Kristen Sharkey from Emboldify | Using Improv To Build Resilient and Authentic Leaders

Christine: [00:00:00] Welcome back to another episode of the HR Scoop. I’m Christine Muldoon and I’ll be your host today, and I am really excited about today’s guest. She brings a unique and fascinating background to the table, one that challenges the way we might typically think about leadership. We’re going to unpack all of that shortly, but first, I’m thrilled to welcome Kristin Brun Sharkey, the founder and executive coach of Emboldify.

Bolded delivers coaching and training to help leaders enhance their leadership skills and thrive in rapidly changing times. So Kristen, welcome to the show. Thank you, Christine.

Kristen: I’m excited to be here.

Christine: Me too. Um, I did a little background research and I read that you spent the first 15 years of your career leading teams in ad tech and marketing.

Then you stepped into a people management role [00:01:00] pretty early on, and it was during that time that you discovered that mentoring and coaching your team was the most fulfilling part of your job, which I think right from there, it’s kind of unique because it’s not something you may commonly hear from leaders.

That’s a hard part of the job. But fast forward to today, and not only are you an executive coach. But you and your husband also co-host a podcast called Love and Leadership, where you proudly call yourselves the leadership nerves, which I absolutely love. We’ll have to like find out how you got to that name as well.

But I also wanted to say that there’s a facet of your story that’s particularly unique, and I think it might take some of our listeners by surprise. You’re not just a traditional executive coach. You’ve taken a very different path to get there, and I think you’d even said it was a real game changer for you.

So I’m just [00:02:00] gonna hand it over to you first to share what that was and how it reshaped your path.

Kristen: For sure. So the kind of unique component of the, the coaching and facilitation work that I do is bringing in aspects from improv theater and I, I started doing improv very randomly, just like on a whim, maybe I think about eight and a half years ago, and just fell in love with it.

And it took a little bit before I realized that it wasn’t just like really fun and it didn’t just have a great community. It was actually having a huge impact on how I showed up at work on like my creativity, my confidence, my collaboration. So that was kind of the first indicator that, okay, there might be something here.

And I, I had already been kind of interested [00:03:00] in doing coaching and facilitation and having my own business. Um, actually my father was a, was a small business coach and facilitator, so I kinda had that exposure. But the improv piece was really like the missing puzzle piece for me and, and pulling it all together.

And I absolutely love working with leaders, um, all sorts of different levels. To help them grow their presence and apply so many of these different aspects from from improv for their teams.

Christine: I bet that’s not what I would consider a standard path for becoming an coach. And I’m also guessing that not many listeners would’ve expected you to say improv really influenced your career.

And, uh, helped your growth and focus in the leadership coaching area, but I think it’s really unique. It’s kind of interesting. We’ll kind of drill down on that a little bit more. Um, just kind of giving some [00:04:00] background, you know, as you think about leadership at WebMD Health Services. Our mission is to empower wellbeing in everyone.

And a big part of that for organizations, our best practices is leadership. Support leaders have to model the behaviors that they want from their people. So from a wellbeing perspective, that’s like if you want people to focus on their wellbeing, you need to focus on your wellbeing too. Whether that’s physical, mental, emotional, social.

So in order for. From our perspective wellbeing, to be really part of a company, it has to reflect leaders believing in themselves, prioritizing their own wellbeing, and really being self-aware. So kind of making this parallel with that in mind, um, how do you see these improv skills, like let’s just say being present or normalizing failure.

Actually helping [00:05:00] HR leaders address things like employee burnout or mental health challenges. And I bring these two up because they’re two big, pretty, uh, pretty big wellness priorities that are present in our market today.

Kristen: Absolutely. Yeah, it really does make a a difference because I think a lot of times when there’s, when there’s burnout at play and people are overworked, there’s a, a disconnection there, there is a focus on constantly performing and, and constantly being perfect in many cases, that that helps drive that.

So what I, I really love about improv for that is the. The first piece you mentioned with being present like that is something that is not, does not come naturally to most of us, especially not in today’s world where we have a billion distractions happening all the time. But it’s a kind of skills where if you train [00:06:00] them, it has so many benefits.

I mean, mindfulness in itself has so many well documented, researched benefits to it. Um, but improv is like another way at. Like that, achieving that presence, um, it really forces you to be in the moment, which is really powerful. And then I think the other piece of it that you’re doing, like improv exercises, it also really trains you to see mistakes differently until to actually like, accept and even welcome failure.

Which takes a lot of the pressure off, like when, when you can get used to doing this and when you can create a, as a leader, you can create a culture where failure is destigmatized and people feel safe. You really like that helps contribute to this sense of psychological safety within the team as well.

So I think all of those help. [00:07:00] Contribute to the, the wellbeing of a team. Uh, but as you said, it’s really important that the leader models this stuff first as well. I

Christine: think you hit on some really big things that stand out to me as a leader, and maybe generalizing this a little bit, but you said like leaders feel like they have to be constantly performing, always on, um.

We’re probably less likely right, to welcome failure. Like we can’t fail, we have to be perfect. We have to, you know, move the business ahead. So building in, I guess, improv to help us, uh, think about how to respond and be in the moment really changes that dynamic and it changes that mindset, which very similar, like wellbeing.

It’s like you have to. Um, adopt the these behaviors and demonstrate these behaviors in order for your employees to, or your team members to feel like, [00:08:00] okay, this is okay. Like, I’m not gonna get in trouble. Or sometimes you just can’t be on. Sometimes you do have to take that break

Kristen: For sure.

Christine: I’m gonna be honest though, I mean, the idea of improv is a little bit intimidating to me.

Um, I don’t really see myself, and this is how I interpret improv, but I don’t really see myself as an on the fly kind of person. Um, which is how, again, I view improv. I’m more of what I consider to be a planner and a prepper. I need to know everything that I’m doing. I actually needed to know a lot about you before I spoke with you on this podcast.

Like I am a planner. And to me, improv just feels very, um, nerve wracking to me. Like, I don’t know what I’m gonna say. I don’t know. I don’t wanna think on the spot. So maybe there’s some HR leaders listening right now that maybe feel the same as me, or they’re like, oh, this is interesting. I really would love to give this a try with my team.[00:09:00]

So do you think you could give us like one quick, maybe low stakes way that they could dip their toes into using improv principles, maybe in a meeting or a conversation? Maybe it’s based on welcoming failure or addressing that, you know, elephant in the room. Um, but what could that look like for someone?

Kristen: For sure. Um, and by the way, I just want to validate all of the, the things you said about like fears around improv. These are very common and I, I am also, my default state is very much a perfectionistic planner. So improv has helped me in many ways with, with calming that down. Uh, but, but yeah, these are completely, these are very common.

Reactions to it. So my, my favorite way to start with it is just with a, giving a series of simple exercises that leaders can do with their [00:10:00] teams. And it’s a really good way to. Demonstrate that there’s also exercises you can do on your own without a team if you wanna just build up some of these skills.

Um, but I, I have several. I use, I actually can share, I have a PDF of eight, like, uh, eight exercises that are, and it’s designed so that you can lead them with your own team. So I’m happy to share the link to that for the show notes. But, uh, one of, one example of those one I did. Just the, the other week, and it’s always a lot of fun, is called remember the time.

So this is a, this is a group exercise, so like everybody stands in a circle. And you go around the circle and one person starts by just by putting out like a piece of a fictional shared memory. So this can be something like, remember the time we all went to the beach together? Or remember the time [00:11:00] that we had a picnic.

Like whatever it is, it can be whenever it inspires them and not overthinking it. Then the next person adds something to that. They add another detail. So it’s like, oh yeah, and then we built a huge sandcastle and then the next person adds another detail. So you’re, you’re creating this shared reality together and it’s, it’s so good for team bonding.

It really, um, it demonstrates one of the key principles of improv, which is Yes. And so, which is this idea that you are taking the contribution that. Per a person put forth and you’re agreeing, you’re like validating it. You are, you’re saying yes to it, and then you’re adding your own contribution to it.

So it’s really the core of what improv is. And I, yeah, I love exercises like this for, for many, many purposes, but especially for kind of creating that shared experience with the team. It can be really fun and get really funny. [00:12:00]

Christine: I can imagine it, it sort of reminds me of like when you were a child and maybe were on a long car ride, let’s say, and you, you build those stories as well.

This would seem like you’re doing it with. Peers. Right? And so you’re actually add creating a story together, but also maybe learning about individuals as well based on what they’re thinking about they, what they’re gonna add to the story that maybe is a reflection of their personality or what they would do if they were on the beach or.

Kristen: Yeah, for sure. It’s pulling in everybody’s kinda unique ideas.

Christine: So if this was, um, a leader, you know, doing this exercise, but there was some, something went wrong, like there was some level of failure that, you know, let’s say it’s me and my team, [00:13:00] how do I leverage this improv at the same time like that? Yes.

And to. To incorporate that failure, like it’s okay. Is that like a yes and scenario as well?

Kristen: Yeah, it is. And you know, it’s funny, and the, the theater I did my, my classes through the level one classes there, you actually celebrate every mistake. So if somebody makes a mistake during an exercise, you actually like applaud.

Like cheer is a group, and it was very jarring to me at first as a recovering perfectionist. But what’s really cool about it is that it, it normalizes it. And over time you kind of learn to realize that mistakes and improv are actually gifts. Like that’s where some of the best scene work comes from, is by acknowledging the mistakes that happen.

So, and similarly when when you do an exercise like the, like this, the biggest thing is to just keep going. So it’s, you know, acknowledge a [00:14:00] mistake, celebrate it, and then just keep, keep moving. Um, what we try to avoid is Pete deal getting too in their head, because we all, we all have this like inner judge or inner critic, depending what you know it as, that loves to second guess the things that we say in our initial reactions.

And, um, it wants to overthink everything so. Uh, you, what you wanna do is ideally take action before that kicks in. And it’s something that could be challenging at first, but it, it really is like a muscle where the more you do it, the easier it gets.

Christine: Okay. So you just sort of a ga some insight into me because I overthink, I second guess.

And those are things that pretty much keep me up at night. So I need to learn to let those go. Maybe pro practice some Yes. And, uh, technique, uh, with my family as well. Um, so I wanna [00:15:00] shift a little bit and talk about your company in Boldy, which is all about obviously helping leaders grow in their careers, make better decisions, and of course engage their teams.

And, you know, as we’ve been talking about using some principles of, um, improv as part of, of how you do this coaching. So can you share with us a little bit about how your coaching and workshops work and how you bring all this to life? Maybe what, what it looks like for a leader really in action, what they would, uh, expect from working with in bold.

Kristen: Yeah, totally. And it looks a little bit different depending on, you know, what the, the objectives and structure of the engagement is. But, um, I have a, a model I created called the, the ad-lib leader model that’s kind of at the core of everything I do. Um, and it’s, it’s basically [00:16:00] these, these five central.

Components of, of improv. So you have presence at the middle and then you, you have resilience, creativity, supportiveness and authenticity are the other pieces. So all of the work that I do kind of comes back to this model in some way. So with coaching, a lot of times we’re working on specific aspects of it, like working on like leadership presence is a really common one actually in both.

Like one-on-one coaching and when I do like workshops and facilitation, um, but with kind of a little bit of an improv spin on it. So that’s like a really common one. But when we’re talking about like leadership presence, it’s like the being present is the center of it. But then also talking about like things like authenticity, like how do you come across as authentic?

How do you connect? Other people. So these are all skills that can be learned both within [00:17:00] one-on-one coaching and within like a group environment. And then for the workshops, I have like a whole set of, of topics that, and I do custom ones as well that that pull in different aspects of this. So all was kind of like an improv twist.

So like for example, doing a workshop on creating a culture of innovation. Is a big one. Or decision making tactics using like improv principles or leadership presences. Again, also really common, so there’s a a lot of different topics where this can relate just depending on what the objectives are of the organization.

Christine: I think there’s so much alignment to your ad-lib model and the five central components. To being a leader and adopting or trying to create a culture of wellbeing at the same [00:18:00] time. Not that we have those, we’ve laid those five central components out. Exactly. But you know, we do talk about, uh, as leaders, you wanna be authentic, um, you wanna be present, show your resilience, because that’s how employees feel like.

They’re being cared for within the organization or the organization cares for them, and that it’s okay to have to one, focus on your wellbeing and two have obstacles along the way. Like not everyone is going to be able to get off the couch and run a 5K, and you’ll have ups and downs. But you’re training towards that, or, you know, talking with a health coach and being okay with recognizing, um, you know, what your goals are for wellbeing.

And not everyone wants to train for a marathon. Some people, you [00:19:00] know, just wanna focus on feeling good about themselves or being able to play with their kids, get down on the floor, play with their kids or grandkids. So there’s some. Some similarities on these components that are important for leaders to reflect in creating a culture of wellbeing as well.

Kristen: Absolutely. It’s like a very individualized, I I can affirm that I will never be running a marathon in my lifetime. So I Quin too, and I’m okay with that. I’m totally okay with it. It’s, you know, that that shift has sailed and I never wanted to be on it. So,

Christine: so talking about, um. Bold. And some of the clients that you work with, you’ve worked with everyone from like a startup to Fortune 100 companies.

Um, do you, is there, are there major [00:20:00] differences that you’ve noticed in how leaders coming from organizations of those different sizes. Um, like ultimately approach team engagement. And how would you then tailor your coaching to meet those unique challenges? You said, you know, it’s very personal, not everyone’s the same.

So can you talk a little bit about that?

Kristen: Yeah, for sure. There are definitely differences. Um, particularly talking about like a small early stage startup versus like a large company. There are many differences, but the same, the same core principles apply, right? Like the skills of listening, adapting in the moment, co-creation with your team, like all of that still applies, but, um, what we emphasize or focus on.

Can be different. So a lot of times with a, a startup there is. Often, depending on what stage they’re in, there is, can be a lot of energy already. [00:21:00] Um, but there can also be a lot of burnout if there’s been people working very long hours for a long period of time. That’s also, I. Can be a big factor and or wearing multiple hats because they’re a startup, they can’t have a huge org structure.

Yep. Yeah. I wor I worked for a 10 person startup once upon a time, so I, I’ve never wor worked more in my life, I think including with starting my own business. Um, so, so given that, I think there, that, that can really help drive the, the focus of. Of what we’re looking at and some of those elements of from improv that really help people with dealing with like fatigue and overwhelm and burnout and how to prioritize when you have 8,000 things on your plate.

Um, and then when we, when we start talking about like big companies, a lot of times there is you kind of. You have companies who are like, oh, we value innovation, [00:22:00] but it’s not actually happening. Um, they’re really, they have a lot of this. Like, that’s, this is how we’ve always done it. Iis I like to, I like to say, um, where anytime that phrase is, is coming out in any variation, it’s an indicator of like, hmm, something.

There’s a flag here. Um, so a lot of times it’s working with them to like create a, like how do you build innovation into your culture? And, um, and in both of these it can, there, there can be a lot of work with like, with helping develop leaders, especially there’s more junior leaders who haven’t had a lot of mentorship, which is especially common in the startups, that there can be a lot of that kind of core.

Like leadership presence, how do you manage people, kind of, kind of stuff. But, um, I think with enterprise, it’s, it’s more likely to be focused on the, the innovation piece and as well as a lot of these other core topics that we talk about.

Christine: I would expect maybe that, uh, [00:23:00] you know, building, you know, a, a leader might say.

Maybe in more of a smaller startup, but, but maybe in a Fortune 100 company too, that, hey, we wanna have, we have an innovation of culture. And as a leader they say that, but what does that actually mean? And you are coming in to some degree to make sure that leaders like what are the elements that make your culture that way?

How are you lead leading to support? That environment, that culture that helps your teams fully believe it and feel like they can practice it in some way. Mm-hmm.

Kristen: For sure. Yeah. And because this is so common, like culture is not words on a wall, like culture is a, a combination of like norms, behaviors, and rituals that happen within the group.

And what, as, as a leader, what you do yourself is going to be a [00:24:00] huge determinant of what the, the culture of the team actually looks like. Not what. What words you’re coming up with that, or you’re saying inify your culture. So, um, so yeah, so it is, it is, there’s a whole process of like breaking it down into like what is, what does that actually mean?

Like how do you create a culture of innovation and how do like improv principles relate to that as well. Because a lot of the things we’re talking about are like, how do you use like yes and principles to. To effective brainstorming. Um, it’s so common that companies will step over the idea generation part I.

Which is needs to be separate from the analytical part of it. It’s like divergent versus convergent thinking. So a lot of times it’s like taking a step back with organizations and going, okay, like how can you integrate the more generative, divergent thinking into your organization?

Christine: Really [00:25:00] interesting. So if there are some differences based on company size.

Is there similarities or something that like all great leaders actually have in common, regardless of the company size?

Kristen: Hmm. That’s a good question. I think like emotion, I think emotional intelligence is going to be, I. Equality that’s broad enough to say that I, I, I personally think it’s very difficult to be a long-term effective leader in this current world without emotional intelligence.

Um, it doesn’t mean that you’re gonna be perfect on all aspects of it, but it’s, it’s so important for, for leadership. Um, so I think that a lot of that is a common thread and a lot of the work that I do comes back to. Emotional intelligence things we’re talking about, like being awareness of yourself and others, and authenticity, like these are all things that tie into [00:26:00] emotional intelligence.

Christine: Is emotional intelligence something that can be, um, improved, refined through coaching?

Kristen: Yes, absolutely. I, I, I very strongly feel that emotional intelligence is something that can be improved. Um, you do have to have the desire and motivation there, right? So I actually have, um, a certification with a company called Genos.

So it has a really great. Like 360 version of a like emotional intelligent intelligence assessment. So like sometimes it’s a matter of doing that assessment and that can be very eye opening to the leader and kind of help them really see like where I. If they have improvements to, to make with emotional intelligence.

But as long as that motivation is there, it is. It is all things that can be approved upon, like I integrating specific [00:27:00] behaviors and changing your thought processes. And if you’re willing to do the work and get feedback on it consistently and be a little bit humbled by it, it’s a hundred percent something you can improve.

Christine: Okay. I have to go back to something I said earlier that I wanted you to describe before I forget, which is that you and your husband call yourselves the leadership nerds. I can assume that’s because you both like focus on some level of leadership coaching, but how did you come up with that?

Kristen: Um, I think it’s, it’s funny, like I think we bonded on our first date on leadership development, which is inherently very nerdy.

Uh, but my, we come at it from different angles. My husband is in like the senior living hospitality industry, um, has that background. I come from more tech marketing and then obviously I, I focus on leadership development full-time now, but [00:28:00] we come from different perspectives on it, but like we both. Just love reading leadership books and that was something we bonded over very early.

So it’s just kind of naturally when, when the podcast started becoming this thing and the were all like our, one of our taglines ended up being that like we’re a couple of leaders or a couple of leadership nerd who also happen to be a couple.

Christine: Yes, I love it. That’s great marketing.

I love it. Um, I was going to say something as you were talking about that, it just escaped my mind, so that’s a bummer, but it will come back to me. Um, I wanted to kind of bring back another example, um, as we’re talking about this because we know that today, you know, if our audience had that’s listening in or our HR leaders, um, we respect and understand that they’re all juggling a lot.

Um, you know, organizations may say, you know, we’re still [00:29:00] virtual, or, no, we want everyone back in the office. Or maybe something in between where organizations are still very much a hybrid work model. So as, as HR leaders and other leaders are trying to really sort this out, but also focus in on their teams or people that they’re managing, how can they apply some of this?

Improv inspired, um, adapt adaptability essentially to really strike the balance between offering flexibility, but at the same time, it’s about keeping our people, our teams truly connected.

Kristen: Mm-hmm. Yeah, absolutely. Yeah, and I think this, this is a, a big challenge that so many companies have been going through for the last.

I mean, as five since the pandemic started. Right? We’ve been really figuring this out at a larger scale. Um, I think as far as like how the, the improv piece of this [00:30:00] comes in, I think the, the presence piece. If once you train that it. It becomes a little easier to pick up on things, especially over zoom, where it’s, it’s harder to read people and it’s harder to, to like kind of feel like the, the tension you might feel in like a room when people are all physically present.

So a, a lot of these skills, I think specifically help with that, with like being. Aware of what’s happening and be able to make a change, like the needing if needed to, to address something. Um, but I also really like having like team rituals and having like that, that really help with the connection piece.

So these are really great places to kind of insert like an improv game or. Non improv exercise, like whatever it is, there’s a lot of different things that you can do just to generate some laughter in like a, a moment of, of team connection before really getting [00:31:00] into business. So I’m, I’m a big fan of, of have adding those.

It’s just a couple of ideas.

Christine: No, that’s perfect. I know. You know, even I have a lot of team members that we’re, we’re pretty much a team that’s virtual and so we have tried to maintain, um, some of those rituals for sure across our team, um, and have tweaked along the way. I mean, it’s been several years since, you know, we all went.

Virtual and recognizing that, you know, you sometimes have to change elements to make it continually work as new team members come in or changes in your org structure or where people are located. So I think that’s super helpful. If everyone listening today is like, alright, Kristin m bought into this improv leadership coaching thing.

Um, is there like one tactic. Or exercise, simple exercise that listeners can try [00:32:00] out this week to see if they buy into what your strategy.

Kristen: Yeah, there’s, there’s a few to choose from. I mentioned a, a team exercise already. Um, but there are a lot of things that you can do just on your own as well to kind of help building some of these skills and also like kind of just increase your awareness of like, okay, where is my, my inner judge kicking in here?

So like one, like, just really simple exercise that works in many configurations, including by yourself is. You can just basically have a conversation with yourself, like two sides of a conversation, or you can do like a monologue, but where every sentence starts with where the first word of every sentence starts with a, the next letter of the alphabet.

So the, the first sentence would start with a word that starts with a, and then the next one would start with a. Word that starts with B and so forth, [00:33:00] and just trying to like train yourself to go as quickly as possible, like minimize the long pauses, don’t overthink it, and just keep moving forward. Like this is an amazing way where if you do this over time, it really trains your brain to.

Be able to act more instinctively and less getting stuck on that, that inner judge where you’re like, oh my gosh, is that sentence good enough? That doesn’t even make sense. Why would I say that out loud?

Christine: I love that, and that’s something I can do. And in fact, I’m going to do it after we get off this podcast today.

I love them. So every, so you’re gonna do a sentence and every sentence begins with the next letter. Of the alphabet. Mm-hmm. So you better know the alphabet. Let’s just start there

Kristen: and don’t over. Yes. But also like if you make mistakes, just keep going.

Christine: Keep going. All right. That’s fair enough. I can certainly handle that.

I might have to like write down what letter I just did on a piece of paper so I don’t forget, [00:34:00] but I’m all for it. That’s a great tactic or exercise for people to try. So try it and then contact Kristen if you want to really expand into, uh, a broader. Uh, approach to leadership. Um, so I have one more question to ask you.

This is, um, a final question that we ask all of our guests. Um, Andrea really started this, but I have mixed it up a little bit and changed the question around. So are you ready, Kristin?

Kristen: I am ready.

Christine: Okay. It’s easy. Can you share with our listeners what you do to support your own personal wellbeing?

Kristen: Hmm, that’s a, a good question.

It honestly looks a little bit different. I’m, as we record this, I am come like 28 weeks pregnant almost. So. So, which has been a very humbling experience ’cause I, I’m somebody who tends to just power [00:35:00] through and work through everything and, um, I’ve had to learn to listen to my body and just know when I need to sleep and let things go.

So honestly, right now it’s been a lot of like, just allowing myself to, to sleep and rest and. And nourish my body, um, which has been really good for me. But I would say when I’m not pregnant, um, having like regular move, well, even when I’m pregnant too, like having regular movement is, is key. And trying to watch healthiness, but really just making time for, for myself to just do something that’s.

Fun and has no productivity value to it is, is really key.

Christine: That’s a great response and congratulations. Another surprise, we wouldn’t, you know, we wouldn’t necessarily know

Kristen: probably by the time this airs, the baby will be [00:36:00] born. So,

Christine: and I will say that. We do believe that wellbeing is personal. Everyone’s on their own wellbeing journey, so there is no right or wrong response.

And again, it depends on the day. It depends on where you are in your life. So perfect response. Thank you Kristen. And thank you for being on the podcast. I’m just gonna share with everyone that if you are a leader in your organization, whether in HR or not. I hope you will try to add a little improv into your day to engage your teams.

I think Kristen gave us some great examples. I know I will try a few out. So, Kristen, thank you so much for being my guest on the HR scoop and sharing your insights with us today.

Kristen: And thank you so much for having me. I really enjoyed our conversation.

“Perfectionism is exhausting. But when leaders model adaptability and authenticity, teams start to thrive.” 

This episode covers: 

• • How improv training helps leaders become more self-aware and present 
  • Ways to reduce burnout and build trust through emotional intelligence
  • Small, low-stakes team exercises to foster connection and flexibility