Ryann Dowdy’s first leadership role didn’t come with an official title that told everyone she was “in charge,” and yet, she was. With her lack of title, Ryann realized people were much more comfortable sharing their ideas and concerns with her because she wasn’t technically their boss.

Now, as CEO and Founder of Uncensored Consulting, Ryann leans into emotional intelligence to encourage the same openness from her team, regardless of role dynamics. Creating workplaces where people feel seen, heard, and valued is critical for both attracting and retaining talent in today’s market, and she’s made it her mission to do so. In this episode, Ryann explains why leading others starts with self-leadership and discusses her six principles for achieving exactly that. Listen in to learn how to build trust and motivate people through meaningful work.

After You Listen:

Get your copy of Extreme Ownership by Joko Willink and Leif Babin

Learn more about Jamie Kern Lima

Check out Ryann’s female leadership community: Be in the Room

Connect with Craig: https://www.linkedin.com/in/craigpanderson/

Learn more about ClearPath Consulting and Coaching: https://clearpathcoaches.com

Download Craig’s 10 Rule’s for Better Meetings

Key Takeaways:

• There is no cookie-cutter way to lead humans; get curious and figure out what motivates your people
• You have to learn to lead yourself before you can lead others
• Make work about meaningful contributions instead of just money

Things to listen for:

[01:13] Lightening round with Ryann

[03:36] The benefits of leading without the title

[06:26] Combining emotional intelligence and high achiever

[09:47] Ryann’s self-leadership principles

[12:25] Motivating people with meaningful contributions

[13:38] Advice Ryann would give to her younger self

[24:37] Craig’s takeaways

Ryann’s Transcript

Craig P Anderson:

Welcome to The Accidental Leader Podcast, the only leadership podcast that shows how today’s successful leaders develop the competence, confidence, and calm to lead their team and organization to success. I’m Craig Anderson and my career journey is a tale of accidental leadership. I started out with a degree in English and a growing comic book collection, and my plan was to be a high school teacher, but what we plan and what happens aren’t always the same thing. A college job turned into a career in education finance, an entry level in my alma mater became over time increasing leadership roles in Fortune 500 companies, including many national leadership roles. As that chapter closed, I spun off a business from a large operating not-for-profit and grew that into a successful business that was named a great place to work in Indianapolis. Over my career, I learned a lot of leadership lessons the hard way. I created this podcast so you don’t have to.

My guest today is Ryann Dowdy, the founder of Be In the Room and the Self Leadership Principles. I’ve known her for a couple of years now, and I’m excited to have her on the podcast. So, welcome, Ryann.

Ryann Dowdy:

Hi, Craig. I’m excited to be here.

Craig P Anderson:

I’d like to jump right in and get the energy going with some lightning round questions and then we’ll dive into your leadership story. So, question one, what is the best leadership book you have ever read?

Ryann Dowdy:

I told you that I did not know the answers to these questions, but the best leadership book that I’ve ever read would probably be Extreme Ownership.

Craig P Anderson:

Oh, you are the second person who has brought that book up.

Ryann Dowdy:

It covers everything in life. Right? Not just business, extreme ownership for ourselves. It’s a powerful book and they tell stories well. I listen to it and it’s the two retired Navy SEALs who talk through it. It’s a good one. I enjoyed it.

Craig P Anderson:

Question two, who is your leadership crush?

Ryann Dowdy:

All the people teaching leadership are old white dudes and I’m not super impressed by any of them, but if I had to pick a woman who has really blazed the path for women leaders, it’s Jamie Kern Lima. She is the founder of IT Cosmetics. I don’t know if you know that whole story. So, she founded IT Cosmetics in her living room and sold it to L’Oreal for $1.2 billion 10 years later. She’s got a killer story. She’s got a book and she talks a lot about leadership and all those different things and having to really believe in herself because there was a lot of adversity in her journey. She was told to do things a certain way. She didn’t want to do them the way the industry told her that she should. So, a lot of doors shut in her face and she had to get creative.

Craig P Anderson:

All right. And then last, in 10 words or less, how would you define leadership?

Ryann Dowdy:

Leave people better than you found them. Our job as leaders in my opinion is to inspire others. Right? Inspire others into action, inspire others to be the best version of themselves. So, for me, when I think of when I’m leading, whether I’m leading a team of people inside of my own company, whether I’m leading workshops for people who just want to learn the things that I can teach, or whether I’m just showing up online as a leader, I always think of that place of how can I serve others. When somebody reads this, listens to this watches, this sits in this workshop, works for this company, how can I make sure that they are a better version of themselves when they leave?

Craig P Anderson:

I love it, yeah, because we’re all transitory in our careers now. It’s not like my grandfather working for the same company for 50 years. That’s a great view. So, speaking of the long view, let’s go back because you’re like me, you’re in an entrepreneurial space now, but you were a corporate America person for a while. Let’s go back. What was your first leadership role?

Ryann Dowdy:

There’s almost two versions of this story. There was the first time I was put in a position of leadership where nobody reported to me, and then there was the first time that I had direct reports. So, my first actually parlay into leadership, I was a sales trainer, I was a regional sales trainer for a startup and I trained sales teams. And so, I was in a leadership role as that I would go in and again conduct training, do four-legged sales calls, I would give feedback to managers about how they could better manage their people. That was kind of my first people saw me as a leader, but I didn’t have any direct reports in that role. And then eventually many years later, I did finally get to a point where I was leading my own team of sales reps, and that’s actually the job that I retired from before I became an entrepreneur.

Craig P Anderson:

So, it’s interesting because a lot of times we can lead without having a title, and it sounds like what you’re saying there. So, how was that for you leading without a title?

Ryann Dowdy:

I’ll be honest, that was most of my leadership. I would say I spent more time leading without a title than I did with a title and I really enjoyed it, and the reason is, because it was through when I was training and then I was a channel sales manager, is I found people were more open and honest with me than they ever were with their leaders.

So, when you are having a conversation with the person who is your boss, right, the person who decides if you get to come to work tomorrow, I think companies are getting so much better at this, Craig, but there’s not a lot of space to be… It doesn’t feel safe to say I some days feel like I don’t know what I’m doing, or I some days feel like I don’t have everything I need to do my job well. Nobody wants to say that to their boss, but they’ll say it to the third party person in the room. Even though I work for the company, right, I wasn’t a consultant, we all got paycheck from the same place, they would tell me those things. Right? I feel like we’re really missing these kind of marketing materials, or I feel like my manager doesn’t really understand this side of things, or I feel like we’re not getting a lot of support here and they would tell me those things.

So, I actually really loved it because people were very open and honest with me about what was going on inside of the organization and it allowed me to make a bigger impact. Again, I talk so much about the work that I do and Be in the Room is creating a safe space. That’s what I did in those kind of third party roles was I was that safe space for those people. And of course, obviously, I had to report anything gregarious or anything anybody told me, but I didn’t need to verbatim tell you that hey, this guy thinks his boss is an asshole. Right? I didn’t have to go back and say that. I’d say, “Hey, I think there’s a huge opportunity for the leader in this market to do this, this, and this to better communicate with their people.” So, I was able to kind of be that buffer which I really enjoyed.

Craig P Anderson:

Nice. Yeah, and so many times especially people need that leader between them and the higher leaders that can work those messages because I was pretty raw when I was an independent performer about my feelings sometimes. So, nice. So, you transition eventually into having some direct reports. So, looking back on your first turn with direct reports, how do you feel you did?

Ryann Dowdy:

Terrible. I hated it. When I became an entrepreneur I swore I would never have a team. The people management side was just not… I’m a high performer, Craig. I get things done. I’m a High D. I’m an Enneagram three. It really blew my mind when I had direct reports that people half-ass their jobs. I didn’t understand it. It did not compute. When my boss asked me to do something, I did it. I would ask people to do things and it wouldn’t get done, and I was like, “Are you okay? Are you sick? What is wrong with you?”

Again, I didn’t handle it well, and I will say in all fairness that I didn’t have a lot of good examples of leadership either. Right? I grew up in a time of the very authoritative, leader and especially in sales organizations. I led sales teams. Right? So, we were very numbers focused, very performance focused. Right? You earn your seed every day, that just very, ugh, gross environment. And so, I didn’t handle it well in that it was like I didn’t have the emotional intelligence to say, “Hey, I noticed that you didn’t turn that thing in that I asked you to. Is everything okay? Do you need help? Do you understand how to do the assignment?” It was like, “Where’s your stuff?” And as you can imagine, it wasn’t well received.

Craig P Anderson:

It’s so different doing things when you’re a high performer, especially when you’re a high performer, and then they place you… It’s classic sales. You’re a high performing salesperson, I’m going to make you a manager, and now you have to do that through other people. But people sell differently. You can have three successful salespeople and are all successful for different reasons. So, what was your biggest leadership lesson from that experience that you took away, aside from I don’t really want to have people?

Ryann Dowdy:

Not everybody is motivated like I am. And again, this is in a sales arena where it’s like okay, we’re just all money-motivated, performance-driven, competitive people. That’s who tends to be drawn to sales careers. And so, it really, I had to zoom all the way out and think about every person needs to be managed differently. Even though all the people might have the same job, it all has to look different. There is not a cookie-cutter way to lead humans.

Craig P Anderson:

People are messy and people are difficult and they have different, as you said, different motivations. So, it’s really a challenge. So, now let’s cycle forward to where you are now. Tell us about where your leadership opportunities are today.

Ryann Dowdy:

I do have a team, and it’s actually very funny, it’s one of my biggest aha moments of entrepreneurship is I found I actually really do enjoy creating employment. I enjoy creating a place for people to work where they feel seen, heard, understood, valued, where they’re respected, they have an opportunity to be creative and share their ideas and work around their life, and all of those things. So, I actually find an immense amount of joy in that which I was very surprised to learn once I learned enough about myself as to how to be a good leader.

So, I do currently have a team of two. I run a community called Be in the Room which is a women’s leadership organization, and I wear the hat of leader, but what’s really cool about that community is I also wear the hat of participant. That’s also a place for me to go and ask my questions and air my grievances and talk about what’s going on in my world. So, I really love that too. And then getting back into kind of playing that third party role again in working with sales organizations to build sales training programs.

Craig P Anderson:

So, when you think about those lessons you took away from those early leadership roles into how you’re leading today, what were the things that you brought forward that informed you? You talked about the emotional growth, the emotional intelligence, but what did you really bring forward that made you a better leader now?

Ryann Dowdy:

It actually is, and this was so not intentional, it really is the self-leadership principles. So, I just recently kind of pushed publish on these six principles that are not new principles, Craig. I’m sure you talk about them ad nauseum in the leadership world, but the self-leadership principles where it’s about building a relationship with yourself first. I believe to be a good leader, you have to lead yourself first, and that starts with simple things like the first leadership principle is self-trust. If you don’t trust you, how are your people going to trust you? If you don’t have a clear vision of where you’re going, how are you going to get people on board to go with you?

That was definitely something I didn’t have early on in my career. I talk about personal responsibility and self-awareness, what’s my job, what role do I play in this, and knowing my strengths and weaknesses. Those were things I did not know. And even like I said, emotional intelligence, learning how to control my emotions, understand my emotions, understand other people’s emotions, see those emotions, those are all things I had to learn how to do for myself first before I could ever do them for anyone else.

Craig P Anderson:

So, it was really for you, the leadership growth was more the internal journey and dealing with all those things, and then that allowed you to externally be the leader that you wanted to be maybe, or maybe you didn’t even realize what you could be.

Ryann Dowdy:

Right. I think it’s more I didn’t realize that I could be because again, to me it was not a good thing. It wasn’t something I enjoyed.

Craig P Anderson:

And is that kind of beat down management style of sales, do you see that as something that we need to get away from for sales organizations?

Ryann Dowdy:

It’s so interesting to me. We’re like, “We have this part of our organization that’s like full of aliens.” Dude, come on. No, it’s not. Right? Our most basic human need to feel seen, heard, and understood, we never ever, ever think about that with salespeople. What do they need to go out and do their jobs well? Right? So, if we replace it and actually teach our salespeople emotional intelligence and teach our salespeople how to be empathetic, connected humans, they’re going to sell better, they’re going to sell more, our clients are going to get better results.

So, I think it all goes back to so much of what we’re seeing this huge shift in conscious leadership and this shift in human-focused leadership and what you were sharing with me before we pushed record. Right? Your son is 23 years old, he’s in the corporate world and he is like, “We’re not going to work 60 hours a week.” I think I read a stat today, in 10 years, 30% of the workforce is going to be Gen Z and they’re not going to work 60 hours a week. So, we have to figure out how to lead those people well, or they won’t work because they don’t have to. They can make the same amount of money playing on TikTok as they can working for today’s corporate America organizations. So, we have to change.

Craig P Anderson:

Yeah. I think what I’m hearing is to get more out of people going forward, we’re going to have to meet them where they are and give them the tools they need to succeed as opposed to just that beat down rah-rah. I think of, what is it, always be closing and coffee is for closers, that’s just gone.

Ryann Dowdy:

Oh yeah, that was at a conference and I listened to Brendon Burchard talk. He was talking about it from a marketing perspective, but as far as I’m concerned, sales is leadership, marketing is leadership, vice versa. Right? And he talked about meaningful contribution. All of us want to make a meaningful contribution, and chasing a number on a leaderboard is not meaningful contribution, and that’s how we lead sales organizations. Right? Chase the number. Chase the data. Chase the things. Who’s the highest performer today? That’s not meaningful contribution.

So, the question, how many deals you’re going to close today is how many lives you’re going to change today. Instead of how many calls you’re going to make today, it’s how many people are you going to connect with today. They’re small nuances. I know it’s semantics, but it matters. Right? It’s the energy behind it, how it feels when we get on the phones or make the calls or do whatever it is we have to do our job well. So, I think it’s just really going back to helping people feel like they’re part of something bigger than themselves, and we don’t do that in sales organizations because again, we just dangle the money carrot and pray they run.

Craig P Anderson:

And I think that ties back to what you said early on about creating the vision as the leader. When people can buy into the vision and get excited, whether you’re selling self-leadership or you’re selling steel or you’re selling whatever, when you see how you’re making a difference, it drives behavior. I’m a big sci-fi geek. So, if you could go back in time in a time machine and tell yourself in those early leadership roles one piece of advice, what would it be?

Ryann Dowdy:

It’s not about you. Leadership is not about you. It’s about serving other people. Leadership is, to me, it’s actually one of the most selfless things that we have to do. Right? It’s right up there with parenting. We have to put people ahead of ourselves and not in an unhealthy way. Right? This is not I’m becoming a martyr or any of that. I’m not proposing that, but it’s I’ve had a really crappy day. Right? Say for instance, I have a small child who didn’t sleep last night. I’m the leader of an organization, but somebody comes in and they had a crappy day and their kid didn’t sleep last night and their dog peed on the floor and their kid was late to school and all the other things. I have to put my stuff away and be present for that person. That to me is what leadership is about.

Craig P Anderson:

Leadership is a terrible privilege, and people who want that title just to say I’m a leader are not going to be good at the job.

Ryann Dowdy:

It’s the same as entrepreneurship. It sounds really sexy in Facebook ads. It’s not.

Craig P Anderson:

No. I actually say I work harder now than I ever did. At least in corporate America, I have my weekends kind of blocked a little bit. Entrepreneurship is great. Nobody tells you what to do, but you’re leading yourself, and it’s a different world. Well, this has been great. So, Ryann, people who want to connect with you or learn more about the things that you’re doing, what are the best ways for them to get in touch with you?

Ryann Dowdy:

To learn more about Be in the Room, it’s beintheroom.org is to Be in the Room community, and that’s for female leaders. If you want to learn more about the Self Leadership Principles and what I do with sales teams, it’s uncensoredconsulting.com. On social media. I am Ryann with two Ns Dowdy. I’m an open networker. I love to talk to people. So, feel free to send a connection request, send a dm. I just like to network and talk to smart people.

Craig P Anderson:

Fantastic. And hopefully through all your good work with female leaders, we will start getting some great books written by female leaders for everybody to read.

Ryann Dowdy:

Right, so everybody can have a leadership crush. That’s all.

Craig P Anderson:

As always here on The Accidental Leader Podcast, I like to leave you with three key takeaways from our interviews, and I like to frame them in the key leadership areas of confidence, competence, and calm. So, here’s what I took away from our conversation with Ryann Dowdy today. Around the idea of confidence, she said self-trust is so crucial. How can your team trust you if you don’t trust yourself? Developing that self-trust in ourselves and believing in ourselves is what leads to confidence in our leadership style.

Secondary, she touched on around competence. She said there’s no cookie cutter way to lead humans. Leadership is something we learn and it evolves for us over time. There are wrong ways to lead, but there are different approaches that are going to be more effective with different peoples and teams that you have. So, remember, your competence comes from that ability to read the room and know that there’s no cookie-cutter way to lead humans. And then finally, around calm, and I love this idea that remembering that leadership is not all about you. When we focus everything inward as a leader on how it impacts us, that’s going to raise our anxiety. It’s going to raise our stress level. So, by keeping that sense of humility, realizing it’s not about us, that’s going to allow us to have a more calm demeanor as we lead our teams and our organizations. Great interview today. I hope all of you enjoyed it.

Are you an accidental leader looking to level up? A great place to start is by leading better team meetings. If you’d like help with that, go to clearpathcoaches.com/bettermeetings to download my 10 rules for better meetings. Your team will thank you, and you will feel a lot more confidence, competence, and calm in your next leadership team meeting. Thanks for listening today, and remember that leaders aren’t born, they’re made. You can go from accidental leader to the greatest of all time leader. It just takes confidence, competence, and calm. We’ll see you next time.