Henna Pryor: How to Stop Being Awkward

0:00Biggest myth is that confidence and awkwardness are opposites. You feel awkward, you don't feel confident. That is a bold face 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 Conto's 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, Henna 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, JP Morgan Chase, and Johnson and Johnson. Henna'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.

1:00Awkward, Henna, 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 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 odd and cool, but yeah, yeah. This leads greatly into your first question, which is, I felt awkward my entire life. I'm a first born of immigrant parents, and so my food always smelled funny in my lunchbox. My clothes were never quite the same. My name is Henna. 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.

2:01And the way I got into the work professionally is, you know, I am an executive coach and speaker by trade and Brenne 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. Then have you met me, Brenne? I don't know about this one. And I got very curious about that emotion and the role it played, especially at work and business. It's interesting because I used to have a coworker. 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 like, 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

3:02of covering it up or ignoring it? Yeah, so just a level set of 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 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,

4:02of 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 how does it look? 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 in imposter syndrome. I don't like the phrase imposter syndrome. I think, well, A, it's often I'm fairly 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.

5:04Now, I want to underline a word I keep using there, which is feelings. We are not imposters, 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 gonna take a side road here. All of my sales friends, and doing a lot of work and sales, things like that. The number one reason why people don't sign a deal

6:04is fear doubt and overwhelm. 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 awkwardness. I've never heard it call that, but tell me you're 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 gonna be an awkward conversation, there's two different kinds and I wanna make sure we make the distinction.

7:05Healthy 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 gonna 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 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 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.

8:07Now, 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 a probably pretty real fear of you making a mistake here, of moving forward and not knowing if it's gonna 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 here comes the client. But, you know, is there, are there any big myths that you have people quickly overcome

9:08or that maybe it takes a while to chisel away at? Sure, yeah, I actually, my book, I talk about three of them, but I'm gonna do you the number one that really sits over all of them. The biggest myth is that confidence and awkwardness are opposites. Interesting. You're a confident person or you're an awkward person. If you feel awkward, you don't feel confident. That is a bold face lie. I'm gonna 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 their 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 fluster take them over,

10:10but confidence is never, I don't mess up. The most confident people we know, we look at 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? I 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 rate, I can go, oh my gosh, Adam, did I just say Smith? That is not your last name and that's embarrassing,

11:11but hey, we're having a conversation about awkwardness today, so we're just gonna roll with it, right? That is an example of comeback rate, of disarming the moment as quickly as possible and moving on. In other context, I'm able to use that, the brilliance of writing on this topic, yes, and every time I flop, 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, you know, 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's, 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 gonna be like, oh, I wish I could pull that back, but now you gotta 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.

12:12Whereas if you call it out, it's gone. It's 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. It's 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've had to have heard some crazy stuff and you're studying and becoming 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 off site. She had to give a presentation. She's involved in public affairs. And so she, her title slide, since something public affairs in giant letters,

13:13biggest letters, because it's a title slide. The L never made it onto her title slide. So she's talking for about five minutes before she switches the slide in giant letters with a video camera, you know, iMac, close up, says pubic affairs on the back. And she, you know, people were snickering. And here she was, one of my thing is my fly down. But she realized, and here's the greatest thing. When you talk about comeback rate, obviously after that moment, 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,

14:15obviously tosen, it creates dopamine, it creates instant bonding, those prosocial 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, 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 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

15:17that 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 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's 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 gonna ask you, before you even brought that up, I'm like, how do you incorporate AI into this? Tell us how you do that. What do you prompted a certain way? Or how do you, how do you have a sparring match about awkwardness with chat GPT or GROC or whatever? Sure, okay. So I actually have a shameless fun.

16:17I 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. In 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, so there's not a spilling error to be found. 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, a 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 this presentation that we're gonna deliver here, 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.

17:20AI will give you three examples that fit all of those cooperative grade. 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 in sales, I think it's pretty old wisdom, get ready to stay ready. Don't go in there and wing it. Preparation 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.

18:22This is great. And I mean, think of how much money you're saving paying a business coach or something like that if you're talking to a GPT. I don't know. 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 used to ask the beginning, how did you become the awkward news girl? Let me get you one. Is a kid sent 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. And 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. 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,

19:25for 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 love 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 yourselves, for you to try to do things that 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.

20:25Henna's got some great information here. Also, you can check out Henna at prioritygroup.com. That's PRYORITYgroup.com. Henna, 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, and kind of those awkward moments. And actually had 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 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. Henna, how do you start your day with a win?

21:29Okay, well, I first always snuggle my puppy, but I don't think that's as helpful. So, actually, I agree. Here's the one that's related to my work. 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 really go, that's creepy, it's weird. I don't know how people are gonna react, but I make a point, at least a few times a 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, love 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. I 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.

22:30This 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 Hannah has written. Make sure you check out Hannah online, also on the social. She has a lot of great information out there, also on a lot of different podcasts. Hannah, 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.