Leveraging Awkward Moments for Business Success | Henna Pryor

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 How embracing discomfort fuels stronger leadership and communication

Awkwardness isn’t a weakness—it’s an opportunity. Today, we explore how embracing discomfort can lead to stronger leadership, better communication, and personal growth. From handling tough conversations to overcoming the fear of failure, we break down why leaning into awkward moments can set you apart in business and thought leadership.

Ever felt awkward in a meeting, on stage, or in a tough conversation?

What if that discomfort wasn’t a weakness—but an advantage?

In this episode of Leveraging Thought Leadership, Peter sits down with workplace performance expert Henna Pryor, author of Good Awkward, to explore the hidden power of social is comfort. Henna breaks down why avoiding awkward moments only makes them worse—and how embracing them can lead to stronger communication, better leadership, and a more resilient mindset.

They discuss why so many leaders fear saying the wrong thing (especially in today’s hyper-visible world), how the “spotlight effect” distorts our self-perception, and why placing small bets is the key to building a thought leadership platform. Henna also shares her journey from finance to executive coaching to keynote speaking—proving that growth often comes from stepping into discomfort.

This conversation will change the way you think about awkwardness—and might just help you unlock your next big leadership breakthrough.

Three Key Takeaways

Avoiding Awkwardness Makes It Worse – Awkward moments happen to everyone but dodging them only amplifies the discomfort. Acknowledging and embracing these moments can make you appear more confident and authentic.

Small Bets Lead to Big Wins – Instead of making massive, risky moves, successful thought leaders test ideas by placing small bets—through LinkedIn posts, speaking engagements, or content experiments—to see what resonates before doubling down.

Your Perceived Failures Matter Less Than You Think – The “spotlight effect” tricks us into believing people notice our mistakes more than they actually do. In reality, most people quickly move on—so stop overanalyzing and keep moving forward.

Awkward moments often come from misspeaking or making mistakes. Just as Henna Pryor suggests addressing the awkward head-on, Priya Nalkur encourages leaders to embrace imperfection. Both perspectives highlight the power of authenticity and resilience in leadership. If you want to learn how to turn your perceived flaws or failures into strengths, don’t miss this episode 554 – Embracing Imperfection!

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Transcript

Peter Winick And welcome, welcome, welcome. This is Peter Winick. I’m the founder and CEO at Thought Leadership Leverage and you’re joining us on the podcast today, which is Leveraging Thought Leadership. And today my guest is Hannah Pryor. I’ll give you her quick bio, which is she is a dynamic workplace performance expert who speaks and writes about performance, mindset, interpersonal dynamics, high impact communication, and embracing bumps in a world that keeps optimizing for smoothness. She’s a regular expert columnist for ink. She’s the author of Good Awkward. She’s a keynote speaker. She’s done a TEDx and she’s here. So I’d rather talk with her than about her. So welcome. How are you?

Henna Pryor Thank you. Thank you for having me. I love there’s something that we have to giggle about with the word smoothness being so hard to actually say Why?

Peter Winick But awkward, one can say easily.

Henna Pryor One could say. One could say. I was hoping you would say it, not me. But yes, I think that’s the theme. The theme of the year seems to be.

Peter Winick Awkward. Yeah. Yeah. Here we go again. Let’s start with, you know, how did, how did all this happen? How’d you get here?

Henna Pryor So if it’s not too arrogant sounding to say so, because I think we should start with this, it all has happened quickly. When we talk about this here, proverbially, this here, my journey has been, I think, relatively quick. So quick history, my first career out of college was big four public accounting. I was a finance major. I was recruited by Ernst & Young. They paid for my master’s in accounting. I was an auditor with the CPA, quickly realized that That was not. the right role for me. I have too much personality and desire to speak to do that. So, I had to change it.

Peter Winick There’s exactly as much personality for an audit. I would say that bar is fairly low.

Henna Pryor It’s funny, because in audit, you’re actually quite client -serving, but there still is a head -down, you know, at the time it was red pencils. I think I wanted to talk to people a lot more than I currently was in that role. But from there, I transitioned. I wanted to use my finance and accounting skills, but in a more people -centric way. So I transitioned to 14 years in search and staffing, where I was mostly doing direct hire placement. And frankly, that gave me a front row seat to what made Teams work. what made leaders successful, what made them keep people. And when I exited that career after 14 years, I found myself doing executive coaching, which very organically morphed into, hey, I love what you did with me. Can you do it with my team? Can you do it with my department? Can you do it on stage in front of 1500 people? And so that is how I get to spend my days now is largely on stages and in pages, writing for both a column and my book.

Peter Winick Very, very cool. And, you know, there’s several threads underneath that going from, you know, employee to entrepreneur, right. And that totally different path. Right. I mean, an auditor definition is kind of a historian of sorts. Right. And when you’re placing people, you’re in the present, if not the future. It’s about the whole optimism and getting all that done. So how did that lead you to sort of the good awkward? Cause that’s, that’s an interesting concept. So where did that come from? So I love that it’s real stuff. This isn’t some academic, I studied, you know, whatever theory, but you probably saw things and saw patterns that led you to go ahead and go, hmm, let me learn about that.

Henna Pryor Very, very much so. I think, you know, while I love to read about social psychology and organizational dynamics and all the things that inform my work, where this became urgent for me was a couple things. In my 14 years of staffing, I would see leaders and teams kind of claim the same excuses for why there was turnover or why they couldn’t retain people while refusing to have the very types of conversations with themselves and with others. that would actually move the needle because they were afraid of how it would be received or that they would say it wrong. Or this kind of was the heyday of people realizing that in this fishbowl world we now live in, that everything they do is theoretically on display, right, their mistakes, their missteps, their embarrassing moments, which was at that time a kind of new phenomenon. We used to be able to make our mistakes and our blunders in relative secrecy or only in front of the people who were in the room with us. now it felt like all of those things had a spotlight on them. And so, you know, awkwardness in particular, it’s an emotion of discomfort, but more uniquely, it’s an emotion of social discomfort, meaning we don’t tend to feel it when we’re by ourselves. We feel it in front of other people. So I would see leaders increasingly worry so much about getting it wrong, not saying it right, not addressing the elephant in the room, that instead all of these kind of issues would build in quiet and then never get solved for.

Peter Winick So what’s the Delta between what I, what I would say is perceived awkwardness and actual awkwardness, right? So I’m in a meeting and I mispronounce something or do something wrong or blah, blah, blah, blah, blah. And now I’m obsessing on that. Oh geez, I should have said customer, not whatever it is. And thinking, oh my God, everybody thinks I’m an idiot. This is the end of the world. And then I’m five steps from homelessness versus people in the meeting were like, yeah, he kind of flubbed it, but then they went on a day, like get over yourself, like, is that, is that See ya!

Henna Pryor Yeah, that’s absolutely a thing. There’s two things that come to mind there. Number one is there’s no such thing as a factually awkward person or a factually awkward moment.

Peter Winick that there’s not a standard of awkwardness like you’re, uh, crusty. I don’t have an awkward.

Henna Pryor Of course, no, I mean, listen, we can, we can grade ourselves all day. There are, there are measurable things like self -consciousness and, and things like that, but objectively, there’s no such thing as that was an awkward moment on a scale of one to 10. That’s up to us to decide. We get to decide either ourselves or another gets to decide what they deem that to be for some, that was nothing we forgot about it. The minute it happened for others, especially those who are high at a specific type of empathy, they might not have even had the moment. somebody else might have, and they’re sitting there carrying that going, oh my God, did you see how Peter, like, it has ruined their day. And so A, it’s just helpful to anchor in that truth. It’s subjective. You are deciding or someone else is deciding what that awkward moment is worth. But secondarily, and I think kind of a famous piece of research in professional development is, you know, Tom Gilovich from Cornell talks about the spotlight effect. We think everyone’s paying much closer attention to us than they are. Maybe for a blip they did say, oh, that was embarrassing for that person. But guess what? They are already thinking about what they’re about to say next. We need to stop giving it so much power.

Peter Winick So now that you’ve defined it that way, what is your experience with either your coaching clients or the teams or the orgs once they get exposed to it? Because what I find in, in my work with lots of authors and ball leaders and such, once you can language models, frameworks, and definitions are really, really important because instead of me saying something, let’s say you did something awkward, whatever, if I didn’t have the language of the war, we didn’t have the language of the words for me to have that conversation with you or not have that conversation with you. You know, that’s one thing putting it out there and defining it in such a way gives organizations and teams and people an opportunity to sort of hone in on it. How are you experiencing that?

Henna Pryor Yeah, I share your ethos around this. I think what I really believe and I don’t, you know, I wasn’t a trained linguist in college, but I really believe in the power of language and sometimes just having shared words or a deeper understanding of words to describe a phenomenon is so helpful to A, bring it into the air, right? Diffuse the tension of something and B, help us understand how something might be stopping us in the past or in the future. yourself. With awkwardness in particular, here’s a, here’s a great example of the words usage. Yeah. The biggest thing that will make an awkward situation worse is the avoidance of said awkwardness, right? The avoidance of awkwardness increases awkwardness. So someone says something, maybe didn’t realize that it was off color and no one says anything and you’re all sitting there.

Peter Winick or squared, right, so by not early if –

Henna Pryor the tension actually thickens and all it takes is that one person to do one of several things, either name it, oh boy, that was a misstep, that was awkward, blunder, right? And we actually look at that person as the confident person, the person who is quick to name it. They can use humor strategically, right? There’s some hierarchy thing, you know, that come into play. But there’s a number of things that we can do and what’s ironic is that when we actually train ourselves to use those tools in those moments, we actually look to that person. as the confident person. They feel the most awkward and yet appear the most confident. It’s very paradoxical, but it’s the reality of our current climate.

Peter Winick Well, and there’s a line between that and sort of, you know, self -effacing, right, right. So if you could call out your own stuff, that does take confidence as opposed to brush, right? So wow, that was really dumb. When I said that, like, you know, everybody in the room is going, Yeah, we thought that too. But nobody wanted to say it. Thank you for saying

Henna Pryor Right. And one of my favorite stories in the book, it doesn’t come toward until towards the end, but I was working with an executive, my friend, Bob Russo, that worked for IBM for 20 years. And he shared a story about how one of the executives in a meeting made a comment that just, it did not go over well. It was the beginning of the meeting. The room fell silent. Everyone was kind of giving each other eyes like, Oh God. And the next comment out of his mouth was, Oof, that went over like a fart in church.

Peter Winick Yeah, right. Except…

Henna Pryor And everyone laughs and everyone’s shoulders fell and not only was he able to kind of diffuse the tension in the room, but it also made the rest of the meeting far more productive because people had this sort of modeled permission slip of not getting it exactly right. Now, again, there’s rules around self -deprecation. You don’t want to deprecate on something that is supposed to be part of your technical skillset or, you know, certain facets. If you’re lower hierarchy, you have to be careful about what you say, but there’s so much value. owning our stuff because right now there’s too much sweeping under the rug and it’s creating longer issues down the road.

Peter Winick If you’re enjoying this episode of Leveraging Thought Leadership, please make sure to subscribe. If you’d like to help spread the word about our podcast, please leave a five -star review at ratethispodcast.com/LTL and share it with your friends. We’re available on Apple podcasts and on all major listening apps, as well as at thoughtleadershipleverage.com/podcast.

Peter Winick With regards to, let’s say, DEI, so there’s a problem right now that people are afraid to say the wrong thing. Like, there’s two problems. One is, as you said earlier, sort of we’re on the record all the time, right? Like if I would have had a bad meeting 15 years ago, it would have passed, but now everything’s on Zoom and everything’s kind of on the record. You don’t know what’s being recorded, what’s not, whatever. So things could live in perpetuity, whether it’s an email, whatever. And then there’s this I’ll use your awkwardness that some have or fear of having that connects to DEI. If I don’t use pronouns, if like, I’m an old white dude, right? Like I, and I consider myself a decent human and evolved and I’m open to everything. But some of it is just, I didn’t grow up with using pronouns in that way. I was English mired. It actually almost hurts my, not an excuse, right? So sometimes those two things together seem like it’s easier to say nothing sometimes. and not feel stuff how does so I guess what I’m saying I think there’s times where you have to know that something will be awkward. And it is going to be awkward irregardless of how you

Henna Pryor Yeah

Peter Winick Yeah, try to – Yeah, that’s okay.

Henna Pryor And I think that’s the key, which is stop expecting it to feel easy. You need to recalibrate your expectations. If you have 40 plus years of conditioning of something being a certain way, and you are now trying to do it differently, you are holding on to some silly expectation that this is supposed to feel good or feel easy, then you’re doing yourself a disservice. For those, I am a woman of color. I still struggle with it. I’m someone who’s been sensitive to this her whole life and I still struggle with it. So, yeah, I think there’s two. points to this in particular. Number one is it’s the start that stops most people. I learned that phrase from my friend Colin. It’s the start that stops most people. It’s the idea of even trying where most people will tap out. So a little mantra that I have in the book is do it awkward, but do it anyway. Don’t worry about feeling good about it, just do it. And I think a lot of times when we think about that start stopping us, we are not giving power to the idea that there is a such thing as the circle back. you’re probably not gonna get it right. And that’s okay, if you don’t get it right, you know, you can say to that person later, you know, I realized that wasn’t quite what I hoped for. Or I didn’t say that as articulately as I would have liked to, but I hope that, you know, you can maybe help say that better in the future.

Peter Winick I like the ability to name it. Cause I could say to you, Hey, this is a little bit awkward for me to have this conversation with you, but when you asked yesterday, why, whatever it was, but even just setting it up to say, cause you’re probably feeling awkward too. So I want to keep it for the last several minutes that we have here. Let’s talk about the business side of this. So as a, as a thought leader, there’s lots of ways that one could get their work out there and, and have it have impact. And there’s lots of ways you can monetize it. So talk about. that path, some of the trials that you’ve had, experiments you’ve had, what’s working, what’s not working, et cetera.

Henna Pryor Yeah, I think probably not dissimilar to your past guests. I have plenty of failed projects under my belt. And guess what? You probably don’t know about them because I soft launched them. A few people did it. Nobody else really cared. And it doesn’t really matter anymore. Nobody’s paying attention. And so one of my…

Peter Winick Stay there a minute, though, because I think there is a lots of thought leaders are perfectionists. They’re proud of what they do. They’re smart, and they’re passionate. But like any other business, lots of things that you put out there will fail. And I think a lot of the conversations I have with my clients are nobody’s gonna die. Like, think of it because words matter. Let’s try an experiment because by definition, some experiments fail and some succeed versus Oh my God, if I put this thing out there in it and the market doesn’t go to it, I’m a loser, I’m a failure, this is terrible. So I sort of, what is the viable, whatever you have to put out.

Henna Pryor So I’ll give you my language. So you use the word experiment. I actually tend to use the language of my, my business success has come from placing small bets. Yep. So I, you know, a bet is the same thing, which is by nature, sometimes a bet will win and sometimes it will not, there’s no such thing as a constantly winning bet. I mean, that’s not, you’re not placing a bet then by definition anymore, but when I’m not a huge gambler, but occasionally when we, we go participate in Vegas. You know, the thing about bets is when it goes well and you’re on a hot streak, you double down. If people like what’s happening, you double down. And guess what? If it’s not going so well, you stop doing it. That’s the value of a bet.

Peter Winick You said small, if you’re, you know, you walk into Vegas and your total bankroll is picking, you know, whatever, $1 ,000, you’re not gonna go up to one, you know, to the roulette wheel and make one bet for $1 ,000, right? Like, you’re just not, you’re gonna say, okay, do I start at whatever, picking up 25 bucks or 10 bucks or whatever, lots of small bets. And then, like you said, there’s, so I like the idea of the, because it’s the size of the bet. And I would argue that most thought leaders are very rarely, if ever, making a bet the house move. Right, they’re nuts. I always on that, you know, let’s

Henna Pryor Not unless they’ve done significant due diligence and research and have the comfort to make that smart decision. But you’re right. I think most of us are making a lot of small bets along the way and figuring out where do I want to put my stake in the ground and only then do we start to make those bigger bets. Right. But it takes a little bit.

Peter Winick some of those bets from the standpoint of, I find it, A, it takes courage. You got to put stuff in the marketplace, right? And then you got to shut up and listen because it doesn’t matter what you think. So tell me where you’ve been surprised on the negative and on the positive meaning, wow, this is my greatest thing ever. And, you know, nobody loved it. And then this one, you’re like, yeah, this is not going to work. them in. And people, uh -huh.

Henna Pryor Yeah. Okay. So, I mean, just let’s talk about one of my main topics of the last couple of years, which is on this idea of good awkward and awkwardness as an asset in the workplace. I have no idea if people would resonate with it. I mean, it came to me when, you know, A, that was my lived experience my whole life. So whatever confidence and poise you might think you see now is a product of a girl who felt relentlessly awkward her entire life, you know, daughter of immigrant parents. And Brene Brown used to say, stay awkward, brave and kind. That became one of her little tag lines. And I remember going, okay, I like the other two, but this one, lady, I like everything you do, but I don’t know if you know what you’re talking about here, which led to the curiosity around the emotion. And so when we talk about small bets, I wasn’t about to do a TEDx or write a book on this without knowing if other people were having a similar reaction to me. And so LinkedIn was where I started to place my initial small bets. I would start to write posts about it. And the idea was to test, are other people resonating? Do other people feel like I do around this? And over time, over kind of testing this over a period of months, I could see very clearly people are like, oh, I feel like you’re talking to me. I feel like you’re talking about my lived experience. That gave me the courage and the confidence to say there’s something here. There’s a population of people that are resonating, which turned into the TEDx first, that resonated, turned into the book, right? It was all a series of building actions that created that.

Peter Winick And lengthen is a great place to experiment with stuff out there. And it’s almost impossible to predict. Like you probably wouldn’t have been surprised if it didn’t get the reception that it did, because it’s not a conversation typically have had like, Hey, I feel awkward all the time. Do you feel awkward all the time? No crap. We need to put on this, this suit of armor. I feel great. I’m a success. I work hard grit grits a bit like I’m gritty or we’re gritty.

Henna Pryor Yeah, and so maybe to answer your reverse question, sorry if you can hear the dog, the reverse question about where did it not work? You know, there was a period of time where my business was starting to scale pretty significantly and so for a blip, I thought about hiring like a social media partner. To be clear, I love writing and I love ideating and I loved content creating, but I thought, okay, it’s getting pretty hectic around these parts. That was a mistake on a number of fronts because A, I realized I have a very strong voice. that is uniquely mine. And B, and maybe more importantly, this is where I am testing my ideas. This is my playground for experimentation and placing bets. And you cannot do that when you outsource that. And so I’ve learned very quickly that LinkedIn and social media writing is something that I will never outsource. Now, I’m not saying that there’s anything wrong with it. For some people, that’s not the best use of their time, but for me and the way I use it. That was a misstep to think that I would somehow gain more from letting that go. I’m glad that’s back in my view.

Peter Winick using more than you were gaining, right? Because it was forced to interface directly with the market for someone else. It might be, hey, I’ve been doing 30 years. I got a ton of stuff. Can you be my social media manager? Exactly. More of a posting issue. Exactly. Creating and experimenting and entering. This has been great. So there’s sort of lastly, someone’s out there in a position where you are five, six, seven years ago, where this was starting to become a thing. What advice might you give them if there’s something bubbling in their head? Like there might be a thing here. But I’ve got it Clarice, I’ve got this and I’ve got that.

Henna Pryor Can I give two? Number one, number one is have a point of view. You being a curator and a regurgitator or what everyone else has read and all the brilliant books that you have on your desk, that’s fine and it’ll take you to a certain point. But if you are not willing to have a slightly spicy, provocative point of view that is uniquely your own, it’s too noisy out there. Differentiation is so important right now.

Peter Winick double click on that I think part of having your voice is being okay saying you know what 1020 some percentage of the world maybe a significant percentage may hate this may not like this may not work. And that’s okay.

Henna Pryor I’m not for everyone. I am not for everyone. Mark Levy, my good friend Mark says, Well, you know, there’s, you know, Mark, so Mark has this great expression about mushrooms where, you know, I think mushrooms are disgusting, they’re slimy, they taste like boogers, they’re the worst. And the reasons I hate mushrooms are the exact reason that other people love them.

Peter Winick Exactly.

Henna Pryor Right? So yes, let go of that. And then the number two thing, which sounds so simplistic, but I feel like it needs to be said is one of the greatest things that has happened in my thought leadership and in my success in a business context is that I have been able to earn, you know, a few minutes of time from people who I really admire, who have been doing this a lot longer than I have. They are kind enough to give me advice and I do it. I take the advice that they give me and it is now, honestly, it makes me want to flip a table. Shocking to me. how few people actually do what these people suggest. So just do the thing, just try the thing. Don’t worry about doing it perfectly, just do the thing. But if there is a group of people that can just, if I could lovingly shake your shoulders, don’t ask for advice from people who you’re trying to learn from, and then have the same question six months later, because that’s how you quickly lose the mentorship or guidance from people that you want to help you elevate.

Peter Winick Yeah, well, it’s kind of like, why bother? I think what I would add to that is in general, like 99%, the thought leader community, however you define that, is incredibly generous and willing to share, willing to – Incredibly. Hey, here’s a word for like so, so willing, but I think you’re right. I’ve seen a lot of people that get a lot of brilliant advice and not do anything with it. I’m like, okay, well, what was the point of that? Like you just asked someone that’s world renowned or somewhere that is where you would like to be. They told you three things and you did none of them? What’s that? Like, why?

Henna Pryor Yeah. And we could, we could have a whole other whole other episode on this, but also know how to ask people who are very busy for their time.

Peter Winick I didn’t find this conversation awkward was it supposed to be like this wasn’t awkward or?

Henna Pryor I make it awkward. You know what, you know what wasn’t on our recording. Peter said something about us living happily ever after. So maybe we can we can insert that back in before we started recording. We love each other professionally and platonically. That’s it.

Peter Winick Yeah, a little dash of awkwardness because we’ve got to stay on brand though. All right. This has been great. Appreciate it. Thank you so much. Best of everything

Henna Pryor Thank you for having me.

Peter Winick To learn more about Thought Leadership Leverage, please visit our website at ThoughtLeadershipLeverage.com. To reach me directly, feel free to email me at Peter at ThoughtLeadershipLeverage.com. And please subscribe to Leveraging Thought Leadership on iTunes or your favorite podcast app to get your weekly episode automatically.