355 - Leadership in a Changing World: Insights on Team Development and Artificial Intelligence with Megan Boveri
13 Jan 2026 · 24 min
In this episode of Listening with Leaders, host Doug Noll interviews Megan Boveri, Chief Media Officer at Pinnacle Advertising, about her journey from a farm upbringing in rural Illinois to leading a 45‑person media team in Chicago. Megan explains the breadth of her role, which blends creative storytelling, media buying, and data‑driven analytics, and she describes how artificial intelligence is being used to streamline both creative concept development and the “mathy” media planning side without replacing human insight. The conversation shifts to leadership, where Megan highlights the importance of trust, emotional intelligence, and making team members feel valued—principles that echo Doug’s own research on leading the emotional brain. She shares concrete practices for developing future leaders, including dedicating 30‑40% of her time to people development, delegating decision‑making, and teaching the why behind processes so teams can adapt when standard workflows break. Megan also reflects on the personal challenges of moving from a hands‑on producer role to a strategic leader, the need to find long‑term fulfillment over daily tangible output, and her passion for crafting detailed travel itineraries as a creative side project. The episode weaves together insights on media industry evolution, AI adoption, team empowerment, and personal growth, offering listeners actionable ideas for leading in a rapidly changing business landscape.
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Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started. Megan Bovary, welcome to Listening with Leaders. You are the Chief Media Officer of a company called Pinnacle Advertising in Chicago. Let's just start off. Yeah. Let's just start off with a little backstory. You told me just before you got started, since I live in rural California, that you were a farm girl.
That's right. I grew up in rural Illinois, basically middle of nowhere, farmland Illinois. Been in Illinois my whole life actually. So I grew up on a farm in Illinois, ended up going to college at the University of Illinois. First chance I could get, left the farm life and am up in Chicago. Been up in Chicago ever since graduating from high school. But of course now in hindsight, I really miss the farm life and would like to go back.
Isn't that amazing how that works?
Yep. Yep. So someday post-retirement, I do hope to get back to more of a rural existence.
I can tell you, I grew up in Southern California and then went back east to school and ultimately after law school ended up in Central California. And today I live on 10 acres in the Central Sierra Nevada and I wouldn't change it for anything.
That sounds lovely.
It's pretty good. Tell us a little bit about your, what you do as a Chief Media Officer with Pinnacle and a little bit about Pinnacle.
Yeah, so Pinnacle is a full-service advertising agency located just outside of Chicago. When I say full service, that means we do all of the creative, all of the media, the strategy, the analytics, basically everything from soup to nuts from a marketing standpoint, we can handle internally. My job as part of that is running the media department. And what that means for people who aren't as familiar with the advertising world is that is what I like to say, the boring mathy side of the advertising business. So you think of advertising. And you think of the creative and making the commercials.
Right.
What you don't think about is someone has to get the commercials from the production suite to the actual TV screen, to the radio, to the digital internet. And that's my job is to basically take these brilliant ads that my coworkers are making and get them in front of the right people that are going to convert and buy our clients' products.
And then you have to track all the metrics around that.
Yeah, it's super analytics heavy, especially with the rise of digital. You can track just about everything. So we can know that, you know, you saw our ad on Fox News at this time and then later went to the website and made a purchase. So we can basically track just about everything. And then we use that data to optimize where we're investing on behalf of our clients to get the best outcomes.
How, how is AI changing the world?
AI is absolutely changing the world. So it, it changes things on both the media side and the creative side. So the creative side is a little bit more obvious, right? Because that's where you can use the creative to help with the storyboarding, help with creating the concepts. There are agencies that will do entire productions that are only AI. We're not there. We think it's really important that you have that human in the loop, I think is what people call it, making sure that we have the human element. Like, we don't use AI to create our ideas. We might use AI to make them more efficient. So showing a client— so between the idea and the actual commercial being shot, there's stuff in the middle, right? Like storyboarding and concepts. And what we'll do is we'll use AI to help bring to life those concepts so that the client can really fully visualize it before we move on to formal production. So we definitely are absolutely using it to be more efficient, but we're not using it to replace human creativity and human ideas. It's similar on the media side that, like I said, is a little bit more mathy. So there's tons of opportunities for AI to help take out some of that, some of the grunt work and the stuff we don't want to be doing anyway. We want to be spending our time building strategies and negotiating with vendors and talking to clients. What AI does is it helps us create efficiency in some of the stuff we wouldn't want to be spending our time on anyway. Way. So it's been a huge helper from that perspective.
I'm curious, how did you get into this business? You go to college, how do you decide to go into marketing?
I went to college, I majored in advertising. This is actually a horrible story, which I shouldn't be saying to your listeners who I know are all good business people, and this is actually an embarrassing story, but I'll say it anyway. The reason I ended up in advertising is because I had no idea what I wanted to do. I went to the University of Illinois. I knew I wanted to go there, but I didn't know what I wanted to major in. So I went in as undecided and basically The second semester sophomore year, the University of Illinois forces you to pick a major. So at that point I had to buckle down and I was like, I don't know. So a sorority sister said advertising's easy. And I said, cool, I'll do that.
And here you are.
Here I am 20-some years later and I could not have been more wrong. Advertising is not easy. I will say the major actually was pretty easy, but living and breathing and working in advertising, it is a very challenging field. My sorority sister was very wrong. But I love it. I'm still here.
You graduated and just started off as a young person out of college and just worked your way up through the ranks.
And that's right. I started, so I've been in media my entire career. So I was an advertising major. And usually, like I said, when you think of advertising, you think of creative, or maybe you think of account services. So media wasn't even on my radar. I didn't know that existed. And then my senior year, we did a class, two things my senior year that kind of pushed me in the direction of media. First, we did a class that was actually focused on media. That was the first— not until my like second semester or senior year did we even have a class that mentioned media. So I finally had a class that was all about the media side of the business, and I realized I really liked that. Media brings a nice tangibility to the creativity of advertising. So it's still creative. You still— you have to understand people, you have to understand how they operate, you need creative ideas to get the messaging in front of them. But as I mentioned, there is like a mathematical and analytical component too. So it's a a really nice balance of the creative and the analytical that I really liked. The other thing my senior year is we got to work on a real-life project. And so we all took different roles. And so one person was the account person and one person was the creative. I got assigned as the media person. So I was able to get some actual hands-on experience of what do media buyers do. And I really liked that. And then Starcom, which is where I worked for almost 20 years of my career, they recruit very heavily out of the University of Illinois. So they came, they recruited. I liked them, they liked me. They had me come up to Chicago for a shadow day where I got to meet the team and get a little bit more firsthand experience on what is this whole media thing. And I loved it. So I started there like right after school, had a job before graduation, which was amazing. Started right after school and worked there for the next 18 years. And then 2, about 2 and a half years ago, I got recruited away from my current boss at Pinnacle Advertising and have been there since.
Wow, good for you.
So a lot going on there.
When you were at Starcom, you don't need to name names, but if you think about the attributes of the best leaders that you worked for at Starcom, what would you say those attributes are?
My favorite boss that I've ever had, and it wasn't because she was the smartest boss I've ever worked for, because she wasn't. Like, I've worked for really smart, brilliant people, people that are really good at problem solving, people that are really good with clients. The reason I think that she was so successful and ultimately the team was so successful is she believed in her team members like even more than they believed in themselves. So I think there's that whole mantra of you'll work up to the level of trust that people put in you. And that's, I think, what really epitomized her is she thought I was great. And so I wanted to be great to work up to that level of expectation. So I would say I grew fastest under her than anyone else, even though she— I'd worked with a woman before that who was absolutely brilliant, but she doesn't make you feel good about yourself, right? And it's like when you're not feeling good about yourself or that you're not doing enough or good enough on a daily basis, that starts to impact your performance. And it's obviously you're trying your hardest to impress this person, but if they're not believing in you, you're not really believing in yourself. And then I went from her to a very different boss, which a complete 180. Like I said, she thought I was absolutely wonderful, so I worked up to the level of being absolutely wonderful to fulfill her expectations.
So you are epitomizing a principle. I've got a book, my fifth book's coming out in the fall on leadership empathy. And the principle is that most leaders only lead 5% of their team's brains, but the brilliant leaders lead the 95%, which is all the emotional brain. And it sounds like that's what that particular leader was doing. Would you?
I think so. Yeah, absolutely.
What'd you take away from that for your own career?
Exactly that in leading a team now, it's not, What you say to people, it's like how you make people feel, and that's what matters. I am not as good at it as I would like to be, but I do every once in a while take a step back and think about that story from my own experiences. Teaching you how to do the job is exactly your point. Me teaching you how to do the job is only a very small percent of being a leader, and a lot of it is that intangible of how you make people feel about themselves, how you build them up and make them feel that level of trust that you have in them. And ultimately, they want to work up to that level of trust, achieving things that maybe they I wouldn't have otherwise. So I would not say I'm great at it, but I'm working towards being great at it.
We all continuously improve. How many people do you have reporting to you?
45.
45? Yes. So you have people that report to you and they have people reporting to them?
Yes. All— yes, not all 45 report to me directly. So there are 45 on my team. Directly reporting to me is maybe like 6.
And what have you learned about listening to your team?
It's critically important. Again, going back to that same mantra, it's like how you make people feel, right? And you want them to feel that you care about what they have to say, that you're really listening, that you're not only listening but hearing what they have to say. Again, I will— I am not the best at it. It's a constant struggle to not be the person that jumps in to solve the problem, right? Because I was like, oh, I know how we should do this, but people don't learn and grow in that capacity. So I really try to force myself to not talk in some of these bigger group settings and let them kind of figure things out and then listen. And then we can go back later and talk about, okay, I, here's how I heard that you approached this. Let's talk about your thinking, et cetera. Because again, it's helping people think, not necessarily teaching them how to do a specific task that's going to help them grow.
Yeah, I think that teaching people how to think is probably one of the most important things a leader can do. Critical thinking is, we're really short supply of people who can critically think these days.
Yeah, I 100% agree with that. And that's been a problem on the media side of the business because it does have that analytical component. There's a lot of process, right? And it's, you do this and then you do this and then you do this. And where we've gotten in trouble is you teach people the process, they get to the point where they're really good at it, and then inevitably some step in the process breaks for whatever reason, and they have no idea what to do because they haven't learned how to think about it. They've learned how to follow the process.
Yeah. Yeah.
So process is critically important in my business, but I'm always trying to balance that with not only do you teach somebody the process, you teach them why the process exists and why we're doing each step in the process, because inevitably the process is going to break or you're going to come up against an example that just doesn't fit the standard mold. And you need people to be able to think through how to get to the next step rather than just following the step in the playbook.
And you find people are pretty good about wanting to learn that stuff, or do they get a little frustrated because it's difficult?
It depends. It's, I'd say it's a pretty decent split. There are people who really love the challenge of thinking through the process and the structure and why are things the way they are and questioning. There are people that absolutely love the process and get frustrated when the trains fall off the track and you, and the process doesn't work. So it's part of it is just helping those people that do struggle to get back on the track. But the other part of it is just like knowing where people's strengths lie. The people who are just excellent at process, we have an operations team that's under me. Those people are excellent at working in operations, which is a little bit more step-by-step formulaic, whereas the people who are always asking why and questioning the process, I have them on my strategy team. They're working with the clients and building out high-level strategies, which is much more nebulous and less formulaic. So it's finding where people are best suited for the individual roles in the organization.
Wow. What is it about you, Megan, personally that you bring to the table that has made you such a successful leader?
I think at least part of it is I love to learn, right? Like, media is a business that is completely different every 6 months, like, especially when you get to digital. That used to not be the case, right? We had 3 TV stations, a handful of magazines. The job was not all that hard. Now with digital and AI and mobile and social, like, there are so many ways to get in front of a consumer. It is an incredibly complicated business, and digital evolves so quickly. And now with AI, it's evolving even more quickly. So you have to constantly want to be on that cutting edge and want to be educating yourself to be successful in the business. If you decide to take a break for 6 months, like, you'd be completely left behind.
What strikes me is, for example, on LinkedIn, the algorithm seems to change every 3 days.
Yeah, Meta is the worst. Yeah, you, you understand it and you're like, got it, I know how to run a Meta campaign. A week later, they've changed the UI or the algorithm, and you're starting over. So it's you have to like that and be comfortable with that to be successful in media because it is definitely not a set it and forget it industry.
Yeah, that's really challenging.
Yeah, but that's what I like about it. That's what makes it fun. If it was, if you're doing the same thing every single day, so again, some people like that, that side of it and they thrive in our operations department. Someone like me is, that would get boring so fast. And so being able to like constantly be learning and educating myself and finding out what is the next thing on the horizon is fun and exciting.
How, how much time do you spend developing the people underneath you to become leaders?
I would say probably 30 to 40% of my time. Yeah. Is spent just doing like management and leadership. So I spend probably 40% of my time on new business development for the agency, probably about 30% on people development, and then the rest is spent managing our current clients.
Wow. So it, that's funny. You're talking about the complexity of the business, but you're spending a really significant amount of time on your people.
Yeah, at the end of the day, that's my job is to build the next generation of leaders. Like, I can't write every plan. I can't be in every client meeting. I try to be in every client business pitch, but I can't be in all of them. So I have to be able to build up my people to be able to do that without me there. And then, like I was saying, make sure that they know that they have my full confidence and trust. So then they work up to the level of that confidence and can do it without me having to be be part of every single project.
How did you learn how to let go?
I am not great at it. It is really hard. I'd say a lot of it has been forced because there, there is so much complexity in media. There is stuff that I just don't know as well as other people on my team. So I was forced to let go and let them run it. I'll give you an example. We do a lot of automotive advertising in our agency. And because we have a 26-year heritage, most of that in automotive, so we have some people that are just excellent at automotive marketing. I had never done automotive before I joined Pinnacle, so I need to trust that my people who are experts in automotive can get that job done without my oversight. And because of that kind of forced letting go, I was able to see, yeah, I don't need to be in every meeting. They have got it absolutely under control. They'll call me if they need me, but it, for things that I know intimately well, it is much harder because it's just because they do it a way that works. It's not the way I would do it. So I try to, uh, the, what I always tell my team is I actually don't care what your plan is. Like when you're building a media plan, I don't care what the plan is. I care that you have justification to support it. If you say, if I want CNN instead of Fox News, I don't care either way. But I need to know that you've thought through it. So I ask a lot of questions, which I think can sometimes come off to the team as critical of— I'm questioning their judgment. That's not my intention. I just want to make sure that they have fully thought through why their recommendation is what it is. And if that's the case, then I'll stand behind it and support it to a client or to anyone.
How did it— strikes me that one of the challenges of being a leader is that especially if you come up through the ranks like you did and for a long time you were a producer, right? You produce. And then when you become a leader, now you've got a lead people who are producing. You're no longer producing yourself. That's a hard transition.
It is a hard transition. And part of it is just mentally, right? Like without the tangibility of I made this today.
That's right.
It's hard to feel like you were productive. So it's a very different kind of productivity and value. And it is hard because I used to and still to some extent to this day do derive value from creating things, from writing strategies, building new business presentations. Like there is a lot of immediate and tangible feeling of value from that. Whereas when you step back and you're leading the people that are creating the things, it's much more of a long-term. It's like you don't necessarily feel like you're creating value every single day. It's over the long term where you can see the outputs of all of your efforts when you start to see your people grow and develop. It's mentally difficult.
It is. I think it took me, I guess it was in my late 40s when I finally figured out that just my presence was enough. If I had a presence, a leadership presence, that's all that was really required of me. A calm, stable, safe foundation is there for people to work. And as long as they've got somebody to focus on who is stable and projects a presence, then that was enough. That was hard. That was really weird getting used to that. I'm not doing anything. I'm just being present. You know, that, that's pretty easy.
It is hard. And I will not say I have fully gotten over that hump, but I definitely know that it's true. So I see that I can provide more value to the organization by developing an army of media leaders that are excellent rather than being one excellent media leader myself. So I understand it in my brain, but getting past that mental hurdle of, did I provide value today? Is, it's a challenge for sure.
That's the other problem is when you're a producer, as you pointed out, you get a sense of self-worth and a sense of fulfillment. You can see what you've done, but as a leader, you don't get any of that.
Yeah. It's maybe longer term. Yeah.
Or you look at, maybe it's a quarterly, maybe it's your quarterly numbers or something like that, but they're all intangible.
Yes.
And so finding the instant gratification is a lot harder.
Yeah, exactly right. Because it is that what those longer-term metrics that are showing that you're doing a good job as a leader. So you don't have every single day the thing to point to, to say, look at all the things I did today.
Yeah, exactly. So where do you think your career is going? You're in mid-career right now, I think.
Mid-career. I don't necessarily have any desire to leave the media business. It's the only thing I've ever known. So I probably will stick around in this arena for a while. What I'm starting to realize through this role, which is a little bit different than the role I did at Starcom is I like the business side of the business. So really like the running of the agency. So the operations, the finance, the HR. I, I don't run those things now, but I'm part of that executive leadership team. So I have more purview into those sort of things than I did before when I was truly just like running media teams. And I like that. So I'd like to learn a little bit more on the business side of the business of like, how do you actually run an agency?
Yeah, you might become a CEO someday, who knows?
Maybe someday. I never really thought that was my ambition, but now that I— as I get closer, it actually does seem like a lot of fun.
Good for you. One more question, I'll let you go. What's one thing, Megan, about yourself that we would never know about unless you revealed it to us?
I think if I wasn't doing this job and if I could make money out of it, my ideal job would be like writing custom travel itineraries for people. I absolutely— like I said, I love to learn, so I love researching new places. And I personally love to travel, so every time I take a trip, I spend a lot of time— I go to the library and buy all the books on the place we're going. I do research on Pinterest and ChatGPT and all of that, and I write out these like very detailed itineraries of all of the things we're gonna do by day. I try not to get down to the minute. I want to leave a little bit of room for spontaneity, but by day, these are the things we're gonna do, and then we're gonna drive here and do these things. And I like— I really enjoy doing that, so I would love to make a career of that, but I don't think there's a ton of money in there.
Probably So when you're on one of your trips and something goes sideways, does that throw you for a loop or you just laugh and say, oh, I've gotten better.
So I historically was very Type A. I will say I, I've mellowed out a little bit in my older age, my middle age. So I still write the itineraries, but I write them with a little bit more flexibility. Whereas before I'd say at 10:00 AM we're doing this and at 11:00 AM we're doing this. And then obviously things get thrown off and then the whole itinerary's out of whack and I'm grumpy. Gotten better. I've gotten better by just saying, okay, this day. I'd like to for sure do these 3 things. If time allows, here are 4 more options. And then I'll just, we'll go through the 3 things and then I'll talk to my family of, okay, here are 4 other things we can do. What do you want to do? So I've gotten better about going with the flow as I'm getting older.
So you're not Miss Grumpy all the time.
I'm not grumpy all the time, just some of the time. Great.
Thank you so much. It's been a wonderful conversation.
Yeah, thank you. It was so nice meeting you.
You're welcome. Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com/podcast. If you got something out of this interview, would you please share this episode on social media? Just do a quick screenshot with your phone and text it to a friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content. To make sure you don't miss any episodes, go ahead and subscribe. Your thumbs up, ratings, and reviews go a long way to help promote the show and mean a lot to me and my team. Want to know more? Go to my website, DougNoll.com, or follow me on LinkedIn, Facebook, and Instagram. That's @DouglasEnoll. Thanks for listening, and we'll see you on the next show.
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