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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 Intro
01:27 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.com
https://www.linkedin.com/in/hennapryor/
https://www.instagram.com/hennapryor/
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Biggest 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.
Awkward, 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.
And 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
of 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,
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 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.
Now, 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
is 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.
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 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.
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 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
or 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,
but 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,
but 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.
Whereas 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,
biggest 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,
obviously 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
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 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.
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.
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.
AI 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.
This 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,
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 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.
Henna'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?
Okay, 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.
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 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.
Start With A Win
