Mitch Shepard is the founder and creative force behind WiRL leadership Series, which is the first program of its kind that develops rising star mid-level women and ensures that the entire ecosystem at any given company is ripe for women to thrive and advance. We had a chance to chat with Mitch about the challenges facing women who are aiming for senior-level positions, and also learned ways that companies can help improve gender diversity in their boardrooms.

Why did you Decide to Focus Your Career on the Development of Women Leaders?

I did not initially set out to focus only on women. It evolved that way for a couple reasons. I spent the first part of my career working in a wilderness setting, where I was guiding wilderness expeditions for executive teams and all sorts of other kinds of groups. And I was often the only woman in a position of power or authority. So I know full well what it felt like to be in an environment and be the only female – the token female, as we used to say in those days. And then when I made the transition into leadership development, coaching, and consulting, I ended up working yet again with almost all men, because I was coaching executive leaders primarily in high-tech at the time. And what I noticed was very few women in leadership roles, and when women were in leadership roles, there was often this tone in the room of, “One of these things is not like the other.”

And I saw women being unintentionally, but frequently, marginalized – like the voice of the woman in the room or the couple women in the room being marginalized. And I saw this kind of groupthink happening where the eight or ten men in the room might be all heading in the same direction from point A to point B, and the women are coming in with a different perspective, worldview, or way of communicating, and often being kind of pushed aside – again, unintentionally. So at some point, I thought, “I have got to be part of the solution. There are definitely some very clear gender divides going on – how can I help? How can I help my clients navigate this?” And that’s when I started turning my focus away from just general leadership coaching and toward being a gender in leadership specialist.

The Topic of Having More Women in Boardroom Positions can Often Become Politically-Charged

How do you eliminate the tension that can accompany these discussions?

What I’ve found when I’ve gone in and I’ve worked with clients around this is that when the conversation is approached only from a numbers perspective, sounding something like some members of a board or executive leadership team saying, “Hey! We really need to think about diversity, we really need more women/people of color/age/generational diversity on our board,” you get the pushback of “Well, why? We need to just choose the most qualified candidate.” And it starts to sound like reverse discrimination. But when you put the data in front of a board, it becomes less politically charged and more a strategic business conversation.

There are masses of data out now from Gallup, Harvard Business Review, Pew Research, etc. and much of this data points to companies that have a critical mass of women at the top have 16% higher return on sales, 23% higher return on equity, less risk of lawsuits, healthier culture, less turnover, and overall better financial performance. So when you turn it into, “Hey! We stand to be 15-16% more profitable if we can get this many women on our board or in our executive leadership team,” then it becomes a question just like if there was a product opportunity that had the potential to increase your revenue or profit by 15%, you would absolutely be talking about that as a strategic business imperative, as opposed to “Well, that’s not fair! That’s reverse discrimination!” So I think part of this myth is that I think too many companies approach it from, “Well, socially, it’s just the nice thing to do. This is the right thing to do.” Well, yes it is. But it’s also a business imperative.

Can you Tell us About Some Myths Regarding why Women Aren’t Being Promoted Into Senior Management Positions?

There’s a lot of myths circulating around, one of which is that there aren’t enough women who want the positions – which isn’t true. One is if we promote women, will they just leave when they start having kids? And actually, the research counters that as well. The LeanIn and McKinsey report entitled “Women in the Workplace” showed that women who are mothers in executive positions are actually less likely to leave their executive roles than a man.

I think some other common myths are the fundamental way that women lead, that the people at the top who are making the decisions about who should join any given leadership team or board tend to be influenced by their own definition of what a great leader looks like. And because the business world was essentially formulated by men a couple hundred years ago – business cultures did not have many women in them – it’s pretty obvious that it was built on a male way of thinking, leading, valuing, and noticing.

And so women come into the work world and often feel, “Oh! I see. I can get into a leadership position, but I definitely need to fit in. I need to lead like they lead. So I need to be confident, decisive, competitive to a degree, more linear and directional in my thinking as opposed to thinking of all of the variables and factors.” And so oftentimes, managers might ask, “Does she have the chops to lead?” But what that question really is about is “Does she have the chops to lead like me in my male way of leading?” So women are often not given the opportunity because they don’t look like, think like, act like their male counterparts. So that’s part of the bias – unconsciously, unintentionally – that can happen.

In Your Experience, is There any Evidence of Men and Women Being Judged by a Different Yardstick When it Comes Time to Promote Employees to Managerial or Boardroom Positions?

A common dynamic is that women are often walking this tightrope – often referred to as the double-bind – where if you’re assertive, confident, sure of yourself, vocal, and convicted, you can be seen as aggressive or a bitch. Studies have been done where they look for specific words like “aggressive” in performance reviews, and the incidence of that word showing up in women’s performance reviews is significantly higher than men’s. So again, women live within a smaller set of boundaries, and what they’re often told is, “You’re not quite ready for that role because you need to continue to smooth off this edge, become more palatable, become a better communicator, be less emotional or less aggressive.” So women feel scarred from that. Women feel pissed about that – as they should. And men often don’t notice that they are holding them to a different standard.

Are There any Obstacles That Women Themselves are Creating That Effectively Hinder Their Path to the Boardroom?

Yes, there are. One of the things that’s kind of well-documented through the research is that men are 46% more likely than women to have a sponsor – in other words, someone who is in their corner of the ring, advocating on their behalf, someone with influence and power who is opening doors for them. And women typically are really good at getting the work done and expecting the right promotion or the right thing to happen. They kind of trust the system; they almost overtrust the system. And they don’t ask actively enough for those people who can open doors for them to open doors.

The other piece that has been well-documented on this is this concept of confidence. Men are more likely to jump into a new position or role when they have 50%, 60%, 70% of the criteria met on a job description. Women are more likely to wait until they have 80%, 90%, 100% of the qualifications before they leap through that door. So this actually has dual responsibility. For the companies that want more women in positions of leadership and they see that mostly men are applying, they need to ask themselves the hard questions. Are there women who are equally or more competent for this role? And if they aren’t coming into my office raising their hand for this job, how can I go proactively seek them out and encourage them? And then women need to have a level of understanding that they may need to jump into those opportunities before they have it all figured out, and have a level of awareness that men are doing this, and that they can jump in, too.

How do You go About Implementing the WiRL Program Within a Specific Company?

We’ll say, “Pick a set of people that are ‘must-keeps’ at the mid-level,” because the mid-level tends to be where women are most likely to off-ramp or get stuck at the glass ceiling or fall off that cliff in the middle. So we put those women in groups of ten to 12 per group, and we put them through a nine-month program that consists of some online learning combined with monthly group meetups professionally facilitated by someone on our team. And with the women, we work with these mid-level women on things like confidence, authenticity, leadership greatness, gender intelligence, emotional intelligence, strategic thinking, standing out, and keys to their success and advancement.

Then at the same time, it’s equally important that you get the entire ecosystem in the company aware that women will approach decisions, problem-solving, communicating, executive presence, and emotionality in very different ways than men. And you need all the people around them, the same people that are in charge of promoting, advancing, mentoring, and coaching them to understand that you do not want to inadvertently coach women to be more like men in order for them to reach the top. You want to coach women to bring more of their authentic selves and all of their natural strengths to the table.

So we work with the managers, mentors, and senior leaders – men and women, but senior to these mid-level women – on three things: the business case for women in leadership; the brain science behind gender differences – so we can ground some of these differences in data and show that men and women are equally competent as leaders, but they just approach leadership differently; and how to be extraordinary advocates, mentors, and managers to the women on their teams and the women in their life. Once a quarter over the course of a year, we meet with the men, the women, and the senior and the junior people all together to discuss what insights they’ve been pulling away from the program, how is it impacting their work world day to day, and what issues around gender intelligence most need to be addressed in order to have the healthiest culture for both men and women.

Can you Discuss Some Success Stories That You’ve Heard About From Companies Who Have Completed the WiRL Program?

For the companies that track things like vertical movement, lateral movement, or retention, some of those companies can see hard-line differences pre- and post-WiRL. But it takes a couple of years of watching those statistics to really see the impact of the program. More anecdotally speaking, the women will say that they have a greater understanding and confidence in their natural ways of leading and working, which translates to greater authenticity, greater fulfillment, and companies getting more of their engagement and talents in their business, which is really cool.

Also, women feel less alone. I think one of the biggest pieces of feedback we get is that women feel connected to other women, they feel validated, they feel empowered to do anything from speak up more to ask for that promotion or that raise to challenging the leaders of their company – like being “truth-tellers” instead of “nice girls.” One woman shared this story: “Before WiRL, I had noticed this technology that we’re using that was clunky and old, and we all knew that it would be a really significant investment to invest in this other technology that was better.”

“I was looking back through my notes, and I saw that a really important thing in having influence is to do your homework, crunch the numbers, make the business case, and paint the ROI.” “I had heard ‘no’ twice when I had suggested that we take on this new technology. So I went back and I did my homework. I researched what are we losing right now in productivity, in mistakes, in customer satisfaction ratings. What are we losing right now, and what are we going to gain with this new system? How much faster is it going to be, and how much happier are people going to be? At what point will we break even, and at what point will we come ahead in terms of cost savings?”

And she was able to paint that over the course of 18 months, the cost of it was significantly lower than the benefit received, and she was able to equate that into numbers. And she got a “yes.” She was not even going to go back to the table and pitch this again, but she was able to get the skills required to do it well, have the influence to get a ‘yes,’ and then as a result, the company saved a million-plus dollars. And they had invested a fraction of that to put 12 women through this program.

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