Executiveland is the podcast for senior leaders, aspiring executives, and anyone who wants to understand what it really takes to lead and succeed at the top.
Hosted by executive coach and trusted advisor Elizabeth Freedman — founder of E•Suite Leader and longtime advisor to Fortune 100 companies — this show takes you behind the scenes of 20+ years working with C-Suite executives and their teams.
Each month, you’ll get real-world insights from the coaching room: what works, what backfires, and the subtle traps even experienced leaders fall into. You’ll hear directly from executives about the do’s, don’ts, and day-to-day realities of leading at the highest level — the kind of stuff no one puts in a leadership book.
Whether you're an executive now or working closely with one, you’ll walk away with practical, actionable strategies to earn trust, build credibility, and make a bigger impact —Because no one hands you a map to Executiveland — but this is the next best thing.
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In this episode of Executiveland, Elizabeth Freedman makes the case for embracing your inner weird. Drawing inspiration from Weird Al Yankovic, Elizabeth explains why your unique leadership style isn't a flaw to edit out, but your real competitive advantage.
Key takeaways:
How to spot the distinct qualities that make you effective, even when they don't look like the traditional executive playbook
Why feedback like "be tougher" often confuses someone else's style with the actual outcome you need to deliver
A practical way to separate useful observations from limiting assumptions about what a senior leader should be
Why real executive confidence comes from knowing what makes you great and having the courage to lead your way
Listen in and ask yourself: what's your weird, and are you using enough of it?
Hi, and welcome to Executive Land. I'm Elizabeth Friedman, and this is where top leaders go off script to share straight talk and the unwritten playbook about life in the C-suite. For more ideas, visit East SuiteLeader.com. Now let's dive into today's episode. How many of you are fans like I am of Weird Al? Can we just get a round of applause for Weird Al Yankovic? If you don't know who I'm talking about, Weird Al is the Grammy-winning musical genius, complete dork comedian who has spent over 40 years turning all kinds of huge pop hits into these really brilliant parodies. I know a lot of you know exactly who I'm talking about. He's created such brilliant albums as Poodle Hat. How many of you listen to Poodle Hat? What about Poke Party? My very personal favorite Weird Al album is Dare to Be Stupid. I really admire Weird Al, and lately I've been thinking we need more weirdos. We definitely need more weirdos inside organizations, and above all, in executive land. Now, listen, I we we got to talk about the word weirdo for a minute because I do not mean being unaware, being inappropriate, being annoying. No, no, no. I'm really talking about the idea that weirdo is about a willingness to lead in a way that works for the organization, but also works best for you. I would say, even if it isn't, let's say the most expected way. So I am making the case today for everybody to be a little bit weirder. So let's talk about that. Number one, I want you to know what makes you weird. You gotta know what your weird is. And again, I want to say it's not being quirky or funny necessarily. It could be something that's pretty invisible to other people. It could simply be the idea that your style is much more soft, maybe a little more compassionate, nice, than you uh have come to believe, let's say, a hard-driving senior leader is supposed to be. Maybe you are a leader who I would describe as on the quieter side, and you're in an organization that really rewards extroversion and I don't know, commanding the room and that kind of behavior. It's the way that over and over you know in your gut that that's just not the way you do it. It can be truly small. So, for example, maybe everybody else goes to the team dinner, but you know, after 12 hours of meeting with the team, you do not need one more person. You need room service, you want to be by yourself, you need eight hours of sleep. So it's knowing like what makes you truly at your best. And again, I want to say it does not have to be profound. For example, if I think about Weird Al, it's his weird isn't just that, you know, he's funny. A lot of people are funny. It's this combination. Talented musician, smart, of course, but also silly, a dork, totally okay being uncool, plays the accordion. I am so glad when someone earlier in his career may have said to him, like, have you, if you're a serious musician, like maybe drop the accordion, do something else. I mean, thank God he didn't listen to that. But I was working with a CEO who really loves to ask a lot of questions, maybe not uncommon, but he was getting all this feedback. You know, you need to be more decisive. That is not his style. He does not walk in the room and start telling people answers and making decisions. He's deeply curious. He asks a lot of questions. His team at times for sure would wish, could you just please tell us what you're really thinking here? And okay, maybe there are moments when he does need to do that, but his ability to be good, smart, really brilliant in his role, it comes down to those questions for him. It's just how he learns, how he's able to see around corners. And so I think my point here is you don't want to crush your weird. Okay. It's really learning how to use it. And ask yourself things like when you know you are really able to do something well, what's going on there that's distinctively you? Sometimes another hint is, are there parts of you that you think, uh, I really should do it this way? I should do it more like them. I, you know, parts of you you may be tempted to tone down a bit. That's another good sign, like, no, that's the part that makes you weird. Don't lose that. And of course, the more obvious but really helpful diagnostic is just when people say, what you do really well. Ugh, that's so you. Those are the moments to pay attention to. And it could be anyone, not necessarily just the people you work with. I find other people can see your weird much more clearly than you. To you, it may just feel normal or not something you would want to do at work, but that really could be just such a powerful differentiator for you. And this brings me to the second idea. You have to know you're weird, and then you really have to protect it. You know, one of the things you hear all the time about leaders at the executive level is they stop getting feedback. I have to tell you, I have not found that to be the case. And look, in part, I collect a lot of feedback on the leaders and teams that I work with, but they are getting signals and messages all the time. But feedback can be an interesting thing when it comes to being weird. Let me give you a quick example. So years ago, I remember I was getting my MBA and I interviewed for a job with a fancy consulting firm. And it was a process, interview after interview, multiple rounds, and I finally got to the last stage. I was with a group of other candidates, and we had to each present together in a room in front of this interview panel. And I remember getting feedback, and the panel sat me down, and this is what they said. We don't get you, you did really well, but we cannot figure out whether you're actually smart or maybe you're just a good actress. I mean, like, what do you say to that? I I was truly stunned. I think I just was silent, and to be honest, I was just so humiliated by the comment. Needless to say, I did not get the job. And I really thought about that comment for a long time. And this is the thing that can happen with feedback. Someone on an interview panel can make a comment for five minutes. You and I can think about this for the next five years. And that is what I did. I didn't consciously realize it at the time, but I started really adjusting my style. And I remember thinking, like, maybe I'm not substantive enough, maybe I'm too performative, maybe I need to prove more that I'm smart. Um, you know, looking back, I just spent all this time trying to prove to some interview panel that has long forgotten about me from a million years ago that no, I really am smart. And, you know, what started to happen over time was I thought, well, okay, that feedback was useful. I'm glad I heard that. I even started to think, yeah, they're not wrong. That actually is how I can be. Sometimes I'm not that smart and I'm sure I'm just acting. But you know, now when I hear that comment, the only thing I think is, and that's it. I mean, is there actually a problem here? Maybe I was both. Maybe I was a little bit smart or not, and also I was an actor, or I couldn't gauge the room. Maybe I could take an idea and bring it to life. Maybe they just had no idea how the hell to categorize me. But you know, now I know, no, no, no, that's part of like how I'm weird. I just truly wish I had kind of embraced that and understood that sooner, honestly. I recently heard a friend of mine, a coach, tell a story, and it also reminded me, same thing. When she was five, she was telling me she loved to draw. And her mother, beloved, loving mother, made some comment about the picture she had been working on. Like nothing particularly cruel, but something to the effect of, you know, I think you could do a better job than that. Her mother, I'm sure forgot about the comment five minutes later, but the five-year-old coach heard, you're not a good artist, and essentially decided, I'm not gonna draw anymore. And I see grown-up versions of this all the time. All the time. I work with leaders, they get feedback, and the feedback might say, you ask a lot of questions, and the leader says, Okay, well, I need to stop asking so many questions. Um, I'll read feedback that says, you know, you're really, really, you need to kind of manage your style to be more CFO-like. And what's interesting is we read these comments, and for some of us, if we're not careful, they can become a rule. They really cancel, you know, we have to watch for that. Of course, feedback is important, of course, it can help us grow, but if you're not careful, it can crush the weird. Remember working with a leader who was being considered to be the next CFO. I work a lot with finance leaders. And one piece of feedback this leader got, I've heard more than once about leaders. And it amounted to this: this next CFO, if he's gonna be successful as a CFO, he needs to learn how to be tougher. Okay. So we could have like immediately launched into Operation Tough Guy and been more hard-edged, you know, let's learn how to be more forceful. But you know, I remember saying, Do you actually want to be a tougher leader? Not can you, but do you want to be that kind of leader? And he just said, no, that's not my style. Great. To me, now we have really something useful here because underneath be tougher, there could have been a very legitimate need. You know, be more accountable, stand your ground. Those are outcomes, but be tougher is someone's prescription for how to get there, not the same thing. So this is so important when we give feedback at those senior levels. Because feedback, as we know, there's often a really useful observation in there, and also someone else's idea of what good looks like, what you should do about it, how to demonstrate the following. I just wouldn't accept both of those ideas as true. So, for example, I often collect feedback, as I said, and maybe I'll read something like this is a leader that's far quieter than other executives at this level. Okay. And is quiet hurting this leader's influence? Or does this leader just influence differently? Uh, I remember getting feedback recently. You know, this she asks a lot of questions. Okay, but what's the problem? Are the questions getting in the way? How are these questions useful to her? Or he isn't tough enough. Okay, what do we actually need him to do? So that is the question over and over. What is the real outcome people are looking for? What is going to be my way of achieving that outcome? So, again, I'm not saying we dismiss feedback. It doesn't mean we say, you know, that's just who I am and deal with it. But really being able to protect your weird means we can't let feedback turn into a rule or crush what actually makes us valuable and differentiated and so unique. Which brings me to the third idea, which is use your weird. Weird is not just about a personality or a leadership style, it's courage. Because we all know it is so easy to have conviction and belief when other smart people agree with you. But now try sitting in a room full of other smart, experienced leaders, and then you say, I don't agree. I see this differently. This is one of the reasons why I think weird is different from authenticity. It's not quite the same thing. We all know we talk a lot about authenticity and leadership and be genuine, bring your whole self to work. I'm all for it. But weird is not that. I would describe authenticity as more about you and being true and honoring who you are. Weird is like that. It's knowing what makes you you, but what makes you great, and then you having the confidence to put it out there, to show other people it, to use it. It's the way that you understand this is the way I do my best thinking. This is the best way for me to build relationships. This is how I actually get results. Even, okay, this is what I'm able to see and understand. Maybe other people don't. You know, think about weird Al. He's not just authentic. Again, he's got that cool combination of talent with PS once again. No need to be cool. But he didn't just accept, I'm a weird guy. He used it. Or I think about that CFO. He hears, okay, you need to be tougher. He's not ignoring the feedback, but he's saying, once again, how do I deliver that in a way that works for me? So authenticity says, be be yourself. Weird says know what makes you great and use it to be a better leader. Trust that. So I want you to like find your weird. Think about when you're good, you're leading well, you're making good decisions, you're getting results. And once again, ask, what am I doing right now? What's going on in these moments when I'm at my best that is so distinctly me? And then am I actually using enough of this? Once again, I want to say we all get feedback about what a successful, you know, senior leader executive is supposed to look like. But once again, we want to be careful. We don't want to edit out the things that make us great, different, weird. One more thing I want to say. The word weird, I just learned this is a word that comes from the old English word weird, spelled W-Y-R-D, meaning fate or destiny. How great is that? I love that. You know, weird is your destiny. And those two meanings are not as far apart as they seem because again, your weird isn't something you need to get past on your way to becoming great. It is part of how you become great. That's the true confidence. It's being the weirdo, being the weirdo, knowing what makes you great, and having the courage to use it. And I'll leave you today in executive land with the wisdom of the biggest weirdo of them all, weirdo. Today is plaid, and your lucky number is potato. No idea what that means. All right, weirdos. I will see you in executive land. Until next time. Thanks, everybody. Well, that's all for today in Executive Land. Thanks for listening. And if you're looking for more, check out my website, essweetleader.com, where you'll see all kinds of free resources and take the free executive readiness assessment. It shows you exactly where you're strong and where to focus next in your own leadership. And don't forget, subscribe to this podcast so you never miss an episode. I'll see you next time in Executive Land.
