HERspectives // Interview with Sharon Brady

It’s the end of August and I’m happy to report that my babies have indeed survived the first week of the Big K – Kindergarten.  Let me just say, WHY DID NO ONE WARN ME? Ok, fine, I knew it was coming: The day when they would get on a bus and travel to a new land where soft plush toys are replaced by hard desks, cubbies, and worksheets.  The day when they would take a giant leap off my helicopter pad and soar headlong into big-kid childhood.  And no matter how rationally the voice in my head kept saying “they’re ready! they’re happy! Look how great they’re doing…” the truth remains: Transitions are not easy. Change is inevitable and inevitably scary.

I have always been intrigued and inspired by people who can look change square in the face and accept the hard work of broadening their perspectives in the name of growth and fulfillment. As an entrepreneur, I’ve found that embracing change is crucial to not only enjoying the process of growth, but to growing at all.

As someone who advises purpose-driven organizations on how to become more authentic and relevant, I’ve found the exercise of broadening my own perspectives to be critical for keeping myself authentic, relevant, and unbiased.

To that end, I’ve decided to start a project that I’m calling HerSpectives, a series of interviews with women whose diverse range of viewpoints and experiences will hopefully shed some (more) light on the awesomeness of women, and also add fresh insights to my own process of helping mission-driven organizations improve how they market to and about women.

For my first interview, I asked to sit down with Sharon Brady, a long-time friend of my mother-in-law and a woman whose career I’d only known very little about until recently.  Sharon serves as the Executive Director of Leading Women Executives, a program whose mission is to “strengthen and sustain female advancement by developing effective leadership competencies and behaviors while partnering with organizations to address company-specific business practices and cultural issues.”  Aside from having a really great pair of loafers, Sharon is remarkably self-possessed and refreshingly humble.  And as we sat down I found myself wondering, what superpowers does she possess?  How did she manage to break through the glass ceiling and then pivot to find purpose and fulfillment in retirement? Our interview explores unconscious bias (we all have it!), the importance of self-awareness, and some of the ways that her organization is helping women to develop insights and strategies for becoming the best versions of themselves.

On an intellectual level, so much of what we talked about really got my wheels turning and provided insights that I’ll certainly be able to apply to my work.  But I have to say that the most impactful element of our conversation was how I felt during and then in the days afterward, while I was processing everything.  It’s very safe to think about something conceptually, which is what I’m trained to do – but as I was talking with Sharon and taking in some of the examples she gave, i.e. being uncomfortable talking about/revealing failures, comparing/judging ourselves… I could feel myself struggle to – wait for it – not judge myself. Isn’t that crazy?! Of course it isn’t, the research shows us that it’s actually exactly what women tend to do.  Still, the emotion of it all took me a little off-guard, which is what I think happens when you dive deep.  Without anyone telling me/hiring me to create HerSpectives, I have forced (and allowed) myself to sit with the emotions that are otherwise easy to set aside in the name of research and objectivity.  It’s a been challenging to wade through them all, but it’s also pretty remarkable how empowering it is to do just that.  It’s no surprise that this is one of Leading Women Executives’ specialties…


This interview has been edited and condensed.

DH  I want to ask you about your transition into retirement. Based on what I know you to be presently involved in, it looks a lot like a career! Now that you’ve been officially retired for 2 years, is it as you expected it to be?

SB  Initially, my view was “Great! I’m going to do pilates, I’m going to learn to play bridge again; I’m gonna spend time with my kids, family, I’m gonna garden…” do all that good stuff. But when I communicated to people what I was going to do, that I was going to be retiring, all of a sudden all of these options started to pop up. And people starting saying “Oh you know you can’t just retire, you’re not the kind of person who can just sit at home.” And I started thinking there’s a message in here somewhere – and actually there was a lot of truth to that.

I started working with Leading Women Executives while still in my corporate role. I knew the women who founded it quite well, and so when they approached me with this it was really intriguing because it gave me the opportunity to transition – to not just stop cold – but to continue to work with really amazing women in every way you can think of. It gave me the opportunity to shift. I was surprised at how important it became to me to be able to have another reason to get up in the morning, doing something where I was really making an impact. That’s always been something that’s motivated me, I’ve always been a real change-oriented person, most places I’ve been, that’s been a large part of my role, to drive change. And so with this, I was able to impact change around something that I cared a lot about. But it wasn’t what I had planned on. And it’s been really gratifying, and I’ve grown and learned a lot of new things.

DH Have you had to unlearn anything?

SB A lot of my assumptions came from my own experiences largely. I’ve had to broaden my perspective, to be helpful to the women in the program. My corporate experience, my professional experience, some of that will translate. But every situation is different – cultures are different.  I did a lot of coaching in my HR career, but this has kind of pushed me to bring a different perspective, so that’s been really cool.

I think that the other side of it though, is that it’s really given me an opportunity I never had. When you’re inside an organization, you are governed or limited by that company’s environment. You have to figure out how to work within that to make an impact. And I don’t have that limitation in this role. So what it’s allowed me to do is be even more straightforward and open both in terms of feedback to the women and helping them interpret some of what they’re experiencing and learning for themselves; I always felt within a corporate environment, you always had to do a little bit of toning it down.


SB  Yeah. I don’t have to do that. And that’s been really nice.

DH Tell me more about how you help the women in your program navigate their corporate cultures.

SB  We take them through a process of self-exploration. They go through the Hogan Assessment. It gives you insight into how you’re wired up, and how you’re likely to respond to different situations. It’s not like Meyers Briggs, but it’s a good partner to it. In particular what it gives you insight into is knowing your proclivities in terms of how you approach situations and people.  It also helps you get a sense of where your derailers might come in. Especially when you’re in more senior organizations, 99% of the people who are in those more senior roles are pretty competent. Unless there’s a real Peter Principle going on. The thing is that people fail largely because of culture and fit reasons. So it helps people see themselves through that lens and then we take them through a process of examining their own story. We call it their leadership story. They often come trying to just walk you through their resume, but we say no no no, let’s go back and talk about your life experiences and how they’ve shaped you as a leader. For example, when I tell my leadership story, I talk about how my dad was a career military officer, we moved all the time, I was an only child, and how those things play into who I am. It’s not so much a psychological dig – it’s more about where you’ve been, what circumstances and situations have made an impact, people who might have had an impact.  And then we ask them to reflect on how they’ve faced certain circumstances in their careers and in particular what they’ve learned from situations that haven’t gone well.

And we do that for 2 reasons, because a lot of times people have difficulty talking about things where they failed. And part of what we’re trying to say is you need to talk about them, get to know them, and realize what you’ve learned from them and how you can diagnose situations and better respond to them in the future, and then we marry that up with this research on women. The idea is to say, here’s the research on women, here’s where unconscious bias comes up, here’s where it’s the double bind that we talk about with women; you know, if you’re too aggressive, you’re told to tone it down; if you’re not aggressive enough, you’re not seen as aggressive enough, blah blah, and women are always adjusting in corporations around that.  So the coaching we do is to help them think this through and to use the other women in the program to help get that insight about them.  As an example, we can say, “based on what I’m seeing about you, this is clearly a challenge…”

DH  It’s building self-awareness.

SB  Right, and so that ability to help them diagnose and then to give them straightforward feedback, is really important. Because what we want for the women in our program is first-and-foremost to leave with a much higher self-awareness.

DH  The women in your program are sponsored by their employers. It must be challenging to get them to let go of some of their old habits and mindsets about themselves.

SB  We get a lot of women who are like, “I don’t know why I’m here”, and “I’m really uncomfortable in a program just for women because I built my whole career saying LOOK, don’t treat me any differently.”

DH  I was raised to be aggressive, to ask for what I want. My dad was a big proponent of blending in with the guys.  And I was always really comfortable with that when in his presence.   But I think you feel a discomfort inside yourself when you’re sitting next to another woman who contrasts you. Example, my mom is more passive than me, and I could always feel the difference when I was in her presence, like I was taking up too much space. Around her, I felt the pressure to be smaller.

SB  We take the women in our program what is called the Unconscious Bias Test. It’s a word association where you take a word and you say whether the word is associated with a man or a woman. And the women in our program take it and then we show what the answers tell them, and invariably they show bias. And they’re stunned. But it’s a way to illustrate that everyone has it. Unconscious bias isn’t a good or a bad thing, it just is. Everybody’s got it.

DB  Tell me more abou the women in your program.

SB  Most of them are between 40-45. They’re not all married. They don’t all have children, but they definitely are in that stage where if they do, they’ve got a lot of demands.  In this age group, women are also starting to see the probability of demands coming from other parts of their family – their parents maybe. So this whole idea of work life balance is always a big topic of discussion. And what we tell the women in the program is that from our experience, there is no such thing. It’s not a balance question, it’s not an either/or question. It’s an alignment question. Being much more thoughtful about the commitments that you make and how important those are to you. As an example, we have women in the program who have 3 small kids a husband who has a very different kind of job, maybe their mom lives with them – all these things that we see—and they’re angsting over the fact that the other women in their company are serving on two non-for-profit boards, and blah blah… And we say everybody’s at different places. At every point in your life you have to figure out what’s important to you, and then you need to align where you’re going to put your time and effort around that. And some people can do all these things at different points in time, but you’re not them and they’re not you. And it’s helping them get perspective because they just feel like everyone’s judging. Which is much more prevalent with women than with men.

DH  I’ve read that in the formation of identity, men learn to view the world through their eyes with a focus on where they are and what they’re doing. They pick up a glass of water and see the glass of water. A woman picks up a glass of water and she sees herself pickup up a glass of water. Amazing. So think about the layer that this adds to everything.

SB  The other thing that we see I would say with some approaches to this issue of women and opportunities is that somehow women are flawed. That what you just described is a problem, a flaw. This whole discussion that women lack self confidence. Do they really lack self confidence, or have they experienced that depending on what they do, there may be penalties associated with certain behaviors? And are they then a little more cautious as a result?  So it’s more than actually lacking self-confidence.  Our whole philosophy is that there isn’t anything wrong with women – it’s just helping women see these things and think about how they can adopt different strategies so that they can be more connected. More aware. As opposed to feeling like there’s something wrong with them.

One of the things we talk about, which is research based, is how women show up in negotiations. It’s really simple, when women negotiate for their firm and for others, they tend to do it really well. But they don’t do it well for themselves, they’re not comfortable there.  These are very successful women! We help them explore why this is – why are they tentative there? So we peel that apart.

DH  I once worked with a woman who was promoted 3 times within her company without a raise.

SB  And wasn’t she thrilled? She got promoted!

DH  I do have one last bonus question. If you could identify one “failure” that served as a large lesson for you in your career, what would it be?

SH  One thing we all do in the program is share our stories, personally and professionally. And sometimes they are very personal things, and it’s about giving these examples that show we’re all real people. One of them I talk about consistently was that I had a really solid career in a great company in Chicago, on the right track, doing all the right things, and was starting to feel like I was going to get topped out.  And at the time, I was trying to over support and encourage my husband to be more aggressive in pursuing his career.  An opportunity came up for him which was a great opportunity but it meant we would have to move. I encouraged him to take it. I quit my job. We moved away from the Chicago area. Ostensibly for all the right reasons; but the truth is, in retrospect, I was pushing it hard because I wanted to encourage him and test out a different lifestyle and see if as a family we could be less dependent on me; so really, not for all the right reasons. It resulted in a lot of good family learning; it resulted in me coming back to Chicago and taking a job with another company which at the time was very difficult because the company I went to work for had a much different environment than where I was before; and then our son, I think, paid the price for that; he made the move out very well, he didn’t make the move back very well. And he’s amazing man, all those things, but it was a very tough couple of years and now it’s part of his journey, and you have to ask yourself did that need to happen? Probably not.

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