DGTL Voices with Ed Marx - Embracing Awkwardness (ft Henna Pryor)

Episode Date: June 18, 2025

On this episode of DGTL Voices, Ed interviews Henna Pryor, a workplace performance expert and author. They discuss Henna's journey from being the first-born child of immigrant parents to becoming a successful entrepreneur and keynote speaker. Henna shares her insights on coaching, the importance of influence in leadership, and the art of speaking. She emphasizes the need for self-awareness, the balance between generosity and boundaries, and the significance of recharging. The conversation concludes with a call to embrace the awkwardness that comes with leadership in a rapidly changing world.

Thanks for tuning to Digital Voices podcast, where we chat digital transformation, challenges and opportunities across healthcare and life sciences. And now, your host, Ed Marks. Hey, it's Ed. Welcome to another edition of Digital Voices. And I have a great guest with us again this week. Hena Pryor, Hannah, welcome to Digital Voices. Thank you for having me. Excited to be here.

I'm super excited because we first met at Hymns 25. at the executive summit, I was fortunate to be the MC, and you were a keynote of ours, and you just had the audience, like, totally engaged, and I was listening, so I snuck out from the green room and went out front to see a little bit about what's going down. And it was so fascinating. I thought to myself, I have to have you as a guest. So, again, thanks for being my guest. But Hennett, the most important question we ask on digital voices is what songs are on your playlist? What kind of music do you like? to listen to you. I like to listen to everything. I'm a big music person. The thing that you will find me listening to most consistently is 90s and early 2000s hip hop. That is like my comfort genre.

But generally speaking, I have very diverse musical taste. So Broadway musicals, hard rock, alternative, the new stuff. I have teenagers, so the new stuff is in our house. But if you want me to be in a good mood instantly, throw on some 90s and 2000s hip hop and I'll be good. All right. Yeah, love that. What about life message or mantra? Are there words that sort of guide you how you live? Yeah, I think it's honestly a phrase that is in my book, which is do it awkward, but do it anyway. The world is swirling far too quickly for any of us to aim for grace, precision, perfection. And I think the more comfortable we can get with our personal levels of awkwardness,

especially amidst uncertainty challenge and change, the better off we'll all be. Yeah, and I jumped right to it. I love that, by the way. I jumped right in, but you are also a workplace performance expert. You're a global keynote speaker, which is how we met already. We talked about that. But yeah, you're also an author, executive coach. List goes on and on. So tell us a little bit about who you are. And we'll start unpacking that a little bit. But what's your story? Tell us about your life growing up. Yeah. So first born of immigrant parents. My dad's from India. My mom's from Pakistan. And I was the first one to be born here in the United States. I will say that that really did inform a lot of my

early decisions. I very much wanted to make my parents proud. They were immigrants to the U.S. They worked very hard to have a good life for my sister and I here. And so my first career out of college was big for public accounting. I worked for Ernst & Young. And that was a very safe, stable, reputable job. I was good at it. I did not enjoy it, not one bit. So I was an audit for about two and a half three years until I realized this was just not the job for me. I needed to work more with people in a job that allowed me to do more talking. And so I made pivot number one, which was to executive search and staffing. So I worked for a $2 billion publicly traded search and staffing firm for 14 years where I became a leader and director in my Philadelphia region.

And that job was amazing. It was really, really good to me. But after about 14 years of doing that, I sort of hit this crossroads of I really believe that I can offer more to leaders. to professionals, to ambitious professionals like myself, than what I'm able to do within the confines of a staffing and search career. And so after about two years of a voice, kind of nagging me to play a bigger game, I finally listened and I became an entrepreneur in late 2019, 2020, 2020. Very cool. And you formed the priority group based off your name, a playoff in the game, and got into coaching.

Yeah. So tell us all about that. Yeah. So first of all, I never share this story much, but I feel like I want to tell you that priority group. It was a really fun besides it being, it's PRY-O-R-I-T-Y. So my last name is prior. But something interesting I learned about that word is that the word priority was never meant to be plural. So by definition, you can only have one priority. And somehow in the United States, we're always talking about our priorities. It's actually not the correct use of the term. And I just think it's such an interesting angle on this problem that we as ambitious,

professionals and leaders have, which is we're constantly trying to juggle our priorities. We were really never as humans meant to live in an era where we're doing everything at once with equal levels of urgency. And that's what it feels like all the time. And so there were just all these little problems or lacks of strategy and tool that I identified in my staffing career when working with leaders. And I thought, okay, the problem isn't more tools and more action. I have a bias for action. I think a lot of the people who work with me do as well, there's some blocks. There's obstacles underlying it. And so my angle as a coach and frankly as a keynote speaker became very centered on not what are we doing or what can we be doing more of, but what are we not doing?

Where are there, you know, where is there mud in the gears? And how can we start to address that? So that's, that's been a lot of fun to explore. Yeah, I love that. Can you share like one or two examples for a client, probably can't name the client, but in terms of, you know, your typical client, like success stories. Yeah. I think so again, a lot of my clients are attracted to me because they share a bit of my wiring, which is bias for action. They are action takers.

They are fast movers. They are fast thinkers. They are fast processors, right? We are not doing anything at a turtle's pace. We're just go, go, go. And honestly, we live in a system that rewards that. The person that is first to action, that is first to decision. We live in a system that generally admires those types of people.

but there is a shadow side to constantly being in action and not spending more time in building self-awareness, deep understanding of what triggers us, deep understanding of what it takes for someone to communicate with us in a way that it's received and for us to do the same with other people. And so I think a lot of the people who I work with are finding themselves at some sort of crossroads of all these things I've done that have made me successful to hear are no longer working as well as they used to, Hannah. Did something break? Like there's something wrong with the machine. And I'm like, there's nothing wrong with the machine. What got you here, won't get you there, as Marshall Goldsmith said. And now the times have changed. You have changed. The people you report to

have changed. Things have changed. And now we need to make adjustments. So we start to do some, frankly, unsticking. What is now getting in the way? What do we not telling ourselves? What do we not know? And how do we start to ask the right questions that help us unlock that next level of performance. Yeah, as you described that, that sounds like it would fit me and fit everyone. Yeah, everyone I've ever noticed high performing, you know. What is one thing that you might be able to share that most execs have not mastered, and you alluded to them already, I believe, should work on. Okay, so I'm not going to say deep self-awareness, because I think that's baked into what we just talked about. What I would say is most executives have not yet mastered

the correct techniques that create modern influence. So here's what I mean by that. The old paradigm of influence. So if you're an executive, you're trying to influence your teams, you're trying to influence stakeholders, you're trying to influence your clients, you know, pick your poison of who you are trying to influence in any given moment. Most people are still operating by the old playbook. Listen, nothing wrong with the Robert Cheldini's of the world.

That's all valid and it still stands. But it's half the equation. So the old equation was if they're not saying yes, we need more case studies, testimony, testimonial, data, proof points. We need to create more reciprocity. We need to create more, you know, all of that is still correct, but it's only half of the equation. So one of the first questions I will often ask in a keynote is, especially my influence keynote, is, you know, raise your hands. If you're the exact same person, you were five plus years ago. And of course, no one raises their hand. And then I say, raise your hand if you're not. And then, of course, everyone raises their hand. Well, this little thing that happened, and if I can be a little crass, one of the byproducts of that huge. thing that happened to us globally was that our tolerance for BS went way down. Yeah. And our ability to sniff out BS and other people, this person doesn't have my best interest at heart.

They don't get me. They don't understand me. That's gone way up. So we are living through something that is often referred to as kind of a modern believability crisis or a modern trust crisis. And our tolerance for this stuff is way down. So when it comes to influence, one thing that we're getting wrong is when somebody's not doing what we want them to do or they're not buying in or they're not engaging.

Actually, one of the worst things we can do is give them more social proof, more case studies, another demo. That's not what it's about. Today, influence is about identifying and having an action plan for those frictions, for those headwinds that are standing in the way. And most executives still don't even know what they are. So we spend a lot of time working on identification. We have to lower the wall before we're going to get anything through. And so that's been a big shift. Yeah, I love that. That's great. Let's talk about speaking now, because that's another thing that executives need to master. And as we know, there's different levels of that mastery. But first, how did you pivot to speaking? So you started the prior group and doing the coaching, but also you have

this passion for speaking. I never set out to become a speaker. And I think a lot of speakers will tell you the same thing. As kids, that was never on the list of options of professions. And when I left my staff in search career, a bunch of my leaders had said, gosh, Hanna, you're our search partner, but we really

should pay you for all the executive coaching you do for us. And I was like, I'm sorry, the what? To say more? So actually started, I got my certification

down at American University in D.C. I got my start doing executive coaching. And honestly, the speaking happened very organically. I was working one-on-one with leaders, with clients

who would say, this was really powerful for me. Can you come do this with my group? Can you come do this with my larger team? Can you come to my company retreat? And honestly, very slowly and steadily, the room got larger and larger.

And the first few times I got to share a message or an idea from the stage, it was very clear to me that that was where I lit up. That was my zone of genius. And it's funny, I was the last to know. My mom and my sister and my dad are like, you were the MC of your prom fashion show in high school. You were the commencement speaker at your grad school graduation. You've always loved being on a stage. And I'm like, okay, yeah, I never thought of it. But I think there was always something in there that made me very comfortable in that space.

So I'm just grateful that I get to do it. Yeah. And so you've done quite a bit your very tenured, very experienced speaker. Tell us about one gig in particular that was just fun. Maybe it was the location or the topic. Yeah. Yeah. Honestly, the most fun gigs are when the audience is open and bought in.

Right. So the tough ones can sometimes be when the audience. is skeptical or, you know, they feel like they've heard, you know, speakers, listen, there's a lot of the same stuff. So they feel like they've heard it before. There's a level of skepticism. I feel like I'm going to sound like such a suck up. But, you know, Hymns was a really fun one for me because I only had 30 minutes. So it was, you know, I'd rather have 60. To be honest, for speakers, it's harder to have less time. We have so much we want to share and so much to say. And I know that healthcare and health care information management in particular, these are challenged industries right now.

And that talk was about mindset. Now, if I'm a leader in that room, I'm going to be like, oh, good grief. Like, give me something that's going to solve my problem today. And I think one of the fun things was getting to start that conversation with, listen, I was a skeptic of mindset. When people said, hey, we're going to do mindset trading, I would have been like, I got things to do today. I got emails to answer things. You know, my clients need me. I would have not been the first one to say that sounds valuable.

And so, you know, I kind of took the wall down, right? Is this going to be something I need? Is this woo-woo? And for them to instantly open and become open to the idea, and I could see them nodding and engaging and like, yes, we need this. This is exactly like, how do we make this idea of mindset, which is very airy-fairy, actionable? And to see that mindset shift happen for them in real time, anytime, honestly, any audience where I get to watch that mindset shift cross their faces in real time, that to me is always

the most fun because that feels like real impact. I'm not just talking at them. Their worldview has changed when they left that room. And that's really satisfying as a speaker. Yeah. Yeah, there was a lot of, I'll be your witness. You know, there was a lot of us. I loved it.

Thank you. So what about one or two pieces of advice or hacks for executives that not that they're aspiring to be speakers, but by nature of the role, they have to speak. So there's probably one or two things that you might recommend. Yes. Just simple two things that I would recommend are no matter how long your talk is, whether you're talking at a group for five minutes or you're delivering a 60 minute presentation, I would encourage you to think of the framework in your mind as a why, what, now, how. So why are we talking about this? Don't assume, because this is important to you, that the people you're talking to understand why this matters

to them, especially if they're different levels. So, you know, in the mindset chat, I might say something like, you know, whether you're a leader or leading teams who are really struggling or your boots on the ground and really trying to figure out, how does this day feel less hard? How do I find myself less frustrated, right? Make sure every single person in the room understands why are we talking about this. A little bit of the, you know, what now? What are we doing? What's current state? And then, of course, the how. But when you think about it through that structure, it's going to pretty much ensure that you hit the three main points, but a lot of people skip over the why. They get right to the what now, how, and they assume people, they know why this is important. Well, maybe not the way you do,

right? So make sure you hit all that. The second piece of advice I would give is today more than ever in the era of of AI and robots, please don't sleep on the power of your physicality. So physicality can be, if you're in person with people, it can be the way you intentionally use your hands. Here's an example. You know, Ed, you and I currently are on a Zoom call. And I might say, you know what, point number one is this. Point number two is this.

And number three is this. Just by virtue of me using my hands, and again, if someone's listening and they can't see me, I'm putting up fingers. One, two, three. Just by virtue of using my hands, I'm reinforcing the message. in a way that comes across as more, you know, executive presence laden, as a little bit more impactful. I can also use my body as a timeline, right? For American folks, the past, if I'm looking at them in an audience, the past is my right,

their left. The future is my left, their right? There's ways that you can use physicality. And if you're virtual, use your voice. Use contrast. I'm a fast talker. I'm a fast speaker. And I'm also pretty loud in the way that I speak.

And Ed, if I wanted to get your attention right now, you know what I might do? I might really take it down and start talking really softly because all of a sudden you're like leaning in. Yeah, leaning in. Right. And it's not because soft is better than loud or loud is better than soft. It's because I put in some contrast. So if you're naturally a soft spoken speaker, experiment with some pacing and dialing up the volume from time to time.

If you're naturally more gregarious, experiment with longer pauses. slowing down. But those two things can really improve the impact of anything that is happening with speaking. Yeah. That's gold right there. So thank you for dropping that on over. Yeah. Let's shift a little bit to leadership because obviously through the speaking, all the

engagements, obviously your earlier part of your career and search and things, you've got a lot going on in terms of leadership. Was there something early in your life, do you think, that prepared you to become a leader that you are today? It's funny. My parents were really wonderful about home moves. And so we've got a lot of them. I'm currently having them converted to digital.

But I have one younger sister. She's a little more than four years younger than me. And I think there's a little bit of it. And I'm sure anybody with kids can laugh that that's in the blood, right? Like my sister's trying to sing on the microphone. I'm like, move over, son. I have something to say. I think there was a little bit of that like bossiness.

But more than that, I really liked it when something I did made someone's life easier or better or more efficient or more productive. I think it's really amazing that humans have this ability to impact other people in a way that truly transforms how they walk through the world. And so for me, leadership has never been about, you know, how many direct reports do I have? In fact, in my last job that I had before becoming a speaker, I worked again for an organization, publicly traded company. And they had numerous times asked me to move into formal leadership roles. So I was in sales. I was commissions. And they said, will you be, you know, the director of the team?

which was a true formal leadership role with direct reports. And over and over I said no. Yeah. Over and over I said no. I said, I would like to be a leader on my terms, meaning I would like to be, sorry about the dog, I would like to be able to coach them from the field, right? I'm in the job and I want to be able to teach them the way that feels right to me. I don't want to be one of the people that's just, you know, checking the boxes or doing the metrics.

Nothing against that. But I think finding this style of leadership that best suits your strengths and personality has been, to me, one of the biggest gifts of understanding what kind of leader I wanted to be. And there was a certain kind that suited me and a certain kind that didn't. Makes total sense. What one thing that you learn the hard way, so, you know, we'll go through peaks and valleys. But there's always a learning opportunity, right? So what's one thing you learned sort of the hard way?

Can I tell you something I'm currently learning the hard way rather than, I haven't solved for it, but I think other leaders will relate to this. Something that I have struggled with and, to be honest, continue to struggle with, to some degree in different parts of my life are boundaries. So one of the ones that I'm currently struggling with is as a speaker, as an author, I have an ink column. I have a LinkedIn learning courses. You know, I've got my hands in a lot of things. And I'm very grateful for all of it. And because of that, I have a lot of people who come into my DMs and into my email who say, can I pick your ring? Because what has happened for me by a timeline looks like it happened very quickly. You know, within four or five years, a lot has happened. So they see it as Hena has some blueprint, Hannah has some formula,

Hannah has a lot of hard work, a lot of hard work. But they see that and they want access to my time. My internal struggle has always been, I am someone who deeply identifies as being generous. You know, people have been good to me. They've been generous with me as I've come up as a speaker as a writer. They've given me advice. They've offered to have time with me on the phone.

And I also identify as someone who it's really important to save time for her family and to be present to my kids and to have time with my friends. And so this tension between my identity of generosity and my identity of protecting my family and friendship boundaries has constantly bumped up against one another. And so what I'm working on right now is I've developed some mechanisms. I have an FAQ library for frequently asked questions. I have a calendar link that's called my brain pick link. Once it's full, it's full.

and enforcing those boundaries over and over and over will continue to be the lesson I learn over and over again and will be the one I think I will always find myself bumping up against but that's the work. That's my leadership edge and I will continue to explore ways to continue to grow that. Yeah, thanks for sharing. I appreciate that. And you also had a solution or at least a solution to trying to make it all work.

It's helping. Yeah, along those same lines, what do you do? Because as a leader, yeah, you're a super busy person and you have family and friends, what do you do to sort of recharge, right? Because you have to go on stage and be fresh. But so certainly there's some things that you probably do to... I am an extrovert, so I am energized by being around other people, but that too runs out. Ed, if I'm being very honest, it's been a long week and I have not had a lot of sleep. I was traveling earlier in the week. This is, for me, it's, we're recording this in the afternoon

on a Friday. I'm about at the end of my energy rope. I'm giving you what last bit remains in the tank. And I am someone who has had to do a lot of work around recognizing that rest is valuable. You know, I'm from an immigrant family. Achievement orientation is very deep in my blood. And so for a long time, I held some very wrong narratives. I wouldn't even say my parents ever said this to me, but some wrong narratives around rest being like lazy or not doing enough. And so today I am very, very good about when I need to recharge, just slow time.

It doesn't have to be idle time, but slow time. So for me, recharging looks like, you know, past 10 I would have been like, I'm going to take a walk. But I'll be honest, Ed, it still would have been a speedwalk because then I could have gotten my fitness in at the same time. Right. Now it's a slow, no phone meandering walk. And that has been a huge shift. And it recharges my batteries in ways that I don't even think I knew that I needed for a long time. Yeah.

That's all. I'm laughing. I'm smiling for those just listening because everything he's shared resonates deeply. Yeah. I'm wired very similarly. Wow, we covered a lot of ground in a short amount of time, given our personalities, not surprising. We're very efficient, Ed. We're very efficient. But do it awkward, dude anyways.

Brilliant. Love that. It was great to hear about you growing up and being first generation and then your whole career journey from accounting and recognizing. and recognizing what you did like and making it change, right? People get stuck. They would still be an accountant today. I think 90% of people.

But you took action, you took change, you created these companies, you created your, recreated yourself multiple times. And then you gave us some great hacks, golden nuggets on speaking and good coaching type things to improve ourselves as executives.

Is there anything I missed or anything you want to double down on, I'll give you the last word. Yeah, as we're going into re-release of, my book called Good Awkward. That's a word that a lot of leaders don't always jump to. Some do, but they think, oh, that was earlier in my career. You know, I'm a leader now. I really want to encourage everyone who is listening to embrace the inevitable awkwardness that the next few years are going

to bring. We are in a season of immense technological change. We've got five generations in the workforce. Six, if you include the upcoming summer intern class, right? We've got political change. We've got regulatory change. If you don't feel awkward right now about things as a leader, you are not awake. You are not breathing. So please prepare for that emotion and embrace it. It is not something we can outrun. It does not mean that you are no better at your job. But I think the more we can all lean into that emotion and learn how to work with it rather than fighting it, the better off will be. Hannah, brilliantly shared. And thank you again for being guest on digital voices. Thank you for having me.

Thank you for listening to Digital Voices podcast with Edmarts. If you enjoyed this episode, subscribe on your preferred streaming service and leave a rating and review. And most importantly, thanks again for listening.