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A Guide to Succeeding as the Only Female Executive in an Organization

Posted March 28, 2024
Debe Rapson, Fractional CRO & Co-Founder of Women in Revenue, joins our host, Camela Thompson, Go-To-Market Thought Leader and B2B Insights Expert, in this episode of the Revenue Marketing Report. Debe shares some of the awkward moments as the only woman on leadership teams and some fantastic advice for getting your voice heard.

Debe Rapson, Fractional CRO & Co-Founder of Women in Revenue, joins our host, Camela Thompson, Go-To-Market Thought Leader and B2B Insights Expert, in this episode of the Revenue Marketing Report. Debe shares some of the awkward moments as the only woman on leadership teams and some fantastic advice for getting your voice heard.

Today we are going to talk about how to be heard as the only woman executive on the team. It is close to my mind. I am sure you have been there. What first thoughts pop into your mind?

“The first couple of things that I am thinking about on topic is just navigating being heard around the table. Navigating the mentality of men, suggesting that the woman is on one side of the coin is being too direct and bitchy. The second side of the coin is being too forceful and then being too emotional. Those are the things that come to my mind and working with a team of men.”

I am thinking back to all the coaching I received early in my career, squashing the emotion and focusing on data. Don’t get too passionate about things. Just focus on the facts. Yes, that is good advice. But when you’re being steamrolled, I think a little bit of a firmer tone is in order. Not yelling, of course, but standing up for yourself and saying – no, I actually meant this thing that I said— is appropriate. But it is not always looked at that way. Have you observed anything similar? Do you think things are getting better out there?

“I do think that things are getting better. I think with Trump being in office, with all the diversity conversations that happening in the boardroom I do think it’s getting better. People are more self-aware than they were three to five years ago. I think that the behavior is getting better, but I still think in many circles, it’s not. I think sexist comments are still definitely occurring in the boardroom and the executive leadership team table and there is still the old boys’ network of let’s go golfing. Oh, sorry, you don’t. Bye. There are people still talking over women, the only woman in the room, and also I’m interrupting them a lot. It is hard to tell whether that is the feeling of their insignificance or whether that is the rudeness of people talking over each other. It is something I see a lot of people doing, not listening.”

I have been guilty of butting in myself and I have a theory that many of us mirror the behaviors of successful people and the people who can be heard. Not that that is an excuse, but I think that could perpetuate that one, maybe.

“Yes. It absolutely could be and there are plenty of women who are right-brain and left-brain. There are plenty of women who are very operationally oriented and data focused. I also certainly think as a leader today, you need to harness insights from data and provide those to the team. I don’t think that it’s wrong, but I also think that it would be inauthentic to not be passionate about what you’re saying or come in strong when you believe something. Some men try to dismiss women doing that, dismiss it as they are being too emotional or it is like calling somebody a name indirectly. It’s just trying to tamp this down.”

I have been in companies where I couldn’t get in a word edgewise and I’m a talker. What I would do is raise my hand and sit there awkwardly. I would make it awkward and then the people would start to realize and create space. Are there other ways we can help people create space for one another?

“Yes. I think there are a lot of challenges to being the only woman at the table. Let’s talk about some of the strategies that women can put into place. One of them is around creating those relationships with their leadership team and their executive team. Those one-to-one relationships instill trust when you do that. You create allies who sit at the table. You create a relationship where you can say, I don’t appreciate when you do X or Y, when you talk over me, when you do this or that. Ingratiating yourself as an insider, especially when you’re coming on to the executive team. Building those relationships and trust across the table is an exceptionally important strategy to being the only woman sitting at the table.”

I’ve been lucky enough to establish enough of a bond where, not in that meeting but away the meeting, I can say, when you said this thing I knew you didn’t mean it this way, but here’s how I heard it. Can you see where that would occur?

“Or even ask them, what did you mean then? It’s great! Help me to understand what you said. It felt strange to me. What did you mean by it? Where were you going with that? I think not even assuming necessarily they have bad intent or good intent, but just understand their intention.”

Yes. I like that framing a lot better, note taken.

“This is how we learn from each other. There are so many of those sorts of moments that come up in relationships. Another one that I can think of that strikes me is when you’re on an executive retreat and everyone brings their partners and you’re the only woman. The women, the wives who are not on the team might be going and doing a thing, whatever it is and you are kind of caught in between. Which way do I go here? That is another one of those funny moments that I’ve been in.”

I knew we had a long way to go when I went to a very large summit for a marketing vendor that I won’t name. I went over to the vendor booths and there’s this big section called the women’s confidence center. It was where you can go get your hair done, your makeup, your nails and perhaps a couple of pictures taken. A lot of people don’t see any problem with that.

“Yes. I do that on my personal time, but those aren’t bad things.”

Those aren’t bad things at all, but to make it such a focal point at a conference for technology. It didn’t hit the notes I think they were going for.

“Yes. It is interesting that you bring that up. Maria Shriver sponsored a conference for several years. It was a women’s conference down in southern California and I was excited about it. This was way before Women in Revenue. I went to that conference expecting something very different than I got. She was interviewing Michelle Obama and I was excited about seeing that and seeing that content. When I got there, I expected a completely different type of conference. Michelle Obama was there, and Gloria Steinem was there, she was my personal hero. There was Oprah Winfrey. There were predominant names and I expected something that was just a little meatier content around women supporting women and just a little bit more business-focused and feminist-focused. What I got was a showroom floor of some weird stuff like measuring bone density, and a booth for makeup, hair, beauty products, and health products. I had a miss on the type of conference I expected. The content was different than what I expected when I got there and it was disappointing to me to see that.

“I am going to say that was probably twelve to fifteen years ago. When I think about the time from that even having a women’s conference made me think, oh, this cool to where we are today. There is a good amount of movement from there to here, where we are today. I do see that with Sheryl Sandberg’s Lean In Initiative which addresses some of the topics that we are talking about the bossiness and being a bitch, those kinds of things. We are coming along.”

My heart hurts for your experience because I have been there. Like I said before, none of those things are bad things. So many of us notice though that everything from obituaries to profiles focuses on motherhood and appearance. It’s hard, as ultimately, I think people want to be recognized for what they have accomplished in the workplace.

“Absolutely! Particularly if you’re both a mom and a career person. I am both. I did something that most women weren’t doing when I was rising up in the mid-nineties. I got married. I married for love and not for income. I married a high school teacher and I was going to provide the bigger income in the family, but I struggled a little bit. I also wanted to be a mom. I wanted kids and so I had to figure out a way to have my cake and eat it too. I stayed in selling which is naturally a great fit for me. I was one of the first women that I had ever met who worked out of home, full-time.

“From basically those months of being pregnant through raising my children, and even today, I worked virtually out of my home. I remember walking away from job opportunities because the person who was hiring me wouldn’t allow it. I also remember one of my favorite CEOs, Chris Golich, who was a founder at Demand Base, said to me, if you would be willing to come in once a week, we can make that work. I said I’ll make you a lot of money that way. We figured out a win-win situation and I did that. It was a great eight-year relationship and run. I did that throughout my career. I had the opportunity to raise my kids and also have a full exciting career where I traveled. I had a partner who was willing to be a real partner to me and I back to him where we could create something that would be a win-win all the way around. I didn’t want to miss my kids growing up and childhood and to be their mom and be engaged, but I also was driven in my career. And back then, women weren’t doing that. They were going into the office or they were choosing not to work. I had the constitute to decide, I am going to stick to it, but it was a tough thing back then. I smile all the time as COVID-19 changed all of this for women.”

Yes. I like how the change has stayed in that people are apologizing for things that they shouldn’t have been apologizing for in the first place, their dogs barking in the background or something.

“Exactly! Do you know that every year Women in Revenue does an annual survey? We’re going to be releasing this year’s installment in the spring so look for it on social media. One of the interesting outcomes from that survey is that the #1 and #2 things are flexible work. So being able to work from home and flexible hours for women were the top of the list. Then also not only equal pay, but having insight into transparency around pay. Those are two things that were so important last year when we surveyed the Women in Revenue community.”

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