#38 – Closing the Gap: How to Accelerate Women’s Path to Top Leadership Roles | Empowerment & Career Advice

[00:00:00] Loree Philip: Hi, and welcome to the Daring to Leap podcast. I'm your host, Loree Philip. I'm so excited to dive into this week's episode with you. How can we achieve gender equity for women in top leadership positions? This week, we're diving into this important topic with our special guest, Kristina Cleary.

[00:00:21] Loree Philip: Kristina, a former chief marketing officer, believes that waiting 200 years for gender equity is simply unacceptable in today's world. So what can we do to speed up the process? That is the focus of this episode as we explore both top down and bottoms up approaches to support and accelerate women's path to the top.

[00:00:43] Loree Philip: Let's dive in. Kristina Cleary is the founder and chief leadership coach of Excel. Inc, where she is laser focused on helping women accelerate their success.

[00:00:56] Loree Philip: Her previous position was chief marketing officer at Ceridian, [00:01:00] where she led the global marketing organization, culminating in an IPO on the New York and Toronto stock exchanges. As the founder of Excel, she creates products and services to help increase the number of women in senior leadership positions by accelerating their personal and professional journeys through a unique mix of content, collaboration, and coaching.

[00:01:24] Loree Philip: Welcome to the podcast, Kristina.

[00:01:28] Kristina Cleary: Thanks for having me, Loree. I am so excited to be here. It's my pleasure to join you and I'm still looking forward to today's discussion. I

[00:01:37] Loree Philip: am too, and I thank you for your time, and I'm so excited about diving in on this and hearing a bit about your journey.

[00:01:46] Loree Philip: You had in your bio, your, one of your big positions was CMO. And as we talk about gender equality at the top later on in this [00:02:00] conversation you were moving up the ranks for sure. And what was it for you that made you decide, you know what, I really, I want to shift into doing, creating my own thing to starting my own business.

[00:02:15] Kristina Cleary: Yeah, so it's an interesting story, and I'm sure a lot of your audience probably had similar thoughts to I did. So you spend a lot of your time and a lot of your career in your, in your twenties, in your thirties working hard plugging away. And I know a lot of women who are highly driven.

[00:02:36] Kristina Cleary: Often think about maybe I want to start my own business. Maybe I want to do something on the side. And I truly believe that you can have an entrepreneurial spirit and be very successful in a large organization, midsize and small organization. But you can also be very successful on your own. It just depends on what is the right time for you and if [00:03:00] that's the right path for you.

[00:03:01] Kristina Cleary: For me, I had always thought about ideas along the way in my journey of if I were to start a business, what would I do? Would it be in technology? Would it be in services? And it all culminated for me in 2018 when I had been working for already over 20 years. And I had spent a lot of time traveling, I had spent a lot of time working very long hours.

[00:03:26] Kristina Cleary: And I thought that it was the right time for me to go out on my own and to experience something new. So I actually, I didn't go out and leave my corporate position with the goal that I was going to start my own company. I left my position at the time with the intention of taking a sabbatical and taking some time off to check off some bucket list items, et cetera.

[00:03:46] Kristina Cleary: So I went and learned how to play hockey, learned how to ride a horse. But during that time I networked a lot. I met with a lot of people and I had always loved my positions of leadership and working with [00:04:00] people and coaching other people. So that's when I did get my coaching certification because I also have a deep love of learning.

[00:04:07] Kristina Cleary: And just ended up starting my business by having people reach out to me, finding out what I was doing and started coaching my network, which led to me founding this business, which is specifically focused on women and supporting their journeys. And I'm absolutely loving every minute of it so far.

[00:04:24] Loree Philip: That's amazing. I think People sometimes misunderstand or just see kind of the end result of somebody's journey and assume that they knew exactly what they wanted to do when they switched paths. And in a lot of the cases, it's so interesting to hear various perspectives on this because a lot of the people I talked to didn't know what they were gonna wouldn't have been able to look into a crystal ball and see it exactly the way that it turned out.

[00:04:57] Loree Philip: But there was something there that was [00:05:00] drawing them to make a

[00:05:00] Kristina Cleary: change. Absolutely. And I think that that change could be leaving a corporate position and becoming an entrepreneur. The change could be leaving an existing very comfortable position for a promotion. It could be changing companies.

[00:05:17] Kristina Cleary: And I love to talk to my clients about what I see as windows of opportunities. And that you never know when the window of opportunity is going to present itself, but how you react to that window can change the course of your life, can change your career trajectory, it could be a conversation with a new person, it could be simply a connection on LinkedIn, etc.

[00:05:38] Kristina Cleary: So it's these windows of opportunities that we're faced with every day that you really have to be intentional about some of them. And how you react to them could potentially change your trajectory forever.

[00:05:50] Loree Philip: This is so interesting because I I deeply believe in what you're saying. And what's interesting is, is for my personal life I've always [00:06:00] kind of been fascinated by.

[00:06:02] Loree Philip: How one decision or one opportunity could completely change the course, the path of your life. And so the example that, and we're getting a little off track here, but I want to share this. The example that I have is that when I went to school to get my MBA, I was scheduled to be in a certain cohort. It was going to be Monday, Wednesday, and I had a colleague who was doing Tuesday, Thursday, and he convinced me to switch.

[00:06:35] Loree Philip: He was like, you should switch and we can do this and all this. So I ended up asking, requesting to switch, and I ended up meeting my husband in that program. And so I just, and a lot of my friends today, and I know you go through a program like that. With the purpose of also making very deep connections and networks.

[00:06:56] Loree Philip: But a lot of the friends to my, to this day that I still keep in touch with [00:07:00] were from that cohort. And so I think about what if I would have just stayed in one day, what the first, what was given to me originally. So I'd like to switch gears here a bit, Kristina, and talk about. Gender equality at the top, and this is one of those topics.

[00:07:22] Loree Philip: That has been coming up a lot more lately in the news and conversations and things that have people are looking at this because not only are women wanting those positions. I think people are starting to pay attention to the, not only the importance of having diverse perspectives. at the top of leadership and the importance of that.

[00:07:46] Loree Philip: And so you see things out there focuses like your company supporting women to do this, but also like organizations like chief that were designed to support women to have stronger networks and resources. So [00:08:00] from your perspective and having been a CMO, how, how's this going? Are we, are we making progress?

[00:08:09] Loree Philip: Where are we at right now?

[00:08:11] Kristina Cleary: So to be honest with you, one of the reasons why I started my company was due to a complete frustration with the system and with statistics hearing 200 years till gender pay equity is going to happen 140 years until we get power and leadership equity at the top.

[00:08:30] Kristina Cleary: And to me, I hear those statistics and it's not okay. Like we know it's going to take 200 years. If we know that, why is it going to take 200 years? And I know that these things take time, but to me, 200 years seems absolutely ludicrous. As particularly in today's world with all of the technology we have with all of the intellect that we have and people in power that we have.

[00:08:53] Kristina Cleary: I'm doing my part with a, with a small business and trying to drive that change one woman at a time, because [00:09:00] I truly believe this needs to be not only a top down movement, but a ground up movement where women need to take the initiative and can drive change themselves as well.

[00:09:09] Kristina Cleary: Unfortunately in every role that I had, no matter what the industry, there were always a handful. A very small handful of women at the top, including myself in my last position. And so I had a very deep interest in running the women's employee resource group and trying to figure out the tools and the resources that women need.

[00:09:33] Kristina Cleary: And if you look at the latest McKinsey lean in study it's showing that at the bottom of organizations and even in the middle, it's about 48%, 50, 50 gender equity when it comes to the roles. But when you get to the top, it's 24 percent and below which is really it is frustrating. So there's this leaky pipeline of women to the top.

[00:09:54] Kristina Cleary: And the question is, how can we plug those holes in that leaky pipeline and [00:10:00] keep more women in the system. Like you say, we know there's tremendous advantages to organizations that are gender diverse at the top. So what can we do to plug those holes? And I'm hoping that my programs and services that are supporting women with the content, with the coaching, and the community, and the collaboration that they need with other women will help to do that and keep as many women as possible in the pipeline and also support them on their journey to the top.

[00:10:27] Kristina Cleary: Mm

[00:10:28] Loree Philip: hmm. Yeah, I, I think it's important, as you mentioned, that we look at it from both, both lenses. Top down and bottom up and the you know if we wait for companies to catch up on their own we're gonna be waiting for a long time and there there has to be a Things we can do as individuals, as women if we want to move up.

[00:10:56] Loree Philip: And I know that's not the path that's right for [00:11:00] everybody. First for me, it's always about decision and being intentional about your decision because sometimes we hear, and I, I've talked to A person on my podcast previously who she, she made it to the top, she made it to CEO and she did it because she thought that's what she was supposed to do and when she got there she realized that it wasn't for her.

[00:11:22] Loree Philip: So I think the first step is, is really thinking through. Is this the path for me? Yeah. And then if that is true for you or you feel like that's your your passion and what, how you want to focus in on your career at that point, what can women start to do to position themselves to not fall out of that leaky middle?

[00:11:46] Loree Philip: Because I saw that too, and it was just like part of it was there was a point where women were not getting promoted to that next level. And so then they couldn't, they weren't ready to be pulled up all the way to the top, right? Like they're not getting [00:12:00] that, that experience.

[00:12:01] Kristina Cleary: It's an interesting, it's an interesting step for sure is really being intentional and going through that visionary process of where you want to be.

[00:12:13] Kristina Cleary: And why you want to do it and why it's important to you. And I think that in all of the leadership programs that I run, we walk through kind of vision and goals at the beginning, along with the mindset work, because it's true. Like a lot of women that come into the program, they think, Oh the next step for me is partner at this law firm or this accounting firm or this consulting firm.

[00:12:34] Kristina Cleary: And then they come into the program. They're like. Actually, I don't want that or they might come to the program with, yes, I want that, but I want it to look differently than the role models that I see at the top because they're not spending time with their families. So there's a couple of like factors at play here is the more women we get to the top, then we'll be able to see role models who are making it all work and might have, might be spending their way differently than the [00:13:00] role models we see at the top right now.

[00:13:01] Kristina Cleary: I also think that's an important consideration when women are thinking about. Whether the top is, is where they want to be or not. I specifically had a client go through my program last year and she was in tears on the last day saying that the program was so transformational for her because she was on partner track and she had decided before she took the program, she didn't want to be a partner by the end of the program, she's I want to be a partner like that's what I've always wanted, but I thought I couldn't do it because I see how the role models ahead of me and nobody is a mother, nobody is a parent, nobody is like working less than 16 hour days, but I'm going to do it and I'm going to redefine what that means and I'm going to be a role model for other women who are looking to get to the top.

[00:13:46] Kristina Cleary: So I think that we're in this huge opportunity phase at all generations for women to support one another. And to kind of redefine what some of those roles even look like at the top.

[00:13:56] Loree Philip: I cannot emphasize that point [00:14:00] enough. I just can't. When I was in corporate, I self selected out of a lot of opportunities because I decided that I couldn't live my life and prioritize my family and have the balance I wanted if I were to take those positions.

[00:14:19] Loree Philip: But what I didn't see. Was that just because there isn't a person in that position that is doing it successfully and in the manner that is a, a role model is that we could be the leader become the leader that you wish you had. Yeah, become that role model and we need to start creating more opportunities for women to come in.

[00:14:46] Loree Philip: And there is a bit about flexibility in the culture of wherever that is to allow for that because I know some cultures are very, very hard to change. And so it's not like we're saying, yeah, [00:15:00] just go into this position and act however you want because I know that's not. Easy, right? But, but in order for us to make real progress, if we want to see more women at the top, we have to show that it's possible for that woman to have the legs that they want and be in that position, or we're going to self select out.

[00:15:21] Loree Philip: And that's what I hear is that that woman you're speaking of, she was at that point where she's I can't do this.

[00:15:27] Kristina Cleary: Yeah, exactly. And it's unfortunate because there are, I think that that's, I guess it's unfortunate and it's opportunistic and exciting that we do have the ability to kind of pave the way and to be those role models for the next generation as well to see that there is a different way of doing things that you can try and do it a different way.

[00:15:48] Kristina Cleary: And like you said, it has to be within an organization that is willing to support that type of culture. I can't, I can't I can't tell you the number of times I've been part of an executive team where the executive [00:16:00] team meetings are either at 8am or 6pm and it's any working professional mother knows that those times are virtually impossible to make if you need to be there for your children and no one's going to take those executive times unless you get somebody who is a working professional mother at the top who recognizes, listen, We got to make these times work for everybody particularly if they're in person, obviously, like things the way that they are now, there's an opportunity to work virtually, which increases the flexibility, but that's just like a very specific tactical example.

[00:16:34] Kristina Cleary: If you get somebody who is. a role model who knows the circumstances of women, particularly working mothers, and they can drive the change in simple things like meeting times, for example.

[00:16:47] Loree Philip: Yeah, a lot of those little, little details are very impactful, right? Like, well, I can't really make this meeting without having to drop off my kid, or then [00:17:00] you just have to have somebody else do it, and then you feel guilty that you're all the mom guilt for not being there for your kids, and it just starts to escalate from there.

[00:17:08] Loree Philip: So what can we do as women if, if I've decided I would like to move up the chain, and, and my path is to move up and become one of those role models for others? What, what are some of the key elements that you've decided, okay, these are the things that somebody. Needs to sort of think through, do, get supported in what do you see

[00:17:35] Kristina Cleary: there?

[00:17:36] Kristina Cleary: Yeah, so I think there's, I think there's two pieces to that particular question. One is the things that women can actually do themselves and we're living in an age where there is access to information and resources like 10, 20 years ago. Women have the ability to tap into tools, to tap into communities, into coaches that can really support their journey.[00:18:00]

[00:18:00] Kristina Cleary: Now, of course, if somebody wants to move up, I want to come back to your point where you do need to ensure you're in the right organization and culture that is going to support that. So there's a few things. One is like ensuring that you understand what your network is. And I like to encourage women to build a personal board of directors.

[00:18:19] Kristina Cleary: We all know the most successful companies in the world have amazing board of directors. Why do they have them? Because they're drawing on talented individuals that are bringing experience from other industries, from years and years of experience, from other roles, etc. But that's a support system for the organization.

[00:18:36] Kristina Cleary: So I like to think of individuals as having a personal board of directors, too. And those are people both inside your organization and outside your organization. People that you can lean on, who are going to support you, who are going to sponsor you, who are going to look out for your best interest, who you can call in a time of conflict.

[00:18:53] Kristina Cleary: And you can build that personal board of directors with people that you know. You can reach out to people and ask for [00:19:00] connection. You can hire people whether they be mentors or coaches, you can join online communities, you can join courses, etc. So there's a lot of things that we can do as individuals to support our journey.

[00:19:12] Kristina Cleary: The second piece is Organizations themselves need to invest in their women and provide them with access to the tools that we need. And this is one of my areas of deep frustration is we see more and more organizations saying they support diversity, equity, and inclusion. Look, we sponsor this event once a year.

[00:19:31] Kristina Cleary: It's great. You're like a sponsor and you slap your logo on and you can say you support diversity, equity, inclusion, but really working for an organization that has a strong culture, programs, employee resource groups, budget to support the development of their women, I think is really important as well.

[00:19:48] Kristina Cleary: So I think it's important as women that we, A, build our personal support system and really put an effort into tapping into the tools and resources that we need. And then B, [00:20:00] Organizations supporting and providing tools to women as women. We can choose to work for those organizations. Mm hmm.

[00:20:06] Loree Philip: Yeah, that is it.

[00:20:08] Loree Philip: It makes so much sense around getting the support we need for ourselves. And the thing I want to add there is, and I might have mentioned this before on the podcast, but sometimes We as women don't like to ask for help and get support. We like to do a lot of things on our own and we can do so much on our own.

[00:20:30] Loree Philip: And I totally understand that I'm not one to reach out to others to ask for support, but I will tell you this most. People, especially senior leaders, have support and a lot of support and so it is not expected that you make it up, navigate that path on your own. It isn't. It isn't. It is the support is so important.

[00:20:57] Loree Philip: It's, it's there for you [00:21:00] if you would like to invest in it or find take the time to tap into your network, et cetera. On the company side, I was, I was nodding my head at you because we're just. There's so many companies right now talking the talk and not walking the walk. And I know it's hard because it's culture is hard to change.

[00:21:25] Loree Philip: And the, the point where we struggle with a bit in seeing what companies are doing is that we're expecting so much more. For women, we're talking about, Oh, we want more women on the board. We want more women doing this. We want, maybe your, maybe companies are even promoting women to these positions.

[00:21:46] Loree Philip: But they're not supporting them. They're not giving them the tools to be successful, and the training, and the coaching, and the, and so when they fall flat, or maybe they're feeling the, [00:22:00] the imposter syndrome that has been talked about so much lately is because we're pushing on women to be more, do more, and they are But because they're not supported, they get this feeling that that they're not ready or they can't or they haven't and so I think If we can work on both, that would be amazing.

[00:22:24] Loree Philip: What are you seeing there with your clients around this idea of imposter syndrome? Has that been coming up

[00:22:31] Kristina Cleary: often for you? Absolutely. I mean, I think the latest statistics I saw was like, 70 percent of people in the world suffer from some form of imposter syndrome. Even the most successful actors and actresses that you see out there, and you see a lot of quotes, especially on social media.

[00:22:47] Kristina Cleary: Excuse me. So I would say one of the, the modules and a lot of the programs that I've worked through, there is a pretty heavy mindset element because even the most successful people like myself [00:23:00] when I was at a C level organization, when I went out on my own, it was a change of things and it's so you start to have these thoughts of can I go out on my own? I've always worked for somebody. I'm not good enough to go out on my own. I'm not smart enough to go out on my own. Like whatever forum that your imposter syndrome might show up as it is prevalent, and I think that it's specifically prevalent in the population of women that I work with and that I communicate with.

[00:23:26] Kristina Cleary: And I think that's one of the best things about ensuring you're part of a community. It's amazing what can happen with those thoughts when you know others have them and when others have your back and are supporting you. How quickly those thoughts can be turned from ones of negativity to ones of opportunity and positivity.

[00:23:46] Kristina Cleary: Mm

[00:23:46] Loree Philip: hmm. Yeah, that's, that's, I think that's such an important point because oftentimes when we're. In this place of can I do it gosh, it's, it's a stretch for [00:24:00] me or whatever it is, we forget that that is just part of being human and, and I love to think about it in terms of if you're feeling imposter syndrome or that kind of uncertainty or doubt.

[00:24:18] Loree Philip: Good job. Like you are not being complacent. You are not just doing the same thing every day. You're trying to grow. You're trying to learn. You're trying to expand and these things will come up when you're doing that. And so it's almost I want to say a badge of honor, but you know what, you're, you're doing something hard and, and good for

[00:24:43] Kristina Cleary: you.

[00:24:45] Kristina Cleary: Yeah, I love that. When you are uncomfortable, that is definitely when you are growing and you're going through a change. And I think that one of the most valuable concepts that I've, that I've learned and that I work with my clients on is this [00:25:00] idea of this thought loop. And I don't know if you've, if you're familiar with that, but it's very easy for our brains and our emotions to essentially protect ourselves with these negative thoughts, right?

[00:25:11] Kristina Cleary: Because if we don't do something, if we don't change, then we're safe. So it's very hard to break through and to have the courage to take that leap per the, per your podcast title, dare to leap. And if you, if you take that leap What I would recommend is like being intentional about your thoughts and emotions around that because this thought wheel essentially goes like this you have a thought and it typically comes from your core beliefs and That thought will drive your emotions which drive your behavior and produce the results So if you start with a negative thought then you're going to have negative emotions.

[00:25:46] Kristina Cleary: You're gonna have negative action and negative results But you turn that the other way and if you can work really hard to produce a positive thought, then you're driving positive emotion. You're driving change and action leading to the result that you [00:26:00] want. So it's just a very simple tool when you catch yourself with whether it be imposter syndrome or a negative thought to really think that through and try and reframe that in another way that would better support the actions that you want actually then results that you want to drive.

[00:26:18] Loree Philip: Yeah. This, this is. Really powerful because I, I'm a big believer in the importance of mindset and, and your, how your thinking manifests out into the world. Mm-hmm. And sometimes we get caught up with external things I would like to go get that next position. I would like to get that. Raise, I would like, but the, the, where it starts really is, is you're, you're thinking about that.

[00:26:50] Loree Philip: You're feeling about that and then your, your actions and how it comes through. And so it's not that it's impossible to get the promotion when you have [00:27:00] negative thoughts, but you don't have to make it so hard on yourself by beating yourself up along the way. Right? Why not? Make grease the, the, the wheel a bit and make it a little bit less of a struggle by shifting our thinking.

[00:27:18] Kristina Cleary: Exactly. That mindset can be a tool for success for you. Mhm.

[00:27:23] Loree Philip: Kristina, we're going to start to wrap up our interview here a bit. I'd love to hear your any last closing thoughts you have for women out there in the middle of their career thinking through what, what am I doing? Where should I go?

[00:27:37] Loree Philip: What, what comments do you have for them?

[00:27:40] Kristina Cleary: Sure. I think that it's a really important message for women to hear that they're not alone, that if you're thinking something, Chances are there's a lot of other women having the same thoughts. So you're not alone. So truly to your point earlier people want to help other people.[00:28:00]

[00:28:00] Kristina Cleary: So it's not only that you need to reach out to people for help and that you don't need to be in this alone, but people generally want to help you. So once you start reaching out I wouldn't be surprised if women are surprised with all of the help and support they will actually get.

[00:28:18] Kristina Cleary: So don't be afraid to actually reach out for help, because people genuinely have an interest to help other people. I truly believe that. Not all of the time, but I do truly believe deep down people want to help other people. I also think that there's a changing tide when it comes to in the past women have been competitors of one another.

[00:28:38] Kristina Cleary: And I think it's important as women, when we rise and when we experience success, that we bring other women up with us. So I would encourage women who are in more senior positions of power and leadership that they remember to support other women and to bring them up along their journey and to support them as much as possible.

[00:28:59] Kristina Cleary: So I think [00:29:00] that no matter what your goals are and your vision is for your life, I would say I just a gentle reminder that you're in the driver's seat to make that happen and to not be afraid to tap into tools and to people to help make that a reality.

[00:29:14] Loree Philip: Yes. Thank you for that. I I love that so much and a big part of this podcast is that you are the driver of your life and in an empowering way just.

[00:29:29] Loree Philip: back to is this even something you want? What is it that you want? Like at the base level of your day to day life, come back to you and make yourself the most important thing. And it's not selfish. It is not selfish. And, and so that is where we want to start. And as Kristina said so beautifully support is there if you're [00:30:00] Ready and willing and open to it.

[00:30:01] Loree Philip: Thank you for that, Kristina. Where can our listeners reach out to you, connect with you, learn more about your

[00:30:08] Kristina Cleary: work? I would love to connect with as many of you as possible. You can find me on LinkedIn at Kristina Cleary. That's Kristina with a K and Cleary with a C. And my website is Excel. com, which stands for Accelerate Her, L is her in French, so A C C E L L E.

[00:30:27] Kristina Cleary: com. And you can subscribe to my newsletter. I try to provide as much value as possible. I share all of my tools and resources. So I would love to see all of you on LinkedIn or on my newsletter. Great.

[00:30:40] Loree Philip: Thank you so much. I really appreciate it.

[00:30:43] Kristina Cleary: Great. Thanks, LLoree

[00:30:44] Loree Philip: thank you so much for listening to this episode. If you've enjoyed it, I would love for you to subscribe. If you're already a subscriber, don't forget to share the podcast with a friend. Hope you all have an amazing week. Until next [00:31:00] time. Bye.