Kerry Cicero: From Survival to Leadership: Building Teams That Thrive
An excerpt from the Fortune's Path Podcast
"How do you lead effectively when you've never been taught how to lead? What happens when you're promoted to manager, but no one explains what that actually means?"
These are the questions that drove Kerry Cicero to write "It's Simple But Not Easy: A Leadership Guide for New Managers and Struggling Leaders." In this powerful episode, Kerry shares how losing her mother at 16 and growing up with six brothers in a chaotic household taught her the resilience and empathy that would later define her leadership style.
The Reality of New Management
Tom: "So some of what I got out of it was certainly imposter syndrome. You talk about people coming into a role where they're not prepared, there's not a lot of structure in their organization to help them out. There's just the expectation of you're a leader now. You must know how to do that."
Kerry: "For years of my life, I was constantly looking over my shoulder going, 'Are they gonna realize I have no idea what the hell I'm doing here?' It's not even imposter syndrome so much as it's just—I don't know how it works. I don't know the inner workings of this organization. Who do I get to be able to figure out an easier path for my team? How do I advocate? What does that even mean?"
Leadership as Human Connection
What sets Kerry apart is her conviction that great leadership starts with seeing people as whole human beings:
Kerry: "I have to put my ego aside and listen to what they say and start to recognize, 'Oh wait, I'm playing a role in this relationship and I have very real power over this person.' And you cannot take that lightly as a leader... Very easily, very quickly, I can destroy somebody's life, or I can make them have the greatest life they've ever had."
The Power of Psychological Safety
Kerry advocates for creating environments where authenticity and performance coexist:
Kerry: "I create an environment on my teams where I allow people to express themselves. Because I believe that whatever emotion you have, you have a right to that emotion... The feedback I get from my employees—male and female, straight and gay, pick a race—is that they are grateful for my leadership. They're grateful for the ability to express themselves, to have a safe space."
Ready to transform your leadership approach? Listen to the full episode where Kerry reveals her framework for building "happy, engaged, high-performing teams" and shares practical strategies for navigating the toughest leadership challenges—from conducting empathetic layoffs to managing up in chaotic environments.
This episode is essential listening for new managers, struggling leaders, and anyone who believes that business success starts with treating people like human beings.
The Fortune's Path podcast helps service and technology business leaders address the root causes that prevent rapid growth. Find your genius with Fortune's Path.
Transcript
Tom: [00:00:00] How do you lead effectively when you've never been taught how to lead? What happens when you're promoted to manager, but no one explains what that actually means, and how do you create high performing teams while still allowing people to be human, even when that means tears in the conference room?
These are some of the questions we explore with Kerry Cicero, author of It's Simple But Not Easy, A Leadership Guide for New Managers and Struggling Leaders. Kerry is a former president and principal consultant at Canopy Consult. A leader in go-to-market, vision, strategy, and execution. She was also the senior Vice President of Marketing for Enable Comp and the Vice President of Marketing at HealthStream for nine years where we got to work together.
Kerry's approach to leadership was forged in the crucible of personal adversity, losing her mother at 16, navigating blended families and learning to survive in environments where she had to figure things out on her own. And she's our guest on this episode of the Fortunes Path podcast.[00:01:00]
Kerry, it is wonderful to see you. Thank you so much for. Coming.
Kerry: I love it. I'm glad to be here.
Tom: Let’s celebrate the publication of your book, “It's Simple, but Not Easy.” You're a very natural writer. I really enjoyed what I read and, you have a great story. When are you gonna write another one?
Kerry: When I have more time, maybe. I think that would be good. When I thought of the idea, I originally had several different ideas and I just couldn't decide which one to focus on first.
So in my head it was almost like a series of books not as much a series, like a Chicken Soup for the Soul type of thing. But just things where you. When you're a hundred years old, you have things that you've learned and dare I say, wisdom that you want to [00:02:00] share. And I feel like I have that on different topics.
We'll see maybe within the next year or two. It took me a long time to write this one. It took me a long time to find the time to write this one. The idea was born relatively quickly, but it took me five years before I started to put pen to paper. So we'll see what happens.
Tom: COVID is what got me to write my first book. For aspiring authors everywhere COVID was a gift.
Kerry: Yeah, absolutely. Absolutely.
Tom: But yeah, just like the habit of writing. Making the time for it. As you said can be tough.
Kerry: Yeah. I had to treat it like a job, I was lucky in that I wasn't working at the time.
And so I got up. Every day and I went to a coffee shop and I would write. The goal was to write 10 pages a day. That was funny. That's a lot. Then I realized, oh, 10 a day might be a bit much. So it was, the goal was 30 a week. And and I did that for almost every week until I finished.
Tom: That’s awesome. Did you have an editor?
Kerry: I did. I hired a local editor. I'd met with a friend who. Knew a friend that was an editor, right? And I met with her years ago when I first had the idea. And she was [00:03:00] in my price point, and she has done success a lot. It was very successful.
And realize, and for the 90th time, I chose the wrong path. I should have been an editor because she makes an unbelievable amount of money now. I couldn't believe the investment it would've taken. $200,000 to have her help me. And I was like do you have anything else in the $10,000 range?
She recommended a woman that was starting out and becoming an editor, and her name's Caroline Segrest, and she was fantastic. And we she lived not too far from me and had done more of the. Nonfiction writing. Yeah. Which is what this is for me. And so yeah, we worked together and I'd written about a hundred pages before I connected with her.
Holy Cow. So then she, so I didn't want, I wanted to make sure that she would, wouldn't be waiting for me. Yeah. I wanted her to edit and as I was continuing to write, which that worked out really well.
Tom: And so tell me a little bit about the book. Can you what's your elevator pitch for the book?
Kerry: Yeah. So the book is really meant for people who are new to the business [00:04:00] world whether they're a manager and they have visions and ideas of wanting to be a leader or people that are in leadership new to it and maybe have been in it for, I don't know, one to five years, maybe a little bit more, and are just not figuring it out or maybe struggling.
That, that's who I was thinking of. And it's so many of the people that I have led who I can see what they've struggled with and what they. Needed to know in order to be effective or people that had come in as leaders into an organization that I managed and thought they understood.
And, which is great 'cause you have to have the confidence to be able to do this, but I was able to show them.
Maybe a different approach or a different path or a different way. And then you could see the light bulbs going off, “Oh, that's how you do that, “ or “That's why you do that way.” And I'd gotten a lot of really good feedback from my team members, and so I thought I could probably help some people.
I if I had this book when I started holy moly. For me, it would've made a huge difference. So that's, [00:05:00] so it's for those people that are just starting out that might need some help or have been doing it a while and haven't, it hasn't clicked yet. They're struggling in some way, I think.
So some of what I got out of it was certainly imposter syndrome. You talk about people coming into a role where they're not prepared, there's not a lot of structure in their organization to help them out. There's just the expectation of you're a leader now. You must know how to do that. And it's hilarious. For years of my life, I was constantly looking over my shoulder going, are they gonna realize? What's that? I have no idea what the hell I'm doing here. Or I wish there was somebody that had guided me a little bit more so that you just feel more confident in what you're doing.
It's not even imposter syndrome so much as it's just a... I don't know how it works. I don't know the inner workings of this organization. Who do I get to be able to figure out an easier path for my team? How do I advocate? What does that even mean? Like I didn't know any of that stuff when I became a leader, and it took me a while to learn it.
Tom: So I'll say this, I know a little bit about your biography and so I'm [00:06:00] probably reading into some of what I saw, but some of it to me rang a bell about marriage.
I'll just leave that hanging out there.
Kerry: Sure. Go ahead and leave it hanging.
Tom: Did you think at all a, about that in the process or that was like, that's, no, wasn't there at all.
Kerry: For me, it wasn't marriage, it was parenting. It was where it. It felt more aligned with that to me. Obviously I have, I was married, I'm no longer married. Haven't been married for a very long time. I think it's, relationships are definitely in there, but leadership to me is more akin to parenting a child than it is.
And I don't mean that disrespectfully as in Sure. Employees are children or that, 'cause that's not at all how it is. But and I treat my children. Like adults, more so than not, I was never one of those parents that coddled, that's just not my nature. I'm very loving, very affectionate, but I don't coddle.
And and they're now very strong, intelligent, capable women I think because of that. But yeah, to me it wasn't a marriage thing. I'm curious what the marriage thing was from your perspective.
Tom: So from my [00:07:00] perspective, it was something certainly about communication and trust and establishing a set of shared goals, shared vision for things.
And so in that sense it would say, okay, so certainly peer to peer relationships or you do talk a fair amount about managing up in the book. And, that struck me a little bit as like marriage type relationships.
Kerry: Interesting.
Tom: Yeah, this is just where my head's up because what I'm thinking about for my next book. And so anyway, I don't wanna read into it stuff that's not there.
Kerry: Yeah. No, it's okay. I feel like coming at this from the. A divorced perspective. Maybe I should have thought about it more in my marriage. I dunno. I dunno. But I agree with you. There is definitely parallels to a healthy relationship, marriage or otherwise about communication and, respect, trust.
Shared goals, all of those things. Absolutely. I do that today with my brothers, with my children, with my dear friends in my life. Of course.
Tom: So you have five brothers?
Kerry: I have six brothers.
Tom: Six brothers.
Kerry: I have six brothers and two sisters.
Tom: [00:08:00] Yeah. Holy cow. Yeah. So you have one younger brother in there?
Kerry: Two younger brothers. And two younger sisters. And then four older brothers or older brothers. And it we're a motley crew. Lots of parents among all of us. And so it's not, it's not a one mom and one dad by any stretch.
Tom: Are they still in Detroit?
Kerry: So I have a brother in Michigan in Grand Rapids and two, my two sisters live in the Detroit area. And then I have three brothers here. In middle Tennessee brother in Virginia. And then my oldest sibling passed away several years ago. Yeah. So
Tom: You had a line that struck me about, there's the time in your life, like before mom died and after mom died.
Kerry: Oh, yeah. Yeah.
Tom: And your mom died at 44?
Kerry: Yeah, I was 16 when she passed. And yeah. So she was young. As a woman in her, early fifties. 44. I would love to be 44. 44, even though mom's dead. I, so I felt like it was so old when I was younger, but obviously we know now that once you pass it, you're like you long for those days, but yeah.
So she was young when it happened, and, beforehand it's the, even though there [00:09:00] was chaos and craziness growing up there's no way it can't be when you've, your mother's married and divorced three times before your by the time you're 12. Yeah. Basically. And father is same thing. And it's just a, it's a bit of a maddening situation. Even despite that though, there's a level of security and comfort and, just knowing that you have when your parents are there. Yeah, my mother especially.
And then when that, when she passed it within a second it was gone.
And I had to move in with my father, with whom I did not have a relationship. I'd spent, my relationship with my dad was, phone call on Thursday nights for five minutes, and then Saturdays from 10 until four for most of my life. Had never spent a birthday with him, never spent a holiday with him, never went on a vacation with him.
Had no, didn't have that. And as he happened to marry a woman who didn't like children. And he had five children, so maybe not the best move on his part. And as gonna say, it sounds like a mistake. Yeah. Yeah. What are you gonna do? It is what it is. Yeah.
So when that happened, it just, the [00:10:00] person that I was just had to change into a different person in order to process and grow and accept and live, survive. It just is how it is.
Tom: It's such a armchair shrink, like 16 years old, you're moving into a new organization, your dad's family, and one of the members in leadership in that organization doesn't get kids.
Kerry: That's right.
Tom: And so you're there with how many of your siblings?
Kerry: Two of my brothers and there was a stepsister. She was okay. My step monster's child. That's what we referred to her as.
Tom: She didn't like kids, but she had one anyway.
Kerry: She did, yeah. To try to save her first marriage and that clearly didn't work. Yeah.
Tom: So there's four of you in there. How'd y'all get along?
Kerry: We got along really well. My brothers very close to all of my brothers. And one of them had actually been living there 'cause he was going to college by my dad's house. And so my brother Paul and I moved into the basement, which was an unfinished basement.
And we just were in the middle of the basement living there. And then. Took my dad about a year and a half to build out the [00:11:00] basement and create bedrooms for us and stuff. It was fine, but there was just this ever present tension in the house because she didn't want us to be there and they had to make sacrifices and it changed their trajectory.
And their relationship and their family, as you say. And it was hard, again. New high. I'm 16. I'm a sophomore in high school. So then I had to go to a new, I had moved from where we grew up and became, went to a new city, new high school as a freshman and then as a junior I had to do it again.
And to say you feel disconnected is an understatement. Yeah. But to your point. Aligning that or setting it up against what it's like to walk into an organization when you have a bad leader who has tremendous influence. Yeah. You gotta figure it out. But it wasn't my first time.
My mother had been married to some, not very kind people. And so you just, you figure out how you gotta survive. You figure out how you play the game.
Tom: So you open your book with a line about, most of us have had bad bosses. And you went through a few lines [00:12:00] about. What makes for a bad boss, but is it as simple as like a good boss is the opposite of a bad boss, or is there more to it than that?
Kerry: There's probably more to it than that. I think, a good boss can affect so many different parts of your life. Not just what's happening at work. Whereas a bad boss, in my experience, it's a work thing, and you figure out how to disconnect from that when you get home.
So it doesn't filter into your home life and into the other parts of, just your normal day to day living and the work life balance. But a good boss can positively influence those things and make you stronger and make you better. So I think it's a, I do think there's a differentiation there.
Tom: Well, a lot of people take their bad boss home with them and bring it into the family.
Kerry: Yeah. I think that's. For me. As I said, growing up in a situation where you had a lot of bad things at home.
I'm a queen of compartmentalizing. And years of therapy will tell me that's not the right way to do it, but it's what you do when you survive, and so I [00:13:00] have had bad bosses, and of course I take it home with me, but it's a different approach to having a great boss, a great leader that. Inspires you to grow and to do more and in a way that turns you into a better leader, a better person. A better mom, a better friend.
Whatever it is. A bad boss may inspire me to read a book on leadership on what not to do. Versus I'm not gonna bring that home. It doesn't inspire me to do anything outside of. Not let it focus me, not let it impact my day-to-day life. That's how I view it, because Interesting.
I don't like them to have that much power over me. I don't like them to have that much influence. If I've got to endure and deal i'll deal with it the eight hours a day that I'm with you. But the rest of my life I won't.
Tom: Are there some, so you had a definition in there of a bad boss that I really liked, which is basically it's someone you want to ignore.
They, you're not bringing it, they're not giving you anything that you're then taking into your life. And I'm curious about is someone who's a bad boss for [00:14:00] everybody? Or are they a bad boss only for certain kinds of employees? And the same thing could be asked of a good boss?
Kerry: Yeah. I don't know the answer to that because I, because it depends on them. How were they? Raised, how were they brought into the business world? What were they given by their leaders and their bosses? What type of employees do they have? I have, I made a lot of missteps.
As a boss, as a leader. And I realized that based on the reactions of my employees. Or sometimes you get somebody that comes in and the glass is half empty. Period. No matter what. It doesn't matter how hard you work for them. Those are really difficult people to manage.
Just if your boss is that way, it's a really difficult person to work for. If you have somebody where the glass is half full or the glass is never empty, then that's a whole different mindset, a whole different approach that can, how do you try to approach it? Definitely a more positive spin, I tend to lead with gratitude just because of it just [00:15:00] feels good. It's easy. It's really hard to be angry. I guarantee if you were to try to be angry, if you're thinking about a happy thought or a gratitude, if you're grateful for this home that you live in, and then you try to be like, but I'm really mad about it's impossible for your brain to do both. You just can't. So trying to have that gratitude is a real thing for me.
Tom: I totally agree about the idea that you can't be angry and grateful at the same time that they don't match. Your earlier conversation, you mentioned compartmentalizing. Have you had to lay people off?
Kerry: Oh, yeah. Yeah, for sure.
Tom: So you, it's, you're, you've talked about leading with understanding. And having. That it's like children in the sense that you want to love them and help them grow, see them achieve their dreams.
So how does that work in a layoff?
Kerry: You don't ever just walk into a room and say you're fired, right? If you're doing it right, you're working with them over multiple. Months of time, if you identify a problem that an [00:16:00] employee has, whether it's an attitude, whether it's performance, whether it's productivity, whatever it might be.
You have a real conversation with them and start with empathy. Are you okay? What's going on here? This is what I'm seeing. So the expectations are A, but I'm seeing B. What do you need to be more successful? What's going on here? You start to get to know them and understand maybe there's something happening at home or.
They don't have the skillset they need and they're freaking out about it. Or they do have imposter syndrome, or somebody else in the company is treating them poorly and they don't know how to handle it. So they take it out on the team, or, sure. Who knows what's happening. So I start there, and then I very quickly bring in other key departments, HR, first and foremost, of course.
I mean your leader, your boss, and then HR and I rely so heavily on them. You start there and do that, but then when it comes down to. Having that actual conversation of having to let them go, I've got a list of things of evidence, of proof, of challenges, and sometimes it's a [00:17:00] easy, quick, they're not surprised. Sometimes they're caught completely off guard, which is really, in my opinion, more on them. They're not paying attention, they're not listening. They're not. They have no self-awareness. They're not holding themselves accountable to whatever expectations have been put in front of them that have made it very clear, yeah. And, but even in those conversations, I don't walk into them blind. I do a lot of preparation because they're hard conversations. You are going to change that person's life for the rest of their life. They will never not remember this conversation ever. Ever. And so you walk into it knowing that it's not an easy thing to do.
It's a, it's one of the worst things you have to do as a leader. But in order to make it easier on yourself you prepare. You have to prepare for those conversations.
Tom: Now, what about when someone is let go? Not for performance reasons, but just because of cost cutting.
Kerry: It's the same type of a conversation in that you at least have to prepare and lay out for [00:18:00] them.
This is what's happening and this is why it's happening. And it's a, we're happy to be a reference. Here's a severance package. We fought hard to get you the best package. We're trying to set you up for success. Usually if it's a layoff situation, it's very different. But make no mistake.
Business is business. We're all replaceable. Yeah. Yeah. If a business decision has to be made it's gonna be made, and it's often out of my pay grade. Which I'm grateful for. I'm dealing more with the people that are performance issues than than not, eh, I have had layoffs of just because of cost cutting, but those are different stories to tell.
Tom: Yeah. So you've run marketing departments, you've run sales groups.
Kerry: Product as well. Product as well.
Tom: So tell me about those three different types of people drawn to those groups. So do you notice a difference in the employees in those groups? So do your, does your leadership have to change at all depending upon who you're leading?
Kerry: Yeah. The sales folks are more. Flexible. I would say they don't like the [00:19:00] regimented meeting schedules and. Deadlines and times like that. And I think that's because that's how they have to be successful, is they have to be flexible.
They're really dependent upon their client schedules. Not, they can say they're gonna do A, B, C, and D, the clients can totally change that. As a leader of salespeople, I have to be much more flexible. And I'm a Capricorn, I'm a type A, I'm a organized, responsible, I work within a very specific kind of process, and that makes me.
Comfortable. So when I'm leading people that are the exact opposite of that, it's ooh, okay, let me breathe through this for a little bit. Holy moly. But a great learning process. So they're, they tend to be very, if they're really good, they're very gregarious, very outgoing and.
Easy to communicate with, right? I, there are people that in my life that are salespeople that I don't work with and have never led that. We have some of the greatest conversations you're ever gonna have. Because they're just naturally really good at that product. People tend to be very inquisitive, tend to [00:20:00] be really deep thinkers and problem solvers and that's a different type of mindset. And marketers have a little bit of all of that, they're very creative, they're very gregarious. They like to solve problems, but it's in a, it's a different type of problem. They think a lot about storytelling and messaging, but have to be data-driven as well and business driven.
Different mindsets, but all very fun people to manage and to work with. There's been some doozies, but in general they're all really good people.
Tom: So it sounds like the answer to the question about do you have to lead differently depending upon who you're leading is No. That there's still the same set of principles that you're practicing about empathy, getting to know people, being supportive. Yeah. That stuff doesn't change. No. It's like the. Do you raise your children differently or do you have a set of values that you, I haven't figured that one out yet.
Kerry: I don't raise my children differently, I think I've taken enough personality surveys and disc assessment being one of them that you it reflected, and I speak to this in the [00:21:00] book that I am essentially, who I am at home is who I am at the office. It's, I only know one way to be, and that's how I am where some people are one person at the office and a completely different person at home.
And and there's nothing wrong with that. It's just different. And so when I'm thinking about how to lead a person my experience has taught me that the tenets of how I do that. Create a successful environment for people to be successful. Meaning I'm empathetic, I'm available.
I have a vision, I set a path I try to create. Yeah. What they need in order to be successful, going down that path.
Tom: You talk a lot in the book about listening and making the time to listen. I'm making the time.
Kerry: Yeah. For the people on your staff. That's the hardest part. Yeah. 'cause you can't get your work done.
Tom: That's right. And so that to me, you're. You had a story about you spent the whole day having, you didn't get anything done in the sense of checking something off your to-do list. But the entire day was spent and spent [00:22:00] in vital conversations. That's right. So you're exhausted.
It's emotionally exhausting. And it's it's also and I didn't get anything done.
Kerry: Yeah. It's exhausting, but it's fulfilling at the same time. If as a, for me being a leader is about. Making the people I lead successful. Period. If they're successful, then I'm successful.
So it's fulfilling in that regard. It's great to see an employee. Figure something out or grow or expand and know that you kinda had a hand in that, but you take no credit for it. Of course. 'Cause they had to do the work. I'm just the one kind of guiding 'em and moving them through it.
But yeah, there have been many days, especially when I was earlier in my career, when it, I. It was, it took me a little bit longer to kinda get from point A to point B. Now I can just kinda start at point B now. That's right. I've taken some of the work off of me. Yeah. In order to get folks there.
I have an employee right now who's 24 years old. And she's reporting up to me. And she's oh my God. And I have to [00:23:00] remind myself, okay, she's 24. She's 24, she's. Literally brand spanking new. And so I'm way more patient with her and spend a lot of time explaining what this means and the why and the how, and the what and all of that stuff, versus an employee that has been in the business for 10 years. I'm skipping all of that and we're just going to the, we're getting to the meat of it really quickly. So I do change my approach based on those people.
Tom: It seems tech has this perception about people being self-managing. And more or less “Okay, I'll give you the broad parameters and it's up to you. If I have to explain your job to you, you're the wrong person.” Tell me your point of view on that. 'cause you've worked in tech business, multiple tech businesses.
Kerry: Yeah. I've worked in a lot of industries. And I would say that there's an expectation that you've been hired to do a job and you need to do the job period.
Where I feel [00:24:00] like that idea of tech being, it being unique to tech I don't know that rings true for me so much. I think my reaction to that is more there's a level of management that is required. At all times, period. In order to make sure the team is successful, you're not building a business, you're building people. And if the people are successful, the business will be successful. I think that's like a Zig Ziglar statement. Or something like that. And so there's a pendulum of micromanagement that nobody wants to be a part of either as a leader or an employee.
But if you swing too far in the other direction, then you're gonna have, things are gonna take a lot longer, it's gonna cost a lot more money. It's not gonna be as successful. Every employee that I have ever worked with, myself included, appreciates guidance, appreciates a vision, appreciates knowing where we're going and how I fit into that.
I don't have to own it. In fact, I probably don't wanna own it all. But I need to know [00:25:00] my role in that and what's expected of me, how I get there. I may not need your help in telling me how I get there, but I need to know where we're headed. Let me figure it out. Let me get the team rallied and we'll get there.
And then I lead in that same way I. I need to go to there. You tell me how we're gonna get there. And that's actually the greatest part of leadership. Is because you get the opportunity to learn so much. 'cause I may say, I wanna go A, B, and C, and somebody else may come in and go, we could do this.
We could get to the same place, but I'm gonna go L-M-N-O-P. And to which I'm always like, “Oh my God, I never even thought of that. What a great idea.” And so then I'm learning. And what it does is it empowers that employee, that person to trust themselves, to learn and to know that they're capable of being strategic, of solving a problem of being successful, creating a business, whatever it is. And they build off of that. So I think self-management as a term is important. We all have to self-manage and [00:26:00] self-regulate in all of those things. But I think if you do not have guidance and leadership to keep you didn't, between the guardrails, I don't know that you'll be very successful.
Tom: Yeah. There are times when I'll just speak for myself. I don't know where I'm going. There's times when somebody said, what's your goal here? So I haven't really thought about it. I'm just doing things that seem interesting. And I think I'm not alone in that.
And I think there are businesses that also end up in periods where the, you've said. “What's your objective?” To raise revenue and cut costs. “Can you be any more specific?”
And a lot of times the answer is no. We don't know what to do. So in that sense I feel like there's times where it's very hard to give clarity to the employees about, or the people on your team about what are we trying to achieve? “The boss asked me to do this.”
Kerry: Interesting.
Tom: Yeah.
Kerry: Yeah. I think there are. I find it in my day to day. Excuse me, where I'm doing things because the boss is telling me I have to do it. And it's because he wants it. And okay, guess what? It's his company, right?
It doesn't [00:27:00] say Cicero on the outside of the door. It says Marshall on the outside of the door. So if that's what he wants, then that's, that's what we do. But I find that to be. Always for the purpose of some element of the business. It's either a part of our core value, it's a part of, it's not always about revenue and growth.
It just isn't. Sometimes it's because as a business, we want to be stewards of the community and so we're doing these things that cost us money, that take time away from building the business, but it's a part of our core value. And we're stewards of the community, so we do it. Or it's just a, you've had this happen when we work together.
In the past. I got an idea. Dunno where it's gonna go. Wanna flush it out for a little bit. I need you to go down this path and you're down that path for six months trying to figure it out. And at the end of the path, you've either discovered something great or you realize, yeah, we're no further than we were before.
But we have to explore it. You have to go down the path. But those are always one swim lane of activity. Whereas there's always four or five, 10 other swim [00:28:00] lanes that are about growth or about expansion or about innovation, other things that are happening. I've never ever been in an organization where there wasn't a destination and we are trying to figure out how to get there.
I've never had. I don't know if I would call it a luxury or a curse of, yeah. I'm not quite sure what we're doing here. We're just trying to figure it out. That would be crazy to me.
Tom: Have you been in a situation where the professed destination or strategy did not match the reality?
Kerry: Yes. And sadly.
Tom: What was, how did you deal with it? How'd you find out first and then how'd you deal with it?
Kerry: Yeah. I would say, when you're in those situations, I like, this is the situation I've been in where it's the most challenging for me. Is when you work for an entrepreneur.
And they have. 50 ideas and they wanna elevate and move all 50 of 'em. And you don't have the time or the capacity or the budget or [00:29:00] the people to do that. So what you end up doing is trying to do that. And so you do 50 things, eh, like that versus. Hone in pick five and do 'em really well.
So the struggle of that is requires and demands communication.
And I'm gonna be, again, I'm a type A, so you tell me, “Kerry, we need to go here.” I'm like, “I'm on it. Let's go.” And then if I'm going and we're not getting the results, it's my responsibility to tell the entrepreneur, “Hey. Loved it. It's adorable. It's not working.” Yeah. And so this is where we're struggling. You gotta have that, the data to back it up or the. Results or the, just the confidence to be able to say, I'm dying here. I'm dying here, my team's dying. We need more help and if we get more help, this is what we can accomplish and prove it out.
So when we worked together, I remember very clearly. I totally offended our CEO. Ugh. So many times I did, but [00:30:00] I offended him because while he is one of the most intelligent people I've ever met, an unbelievable entrepreneur and a kind human being like a smart kind guy. He was known for frameworks he'd create 20 different frameworks.
When I came into the business, there were 10 different frameworks and we're trying to understand them and play 'em out and test them out, and they don't align with each other and they're counterintuitive. And I'm like, what are we doing? What's, how many frameworks do we need to have?
So we were at a national sales meeting. I basically just said that we got this framework, we got that framework, we got this framework. And he's sitting literally right in the front row. And I'm like, as I'm up there talking, I'm like, he should have thought about this one a little bit differently.
As always, he was very respectful and professional and I think he appreciated not having Yes. People that worked for him. And he wanted us to challenge him. And so I did, and we I'm like, I need one pick one. Let me do one and do it really well. And we did.
And then we would try to move it [00:31:00] forward and sometimes the frameworks were great and they were successful, and other times he would, better than most people, chalk it up to, okay, that didn't work. What else are we gonna do? Let's try to figure something else out. He was always very good at that.
And so it was a good lesson in. Trying to balance. And learning how to stand up for yourself as a leader. When it's not just about me, it's about a group of people who are dying, trying to figure this out. I we got a clear path here. Let's get 'em down the right path.
Tom: I love that story. It, that getting through something difficult. Does give you the experience of being able to get through difficult things.
Kerry: Yeah.
Tom: Like you talked about your 24-year-old where everything is overwhelming and not a strong sense of perspective about what should I pay attention to and what should not.
That's, I always found that to be the hardest thing when I went into a new organization was like what's important? It feels like everything's important.
Kerry: Yeah.
Tom: I brought together a panic attack in a board meeting where the CEO was like, I was looking at my list of all the crap the CEO O had said we were supposed to do. I'd been there about a week and I was [00:32:00] like, I think I'm on number 48. I didn't know what was important. The problem was he didn't either.
Kerry: Yeah. That's why the idea of self-managing is almost impossible. Because if you don't understand what's important if you aren't given. These are the top five things you need to focus on over the next six months. And even that may be too much, but at least you've got something. If you don't have that you're just going be struggling. You're gonna be in a world of hurt and it's just gonna be a really difficult environment for people to work in. And you as a leader.
What are you gonna report up? What are you gonna show? How are you gonna justify needing more, getting more, wanting more if you can't even get the team to deliver? On whatever's expected, if you don't understand what's expected how will you ever be successful?
It doesn't make sense to me.
Tom: Yeah. That could be tough in private equity environments. 'Cause what's expected is a big exit. Oh yeah. And the kind of number I change can the goals can change depending upon the mood. Cause it's just about the exit. It's not about running the business.
Kerry: Yeah. Private equity is a [00:33:00] really aggressive environment to work in. And the expectations are really strong on growth 20, 25% year over year. Yeah. Which is a monumental level of growth for sure.
Tom: Some people love it.
Kerry: Oh, absolutely. Some people thrive and some people are unbelievably successful in it. Yeah. A hundred percent. Those that are really successful know how to work well with their teams. They know how to optimize their teams and give them the space to do what they do best, but always leading and always guiding.
Tom: Well, let me come back to something from the book. You have early on, you talk about your six brothers and that you learned how men think growing up. What does that mean? If I said I knew how women think. I don't think anybody would want to talk to me anymore.
Kerry: Well It's impossible. Literally impossible. You know, you grow up in an environment where you've got. I grew up in a house with five of my brothers for older and one younger. And I was just one of the guys. Right? So it took me a long time to figure out how women think. Because even though, obviously I am a woman. I was it was just about guys. And so what I learned is that men have a different approach to their emotions and how to control them and how to share them than women do. And in a business environment, that's very helpful because, you know, even though you're frustrated and you're angry and you're upset and maybe at home your go to would be to cry. Yeah. Guys aren't going to cry at work like that just doesn't happen. Although I have cried with many men in the office for various reasons, but you there's just a way in which you control your emotion. And there's also a. Lack of, I would say tenderness, if you will. And I mean that as in guys just present themselves as very strong and and you guys, it's not like you have armor on. It's not that most men I've worked with are very approachable and great to work with and stuff like that, but you you have this armor and that might make you a bit more competitive.
Kerry: It might make you less likely to be vulnerable. Whereas women I have found are not necessarily like that. And now I, I've been told I'm very intimidating. I have been, which I always find very strange. But I have that I have the armor as well. I can very easily have that armor. And when I find myself in a boardroom with all men, when I interviewed for the job that I took after we worked together it was a room full of 6 or 8 men from all over the world. Very different cultures, very different. Everything. And I walked in and I. And I armored up hard for that. And if I didn't have that experience of growing up in a house, whether we're playing, you know, football in the living room or my brothers are arguing and fighting and, you know, they would say debating. I would have said arguing and fighting. If you can't control yourself when you're in that environment, like I learned how to be exposed to kind of crazy aggressive male energy and not to let it affect me and to to figure out how to maneuver my way through that slightly unscathed and or better. Yeah, than when I started the process that that's what I learned growing up in a house of guys.
Tom: That's fascinating. So my I have a 29 year old daughter who lives in Los Angeles, And I'm going to channel Mary Frances for a moment. So she might say that the expectation of men armoring up or of words you used, tenderness is just a social construct that there's nothing innate about whichever chromosome it is. Men have X or Y, I don't remember. That causes people to have this. This is just like it's our it's what we absorb as we're growing up that teaches us to be that way.
Kerry: Absolutely. Yeah I agree with that 100%. Yeah. It's, it's you know what is it environment or.
Tom: Nature or nurture.
Kerry: Nature nurture. Thank you very much. Yeah. Yeah, I think it's very much the, the way in which you're raised is, is how that comes about. But you have a daughter and you have boys as well. Right. So It would be interesting for you to reflect on if you parented your children differently. Most people I know that have a boy and a girl absolutely parent them differently. You know, the boy is there are more restrictions on the girl than there are on the guy. Simply from a safety perspective, for example, let alone on maybe ways in which you behave in certain circumstances.
Tom: So much of it's unconscious. I mean, I'm sure I screwed things up. And I don't I don't mean no, no, no, no, I'm making.
Kerry: It that way. It's just to your point. It's a social construct. It's what we've been taught. It's how we we are. I mean, I, I have two girls, and I absolutely raise them to be very well aware of their environment at all times, period. Men don't have to think about that in the same way. They just don't. And so and you and you and those constructs present themselves in the business world as well. Like it translates over into the business world that there are certain things that men don't even think about when they're in a corporate environment or a business environment that women have to think about. And and I don't mean that in a, in a way that would as talking about like inappropriateness. I'm just talking about you're sitting at the table, how do you have a voice at the table? Just because you're sitting there doesn't mean you have a voice. How do you create your influence so that you do have a voice and the way that women go about it? And I speak obviously just from a female's perspective, the way that you go about it is different than how guys go about it.
Tom: So one of a shared boss we had once said to me that you have to be the most rational person in the room. Did you experience that? Was that to sort of overcome that perception of the irrationality of women just to take a stereo, a A false stereotype. Did you find that? It's like, well, I need to approach this in a less empathetic, more rational way because of my audience.
Kerry: I don't think being rational takes away from empathy. I think what you have to have is a balance between the two. I think it's about always, always being professional. Period. And professional, to me, means you're respectful. You're kind, you're well-spoken, and you're even keeled. I can think of. And I know you can. Too many circumstances where somebody flew off the handle in a meeting, and that is not professional. No.
Tom: And I'm guilty of that.
Kerry: And that is a and that is not rational. You know, but so the idea of I think women are naturally. I shouldn't say this because I know women that struggle with this, but we tend to be, you know, men are from Mars, women are from Venus. I think one of the biggest factors in that is just our ability to tap into our emotions differently, more easily than guys can, and therefore you're able to present yourself in a different environment. I think when men struggle in those environments professionally, where they may be the best part of them doesn't come out, it's because they haven't been taught how to manage those emotions, and women have been taught how to manage those emotions.
Tom: Yeah, I think I think men sort of there's like, I don't have the language for this because if I say men, it seems like I'm talking about old men and I'm not I'm talking about an idea of men. And so I would say that within a certain idea of men there's not an expectation that you either control or manage your emotions. It's called. He's. He cares. Yeah. Why is he yelling at me? Because he cares so much. And like you say, he's not yelling at you. He's debating, you know. So there's it's right. Whereas, so it feels like there's sort of more built in justifications for abuse for people who you know, are men. And so it's like as a woman, I haven't been a woman, but as a woman coming into work, it feels like, well, the expectation is you're going to make allowances. This is a, you know, a guy's thing and you're coming into the guy's club, and that means you need to make allowances. Am I is that inaccurate? No.
Kerry: Okay. No it's not inaccurate. And I wish I could say the good old boys club, as we call it was unique to a certain industry or certain environment, but it's not. And you know, and I should say this is something that my daughters taught me that I use this term a lot. It's not every guy that you know is a bad guy or is a jerk or is or whatever, but every woman has experienced something related to that. So. So I would say there are many men that I have worked with who are fantastic, wonderful human beings that I learned a lot from, good or bad or whatever. And then there are those guys that you're just like, good Lord have mercy. I don't know what rock you crawled out from under, right? But I imagine men would feel the same way. And there are other men that they've dealt with that way, or even women, of course, that I've met some horrible women in my day. Right. But I think that the challenge is when you when you're talking about that that rationality, or the irrationality of a woman in the workplace versus a guy or like that, you know, wrong stereotype that is out there. Well, it is a stereotype. That's what it is. It it comes down to in my experience, a person's ability to just look at and see another person and recognize they have a different perspective and that doesn't make it wrong. As I said, I have sat in many a conference room, many in office, and had the man, my boss, sitting across the table from me, get emotional and start crying. And but we're not talking about work. Yeah, we're talking about family. We're talking about life experience or things that have happened. But the fact that they're able to get emotional with me, you know, it's like, oh, wow, okay. They're a human being. I totally get it. Never in a million years has a man sat across a table for me and cried because they didn't hit the numbers, or they messed up the presentation or something like that. Or because they feel pressure. They feel pressure to perform, to do the job. Whereas I have had many women sit across from me and just that's the release. That's the emotional release that happens, and that's what they have to do to get it out. Men have a different ability to control that, I would say, or to process it differently, you know.
Tom: Or stop it than, you know, analyze it. Yeah. It depends. I, you know, I people do get driven to tears and work environments. And to me, it's just like, it's insane. We treat each other this way. And anyway why is that. Why is that necessary? But I want to pursue the idea of what your daughter said. Of it's not every guy but every woman has experienced this. And to put that in the context of my daughter says which is that if you've been in a position of privilege, equality feels like oppression. And so what does that look like? Like let's say there is a Cicero Inc. One solution that people that I've heard that people do is like, I'm gonna have an all female business. It's just like there are plenty of all guy businesses in the world. Yeah. I'm gonna have an all female business if you when you start. If you start Cicero Inc. Yeah. How will you try to create that culture where it doesn't matter if I cry at the presentation?
Kerry: Well, it doesn't matter if I cry at the presentation now. You know what I mean. I create an environment on my teams where I allow people to express themselves because I believe that whatever emotion you have, you have a right to that emotion. Now, I can't have it happen every single day. All the time. Right. And that would be then that means something is happening with you that you need to work on, that you need help somewhere else. And that's totally fine to do that. I mean, I can say that my experience has been with my teams, that I have led and I have led throughout my career, hundreds of people. The feedback I get from my employees, male and female, straight and gay. You know, pick a race and I've led them. It doesn't matter. Is that they are grateful for my leadership. They're grateful for the ability to express themselves, to have a safe space, to be able to share their frustrations, to to share their happiness, to know that what they do matters. That's the culture that I create on my teams. And in the book, that's the foundation of what I wrote, is what kind of got me to that experience. You know, you I have to, and I do the same thing with my children. I allow my team members, my children, to call me out. It's the hardest thing in the world. It's the biggest mistake I've ever made in my life, I swear to God. No. So when I was at home, if I'm reprimanding my children, if I'm disciplining my children when they were younger, and if I were to raise my voice, the response from my children inevitably would be, why do you get to yell at me? But I don't get to yell at you.
Tom: That's a good question.
Kerry: And I would then have to be like, God bless America. I taught them that to which I would then stop and I would breathe. I would count to ten and I would say, you're right and I'm sorry. You deserve more respect than that. However, I've asked you ten times to clean your bedroom, you know, or whatever it might be, and it's the same thing at work. When we do annual reviews. God love them and hate them all at the same time, right? There's so much work, but it is a great opportunity to have a very real conversation. And in every employee review, I just finished them for the team I support right now. The question I always say once we get done with everything is, do you have any feedback for me? What can I do better for you? What do you need more of or less of from me? And you know, oftentimes you're doing great. It's wonderful. Or no, I can't think of anything. And if you think of anything, let's just bring it up in our next one on one or whatever. But I have had people go, all right, let's go. Out comes the scroll. And they've got a bunch of ideas. And they tell me, this is how you make me feel, and I don't like this, and I need more of that. And I have to put my ego aside and listen to what they say and start to recognize, oh, wait, I'm playing a role in this relationship. And I have a I have very real power over this person, and you cannot take that lightly as a leader. I think that's what a lot of leaders, that's where they fall down, is when they don't recognize the power that they have and the influence that they have.
Kerry: And with those two things, the impact that they make on their teammates very easily, very quickly, I can destroy somebody's life or I can make them have the greatest life they've ever had. And I don't mean that to sound arrogant, but the truth of the matter is, I can if I were to ever walk into one of my employees offices and lose my shit on them oh, they will remember that day for the rest of their lives. Period. And so you have to think about that when you're having these conversations and when you're leading the idea of leading with empathy, the idea of creating happy, engaged, high performing teams, there's so many things within that statement. Happy. How many times are you really happy in your life? You may have moments of happiness throughout the day, but are you really happy? Do you really want to come to work every single day? No, none of us do. But if in general, you want to be there because of the people you work with, and you enjoy the work that you're doing, that's great. Are you engaged? Do you care? Are you motivated? Are you inspired? And then high performing? You know, we got to build the business. We got to we have to achieve. We have to hit the goals. We may not hit them all the time, but we have to know where we're going and understand that we have a measurement that we're being held accountable to. So those three words are very specific to what I try to work on, because if I can get them to be happy and they're enjoying themselves, they will be much more engaged and they will perform well. Period.
Tom: It's been a lot of fun.
Kerry: Thanks, Tom.
Tom: No, I really appreciate you coming over.
Kerry: Yeah, I. Appreciate it.
Tom: And so before totally closing out, tell me what you wear where you want to be. So you've written a book. You told me before that one of the reasons why you wrote this book is because you like speaking publicly. I do. You like talking about leadership? I do. So what do you hope happens comes from having written this book.
Kerry: You know, I want ultimately, like the quote unquote retirement plan is that I'm a part of a speaker's bureau and I'm able to speak at conferences and corporate events and things of that nature about leadership, about how to build really high performing, happy teams, you know? That would be the goal. And, you know, a couple of those a month.
Tom: That'd be fun.
Kerry: At a nice low rate of No, no, that would be great because I feel like. I just feel like I could help some organizations, you know, maybe, maybe create cultures and environments that are are maybe a little bit better than what they are today. But I don't profess to be a culture guru or anything like that. I just know how to make people feel really good about the work that they do, and that the team that they're on. And and it it changes. It changes everything for them. And that makes me happy.
Tom: It's great to see you, Kerry.
Kerry: Thanks, Tom.
Tom: The Fortune's Path podcast is a production of Fortune's Path. We hope service and technology businesses address the root causes that prevent rapid growth. Find your genius with fortune's path. Special thanks to Kerry Cicero for being our guest. Using an editing of the Fortune's Path podcast or by my son, Ted Noser. Look for the Fortunes Path book from Vintage Books on Fortune's Path. I'm Tom Moser. Thanks for listening, and I hope we meet along Fortune's Path.