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S2 Ep3: Why Women Are Still Leaving - the systems holding them back with Penny De Valk

• Mary Gregory • Season 2 • Episode 3

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Part 2 of 2 episodes with Penny De Valk.

Why are organisations still losing talented women — and why does this pattern persist, even when leaders genuinely want things to change?

In this second episode of a two-part conversation, Mary Gregory and Penny De Valk move beyond individual leadership journeys to examine the systems shaping women’s experiences at work today.

Drawing on Penny’s global work with senior leaders — alongside insights from the McKinsey Women in the Workplace research — this episode explores why the leadership pipeline continues to leak, why women are still promoted and sponsored differently, and how well-intended organisational decisions can quietly disadvantage women.

Mary and Penny discuss the broken first rung, sponsorship versus mentorship, invisible and emotional labour, flexibility stigma, and the growing fatigue around gender equity efforts — as well as what actually helps organisations retain and develop female talent.

This is a grounded, realistic conversation about why women leaving is not a lack of ambition, but a rational response to systems that still haven’t caught up — and what leaders can do differently if they want to stop losing great people.

Free resource:
If this conversation has raised questions for you, you can download the Gender Equity Temperature Check — a short, reflective tool designed for HR, DEI and senior leaders to assess the what's really happening beneath the surface for gender equity in your organisation. 

Download your Gender Equity Temperature Check here: https://www.marygregory.com/gender-equity-temperature-check

Connect with Penny on LinkedIn: https://www.linkedin.com/in/pennydevalk/

Or visit her website: https://pennydevalk.com/


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✨ Produced by Mary Gregory Leadership Coaching

SPEAKER_00:

Hello and welcome to She Leads Collective Podcast. I'm Mary Gregory and I'm so glad you're here. This podcast is a space for honest conversations about what it really means to lead as a woman today and how we can all show up with more courage, care, and clarity. You'll hear from inspiring women, powerful allies, and bold truth tellers who are changing the game not by playing tougher but by leading smarter, softer, and stronger. Hello and welcome back to the She Leads Collective podcast. And today's episode is a follow-on from our episode of last week where I met with Penny DeVorc and she told me all about her incredible career leading at very senior levels in organizations, balancing that paradox between taking care and taking charge in leadership. And we also started to move in to look more deeply at some of the themes and trends that are coming through in organizational leadership across the globe and how that's impacting women and the pipeline. So today Penny is back with us, and I'm very pleased that she's back with us. And in this episode, we're going to go deeper. We're going to explore the systems that are going on beneath the surface, some of the pipeline issues that are under pressure, and what it's like as a senior woman leading in organisations today and the unintended consequences of organizational decisions and why gender equity still isn't done, despite there's a current trend recently saying, Oh, we've done enough, but it actually still isn't done, and that's certainly not many women's lived experiences in the workplace. We're also going to touch on the latest McKinsey Women in the Workplace research that came out at the end of 2025 because that gives us some important data to understand what might be happening. And it's evident this that is backed up by what Penny has experienced and what we're all seeing in how things are working day to day. So I hope in this conversation we'll be looking at how responsibility, realism, and we'll also be thinking about what generally makes a difference. Penny, thank you so much. Let's come back to you and thank you for being here again. I'm so grateful. It's a pleasure, Mary. In our last episode, we were just moving into thinking more about what it's like being a woman in the workplace today and some of the challenges that women have to face, and also what that means for organizations who are struggling to keep really healthy pipelines that include talented women. So from what you describe and what's been echoed in the McKinsey research, what do you think stands out most for you as the main challenge in today's world?

SPEAKER_01:

Oh, um, I think that there is no, and it's concerning to see it maybe getting worse. You know, we've been waiting for maybe evolution and generational change, that that leaking leadership pipeline that has women disproportionately falling out year after year would somehow get fixed. And it's stubbornly not. We still know, as you've seen in McKinsey, pretty much half and half at entry level. By the time they get to C suite, it's more like 23% women and men. And so this challenge of how do we keep talented women in the pipeline, both um is, and it's not just about. I think my concern is often, oh, well, you know, we need to take this remedial response. You know, obviously women aren't up to it, that's what I hear. They're not up to it, so we need to teach them how to negotiate and work on their executive presence and um give them confidence, all of those things that we see as lacking in women, um, or that they're not up for it, or because they all go and have babies, or you know, they just they they don't have that steely uh steel steeliness uh that comes with needing to be a leader. And so I see some organizations who still have this mythology around women are up to it or up for it, either responding in ways that are just not helpful, um, or um actually not responding at all, thinking, well, that's just the way it is. Women aren't really leadership material, they don't want to be, they're not ambitious. Really interesting. So I think the the intransigence, the stubborn nature of the leaking leadership pipeline, we know is much more nuanced than tokens and you know, pushing people through and giving them the odd sort of rah-rah session. It's much more subtle.

SPEAKER_00:

Much more subtle, it's much more systemic, isn't it? And needing to address the organizational system, not just that let's run a nice uh powerful presence course for women or whatever. It's much more than just that. And you know, what comes out in the report is how for 10 years now the first rung of the ladder has been broken, which has a huge impact. And and and why why is that first rung so so critical?

SPEAKER_01:

Well, it's really critical because it's the foundation of women's careers. Um, it's what fuels basically the pipeline to where people go. It's that first, you know, uh, can I do this? That women take to go, yes, I want to be a manager and a leader. I can see how I could be and stay true to myself and operate with integrity. So it's it's really important for the organizations because it's the pyramid. Um, and it's really important for for women. So that's a complex story as well. So there's an element of self-sense, yeah, for the women. It's like, uh, do I want to be that? But we also know the research shows us that still women are promoted on performance, not potential. So, and we know that confident women are not seen as the leadership potential that men are. So there's this nuanced piece of how do we perceive leadership capability and leadership potential. And it's definitely gendered by both men and women.

SPEAKER_00:

Uh, there's also, I think, linked to that, a need for sponsorship and advocacy. So women, women tend to get over-mentored and under-sponsored. So there's something about making sure that your women in the pipeline are getting as equal amount of sponsorship and advocacy as your men are.

SPEAKER_01:

And that women ask for it. Because I know, you know, in you will have done the same in my practice. Um, get a mentor. Everyone needs a mentor, even for women to go, oh, do I really? Yes, it's not just having a chat. And so women will often go with a development mindset. Men are much more naturally go with an advocacy mindset. And so to say, well, look, you know, there's something different here, a mentor that's talking about you, not just talking to you. Uh, and we know that mentors with the best of intentions find it risky to spend their political capital, which is what you're doing when you want a sponsor, someone to advocate for you. It's your reputation you're putting on the line. But they find it risky to spend their political capital on minorities. So it's so we've got to be savier about it. But we need sponsors and mentors and uh to go into that mentoring relationship thinking there is advocacy here. You've got to earn it. Uh, you know, you're not going to get that any anyway. But to be thinking that yes, I can learn from this person, but this person can can you know open doors for me, or an eye open the door, can be in the room with me. Uh, so really important to um, if you're not getting that level of advocacy, your visibility won't be as high. People won't even know necessarily that you want that next role. Whereas if you've got a mentor that says, you know, I think Mary is really ready for that.

SPEAKER_00:

Got to stop assuming that just because you're doing good work, you'll be seen. You've got to make sure you publicize that good work.

SPEAKER_01:

That that mindset, that first rung of, well, my work should speak for itself, is can be a really, really, a real break on your career. Because what you do is you end up working harder and harder and harder and getting more and more exhausted, and then wondering why your colleagues are getting uh progressing. So it's a it's a real shift, and it's not to say you're not doing good work, but what is the work when we get to that next level? Let's have a conversation about what that is. And yes, I know it's kind of scary to let go of some of your technical expertise because that gives us confidence to be in the room and start working on different things because this is an exhausting now-where.

SPEAKER_00:

Yes, absolutely. And of course, one of the risks is that, and this is what organizations are seeing happening, is that women start to leave the workplace because they are they're not their ambitions aren't necessarily satisfied, or they may think, what's the point in even trying to apply for a job or promotion here? Because it, you know, it just doesn't happen. So the risk is organizations are losing out massively on really talented women.

SPEAKER_01:

Really talented human beings, and that's you know, as we were speaking about earlier, there's not a CEO, CPO, COO, uh, you know, CMO. No one in the C-suite isn't really frustrated with the the calibre of the people and in the room and seeing their talented women uh leave. And so, you know, we have to, we do assume, need to assume good intent. They want to draw the talent through, but aren't necessarily um knowing how to do that.

SPEAKER_00:

Yes. And I think the other thing that I'm I'm thinking of as we're as we're discussing this, is that the load, they talk about the invisible load that women carry, and that's not just within the workplace. I mean, and often, you know, what I've seen in in research is that women carry the pastoral care of the organization that absolutely contributes to a positive, high-performing culture, but often is it completely invisible and doesn't get any recognition? But there's also the workload outside of the organization that women tend to carry as well. So, how can we as a society, as a as a organization, as a community, support the shift in that so that it the balance is is fairer?

SPEAKER_01:

Yeah, and I guess that goes back to the fundamental root cause, what we've talked about before is that tension between agency and communion, community. You know, men take charge, women take care. So even though we're in a leadership role, we're expected to bring communal expectation. So women are expected to volunteer for more things. Um, and if they're not, they're penalized, whereas men aren't. Um, so even in the even in the workplace, the extra work we're doing to do both is um is challenging. And it's challenging. How do we navigate that paradox? And it is a dilemma. Um, but we can do that. Be careful what you volunteer for, because sometimes it's our own instinct to go, yes, yes, I'll yes, I'll take the minutes. No, I won't take the minutes, or I'll organize the next social function for blah blah. Um, you know, I'll I'll organize this and so be careful what you volunteer for because you only have so much energy. And maybe be more strategic. Are you being strategic about what you don't want to? Of course, you have want to be a good citizen, uh, but be careful about what you volunteer for. Maybe you're volunteering for something that maybe has a little bit of visibility by someone you'd love to be your sponsor. Or that actually is not just invisible work. So, you know, constantly thinking, am I the lifeboat or am I the lighthouse? Am I the lifeboat or am I the lighthouse? And just we can be both sometimes, but it depends on what the situation needs, not to be on autopilot.

SPEAKER_00:

What do you think about organizations opening? I mean, because the challenge of culture is it's so invisible that we're not conscious of it. So there's something about having to build some consciousness around that. So, you know, the organization as a whole, from the board downwards, looking at what are the assumptions we make about our men and about our women or the different genders that we have here at work, what are the assumptions that we make and how can we shift them so they're more neutral?

SPEAKER_01:

Um, so many organizations have done fantastic work about just their processes, you know, just their recruitment processes, their progression processes, the nine-box model, trying to take gender as much as they can out of it. So it's not, you know, it's not those auto autopilots because it is subtle and it comes from us being in the in the middle of what was in terms of what leadership looks like and what will be. So we need to be as skillful as possible and we need to raise the the sort of the cultural nuance above the waterline. Without it, if it looks reprimanding, blaming, you're wrong, I'm right, then that will shut down learning. And so people will then go, and we've seen a lot of that. Uh, I think that's a lot of the anti-DEI move. People become defensive. Oh, I'm wrong. Well, no, this is not about being wrong. This is about being part of an evolution and reminding people about why we're doing this. This is about talent, it's not just about being nice to the girls who can't cope, and I've heard that before, or that progression of women will come at the expense of men. And all of the data shows that's not true. You know, and it gets back to the the piece that came out that was you know as disconcerting of the McKinsey research last year, but was that women are less ambitious. So I saw all of it, you know, headlines women are less ambitious than men. And you know, we know ambition is nurtured, it's not a tray, it is nurtured. We nurture it in our children, we nurture it in our teams, we nurture it in ourselves, and women's ambition when organizations really focus on gender equity as a core theme and a core expectation, uh, ambition in both men and women rises. It doesn't come at the cost of men. So I think being really sophisticated about how you have the conversations in the C-suite, how all of your HR and CPO HRDs are having that conversation more broadly, and then having them integrated into programs that are about around talent management.

SPEAKER_00:

And really understanding different genders' needs as well. But uh it's not even different genders, it's just different peoples. I think it's a real embracing diversity because it is actually a real strength of any organization, but it has to come from starting to really understand each other better.

SPEAKER_01:

It does, understanding one another better, and you know, because no one's doing the business case anymore. Everyone's done the business case for you know the quality of decision making, everything from ROI, top lines, eBit Dove, we all know the business case for a greater diversity at all levels of management, is compelling. Um so we've got to go, oh yeah, well, we know it's good, but we've sort of lost interest and it's all too hard.

SPEAKER_00:

So moving on to another area then, Penny, and that is that you know, post-lockdown, we've were introduced to all sorts of flexible ways of working, which on the one hand, because women do carry the majority of the of the mental load still, served women because they can work more from home and be more available for doing whatever they need to do to support the family as well. So something that has come through in the McKinsey report is how now the trend is more towards working within the organizational offices and being back in the office and less time uh working from home, which again is potentially penalising women. How do you think that's showing up in real organizations and what's the long-term impact of that ultimately?

SPEAKER_01:

Very interesting, isn't it? So, and talk about pendulum swing. So instead of the pandemic demonstrating to people that actually you've still got good decision making, it's sort of like, oh, let's get everyone back into the office. And I know women who were working part-time or virtually for 10 years before the pandemic, who are now being told that they need to go into the office. And you know, these are managing directors and VPs of so you know, the pendulum swing is is being wild, and it will penalize women who are by far the majority of uh people who work flexibly. So, again, it's just going and having grown-up conversations about, you know, again, the business case, not from a perspective of accommodating women with children, because as soon as that's the point of flexible working, that role will and that performance will be diminished. Or I think it's more than accommodating women with children, because we do know if flexible working is positioned as that in the organization, um, women really struggle to have a management and leadership career that's taken seriously. But what's in it for the organization? What is in it for the organization? And again, every organization I talk to is struggling to get talent. So, you know, having that conversation with this is how I work, you know, it's not about accommodating me. And for us to do the work around what does this give you? And when we are high-performing people, we've got more leverage than we think. So these huge mandates that put all we want everyone back at work. It's an old-fashioned reaction. What will happen, and we are seeing it, I've certainly seen it in North America, and even in times of people feeling really anxious around job security, they're being picked up by the really talented women who are uh, you know, just say, Well, you know, I work uh four days a week uh or I work virtually because you know I head up a sales organization. I'm all over in every state uh over the next few months. Why do you want me to come into the office? What is happening here? So um I think it's a great opportunity for organizations who haven't gone full swing back, who say flexible working is really important for everybody, and there's a balance, and I understand that everyone working from home constantly is it will have a cost, but there's a there's a really hybrid flow of people, and organizations need to be going, what will bring people into the office?

SPEAKER_00:

That's right, yes. What is the culture like that people want to come here?

SPEAKER_01:

And not just to play ping pong and have fun and get free food, but you know, what am I learning? Because there is, I do believe that a lot of leadership development is that sitting with Nellie. What am I observing? We're saying to learn, we pay attention. Who does that? What is that? What might you be able to try yourself and if. We're just seeing people on our laptops, it's not the same as seeing someone walking to the floor in a meeting, presenting, taking you know, you're just noticing that all the time. So I do believe hybrid models at every level are really important.

SPEAKER_00:

And yeah, and it's about you know making performance much more outcome focused, you know. So it's you're here to achieve this outcome. How you go about doing that, we can be flexible around rather than you've got to be in the office every day. And you know, I remember working for one organization who had a long hours culture. They, you know, everyone stayed late into the evening. It seemed to be to be the most effective person here, you had to work late. I once stayed late to see what went on, and people were doing their online shopping and stuff. It's like actually that people are complying to the norm of this organization that you work late, but it doesn't mean the performance is going to improve. Exactly.

SPEAKER_01:

Yeah, somehow they are sick, they think it's a it's a commitment signal. Somehow my you know, hours are demonstrating my commitment uh and my competence, and we know that's a very, very, very blunt instrument to demonstrate.

SPEAKER_00:

Yeah, very, very much so. Okay, so we've talked about some quite gritty challenges that are going on when it comes to DEI at the moment, and particularly some of the things that are coming through the McKinsey um report. But I'd like to explore in the sort of final part of our conversation today, what actually works when it comes to supporting diversity and inclusivity at the workplace and creating workplaces where everyone can thrive. So, what are some of the things you've noticed work?

SPEAKER_01:

Wow, that's big. And you know, as you know, my sort of specialism is gender diversity and women's leadership. That's the sweet spot. That's where I think that if we can get some traction in that area, we'll see it'll have a floodgate, and it does have a floodgate effect. What I've seen work are programs that are not about compliance, uh that that are not uh finger wavy, that are grown-up conversations in that start of the C-suite. And I think that's really important. Uh, what I do know works, and I know this is your my um playhouse completely, is wheelhouse, is the um is women's leadership development with a specific view of how do we manage this double bind when we are we are we are have competing expectations. And everyone will have, you know, there's women who will know that from the get-go. And those first line, that first level women who go, Oh, someone says you really need to work on your executive presence. And then the next week, you need to tone it down a bit. Okay, you need to come on, speak up at these meetings. Then the next week it's like, oh, you kind of dominated that meaning. It's like, okay, you know, that whole notion of when it comes to leadership, what works for men doesn't necessarily work for women. I didn't get taught that at business school. And it's not about contorting yourself to fit, it's not about fitting yourself into a system, it's not about fixing you, it's about being skillful while we are in between what was and what will be, because we are the bridge generations, Mary. As skillful as we can be, and it's and we are kind of pioneers. Uh we are at the frontier. As I said, you know, our grandmothers wouldn't have believed where we could have got to, and our goddaughters daughters hopefully won't be experiencing what we are. So it just behoves us to be skillful. So how do we how do we exercise our authority, build our reputation, influence, and demonstrate our expertise? With both and in our mind, we can do this with assertiveness and we can do it with warmth. So it's and it's just good leadership development. It's just great leadership development. It's not women's leadership development, but the reality is really helpful. And I've also very, you know, uh just annoyed, I suppose. People go, oh, we don't need women's only leadership development. This is a dilemma that our male colleagues do not experience. They do not just uh it's a persistent, uh stubborn stereotype that is projects onto by men and women, onto how women's leadership is experienced, identical leadership behaviors, but experienced differently because of gender. And that's all we're here to do as leaders is how am I being experienced? What is the wake I leave? And so, as women, we need to be really intentional about it, and that's okay. We can learn how to do that because uh we can be masters at paradox because I absolutely believe it is a leadership skill of the future. We need people who can solve for competing demands, and women leaders have been doing it from the get-go. But what works is not turning the light on, so showing in the room, rather than have all these women crashing around in the furniture in the dark because the room is not designed for them. Turn the light on. Oh, okay. So, how do we navigate for this? Um, and why do we do it? How do we manage the discomfort of being Frontiers women, being pioneers? How do we become skillful? How do we manage our own resilience in this marathon that is our leadership career? So we know that good women's leadership development works, we know C-suite experience that isn't admonishing or blaming or triggering defensiveness. Um they work, yeah.

SPEAKER_00:

And I really get that, and I love that analogy of turning the light on and not running, not bumping into the furniture because it's not built for us. I think that's a really great analogy, but also just to sum up, that starting at executive level, really getting that awareness in a very co-creative way, I think, is what I'm hearing, and then that linking very much to sponsorship as well. That when there's that when that's awareness at executive level, there's much more ability to be an effective sponsor.

SPEAKER_01:

And then, yeah, they can see it as well. And um I think that mindset of the double bind, as tiresome as it is and as persistent as it is, is the training, not the trap. And that's great leadership training. And we know, you know, we know we can we can do that, and getting exposed to that early is important and not for remote.

SPEAKER_00:

It's integrated, it's integrated into what goes on within the business, within the work, and that line managers know how to offer opportunities and support career development, all those. So line managers need the training too.

SPEAKER_01:

Yeah, absolutely. Just to be a bit more aware what they are bringing to um yeah, bringing to their decisions and judgments about uh what good looks like as a leader.

SPEAKER_00:

And what I hear then is it's a real cohesive um approach. It's not just one thing that fixes it all, it's actually taking the system on and taking that really cohesive approach, starting with the executive and then finding different approaches within the organization, but absolutely giving women their own space to thrive, actually.

SPEAKER_01:

Yeah, and you know, the point is you just said, Mary, about the systemic change, because it's a bit like if we extend the metaphor of crashing around in the furniture in the dark. People go, oh, well, it's you know, if you do women's leadership development, you're just fixing the women, and and what we need to do is fix the system. What will fix what will change the system is more is we normalizing women in leadership and helping women navigate. And the difference between, you know, teaching you to go around the furniture, oh, I see what's happening, as opposed to crash into it, and just saying we're going to change a system is like asking all the girls to go and stand out in the parking lot for 10 years while the system changes. What will change is us staying in the system, building role models that people can relate to. And yes, it's hard work, but no one ever said we work hard anyway, so we might as well be working hard on the right stuff. And it's important work because we are the bridge generations, and you know, it's not easy at the frontier, but we can learn the skills. No one's out there on their own. You know, there are so when it gets wobbly and you think I don't know how to walk on this tightrope. There's so many hands out there to help people.

SPEAKER_00:

There are, there are so many hands, and I love that it is absolutely us all coming together. It's not down to one individual or to one gender. We've all got to come together to solve this, really. Lovely, lovely, lovely. Penny, thank you so much. There's been so much that um we've discussed about some tricky questions that are going on at the moment, but also it's so good to finish on such a high with so many positive solutions for how we can address this. How can people connect with you?

SPEAKER_01:

Oh, pennydevolk.com. It's got my email, penny at pennydevolk. Uh, that's my website and my email address. So, and I'm on LinkedIn. So uh people have got an experience they want to share um and uh and a response because there's no doubt, Mary, some of the work we do is provocative. I don't mind being provocative, but some of it is like getting out of some of our old paradigms and you know, fueling that is my interest, is fueling women's leadership careers if they want one. If women aren't ambitious, um, you know, I I find that, you know, let's that's fine. You don't have to want to be a leader. And, you know, we're all going to be working into our 80s. You might just want to do a pause and go off and have a sabbatical and write a book in Tuscany or something for a year. And these days that doesn't necessarily mean with longevity as it runs in our careers. So I am deeply realistic about the data, and I am an eternal optimist. Uh, you know, I can be a realist about what the situation is, and I'm a deep optimist about what we can actually do about it. I absolutely believe both of us.

SPEAKER_00:

Fantastic. And I will say to our listeners, if anything has touched you from the conversations, either in the last episode or this episode that we've been discussing, and particularly what Penny's been saying there, please do get in touch. We do love to hear your comments. And this is a fantastic conversation that we do need to keep going. Thank you so much, Penny.

SPEAKER_01:

Mary, it's been a real pleasure. Thanks for taking the time.

SPEAKER_00:

Oh, my pleasure too. Thank you so much for listening to the She Leads Collective podcast. If this episode resonated with you, follow the show or share it with a friend and leave a quick review below. Or leave us a comment. Change happens through conversation, so let's keep this one going. Listen out for the next episode and join me as we keep lifting the lid on the stories that matter. Take care and keep leading with heart.

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