In this executive episode, Adriana Cowdin, CEO of Be Bold Executive Coaching, shares how she shares the knowledge and skills she gained to achieve status in the top 1% of all woman-owned small businesses and uses it to help other founders and CEOs become better leaders.
You will discover:
– The two biggest challenges executives face
– How important relationships are to company success
– In what ways being a non-CEO executive is different or even more challenging than being at the top
Episode Transcript
Scott Ritzheimer
Hello, hello and welcome. Welcome once again to the secrets of the high demand coach podcast. And here with us today is Adriana Cowdin, who is a four time entrepreneur and former corporate CEO named one of the most influential women in business. Couden founded decaf digital, where she served as the CEO for over seven years, leading it to 400% growth in 2022 resulting in an acquisition in 2023 and achieving status as top 1% of all women owned small businesses in 2024 she returned to her roots as an executive career coach, with success coaching 5000 executives, actually more than 5000 executives in the last 20 plus years. She now focuses 100% of her energy on executive coaching at her new company. Be bold. Executive Coaching. Well, Adriana, very excited to have you on the show. Had a ton of fun getting ready for the show and prepping some of these questions that I have for you, and the first one that I have right out of the gate here is we’ve got lots of folks who are founders and CEOs that are listening. And my question for you is, what did you wish you knew about the challenges your executives were facing when you were CEO back at DCad?
Adriana Cowdin
I think the one thing I wish I knew was like, just how important relationships are to the company’s success, not just your success as an executive, but really how the company does. The way we grew over 400% was through some really smart strategic partnerships and all of the little things that go into managing those relationships. I’m very old school. I write handwritten thank you notes and like holiday cards and send anniversary gifts, all of those little things that you do to build that relationship is really what leads to the business to success.
Scott Ritzheimer
Yeah, yeah. So I’ve had a number of guests on the show, and many of them, there’s been some common themes around the unique challenges that founders, CEOs, business owners face at that top of their org chart, if you will, and some of the challenges of feeling alone. But my question for you is, in what ways is being a non CEO but still executive different, or even in some ways more challenging than being at the top of your org chart?
Adriana Cowdin
I think part of the challenge becomes with being able to have open communication with sensitive topics. So let’s talk about a CFO or a chief communications officer, a chief marketing officer, people at the C suite or any executive level, they know a lot of information before the rest of the organization and before their customers and the public at large. So there becomes this conversation around, how do I work with this information, while not giving away any of the secrets, also, you know, and still being smart about confidentiality and sensitive information, which is one of the things I love about executive coaching so much, you serve as that kind of confidential sounding board and person that can help them navigate those scenarios when they can’t just go into their colleague’s office and say, hey, the financials for this quarter aren’t looking great because they’re bound by, you know, the New Year responsibilities.
Scott Ritzheimer
There’s this fascinating kind of sequence of events that I’ve seen, particularly with some of the bigger, more intense. You know, secrets isn’t necessarily the right word, but things that we have to with not disclose openly to everyone all of a sudden, but when indeed that that truth comes out of the announcements made. Let’s put it in a positive you know, we’re doing a new product launch. It’s awesome. We’re super excited about it. New launches out. There’s this like massive relief for the executive team, right? It’s out in the world all this work we put into it, and it’s kind of like we’ve crossed the finish line, but it’s the first time everyone else has heard about it. And so there’s this tendency to think that everyone’s as clear on day one as we are at day 183 6720, however long it’s been. How do you help your executives to recognize where their team is at from a communication standpoint, and make sure that they continue carrying that baton through execution?
Adriana Cowdin
Such a good question. So you know, when it comes to communication, as an executive, actually, at any professional level, the more you can over communicate, the better you’re never gonna again. Put aside, like, the fact that the product launch was secret right now that it’s out there. Talk about, why did we launch this product? What are we hoping to gain with it? What does it mean to the team? Right? There’s always gonna be, you know, the anxious Annie that’s like, what does this mean for me, even if it’s good news, right? And you have to know how to handle that person as well as the person that’s like, the excited Eric, like, let’s just do this. So the more you can communicate with your team about the value of the information, why the company made that decision, what it means to your team, what it means to the company, and what it means to them, the better off you’re going to be. With bringing your whole team along and organization.
Scott Ritzheimer
Yeah. One of the I love the little personifications of those different approaches, because that’s what happens, right? We will have, we’ll have it out, and then, universally, everyone’s thinking, what does this mean for me? Right? It is just natural human tendency. There are only a few people that are either brave enough or scared enough to say it, and so one of the mistakes that we can make is kind of say, oh, that’s just, you know, Ed, or that’s just Nancy, or that’s just, but oftentimes they’re giving voice to what many people are feeling, and you know what their experience has been as well. How do you discern between those two? How do you discern between, hey, this is a squeaky wheel. This is, you know, someone who’s not coming along for the ride, and someone who’s actually just brave enough to say what everyone’s thinking.
Adriana Cowdin
It’s interesting. You kind of learn that that skill in university, like, when, when you ask a question, you’re like, the whole room is like, glad they asked it, right? Like, most people have the same question, but that’s really when non verbal communication comes in, you’ve got to read the room and say and see, like, is someone just hammering home a coin for the personal sake of it, right? Or is the home whole room kind of giving a collected gas and like a Oh, like, shoulders go down because they thought the same thing, right? Right? And really paying attention to the non verbal cues in the room, whether that room is virtual or in person, is just as important.
Scott Ritzheimer
Yeah, I love that. So I have found in the work that I’ve done with teams that there’s two really big challenges that show up in a really significant way at the executive level. So the first one is it’s oftentimes the first level inside of the organization that you have to manage in all three directions. You have to manage up, you have to manage down, you have to manage around and laterally, and essentially, you have to manage out as well with client interactions. So you can make four but what have you found it takes to really excel in in managing in all of those different directions?
Adriana Cowdin
You know, I mean, I hate to comment on the same thing over and over, but relationships and communication being super transparent and understanding what the other person needs, right? Like, if you think of communication as as like a dog ball, a baseball, whatever, if you throw it at someone, well, if you don’t tell them it’s coming that who knows if they’re going to receive it right? So it’s your responsibility to make sure that communication lands properly, and the stronger that relationship is, whether it’s your customer, your upline leader, whether it’s your peer group or your team that reports to you, the more chances you’re going to have to be successful at communication, because we’re all human, so we all make mistakes sometime, right? I forget I sent this email. All sudden I get upset that you’re doing a B or C. If we have a great relationship, you’re going to be like, hey, just a heads up. You actually sent me an email saying that’s totally fine, and I’m going to be like, up, egg on my face, right? But if I have a strenuous relationship, everyone’s energy and anxiety goes up high, and it’s not good around so to your point, there’s probably four places you need to really manage in that that old three circle, 360 circle, right? And I think it’s really important to get feedback, soliciting feedback. I always say feedback is a gift. It’s the biggest gift people can give you, and oftentimes it’s really hard for people to give you feedback. Most. Most of the time, it’s going to be the peer group or your team that reports to you is going to be hard to get feedback from. So whether you’re using tools like anonymous surveys or different one on ones, things like that. You’ve got to be really smart about soliciting that.
Scott Ritzheimer
Yeah, it’s such a simple but important point. We are all human, and it’s so easy to think of those other directions or parties as somehow not human, right? We think if someone’s above us in the orchard, they have it all figured out. Everything in their life is perfect, and they’re just withholding things from us or, you know, and so I love that, and I think it’s right that you, you’ve been reinforcing this idea of relationship and communication, because it is so important, especially because of how dependent we are, in a good way, on teamwork these these days. Which brings me to the second challenge that I see a lot of executives facing, and that is the question of just kind of the tension of competing loyalties, right? In each of those different directions, there’s this question of like, which team is your team? Is it the direct reports that report to you? Is it the executive team that you’re part of? Should you make a decision? Should you be in on a decision that’s bad for your team, but good for the enterprise, right? How do you help folks to navigate what oftentimes feels like impossible situations?
Adriana Cowdin
So I always look at it as try to find a win, win, win, where everybody is winning, right? And compromise really nobody wins. You get there, but not anybody wins. So I’ll use a personal example when I was. Executive at Sears Holdings, and the company is now gone, mostly gone, for lack of a better reason. Every February, you know, q4 would go through all the big revenue, and then it’d be like, Okay, now we have to do layoffs. And so the first time I went into that meeting as an executive, I said, No, I’m not not doing a layoff. Give me a number, a financial number, that you need me to give back to the organization, and empower me to figure out how to do it. And so in that case, I was like, Okay, how can I do this without losing my team members? Because I consider them to, you know, I’m very loyal to them, but I am loyal to the organization. And it comes down to like, okay, maybe we don’t have free coffee anymore, or maybe we watch our supplies, or whatever the case may be. But I did it every year I was there. I never let someone go as part of a layoff, because I would find the money somewhere else. So it’s a matter of being loyal to who you are and the way that you lead, and that allows you to win for the whole organization, the company gets the money they need back, the team doesn’t lose their jobs, and everyone’s fine not having free coffee, given they still have their job, right? So you figure out how to create a win, win, win, and it allows you to be true to yourself as an executive.
Scott Ritzheimer
Yeah, it’s so good. There have been a lot of changes that have been happening organizationally in just about every industry, very, very few that are even remotely untouched by changes in technology, everything that came out of COVID, political environment, even recently this this past year. What? What have you found are some of the like, real big, core, common challenges you’re seeing with your executive clients right now?
Adriana Cowdin
I think the biggest challenge is actually AI, which sounds a little crazy, because there’s almost two groups, like people that lean into it, love it and use it, and the people that are like, it’s gonna take over the world. I’m afraid of it, and it’s like anything new, right when, when the iPhone came out, when the BlackBerry came out, there were early adopters and people who kind of slowly transition. And so when you’re looking at something as influential technology wise, as something like AI, you have to be smart about the fact that, again, you’re going to have some people that are super scared of it and some people that embrace it, and you need to figure out which is which person right and lean into what it is that they’re comfortable with. It’s always good when you’re out of your comfort zone, I say that’s when you grow like when you’re out of that comfort zone, but pushing people too far just causes anxiety. So find those people that really want to lean into innovation, if it’s AI or something else, and lean into those people and work with the other people that aren’t in that area on whatever they want to lean into right like it’s identifying the right skill set for each person while also embracing what’s going on at the world at large, right? Like AI is here, so there’s got to be a way to integrate it.
Scott Ritzheimer
There, there are a number of folks listening to this, and they’re either aspiring to be an executive, or maybe it’s a founder CEO, and they’re trying to assess whether some of their people are ready to be executives in that kind of structure. What does it take? What are some of the just kind of two or three top skills that you found are necessary and should be assessed for someone who’s either looking to become an executive or be promoted into an executive role?
Adriana Cowdin
The first one, I would say, is grit. It is not easy to be an executive. It’s not like, you know, jet sitting here and there and having lunch with everyone, like some, you know, kind of front line thing. The second is gut. You have to rely on not just your head, but also your gut to know the right decision. And the third would, I think, be relationships in terms of culture. How does that person fit in your culture and where you want culture to be? Because you might be a great executive in Company A, but not so much in Company B, because it doesn’t align with your personality and you don’t align with their culture. And there’s nothing wrong with that. It’s just not a not a match, you know, it’s misaligned, and you really do have to do that cultural tat.
Scott Ritzheimer
I love that. I love that. So, Adriana, there’s a question I like to ask all my guests. I’m interested to see what you have to say as well. What would you say is the biggest secret that you wish wasn’t a secret at all? What’s that one thing you wish everybody watching or listening today knew?
Adriana Cowdin
Believe in yourself, meaning, you know, when I started out any of my businesses, I started with, this is what this company does. This is the problem we solve. This is how much we make per year, blah, blah, blah, before we solved a problem, before we made $1 and so that belief in your. Self, whether you’re an executive or an entrepreneur, that mental fortitude is going to take you further than almost anything else. You’ve just got to have the mentality to say, I can do this. I’m amazing. Watch out world.
Scott Ritzheimer
I love that because it goes face to face. A lot of folks don’t really recognize this one how intensely personal so much of this journey is. We talk on the show a lot about the personal journey of founders, but also just executives and career professionals. It’s still your life, right? It’s not all put on hold, and the imposter syndrome that we all face. The best way to fight against that is that one thing is to believe in yourself and take action and move so I love that there’s some folks listening. They’d love to have an executive coach. They’d love to have someone in their corner that they can confide in, that they can move forward with. How can they reach out to you? Find one about the work that you do?
Adriana Cowdin
beboldexecutivecoaching.com. You can find all kinds of free resources on our blog. You can contact us directly. You can also find me on LinkedIn under Adriana Cowdin, but yeah, go to beboldexecutivecoaching.com We’d love to talk to you.
Scott Ritzheimer
Fantastic Adriana. Thank you so much for being on the show. It’s a privilege and honor having you here today, and for those of you watching listening, you know your time and attention mean the world to us. I hope you got as much out of this conversation as I know I did, and I cannot wait to see you next time. Take care.
Contact Adriana Cowdin
Adriana L. Cowdin is a 4-time entrepreneur and former Corporate CEO. Named “One of the Most Influential Women in Business,” Cowdin founded Dekaf Digital, where she served as the CEO for 7+ years, leading it to 400%+ growth in 2022, resulting in an acquisition in 2023 and achieving status as Top 1% of all woman-owned small businesses. In 2024, she returned to her roots as an executive career coach. With success coaching 5,000+ executives in the last 20+ years, she now focuses 100% of her energy on executive coaching at her new company, Be Bold Executive Coaching.
Want to learn more about Adriana Cowdin’s work at Be Bold Executive Coaching? Check out her website at https://adrianacowdin.com/
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