cents out of every dollar that women are making, 98% or does that seem over stated based on your experience?

Diane Flynn: Well, it’s a great question, and I think to level-set, I think it’s important to acknowledge that there is a spectrum of companies out there. And the way I think of them is they moved from the, let’s call it less than lightened companies on the spectrum where I think… We see it all the time and you read about it in the news.

There are bro cultures, there are cultures that really do not support women, and I think that in some of those you’re going to see huge pay gaps and huge inequities of women advancing.

To the other end of the spectrum, which I call the highly evolved companies or highly enlightened companies, and I was just reading a great article about Slack being one of them where they have not only a much higher percent of women in the company but women in management, women in technical roles and it has translated to the bottom line. So I think it’s important to differentiate those.

As far as why women aren’t, to your first question about the uncontrolled pay gap, BCG has a really interesting study that they looked at thousands of companies globally and they found that when you look at the pipeline of employees, women are starting slightly higher than men.

Diane Flynn, Co-Founder and CEO of ReBoot Accel, explains how high-growth and Fortune 500 companies, as she puts it, can create “workplaces where women thrive” -- and how to help accelerate the careers of women in the workplace.
Diane Flynn, Co-Founder and CEO of ReBoot Accel, explains how high-growth and Fortune 500 companies, as she puts it, can create “workplaces where women thrive” — and how to help accelerate the careers of women in the workplace.

There’s more than 50% in the very entry level, and we know that from looking at college graduation rates that women are graduating at a higher rate than men, they are entering the workforce. So there really isn’t a problem at the entry level.

But what you see is once you get up to the managerial level and then the director, executive, CEO, a huge fall off going from 50% down to the CEOs in the 10 or less percent, and the work that we do at ReBoot Accel is really to address that, what happens to these women and why do they fall off?

And what we found is that there’s all kinds of reasons. I think there’s the sense that women still carry the bulk of domestic responsibility. It is changing. I’m seeing a lot more men making that choice to stay home, but historically women have and I think still continue to assume that role.

And so women are stopping out. I’m an example of that. I spent time at BCG, I spent a decade in Electronic Arts, and then I had two toddlers, and my husband was traveling all the time, and I made that choice. Women still make that choice more than men.

I think the great news is that I have daughters in their twenties now and they are going to have much different options than I had, because I had the all in or all out option. I think today we’re seeing lots of people are working remotely, they’re working part-time. My daughter’s traveling the world right now and she’s got a few contract jobs that she’s doing from coffee shops in Paris. I couldn’t do that when I stepped out. So I think that is going to help, but that’s kind of lifestyle choice that is being made.

I think what’s happening in a lot of these less enlightened companies is women don’t have the same resources that men have. A great example of that is informal networks. Fewer women golf as a very obvious example.My husband golfs, lots of his deals happen on the golf course. That’s not to say that that’s a bad thing, but it does suggest that unless women have access to those same kinds of informal networks, they’re going to miss out on opportunities.

In a lot of these companies, women can be the only people in the room, and so if they are not included in some of these informal networks, they don’t even know about opportunities either for advancement or mentorship. Mentorship is another big one. When we survey women, a lot of them have no mentors, and men often do. And even Forbes wrote a great article about the different kinds of mentoring that a lot of women receive than men. They call it pie and cake mentoring. And without getting into the weeds, basically men are getting mentoring that propels their careers.

It’s more around leadership and exposure to senior meetings, and understanding power, and all that. Women’s mentoring is often takes the form of encouragement and confidence building, and that’s not a bad thing, but it’s not exactly the type of mentoring that’s going to get them to the next level. There’s a whole number of other things. I think unconscious bias is huge in the advancement process. You often read that men are promoted based on potential and women are promoted based on proven experience. That kind of approach is going to favor men when it comes to advancement, and there’s been tons of unconscious bias research.

Even how job descriptions are written up, sometimes there’s more masculine verbiage in the job description that either favors men in the process or attracts more men to apply. We also know about the confidence gap or imposter syndrome that tends to impact women. Everyone knows the study that men will apply to a job if they meet 60% of the criteria, and women will often not apply unless they can tick every check box. That’s the kind of thing that hold women back.

And then finally, I just note that in the pay equity piece, women don’t tend to negotiate on their own behalf as much or as diligently as men. So women are great in research at negotiating for others. They are some of the best managers because they have your back. When it comes to negotiating for themselves, they don’t.

And so what we’re seeing is even companies that regularly do pay equity analysis, they might find at equity one year and then they’re out of sync two years later. And what we believe is happening is that the men continue to negotiate and the women don’t. So even if you get them at parody, they don’t negotiate and then they fall behind again. So that’s why we always encourage companies to do this kind of pay equity on a regular basis.

Chris Riback: So much there, and in the fact that goes to the heart of my first couple of questions about where are we today? Are you satisfied with where we are today? Why do various gaps still exist? And you’re describing just a multi-layered series of integrated challenges, some of which play off of each other and can exacerbate and make other situations even more complex. So-

Diane Flynn: Chris, can I add final one?

Chris Riback: Of course.

Diane Flynn: I just realized I didn’t address your second question about the. The demographic I work very closely with are women who’ve paused careers and now want to return to the workplace. I have yet in the five years I’ve been doing this, and the thousands of women we’ve helped relaunch careers, seeing any woman come anywhere close to the pay they were earning when they paused.

Chris Riback: Interesting.

Diane Flynn: And there is a huge sacrifice that I wish more women knew about that it’s great to stay home and take care of children, or caregiving needs maybe elderly parents, but it is important to understand that the kind of sacrifice that one makes from a pay standpoint. And I think it speaks to lots of things, but I think one of them is there is a discounted value for volunteer service. And one of the things we do with women going through our programs that we helped get connected and confident to return to work is we say, “Don’t discount what you did during your time off.”

Most of them held significant leadership positions as volunteers, and we say, “Just because you did not get a paycheck does not mean that you did not develop skills that are highly valuable to companies.” And so when we help them with resumes, and LinkedIn profiles, and interviewing, we really encourage them to package and reframe what they did as head of the PTA, or a working on a nonprofit, or whatever they did to say what were those skill sets that you kept actively engaged and even developed during your time off?

Most of them will tell you that because they had to juggle households, and kids, and lots of schedules, they became very efficient. They became very resourceful, they became very decisive. They have a great perspective on what really matters, and all of that is a critical thing that companies should be thinking about when they hire people because those are those soft skills that we keep hearing companies can’t find in people.

And I think a lot of these women who’ve paused careers and are now interested in returning bring those to the workplace in addition to the fact that they bring a lot of humility, and oftentimes they’re more about the team, and feeling engaged, and feeling purposeful, and driven than climbing the corporate ladder, which we often hear as great for the culture.

Chris Riback: Sometimes I wonder for the folks who aren’t able to find those capabilities that you just described, I’m frequently curious how hard are you looking?

Diane Flynn: Exactly.

Chris Riback: They might be there. In listening to you as well, it is striking me that what you do personally and what you do with ReBoot Accel is almost bifurcated and yet integrated. And what I mean is you seem to simultaneously be working with individuals, with women coming back into the workforce, and I’ve got some questions for you on that, and some of the stats that I’ve seen you talk about, about the number one, growing demographic in today’s workplace being women over 55, and I want to talk to you about that.

And you’re dealing on that level, and you seem to simultaneously be dealing with the C-suites at some of our most significant companies and corporations in terms of helping them consider culture, think about culture and maybe even evolve their cultures. You talked about enlightened versus not enlightened companies.

On that second point, and I’m sure that there are lessons from both aspects of what you do that drive your work and give you insights to be able to help both sides. On the part of working with the companies, does that type of enlightened culture, as you call it, does that start from the top? Is that a leadership question? And parallel to that, how do you guide women who don’t see that leadership at the top of their own companies?

Diane Flynn: What you’re asking is exactly the content of the book that my partner Patty White and I are writing right now, but it’s called “The Female Dividend,” and it is all about, this has to start at the top.

What we do is we dissect what do companies need to do to support women and advanced women in the workplace. And we argue that if it doesn’t come from the leader, it’s not going to work. And study after study has proved that out.

That being said, it’s not just the leader issue and it’s not just an HR issue. Yes, you need programs and policies to support women, you need one of the number one most demanded workplace attributes right now, not just from women but millennials and all parents, and caregivers is flexible work arrangements.

And so that is something we’re seeing very aggressively adopted here in Silicon Valley where I am, but you’re starting to see it all across the country, and there’s still some resistance, and we talk about how to overcome that resistance, but that’s an example of family leave is another one. If you don’t encourage men to take parental leave, then you are handicapping all women. So there’s lots of things that HR needs to be thinking about in terms of programs, but then we have a whole list of things that the women need to be doing, and to your question about what can a woman do where the leadership doesn’t embrace this.

They have to find their voice. They have to make sure that their voice is heard around the table because you’re not going to benefit from what we call The Female Dividend unless that voice is heard. And so we do a lot of workshops to empower women. We do a lot of executive coaching for women. And we think that-

Chris Riback: What about the woman who says… I could hear somebody listening to you right now and saying, I hear you sister, but that is easier said than done because you have not been inside my company. And the culture in my company is, if I speak… I agree I should speak up and I’m not shy about speaking up.

I can speak up about business issues, I can speak up about operations, or production lines, but if I want to speak up about culture and about fairness, that’s not going to go over so well, that’s not going to be heard. No one’s going to hear me on that.

Diane Flynn: So that’s why a lot of the research says, “You don’t benefit when you have one woman in the room.” You need, I think they say 20% is the bare minimum, and I think that’s partly why California has imposed new laws for public companies around women on boards.

There have to be enough underrepresented voices to amplify each other so that… That is definitely proven in research. It’s very hard to be a trailblazer if you’re the only voice around the room. At some point I would probably tell that woman if they’re just up against a wall that maybe that’s not the place that they are going to be most effective.

I hate saying that, but I also think it is the reality. There are companies that are just… they have a long way to go and one woman is probably not going to be the change that they need to see.

I think if you can get more women… One of the things we do when we work with companies, we’re working with one that has an entire senior leadership team, 14 people and they’re all men, and we made a very strong case that next time there are openings in at that level, they need to be thinking about how do you put women in there, one to capture their voice, but two, to create visible role models for the rest of the organization.

We spent half day with a number of the female leaders in a women’s summit and we heard many women say, “I don’t see a path for me. I don’t see a role model.” They basically said, “I am going to leave this company if I don’t see where I can grow.” And so that is a secondary reason aside from the importance of the diverse voice at the table is to show women in your organization that there are powers for them and that they are valued.

There’s a number of ways that women can help advocate. A lot of companies have heads of D&I, I’d say working closely with them. They’re usually very sensitive to the underrepresented groups in the company. Interestingly, when I go back to the evolved companies, companies like Slack consciously do not have ahead of diversity and inclusion because they say we don’t need it, it’s baked into our DNA.

And that’s the interesting thing. If you’re at the opposite end of the spectrum, you need somebody in that role I think to really advocate, but as you evolve, it should just be part of respecting each individual despite their gender, race, any of that, and that’s where I’d love our society to get to.

Chris Riback: How defensive do leaders get when you talk to them about this? If you identify, the company you just mentioned, 14 male leaders, I guess when they come to you, when you get to them, is it a self-selecting group? Is that because they want to make some change, and so they’re looking for some expertise and some guidance on how to make it?

Or is there a sense of defensiveness might be too strong and I’m sure you wouldn’t necessarily want to characterize any of your clients as having been defensive of course, but you know what I mean. Do you have to deal with that balance? Do you see that balance out there?

Diane Flynn: What we see is usually very enlightened leaders because they wouldn’t carve out the time and bring us in unless they cared. So I would say in this case, this was a group, I wouldn’t say everyone around the table was bought into gender diversity, but the important thing is the CEO was, the head of HR was, and so that’s why we got to the table.

I would add, we do some work with private equity, and CD&R is one of our clients, and I want to give them a shout out because I think they’re really very conscious of the importance of this and they’ve invested in us and invested in making this a priority.

Chris Riback: I want to make sure that we get a chance to talk as well about another really fascinating aspect that I have heard you talk about, which is the aging and multi-generational workplace. Earlier this summer you were on a panel discussion where you said you many things remarkable, one of which was, “The number one growing demographic in today’s workplace is women over 55.” That’s number one. “And the number of people over 55 is going to be 25% of our workforce in five years, and that’s up from 10%.”

So first, what’s the why? Why is that occurring? And secondly, what does this mean qualitatively for the workforce, workplace culture, and for opportunity for women? How does this aging and multi-generational workplace, how does it affect the things that you’ve been talking about?

Diane Flynn: So let me address the why first. And these are my, some research and some opinions, but when I see the women I work with who are over 55 reentering, about a quarter of them are going through a major life transition. Typically, that would be a divorce, for some it is… We have a number of widows that didn’t expect to be working.

We also have empty-nesters like myself as I commented earlier before we started the call, I’m so delighted that I am working because the house is empty. So there’s a lot of that. People at 55, I remember my mom at at 55 never would have contemplated going back to work. We’re living so much longer. My dad started a charter school at 85, chaired his last meeting at 87, and that’s the role model I grew up with is that as long as we have the mental and capacity to give back and do meaningful work, that is what I want to be doing.

And so if you look at, if I lived till 85 or 87 like my dad, I’m only halfway through my adult life. So that’s a lot of years to be doing something meaningful. We’re healthier, we’re more active, we’re more educated, we have more work experience than previous generations. So I think all of those reasons people want to go back to work.

The other thing you asked about the implication. We do a lot of retreats for women who want to resume careers. Almost every single one of them, and these are women in their 40s, 50s, 60s wants to have some kind of social impact. I’m truly amazed by how many of them are seeking purpose and meaning at this point in life. It’s that second mountain that David Brooks alludes to in his book that they really want to give back.

And whether it’s sustainability, the environment, mental health, building community, accommodating, caregivers, you name it. I think that the impact of bringing all these women into the workplace at older ages is going to have tremendous positive impact on our community at large. And that’s what I think truly gets me so excited about the work I do is I see these women going out and really making a difference and making money doing it. It’s a very empowering thing as well.

To your comment about the multi-generational workplace, we are doing an initiative here, so it’s starting in Silicon Valley, but we hope it spreads nationwide quickly. We’re calling it the Longevity Project, and we have companies like Visa, and Gap, and Airbnb, and Udemy, and others behind it as charter members, and what we’re really trying to do based on Chip Conley’s great book called Wisdom at Work where he talks about how five generations are now working side by side.

He was brought into Airbnb at 52 and worked with Brian Chesky who was in his 30s at the time, and realized that you have to combine because he says, “Fresh eyes with wise eyes.” And all the experience that these older people bring is a great compliment to the digital natives who have lots of energy and ideas, but perhaps not the same degree of wisdom that some of us who’ve made a lot of mistakes and learn through the years have have garnered.

And so that’s, I think the beauty of these, we call it age friendly workplaces where you can take this mix and through mutual mentorship programs, and lots of different ways to really help each individual bring their best self to work. So that’s the goal of our project.

Chris Riback: But Diane, you understand that millennials don’t plan on making mistakes, so learning from those of us who have made them, it seems a waste of energy.

Diane Flynn: Yes. There’s a great quote that… God, I’m trying to get it right.”Good judgment comes from experience, and experience comes from a lot of bad judgment.” Something like that.

Chris Riback: Yes, that sounds right.

Diane Flynn: You have to make all the mistakes to finally get to the wisdom, but no one ever sees that at the front end.

Chris Riback: It must explain why I feel so wise and so experienced. Tell me, on a practical level. Chung a little bit in cheek but not fully, very practically. Can we all get along? Are you seeing and do companies see tangible benefits from the multi-generational workforce, from the integration of newer workers and more experienced workers?

Diane Flynn: Absolutely. I’ll give you one example that Chip likes to tell. Again, Chip Conley who joined Airbnb, one of his first meetings he talks about the young developers wanted to develop Airbnb as an app used accessible by a phone. Chip made the point that a lot of the, at least, I don’t know, Chip made the point, but Chip suggested that some of the older people Airbnb mentioned is that because a lot of their hosts are over 50, they are not as comfortable using phone first as a platform for booking and doing their Airbnb.

And not only that, but after 50 your eyesight isn’t quite as clear, and so because of that recognition, Airbnb then adopted a web based platform, and it’s just one small example where if everyone is in their 20s or early 30s, you may not think about the perspective of somebody like that. Chip also at Airbnb found two of the, I guess super hosts who had hosted the most Airbnb nights, and they were a man and woman in their 60s and 70s I think, and brought them in for a three month internship so that everyone in the company could learn from their experience and-

Chris Riback: Great idea.

Diane Flynn: … from their wisdom. Yes. And Pfizer likewise, several years ago brought in sort of based on that movie, The Intern, or the 70 year old intern, brought in a gentleman who was in his 70s and I actually saw him on a panel at South by Southwest with an intern who was I think 24 or 20, no, I guess she was in college, so maybe 22, and they each talked about what they learned from each other.

And she said from him, she learned about gravitas, about standing up, about eye contact, shaking hands. He would take them out to lunch and share his wisdom. From them he learned about social media, and digital marketing, and all these new approaches that he wasn’t familiar with.

So those are a couple of examples where I think that what we really need is we need to all be good listeners, and we all need to be curious. And I think judging each other is the worst thing we can do, and to ever say, all millennials are X or all older people lack energy or any of those things is a disservice. And I think to the extent that we can approach every conversation as an opportunity to learn, that’s how we’re all going to benefit.

Chris Riback: Diane, thank you. Thank you for your time and for your insights that really… It’s very clear why these are relevant at all ends of the employment spectrum age-wise, but also where one sits within an organization and a across the genders. There’s a lot there, and thank you. Thank you for sharing it.

Diane Flynn: Thank you for having me. I really appreciate it.

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