Start With A Win - Henna Pryor: How to Stop Being Awkward

Episode Date: March 18, 2026

In this lively and eye-opening episode of Start With a Win, Adam Contos sits down with Workplace Performance Expert and bestselling author Henna Pryor to unravel one of the most misunderstood emotions in modern leadership: awkwardness. With humor, science, and refreshingly real stories, Henna exposes the hidden ways awkward moments shape our confidence, communication, and ability to lead under pressure. Together, they explore why today’s increasingly “smoothed-out” world desperately needs leaders who can navigate discomfort with authenticity and courage. This conversation invites listeners to rethink what being confident truly means - and why embracing the messy, human moments might just be the ultimate performance advantage.Henna Pryor, CSP is a Workplace Performance Expert who helps leaders and teams elevate their performance mindset, communication, and interpersonal effectiveness. A regular Inc. Magazine columnist and 18x award-winning author of Good Awkward, she blends two decades of experience with a science-backed approach to taking strategic risks and boosting social and mental fitness.  A global keynote speaker and clients’ self-described “secret weapon for impossible change,” Henna has spoken at TEDx and SXSW and is featured in outlets like FastCompany, INSIDER, HuffPost, NBC, and FOX. She’s also a SUCCESS Magazine Woman of Influence, LinkedIn Learning Instructor, Glassdoor WorkLife Pro, and her book was named a Kirkus Reviews Best Book of the Year.00:00 Intro01:27 Did you just want to fit it? The three word tag line…04:26 Is this parallel to this? No, it’s this!07:05 Name the awkwardness that exists in the situation.11:30 The best tip!16:01 Do you use AI and how?18:55 This first then this second…21:28 I snuggle my puppy however this is the best way that will help most.www.pryoritygroup.comhttps://www.linkedin.com/in/hennapryor/ https://www.instagram.com/hennapryor/===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook  ➡︎ https://facebook.com/AdamContosCEOTwitter  ➡︎ https://twitter.com/AdamContosCEOInstagram  ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory

Biggest myth is that confidence and awkwardness are opposites. You feel awkward, you don't feel confident. That is a bold-faced lie. Welcome to Start With a Win, where we unpack leadership, personal growth and development, and how to build a better business. Let's go. Coming to you from Area 15 Ventures and Start With a Win headquarters, it's Adam Contos with Start with a Win.

Have you ever had one of those high-pressure moments at work where things felt awkward? And you thought, I wish I knew how to handle this better. My guest, Hena Pryor, has made it her mission to help leaders do exactly that. She's a workplace performance expert, award-winning author of Good Awkward, and a two-time TEDx speaker who's worked with global giants like Google, J.P. Morgan Chase, and Johnson & Johnson. Hena's insights have been featured everywhere from NBC to the Washington Post, and her playful science-backed approach helps people take smarter risks, sharpen their communication, and thrive even when things get uncomfortable. awkward. Hanna, welcome to start with a win. Thank you for having me. Excited to be here. This is a really cool topic because we all feel this way, but nobody really ever acknowledges it or really has any information to put behind it. So let's talk about awkwardness today. First of all,

how did you get into being kind of the awkward expert, if you will? And, you know, what's your history look like? Take us through that real quick. Sure. I have to first laugh at the irony of the cool topic of awkwardness. I think it is by virtue of the topic, it's sort of uncool. But yeah, yeah, this is, this leads greatly into your first question, which is I felt awkward my entire life. I am a firstborn of immigrant parents. And so my food always smelled funny in my lunchbox. My clothes were never quite the same. My name is Hannah. I grew up in, you know, born in 82 where Hannah Barbera was the thing. And so constantly my story felt like one of my bumpy edges sticking out when all I wanted was to fit in. And the way I got into the work professionally is, you know,

I am an executive coach and speaker by trade. And Bray Brown used to have this expression in her podcast interviews. She used to say, stay awkward, brave, and kind. I heard her start saying that as a bit of a tagline. And my entire body had this reaction of brave, yes, kind, got it, but stay awkward. Have you met me, Bray? I don't know about this one. And I got very curious about that emotion and the role it played, especially at work and in business. It's interesting because I used to have a co-worker, and anytime something interesting happened in a conversation or a meeting or whatever, he would always go awkward. And it would really knock everybody off of their game in the room.

But you say awkwardness is universal. But obviously, most of us trying to hide it. We try and push past it. We're like, yeah, that was weird. And let's move on. but why do you think leaders should embrace this and lean into it instead of just kind of covering it up or ignoring it? Yeah. So just the level set a bit. Awkwardness in particular, it is an emotion of discomfort, but it's a little bit different than traditional just being uncomfortable because it is a social emotion of discomfort.

It's something we feel when we are, you know, flubbing or blundering or misstepping or a moment happens in front of other people. So we don't feel awkward when we're by ourselves. If I mispronounce your name and I'm just in my home, nobody's here to see me. I might feel something, but awkwardness isn't it. It is a social emotion. And so for leaders and entrepreneurs and business owners especially, this is meaning that we are feeling this emotion in front of other people. And it is not something that, frankly, we can avoid. It is universal.

There's no avoiding awkwardness because to avoid it means avoiding uncertainty, which if you've cracked the code on that, good luck. Please share with the class. We'd love to know. And the second thing is, is the reframe really exists in this place of this emotion is evidence of stretching, of learning and growing. Yet somehow our natural instinct is to hide the process. We want people to just see the outcome. And so really reframing our relationship with that emotion is critical to us actually stepping into that next wave of growth. We're putting a ceiling above us when we try to smooth it away.

smoothing it away is not an option. So we have to look at it a bit differently. So is this parallel to the imposter syndrome at all? Or? Somewhat. Yes, it's related. Yeah, I think what I like to think of is it's parallel to self-doubt. And I think a lot of people confuse and synonymize self-doubt and imposter syndrome. I don't like the phrase imposter syndrome. I think, well, A, it's often unfairly used with women. And B, it is not a syndrome. Not one of us. has been born afflicted with the syndrome. When we use that expression, what we're experiencing is very normal and very healthy feelings of self-doubt, feelings of awkwardness. Now, I want to

underline a word I keep using there, which is feelings. We are not impostors, nor are we awkward, because guess what? Go into a dictionary. You will see there's no such thing as an objectively awkward person. It is an emotion. So rather than I'm feeling or, rather than I am awkward or I am an imposter, I'm having imposter thoughts. I'm feeling awkward right now. When we recognize it as what it is, which is a transient state in either case, we can actually use it as a force for our development rather than something that, again, limits us in a way that's not helpful.

Interesting. All right. Let's keep unpacking this here. Because you talk about awkwardness and doubt and those being connected. Well, I think it's, I'm going to take a side road here. all of my sales friends and, you know, doing a lot of work in sales, things like that, you know, the number one reason why people don't sign a deal is fear, doubt, and overwhelm. Yeah.

Okay. So doubt being kind of the center pillar of that. How does awkwardness fit into trying to get a deal done? Because it's kind of wacky when you're sitting down, like take a real estate transaction for some reason. and people are like, you know, there's something in the back of their mind or in their gut or whatever it might be. But maybe it's probably awkwardness. I've never heard of call that. But, you know, tell me your take on that.

Yeah. So I'll be very concrete. I spent a decade and a half in executive search and staffing. I was 100% commissions. So this is very personal and very real for me. So there's a few things happening that you've mentioned. First of all, let's make the difference between healthy self-doubt and unhealthy self-doubt. when trying to close a deal. So if you are entering a sales conversation and you're trying to get a deal over the hump

and you're experiencing that self-doubt, that feeling this is going to be an awkward conversation, there's two different kinds, and I want to make sure we make the distinction. Healthy self-doubt is the kind of self-doubt that makes you say, okay, I need to read up on this client even more before going into this conversation. I need to make sure I think of all the different objections that might come up. I'm going to go have a sparring match with chat GPT. I actually encourage my clients to use AI to come up with different perspectives of where some of those blocks may come up, healthy self-doubt inspires you to prepare harder, to research a little more, to be more ready. That is very different from unhealthy self-doubt. Unhealthy self-doubt or an unhealthy, you know, awkwardness running through your body paralyzes you. It freezes you from taking action. It makes it so that you don't pursue the conversation

further. You kind of, you know, back off or walk away when there was potentially more meat on the bone. unhealthy self-doubt is not good for our career. Healthy self-doubt is great for our career. I don't know a single high-performing individual, a single high-performing seller that doesn't experience some form of healthy self-doubt if it inspires us to that next level. Now, in that moment, when we're trying to get a deal over the hump,

one of the best things we can do is name some of the awkwardness that exists in those types of conversations. Some of that might sound like, listen, I totally get that there is probably a pretty real fear of you making a mistake here, of moving forward and not knowing if it's going to be the right thing. To say that as a seller feels incredibly awkward. And that's a muscle that we can develop. But in fact, that's often the thing that helps us get our outcomes over the hump is getting more comfortable staying in that messy middle with our clients.

Interesting. Interesting. Yeah, this is a fascinating conversation. What's one of the biggest myths about awkwardness that keeps high performers from taking bold action, do you think? I mean, it's, you know, people freeze at the door is before they walk in and, you know, or here comes the client. But, you know, is there, are there any big myths that you have people quickly overcome or that maybe it takes a while to chisel away at? Sure. Yeah, actually, my book, I talk about three of them, but I'm going to be the number one that really sits over all of them.

But the biggest myth is that confidence and awkwardness are opposites. Interesting. Right? You're a confident person or you're an awkward person. If you feel awkward, you don't feel confident. That is a bold-faced lie, I'm going to say more than a myth, because the most confident people in any room experience the emotion of awkwardness just as much as the people who self-identify as awkward.

They've just made peace with it. They've worked on their comeback rate. So, again, awkwardness exists in uncertainty. We don't have a crystal ball. You can't predict how the person across the table is going to speak to you, respond to you, but they've learned how to improve their comeback rate. When something goes sideways, they either name the tension in the room. They use humor to diffuse it. They have a strategy to use improv techniques to stay in the conversation rather than shut down or let the embarrassment or, you know, fluster take them over. But confidence is never, I don't mess up. The most confident people we know, we look at the them and we're like, they really own that moment. They messed up and they just like, wow, can't believe I did that. Ooh, that was embarrassing versus the people who try to stay stuck polishing to oblivion. They stop progressing.

It's about comeback rate, but they are not opposites. They are two sides of the same coin. What does comeback rate mean? How do we define that? Comeback rate is our willingness to have one of those moments. Stay in it, own it, and then quickly recover. It's a recovery rate. So, for example, Adam, I get onto this call with you and I just, you know, I'm mixing up

something from the morning and I said, you know, I was so excited for this conversation with Adam Smith. And I realized, well, your last name is not Smith. So I can sit there and go flush in the face. I can let it throw me off my game. But if I'm someone who has worked on my comeback, right, I can go, oh my gosh, Adam, did I just say Smith? That is not your last name. And that's embarrassing.

But hey, we're having a conversation about awkwardness today. So we're just going to roll with it. That is an example of comeback rate, of disarming the moment as quickly as possible and moving on. In other contexts, I'm able to use that. The brilliance of writing on this topic is that every time I've loved, I can use that. But in other cases, it could just be, wow, that's embarrassing. Let's just flush that one away and keep going. You can just disarm in a number of different ways.

But that is what we perceive as the confident person, the one who owns, the one who names, the one who can laugh about it and the one who helps it quickly move on. That is a really important tip there because as a leader sitting in a room, at a meeting, whatever, you're going to screw up. I mean, you're going to throw something out there and you're going to be like, oh, I wish I could pull that back. But now you got to own it. And a lot of people try to avoid it, which I think is totally the wrong way to approach

those things because they're like, all right, now it becomes the elephant in the room. Whereas if you call it out, it's going to. blog. And so, and I love this confidently awkward thing. I think I can be confidently awkward all day long. You know, I need a t-shirt. It says confidently awkward. Listen, it's more sustainable for most of us. Oh, totally. Totally. And I like your comedic approach to it as well, you know, kind of understanding some improv techniques, things like that. Because that's really what comedy is, is creating an awkward situation and then moving on from it, it seems like. Exactly. But yeah, tell me, what's the most awkward thing you've heard somebody do? Because you, you, You've had to have heard some crazy stuff and you're studying and become an expert on this.

So what's something fun? How do I choose? Okay, here's something fun. I was talking to a friend of mine and she had to give a presentation at her all associates meeting. So this is, I think, all 500 people in the organization. They had a company offsite. She had to give a presentation. She's involved in public affairs.

And so her title slide said something, public affairs in giant letters, biggest letters, because it's the title slide, the L never made it onto her title slide. So she's talking for about five minutes before she switches the slide and in giant letters with a video camera, you know, IMAG, close up, says pubic affairs on the back. And she, you know, people were snickering. And here she was, what am I saying is my fly down? But she realized, and here's the greatest thing. When we talk about comeback rate, obviously after that moment, she felt, she felt, she felt

mortified, but somebody came up, a friend came up afterwards, told her why people were snickering. It became something she joked about the rest of the conference. She goes, well, you know, this is, we're going to set the meeting next week, marketing and pubic affairs. And she just, she owned it. She owned it. And because of that, it's kind of become this inside company joke and it actually bonded her to a lot of her cross-departmental peers because it gave them all this opening thing that they could have a shared laugh over. Shared laughter creates, you know, oxytocin, it creates dopamine, it creates instant bonding, those pro-social hormones. It actually ended up being one of these surprising best things that ever happened to her.

I was going to want to manufacture those moments. But when they happen, they're pretty great if we own them. Right, right. And, you know, I guess that sort of answers the question, but also I think it opens a door for reality here because, you know, while you don't want to make that stuff up, because I think it's pretty obvious when you try to make up an awkward moment. And then it turns into a little bit of a malicious moment, if you will. But it's, it seems like those awkward moments are the things that build the biggest bridges in relationships, don't they? Today, more than ever, the world has optimized for smoothness.

I mean, in every facet of our lives, on social. media filters make it so that I have no pores and a tiny nose, right? We're smoothing out. Our interactions are increasingly asynchronous. So when we don't have that messy friction that happens when we're in proximity, look, Adam, in our conversation right now, if I trip over my words or you trip over your words, we can edit it out. No one will be any of the wiser. In real life, we can't edit it out. So increasingly, I think those moments that are just very human, very unseen increasingly behind the curtain are the things that bond us and unite us in a way that 10 years ago we would have laughed that this is even a helpful sticking point anymore.

But it is. It is the thing today that makes us remind each other of what our humanity is actually made of. They're incredibly helpful right now. That's awesome. Hey, you mentioned chat GPT and sparring with yourself on that. I was going to ask you, before you even brought that up, I'm like, how do you incorporate AI into this?

Tell us how you do that. Do you prompt it a certain way? Or how do you have a sparring match about awkwardness with chat GPT or GROC or whatever? Sure. Okay. So I actually have a, you know, shameless plug. I have two LinkedIn learning courses that came out on this. They're free for the first 30 days.

You can go check them out. But on AI and interpersonal skills and AI and influence. And the way I think we can use AI. So level one AI is actually the thing that removes all of our awkwardness. Level one AI use is clean up my email. also there's not a spelling error to be found. You know, summarize my meeting notes, so we have nothing extra in there. That's smoothing.

Level two AI is where I think we can really use our awkwardness muscles. And so that is how do we create additional perspectives in order to help us embrace whatever conversation comes at us? So I'll just give you one concrete example. If you are an entrepreneur, business owner, you're in sales, you can have a conversation with AI and say, hey, I'm about to meet with a client. We're about to have, you know, this presentation that we're going to do. deliver. Here's some context. Please give me an example of the client's response, but in three formats. I would

like a cooperative response. I would like a resistant response. And just for fun, I would like a distracted response. AI will give you three examples that fit all of those. Cooperative, great. We love that. That one is our best case scenario. But what would a resistant response potentially sound like? What would a distracted response potentially sound like? Either of those have the potential for us to invite those feelings of awkwardness of, oh, this isn't going the way I wanted it to go. But by just having an example ahead of time, our brains are more prepared. We don't have to experience that feeling for the first time. We get to scrimmage it before the big game. And, you know, in sales, I think it's pretty old wisdom, you know, get ready to stay ready. Don't go in there and wing it.

The separation is paramount. The separation is in the preparation. How do we go in with a little bit more wherewithal of the situations that might occur? AI now gives us really unique ways to scrimmage those potential moments gone sideways before they even occur. We still have to deal with them in the moment, but our perspective is larger. Our aperture is wider. So it's just really helpful for sellers. This is great. And I mean, think of how much money you're saving paying a business coach or something like that. You're talking to Chad GPT. Both end. Tell us about good awkward. I mean, it seems like you've got a lot of great information here. I'm assuming this is all in Good Awkward. Tell us a little bit about that book.

Yeah, no, this book was, you know, I don't know that I ever asked the beginning, how did you become the awkwardness girl? I don't think anyone is a kid sets out to become the awkwardness expert. But I was invited to do a TEDx on the topic. And as I got into that research for the TEDx, I realized there was so much there. So the thesis for good awkward is, as you can probably guess, awkwardness as an emotion is not a deficiency. It's not a weakness. It's not something to run from.

It's those who actually lean in and embrace it that experience the biggest courage, the most risk-taking, the more innovation, the more career growth. You know, that is what we learn. What's really interesting is some of what shook out in the research. There's all these phenomenons that people were not familiar with, like vicarious embarrassment, for example. So Adam, you and I both know empathy is a. superpower. We want people to be empathetic, but what most people don't know is if you're very high in a specific type of empathy, one that's referred to as easily empathetically embarrassed, meaning you feel embarrassed for other people a lot, they flub up in a conversation. They mispronounce

something in a presentation and you, and you know, if this is you, you know it, you want to climb underneath the table. You're like, oh, I can't believe they did that. Right? If you're very, very high on that form of empathy, it's actually going to be very challenging for you to take risks to yourselves, for you to try to do things and advance your career. So there's some really neat explorations, but I think awareness first, action, second, but if we can learn to understand our awkwardness, our embarrassment, we can learn to harness it for our growth in a very meaningful way. Awesome. Make sure you check out good, awkward, where you get all your books. Hannah's got some great information here. Also, you can check out Hena.

at priority group.com. That's P-R-Y-O-R-I-T-Y-G Group.com. Hena, we have a lot of great leaders on this show that deliver a lot of great information. You've dropped some huge, huge value bombs on everybody here. And I think we all have a lot of reflection to do on kind of those awkward moments and actually how to capitalize on those for the most part. I mean, it's interesting because we always leave a meeting or like, oh, that was embarrassing. But I love how this ownership connection you have really magnifies your delivery of leadership, as well as, you know, the connection with the people in the room. We all start our day a certain way.

And how we start our day, hopefully you start with a win, is a good way of, first of all, decreasing the awkwardness in our day, but also increasing our confidence and our growth. Hena, how do you start your day with a win? Okay, well, I first always snuggle my puppy, but I don't think that's as helpful. So after I do that. That works for me. I agree. Here's the one that's related to my work is I think one of the most powerful things we can do,

but can often feel the most awkward is complimenting others. It's always something we want to do in our minds intuitively and cognitively. We know it's a good idea, but we don't do it because we were like, oh, it's creepy, it's weird. You know, I don't know how people are going to react. But I make a point, at least a few times. week, if not every day, to just reach out to somebody in my network, someone who I care about a lot, or someone who's a weak tie, and just throw out a compliment. It can be as simple as, loved that LinkedIn post you shared yesterday, really got me thinking. It can be as deep as really

miss you. We haven't talked in a while. Just wanted you to know you were on my mind. But when I get into practice of starting the morning like that, again, it does feel a bit awkward sometimes, especially for those weak ties. It is the best start to my day because inevitably I get something back. It's like, you just made my day. This was such a great way to start the day. And so I feel good. They feel good. It is a beautiful way to start a day. I love that. And that does feel awkward to people to reach out to somebody they haven't connected with in a while, especially in sales. But overcome that awkwardness. Make it good, awkward folks to quote the title of the book here that Hena has written. Make sure you check out Hena online, also on the social. She has a lot of great information out there.

also on a lot of different podcasts. Hena, you, you're making the podcast circuit and you're delivering a lot of truth and value here. So thanks for what you do and thanks for being on Start with a Win. Thanks for having me.