163 How Women Rise: Sally Helgesen on Leveraging Women’s Greatest Strengths As Leaders, Innovators and Entrepreneurs
Sally Helgesen is on a mission to help women to recognize, articulate and act on their greatest strengths – and help companies organizations create more inclusive cultures. Bestselling author of How Women Rise and renowned leadership coach, Sally talks about the “perfectionism trap” and other traits that stand in women’s way, and how to step into true empowerment as business leaders and entrepreneurs.
Melinda Wittstock: Welcome to “Wings,” Sally.
Sally Helgesen: It’s wonderful to be here, Melinda.
Melinda Wittstock: It’s wonderful to have you. I am excited to hear about the spark that led you to write this wonderful book, “How Women Rise,” which is doing extremely well. Lots of people are buying it. It’s wonderful.
Sally Helgesen: Yeah, it is. It’s been a real phenomenon. Well, here’s the backstory on it. I’ve been working in women’s leadership, writing books, delivering workshops, seminars, keynotes, doing coaching, for 30 years. About 2012, I began delivering a new workshop. I developed it for a big program I was doing of Women in Technology, Asia-Pacific in Singapore. I decided to look at the competencies women really needed at the higher level in their career.
What I came up with based on my own research was the competencies of being visionary, connected, intentional and present, and designed a workshop which I did for about six years based on that. It was very successful, but when I was working with the intentional part, it was about being very intentional in your career and your personal development, I decided to use my colleague Marshall Goldsmith’s huge bestselling book called “What Got You Here Won’t Get You There,” about the behaviors that get in the way of successful people as they move to a higher level.
I found his template fascinating, the idea that what serves you earlier in your career can get in your way as you move higher, but that you assume more responsibility as an entrepreneur, or however you’re doing that, but that you’re invested in those behaviors because you believe they’re responsible for your success, so you have a tough time letting them go.
I thought that template was terrific, but as I worked with the material in my workshop, it became very apparent to me that the behaviors he was identifying were pretty male behaviors. Some of them were gender-neutral, but a lot of them were very male. Not surprising, given his coaching base, he’s the world’s number one ranked executive coach, so he works with CEOs and it’s about 80% men. He would have behaviors in there like, “Learn to apologize.” Well, guess what? There are a lot of women who can’t even open their door without saying, “I’m sorry,” so that’s not a big female problem. He’d say things like, “Don’t talk all the time about how great you are. Don’t try to claim credit for everything,” et cetera, et cetera. “You don’t need to win too much,” those kinds of behaviors which really aren’t that problematic for women.
I thought about it, and I ended up suggesting that he and I collaborate on a book that took the premise of the behaviors that serve you well early on may not serve you well later, but look at it from the perspective of, what are the behaviors most likely to get in women’s ways. We’re not saying these are women’s behaviors. We’re just saying, these are the behaviors that are most likely in our combined, I guess, 70 years of working with leaders around the world that are most likely to get in women’s ways. We dissect them, we offer examples, case studies.
Then a good part of the book is also on, how do you begin to change habits that are ingrained? That’s based more on a coaching template. I think that combination, what we were looking for was a way that women could get more in control of their own development. I’ve had pushback since the book came out. “Oh, we need to be talking about change in culture and structure first.” Well, fine, but actually the way culture and structure change in organizations and in sectors is by having more women in leadership, so what we need is more women in leadership. To do that, one of the things we can do is alert women to habits that may not be serving them well in terms of positioning themselves as leaders.
Melinda Wittstock: It is so interesting, Sally, what you say about women coming up the corporate ladder or launching careers as entrepreneurs and looking around for mentors and coaches, and finding only men when they were getting to that higher level. Likewise, very, very difficult to find female role models.
Sally Helgesen: Yes.
Melinda Wittstock: There were two things that I’ve observed, one where women felt they had to be like men to succeed?
Sally Helgesen: Yes.
Melinda Wittstock: Right? Which was kind of inauthentic. It didn’t really quite work, on one hand, and made us very estranged from ourselves on some deeper level. On the other hand, what you’re talking about, if we’re coached to apologize all the time, heaven knows, we’re always apologizing all the time, right? This is really fascinating, because when you look at women right now, what are some of the biggest mistakes you think that we are making as we either climb up the corporate ladder or set off on our own to create businesses and try and grow and scale those businesses?
Sally Helgesen: Yeah, and I think your point is exactly right. Fortunately, we’ve gotten through the time when the idea was, women just have to learn to be like men, because that not only was inauthentic, but it’s also not acting on what your greatest strengths are, because being a woman is part of your identity, so your greatest strengths are not necessarily going to be very manly strengths. It’s kind of a no-win for women.
What I find now, and what we were looking at in the book, I wouldn’t say so much mistakes, but behaviors or habits that help keep women stuck and prevent them from fulfilling their full potential. This book came out on April 10th, and I’ve been traveling constantly ever since and probably doing a seminar or a keynote or a leadership program based on the book almost everyday since it came out, so I’m learning which ones of these behaviors get the most endorsement, in other words, the most women identify with. A couple of them really stand out.
One is Behavior Two in the book, which is expecting others to spontaneously notice and reward your contributions. That is, declining to take the responsibility for getting noticed by failing to communicate what you are doing and the value of what you contribute.
I’ve noticed this for years.
Women will feel bad because they feel as if their contributions aren’t being noticed or affirmed. You know, if they’re a company by their boss, if they’re running their own company generally in a sector or by competitors or colleagues or clients. But then when you dig down, when you’re working with them, you see that they’re really expecting that these things would be noticed rather than being very explicit. “Hey, here’s what I’m doing, and this is why I believe it’s important, and this is why I believe that it is valuable to you,” whoever you are.
And being very explicit about that rather than hoping other people notice, I’ve recognized and worked with this behavior for years, having worked in partnership firms some years ago doing a study, where I asked the women who are partners, “What are the greatest strengths? And what are the greatest impediments of the women in your firm who may make partner one day?” What I always heard over and over was, “Greatest strengths are ability to do A-plus quality work.” And really, they’re reliable. They’re conscientious. They’re diligent. They really get the work done. What they’re worst at is getting known for the quality of their work.
And often when I’d ask the younger women in those firms, “What holds you back?” I would hear one of two responses. It would be either, “Well I have to be like that idiot down the hall to get noticed around here. No thank you.” In other words, setting themselves up by looking only at the most obnoxious person or just hanging back. So setting up this sort of false either-or for themselves. But the other thing I always heard was, “I believe that if I do great work, people will notice,” and maybe in a perfect world that would be true. But generally, it’s not true.
Melinda Wittstock: No, this is so interesting because men spend so much time on the relationship, on a bond. Whether it’s at the golf course, lunch, whatever, but just so much more time on that, because relationship is the leverage, is the capital, right?
Sally Helgesen: That’s true.
Melinda Wittstock: Of any business, right? So without that relationship … If you’re looking at it from the perspective of an entrepreneur, at a startup stage, you’ve got to go persuade people to work for you for free. You’ve got to persuade them about your mission. You’ve got to do all kinds of things. You’ve got to attract. Maybe you have to educate and make a whole market. You’ve got to go change-
Sally Helgesen: That massive [crosstalk 00:20:55]-
Melinda Wittstock: Yeah, you got to change behavior. You got to do all that kind of stuff. So, in order to be able to do that, it’s relationship is everything whether it’s one on one or whether it’s how you show up on social media or any of these things. And yet, if you’re just sitting there and doing great work and no one knows and you’re in isolation, this is one of the things that holds back women entrepreneurs as well.
Sally Helgesen: It certainly does. For years, I’ve watched something. I’ve seen women come into a new position, a new company whatever. What they’ll say to me is, “I’m going to spend the next six months with my head down, learning everything I need to learn and becoming really good at this or becoming an expert.” If they’re an entrepreneur, “I’m going to spend that time studying the market. I’m going to spend that time studying competitors, devising the structure of how we’re going to do it — my go-to-market plan. But six months, focused on creating something and improving my expertise and designing this.” Then you’ll hear guys come in. Their first question is, “Who do I need to know to make sure this is a success?”
Melinda Wittstock: Right.
Sally Helgesen: Then they go out and do that. So what’s the outcome? What is the outcome for the women? Less support, less visibility, and a whole lot more work. So that’s sort of the other side of this expectation, is this overvalue of expertise, which I think is very understandable because women have often had their expertise questioned and have encountered skepticism about what they have to contribute. So the way to defend against that is to become very expert. But boy, can that get in your way? Whatever you’re moving into, your job is to start building allies from day one. And yes, before you even are very confident about knowing that you can talk about what you’re doing very well, you need to start enlisting allies and that gives you your leverage, as you say.
Melinda Wittstock: Well what’s interesting is we go back to women’s unique ability. The fact that we are much more relationship focused, actually, in fact, with that empathy and the ability to be very inclusive, it seems like such a contradiction in terms that we would be the ones isolating ourselves when actually we’re very relationship focused. How do you explain that?
Sally Helgesen: Well the way I explain that because this is a conundrum that I struggled over for years. When I wrote the book, The Female Advantage: Women’s Ways of Leadership, published in 1990, the first book to focus on what women had to contribute rather than how they needed to change and adapt, I wanted to identify the leadership skills of the best women leaders. The number one I came up with was enormous skill in building and nurturing relationships, and being attentive to the details of relationship. So then, as time went by, and relationship building became recognized more as a mainstream leadership skill, because back in 1990, it wasn’t. People say, “Oh this is a soft stuff.”
Now everybody recognizes that relationships are the key to success. I thought, “Well if women are great at building relationships, why aren’t they benefiting more from that?” What I began to recognize as I studied it and interviewed women about it, is that although women are great at building relationships, they are often … and this is key for entrepreneurs. They are often less comfortable leveraging those relationships. That is devoting … using the network that they have built strategically so that they and other people benefit. So they’ll devote a lot of effort to building this wonderful network of connections. I’m not saying that that’s not a great thing because women, a lot of women’s resilience comes from the richness of their connections with other people.
That’s been demonstrated that men tend to be less resilient often than women because they don’t have these wonderful, personal networks of support. But then women will build relationships without leveraging them, because when women are often reluctant to leverage relationships to say, “Hey, here’s something that would really be helpful to me right now. If you have any ideas, can you introduce me to this person so I might be able to get that done?” You know, “How can you help?” And of course, “Oh by the way, I’m glad to help you on things too.”
Melinda Wittstock: Well this asking for help thing is so hard for women. I don’t know what it is, where we think, or we’ve been conditioned somehow to think we have to do it all ourselves. We have to make it perfect before we can ask for help. It’s kind of backwards.
Sally Helgesen: Exactly, and I think there are two things. Number one is this perfection business, which we can talk about in a moment. But I think the other thing with leveraging relationships, when I talk to women who have big, robust networks and are reluctant to leverage them, usually what I hear is, “Well I want those people to know that I value them as people,” or, “I don’t want people to perceive me as a user. I want them to perceive me as a friend.” So again, they’re kind of setting up an either-or situation where they’re either just a wonderful person who’s constantly building relationships and being helpful to other people, or they’re a real user who’s only out for themselves and secret … this terribly ambitious person who uses friends.
Sally Helgesen: I also believe that perfectionism gets in the way here at times. Perfectionism, we really define in the book is, believing that anything short of a flawless performance will constitute failure. This can make you reluctant to take measured risks while also creating unreasonable stress for yourself. I would say, Melinda, that the feedback I’ve gotten is that the perfection trap, which is fairly common for women. Some not-surprising reasons is probably the biggest impediment when it comes to women being entrepreneurs, partly because that commitment to perfection … You’re exactly right. It’s one of the reasons you keep your head down at the beginning. You want to make sure you have everything right and in place before you bring it to market, before you start engaging allies, before you start asking for help.
So that’s problematic in itself. But also, being vested in trying to be perfect and get the product to its most perfect iteration rather than beta-ing it as you go along. When you’re invested in perfection, you are, by definition, going to be risk averse to some degree because taking risks increases the likelihood of failure and screw-ups and less-than-optimal outcomes. So, having a tolerance for risk is something that’s absolutely essential for any entrepreneur. An ability to exercise good judgment and deciding which risks to take, but you really need that risk tolerance. There’s one other consequence of perfectionism that’s just deadly at the entrepreneurial level.
Being an entrepreneur, and I speak as someone who’s been self-employed for over 40 years, creates … It’s inherently stressful because you’re managing so much on your own. You’ve got a lot riding on everything. When you’re trying to be perfect, you create much more stress for yourself, but you also create stress for other people. I’ve never ever, ever met anyone who said to me in all my decades of working in this field, “I have a perfectionistic boss and I just love it.” People don’t like to work for a perfectionist. So if you’re trying to engage people and get them going in a startup or an entrepreneurial venture, being a perfectionist is a pretty good way of assuring that you will not be successful in engaging talented people long-term.
Melinda Wittstock: Well what is it underlying the perfectionism? It’s sort of a control in a weird way and underneath that need for control over yourself and by extension over other people. If you’re a perfectionist, you’re demanding, you’re putting your own perfectionism onto them. What is underlying all that? Is it just basically a fear?
Sally Helgesen: Well I think it can be a fear, but I think it’s also that there are some environmental causes. Girls tend to be rewarded for being really good students, A-plus students. Boys have a little more latitude often, especially if they’re good at sports. There’s a tolerance in our culture for the kind of adorable bad little boy. Not much tolerance for a bad little girl. That tends to be judged differently. So I think there are different messages from home and school that shape girls’ experience. But just as important and probably even more so is that in the workplace … And we’ve done some really interesting research here with some coaching consortiums.
One of the things we find is that in organizations, women tend to be rewarded for precision and correctness. That’s what gets them rewarded and gets them that next job. “Wow. You are so … You really did this precisely and correctly,” whereas men tend to be rewarded for big-picture thinking, the sort of strategic part and boldness. So of course, we begin to nurture those traits that get rewarded. If we’re rewarded for being precise and correct, we become ever more precise and correct and get the idea that that’s what’s going to lead us to the top or help us create a really successful enterprise. Whereas if we get rewarded for strategic thinking and boldness, then we’re going to believe that that’s what’s going to work for us.
So I think that that plays a really important role in probably honing the perfectionism that women may be comfortable with anyway or have gotten accustomed to through their experience in school and as particularly as a teenager and a child at home. So, I think that that’s really where it comes from. I don’t like to pathologize it by saying, “It’s rooted in fear.” I think we tend to emphasize behaviors that are rewarded, and I think starting from quite early in girls’ lives, being the perfect little person is a way of getting rewarded.
Melinda Wittstock: Sally, I want to go back to what you were saying about leverage and leveraging networks and get very specific about how women should be leveraging those networks. What are some key things that they can do whether it’s about growing their influence, growing their thought leadership, or whether it’s just about finding great mentors and support networks for themselves? What should they be doing?
Sally Helgesen: I think that the number one thing … I mean, especially if you’re in an entrepreneurial venture and of course that is going to be consuming, but developing your external network is always going to be key to you. So look around and try to figure out where you want to put some energy. If you’re starting a tech firm, is it in a women and technology organization? Or is it in some network for men and women that’s in a particular part of that sector? What are one or two, preferably two, good external established networks that you want to and need to, and can benefit from getting involved in? That can look like a really heavy lift when you’re also trying to start a company on your own. I think it’s good to get in the habit of doing that as early as possible.
Melinda Wittstock: It totally makes sense to make sure that you have these networks. It’s an absolute predictor of success. Once you have them, how to leverage them effectively?
Sally Helgesen: Okay, here’s what I think works. Here’s what I’ve seen works. Is be very intentional. Say, “Okay what do I … What is a couple things I’m missing? Am I missing some coaching on how to most effectively make client calls? Am I missing some coaching on how to most successfully close deals in terms of sale? Or, am I missing some level of understanding some of the technological expertise of the people that I’m hiring so that I can better evaluate. What are my needs right now? What would be really helpful to me?”
Then you look around in terms of your network. If you can identify people you think could be very helpful to you, or if you can identify people who you think might know people, or your needs might be you’re trying to prepare yourself to go to the capital markets. I mean, that’s a big deal.
Then you want to start asking the question, I’m trying to get better at this, I’m trying to prepare myself for this. I’m trying to understand this business challenge. Do you have any advice for me? Do you know anyone who might be able to offer me some guidance on this? That I could get involved with? When you make those asks, what’s important? I think what makes it sometimes hard for women, when you make those asks you want to make it also clear that you, by engaging this person as a resource, also are offering yourself as a resource to them in the future.
I think this kind of holds women back often, because maybe in their minds they’re not seeing themselves as enough of a player who could be valuable to someone that they’re asking for help. I think that’s an important sort of hurdle to under … To overcome.
To be very clear when you make asks, to say I’m asking you this, you didn’t do anything for me here. I’m really glad to help you on something in the future, and setting up these kind of … They’re not quite as transactional as just a quid pro quo relationship, but they’re relationships that are really about getting resources to flow, both in your own life and in the other person’s life.
I think getting comfortable with making those kinds of asks and requests, and if you’re uncomfortable with it, practice it. Get somebody, a friend, a colleague, somebody you trust, a coach, a peer coach, and say, “You know what? I need to get better at leveraging the people in my network. I know a lot of people, but I never ask them for help.”
I belong to a big professional network and … I’m talking about myself. When the recession really hit and I was getting killed, you know what? I never called any of those people and said, “Hey, do you have any leads for me? Do you know anybody who might, in this very difficult environment, be hiring in terms of speaking and workshops?” I didn’t do that, so I’m a poster child for some of these behaviors.
If you’re having trouble doing that, get some coaching on it, either paid coaching or not. Enlist a peer coach and say, “Hey, I’m really struggling to leverage the network I have. I have a great network and, of course, I want to keep building it, but I have trouble making the ask. I’m awkward about it. I feel like I’m using the person, so I think that comes through. I feel sort of inauthentic because it’s not a behavior I’ve practiced a lot. Can you give me some help? You seem to be good at it. Let me know how you do it.” You can ask some guys who you’ve seen who are really good at that.
What has been helpful to you? Or you could even say to somebody, “You know, I’m going to try to ask this person to help me with X. Would you come along with me and just tell me how did I do? Is there a way I could have done a better job? Did I betray the fact that I was uncomfortable? Or did I … Was I able to engage that person in a really strong way?”
I think that’s really, really important. We don’t … If we are trying to learn to ask for help, ask for help in learning how to ask for help.
Melinda Wittstock: That’s a good place to start.
Sally Helgesen: That’s a really good way to go, because whenever we’re practicing a new behavior, when we identify something that’s getting in our way and we want to practice a new behavior, getting advice from other people, support from other people, fresh ideas and fresh perspective, is always going to be the most effective way of making that change.
Melinda Wittstock: This is so true. So, Sally, take me back a ways. When did you first get interested in women’s leadership issues? What was the spark that took you there? You’ve been doing this for 30 years.
Sally Helgesen: Yes.
Melinda Wittstock: Why did you start?
Sally Helgesen: The spark that took me there, I was working in the 80s in corporate communications, a number of companies, and it just astonished me … There were not very many women who were in high positions at all, but there were women who were starting to come into the middle ranks. It just astonished me how much the companies I was working for, which were good companies, with good people in them, had absolutely no clue as to what women could contribute. They just didn’t have … So, I felt very frustrated by that.
At the same time, I was trying to figure out what I needed to learn in order to be successful. This is in the 80s. I started reading a lot of books that were being published, it started being published in the 80s for women telling them what they needed to do. Almost everything I read, and some things were helpful, but even the things that were helpful, everything had the same underlying presumption, which is women, you’re not going to change things. This is how the workplace is. Just because one half the human race enters it doesn’t mean it’s going to change. So, get with the program. Adapt the culture. If it moves, salute it. Leave your values at home. Go to classes and learn how to talk about football even if you’re not interested in it. Get out there on the golf course. Wear a bow tie, et cetera, et cetera, and this will make you a success.
I thought, “This is terrible advice. Who wants to do this, for one thing.” I mean, I happened to like sports and grew up on them, so I can talk about it, but if you’re not interested, don’t go to a class so that you can say, “Hey, how ’bout that play on Sunday?” To some guy. That’s not going to work.
I felt that women were getting very bad advice and I saw that they were being undervalued, so I thought, “We need to look at what women have to contribute.” Organizations are changing. I didn’t know how fast they’d be changing because of the technology. This is, you know, all before the internet. Organizations are changing. The leadership model is shifting. We can’t tell women to abandon what makes them excellent in order to adapt to a very hierarchical leadership model. That’s kind of going out of favor.
I decided to take responsibility for that and start interviewing some of America’s best women leaders. That’s the book that became The Female Advantage. It became very successful, I think, because there was nothing else like it. Everything else was still telling women to put on a suit and salute the general.
That’s really what started me off. I saw myself at the time as, and this is … The person who wrote the book today would really push back on this, but I saw myself as just a writer, but people began to see me as an expert because I brought something new into the world. I started doing workshops, speaking at events, wrote seven more books in the subject, and just kept with it, developed it, refined it, and had a front row seat to watching all the changes that have happened over the last few decades.
Melinda Wittstock: Isn’t it so interesting that a lot of our major accomplishments and the things that we do that are so special in the world come from a frustration, a lack of just like observing something or being affected by something ourselves, and this is so true, with entrepreneurs and the type of companies that we start, as well.
What a beautiful story, and thank you so much for going on that journey, because, apart from anything else, you’re helping so many of us.
Sally Helgesen: Thank you. I agree with you that most great products, companies, ideas, are born when one person says, “Why can’t it be done this way? Why does it need to be done that way?” And then steps up and takes some responsibility for trying to make it, you know, trying to change how it’s done.
It is very much … My experience resonates, I think, with anybody who’s being an entrepreneur which, of course, is what I became because I began selling workshops, seminars, programs, doing consulting, and then doing coaching. It’s been very much just me developing that. I can tell you, it’s not easy, but boy is it rewarding.
Melinda Wittstock: Well, you’re in the middle of the promotion for the book. I know you’ve been traveling a lot. There’s a lot going on, so even within this phase, do you know what’s next? What’s the next 10 years for you?
Sally Helgesen: The next 10, I can only think of five. The next five years, I’m going to be focused on this book, How Women Rise. I’m not looking at writing another book. I might write something that is less than a book but something that would be helpful for men who want to really help women in terms of identifying these behaviors and working with them. So, some way of better engaging men as allies. I might write something about that, but it won’t be a full-length book.
What I want to do over the next five years is I feel like I’ve been given an opportunity from heaven. I have a co-author who is phenomenal, Marshall Goldsmith, and genius marketer, whom I want to learn from. I’ve never been good at that, so I’m looking at this as my opportunity to learn how to really, really market some intellectual content property that has very big potential to change women’s possibilities. I’m going to be focused on that. I’m going to be focused on developing workshops, online courses. I’ll deliver workshops that we can license trainers to deliver. That’s what I’m going to be focused on is really building this into a nice, small, well functioning business.
We’re getting responses. My co-author, Marshall Goldsmith, and I are leaving for the How Women Rise India tour next month. We’ve got interest in doing similar things in Korea and Singapore, in Turkey. I mean, this is really a phenomenon, so I want to take full advantage of it and make sure we get it out there to the world.
Melinda Wittstock: Well, congratulations on this success. It’s so important, the work you’re doing. There’s a special place in my heart for it because it so aligns with my own personal mission and why I do this podcast and all the other summits, trainings, masterminds, and things that I do.
I think when we, as women, really fly together, right? Like, we soar higher.
Sally Helgesen: Exactly.
Melinda Wittstock: Right?
Sally Helgesen: Yeah.
Melinda Wittstock: So, really stepping up for each other, vesting each other, throwing business to each other, all those sorts of things, and helping each other; just mindful of what you were saying about networks really supporting each other. In those with big give forwards, real magic happens, so it’s an exciting time.
Sally, I just want to say to everybody, go get this book, if you haven’t already-
Sally Helgesen: How Women Rise.
Melinda Wittstock: How Women Rise. Yeah. Sorry. How Women Rise. Also, how can people find you and work with you, Sally?
Sally Helgesen: Well, the best way to find me is through my website, sallyhelgesen.com. I’ve got a contact button there so you can just pop it, get me your message, and I will respond. Also LinkedIn. I’m active there. I’d love to meet people, women entrepreneurs, and supports of this show there. I’ll be promoting the show when it goes live on LinkedIn and other platforms. So, I’m pretty easy to get in touch with and access. I respond to people who reach out.
The book, How Women Rise, is available everywhere, bookstores, online retailers, and in a lot of airports, which I have to tell you is tremendous fun reading that as I fly around the country.
Melinda Wittstock: That’s wonderful. Well, thank you so much for putting on your wings and flying with us today.
Sally Helgesen: Thank you, Melinda, it’s really been a pleasure. I love the whole metaphor of the wings here.
Melinda Wittstock: Thank you so much.