Getting Out of Your Own Way: Overcoming Self-Doubt as a Leader

Dr. Jim: [: 00:00:00

That's what Stephanie Kitron realized early on in her career when she was on her leadership journey, and she's going to join us today and walk us through all of the discoveries that she had. And how that impacted her leadership journey and her team building journey when she was building an elite team.

So let me give you a little background about Stephanie's story. She's the creative force behind talent development at Westgate Resorts for the last almost six years. She's got the energy of a kid at Disneyland and a strategic mind of a seasoned leader. She's transformed the workplace into a hub of innovation and growth.

the most, world's most well [: 00:01:00

she's taken a lot of pride in creating lasting, positive change, propelling team members to new heights of effectiveness, performance, and satisfaction. She has a team of trainers that she leads and she challenges her trainers to think outside of their box and focus on

engaging the cohorts that are going through the programming. She encourages building interactive learning experiences that empower team members to reach for the stars in her work. She puts an emphasis on integrating both work and play with the pursuit of empowering everybody to reach their potential stephanie kitron. Welcome to the show

Stephanie Ketron: Thanks for having me.

Dr. Jim: Now I know that we covered a lot of stuff on the bio, but I think before we dive into the conversation, it's going to be helpful for our listeners to hear some additional context about the about your background and story so that we're better informed about the perspective that you bring to the table.

was in my early twenties in [: 00:02:00

Really propelled my career. And then from there I moved on and worked for Applebee's. I was actually, I was a bartender at Applebee's. And I like to always joke a little bit about that. I went from slinging drinks to training people and bringing games and interactive into the learning environment, but I got that from really having that enjoyment with my guests, as I was serving them at Applebee's, but I got my start in training there really. And that's where I've ventured off instead of just doing leadership, I got into the training world and started to become a trainer. I was a corporate trainer. And then from there have continued to grow.

nce I had dual role, where I [: 00:03:00

to be able to help create content and create learning experiences for new leaders. And then I got the ability to join the Westgate team right in a great time. They were actually starting a learning and development team. So I have been a part of this team from the ground up since it started about six years ago.

And I've been able to help mold and shape that team

Dr. Jim: one of the things that you left out and I actually left out in the intro is that you're a reservist and you worked in the signal support team, and you've also been in retail.

eavily about empowerment and [: 00:04:00

That's not normally what I would think about. Given a retail environment. So tell us about how your experience as a reservist and more importantly, as somebody in retail shifted or shaped that empowerment focus

Stephanie Ketron: as soon as you say that it comes to mind about going to drill weekends and that top down approach, because it very much is a top down approach. And I was very young, so I was a little bit rebellious at that time when I was in the reservist and, I really didn't like that approach and I didn't always see eye to eye with my squad leader because I did not like that approach so much.

And as you can imagine, I was having conversations with their superior often to say, Hey, listen, you can't do this,. This is life or death. I think it's a little bit more serious in that field,. Where we have to do things by the book in a certain way. I think it just brought in a different perspective for me to be able to see that I do know that there's a time and a place where you got to be serious, .

s we have to get done. But I [: 00:05:00

As I mentioned, I got my start pretty young in leadership, and so I was leading people that were very close in age with me. And I would say all still young in experience. We're all going to college, so we're all learning along the way. But sometimes that can be a downfall to having a young leader leading also a young team.

But I think it helped me make better connections with people. And it was in that moment in retail that I realized that if I was able to make connections with people, it made leading them a lot easier because I knew things about them. And I knew if they were having a bad day, I could see it on their face.

hem better. And I think it's [: 00:06:00

And I tend to think I'm a good people leader because of that.

Dr. Jim: When you think about your almost six years of time at Westgate, what's the accomplishment that you're most proud of during your time there?

Stephanie Ketron: I think the accomplishment that I'm most proud of in the last six years at Westgate is being able to see where we started and where we are now. As I mentioned, this team was new to Westgate five and a half years ago, and when I first joined the team at early on as one of the first couple people that joined the team I don't think that we had a lot of buy in just because a company had been around for many years and we were new, .

And so one of my biggest accomplishments now is being able to take a look back over the last five and a half, six years and see where we started and where we're at now and look at the different. Accomplishments that we have been able to do and all the people that reach out to us and really want support from our team and want us to facilitate sessions for their leaders and facilitate sessions for our executive leaders.

[: 00:07:00

Dr. Jim: That's a pretty big transformation. And I think if I'm looking at the timeline of of your time there, you've also been able to accomplish that transformation through a pandemic. So those are two things, especially Yeah, a resort environment is highly customer facing. So you probably had to navigate all of that sort of stuff during the shutdowns and all that.

So there's a lot of context there that we're probably leaving out in the conversation. What sort of the biggest moon shot that you have on your radar that you want to get done?

Stephanie Ketron: The next thing that I really want to accomplish in our organization is we have multiple layers and multiple levels of training across the entire company. I get the privilege of helping out in resort operations and corporate operations, but we also have a sell side of our business. And we help a little bit in our call centers and different.

ut I'd really like to see for: 2024

Dr. Jim: I want to close the loop a little bit most teams fail to become elite because the members of the team have no clear understanding about the nature of the work that they're doing.

So how does that tie in with your experience and your leadership journey in terms of the game changing realization that you had that really shifted your perspective on how great teams are built?

Stephanie Ketron: So I think what kind of happened to me about a year ago is again, I've been with the department, since it started, but I got the opportunity to lead a function of the department that I hadn't led in the past. I'd worked very closely with them. They are the instructional design team and I've always worked very closely with them.

ople leader. So I thought by [: 00:09:00

And I think my realization was once I started leading that team, I made great connections with them, but I struggled in some of the areas as far as understanding the work that they do day in and day out. Not being able to work in some of the systems that they work in day in and day out, not being able to troubleshoot some of those challenges that they're having.

And so I think I had to take a step back and say, am I leading them effectively? Yes, they like me yes, we're working well together. Yes, I'm project managing, but is that all leadership is? And that's not all leadership is. I really needed to understand the work that they were doing and get a clear grasp in it so that I could actually help them move forward and move through some things.

you did to bridge those gaps [: 00:10:00

Stephanie Ketron: Yeah, so they work with certain platforms such as storyline and rise. I had dabbled in rise before I'd done a couple things in that software, but I'd never worked in storyline before. And so I started asking questions. I started asking, why does this take so long or why isn't this functioning the way we want it to function?

And I think that was able to help me start to build closer relationships to some of them and break down some of those walls because then I was able to, they felt more comfortable coming to me with some of those challenges. I also took it upon myself to seek out information about this software, start to do my own research about it.

I started attending webinars about it, making connections with other leaders that work in the learning and development field and really starting to network and find leaders that No, that very well. And I reached out to a past colleague and that actually has experience in instructional design.

And I said, Hey, walk me [: 00:11:00

Does that same strategy work for this team? And I think leaning on that mentor and just learning I think, we can, we have to continue to learn to grow and really taking the opportunities to learn has helped me be a better leader to that function.

Dr. Jim: I like the emphasis that you've put on digging in, understanding the technology, understanding the workflows, building out your network and diving deep into that area. But there's a risk in doing that. And, the risk oftentimes like early stage managers, one of the reasons they commonly fail is because they jump right back into the work.

are supposed to do. So their [: 00:12:00

Stephanie Ketron: I think I just continued to have conversations with them and understand the projects that they were taking on. And I continued to stop myself at the point of the project that I would have always owned. So the front end of the project, approving budgets for the project, just doing a quick overview of the project to better understand what direction they're moving in.

And I continue as a leader to offer solutions, but. Allow them to determined kind of the solution in the direction in which we move. They are the experts in the work that they do. And so I lean still heavily on them to. Help get to a final answer.

It's never, Hey, this is just what we're going to do. This is the final answer and go for it. I'm always like, what solutions do you have? Or what things do you think we can do to enhance this? Or how do you think we get to the end goal here? And then continue to work through that with them.

Dr. Jim: I [: 00:13:00

So I think that's important for for listeners to pay attention to. If you feel yourself starting to do the thing. Instead of coaching to the thing that's a that's an important distinction to keep in mind so that can be pretty tricky to navigate and I think one of the pieces of context that you mentioned about that transition was that.

You'd already been a people leader before, but you were a people leader in a space that you were familiar with, that you quote unquote grew up in, and then you move to a different area of the business where you had less familiarity. I'd imagine you ran into some potential questions of credibility from the team.

avigate that process as well?[: 00:14:00

Stephanie Ketron: I had an upper hand a little bit, because I've worked on the broader team for so long that each of them knew me as an individual and they knew me as a leader for the overall team. And I had relationships with them individually prior to that. But one thing I did very early on is I.

Provided full transparency, . If they would ask me a question that I didn't know the answer to, instead of trying to just sugarcoat it, or instead of trying to act as if I knew the answer I would just honestly say, listen, I'm not a hundred percent sure on this answer, I think it's probably best for us one, two, maybe let's research it together and let's see if we can come to the conclusion or let's also lean on others we're very blessed that our VP has a strong background and comes from that side of kind of the learning and development field.

shop it and we'll get on the [: 00:15:00

Again, I think my transparency upfront with them was a good thing. And then I think just working through it with them together, not always saying, Hey, this is the answer. And this is the direction we have to go. I

Dr. Jim: The collaborative approach that you took as well as the transparent approach that you took is probably a good general principle for any leader. Depending on what generation you're in, you're brainwashed into thinking that you got to fake it till you make it. I think there's no better way to ruin your credibility than to try to do that.

So you don't know what you don't know and be okay with it. You are where you are. So I think that's really good that you took that approach. Now you're roughly a year and a half into this pivot. If somebody else is thinking about or in the process of making a similar move in their career and they want to do some of the things that you've done, what are the red flags that they need to watch out for?

g to make this pivot, have a [: 00:16:00

Stephanie Ketron: would say not not let yourself get in your own way. I think that's there's a saying something along the lines there, but don't get in your own way. Don't get in your own head. I went in very nervous about it. How am I going to lead this team? How am I going to make sure they're successful?

Oh, they operate me. Very differently than I've used to leading. So I think that's the first one is really just making sure that you're not in your own head that you have the confidence to go in and take on leading a new function. And I would just be mindful of. Do people start to pull away?

that they were getting prior [: 00:17:00

Dr. Jim: There's a couple of interesting things about those questions that you ask. You mentioned, staying out of your own head. You mentioned, how is, how will I lead? How do the people that report into me like to be led?

What was their experience in being led before? How did you bridge those gaps and establish a foundation to to pivot from or jump off from to what you wanted to do? What were those early steps that you took to reduce that friction?

Stephanie Ketron: As I mentioned previously I sought out a mentor, and I think that was very important. And then I sought out continuous leadership from my leader as well. Tell me what I can do. Tell me how I can be successful.

designers is I instilled to [: 00:18:00

Now I have a one on one every week with them for a half an hour. That's their time. We can talk about whatever they want. We have a project update. So yes, we can talk about projects. We can talk about updates during that, but it's also their time just to throw out ideas to me and me bounce ideas off of them about what I'm thinking and talk about the future and talk about their growth and their development and different things like that.

Dr. Jim: When we're talking about building a foundation for success, especially when it comes to a couple of things that we've talked about throughout the conversation we talked about, not having a clear understanding of what. Each role involves. And then the second element of it is, how do you create the space to have the conversations that you need to have?

that you have a multilayered [: 00:19:00

That helps foster transparency. The reason why what you just mentioned stands out to me is that I talked to a lot of people leaders and oftentimes they've mentioned a disconnect at the manager level between. Line managers and individual contributors and being able to connect the dots in terms of how the work fits into the bigger picture.

If you're not building a foundation of communication, like what you just described across all layers of the organization, you're going to struggle in connecting those dots to the people that report into you. So I really like how you brought all of that together.

Stephanie, this has been a really strong conversation. I had a lot of fun chatting about your leadership journey. I think when we look at the overarching theme of the conversation, which is really understanding the nature of the work that each member of the team is doing.

et started. What are the big [: 00:20:00

Stephanie Ketron: I think to start laying the groundwork and start having conversations, right? Just have those conversations. Go and talk to your team members. Get a better understanding of what they feel like they're supposed to be doing. And then you need to also, as a leader, understand what's the overall big picture for the organization.

What's your expectation of that person? Is there alignment with your expectation? What they feel they should be doing? And if there's not alignment, then maybe having another conversation with your direct leader or that person that's making those decisions to sit to say, what is the expectation? Where do we go from here? What does this person really need to be doing? And then again, having just having those conversations with them to find out what is it that you're doing or what is that you think you're supposed to be doing?

vel setting there. What else [: 00:21:00

Stephanie Ketron: I think really just seeking out others that know and understand the role and that you also trust and you can start having some of those conversations with, . It's not always easy to say, I don't know. I don't know what I don't know. Or, hey, can you help me? I think it's really hard sometimes for us to ask for help.

And so really seeking out someone that you trust in that Seeking out someone that's a trusted mentor, a trusted friend and asking them for support and seeing what they know and really just going out and learning all that there is to learn. The Internet's at our fingertips, and there's so many things that you can find and so many resources that you could use, and there's always free resources, too.

I think a lot of times people feel a little. Bit shy to go and ask for money to go to conferences or do this or do that. But there's so many free resources out there that you can utilize that can help you.

Dr. Jim: If people want to continue the conversation, what's the best way for them to get in touch with you?

Stephanie Ketron: They can connect with me through LinkedIn.

Dr. Jim: Really great [: 00:22:00

But when I sit back and think about the conversation that we had and the things that stood out to me, I think one of the things that you mentioned early on in the conversation should be something that every leader has on their radar. And you mentioned early on in the conversation that you thought you were a good people leader based on your experience in your previous roles, and then you made a pivot and you weren't quite sure. That's a realization or a level of self awareness that a lot of leaders need to carry with them in any new role. Just because you were successful in a previous position, some of those fundamentals. Might not work in your new position. So you need to make sure that you're focused on the core things that got you to excellence in your [00:23:00] previous role.

And those core things tend to be pretty much the same across the board. If you're not laying a foundation of open communication and transparency and asking a lot of questions of the people that report into you, About where they're at, what they're doing, what's getting in the way you're setting yourself up to go in a wrong direction because you're going to be operating with a lot of assumptions that might not be true.

So that's the big thing that stood out or a big element that stood out in the conversation that you and I had. I appreciate you mapping that out, but I wanted to take some time to call that out for those who have been listening to the conversation.

If you liked the conversation leave us a review, tell us tell us what stood out for you, and then tune in next time where we'll have another great leader sharing with us their game changing realization that really helped them build a high performing team.