Ep. 38: The Truth About Bias in Corporate Leadership With Cherie Caldwell
What does it really take to lead in environments that weren’t originally designed for you?
In this powerful guest episode, HR executive and leadership strategist Cherie Caldwell joins Laura to unpack bias, leadership, psychological safety, and what it actually means to build strong, aligned teams.
Cherie Caldwell is a former VP of Human Resources and senior HR leader across major corporations including Comcast, NBCUniversal, The Home Depot, Delta Airlines, and SalesLoft. Now founder of The Cherie Caldwell Company, she helps leaders transform—not just train—through coaching, leadership development, and team alignment work.
What You’ll Hear
✔️The business case for engagement and inclusion
✔️Why “just hire the best person” often ignores unconscious bias
✔️Real corporate examples of bias in hiring and performance review
✔️What it was like rising to executive leadership in corporate America
✔️The hidden “game” happening alongside the business itself
✔️Why working hard is not enough to advance
This episode bridges business performance and human dynamics—without blame, shame, or polarization.
Guest Information
Book a complimentary ideation session or coaching call:https://www.cheriecaldwellcompany.com
Connect with Cherie on LinkedIn: https://www.linkedin.com/in/cheriecaldwell/
If leadership, alignment, and transformation matter to you — this conversation is your invitation to lead differently.
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You are listening to the pivot point where we unpack the defining moments that shift careers and lives. I'm your host, Laura Dionisio, a founder of Lead Intact, and my mission is to spotlight the raw real stories behind career pivots, the fears, the hopes. The messy middles and the bold decisions that follow if you're feeling stuck or quietly wondering what's next?
I hope these stories help you see yourself a little more clearly and inspire you to start moving toward your own dream life. Let's begin.
Cherie, welcome to the Pivot point. As soon as I saw that we were recording today, the Stevie Wonder Song Mache a More came to mind. I am so excited to have you here. Thank you for coming on the show. Oh, I'm so excited too. So super, super excited. Actually, I can't wait for us to chat. I love it. And listeners, you're in for a treat.
Just so you get to know her better. Let me go ahead and read her very impressive bio. Cherie Caldwell is a human resources thought leader that helps leaders develop individually and as more effective and productive teams. She's the former region VP of Human Resources for Comcast, NBC, universal Director for the Home Depot, managing director for Delta Airlines and head of de and I for SalesLoft.
Cherie rebranded and launched the Cherie Caldwell Company to help elevate the quality of leaders and the alignment of leadership teams via a comprehensive system of training, coaching, and on the job experience, working with leaders to ensure healthy team dynamics and alignment. Sheie doesn't train. She helps leaders transform and grow.
Welcome, welcome. Big round of applause to Shere.
Uh, my first question is. What was it like hearing me read your bio? 'cause I know that can be like a really cool experience. Yes, it is. I was just like, oh wow. I've done a lot. You have done a lot. Yeah. And really I think all those experiences led me to what I'm doing now.
Right? It's like I developed some strong skills and capabilities and all those different corporate roles. Mm-hmm. And so that's what I'm doing. I'm looking at how do I help individuals. Get stronger and actually learn to be a little bit more vulnerable so they can have a stronger team. Mm-hmm. Right. And it's just like acknowledging that when you have superstar players on a team, that's great, but you win when you operate as a team, you know, the individual superstars don't take you all the way.
You have to operate as a team. And then I think the other thing about that is just using my experience to help other women navigate through corporate America. Mm-hmm. Because it is. A navigation. You do need to learn how to grow in a space that's not necessarily supporting you. So how do you support yourself to do that?
And how do you build your own community to do that as well? And then leverage your talents. 'cause sometimes, as we all know, it's not always about what you do, it's about who you know, what your connections are. And so the other things that you need to do in order to be good at your job. Okay. Yeah.
So many good gems. Just in like that one minute.
And I'm curious because you got to multiple director levels, like you were up there in corporate. So I'm curious, when you talk about like you, it sounds like your passion is really, um, helping women especially navigate their careers in corporate America.
What was that experience like for you for. Yeah. For someone who probably started wherever you started and then getting to director level? Yes. So I definitely started out I graduated from college with a degree in human resources, so by the time I went through school I kind of knew I wanted to go in that direction.
It probably helped that I had done. What I would call leadership development for junior and senior high school kids in a state program. Mm-hmm. Called Maryland Leadership Workshops. Probably helped that I was an RA in college. All of those things kind of said, oh, I have some skills in this area, working with people.
What should I do with that? Mm-hmm. And I literally kind of looked through the, um, the job circle of things that would lean into my talents, and that's how I got there because I had a strong, like for math, believe it or not. Mm-hmm. And for law, which you're like, how did you get into hr? And I was like, it is solving complex problems and people are the most complex.
Thing out there. And so it is thinking through like a calculus equation and to kind of look at, has to equal either, uh, productivity or retention of people or revenue for the company. Like there's some output that has to happen. So solving people problems and helping people grow really does add to the business, right.
So I actually kind of found my way here and I did start working my way up and that's when I started to learn the other thing that just being good at what you do wasn't enough. Working hard. You know that myth, if you just work harder, people will notice and you could promote it.
That's not enough. Yes, you need to know your stuff. Yes, you have to come in and do work hard and do a good job, and you have to build relationships and you have to understand the nuances. Of the, what I call the game being played outside of the, the reason for the business being, right? Like there's, we do something like we give cable services, we provide a store where people come do it, get some, do it yourself stuff.
All of those things. Or we fly airplanes and we get you to your destination. All of those things are what the business is. And then there's the other stuff that's going on, which is the. People moving around and trying to better themselves and take advantage of opportunities. So there's this whole, how do I get ahead game that's going on too, right?
Mm-hmm. And so paying attention to both of those things is what becomes important. Okay.
And you know what I, I love that you equated it to like complex problems and like Yes. How ultimately the business wants like higher revenue or higher productivity. And you know what I'm curious about because, you know, like I know you personally.
How do you add like the, the human and the heart aspect of that? Because when I think like higher level execs who are just like, oh, it's all about the bottom line and the revenue I don't think that they're thinking about relationships or the, the people or whatnot. So what has your experience been in navigating that?
Or maybe I'm just mistaken in how I am perceiving these? Oh no, it is about helping people understand that there's research. Around engagement and getting that and you'll probably see lots of articles about most people aren't really engaged and aren't really happy with their job. It's a very small percentage, but paying attention to it absolutely makes a difference, and when people give incremental performance, when they're doing just enough to get by versus when they go above and beyond because they feel really connected, there's a difference. Yeah. And there's so much work about how psychological safety people feeling included, that they can say and contribute, that their ideas will be heard.
All of those things drive engagement, which drives the bottom line. Mm-hmm. So it's actually building a business case for people to see. And it's like the, the human resource leader, me, had to learn to talk the language of dollars and cents and these activities that I'm suggesting. They're not about just holding hands and making people feel happy to be here.
It is about driving business results and understanding that having people be happy to be here is really good for business. Mm-hmm. You know, and it's like, it's common sense, but it's not always so common. Yeah.
And you know, what I'm thinking about too is like, it's not just the executive level that I'm just gonna speak personally.
Like I know early on in my corporate journey in my career. I was the kind of person that was like, no, I just wanna get things done. It's all about success and the metrics. And so I think my next question isn't just for people who are like in high leadership roles, but also just at the individual level.
How do you bridge that gap? So you, you have somebody, whether individual contributor or high level exec who's like, no, I don't understand what you mean. It's all about the result. It's not my fault if people aren't motivated to do their job. And so I think the thing is, is that I remind people that people like to work with people that they like.
And when people have a respect for you as a leader. Then they're going to give you more. And so I go back to people just doing the necessary part of the job and checking out at five o'clock versus a person who will stay longer and help that customer or help the other teammate get something done because it makes sense for the business to do that.
Mm-hmm. And people make those conscious decisions every day based on their leadership, the people that they work with, if they feel the place is toxic, if they feel the leader doesn't care. Then they're thinking, why should I care? Mm-hmm. Now, it might not be an obvious thought. It's that subtle thing that happens in your brain when you kind of, you know, take in all the information around you and your brain's like, oh, well protect yourself.
Just do what you need to do to get by. And maybe start looking for something else, and sometimes those leaders that are just like, it's not my fault, are the ones who are most convinced by the numbers. And it's, this is the business case is the important thing you do.
And it's like always talking about what's return on investment at this time. I remember I had to explain to my chief financial person in one of my my business units. Why it was important to get cupcakes for breast cancer awareness. And the thing was, he understood that because he came to me and said, you know.
Help this person who wants to get cupcakes, help her tell me why this is good because I'm not getting it right. And so then I talked about what the return on investment was, what was driving awareness, what would help maybe with medical cost and how it would increase you know, the visibility of our, our company and our business for showing that we cared about this topic.
And then so he is like, okay, great, thank you. You know, and it was just like, he was like, 'cause buying cupcakes does not make sense to me. It's like, mm-hmm. It's not about the fact that it might only be a couple hundred dollars. It's like, it's not a worthwhile investment. I was like, it's not about the cupcakes, it's about the cause and it's about getting people to come in for the message and getting people to come and care and getting people to sign up to do something different.
That's what it's about. Okay.
And you know what I really just got from that example is that it sounds like this, the CFO, I think you mentioned Uhhuh felt safe enough with you to ask the question and Yes. In this time that we're in right now, I feel like it's a little a little bit of a touchy subject sometimes.
So I'm curious what is it about you or how have you basically cultivated relationships so that people, especially those in higher level positions like the CFO, are not afraid to ask the question that they feel they're gonna be judged for? Um, you know what, I think I've intuitively always felt something about creating psychologically safe spaces for people.
I wouldn't have known to call it that early in my career, but I did know something about confidentiality and trust and perhaps so that people would. Would be honest with me. And the thing was, is I was much more effective at my job if I really had all the facts. So if there was stuff hiding behind the, you know, the information and I didn't have that information, I wasn't necessarily gonna be able to give the best advice or the best solution.
And I always liked to have things back to that math background. Always wanted to have it resolved, you know, like balances out. Mm-hmm. And have the equation work. And I think that, always making it safe for leaders to say whatever they need to say and not judging, right? And so people would say things to me, and sometimes it would be hard, but it's like, okay, I don't have to agree.
I'm a space for the information to flow, and I can have an opinion about it and I can respect. That their opinion is different, that their thoughts are different. So there's a little bit of of cognitive dissonance, right? That might occur. But I can be comfortable with that tension and I think that was just one of my superpowers.
Mm-hmm. I can be comfortable with the tension of us being on total opposite sides of the table and having full respect for your opinion in the space of not agreeing with you. And I think that just, that was just an enabler for me to be able to talk to people about anything and everything. Okay.
I have kind of like a possibly controversial question, but um, like I said before we started recording, I'm like, you know, my intention little listeners may not know, but I always ask when I have a guest, it's like, what's your intention for the call?
And my, because I know Cherie, I've known her for like, I don't know what, five years now? Yes. That crazy. I was like, no, we're gonna, we're gonna shine a light on things. 'cause I think it's really important. So. In your bio you mentioned that you were not just in DEI. You were like leading it, I believe.
I don't remember exactly your position. Yes, yes. I was head of De and I, head of d, e, and I. Okay. I would love your take on. Okay. There's the person who was fed up and is like, of course it's important. I don't see anybody who looks like me, C-Suite. And I don't understand why. You don't understand why that's a problem.
So there's that. I would love to hear your take on that person. And also the person's like, I genuinely don't understand why it's important, so Ooh, yes. Yes. Could you please speak to both of those? 'cause I think it's really important and you have a unique ability. Listeners, you don't even know, like Cherie has a unique ability to be calm, grounded, and kind of like be that bridge, that calming bridge that we really need these days.
Yeah, it's funny 'cause I had one of my best friends in high school was like, why does there have to be a black student unit? I don't get that. And um, and she was not black. And um, and so we would talk about things like this and , when you make decisions around the business, you have a lot of information, but you also have the context in which this is happening.
And we have a context in our country around. People being different. So we are built on capitalism and we're, but we're also built with corporations that were built by and for white men, right? Mm-hmm. And really until. World War ii when women went in to back up there, there was really not that role of women in the workplace the way they are now.
And even if you watch like Mad Men or things like that from the fifties, it was like, the role's really limited. You're admin, you're a teacher, you're this mm-hmm. And so to now see, uh, women and other people come the workforce in different ways, right? And so I think there's the fact that things have moved along and they're very different, and systems and structures haven't changed.
While the situation has changed. Mm-hmm. So there, there are people who have a lot of biases and thoughts about who should be in the workplace, who should have advancement opportunities. And one of the things that can trip people up is that they're looking for people like them. And when they don't see people like them, they're questioning.
Now it's a fair question because you're wondering, is this company really. Truthful about their take on diversity, about their take on equality, and then we have a little bit of a backlash going on around how DEI hasn't supported everybody. If that's your thought, then you don't know what DEI really means.
Mm-hmm. And there's been a definition, which means that it's just letting black people and women in, and that is not what it is. Inclusion has always meant everybody. There was no, there's no way to do it without everybody being in, there's no leaving white men out. There's no leaving anybody out if you do it right.
And the thing is, is like even if you have a room full of people that look the same, if you don't have diversity of skills and talents, it's gonna be very hard. So you're gonna need someone engineering, you're gonna need someone in finance, you're gonna need someone in hr. You're gonna need someone in marketing.
That's still a diversity of talents and skills. And if you recognize. That you need that, then you start to look at other people bringing their experiences with them. And because there's a diversity of experiences that only adds more talent, more possible solutions, more brain power, different types of thinking, and when you need to be innovative, and I can't think of a business that doesn't need to be innovative, right?
Because with technology moving as fast as, as with everything, there's no business that really can say. We're good for the next a hundred years. We're just gonna keep doing everything we've been doing. And so if you're smart and you're savvy as a business person, you'll understand that groupthink is not gonna have your business move forward.
And so having a team of people that look just like you, that are all just like you, that have similar experiences at you, is not going to add mm-hmm. Um, diversity of thinking and get you someplace as quickly as if you had. A diverse team. And I'm not saying that just 'cause I believe it. I mean, there's a lot of data out there about businesses that do better because they have that.
And I think the people that don't understand the point is that they're missing that because we hadn't been intentional about it. It wasn't just happening. Theoretically, if you hire all the best people, theoretically if you do that, you should have a diverse team. The issue is that people overlook people that aren't like them and they don't understand how their own brain works.
So if you really get into, you know, thinking fast and slow, if you really understand how your brain takes in so much data makes shortcuts, then you would understand that when you have quick assessments of people that it's not necessarily true, it's your framework. And that you probably need to go them.
So you can't say all women this or all men that, or all people of color this, or all, uh, Jewish people this or all that. Those are just frameworks. So when you meet someone who is different than you, your framework might give you some information, but it's not the truth at all levels about that individual.
So it's about getting to know the individual. Okay.
You just said something about, you said a few things that are powerful, but I just wanna get to, like you said, that you have this framework that may not allow you to see somebody who has really great talent. Right. I'm curious, how have you worked with clients?
'cause I know you've worked with individual clients and teams also. How have you taught them or encouraged them to become more aware of the framework that they don't even know they're working with? Yeah, well, so I've had this talk about bias with people a lot, and it's like when you really break it down to how your brain operates with the millions of data bits, points that come in every second, there's no way you can process that.
So you basically have this great computer in your head that takes all the stuff, files everything, and will make shortcuts. Otherwise, you'd have to wake up every morning and learn everything you know, all over again, right? Mm-hmm. So it's important. And one way I show people that is, I'll take them through a visualization and I'll give them some data points and I'll say, imagine this.
Imagine that, imagine that. And then I'll go back through and say, well, who did you imagine? And just from that experience, people can go, oh, my brain automatically saw this. My brain automatically saw that. And so. In my mind, this is what I think of. And so if I'm looking for a particular person to be this, I may not look and see all the other people who could also fill that role because I'm so used to seeing it this way.
And you forget. Well, where do you get that from? Well, you watch movies, you watch tv, you've read books. You've grown up in a place where it's always been this way, you know? So if I say married people, most people think of a man and woman that are married. Celebrating the anniversary. They don't think that it could be two men or it could be two women.
That's so true. Or it could be something totally different from that. And that's, and that is the part when you go, oh yeah, okay. My brain jumps to assumptions. My brain uses a framework, so I need to understand that it's not the truth. It's a framework. And then I can open myself up to who is it that's really in front of me.
Okay, but it's, that's being intentional, right? Yeah. This is huge. Now I wanna go back to, you mentioned early on when we talked about like what was, what was really important to you. You really wanna work primarily with women, how to navigate corporate America in a system that necess doesn't necessarily support them.
And now you basically. Talked about why? Because there may be some implicit bias, I think is the, the term Yes. Frameworks that people are working with. So you just spoke about how somebody in the leadership role can become more aware of that and not have that bias be their, , primary framework.
Now what about, or the woman just acknowledge that they have a bias, right? Because biases aren't gonna go away. Right? That's just how your brain works. It's knowing. And it's not even just, I mean, biases affect everything. There's several different ways. It's, it can affect your decision making. There's cognitive bias, there's data bias, right?
There's confirmation bias. It's like confirmation bias is probably even bigger problem. Mm-hmm. Because you only see things that support what you already. So if you think there's all red cars, you're gonna notice all the red cars and that's fine. 'cause there are a lot of red cars out there. But then there are blue cars there.
There's even occasional green cars, you know, black, silver, white, and so, but that's again how your brain works. So if you have a point of view that this is there, it's like we don't need to beat ourselves up for biases. You know what I say? So I say, no blaming, no shaming. We've all got them. It's learning to work with them, you know?
Mm-hmm. The simple bias, it's like, this is another one that people get. It's like, oh, if you flip a coin, it's been heads five times. The next time sure. Should be tails. That's not how that works. It's not how probability works. It's a whole thing. Right. Yeah, but we think that because of, for sure it's it's turn, right?
It's, it's happened so much. The odds are there. Yeah. It's like, okay, well please don't go gamble if you believe that.
You said something really powerful. The systems and structures haven't changed, but the situation have changed.
So let's just take, um, women and people of color, right? Uh, those with disabilities like a, anyone who's like a minority. Yes, it is true that the systems and structures haven't changed. Now, if I'm somebody who's coming to you and I'm like. Cherie, but I'm never gonna be considered for the lead position.
That's actually kind of a bias as well. So can you talk us through how do you navigate that? The difference between, okay, there are things that are true, but then how do I not kind of internalize that? Ooh. I think that's the trick is to not internalize it. Right? And to not let that hold you back.
Because if you also believe that because I'm a woman or because I'm a person of color that I can't advance or I can't do that, then that'll affect your performance. And I will wanna call out. It's like you have to keep pushing for things. 'cause eventually we had structural changes. We don't even think about it now.
But now there's dips in the sidewalks for wheelchairs to get up above the curve. Can you imagine there was a time when that didn't happen? There's usually a ramp to get into most buildings with stairs, at least government buildings, right? And there are other things like that. There's usually a handicap stall in a bathroom.
And so there have been some changes. That have, you can see from a structural standpoint now, it does still impact people with work.
There are people who think that people who are differently abled aren't as capable of doing a job. Well, it depends on the job you're talking about. Mm-hmm. If the job using their brain power, the fact that they're in a wheelchair has nothing to do with their capability.
And so I, I think it's also making sure that you don't hold yourself back because someone else has a bias. You know, there was, um. Recently in the news, it's, you know, people believe things. A a, a leader in our country made a point that civil rights had been harmful for white people.
And sadly people might believe that without checking the facts. Right, because it becomes a feeling. So it's a bias because you have a belief that something happened. I was like truthfully.
Yeah, white men are like 30% of the population in the US and hold like 80% or higher of CEO roles in the Fortune 500 are probably 70% of the leaders across our government.
So I failed to see how there's been disadvantage. Now I will say, if you wanna look at college enrollments and things like that, it's probably lower. But there's a fact behind that called not as many are applying as women, way more women are applying for schools. You know, just overall. So you might see a little bit imbalance in there.
Um, but that is a factor of not necessarily people being held out, but people not even applying and putting themselves in the pool. Mm-hmm. So I think it's like starting to look at data.
And so if you're a woman or person of color, or both of those things are true for you, it is looking at yourself and saying, do I harbor an unconscious belief about this?
Because internalized oppression is a thing. Hmm. Internalized racism is a thing. Internalized sexism is a thing. Internalized ageism or ableism are things right, and it is a matter of understanding that your brain has been processing all that data. And so even though you might feel strongly about your capability, you may have a suggestion in your brain that says, oh, women should take care of everything at home.
Or people of color aren't as qualified. And even if there's historical reasons, like, okay, there's a point in time where, um, during slavery, people weren't allowed to learn to read and write. And so there may have been some lingering. And so as, as things changed and education happened, there was an opportunity to catch up, but there hadn't been a culture of education for a long time.
And there were also context in which people were preventing them from leveraging those new rights, called Jim Crow laws called KKK, called, you know, militarizing, a police force. All of those things started to, interfere with that growth and that capability happening. So context is important.
For understanding maybe how you got there and then doing your homework to let go of your own biases so you don't hold yourself back. Mm-hmm. And then start to look at the context of the environment you're choosing to work in, and then, finding out if it's safe enough for you to point out the challenges and to do something about them.
That's so good. I, I just got like a, a three step . Process to start, uh, let me know if I ca capture this correctly. So for somebody who may have been like, oh crap, like I think that's me. I have been holding myself back. It sounds like, uh, you never said go judge yourself harshly 'cause That's right.
Yeah. It sounds like context, right? Like gathering context on how you might have, uh, gotten that, those beliefs. Yes. And then homework to start letting them go. And then. What is the context of your current landscape and is it safe for you to speak up?
Now I wanna dive deeper into the, the homework to start to let go.
Yes. How, what does that mean to, for somebody who's like, I, I don't, I don't understand this is something I've held to be true. How do I start the letting go process? Right. It is a journey. 'cause it starts with your thoughts and you have to start examining your thoughts. And it's like, okay, well I've watched movies where, women have been taught as less than, or we are made to believe this. But is that true? No. I've seen examples of women in government. I've seen examples of women CEOs. I've seen examples of this. I look at my own capabilities and I look at the guy I work next to, and I am as good as him, better than him, stronger than him.
You know, all of those things, you start examining the facts of your life and you start letting go of this is not a true belief, and how do I replace that belief? Sometimes affirmations are helpful for replacing your belief, but they really take every day, and I'm not just saying, doing a power pose, they're actual thoughts you have to do every day to kind of do that.
And remind yourself of who you are and looking for evidence and then making the decision. It's like, okay, this is this is something I learned through socialization. It is not a fact. And I always remind people, it's like, yeah, everybody used to believe the world was flat too, didn't make it correct.
And so because people have believed this for a long time, and society has an expectation, like we're hearing now, people are like, oh, women, like your greatest job is to be a mom. Or to have children says who? Oh wait, a lot of men, people that can't have children mm-hmm. By themselves, you know, they need someone else to help them out for that.
So it's like, is that true? I don't think so because there are some people physically who can't do it. There are health reasons that people can't do it. There are other reasons that people can't have it or they've had, they haven't been in, in the relationship they want to be in, in order to do that.
And so that's not a universal statement, that's an opinion. Aha. That's so good. That's an opinion. Okay. I would love, so that's such a great example with a, you know, the greatest. What do people say the greatest job a woman can have is to have kids? And especially for somebody who medically can't.
Right. It's not a universal truth. 'cause then it's like, does that make them less of a woman because they Yes, they can't. I would love if you could give an example, because I know in the context specifically of career leadership you know, since this is the pivot point, can you give an example of what might be an opinion.
Posing as a universal truth in somebody's mind that you've seen with your clients or maybe like even in your own experience.
So one of the things I can say that I've seen is, is that sometimes women and people of color get less room for making a mistake because there's an opinion that they're maybe not as strong as, and so when they make a mistake, it's like, oh, see, I knew they weren't as good.
I knew that. Versus looking at themselves and saying. Well, we've actually given Billy Bob about 10 chances to do the same thing. Billy Bob. Billy Bob. Okay. Just to make the point. I like it. You know, and I think we don't see that. And as an HR executive I saw that happen. So those patterns that I saw, I had a leader interview three people for a job.
The first candidate. Was clearly top white male. Wanted to offer him the job at a certain salary. He turned us down. The second candidate was a black male. Not a strong experience, but real good experience. But he went to the third candidate who didn't have nearly any of the experience, was junior, and went there and I said, this is when we need to have a conversation.
Maybe the second guy admitted to being a serial killer, and that's why he skipped over. Who knows, right? There might be a good reason. You can't just say there was bias or discrimination. I don't know. Or maybe there was, um, an unrealistic expectation of salary. But the thing I said is that this would require a conversation, and this is how we build our muscle to catch our biases.
Have a dialogue. Look at what happened. Another example same place. We had interview teams and one of the women came to me and said, I just wanna call this out 'cause I saw this, is it me? But they would talk about the candidates and she said, the moment they would talk about. But women, they were like, she didn't smile, she didn't do this.
She, you know what I mean? So it's like the expectation, but it wasn't the same when they talked about male candidates. And so the team talked about it. It's like, what was the role capability? So it was like, how do you go back and have a conversation with this team to point out, we are doing this, and it's because we've been, so there were men and women on the, on the team. So it wasn't just that it was a guy doing it, right? Like, so we, we don't wanna blame it. We all have biases. Mm-hmm. This is all of us. And so it's not shaming, not blaming, not pointing fingers, but knowing that, ah, let's do a bias check to make sure we're not making a bad decision here.
And again, it's not only around race, gender, and other things, it's around your decision making, how you look at data, how you look at things. There are different ways our brain tricks us. And so learning to have, a muscle around looking at this and challenging your own thoughts is really helpful and really healthy.
And again, even for the internalized things, it's especially helpful then go. But is that true? Is this just one of those things that everybody says, but there's really no basis in fact, or there's just societal conditioning? And right now, as far as women are concerned, there are a lot of resources available around understanding the socialization of women and how patriarchy affects us.
And, and to be fair, patriarchy's not even good for men either, right? There's a lot that can be unpacked there, but we don't have time for all that. But there's a lot of resources that people can find and read and learn a little bit about. And I find that there's so much that can help you. Understand the socialization and how, sticking with the status quo becomes normal.
'cause the moment you rebel a little bit, you get labeled a certain way. Mm-hmm.
I was development session the other day and the leader pointed out in communication, that it's okay for men to be a little bit more aggressive in the conversation, but what happens when a woman does it?
You know, what kind of label does she get for being a little bit feisty? And it's just that kind of thing. There's an expectation that you're supposed to behave in a certain kind of way. And if you don't do that, then you're either too aggressive, you're, something else. Or if you're too modest, then you're not gonna be a strong leader.
And so it's like, okay, how do you win? Mm-hmm. How do you win? And I think it's understanding those things. So that you can talk about them and not be afraid to show your capabilities and your strengths. Okay. You just answered, I was gonna ask like, how do you navigate it when you've noticed and it, you just answered it.
It's like really to understand it so you can like confidently speak to as it's happening. Right. Right.
People have been say, oh, so it sounds like white men are the problem. And I was like, no, it's systems and structures. 'cause throughout history, there've always been white men and white people that have wanted to make a difference.
You know, even through slavery. Think about abolitionists. You want to think about who ran the Underground Railroad, right? Like it couldn't have just existed, right? And so I think this is not about, calling men out, calling white people out. It is understanding that all of our brains work a certain way, and if we're going to have a difference, we need to expand our thinking and our points of view and learn how to do that.
And I think I'm sad because I feel the current leadership is less about that and, that doesn't help us unite as a country. And I feel like that, that we have a, a global opportunity to have a strong presence and I feel like we're missing that right now. And again, it goes back to biases. If we understood them, we probably wouldn't be doing that.
Yep. Amen. Amen. Yeah.
I'm curious, as you have risen the ranks because you I'm sure you didn't start off executive, but you ended No there executive, you know, fresh outta college. Um, has there been like a difference that bias has played whether internally or externally that you've seen? Y for me personally, yes.
Or even as, as you two, as you talk to like your clients or like different teams, have you noticed a difference at like, uh, I dunno, worker B level to executive level? Are, are there differences? Is it the same? Um, no, I think there are differences. I think in some companies it actually, the moment you cross over the line into director, it's like a different game being blade, and I think that I think when you're. In the entry level working your way up, I do think it is your skillset that gets you noticed more being a good worker. You still have to make friends. You still need to network because that does make a difference 'cause other people recommend you talk about your work, those types of things.
But I've seen discrimination at all levels. I've seen people be judged more harshly for being a woman or being a person of color. I've seen people get fired that were women and people of color, where the same thing that Billy Bob did about five times and he never got even a written warning.
And again, as an HR leader, I had access to information and I was involved in those things so I could see it. I wasn't just making it up, you know what I mean? You mean more at the higher level? You've noticed it more? I would definitely say that. I think there's less room for mistakes at the higher levels.
Mm-hmm. Definitely think so. And, and to be fair, it depends on where you're working as well too. But I mean, I've had a career in a variety of industries and so I'm just kind of summarizing overall. And I think it depends on the leader that you're working with. It's not necessarily a standard of a company.
Most companies would say they had certain beliefs about getting the best people and doing all of that. But then some leaders would have their biases. Impact who they thought were the best leaders. Right? So that's how it comes out. Again, if we were just gonna hire the best people all the time, we'd have diversity because I believe that we would be actually hiring the best based on what we saw and capable, because we will learn how to manage the blinders that our biases put in place.
Mm-hmm.
So I wanna switch a little bit to your own journey because you, and I'm sure some of the listeners might be feeling this way. You make it really high up in corporate, but that like you were director level, like Yeah. In many of these places. And then you decided, decided to shift, say that again.
And a vp. Yes. And then you decided to pivot and go into your own company. So I'm curious if there were any thoughts of like. What the hell am I doing? I've worked so hard to get here. Or maybe, maybe not. I'm curious because I am sure there are some listeners out there who feel like they're in the top of their game, but they're feeling some kind of way, like a calling to pivot.
Like how did you navigate that? Tell us about that. Yeah. I think there's a point where I figured out that I was, I felt like I was maxing out. Like I felt like I had the capability to go further and I was maxing out and I remember being in one company and, and discovered. That there had been a lot of undermining going on because there was a, a particular male who didn't wanna compete with me and had given all kinds of stories in the corporate office.
'cause he had more relationships than I did. 'cause I was kind of new to that company. But I found out about it, right? Mm-hmm. And it's like that kind of, that, when I say there's the nuances going on behind the scenes and then there's the business, you know, it's that type of thing. And having that experience, I was like, well.
This will probably continue wherever you go. And I've seen it in several companies now, or I could do something different. And so when there's when there's a change, there's an opportunities. Do I wanna just look for another job or do I wanna try to do this on my own? And I made the decision, well, let's try to do this.
I see other women being successful leading coaching practices. I've seen people get out there and do it now. It is hard. You know, I haven't, I haven't achieved the level I'm aiming for yet, but I've been learning new things as I go because operating as an executive in a company and then running your own company are different skill sets.
So where I was strong in my function and deep in my experience, I not a marketer, I wasn't a CFO, I wasn't a salesperson, and now I'm doing all those things. So I'm adding new skills to. My toolbox. Right? And so I'm learning those things. I've taken some course in those things, and I continue to enroll myself in some things.
And then I join a business group to get some advice, like have my own little board of directors. And so you start to invest in yourself in that way so that you can build a business that you want. So I'm in the middle of my pivot, like I pivoted and I jumped in. So I'm swimming. Mm-hmm. Trying to keep my head above water and I know how to swim, so I'm confident that I'll be able to move to the deep end.
Right. But it's like having that confidence and that building willingness to risk and take a chance on you. It's like, I have skills, I can do this. Oh, I don't have these skills, so I'll have to add that in. Oh, I need to go learn how to do that. Okay, great. And I need to learn how to do that. Okay, got that.
Let me ask some people for some advice. Mm-hmm. And so I think it is knowing that even though you're a solopreneur, when you start out, don't be alone. Go meet people, go get advice, take classes, join a community of other entrepreneurs, that type of thing. And I think that is what keeps you going.
I love that.
And for anyone who's like, I could use Cherie in my company I can use Cherie to help me in my leadership. I am maybe like small business owner or in corporate really looking to educate at the leadership level. 'cause Cherie like the work that you do, I've said this to you probably since we first met.
I don't know if you know this Cherie, but literally like the first time we met you were talk, you, I wasn't even in the conversation and you're, and you were talking about like. I'm very passionate about de and I and like I really just believe that in leadership, especially there's systems in place that we have an opportunity to change.
I was just like, I don't know who she is. We're gonna work together. We're gonna partner. I never told you that. I don't think I ever told you that. You too. Yeah, because truly I'm getting goosebumps. Your work is so important. It's so needed. Especially right now. Uh, yeah, we're recording in America, especially right now, and for anyone who is feeling discouraged and they're just like.
I hope you're motivated by Shere the good work that she's doing, that you're not alone. Yeah. So for anyone who's like, I wanna work with Sheree, I wanna be in her energy, in her vibes, I wanna, I want her groundedness. I want a safe space where I can ask questions that I'd be judged for. Yeah. Right.
That's a huge skill. I don't have that skill, let me tell you right now. But Cherie, Cherie has that skill. How can people connect with you? Oh my gosh. Go to my website and, and. Click on a complimentary ideation session and let's just have a conversation and see where it goes and see if there's a good fit.
That's a great start. Um, the other thing is to link with me on LinkedIn. And that's another good place. And then we can message if need be to do something else. But it's, it, there's all kinds of capability. If you're wondering what we can do, well, I do leadership development training, I do executive coaching.
And a lot of times I do that as a big project. So I had a great client that I did leadership develop. Then we did one-on-one coaching with all the leaders and we gave some on the job experience homework to reinforce all the lessons. So that's how you get true transformation. So it's just all of those things, any of those things, and I love to do it.
I love it. And don't worry, listener, I'm gonna put this in the show notes, but Cherie, what is your website? Just so anyone who's listening Called Ball Company. There you go. Amazing.
And then one last question that I ask all my guests. Before we wrap? Yes. The most important question, it's not if, if you were an item in a coffee shop, what would you be and why?
And you could be a, you could be a drink, you could be a pastry. Somebody said security camera, somebody says sticker. You can be literally, literally anything. What would you be? I'm kinda liking the security camera. That was really,
gosh. Let's see. Um. I think I'm gonna go with the espresso machine. Okay. No one's said that yet. Yeah, because it's like, it's like I help make the drinks right. Better. And it's like you bring it all together and it's the enabler. For having the drink that you want. And I think that's yeah, I like that.
What an interesting question. Like coffee shop, I, my head went all over the place. I was trying to think about what's my favorite drink, you know what's funny is when I came up with a question that was my that was my thought. Like people are gonna say either drink or maybe a pastry. But then I think the first one somebody had said like.
The sticker and I, I'm like, wow, this is amazing. The creativity. I like that you're gonna be the espresso machine because you are the one how fitting, you're the enabler, you're making things happen. Yeah. Yes. I love it. Cherie, this has been so good.
Listeners, like I said, you have just been given a treat and, uh, what's your one final takeaway that, or that you could say to the, the listener?
Oh my gosh. Let's have a chat, click ideation session, and come on. Let's get started. Let's get it. Awesome. All right. Thanks again, Cherie. All right. Thank you.
Big thanks again to Cherie Caldwell for sharing her story so openly. These conversations are such a reminder that no pivot is too messy, too late, or too unconventional. If something she said resonated, don't keep it to yourself. Share this episode with someone you know who needs it. And when you are ready to start your own pivot, head to www.leadintact.com for free resources or book a free 20 minute call with me.
I'm here for you.