Finding your Identity as a Leader (The Naked Truth with Robin Levitt)

Below is a lightly edited transcript of “The Naked Truth” show I was recently a guest on. For more episodes and information about Robin Levitt and “The Naked Truth” check out her YouTube channel here.

For and From Women in the Workforce is a candid, empowering YouTube channel dedicated to exploring the real experiences of women navigating the professional world. Hosted by Robin Levitt, founder of 4DExecutive Search, this show brings you raw, unfiltered stories from women who have made it to the top in corporate America. Whether you're just starting your career or navigating your way through your career path, we’re here to help you crack the code on networking, mentorship, leadership, and landing your dream job.

Emphasis added.

Robin: Hi Andii, thank you so much for joining The Naked Truth. I'm so happy you're here and super, super appreciative you are willing to take the time. So thank you. 

Andii: Really excited to be here. Thank you. 

Robin: So I just want to share with the people who haven't had a chance to get to know you like I have. I have a little bit about your background, and then we'll just jump right into it and start talking about all the things that are important to our communities out here. 

Andii is a talent leader who has spent over a decade building growth stage B2B tech startups across Saas and professional services, either in public safety, which was drones as first responders. So cool. Need to hear more about that. She’s also worked across health tech and cloud consulting and construction management, and has continued to build her career. And I'm so excited to hear more about it and the challenges you found along the way, and advice and all this fun stuff. So let's get to it. Let's do it. Let's just start. I'd love to understand, like, what was the beginning of your journey and becoming a leader? Like, where do you see as that starting point for you?

Andii: That's such a great place to start. So this is gonna sound a little bit silly, but I really feel like I was born into it.

Robin: And this is The Naked Truth, nothing is silly, we’re just being real. 

Andii: Exactly! So I'm the eldest daughter, so I'm the oldest of four kids, and as many eldest daughters out there in the world, I was expected from a relatively young age to be that third parent and extension of my mother. Whether it was helping with the household, raising the other kids, just generally, you need to be that helpful and responsible person. And in so many ways, that's kind of where I track back to like, Okay, I feel like I was born into being a leader, because when I was really young, it was something that was just expected. 

And when you're growing up, you don't really separate yourself like you're still kind of developing your sense of self, right? And so you don't think like I'm a child, but today I'm going to step in and be the babysitter, or I'm going to put on my hat and I'm going to be the driver or the chef or the coach or the person who's kind of just running around, taking care of things, right? You don't really think of stepping into those roles. It just kind of all blurs together as this is both my responsibility, but also my identity. And so that's kind of both the nature and the nurture, I think a little bit of those early years.

Robin: I'm sure there were moments the oldest daughter that you were like, Why do I have to have so much responsibility? And then I'm sure there were moments in your life now, as a working woman, where you're like, hmm that really prepared me for way more than I thought it was.

Andii: Absolutely, and so in the same way that you kind of feel like I or I felt like, in many ways, like I was born into this leadership role. There was this one moment a little bit later, when I was in high school, I was about to go into my sophomore year of high school, and for context, I'd been a musician like I was a trained musician from like age six, so I was very engaged…

Robin: Were you a singer or did you play an instrument?

Andii: I played flute and some piccolo and a little bit of piano. 

Robin: So cool, yeah. 

Andii: And so I was involved in kind of every kind of music program there was available to me growing up. And so one of them was the marching band in high school. And this was again, the summer before my sophomore year was about to start, it's 100 degrees out, and myself and over 200 of my peers were standing at attention, silently, all sweating. 

And within the larger kind of band, there's sections, you know, the woodwinds, which were like the flute section, the clarinet, saxophone, things like this, right? And the section leader, or the group that I was in had graduated previously. 

And I don't remember what exactly had happened, but we're all standing at attention, and my conductor is very angrily demanding on a megaphone who is leading this (my) section. And I don't know what it was, but it was just this very visceral, like, by the second time he asked the question, my hand just shot up. And there were so many kids that were older than me in this group that, you know, I didn't have time to think about there was no vote, there was no discussion, there was no tryouts, like, Hey, do you do you have what it takes to be this leader? It was just this kind of, in that moment, I knew that it's me, it's always going to be me, and I want to be that person, and I am that person. 

And so what's really awesome is, yes, you do kind of feel like, as the oldest kid, like, I have to be a leader. I have this responsibility. I'm the person who's dependent upon. But there are those really great moments where I could have just stayed silent. I could have stepped back and then, like someone else will raise their hand, but I just, in that moment, knew that it was going to be me.

Robin: I'm curious, like, when you walked into these corporations, that you've been the Head of Talent, Head of Talent Acquisition and leading teams like, how is that benefited you? You know, because I think as we're talking to other women out there, and lots of women, hopefully are going to be listening to this, both our future female leaders as well as peers of like, you know, just getting different ideas of how other people step into these leadership roles, and oftentimes a leadership role amongst a team of many men, you know, and and how those things show up in the workplace, and I'm wondering, like, what have you seen the pros and cons of that in a working setting, in a leadership capacity, your ability to be like I got that handled. You know, what has worked and what hasn't worked for you, and what have you had to adjust along the way, and being that person on a team in a corporate environment?

Andii: I think you know, when you first step into a not even leadership role, but management role, your first one, some people step into it. Some people are clamoring to get it. Other people are forced into it, a little bit within their org, right? You kind of step into it. You go, Okay, I know what it feels like to have a “bad manager” from my experiences, and I kind of have some idea of what a “good manager” might be, or what that might feel like, and that's kind of all you have. There is no handbook. No one says, Great, you have direct reports. Here's how to be a manager. Follow step 1 through 3, right? 

And the very first opportunity that I had to do this, the environment I was in was incredibly high pressure, long hours. We were all shoved together in a small, little office. And my kind of default, I don't know if it was a survival mode or what it was, but I was like, You know what? I'm just going to be another member of the team. Everyone's going to be my friend, my peers. I don't have it in me right now to try and figure out what manager means, versus just being another high performing individual who's setting the pace. 

And that works out great, until you come up against a moment where you can't be everybody's friend anymore. You have to make a tough decision, and you have to show up as a manager. And this happened where within those kind of early days of this team, and this is the first and last time this has never happened to me, but my boss came to me and she said, Hey, everything you've told me about this employee, that you're kind of struggling with, everything you just shared with me about this investigation that you did. It's time. We need to let this person go. 

And then I had to sit down the very next day and fire someone who I have largely just been treating as a friend and a peer for the last six months. And this is where I have this first moment, this butting up against this idea of like, I can't just show up as me, this really strong, high performing person, this over achiever. I actually have to consciously figure out what role am I showing up in, and I have to do that intentionally. And I have to figure out in every interaction who I need to be and who I need to show up as. 

And I think when we first get that exposure to management or people leadership, you don't really understand that there's an ocean in between people management and leadership, right? 

Leadership, you are building a vision. You are getting people excited about that vision. You understand the micro and the macro of everything, not only internal to your team, but your business, the industry you're in, and the kind of keep layering out from there. And you're creating an environment and setting high expectations for your team, but this environment you're creating ensures that everyone knows how to meet those expectations. And then you're doing these very targeted interventions, whether it's advocacy, air cover, conflict resolution, whatever it might be, but so much of the time that's just bundled up into this word of like, well, leaders are strategic. 

And I've heard so many women who are like, Well, I'm stuck in this people management space, and I want to be a leader, and I'm just told I need to be strategic. Well, all of that, what I just said, like, that is being strategic, right? 

But people management is this day to day of who's going to do what work are you following the process? I did my one on one’s. I did my stand up meeting. I divided up the work. I'm auditing things. I'm escalating to somebody else when I have a problem so they can go fix it for my team. And when you're a first time people manager, the one thing I've seen go really wrong is instead of this kind of expansive vision building you do Kingdom building, and you build a castle, and I’m the king or queen of this castle, and everyone's just going to do what I want them to do, because now finally, I'm in charge, right? 

But what you don't realize is you're butting up against other people, you're creating conflict. You're not showing up as a leader. You're just kind of showing up as this people manager. And so I think that's something really interesting. When you first step into that role, some people immediately are like, Great, now I'm going to build my castle and dig my moat, and this will be it, and I'm in charge now. 

And other it's the harder thing to say, actually, I don’t want to build a kingdom. I don’t want to build a castle. I want to build a vision. And I need to get all of these folks with different backgrounds and experiences, and I need to all treat them as seasoned professionals, regardless of where they came in at and get them excited about this vision that I have. And I think that was also something that I had to kind of learn the hard way over time of what that looks like.

Robin: Yeah, it's interesting because, you know, you noted, like, you didn't have the playbook, you did have a manager. And so, like, you were in, you know, when we're in these growth companies, it's different than if you're in a Fortune 100 company or a much more mature company that has an incredible leadership development, where it's like, okay, you're going to start here as a manager, then you're gonna have this program, you know, these incredibly robust learning programs that teach you, but a lot of companies don't have that, especially in the growth mode. So I'm curious, as somebody who's gone through that and didn't have what that specific playbook handed to you, what was the biggest lesson you learned that you can pass on, you know, maybe future female leaders, first time managers that are going to be going through that, that you really learned along the way.

Andii: Yeah, I would say that the biggest lesson that I really want to pass on. I think this is something that you know, if I was to talk to my younger self, or really anybody and any woman, I think I would sit her down and I would say like, you've got to unwind some of these things that have become very intertwined. 

And these things are: your self worth, your value, your identity. Your work is not the only thing that is valuable about you. And I think that we are constantly told whether it's within our family structure, growing up, our culture, our society, our workplace. We are constantly told what is valuable when you're valuable, what you look like when you're valuable, how long you have to do these things. 

I loved the Barbie movie, and America Ferrera does this amazing monologue towards the end, and it starts with, “It is literally impossible to be a woman, right? You're beautiful, you're smart, and it kills me that you don't think you're good enough. And we always have to be extraordinary, but somehow we're always doing it wrong.” and there is no right way to do it. 

But the first thing that I would say to somebody who is, who is out there as a leader or a woman in the working world is you have to figure out what your own value system is and define that for yourself. 

Because, and I want to share something really specifically. And I've, I have said these words and a variation of this, and I've had a variation of these words said to me, it's something along the line of like: if there's any other work that you can give me, any other side projects I can take on (so in recruiting) I can take on more searches, and then they follow up with I don't have kids, I don't have any other commitments right now, I can work longer hours, and I don't mind it load me up, give me more things to do, and it breaks my heart every time.

Because when I said those words, and what I hear when other people say that to me is I'm not as valuable as these people who have children to raise, or spouse at home, or commitments outside of work, my value could be in this work that I produce for you, my productivity, what I am going to generate for you. 

And it can't be one thing over the other, because if your value and your self worth ends up solely becoming what your job or your manager sees in you, what happens when you lose that job? So many of us have been through this, right? What happens when you don't get that raise or that promotion, that you feel like I'm sacrificing everything. I'm not even trying to chase after these other life things. 

And I have spent time in organizations where they were getting a ton of value out of me, and I personally was not building any value outside of that work that I was doing for them, and I didn't take my time to invest in friendships and relationships and all of the things that were going to create long term value for myself and ultimately pay dividends, because it makes you a better leader, it makes you better co worker, makes you better manager, whatever it is a better teammate, right? 

To have a more broad perspective and to diversify this, because at the end of the day, like for your job, your job is not going to love you back, right? You can love your job. Your job isn't gonna love you back. 

But the thing is, for my eldest daughters out there, for my overachievers, we grew up chasing these gold stars, for my type a people, that recognition that we get in our careers is a way that we feel love, right, and kind of have to rewire ourselves, and that's a huge challenge, and this is a lifetime of work to get through this. And I don't have the right answer or shortcut on how to get there, but you're not defined by your outputs. I think that's like the biggest thing, and you got to develop what that identity and sense of self worth is. And it can't all just be every egg in the basket of your career or your job title.

Robin: It's so important. And I think you're so right. And there's so much external especially as like female leaders, there's so much, you know, judgment coming in. Either you're the leader without kids and without a family and so everything dumped on you, or you are having other challenges as a mom, or having other challenges as a daughter of a parent who is ailing. And, you know, there's, there's always a scenario. It's like, I talk about I have the most loving husband and dad and son, and I love all the men in my life. This is not to put them down. It's just different, like I would be the first to put down a call, or to say I have to reschedule because I have this commitment. And I think there are a lot of men at least that I know, not everybody, but there are many who are like, I can't do that. I have a call, you know, and it's very different. 

And I think because we, you know, we have had to strive. And I think things are getting better, you know, as women in the workplace, but you know, there are more of us now, many more of us and many more women going to college, and I think it's constantly shifting, but to the point of this conversation is in teaching other women and sharing truths among our peers, is that having that sense of self that only you can define. 

You know, nobody else can define that for you. And I think, like you said, we it's a lot of people out there have been defined by the work, by the job title they've been given, by the salary they've been given by the company they work for. And they forget to identify as self and identify as what is my internal value that I'm bringing to the workplace versus the workplace giving me the internal value? And I it's so niche, and it's so something that I it's so hard to get right off the bat, because you just want to put everything out there and prove yourself. Because you're new out of college, or you're just becoming a first time manager or first time director or first time VP, whatever it is, it's a long journey, you know, but it's, 

I think, you hit on something so important, which is that no matter where you are on that journey, continuing to circle back to what is that self comfort, those self boundaries, those self evaluations that you have to be aware of, and it's so easy to constantly get them externally. 

I mean, I know, for me, I mean, you know, working now for close to 30 years, and it's like it is still a project, right? It's a constant learning experience of, Oh right. I bring value. Oh right. I do know something, because the truth, and especially with social media, there's always gonna be somebody doing it better, somebody's gonna post about it, and it's gonna look like they're doing it better. And there's so much comparison out there that we often feel bad about ourselves. And so finding that, I'm just so glad you brought this up, that finding that internal self identity. 

So if you can show up as your best self the way you want to, there's always going to be a place who's going to be better than you and worse than you, and but knowing who you are, what your value is, exactly where you are, is just a game changer. It's a game changer. 

I'm so glad brought that up, and I'm curious, you know where you are now and being in companies that you continue to learn this and continue to grow as a leader, you know where you are today versus maybe where you were as a new leader, and the hurdles that you're facing at this point, you know what's the next hurdle that you're facing as a female leader in organizations these days?

Andii: I would think the next hurdle is figuring out what that next challenge is. What is that thing that's going to excite me? What is the thing that's going to let me kind of show off the skill sets that I've developed? 

I think my earliest hurdle though, and the one that I think might resonate so much with so many women and one thing I actually learned a great mentor, who is still my mentor today, was to open up and be vulnerable. And so I would say, like the biggest hurdle I've had to overcome is anger. And it's because of some of these friction points, these contradictions that we just talked about. 

But I think early in my career, I was so angry because I had this, this raw talent and these skills in this huge, super high drive to achieve right? But in this one, this one office I worked in my coworkers, the biggest thing they wanted me to do was to keep the printer running, and not because maintaining the printer was my job. It was because I was the youngest woman in the office, and I happened to sit next to the printer. I was the Chief of Staff to our Head of Engineering for an engineering company that worked in defense. But because of all of these things, I kind of got pigeonholed in its place. 

And as women, it does not matter how senior we get in our careers, how accomplished we are, the things that we go through. Every woman, whether it's in private spaces, public spaces, the workplace, we are all just by existing, running these friction points right where, and especially early, I struggled with this where it's like, Wait, my idea is good, am I just not saying it in the right way, like no one seems to really be hearing me. And so I kind of felt like, and I still sometimes feel like this, I'll be totally honest, you're playing a game and you don't know what the rules are, right? And if someone would just tell me what the rules are to this game, I could be really good at it, right? 

So instead I would turn it I would say, okay, my reaction to any time where I'm in this situation where I'm like, Okay, I'm a little bit in over my head. I'm not really quite sure what I can do to be successful here. I'm going to double down. I'm going to work even harder. My work is going to be unimpeachable. No one can say I'm not doing quality work, or that I'm not working hard enough, and I just don't know whatever game is afoot, right? 

Whether you feel like it's a political game or you're just not being set up for success, because we're constantly having to juggle this right, where you're fighting against getting pigeonholed. Thank goodness that we have AI note takers, I'll be honest, because I hope that this eliminates for a whole future workforce generation of the youngest woman in the room being expected to take notes regardless what her title is. 

But you're either pigeonholed into admin tasks or things like that, or even order us lunch, right? Or you're struggling to be assertive and get your ideas heard, that you don't want to become off as difficult or too direct, which is something I still sometimes get. You're trying to be friendly, but you're not trying to invite sexual harassment. And when that happens, you kind of have to grit your teeth and just like, avoid or get through it right, which is a common experience so many women have. You're also trying to find allies, but sometimes those allies turn out to be those Kingdom builders where they're like, Well, this is my castle. You're like, well, that's not a great example, of I want to be. 

And then also, to your point about the role of a mother, you can sometimes end up getting - and to be super clear I'm not a mother, and I don't have children. But there was this one team that I built, and they had decided that this was the role they wanted to see me as. I couldn't just be seen as their leader. I had to be seen as their mom. They wanted me to be the person who took care of them, who would nurture them, go to bat for them, and I think in a broader context as a leader, sure you can flex into each one of these things. They even got me a Mother's Day gift once, and it really threw me for a loop, because the opposite side of being a mom is that if they were unhappy or they didn't get exactly what they wanted, I was also the target and somehow source of all their unhappiness. 

So I felt like I was in this lose, lose situation, and it made me frustrated, because I didn't want to be their mom. I didn't want to be put into that role, just like I didn't want to be the person who had to go fix the printer jam or replace the ink. 

And so if you have this layer of anger and frustration over the situations that you're finding yourself in, and then on top of that, you're pushing yourself like, I can work my way out of this 80 hours a week, 100 hours a week. I'll get the recognition. I'll get the respect, whatever it is that you're chasing. But if you layer these two things together, what ends up happening is you can't show up as a great leader or a good people manager or even a good teammate. 

You show up as a very driven person, but also kind of angry and a little bit unapproachable, and that was me at one point in my career, and I had to figure out how to unwind.

Robin: Yeah, how did you shift it? 

Andii: Yeah, so I really consciously had to figure out, how did I want to show up day to day? What is my core persona that is as true to myself as possible, right? And I want to be comfortably living in that. I want to choose when I lean into these archetypes, it's my choice. It's not someone else putting me into that place. I flex into this, and I'm using these things to my advantage. 

To go back to the mother role. There are times in which the best possible persona I can show up as is incredibly loving and kind and supportive, and being able to sit here and genuinely look someone on my team in the eye and tell them honestly, I am so proud of you, right? And I have created this soft, warm space for you, but it is not unconditional, right? That means I'm not your mother. This is not unconditional, because the next time I talk to you, because we had this wonderful, warm moment together, right? The next time I talk to you, I know that I've built up some trust and comfortability and confidence in our relationship where I can push that person really hard. I know you can do better. I want to see this from you. I know that you have this in you.

And so it's taking control back over the situation. Right now, I've, I've had a 15 year career, so I've had half the experience that you have. In my current role, I'm Head of People and Talent and Facilities and and and right early stage Series A startup, you get to be a little bit of everything. Did I not two months ago, sit and order a lunch and pick up after people? Absolutely. Because that's what was needed, and that was the moment I'm flexing into this, and I can be that person that makes everyone feel really well taken care of today, because that is the most valuable thing. 

It is a tool in my toolbox that I pull out, and it's my control and I decide, and it's for the benefit of the company, the mission, and a lot of the time, most of the time, as a leader, benefit for that person that I'm helping.

Robin: It's not being forced upon you, like you said, it's like a choice you are making for the greater benefit of yourself, your team, your organization, instead of somebody telling you where it didn't need to be. And that's as a nuanced shift, but it's such a big shift, I think, as you continue to mature in your career, is just that, right? Is knowing when to that it is valuable, right? 

It's not just like, Oh, you're making me go get lunch or ever know, like getting lunch could be like, an incredibly valuable thing to just get it done so we can move on and get to everything else, you know. So I think that's a really cool shift you've talked about is really having an understanding it’s tools and making choices of how you will benefit both yourself, your career, the organization, instead of it being forced upon you. 

I love that. That's really, it's a good message, it's an important message. 

And I think it's really difficult as you grow as a manager. Those are big things you learn along the way. 

And I think in the next 15 years, it's going to iterate again, you know? It's going to become something different. It's going to become a bigger, stronger voice. But that voice along the way is really important, right? And it's, it's constant learning. So I love that you know, you can look back now and say, That's what I was, and here's what those choices mean differently. Now, I think it's incredibly valuable advice for our future leaders. 

So I really love to keep these to the 30 minutes, because I know we're all so busy, and you've shared so much amazing, amazing advice today. And you know, I know we've talked a little bit about that you're always open to talking to people and sharing and the valuable insights you have along the way. So thank you for showing up as that today. And you know, as a leader in the talent space in these high growth companies, and it's going to be really cool to see where you go in the next 15 years so thank you for sharing your story as it is today.

Andii: Yeah, thank you so much Robin, I really enjoyed it.