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He Handed Her His Coat and Said Coffee, Black. She Was the CEO.

August 17, 2026

Denise Conroy
Erica Rooney smiling with a microphone in hand

Hey there!
I'm Erica Rooney

I'm an ex corporate girl, turned founder, and 2x bestselling author, and I help women get into positions of power - and STAY there - without burning out.

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He Handed Her His Coat and Said Coffee, Black. She Was the CEO.

A note before you read on. This episode includes a discussion of childhood sexual assault, roughly between minutes ten and thirteen of the audio, and that section appears in the transcript below. Denise shares it in her own words. If that is not something that serves you today, skip ahead or come back to another episode. Take care of yourself first.


Now, the story I cannot stop telling. Denise Conroy walked into an investment bank in New York to pitch lenders on refinancing a very large pile of debt. She got there early, dressed for it, standing alone by the breakfast buffet. A man blew in, took one look at her, handed her his coat, and said: coffee, black. She hung the coat up. She brought him his coffee, from a self-serve buffet, which she would like everyone to note. Then everyone sat down and the CEO of the parent company said, and this is Denise Conroy, CEO of Iconic Group. He was sitting directly across from her. He went beet red and left the meeting inside ten minutes.


That is funny until you look at the numbers underneath it. Lean In and McKinsey found that 1 in 5 women are often the only woman in the room at work, and for senior-level women that jumps to roughly 40%. More than 80% of those Onlys are on the receiving end of microaggressions, compared with 64% of women overall, and women are twice as likely as men to be mistaken for someone more junior than they are. Denise is a three-time CEO and a former Fortune 500 CMO. She still got handed the coat.


Her path there was not clean, and she does not pretend it was. A childhood she describes as messed up, a marriage that ended after twenty one years, a head of HR who slut-shamed her at HGTV, and a stretch where she used accomplishment as a drug and then wine to numb it. Therapy, several years of it, is what actually moved her. She also does not exempt herself from the problem: after reading White Women by Regina Jackson and Saira Rao and watching Deconstructing Karen, she went back and reexamined how three women of color she recommended to the executive network Chief were handled, then cancelled her membership publicly on International Women's Day. The post reached the New York Times. She calls the reflex that had kept her quiet about it white woman bullshit, and she means her own.


And then there is the line that gives this episode its name. Denise says the key to your executive presence is the thing people either love you or hate you for, and hers is that she will walk into the most powerful room and say the thing half of it is already thinking. Half are grateful somebody finally said it. The other half decide she is a mouthy bitch. That split is not in her head. Laurie Rudman's backlash research found that women who act assertively get rated highly competent and then get penalized on likeability for it, while identical behavior from a man reads as leadership. Knowing that does not make the penalty disappear. It does mean you can stop assuming the problem is you, and start deciding what the thing you get loved or hated for is going to be.

TRANSCRIPT:

Erica: Hey, girl. By now, you know I have HER Collective, my online community for ambitious women who are done doing it alone. HER Collective is for the women who are smart, capable, and driven, but they find themselves stuck on the sticky floors like self doubt, burnout, and waiting for permission that quite honestly never comes. Inside HER, you get more than motivation. You get real support, real strategies, and real momentum.


Erica: We work on things like clarifying what you want now and what's coming next, building confidence without burning yourself out, handling hard conversations, career moves, and leadership moments with clarity, and surrounding yourself with women who actually get it. This isn't about hustling harder. It's about moving intentionally with the right tools and the right people in your corner. If you're ready to stop spinning, start choosing yourself, and build a career and a life that actually feels aligned, I'd love to welcome you inside HER Collective. You can learn more and join us at www.joinhercollective.com.


Erica: Because honestly, girl, you were never meant to do this alone. Hey there. I wanted to jump in before the episode starts and give you a quick disclaimer. We cover a lot of amazing things in this episode, from white woman BS to mean girls, alcohol, and, of course, the mediocre white man. But we do talk about sexual assault in this episode, between minutes ten and thirteen.


Erica: If this is not something that you wanna hear about, if it causes any kind of trigger or trauma, please skip this episode, join us next week, or make sure that you fast forward from minutes ten to thirteen. This episode is jam packed with a lot of amazing sticky floor stories, so I don't want you to miss out. But I understand that may not be something that serves you. So if that is the case, take care of yourself first.


Denise: I really got to see the difference between how you treat a male CEO and how a female CEO gets treated. Female CEOs get paid less. The instance I was in, I ran a bigger org. Right? But I'm getting paid less.


Denise: Do I think that they're bad guys? No. I don't think they're bad guys, but I do think that we've all got biases, blind spots. And that's the sort of thing, sticky floor wise, that I'm really committed to changing, because it's patently unfair.


Erica: Today's guest, Denise Conroy, is the queenmaker. She's a CEO. She's a former CMO. She's a board director, an author, a speaker, an advisor, and a performance coach, and recently someone who's broken the internet.


Erica: I have personally been following Denise for quite some time. I have joined every single webinar that she's ever hosted, because she's smart, she's a no bullshit kind of woman, and she's a fierce advocate for all minorities, donating over $125,000 of her services, 60% of which has gone to people of color and LGBTQ plus, to help provide them with opportunity and education and equality. So, Denise, I am super pumped to have you here. Thank you so much. How are you today?


Denise: Oh, thanks for having me. I'm great. I'm great.


Erica: Alright. Well, we've gotta dive right on in and just talk about your breaking of the internet. What did you do?


Denise: Man, I honestly did not expect it. Someone said to me the other day, you certainly expected it. I'm like, no. I did not. I'm a 51 year old woman.


Denise: We don't get heard a lot. So I was a member of the women's executive group Chief. I had joined back in 2020, was going into my fourth year, I guess, technically, and really found that, after being in the org, honestly I was in the org for about a year, and I had some issues with Chief. But a lot of them were growing pains. Right?


Denise: It was the stuff that you expect from a start up. And one of the cool things about Chief is it was founded by two women, took it from literally ground up to become a unicorn, having over a billion dollar valuation. So I think that, like a lot of women, I was so proud of that. It wasn't even my achievement. I was just super proud to see two women come up with a concept like that, grow it, get funded.


Denise: I think they pulled in like $140,000,000 in venture cap funding, and so I joined up right away. I really wanted to be with like minded women. I wanted us to mobilize on issues that were important. And it took me about a year to figure out that mobilization was not on the agenda. So I actually cancelled my Chief membership a couple days before International Women's Day.


Denise: I announced it on LinkedIn on International Women's Day, March 8, and I was stunned at how it took off. Like, I thought, honestly, people would be like, she's a rich white lady. She's annoyed and frustrated because she's a Karen. Right? She doesn't need


Erica: I was just about to say, are you being a Karen?


Denise: Are you being a Karen? Exactly. Like, I thought it might get a tiny bit of traction with people I knew, but I had no idea, honestly, that people would gravitate towards it, but they did.


Erica: And why do you think they did?


Denise: Why? Yeah. I think what the real recognition for it was, I think, one, we women, especially white women, we're real good at toeing the line with each other, and I've been doing a lot of anti racist work over the last couple years. Most specifically, I watched the documentary Deconstructing Karen, which is put together by Saira Rao and Regina Jackson, two women of color, who have an organization called Race2Dinner. And after I watched that mesmerizing but so uncomfortable documentary, and really in the documentary, what they do is they invite a bunch of white women to dinner, and they basically say, tell us about your racism.


Denise: And, of course, women are like, I'm not a racist. You know? Very resistant. So it was interesting to watch that self actualization realization with some of these participants.


Denise: But then they wrote a book, not too long after they put the documentary out. And the book is called White Women: Everything You Need to Know About Your Own Racism and How to Do Better. And what I loved about the book, when I picked up the book, it is one of those, for me at least, it was an epiphany read. It gave me insight into all kinds of messed up things that I think and do and say that are just not good, super not good. So for me, it was an epiphany.


Denise: And at the same time, I was having this experience with Chief. I came to find out, so as a Chief, you could recommend other women who you thought would make really good members. Right? So I didn't do much with that in my first couple years. And then in this last eighteen months, I recommended three women.


Denise: All three were women of color, and it was really weird. You'd fill out a form, or at least I filled out a form, that just said, who's the woman? What's her LinkedIn profile? Real brief. And I didn't get any sort of a bounce back email, like an automated email, like, thanks for recommending this woman.


Denise: But we were all told that if you recommended a woman, she would at least get an interview. Well, I didn't get any acknowledgment that I had recommended these three women, and then these women didn't get acknowledgment either, because I had to put in their email, their contact info. So I thought, honestly, when nobody got in touch with me or the women I recommended, a 100%, and this is white woman bullshit here, I was like, well, I'm just a pain in the ass, so they're probably punishing my women. Right? My recs.


Erica: Because of you.


Denise: Because of me. I'm like, so, yay. I feel great about that. So I kinda just dropped it, didn't go anywhere with it, and then organized for International Women's Day a couple weeks ago a book club, where Saira Rao came in really generously and spent an hour with us Chiefs on the Chief community platform. And it was really wild, because when I had scheduled the meetup, there's a little discussion message board connected to it, and another fellow Chief put something out there and said, hey.


Denise: I recommended this woman of color. The woman of color, she is Black. I believe she's also gay, and she is an influencer, like a massive influencer on LinkedIn, big in the DEI space. She's a chief people officer, and she was really put through the ringer for her Chief interview. And that viscerally affected me, because at that point, I was like, wait a minute.


Denise: My Chief interview, literally, I went and counted my documentation of this the other day, I was talking to the New York Times. It took me eleven days to become a Chief. I had a thirty minute interview. This woman was asked to substantiate her experience and all this other horseshit that, frankly, I didn't have to do and a lot of other women didn't have to do.


Denise: So I think that's when I started to connect some dots. Now I will say, people could say, well, maybe those dots are spurious. Maybe they're not the right dots. And I'll say, maybe they're not. I just wanted to kinda go on record and say, hey.


Denise: I think that this organization has some improvement to do.


Erica: Yeah. Well, I think you did it in a very eye opening way as well, because I saw your post, and it has not been my experience. But I also haven't done a lot of the things that you've done, but it has opened my eyes to now be more mindful and watchful of how those things may be occurring that I'm completely oblivious to.


Denise: All of us. I mean, I was oblivious to it. Let's be fair. And I think, honestly, someone asked me this. Had I not been doing my own work, reading the White Women book, Deconstructing Karen, interacting with Saira and Regina, I don't know that I would have questioned it in the way I did, to be honest with you.


Denise: I thank them for that education, and it's not their job to educate me. I just wanna say that. They're just kind enough to do it. But I would say that I don't think I would have known to ask the right questions.


Erica: But that goes to the whole thing, when you know better, you do better. Right? And you put yourself in the position to learn more so that you can do better. Right? Because you believe at your core that you are an advocate, and you put those words into actions, and this was just a piece of it.


Denise: It was. And I'm not a perfect advocate. You know? I love the word that Regina Jackson uses, an accomplice. Accomplice is fun.


Denise: But here's the thing. I'm never gonna be a perfect accomplice. And one of the problems with white womanhood is, and god, I'm 51, I'm not young, we are perfectionists for a reason, and we have that drilled into us from a very early age as little girls.


Denise: It's a way to keep us in line. It's a way for us to carry the load of white patriarchy, quite frankly. But I gotta unravel and get self actualized about the part that I've had in all this, because I've had a part.


Erica: Absolutely. We all do. We all do. Thank you, number one, for sharing all that. And I almost kinda wanna take a step back and hear more about Denise Conroy and how did you become this queenmaker, this CEO, this former CMO.


Erica: What is the story there?


Denise: So I had to be a real mess, I think, a beautiful mess as most people are, to actually learn to be comfortable in my own skin. My story starts, I was five years old. My mom had just had twins, and she let me out to play one day because I had just nagged her and nagged her and nagged her. It was a beautiful spring day. And the poor woman was just exhausted.


Denise: And she's like, okay, you can go out and play, but, you know, my parents were pretty overprotective. We lived in a not great apartment complex. And she's like, just go out, play in the yard. I'm gonna call you in in, like, an hour.


Denise: Right? Fine. So I go out into this green grassy area, and there were these bad neighborhood kids that were just always in trouble, always loafing around, like I said, not a great apartment complex. So they cornered me. They were teenage boys, one girl actually in the group, anywhere probably in age from 15 to 19, and they proceeded to sexually assault me for what seemed like forever.


Denise: You know, again, I have no concept of time, but I do remember thinking and being really mad. Like, why is my mom not calling for me? Like, why is she not coming for me? And I think I held that against her for a really, really long time. So, literally, they had had their way with me, kinda put my clothes back on me, and the girl in the group, who to this day, whether she did or didn't, she looks like Peppermint Patty to me.


Denise: I don't know why. And so it's funny, memories as a kid, weird memories. And she took me back to my apartment door. We were on the ground floor, and got down on eye level with me and said, if you say a word and tell anybody what happened to you, I'll fucking kill you. And I believed her, because I was little and I was powerless, and I had a messed up family anyway.


Denise: So I went into the house, and I remember my mom's like, you know, just all normal. How was your play? How did the play go? You know? She didn't know, and I'm like, fine.


Denise: And I just beelined for the bathroom, cleaned myself up. And, honestly, I never told another soul until I was in my early forties. I didn't wanna tell my mom. I was ashamed of it. I was small, but I knew enough to be ashamed.


Denise: My dad was a really violent guy, and I didn't want him. He was the sort of guy who got in the neighborhood fights. It didn't take much. So if he knew, he'd end up in jail, and I knew it. I actually had that sort of presence and that maturity as a five year old to know that my dad could be in jail.


Denise: And he wasn't great, but we didn't need him in jail. So, kept it to myself. Literally within an hour, right, I became a different kid. I went from being precocious and rambunctious and goofy to being shy, anxious, guarded, mistrustful. So I was shy, guarded, and mistrustful for decades.


Denise: Made a lot of missteps, but used accomplishment as a drug. Like, it was really, really good. I was an accomplishment junkie. And it all came to a head for me. I was working at HGTV.


Denise: It was in my early forties, and I'm in Knoxville, Tennessee. I was being harassed at work. The head of HR was really, really toxic. She was at my level, and she slut shamed me. I lost 50 pounds when I had first gone to HG.


Denise: I started doing CrossFit and eating healthy and all kinds of good stuff. And she would, through the grapevine, let me know on any given day that I looked slutty, skanky. These are all words that she used to describe how I was dressed. My skirts were too short. My butt was hanging out.


Denise: You name it. She had lots of fun little phrases to say. At that same time, my marriage fell apart. I was married to my college sweetheart. In honesty, I probably stayed fifteen years too long.


Denise: We'd been married for twenty one years. And interestingly enough, he had an affair with our real estate agent, and that to me was just like, god. You wanna talk about an emotional crush? Although in hindsight, he did me a favor, a 100%. I can say it now.


Denise: You know? And also, I'd never dealt with my anxiety. I mean, the way I would ramp up for a day at work, or just ramp up for a day, I was not right. I mean, I really, really wasn't. And what was bad is I started to drink.


Denise: I had always been pretty good. My dad was a massive alcoholic. Most of the men in his family were. And I had always done a good job of not really drinking a ton, and I got really, really into drinking just to kind of numb myself. I was very good at numbing, but I found that my old tricks wouldn't do it, so booze did it.


Denise: So I kinda had all this perfect storm of suck. And, oddly, I go to marriage counseling because I'm like, oh, I gotta save this marriage. Most important thing in the world. The great thing about marriage counseling was I'd never been to therapy. So when I finally get convinced to go to marriage counseling, I do, like, two sessions, and I'm like, I'm not staying in this marriage, no effing way.


Denise: But I think I'm gonna need some therapy on my own. And so kind of embarked on a three or four year journey of therapy. Like, I hate to say it, you don't realize you need to turn your life around until you actually turn your life around. And, you know, I walked out on my job at HGTV a couple months later, literally.


Denise: Nothing. No safety net, no severance that was planned. You know? It all worked out, but I didn't know that. And literally within a year, I'd met who's my husband now. It's just, it's hard to believe I'm the same person.


Erica: Hey there, listeners. If you have ever felt like you're stuck in a place, held back by self doubt, perfectionism, or that pesky inner critic, you're not alone. We all face those sticky floors that keep us from reaching the heights we dream of. But guess what? It's time to shatter those limiting beliefs and toxic behaviors to uncover infinite possibilities.


Erica: My book, Glass Ceilings and Sticky Floors, is your ultimate guide to smashing through barriers, overcoming limiting beliefs, and stepping into your full potential. This book has been endorsed by none other than the great Mel Robbins, best selling author and motivational powerhouse. It's also been featured in Success Magazine, so you know it's packed with insights that work. Inside, you'll find real life sticky floor stories, practical strategies to help you handle your own sticky floor moments, and a whole lot of inspiration to keep you climbing. This isn't just a book.


Erica: It's your roadmap to success, confidence, and freedom. Grab your copy of Glass Ceilings and Sticky Floors today at www.ericaandersonrooney.com. Whether you're in the boardroom, the classroom, or just starting out, this book is for you, because no one, and I mean no one, deserves to stay stuck, no one deserves to feel small, and you have glass ceilings to shatter. Let's do this.


Erica: Wow.


Denise: Yeah.


Erica: That's a lot to unpack, but I know that so many of your pieces resonate with so many women, because so much of what you just told me resonates with me. I always used accomplishments as the drug.


Erica: I always chased the next best thing. Like, as soon as I landed a C level job, I was looking for the next thing. You're thinking, how can you look for the next thing when you're in a C level job? Right? But you are.


Erica: Like, I used wine to numb out all the bullshit, because it does its job. It does its job of numbing.


Denise: It does. And it's really interesting, because you don't even enjoy the wins that you get. Like, I have never been good, and I still struggle with this, at just celebrating the wins. It would always be like, oh, I got promoted to CMO. On to the next one.


Denise: You know? And it's a really soulless way to live. It really is.


Erica: Yeah. Because you're constantly chasing something that you can never get to, because that goal post is always moving. It is literally a moving target.


Denise: Yes. So elusive. And you're never in the present. You're always focused on the future, which is a really interesting way to eat up your life.


Erica: Yeah. I always say having this growth mindset type mentality, it is a blessing and a curse. Like, it got me here. It's done its job, but it also sometimes steals from me the joy of the wins along the way.


Erica: Right? They talk about stopping and smelling the roses. I don't smell the roses. I just planted them. They're blooming. I gotta go over here now.


Denise: Yeah. Agreed. Don't you feel like, though, I felt like the pandemic was good in the way that, we had just bought a little hobby farm up in New Hampshire. We moved from Atlanta. And I feel like the pandemic, for the first time, because we kinda had to, I got into smelling the roses.


Denise: I got into gardening, for god's sake. Like, it's pretty incredible to let yourself just kind of enjoy nature and what is, instead of always being like, what's coming next.


Erica: Absolutely. Living in the present moment is so important, because none of us are guaranteed another moment on this earth. Right? Let alone a tomorrow. So it is so important to stop and smell the roses, to celebrate the wins, and just to be happy in the present moment.


Erica: So, Denise, when you think about sticky floors, because we've got a lot to unpack here, what resonates with you as, like, the stickiest of floors that you had to pull yourself out of?


Denise: I think for me, that floor at HGTV. Because here I am. I go in. You think it's gonna be a dream job. So I had come from, little context, I came from the Outdoor Channel.


Denise: So I worked there for almost eight years. It was out on the West Coast, but it wasn't like one of those hip, cool West Coast television networks that would usually be in Los Angeles. It was a family business. It was all about hunting and fishing and shooting sports. It was based in Temecula, California.


Denise: It's a good two and a half hours outside of LA. I was the only female on an all male executive team, and it had pitfalls. Don't get me wrong. It had pitfalls. It had drawbacks.


Denise: But then I got to HGTV, and it's 75% female probably at their corporate office in Knoxville. And I'm like, oh, this is gonna be amazing. And to be honest with you, I hadn't worked in a largely female org. I never had. I'd always worked in steel.


Denise: I've worked in all kinds of very male orgs. So I go into HG, and, man, it was crappy. And this goes back to what you were saying. Now I'm starting to unpack, like, white women. It was super white.


Denise: It was super female, and people weren't super nice to each other. And I'm not pretending like I'm above it. I'm not above it. Like, I got sucked into it some days too. Right?


Denise: One of the things we learn as kids, as girls, is that knowledge is power, and that becomes gossip. And that's a way that you can flex your power. And you wanna talk about a sticky floor, the gossip that would meander through those halls and pass as truth. Right? Like, I remember when my husband had left me.


Denise: Well, I'd asked him to move out, but however you wanna phrase it. People at work, I feel like, knew about it before I knew about it, because I had all these people that lived in my neighborhood that also worked at HGTV. One of the only places you could work in the town. Right? And so gossip was a piece of the sticky floor.


Denise: Toxicity was a piece of the sticky floor. And also this notion of, like, what women are supposed to be. Like, I'll never forget. I got on the elevator one morning to go up to my office at HG, just coming from the parking lot. And I'm sharing an elevator with this guy who's the CFO of our big umbrella company, the holding company.


Denise: And, you know, this guy never said boo to me. Right? And we get on, and I had just bought a new car. My husband had just left, and it was totally my midlife car. It was a Porsche Cayenne.


Denise: And by the way, everybody at HG drove really nice cars. We were paid really well. Just saying. I wasn't alone here.


Denise: And he says to me, man, I think we're paying too much around here. Saw your car. It's awfully nice. And I looked over at him. He pulled up in a seven series Beamer.


Denise: And I was like, Joe, it's the same price range as your car. So it was just like, what? But it was somehow okay for him because he's a guy, and it's not okay for me.


Erica: God. What an asshole. I mean, I just had to say it.


Denise: That stereotype, the notion of one standard for me, one standard for the underlings. Right? And there's a huge gender component, certainly a racial component. That whole sort of elitist class thing doesn't really work for me.


Denise: That's some bullshit. It was some hardcore bullshit. You know? And then as you think about, so I ended up leaving HGTV, and I was like, you know, I think I can be a CEO. I'm like, I'm really good at strategy.


Denise: I have a lot of things I think that would suit being a CEO really well. So I leave. I go on this ten month quest to find somebody who's gonna give me the opportunity to be a CEO, and I meet these two guys. One is in private equity at Raymond James. The other is in private equity at a firm in New York.


Denise: Really, really brilliant guys, very different guys. And they were sharing an investment. They were both in on this investment, which at the time was about an $80,000,000 event photography company. So I go in. They need a change.


Denise: I go in as the CMO, and they're like, be a CMO for, like, two years. You can train under the guy who's the CEO right now. Well, they hadn't bothered to tell the guy who was the CEO and really enlist him, include him. They were like, yeah. We're gonna hire this woman.


Denise: She's gonna come in and build our first marketing function, and then she'll take over your job. Your successor. Right. So he loathed me from, like, square one. I'm, like, six months in, and I go to the board, these two guys specifically, and I'm like, this is not working. And by the way, here are some things I'm seeing.


Denise: So they were like, well, for better or for worse, I think you're gonna be the CEO now. So after six months, way ahead of schedule, I'm the CEO, and completely tanked, like, my first year. Like, completely tanked it. Did all kinds of stuff that, it was like a primer on what not to do, basically, as a first timer. But I think when you talk about sticky floors, and these guys were about as progressive.


Denise: I felt like they mentored me, sponsored me, embraced me. I mean, even when I messed up, they were really good about not crushing my spirit. But then after I was out of that role for a while and I was on another one of their boards, I really got to see the difference between how you treat a male CEO and how a female CEO gets treated. Female CEOs get paid less. Although in some instances, the instance I was in, I ran a bigger org.


Denise: Right? But I'm getting paid less. So, again, do I think that they're bad guys? No. I don't think they're bad guys, but I do think that we've all got biases, blind spots, and that's the sort of thing, sticky floor wise, that I'm really committed to changing, because it's patently unfair. You know?


Erica: Absolutely. Absolutely. Now I love this, because I've fallen down the Denise Conroy TikTok.


Denise: Oh, god. Great.


Erica: Mhmm. And I saw the TikTok from when it came time for y'all to sell off that business. And I came from private equity, a little background, so I'm very familiar with this process. Please do tell the story, Denise, about showing up in New York City to present yourself. CEO, here we are. Take it away.


Denise: Yeah. So we get bought by a strategic buyer in 2018, and it's another company, but they're backed by private equity as well. Little do we know that they are just laden with debt. They've got so much debt. They've literally got, like, $400,000,000 in debt.


Denise: So they come to me right out of the gate once our sale is finalized, and they're like, hey. We gotta go to the investment bank in New York. We are gonna have to literally dance and prance and tap dance, do it all, for basically lenders, because we need to do a big refinance of all of our debt. That was, like, $460,000,000. And they're like, since you're the CEO of our subsidiary, you're gonna come in and be part of the pitch team.


Denise: Right? Cool. And my business was super, super healthy. The other business who bought us, not as healthy, but mine was healthy. So I'm like, cool.


Denise: Anything for the cause. So every day, we are, like, back to back lined up with all these meetings. I get there early one morning, and I'm dressed business. I got heels on, the whole thing. Because, of course, I'm like, what's presented about me?


Denise: But we go in, and I'm by myself, and they have the breakfast buffet all sitting there. And this guy flusters in, and he looks at me, takes his coat off, he hands it to me, and he goes, coffee, black. And I'm like, it took me, like, a split second to be like, oh, he thinks I'm the admin, and I just set up the breakfast. And yeah. So instead of my normal, you know, just get hostile, because that's kinda who I am, I didn't do it.


Denise: I was able to contain myself. I went out to the front desk and said, hey. Where's the coat closet? Right? She shows me.


Denise: I hang it up. I go back in. I give him his black coffee, which is hysterical, by the way. It's a breakfast buffet. It's self serve just by its definition, so I'd like to say that.


Denise: But this guy was a complete asshole. So we go to sit down, and I'm thinking in my head, oh, wait till we sit down. We go to sit down. We make the introductions. The guy who's the CEO of the big enterprise where I'm working, he's like, and this is Denise Conroy, the CEO of Iconic Group, and this little man is right across from me.


Denise: I made sure he was right across from me. And he is just beet red. And it was just like, it was magical. He didn't last in this meeting but ten minutes. He's like, I gotta go.


Denise: And it was weird, because his two or three partners that were there looked at him like, what the hell is wrong with you? And I don't know if he ever came clean, but it was sort of brilliant.


Erica: No way he came clean. There is no way he ever came clean, Denise.


Denise: It was so sad. I'd love to tell you he was old. He wasn't old. He wasn't old at all. I think he was younger than I was. It's hard to believe.


Erica: There's no way he came clean, but can we say what a flex? It's like, you know what? Yeah. I'll take your coat.


Denise: I'd be happy to get you coffee.


Erica: No problem. Because you were like, I'm just gonna let this play out. Let's go. It's game time.


Denise: Let it ride. They were very boring meetings, so I was like, this is gonna be the most excitement I have for all week.


Erica: Oh, I absolutely love it. So then how does that translate into what you do now?


Denise: So what I do now and how I got here. So I ended up going on to run two other companies. I was six months into my last company I was running, and I just was exhausted with explaining myself. I was like, I'm still the youngest woman at the table. I'm in my fifties. Like, I was 50.


Denise: I'm like, I'm still the youngest woman at the table, and I'm the only woman at the table in most boardrooms and most meetings, and it just hasn't changed. I'd love to say it's changed. A lot, it hasn't changed. So I was part of the great resignation, and I decided that one of the things that brought me the most joy of all the time, almost thirty years of working in corporate America, was coaching, mentoring, bringing people along. Right? Really thinking about grooming, succession pipeline.


Denise: And I wanted to be, for other women specifically, I wanted to be that resource that, frankly, I wish I would have had. I came from a really poor family. We did not have socialization skills on par with a lot of the folks that I frankly have had to compete against in my career. So to be able to say to other women, number one, you don't have to be a genius to be a C level executive. And here's kind of a very concrete road map to get you there.


Denise: And also, let's face it, I'm in my fifties. This is my last chapter. So I wanna be sure that I can be part of the change, part of the mission, that changes the world. I really believe that at the end of the day, we need more women in leadership roles, not fake leadership roles, not performative leadership roles. And when I say women, I mean white women, Black women, brown women, women. Right? I just think that we're missing an entire perspective of leadership.


Erica: Absolutely. Absolutely. Well, Denise, one question I love to ask everyone on my podcast is, if you could go back to the Denise who is a woman in this man's world, right, who's chasing accomplishments, struggling with anxiety, alcohol, all the things, what is the one piece of advice you would give her?


Denise: The one piece of advice I would give is to cut herself some slack and stop trying to be something she's not. Whether we're forced to or whether we think we have to, we wear masks and we compartmentalize. We're master compartmentalizers. And I think for me, it took me therapy. It took me getting into a good, confident, self aware place of my own to figure out that the key to what makes me great is the stuff that, honestly, throughout my career, sometimes I've been knocked on.


Denise: I always say that the key to your executive presence is that thing that people either love you or hate you for. So for better or for worse, the key to mine has been, I speak truth to power. I will go into the most powerful room, and I will say the thing that half the room is thinking, and they're like, oh god, thank god somebody said it. And the other half is like, what a mouthy bitch.


Denise: Why does she have to say that? Right? And so for me, I wish I would have recognized that a lot sooner.


Erica: Amazing. Yeah. For all of my listeners, all of my other queenmakers and queens out there, Denise offers amazing masterclasses, learning sessions, all on how to read financial statements, how to understand everything. Tell us, where can we find these things, Denise? How can people work with you, reach you, all the good stuff?


Denise: Absolutely. So you can go to my website, which is themyllc.com. If you just click on the store, you can see all my offerings, from one on one coaching to the virtual workshops, and you can always email me directly at dconroy@themyllc.com.


Erica: I love it. She's awesome on LinkedIn as well. So if you were not one of the new 6,000 followers, we can always use more. But, Denise, thank you so much for being here today. It's so awesome to have you.


Denise: Thank you so much for having me.


Erica: Hey there. Before you dash off to the next episode, hold up one minute, because I've got a great freebie for you. You see, I've been on the hunt for the perfect planner, but nothing seemed to fit. The daily ones were too tedious and the monthly ones were too long. So I created the perfect weekly success planner.


Erica: This is what I use every single week to stay focused on my goals and what's important in life. And I've got a copy linked in the show notes for you for free. So click in there today and make sure you grab your copy.

​RESOURCES MENTIONED IN THIS EPISODE:

- Ready to stop spinning and stop doing it alone? Join HER Collective, Erica's community for ambitious women in corporate America.

- Grab Erica's book Glass Ceilings and Sticky Floors and start shattering the beliefs that keep you stuck.

- Never miss an episode of Glass Ceilings & Sticky Floors.

- Work with Denise Conroy at Themy, where her coaching and virtual workshops live.

- White Women: Everything You Need to Know About Your Own Racism and How to Do Better by Regina Jackson and Saira Rao, the book Denise calls an epiphany read.

- Race2Dinner and Deconstructing Karen, the documentary and the organization founded by Regina Jackson and Saira Rao.

- What being an Only at work is like from LeanIn.Org and McKinsey, the research on being an Only and the microaggressions that come with it.

- Prejudice Toward Female Leaders: Backlash Effects and Women's Impression Management Dilemma by Laurie Rudman and Julie Phelan, the backlash research on why assertive women get marked down on likeability.

- It is time to advocate for your damn self.

RELATED EPISODES:

Self-Advocacy Is a Muscle: How to Start Asking for What You Actually Need

He Handed Her His Coat and Said Coffee, Black. She Was the CEO.

The Negotiation Mistake That Costs Women 18 Cents on Every Dollar

FREQUENTLY ASKED QUESTIONS:

What does it mean to be an Only at work?

An Only is a woman who is often the only woman, or one of the only women, in the room. LeanIn.Org and McKinsey found that 1 in 5 women are Onlys, and for senior-level women that rises to roughly 40%. More than 80% of Onlys experience microaggressions, compared with 64% of women overall, and women are twice as likely as men to be mistaken for someone in a more junior position. Denise Conroy, a three-time CEO, was handed a coat and asked for black coffee at her own pitch meeting, which is that statistic with a face on it.


Why do women get penalized for speaking up at work?

Because assertiveness gets read differently depending on who does it. Laurie Rudman and Julie Phelan's backlash research found that women who behave assertively are rated as highly competent and then penalized on likeability for it, while identical self-promotion from a man reads as confidence. Denise Conroy describes the split exactly: she says the thing half the room is already thinking, and half are grateful while the other half decide she is a mouthy bitch. Knowing the penalty is structural rather than personal does not remove it, but it does stop you from concluding the problem is you.


What is executive presence, really?

Denise Conroy's definition is the sharpest one on this show: the key to your executive presence is the thing people either love you or hate you for. Hers is that she will walk into the most powerful room and say the thing everyone else is thinking. Her advice is to stop sanding that quality down to be more palatable, because the trait you keep getting knocked for is usually the same trait that makes you valuable. Cut yourself some slack and stop trying to be something you are not.

MORE FROM ME

Follow me on Instagram @ericaandersonrooney and @joinhercollective

SUBSCRIBE & REVIEW

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Hi, I'm Erica!

In the last 15 years, I climbed to Chief People Officer, 6x'd my income, walked away from a culture that stopped matching my values, wrote two books, and built HER Collective to help thousands of women rise to power and lead in the age of AI. I've learned a thing or two about smashing ceilings and closing gaps, and Glass Ceilings & Sticky Floors is where I open the playbook, the receipts, and the real stories to share it all with you.

Erica Rooney in a pink vest, holding a microphone in front of a director's chair with a podcast mic and her two books, The AI Gap and Glass Ceilings & Sticky Floors, smiling
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