Challenging the Status Quo: Why Demasculinizing Leadership Matters

Deborah Streeter is the Bruce F. Failing, Sr. Professor of Personal Enterprise and Small Business Management in the Charles H.Dyson School of Applied Economics and Management at Cornell. Much of her teaching, research, and outreach activities focus on small business management and gender issues in business and entrepreneurship. In 2017, Deborah launched the Women in Leadership certificate, an online program designed to help women achieve their leadership goals by providing them the skills and knowledge to overcome gender biases and the double-binds inherent in the business world. We had a chance to sit down with Deborah to discuss the origins of her leadership course, the importance of role models, the pitfalls of perfectionism, and the power of persistence.




Thank you so much for taking the time to speak with us. Let’s start with how you first became interested in the topic of women and leadership? 

DEBORAH: I came up in a time when feminism was very strong; I’ve considered myself a feminist since I was in college in the 70s. But as a teacher at Cornell in the mid 80s, I didn’t see feminism as feeling relevant to a lot of young students, and I wanted to understand why fewer women were in the entrepreneurship classes. When I started getting experience and interacting with a alums, I saw these very different divergent pathways for women as compared to men. I started following research about women in business and thought, ‘my gosh, things are really stacked against us as women,’ both in terms of institutional structures, which are mostly mostly built around white men’s lives, and also from the psychological side. Both men and women carry expectations and unconscious biases about women and work – consciously and subconsciously.

Was this the seed for your Women in Leadership certificate program?

DEBORAH: Absolutely. I’ve been teaching a course in leadership for 20 of my 30 years teaching now, and eventually, because I’d been collecting and reviewing literature on the topic of women in business for so many years, I started thinking about how I could put this to practical use. I wanted to see how we could look holistically at young women’s futures and consider all the aspects of life and work that impact their careers, personal decisions, and turning points. In 2017, I launched a certificate program for women in leadership offered through the Institution for online learning at Cornell. The certificate is aimed at women who are fairly early in their careers, and my goal was to give them some tools, ideas, knowledge and encouragement so they could be more proactive and successful in overcoming hurdles in their careers. Now we’re working on the Advanced Certificate program for women who are more experienced. I know there’s still a need for tools and support at that level, because there are a whole new set of challenges that women face once they’re well into their careers and in positions of leadership. Our goal is to find out how institutional and structural changes can be made to help not only women, but everyone.

You say the odds are stacked against women in the business world. What specific issues stood out?

DEBORAH: In the 70s, 80s and even in the 90s there wasn’t enough of a pipeline for women for women to reach top leadership roles; now, in the corporate world at the entry level, women are getting as many entry level jobs as men. However, what happens is that the pipeline is super leaky, so by the time you get to the CEO positions, women only make up about 5 percent at the top 500 firms. The same thing is happening in entrepreneurship. For a while, there weren’t as many women starting businesses; the pipeline was very small. That’s changed immensely in the last decade, and it may be the case that there are actually more women than men starting businesses, which is wonderful. But again, the same structural and unconscious biases present huge challenges for women, which seriously impact the success of all of these blooming new entrepreneurs. These challenges could be the structure of life for women with families or other major care commitments, or a lack of financial support and networks. A lot of factors come into play to create very different realities for entrepreneurial men and women. What’s happening in the entrepreneurship world with regards to women is very distressing because we’re so underrepresented in the venture world. Women are starting businesses today but they tend to be underfunded and not set up for success.

What, in your in your opinion, are some of the key traits or characteristics of a successful entrepreneur? How can we set women up for success?

DEBORAH: There are some fundamental things needed for both men and women to start and run a successful business. Have you identified a problem or desire and a solution that fits? A lot of entrepreneurs don’t actually get out there and validate their ideas by having customer conversations. After you find your solution fit, you need to make sure that your product fits the market and build a scalable, successful business. Then there are two other two issues: cash flow, which can kill you early in your business if you don’t have a strategy in place, and the need for a great leadership and management team. If you solve the cash flow problem but have bad chemistry in the management team, you’re going to stumble. I think those things are equal for men and women.

When it comes to what can help women specifically, I think we as women are socialized to tend to relationships and to be collaborative, and so we should have some advantages in building and managing a team to take a company forward. Where we run into issues is our networks; they’re far smaller and fewer than men’s networks because so few women are in leadership roles or positions of power, so there is less access to capital, expertise and mentoring than in men’s networks.

I also think persistence and grit are important, especially for entrepreneurs because they are always getting feedback from the market and some of that feedback can be very discouraging. I’ve looked at some of the research on how women and men deal with feedback and it’s really interesting. Women tend to feel more of a responsibility to respond to feedback than men do. One study I looked at traced this back to elementary school where the school structure revolves around the way little girls tend to operate, which is sitting down and concentrating on something. Boys get yelled at more in elementary school because their learning style is very different, so from an early age boys start learning to tune out feedback and to rely on their own judgment instead. This is just one theory, but it could be part of why women are more sensitive to feedback. When you’re in an entrepreneurial setting it’s tricky because you can’t ignore feedback from your customers, your suppliers, your employees or your partners, but you have to filter some of it out so you can navigate the inevitable ups and downs; you need to be able to hear and trust your own judgment. The entrepreneurs that I’ve watched go from college to very successful careers all have the ability to navigate that. It’s interesting to think about how a boy’s life could better prepare him to follow his own assessment, and how a girl’s life teaches her how to listen and respond to others more so than her own reasoning.

What do you think are some of the big picture differences that women and men face when embarking on the career track after school?

DEBORAH:  I mentor a lot of undergraduates and there’s a big difference between the concerns and perspectives of women and men when it comes to their career trajectories. Girls are thinking, ‘I’ve got this time period of about 10 years from when I graduate to build and establish my career,’ so they feel pressure, far more than boys, to figure out their story – and quickly – because by the time they reach their early 30s they expect to be getting married and maybe having children; they’re already seeing their careers within a short window of time.

Boys, on the other hand, are thinking more along the lines of  ‘I have 20 years after graduating to figure out my career.’ Boys feel much less pressure in terms of a timeline to figure it out; they give themselves more leeway to throw away a few years, maybe trying a business or working at a small company, or even just chasing startups on the west coast. Boys’ risk attitudes are shaped differently because they’re right – they could be 40 and still get married and have a baby. For women it’s not the same.

What that means overall is that women lean back. When I hear women say, ‘I think I better take a corporate job because I’m probably going to have a baby,’  I ask them, ‘are you pregnant right now? If not, then why make decisions for a future that may not even happen?’ What you want to do is have the most options, the most power and the most experience at a time when you think you’re going to need flexibility. Life can introduce surprises at any time; there are lots of things the universe could serve up to you, so why not take your most promising opportunity right now rather than the one you think would eventually fit into the life you’re imagining for yourself?

On the topic of women and confidence, what is something that your research has shown is key in helping women build esteem and shift away from external validation to inner authority?

DEBORAH: I think one of the most important things that can help build confidence and belief in their own capabilities to follow their dreams is having role models. We really need to make sure that women and girls see themselves in the success stories that are told in the world in general, but also in business and leadership roles. There’s a saying: if you can’t see it you can’t be it. That’s why I make sure that I have at least as many or more women than men as guest speakers and features in videos case studies in my business classes. I think that’s probably one of the most important things to look at in why we have this big decline in women who are in computer sciences – it’s because women stopped seeing themselves as a part of the industry. For example, when video games came out, all designed around boys’ interests, women started disassociating from that field. Every field is equally full of opportunities for women as it is for men, but if you never see yourself there, if you look at all the tech leaders and all the venture capitalists and every single face you see is male and usually white, you realize you’re trying to enter a world you’re not part of. We need to reveal the rich cases that do exist because there are many successful women entrepreneurs in every field, we just have to exhibit them and amplify their voices.

We also need to have role models who talk about failure. I’ve done more than 700 sit-down interviews with entrepreneurs and experts and I’ve struggled to get anyone to really talk about failing. We’ll talk about it generically like ‘oh yeah, failing is important – if you’re not failing you’re not trying,’ but when I ask them to give a specific example from their life, they don’t talk about it. I think that kind of honesty is key because we can’t set up women for success if they don’t know how to deal with failure – and that goes for men as well.

What else do you think needs to be redefined or re-examined to tear down systemic inequities?  

DEBORAH: The world of business is very very masculinized. For example, if you put in the search word entrepreneur into Google Images, almost every image that comes up is male; if you search leadership experts, almost all of them are men again. So there’s a barrage of messages that to be strong and powerful and successful is affiliated more with men than women, and it’s threatening to men if women exert that much right.

I’m working right now on the Advanced Certificate program, specifically on a negotiation course, and the research is stunning about how women pay more of a social cost than men when they negotiate in a tough and aggressive way. So we’re not crazy; we actually do get signals when we try to negotiate in a man’s style that it’s not appropriate or acceptable behaviour for women, which equates to power not being appropriate for women. So there’s a whole double bind: being nice and being collaborative are not affiliated with power and strength, but women have to have both to be successful entrepreneurs – you have to have people skills and you also need to be able to make difficult decisions and to be aggressive. But every time we step over into those stereotypically masculine traits are we to have our hand slapped for not being nice? So we must build up our resilience. We need a team or network around us encouraging us to go ahead and do it all, be caring and strong, be compassionate and opinionated, listen to others and take care of yourself first, because there’s a lot of pushback for women who express strong leadership. We saw that in last year’s U.S. election – every time Hillary Clinton said anything slightly aggressive people treated her so much differently than her opponent who was (and is) so often mean-spirited, aggressive, and untruthful.  This so-called unconcious bias (held by both women and men) is the undercurrent that hurts women when it comes to status and leadership.  We have to cultivate an awareness of these biases and make sure they are not influencing decision-making.

What are some of the ways that we can make the business world more inclusive of women, or how can women overcome this double-bind?

DEBORAH: Language makes a big difference. When Google realized how out of balance they were on gender equity, one of the things they did was rename their conference rooms – previously they were all named after famous men, and now they include women’s names. If you walk into a place of power and everything you see is sports and race cars and things that are iconically male, you’re not going to feel like you belong. Language and imagery matters in creating an inclusive work environment.

Navigating the double-bind is this annoying combination of having to be persistently pleasant but also persistently persistent. The #MeToo movement that’s happening is fascinating to me; it’s the first time in many years that I’m like, “wow! Women are really starting to say ‘what the heck?’ again.” I think this new wave of feminism will include a redefining of some very basic ways that women and men interact. Hopefully it redefines things so that it’s ok for women to be powerful, to express ambition and express desire, and to really achieve at the highest levels. It’s going to take a lot of comradeship among those of us who believe in this, and it has to be inclusive of some men – it’s not going to happen if only women are involved.

Could you sum up your thoughts as to what women can do, right now, to help them succeed in their lives and careers overall? 

Deborah: In the end, I’d say that the best thing women can do is to work on their own inner critic and find ways to manage the imposter syndrome they may have as they push into a world that’s male-dominated and may feel foreign to them. Get comfortable with being ambitious and learn how to negotiate.  Women need to keep building up the emotional intelligence that they’ve already been socialized towards – which puts them ahead of men in some ways – and build up their approach to failure. Build all those tools so that you can ride the waves more successfully.

Connect with Deborah, learn more about her work , and take her  Women in Leadership Certificate Course.

Mara Munro