Kelley O’Keeffe - Closing the Entrepreneur Gender Gap

Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Now today's guest is Kelly O'Keefe. She is the founder and CEO of Empowered Engagement, which is a sales consulting agency whose mission is to support female leaders in business by assisting them with sales and revenue growth. Kelly's background includes working with technology firms like IBM and Gartner, but she recently left the corporate world to start her own business when she was having fertility issues, which she is really open and honest about throughout this entire conversation, which I felt really enlightening and refreshing.

You know, she talks about her background and where she got her entrepreneurial genes, but then we dove into elevating women in the workforce, specifically in sales, and all the challenges and benefits that come with it. Now you all know I'm a huge proponent of women in sales and doing everything I can to get the bro culture out of this profession so we can attract more diversity. Kelly shares some very tactical advice to help women and men create a more diverse and effective sales order, which more people need to know about. Now look, we have a long way to go, but hopefully conversations like this will help keep moving us all in the right direction. Let's make it happen. Kelly, welcome to the Make It Happen podcast.

How are you doing today? Hi, I'm well. How are you? I'm doing fantastic. I'm actually just back from a trip to Alaska, so I'm back ready to go. Oh, wow. What part did you go to? My mom, so my mom turned 80 and her gift to us as a family, my sister and myself and both of our families was a little cruise to Alaska out of San Francisco. So we took a 10 day cruise straight up to, we started in Juneau and then we just, we took two days to get up to Juneau and then come down the coast and then came back. So it was Alaska's, have you ever been to Alaska? I have, I have a cousin who works for Alaskan Airlines. So I've been out there to visit her, but I've heard the cruise is just incredible. That's on my bucket list.

It's one of those things. I mean, Alaska in general, as you know, it's like one of those places you can't really, pictures don't do it justice. It's one of those, like you have to kind of, you know, being next to a glacier or being standing on a glacier, like you can't take a picture and explain that. So it's, the experience was killer. So you got to, you got to see them while they're there. Yeah. Well, my wife's an environmental scientist. And that was actually part of the depressing part of it. Cause like you'd be on the, you'd be on the iceberg and they'd say, well, yeah, you know, 10 years ago it was all the way down there. And it's like, now it's here. And it's like, ah, shit. Yeah. Wow.

Well, that's amazing though, that you got to go see that. That's awesome. That was fun. Cool. So we're going to get into a bunch of stuff today, but why don't we give the audience a little bit of background and some context of where you're coming from, Kelly? Cause we're going to dive into some really important and I think very interesting topics right now. Let's give some context of where you're coming from. Sure. Yeah. So my name's Kelly O'Keefe and I am a former tech sales exec. I led a team of over 300 sellers globally. I'm in my last position. I've worked for a variety of large global tech firms. I primarily work for firms based out of the San Francisco Bay area. I live in Atlanta now. And I left corporate last September because I'm on, as you know, I'm on a fertility journey.

And so that really affected my body's ability to work certain hours. And so I made a conscious decision. I, I had taken some entrepreneurship classes in my, my MBA program and I really had always wanted to start my own firm. And so I thought there's no time like the present. Um, why not go through fertility treatments and start a business at the safe? Um, so yeah, I started, um, a, a sales really bootcamp for, for women, female business owners that maybe want to sharpen their sales skills or don't have a background in sales. Um, and so we go through a quarter long intensive program and sharpen them up and make sure they have a clear path to have a clear path to revenue and it has been the most rewarding thing I think I've ever done.

Um, so yeah, I mean, that's really, that's really it in a nutshell. Um, I'm, I'm staring 40 in the face. I'll be 39 next year. So, you know, I've had a good, um, solid 15 year career in corporate sales. Um, and you know, have, have transitioned to now coaching, um, startups and their founders. So I'm really just navigating entrepreneurship now, but, you know, flexing my sales skills in a different way, I guess you'd say. Well, now let me ask you, I always love to kind of get even, even go back a little bit further. Cause that entrepreneurial gene sometimes is in us and we don't know it right until it's scratched. And then it's like, oh man, this feels so much better than it, than, than what I was kind of felt trapped in.

Looking back and like growing up, right. Did you, were your parents entrepreneurs? Like how, where do you think you got that, that itch to, to have the confidence, if you will, to go off on your own, first of all, but also that, that entrepreneurial spirit. That's a, that's a good question. I've actually never been asked that before. Um, and it's making me think a little bit. So I came from a very, um, frugal family. Didn't have a lot. My parents didn't come from much. Their parents didn't come from, from anything. And so I think there was a level of scrappiness there. Um, my dad had a, a side hustle before they were called side hustles. Um, he would rewind electric motors, um, on the side. He was, um, you know, a tinkerer and, and very, very smart.

And so he would do that. But again, we didn't have a lot, right. Um, it kind of helped us keep the, the needs met there. Um, and my parents got divorced and my mom went back to school. Um, trying to make more money, right. Like trying to get a job that was like more nine to five. Um, she was a night nurse at the time. And, um, but you know, I think seeing my, my dad work on the weekends and at night with his kind of side business. And then when my mom remarried, um, she remarried an entrepreneur. Um, and so I kind of saw that happening. Right. Um, and then actually, and, and then when I got to be about 14, 15, I started babysitting and this is, I've never told anybody this before, but, uh, my stepdad helped me make these little business cards and, and I started, uh, Kelly's kid sitters.

And I babysit for the neighbor, the neighbors, right. But I would like leave my little cards on their counter and they would just crack up after, I'm sure. But I needed the money to, to be able to get a car and to, to do stuff like that. So I think that, yeah, I, I did see a model of, of going out and getting, creating your own kind of, um, source. I think that's, it's funny because I, I usually there's two angles to it, right? It's, it's the kids who watch their parents basically wither and die in a nine to five worlds and realize that that is not something I want to do with my life or the parents that were entrepreneurs, but we didn't call it entrepreneurs back then. You know what I mean? Like my parents are, you know, my mom's 80 and, uh, you know, they were both entrepreneurs, even though they would have never called it an entrepreneur back then.

Right. Like my mom, for instance, like when I was, my, my sister's nine years older than me and I was a happy surprise. Uh, my mom will go to her death cell telling me that, no, we wanted you here. And I was like, yeah, I'm not having a nine year old daughter, by the way, I came to her when my daughter was nine. Right. And I said, ma, I, I know for a fact now that I was a happy surprise and you didn't plan me. And she's like, why? I was like, cause my daughter's nine right now and you got a better shot at seeing God than me having another thing right now. So needless to say, but what happened was my, she was, she was there for my, my sister. So she was a stay at home for mom, for my sister. And then she got a job and she got a job at a really cool, like, uh, Wang Laboratories, which back in the day was like Salesforce is today.

Okay. Great job, high paying, all the things. And when, when I was born, she wanted me to have the same experience as my sister did. So she literally quit her job, uh, at Wang and she started her own consulting practice at home and she was a, she was a, uh, uh, helped people get jobs. Uh, so she was a career consultant. And so when I would come home, I would walk into the house and we had a split level and, and, you know, on one side of our living room was my mom's office. On the other side was the TV for our living room. And so, and my dad worked out of the house too. He was a contractor for the FAA. So again, not traditional quote unquote entrepreneurship, but both working from home, both kind of charting their own path.

And I didn't even, I didn't even realize it. And when I was, when I got into the corporate world, I just, something didn't feel right to me. You know what I mean? I'm like, this, something's not right. I don't like being put in a box. I don't like being told what to do. And then when I got into startups, it was like, oh my God, like I can stretch like this is. Yes. Okay. Like now my, my, and that's why I think I love sales so much is because it is a direct reflection of your effort, right? It's like, I just didn't, I never understood like in a salaried position, if I worked harder than that person, why am I not getting paid more than that person? If my results are better than that person's, why are my, why are they getting paid the same amount as me?

In sales, that answers, right? So, so with, with you and your, your mission now, so what is your mission? Let me, let me, let me start with that. Cause I want to back into the mission of, of what you're doing right now. I could, I could infer what it is, but I want to, I want to hear from you what your mission is. Yes. Well, helping more women sharpen their revenue generation skills. So right now there's a huge gap and we saw COVID really highlight this with the great breakup, but so many women, if you look across the typical functions of a company, marketing, legal sales, you, you typically see about 30 to 40% of that mid-level, we'll call it, you know, VP level in those organizations across legal, HR, marketing, et cetera.

Usually about 30 to 40% of those roles are held by females. So almost equitable, almost. Yeah. Kind of. Sales. It's like almost 20% are VPs of sales or female. And when you look at that, you go, huh? Because what puts someone on the track of coming an executive is really, you know, being able to manage a P&L or have that experience of like owning their own number and owning their own costs. Well, you know, if you're going to go run your own company, having that prior experience is great, right? And when you look at women, not only 20% of us are making it to that, you know, mid-level rank where we're owning a number, owning a P&L and really generating revenue, not only are, you know, we not, I think if you're generating revenue, you really have a voice that people listen to, you know, in a company, if you're bringing in some big bucks.

And so, you know, we're not, we're not self either. We're not self selecting into those roles or there's a breakage point. And I believe this breakage point, this talent leak, as I call it, really has to do with just the familiarity of women and revenue on both sides. Whether it's women, you know, having imposter syndrome, being exposed, seeing yourself in a revenue generating line of work, identifying with that, or, you know, and just in a company seeing authoritative, you know, folks, positions of authority driving revenue just don't, aren't typically associated with feminine qualities. And so I think that, you know, the definition of, um, you know, when we look at female entrepreneurship, especially less than 3% of venture funding is going to female founded firms.

Was it that bad? I knew it was bad. It's not even 3%. 3%? It's not even 3%. And so I'm thinking, okay, if I were a venture capitalist, you know, I would want to really make sure that the folks I'm giving money to maybe have that experience managing P&L, or maybe, you know, I have that credibility. There's a lot of women out there that do. However, you know, we're in a position as women where if we don't help each other and we aren't conscious, have allies like yourself, help us sharpen these sale revenue generation skills. How are we going to get more venture capital funding? How are we going to start our own firms? And guess what? We may not want venture capital funding. Right. I don't. So if we can't generate it on our own, you know, so it's really my mission.

I've spent 15 years in sales and I, I believe God put me in this role and give it, gave me these opportunities and experiences to be able to help women because when COVID hit, we saw exacerbated need for women to have flexibility control over their schedules. And that's been a power struggle in traditional office settings and, you know, really trusting women and trusting people with the credibility to make their own decisions on their working hours. And so if companies can't come around to that or aren't able to come around to that, then really, you know, there's even more ammunition for a lot of women, especially mid career women that are in there, you know, whether they're having kids or taking care of elderly parents, need to have control over their time while making a decent living.

So we're seeing, you know, obviously the rise of entrepreneurship and we saw a huge break during the great breakup. And I believe that that's really the defining factor of our generation is women being able to have control over their time and money. And I think that's interesting that you bring that up because, you know, it, it, it, it's kind of sad that it took that to, to, to shake everybody's acceptance of flexibility, of schedules and those types of things and not realize that it was needed beforehand for various reasons, not just for women, but for everybody else. But I think, you know, I'm a big fan of Matthew McConaughey. Uh, have you ever read his book, uh, green lights? Yes. Yes. So actually, have you listened to it?

I have actually. Yeah. I just listened to audio book. It's, I mean, it, but the concept is, you know, the green lights, right? Like I think I've, I've changed my opinion on this because I used to say this and I, I feel bad that I did. Cause I think it's insensitive that everything happens for a reason, right? Like, I think that is an extremely insensitive thing to say, because if you say to, you know, the, the, you know, woman in, uh, Ukraine, whose baby just got killed by the drones, like everything happens for a reason. Like that's an asshole thing to say. Right. You tell me my dad died for a reason. I'm going to punch you right in the mouth, but I do believe if you look hard enough, there's a silver lining, green light to almost any situation.

And I think a lot of, there was, there's a lot of green lights, a lot of silver linings to what happened with COVID. Cause it kind of woke us a lot, a lot of us up to the fact that, wait a minute, we don't have to go through the motions here. We don't have to force everybody to do this. We can trust people to be effective. And, and thankfully it sounds like that that's had a, even, even exponentially more benefit to, to women just from a realization standpoint from organizations. Is that, is that what you're seeing? Yeah, I think it's, um, it's kind of been a double-edged sword. Um, in one vein, you know, I have personal contacts and friends of mine that are female that are, you know, in the sandwich generation and they're going, oh my God, Kelly, they're telling us that we have to go back on Tuesdays and Thursdays.

I don't know how the hell I can make it in on those two days. Now my other days of the week, I could finagle things and make it in. Um, and you know, I, I realized that folks that may come from maybe a generation or a way of working that, you know, they want to see people in the office and they think there's something, you know, traditional about that. And they had to do it when they were coming up. Why can't it? Things are different now, right? We have a 24 seven availability. Folks are pinging us all the time. Peers are dealing with all sorts of different things they didn't have to deal with. That's if you even have ability to take your good day care. So anyway, I won't go into the long list of things, but your point about, you know, it not just affecting women is absolutely, um, you know, correct.

I totally agree with that. And I want to be clear that, you know, I'm definitely an advocate for equity and not just women are just one group. I think folks that, you know, um, are marginalized in any way. And I, I, after going through fertility treatments, I have a totally new view of anybody taking hormones. If they're on any part of the gender spectrum or if they're transitioning or whatever, nobody's going to choose to take hormone. But that's a whole separate conversation. However, I, I definitely believe that we were faced with a double-edged sword because we were, we were sort of forced to either do things the way the company, you know, company structure, um, wanted us to, to do things or, you know, um, we had to go reinvent and forced, you know, to kind of find our own, um, way of doing business and bring in income.

So, um, yeah, I think that's, but I guess the good news these days is that I think there's more opportunity, there's more opportunities than more choices, right? Because the ability these days, I, it's no longer, this is why, you know, one of the things I know my wife and I are going to have an argument with when it comes to the, when it comes to my daughter going to college, because I just, I don't believe our education system right now is educating kids with the tools that they need to be successful. And I'll be damned if I'm going to go, you know, spend three, $400,000 to my daughter to go get a $40,000 a year job. Like I'd rather give her $300,000, let her start five businesses, have them all fail miserably in four years because she'll come out with such a better education on that.

And so I think the good news is, is that there are a lot of opportunities, but how do you, I guess, how would you encourage, I mean, we can, we can circle back to sales, but staying on the entrepreneurship piece, um, there, how do you encourage women to think about entrepreneurship and to take that leap, right? Because a lot of them have additional responsibilities that somebody like me, you know, a guy like me doesn't or whatever. So what, what, what advice do you give them to say, Hey, you're, this is how you can be ready to do this, right? I mean, outside of having a really strong partner that, you know, help support you and all those different things. I think that's all important, but there's so many variables that get in the way of women taking that leap.

So what advice could you give them to start to go down that journey to figure out if that's really for them? Well, I'm certainly not the all knowing person here and any advice that you give, I would certainly love to hear as well. Um, for me, it really had to do with, and, and what I tell women is along the stop, the realm of lifestyle creep. So when we get in those comfortable jobs and the salaries flowing and things like that, we tend to, you know, especially I'm seeing it in my peer group. Like I said, I'm 39 and, you know, we see the keeping up with the Joneses and the paying more for, you know, big houses and all that good stuff. If you can try to avoid that or get your lifestyle down to where it's, you know, not that you can't, you know, have a lavish lifestyle.

Of course, we all want that. Right. But for me, flexibility trumps material things. And so if you can resist that temptation to expand your lifestyle and make those financial commitments that maybe aren't absolutely necessary so that it gives you flexibility, that would be amazing. Now there's never going to be a great time to do this. I think it's all in how you frame it. And for me, it was like, all right, well, I know that something needs to change in my lifestyle. I've got to design my life so that I can bring in an income while I'm, you know, have control of my time, I thought about maybe going back to school, the loans that I would take out for that. And I would probably not make more or I'd probably be making less than I was in tech sales.

Let's be real. And so, you know, I was like, well, I've always wanted to start my own business. I could start my own business. And even if I fail, it would be cheaper than going back to school. That's what I say. That's what I'd rather get my daughter $250,000, let her fail five times. It's way cheaper. Now, I'm not saying I didn't get benefit out of my MBA. That was an incredible experience. But I do really think there's a void in the market for sales. And that's why I created my program. But not to like plug that, but I'm just saying like, I really do think that starting your own company is like, I totally agree with you. I think it's like grad school. I think it's like going to school. I think it's just no one in this day and age, if you go try and start a company and maybe it works out, maybe it doesn't, and then fall back and go get a go work for somebody else.

It's I think it's a feather in your cap, to be honest. And I've totally heard that from so many, you know, sales leaders and executives that we want entrepreneurial mindset at our company and what better way to prove that? And I think that you do gain such a, just so many, such a good perspective of creative ways to generate revenue and how much, you know, to spend on what versus something that you don't get when you're in the corporate mindset. So I do think it's an asset. It's just how you frame it. So just jump and figure it out. Well, and I think, but sales is the great transition to that, right? Because this sale, you know, I mean, I've always said, if you know how to say, I said to my wife when I went to, when I was going off on my own, I go, honey, if the worst case scenario here, okay, absolute worst case scenarios, if I fail, I'll just go find a job at some corporate, you know, and tell them to give me a territory and get the hell out of my way and I'll make three, $400,000 a year.

That's the worst case scenarios. Cause if you can sell, you can always put my food on the table. And, and I think that's, you know, even for me, these past few months, they've not been easy, you know, like Q1 was an absolute disaster. Like the, the SaaS industry, which is where my business is completely tanked. And so I, you know, and I've always sold as a CEO, but I wasn't like, I stopped like hardcore selling, right? Sure. I had to hardcore sell and got myself back on, got the company back going, everything else. But if I didn't have that skill, I'd be in trouble. Right. So I think. It's like a risk aversion. It's like, you can hedge your bets. Like you, you know, you know, well, well, I know.

I can, I can sell. So if I go out on my own, like, I know I can sell. And, and I don't know about you, but like motivate, I've always, I would always be scared of taking a, not a fully commissioned job. Right. Like I was for my entire career, I'm a, I'm, I'm a risk taker, but not like a risk taker. Right. Right. And I, and I always said like, Ooh, I always have to have a base salary. Cause just in case, like, what am I going to do? Right. And then one day my, we all got fired and I started this company. It was just, I kind of woke up one day and I had this company and I was like, I realized I was a hundred percent commission rep now. And I was just like, and look, I'm a pretty motivated person, but you need some extra motivation.

Realize that when you wake up in the morning and you don't go to work, you ain't get paid at all. Like it'll get you out of bed a little bit earlier. Right. And I'm guessing did that, did that same thing kick into you? Hell yeah. I mean, every day, you know, you're constantly like, am I going to go spend the $6 on coffee? Well, how much more productive is it going to make me today? And it's like, the upside is way higher though. Um, and I, you know, I have one, I'm lucky because one of my really good friends who I used to work with, um, at a tech firm that I, I used to work at, she's a mindset coach. She studied neurology. She studied, I mean, she's, she's fantastic. You got a doctor, just really helps me frame, like focus on, and, and I'm, this is also like, I deal with anxiety a good bit.

And I think a lot of, especially, I think, well, we know rates of anxiety are just so much higher now and they've traced it back to gut health and all the different things, childhood trauma that we all went through and all that good stuff. But, but especially mid-career, I find that, you know, we're, we're really, it just have more, this anxiety is bubbling up. We didn't have it as much as our twenties, whatever, speaking on a whole. Anyway, I'm a high anxiety seller. And so I always was like, I need a plan. I'm a planner. I like to have a plan. It could pivot. It could, it could move, but like, I need to know, I need to focus on the activities and my goal. And so when I took away, when I take away the revenue number, like I'll, I'll keep the revenue number as my goal.

But like, I translate that into like, I'm big on conversion rates. I'm big on the data, the analytics. Like I'm big on the numbers because I like to know exactly which activities will convert to revenue. And that to me takes away my anxiety about sales because I know exactly what I need to wake up in the morning, grab my coffee and go do. And then I make it fun and I enjoy it. So I think like, that's really, if you can have a solid framework and plan, even if that plan may change, to me, that's like the safety net because you're, you're going to always have that pullback on. Yeah. I think that's, that's when I ask people and I'm curious for you, you know, there's people ask me, well, John, I'm thinking about switching a job.

You know, I don't know. I'm not happy right now. And my asking, my, my question is always, what's your plan? And they're like, what do you mean? And, and, you know, I always used to roll my eyes at the, the question of like, you know, where do you want to be in five years? Right. Like the interview question. Cause I was like, oh, you want to be a manager or whatever. And I used to think it was a dumb question, but the question isn't really anymore about that company specifically. It's lifestyle. Like, where do you want to be in your life in five years and picture what that looks like literally. That's so brilliant. And then, and forget about job for a second, forget about money for a second, but just picture what it looks like right now, based on that back into the money you need to make and therefore the job you need to have.

And therefore, if this job is helping you get to, is this, if this job currently is helping you get to that next step, that's going to ultimately get you there, then go, then stay there and grind it out and get to that next role. But if it's not, then go find something else. Because I'd say people all this time, I could eat a shit sandwich, right? But, and I'll, I'll be the janitor if you want me to. I will literally clean the floors if that's going to get me to the next level. But if I don't have a plan, I'm just going to go looking around for better tasting shit sandwiches. And I'm just going to be constantly in the house. Right? And so that plan is critical. So I think you, for you, did you see the lifestyle wise where, where you were kind of like, wait a minute, this isn't what I want.

I want, I want something different. Did you envision that? Well, for me, it was like, I, I, yes, I mean, I'm, I'm big on visualization. Yep. So, you know, I definitely was like, look, I, I, I had always known when I married my husband, it was like, look, I know I want to either, I, and I, I couldn't verbalize, verbalize it at the time, but I said, I want to be able to work part time. But what I really meant was I want to make good money and have control of my schedule because I like to work. It's not that I only want to work two days a week or whatever. I, I just need to, I want to be able to pick my kids up from school. I want to be able to have those meaningful moments. Um, and what I found was, and so when I hit that brick wall, my company was going through an acquisition.

It meant a lot of additional, um, work on my plate at that time, right when I was trying to conceive for the third time and my doctor had been like, you know, game on, we're pumping you full form. I was like, this is really, and I was, you know, I was, but so it was really like a, a, you know, a divide in the road I had to pick. Gotcha. Um, and so I thought this, this is my time that I need to job. Um, and so I did it, but you know, I, after 15 years and you know, you go through acquisitions, you go through changes and, and company priorities and every year they give the spiel of, you know, where this is our company direction and somebody gets fired. And so you have to like, you know, change and redo everything.

I'm not, I'm an ENTJ personality type. And I've been told that that's a very efficient, we, we hate waste. And so I really got, and this is no certain company or anything. I get the strategies have to change, but I got sick of like my territory changing or this changing or that changing. And as soon as I got liftoff and I was really making good traction, then it was like, okay, you've got to redo your plan based on this updated strategy. And so I really wanted to be in control of the strategy and make my own decision on if, you know, and I, and I also wanted to create a body of work that I could build on that wasn't wasted. Um, and so even though there's things that I'm doing that may not resonate with my audience and I'm going to have to pivot, I'm learning from all of that.

And that's not wasted. It's not just in a black hole. I love it. So let's talk a little bit now about organizations and diversity within organizations. Cause you know, I don't think enough people understand the impact that diversity actually has on organizations. Um, could you talk a little bit about, you know, I don't know the stats and maybe you do, but you know, the power of having a diverse org and what it, especially from a sales standpoint, because I think there is the bro culture in sales. You talked about totally 20%, I mean, 20% leadership. I would say that, and I've heard statistics about how women get into sales, but then get out of sales because it's just like, nope, this is too much of a bro culture for me.

And then it ends up being a homogeneous environment. And in that environment, you don't get the creativity. You don't get the different ideas. So could you talk a little bit about the benefits of diversity specifically related to women? And then we'll talk about how to attract, retain, and foster that. Oh, yes. I'm actually writing a book on that. So I'm very excited. Wow, perfect. Um, yeah. And I love that you said the diversity because that's really where we're going to hit the, um, the apex of brilliancy or the, you know, that's, it's not, let's make it a feminine culture or let's make it, you know, less of a bro culture or we've, we need the diversity of thought to be able to think in different ways.

And that's where, that's, that's really how we will improve profitability, improve GDP. I mean, the money, the stats show it, the research is there in terms of when you have diversity, um, of gender in your leadership, you will be more profitable. Um, and so I think like. The benefits there go beyond finances as well. I mean, the finances are one, they also spill out into the community and outside of business. But if you're just talking about within the sales team, you know, personally, I, I thought I liked the bro culture. I started out in tech sales. I thought it was fun. I didn't have, but I also was really lucky because I didn't experience, um, a lot of what I see is, is reported and, you know, not to diminish that at all, but there, there are really fun parts of the bros.

Right. Um, and I think we can take the good parts of that, um, and mix it up with the good parts of, of gender diversity. And so when we talk about things like, um, empathy, creativity, collaboration, you know, those are really, the female brain is wired differently and we have a different set of hormones. Now everybody's different. Um, however, on the whole, women's brains tend to want to focus on the vision and the strategy as it relates to the task at hand or the problem at hand, men with a lot of testosterone on board will want to attack that problem and kill it and solve it. And so both of those are really great assets, right? So you have, um, an opportunity, right. To really say, okay, how, but how big is this problem in the, in the scope of, you know, the larger, as it relates to these other things, because our brains talk to each other and then how quickly and effectively can we squash?

Can we dominate this problem? Um, you know, I'll give you an example during COVID, um, and women are, are more risk averse based on, and on a, on the whole, um, in business. And so sometimes in leadership, that's seen as a negative. Um, and I, and I get that, right. But I really do just think that again, it's about the balance and the gender, gender's working together. So I had a situation, um, during COVID where we had a really large contract, um, that was coming up for expiration. And this was like a, a really just important, important revenue stream for us. And one of our executives is male, the other female. And, um, basically the male was like, look, we have got to get this contract signed.

Like, let's sign it as is. Let's go, let's go, let's go. The female being more risk averse was like, we've got this pandemic in Asia. I think it's going to spread worldwide. Like we need to hold off and negotiate some act of God language in there before anybody signs anything. And so without that conversation taking place, our ass would have been grass telling you, um, if we had just done it one way, either, either way, because we needed it signed timely and we also need to take that into consideration. So that's kind of a, you know, black and white sort of example, but. How do you suggest, because I think the biggest, at least for me, it was blind spots of, of thinking that I'm a good guy, thinking that I'm, I'm, I'm, I foster diversity, thinking that I'm empathetic to women, but, but fundamentally can't be, you know what I mean?

Like I, I, I, I'm not a woman. So I, there's, there's empathy and there's sympathy. There's empathy. Like I, I've never been in a woman's shoes before, so I can't really understand, even though I think I do. So how do you approach a male like me who all good intentions, but has blind spots? And, and one of the things I learned from what we were talking about beforehand, this, that we need to talk, um, webinar that I did was we, what we did was it was really interesting. And I, and I want more people to look at this. We, I didn't, we didn't want to preach, right? We didn't want to preach. This is what you do. So it was me and three other women. And so what we did was you just surveyed and we said, Hey, this is a blind survey.

It's a, it's a empty Google doc. We're not going to be able. So I want you to answer three questions. One is, um, give us some examples of some things that happen within the workplace that are either sexist or put you in an uncomfortable position that aren't obviously sexist. Like the obvious sexist stuff is the obviously sexist stuff. And then give us some examples of, you know, some, some scenarios and then some positives. Right. And what, what was like screamed out loud to me through all that data was it wasn't the overtly sexist stuff. It was all the microaggression shit. Oh, okay. And it was this, this idea that if I complained about every little stupid sexist thing that happens throughout the day, I'd be labeled as a complainer.

But what happens is I, I suck it up, right? All right, whatever. So, but then it builds up to a point where I just pop and I usually pop on something that's seemingly not really that bad. And so now all of a sudden I'm emotional, it's that time of month and holy shit, but it's because so, and I look at that as, and that is, that hit me because I look back at my career with the women who have been on my teams and I guarantee you that there's been times as a, as a leader or as a, as a teammate where I've been like, yeah, yeah. And I've probably done something like, uh, you know, roll the eye, but because John's a good guy, I'm not going to say anything. Right. So how do you, how do you suggest women, we'll talk about men here in a minute too, but how do you suggest women approaching that scenario where it's these microaggression bullshit things that just add to your stress that, that seem small, but ultimately tip over and, and really cause some issues?

How do you approach somebody like me with that? So that's, um, that's a really great question. And it depends, it depends on the microaggression. So if you're, if it's something small, like you're assuming that I'm going to take all the notes for the meeting, cause I'm the only check in the meeting, but I'm actually leading the meeting and I'm your peer. Yeah. Then, you know, usually what I do, it's, it's like, all right, well, I took the notes last time. So who's, who's going to do it this time? I just have to speak up and be direct. I'm just going to call your ass out. But, but some, some people aren't wired that way. And some people, maybe that comes off as obnoxious in a, in a different company culture.

Um, and so I like to use humor a lot, you know, Oh, you think I'm your secretary again? Oh, okay. Got it. Well, in that case, I need a raise. I just, I like to make a joke out of it, but obviously everything's not a joke. Um, there are some very serious situations out there and so I don't want to discount those, but, um, you know, I think one thing that really, to me, just kind of stands out in my brain is, um, assumptions and ego and how that leads to like wasted time. So I think, you know, everybody's at work because we want a paycheck or we're doing it for some level of fulfillment, but we're not trying to just waste our time. Right. So, um, you know, I have, uh, um, actually one of my really good friends works at a very large, um, software tech firm, very well-known and she has a great job.

Um, she's smart as whip, so she, her boss, but her boss, um, so she's a one-year-old at home and her husband is a captain of a very large shipping company. It's a lot of responsibility and he flies out to Dubai for every three months or whatever. So she's like a single mom, but she's a girl, she's super smart. Anyway, her boss keeps dangling this carrot of if you jump through this hoop or do really well in this project or something, I'll fly you out to, um, you know, the West Coast. She's supposed to work for a week. And she's like, I don't, that wouldn't, that would bring so many problems to me. I have no local family right here. I would have to leave my, I'm not leaving my one-year-old for a week.

Like that isn't, that is, that is in no way an incentive. And I actually want to avoid that. And I don't want to be sitting with you for a week in a hotel every night without, it's just, it just makes him look like an idiot. And she actually, it's wasting, it's not a relevant incentive. Right. So I think like, that's just a, a typical kind of, for lack of a better word, like asshole assumption. Whereas if that manager would approach her like, Hey, you're amazing. I want to keep you working hard and keep you around. What would be an incentive for you? What could we do that you, you know, would, would actually feel rewarded for? Or like, what motivates you? Tell me about your life. Like, what do you like to do?

Um, that five minute conversation would literally help that manager so much. She would be so much more productive. And oh, by the way, she just switched jobs to get away from that. Because he was just oblivious. Um, so I think just the seeking to understand, like, and I think that's the, that's the, that's the challenge I see is that there are so many people who are, are oblivious to their actions and they think they're good people. They think they're, you know, it's like the person that says, I'm not a racist, you know, I got black friends and it's like, uh, yeah, but you just said some shit that you probably shouldn't have said, you know what I mean? And that like that, that affected me. So I've always, I'm always trying to search for like, how do you wake people up to their ignorance without insulting them and, or, or to their impact?

And, and, and look, don't get me wrong. There is a line here where it's like, all right, grow the fuck up. Like you need to, you need to, you know, suck it up and deal with this shit because that's just absolutely right. I do personally, and this is probably going to get me in a lot of trouble, but I think we've gone a little bit too far on the, the, the mental health piece. And I am a huge advocate for mental health, huge when it's real, but just because you had a bad day doesn't mean you need a mental health day. Like sales, for instance, is a stressful fucking job. Step the fuck up and go to work, right? Like you don't need to take a week off to clear your brain. Cause you, you had a bad week.

I need a paid week off. Right, exactly. Like, come on. So, but I do think that there is a, there is a, a lack of understanding, especially from the older generations of, of like, wait a minute, what is this? Like, what, like I didn't, I never cried when I was a kid, you know, I was told to suck it up. So it's that, it's that syndrome of, Hey, this is what, this is what I, you said it earlier. Like, this is what happened to me. So therefore that's, that's what you got to do. You got to come into the office. You got to work nine to five. You got to do these things. I don't necessarily think it's, it's, it's misinformed. I mean, maybe it's misinformed, but, but it's malicious. I just think it's ignorance.

And so I'm searching for ways to uncover that ignorance without insulting. I really believe there's a lot of power and a strong feedback loop. So I worked in renewals for, for a while where we were looking at the high volume, low dollar sales and really looking at, you know, how can we improve those renewal rates? And one thing that I took away from that was the power of that systematic customer feedback. We would do like a voice to the customer on a regular basis. And that literally made us so much money because we would, we would take that customer feedback. And so we implemented it on the team and we would do a team customer feedback survey internally. And, and then we would like have actually make changes.

I think the younger generations just want to feel heard. Like if I'm my neighbor down the street that has a one-year-old, it takes her an extra hour and a half to two hours a day. If she has to pack up all of her stuff to pump and bring it with her to work, let alone we're in Atlanta and the, the traffic and all that. So if she's going to write on that survey, please let me design my own hours or please don't make me come into the office for this amount of time while I'm pumping. Right. I mean, that's really good intel because there's probably about a few hundred of her in the same situation and you would get two hours more of productivity and a much happier human at your organization. If you could just listen to that.

Right. So I think for me, I've had really good experiences. If you have like a muscle of a feedback loop that you're constantly analyzing as a leader and making people feel comfortable sharing that kind of stuff. What, what form does that take? Does that take, I mean, tactically here, what form does that take? Is that a, is that a blind survey? Is that a one-on-one meeting? Is that a team meeting that you do consistently once a week? What is it? So start like, honestly, start with like an anonymous survey monkey or, or whatever survey platform, Google form, whatever that you have. I mean, that's how I started at volume. And then what I would do is we had like a, um, I wanted to empower people on the team.

And so we had like a focus group internally called them champions. And so they would kind of like represent their, um, unit. Um, and then I would meet with them every other week or every, you know, every other week or every other month, depending on the need and how urgent, you know, the, the feedback was or whatever. So, um, and when you say, when you say their unit, would that be like one woman who represented a group of women or, uh, uh, somebody who represented a certain division of an organization type of thing? Like, uh, like, um, location wise. So one person would represent one or two people would represent, you know, this city. Um, and maybe there would be 15 reps in that city. Um, for example.

So I had about, you know, uh, you know, double digit, um, 20 to 30 champions globally that would represent then the broader team. And so we would meet, we'd have an, um, open conference call. So they would hop on, you know, it was kind of like office hours for me. And we would go over the feedback that was submitted the month prior, and then they would come forward with any additional context related to that. So it'd be like, Hey, we've got a couple of folks from the team really have these special circumstances or requested, no, this is why it came through that way. Um, and that way it allowed everybody to remain anonymous, but then you still get contacts and their individual managers would, um, you know, meet with them and have their reviews and all that.

But this was just to make sure we were in touch because I was like more of on a middle, middle management level. So you had your managers and directors. And so I wanted to stay close to what the team needed and keep generating that revenue and not be like in some ivory tower. Um, so that seemed to work for us. One more question that I think we can finish up on, even though I think it's going to go long is how do you really like, what measures can an organization put in place to, to realistically track the impact of diversity in an organization? And the reason I asked this is because what was very disheartening to me that happened over the past three or four months, especially in the tech space is it when the tech, when the bottom fell out, the first, like tech is, is such a, you know, they, they, they preach diversity and, and all this other stuff.

And, you know, and yet the only black person in the executive team is the chief diversity officer. Right. It's like, you know, check the fucking box or they have a DEI team. Right. But as soon as times get hard, they cut that DEI team off, you know, like, I'm sorry, we can't, we can't find that anymore. Right. So with an understanding and, and, you know, the data, right. Of, of like how much more effective these can be, how can organizations start to put some things in place? So when the economy tanks, you know, that type of stuff that they can actually look at this, this and say, no, no, no, no, you don't want to cut this because this is actually the thing that's helping us get through this.

What are some like baseline things that, that can objectively show as opposed to, I feel like it does, it feels right. It's the right thing to do. No, no, no, no, really. It is the right thing to do. And this is how to do it. So, and I think, honestly, I've seen, I've heard about some startups and I'll get back to you on the names that are implemented, that are actually tracks, HR tracking type software that will track the benefits. So it's having more diverse hires and, and as they go leadership. So I know those startups are out there and bubbling up, hopefully they'll become more popular. But in one word, my word for this is let's focus on velocity. So as a sales professional, deal velocity is always super important.

Taking a lead from, you know, just being someone on the street through the marketing pipeline, through the sales pipeline to a closed deal. It's the same deal when we look at entry level diversity versus folks that are moving up the leadership ranks in past VP to senior VP up to the C level. You know, what we're seeing is that, you know, there's just, there's this, we're bumping up against this mid-level, mid-management ceiling. Even when you go to first level sales management, you see a steep drop off of females. It's even worse for, for, you know, ethnic diversity. So when we start to look at, there's a way to track, even if you have one person in your organization tracking, you get some kind of software to track, how quickly you are promoting diversity up through your pipeline of leadership.

So at each level of leadership, what does the diversity makeup look like? And then if you could track individuals and how quickly they are moving up that pipeline, as opposed to folks that are from a traditional, you know, white male background or whatever. I think that's super helpful. I'm no HR economist or whatever, but that is one thing. The data is definitely pointing to is their stagnation and leadership also. And this is where I think sales training or some type of training would be amazing. If you just have an online course that everybody can, could do, or some kind of formal way to everybody self-identify how they're contributing to revenue. So even if you're like a graphic designer or somebody that's not directly in sales, there's always a way that you can tie yourself to revenue.

So if you can, you know, make sure that you're, um, that everybody can communicate or articulate what type of revenue they drove. Um, you know, I know we cover some of that performance reviews and all that, but there's got to be more of a systematic way to say, okay, actually this, you know, having more diversity at this level drove X amount more revenue this year. But then when we didn't have diversity, um, yeah. And I think that's, I don't have a magic wand, but no, but I don't think you're, and, but I think we need to, you know, keep evolving to it. Right. It's kind of like environmental impact of things. It's like, again, my wife's an environmental scientist and it's like, you can, you know, there's one thing, the feel good thing about recycling, but then you look at the data on recycling and you're like, uh, the data on recycling is not that great.

Right. So like most of that stuff, put, you just put on a boat and ship to China and then it's dumped into some, you know, landfill that whatever. So there's ways that we can, we can point to like, no, that made a difference. Then we can, we can start to wake people up because I think ultimately the thing that's sad is that from a business standpoint and it, I mean, it is capitalism, right? That at the end of the day, numbers matter, right? Period. So the, the more objective we can make this versus subjective, I think the better off we're all going to be, because then we can actually say, no, actually this makes a real difference within the organization. And, you know, as opposed to, it's just the right thing to do, like, cause I think we could all agree that it's the right thing to do.

It's just when the jackass up top decides to look at the bottom line and say, well, yeah, but you know, that's the part that kills it. So I'm hoping that there's some of those startups maybe come to, you know, uh, have a, have a magic button or something like it shows, oh, if we, you know, if we're this diverse, then it actually increases that. So therefore this is the last thing you want to cut. We track so many things about business. I mean, come on, there's not a way to track velocity of backgrounds. Exactly. Through leadership. It shouldn't take much, right? So anyway, but the good news is that, you know, more, um, the more that we can spread around the wealth or have an opportunity to economically empower folks.

I mean, you're seeing a direct correlation with, um, the quality of, um, childhoods and, and opportunities that children have. The amount of, um, the way that communities can thrive, GDP and domestic violence rates go down. Yep. When you see, um, so, you know, absolute macro, there's no question on the macro side of the house, the impact that that has. I'm, I'm trying to wake those CEOs up that, that over the past three fucking months cut all their DEI and all their, you know, diversity programs because they didn't, you know, they didn't fund them anymore. Like those are the ones I'm trying to wake the fuck up. Well, I appreciate your effort for sure. We'll see. Maybe one of our two of them's listening to this one can wake up a little bit.

Well, Kelly, look, uh, we could keep talking about this for a while here, but, uh, talk to, uh, we're up on, we're up on time here and what talk, tell the audience a little bit more about, you got a book coming out. You got a cool program for, uh, women and entrepreneurs and everything else. So tell people where they can find out more information. Sure. So you can link in with me. Um, my information will be included. Shoot me. You'll find all of my information on my LinkedIn page. I run a program called the scale school, which, um, is a quarter long workshop for, um, folks that are looking to sharpen their sales skills, um, particularly women or, um, corporate organizations that are looking to, um, have a clear, have their sellers internalize a clear path to revenue.

So I take the anxiety out of selling. Um, but link in with me, go to empowered engagement.com and follow me on Instagram, the scale school. Well, and what's the book going to be about? The book will be about my research of females in leadership and revenue leadership. So all of those statistics and, and my recommendation of tracking velocity, um, will be in that book as well. So it won't be published until next year, but I'll definitely give you a shout when it's coming up. Um, so I'm, I'm super excited. I just got the, um, first draft. First draft is almost done. So. I love that. Congrats. I know writing a book is, uh, it's a journey, uh, if nothing else. Uh, so, uh, yeah, let's see. Let's reconnect next year when it launches maybe.

And we can hopefully talk about some of the improvements that we've made. Right. Cause I had, I, you know, on that, uh, on the, we need to talk. I had a couple of people who had been on that show with me and, and it was like two or three years later. And I was like, so based on where we were then and where we are now, like how much have we improved? And it was like, she was like, uh, maybe three, 4%. I was like, gosh, I was like, well, at least we've, I'm like, at least we've gotten, you know, we're, we're starting, you're starting this. But I think the more we have these types of conversations out loud, if nothing else, it, you know, one or two people can kind of, what you're doing is making an impact for sure.

So I definitely appreciate it and appreciate you having me on. Um, this has been, it's been great to, to, to be here. So thank you. It's been fun having you on. I appreciate it. So thank you again. And everybody, thank you so much for listening. And as always, hopefully you enjoyed the conversation as much as I did. And look, like I say, at the end of all my podcasts here, go out there and make somebody smile today. Cause no matter how bad your day is going or you think it went, you make somebody smile today and you know, you had a good day and the world needs a lot more of that right now. So thank you all very much. And I will see you on the other side. I hope you enjoyed that conversation as much as I did with your support and our incredible guests.

We're one of the top sales podcasts out there right now. And I can't thank you enough. Now to keep the momentum going, it would mean the world to me. If you could go and leave a five-star review on your favorite podcast platform and share some of your favorite episodes with your network. Also, check out my new website at www.johnmichaelbarrows.com where you'll find even more ways to engage. There's a ton of free content and you can also get trained from me directly as an individual or for your team. Look, I'm out there selling every day just like you are. And I'm doing my best to stay on top of all the latest trends in technology. So if you're looking to level up and you give a shit about this profession of sales, let's connect and let's make this happen together.