From childhood anxieties to executive leadership with Kyler Mason, part 2

Every leader eventually comes to a decision point. At some point you have to choose, am I gonna let this thing win or am I going to take control of it and become the leader I want to be? For Tiffany, that thing was fear. We heard her go through her fear journey and face her fear head on. For me, that thing is anxiety, and for many years I thought there was no way out until I had a choice to make.

I'm Kyler Mason and this is my takeover of scared confidence. For me, anxiety feels like, uh, really, like I kinda lose my breath. There's like a, especially in public speaking or performance anxiety, like run out of air. I have like tightness in my chest and my brain goes blank. So, uh, I, I can't really communicate the things that I'm, that I'm intending to or that I, that I wished I would.

I have like, what I would call like our two types of anxiety. Like I will be, I'll be like stressed and I'll have like a steady hum sometimes that, that like comes and goes. Then there's like performance anxiety and um, that's, that's anything where I, where I am in my mind on a stage and I could be on a stage in front of three people or the whole company and, um, they produce a similar feeling and type of anxiety.

Uh, and it doesn't have to be a. Like a big thing. Like we have every quarter a, a meeting with our director team to, to prepare for the upcoming quarter, talk about new priorities, things like that. And it's a small group of people that I consider my friends and like in a very comfortable, safe environment.

I, I get up and talk at that every time. Um, one of the times I remember in particular, I was just like frozen cause I just like said to everyone. I was like, I don't even know what I was supposed to say. And then I ended up getting through it and probably did like okay. Um, and then I, after that was like, [00:02:00] this is ridiculous that I'm in this position and I have to deal with this.

I remember that one particular being one where I was just like a 10 out of 10, disappointed, you know, I think in the first, I don't know how many years, many years. Probably five. I had no sense that that was a thing for him. And I don't think I really probably had a real sense that that was a thing for people.

I don't have anxiety, and it's not something in my family's like dna. Like my parents didn't have anxiety. My siblings don't have anxiety, my husband doesn't. So the people I'm really, really close to, I hadn't seen it play out in a way that. Took up such mental capacity, like really like, man, you gotta like wrestle with this.

So I think the first five years I had no idea. And then he had an episode where he went to the hospital. I came out of an executive meeting one day and [00:03:00] just went and sat at my desk and started just, I was like feeling dizzy and I knew. Deep down I was fine. I was like dizzy. My chest was tight. I was like super sweaty and I was like, this is not normal.

So I just packed my shit up and drove to the hospital. Um, called my mom on the way. I was like, Hey, I'm going to the hospital. Nothing's wrong that I know of, but I'm just kind of freaking out. The only way that he described it to me, cause it's hard to know, I mean, I. I have anxiety, but it's a totally different type of anxiety, I think, than what he struggles with.

But the only way that he has been able to describe it to me is he was like, I, I felt like I was gonna die. Like I, I really felt like I was gonna die. Um, and so that was, that was really scary for me because, I mean, how do you hope besides just getting him there and, um, kind of just stepping back and saying like, I'm here when you, when you need me, or [00:04:00] I'm here for whatever.

But yeah, that was really scary is him just feeling so out of control and like he couldn't deal with it, that he really thought that he was not gonna make it. I went in just like a ton of people do that I've actually learned since then. They go to the hospital with a panic attack and they're completely fine.

And I remember at the ER and just got lucky with a really great nurse. He came in and. He's like, what's going on? Tell me what's happening in your life. And I was like, well, I just got a new position in the company with like a lot of different responsibilities that things I'm thinking about a lot. I'm getting married.

Just moved. He was like, well, that's why you're in here. I was like, oh, okay. Um, pretty much was like, you're fine. You're just going through, you're going through a lot. I definitely feel like that encouraged him to talk about it more. Especially with me. I had to. Create that space where I respected, okay, [00:05:00] maybe you need a little time.

Come to me when you're ready. Or maybe you don't wanna talk about it at all. So, yeah, but I do feel like that helped him to be like, all right, I gotta deal with this somehow. Um, and he is not someone that wants to immediately jump to like taking a medication or things like that. I said, I said, you know what, I respect that.

Like, whatever you feel comfortable with, but you've gotta do something. You can't, we can't just keep going, um, without you talking about it with someone, whether it's me, whether it's someone outside of our family, uh, whatever that looks like, we've gotta figure out something that's gonna work for you.

I've had the advantage or disadvantage of being surrounded by, um, Tiffany in particular and seeing the leader that she is incredibly articulate. Um, very motivating. She's a magnet for, for people that are, um, you know, high achievers and stuff like that, and charismatic, like all the [00:06:00] stuff, the things that you would think about.

Um, and like, I'm, I'm just. Not going to be that same kind of leader. So that's probably been a source of like, there's a big gap that I need to fill. And I'm not that like a big part of the discussion in addition to being president, was becoming an owner at elementary. And I very distinctly remember, I don't remember how long ago this was, but this was like early on in the process I said, Tiffany, if I were you, I would not let me be the president or an owner until I get this like anxiety thing figured out.

I was like, I wouldn't, I think that would be a bad decision. I definitely remember when Kyler came to me and said, I think that you should really think hard about having me be president if I can't get this anxiety thing under control. I remember. Like exactly where I was sitting, it was in my office. I remember it very well.[00:07:00]

Um, and my response was really to just say, I, like, I hear you. I didn't react like in any kind of way. I, I think because in some ways I wasn't sure how to respond. I, I think I realized in that moment, we all have a thing, like we all have a thing. Our things have different names, and his thing is anxiety.

And I had to watch whether or not he wanted to keep working on it. And if he did, then we were gonna be fine. If he was gonna surrender. What I knew he wanted to have happened in his life to this thing, there was no amount of like Tiffany giving him a personal pep rally that was gonna change what was gonna happen if he wasn't ready.

To like really lean into it, and I think it was in that moment he revealed to me [00:08:00] the size of it for him. I think it was in that moment that he realized he had a choice to make. I don't actually know what she thought about that when I said that, but I do remember she had said sometime later like that also something along the lines of, Hey, this the anxiety you have like.

You're performing regardless of it. And that's, that's pretty f pretty helpful to hear. I had spent quite a bit of time with other senior leaders, executive leaders at that point in my career, and I, I, I just knew there's a lot of people that struggle with this and I. Getting him some exposure to those people, I think began to normalize it for him.

That was one of the first things that I did to say like, you're not broken. This isn't something you can't do. Um, you will find your toolbox and there is a real. Gift to the world if you accomplish this and have anxiety because you are like one more data point that proves this doesn't have to [00:09:00] take control of your life.

And I'd been through my fear journey and some of those, some of the names of the things that controlled me and I think that, you know, he had a choice to make. My name is Wes and uh, I am Kyle's executive coach. I've been as a coach for two years now. We were introduced through a mutual friend, and, uh, I was looking for new clients at the time, and I had mentioned to this person that I was looking for somebody who was experiencing an inflection point in the business that they were a part of.

And so KY came to mind for this individual and, and Ky and I had an initial conversation. And, um, we were, um, kind of off to the races with starting a coaching relationship at that point. So I would say early on, In our coaching relationship. Some of the things that I recall about Kyler that I think has still been consistent even to this day was one was just how thoughtful [00:10:00] of a person that he is.

And what I mean by that is he's very deliberate with his thoughts. So he will actually, whenever I prompt a question, um, he will sort of slow down and dig really deep. You can tell he's digging really deep to get to what is the sincere, earnest answer that he wants to give. Um, and so he puts, um, a lot of thought into the thoughts that he is, um, offering in whatever context that is.

It's actually been something that I've started to adopt. I've been kind of inspired by the way that he does that, and so I'll take time to slow down. Um, and be more thoughtful with some of the questions. So part of my process is I will interview a bunch of people that work closely with my clients and, um, try to understand what are their strengths and what are their weaknesses as a leader.

And one of the things as part of that process that I heard again and again and again, was that there was such a high level of trust between Kyler and those that work with him. And I think he had trouble accepting the [00:11:00] bedrock that he had established. To that point. Like, and what I mean by that was I think he, there was a lot of self-doubt there around like, um, am I the one for the job?

Do I have enough trust with everybody? Uh, and he took that very seriously, maybe so much so to his own detriment. And what I mean by that is I think he just needed to believe that he had the foundation of trust that he needed in order to do the job that he. Has been called to do. And so in many regards, it was just believing what was already in existence and just stepping into that with a greater degree of confidence.

And that's sort of the arc that I've seen over the course of our coaching relationship is him step into that confidence in greater and greater measure over time. I think that there was also an expectation that he had, that he needed to be a certain kind of leader. And so comparing himself to a certain kind of leader rather than just accepting the kind of leader [00:12:00] that he is and leaning authentically in to his own version of leadership.

So I have to really think about like, what are the things that I think are, um, important to me and the things that I would want to follow if I were following me. And that's like just a part of my core values, like, Being genuine. Trust is a big deal to me. Um, I believe that the, the way you're building trust is by being transparent with, uh, the people around you.

I, I really want to help people get what they want out of their careers and things like that. So I just have had to move away from wanting to be, or thinking I should be this like leader that can, can perform and like be charismatic and rather I. Figure out what it is that I am and have the DNA for am trying to be.

What makes up a good leader is do I trust you as a leader to take us and the people that I'm working alongside into [00:13:00] some. Unknown future. And even as that future becomes more and more known as we move towards it is do I believe that I am going to be appreciated, cared for, challenged, all sorts of things on our way there.

So trust, I think is the foundation. And then I also think clarity is a foundation. As well is what direction are we going in? And even if the clarity in that moment is, I'm not sure where we're going right now, but we're gonna figure it out. That is still clarity. Um, I think alignment is another thing is, um, are your interests and what you care about and where you personally are wanting to go, does that align with the mission that we've set out for ourselves?

And I think that trust, alignment, clarity, and there's, you know, any number of things that can make up a leader, but I think that those are some really bedrock things. I think those can take any number of expression. I think that it can look different for a lot of different people in the way that they are providing clarity.

I think that it can look different in the [00:14:00] way that we build trust with one another. And I think that I can look different in the way that I hear about what your interests are in the direction that you are wanting to go in, and the level of creativity that we might deploy for that to fold within a mission.

I'm still trying to process the like relationship I have with it. I would in no way say I've gotten to a place where I can manage it successfully. Uh, I think I'm a lot better than where I was, but I would say that. The chatter I might have in my head from my dad would be, um, something that would present itself, like, make this decision and, and like stick with it and grow through it.

Now, I, I always know like, just do the hard thing. You'll be better at the end of it. And I like to think that through each of these hard things, uh, or decisions I've made to take on new, different heavier roles, it's, it's been good for me. Tiffany and I talked about this [00:15:00] recently actually. Um, and I need to go, I need to like go from disappointed in myself and embarrassed about it to, I need to learn how to better manage it and develop systems and tools to, um, to just get more comfortable with the fact that it's probably here to stay.

Um, maybe one day it won't be, but I. I can't keep getting like mad at myself after any time I have performance anxiety and then don't articulate the things that I want to as well as I want to. And then go through this vicious, like unproductive thinking loop about I should have done better. I didn't do that well.

And the people that were around me are probably questioning how is this guy even the president when he is dealing with this? Those are very real and normal thoughts that I have. Um, that. I would say today versus even a year ago, I have that unproductive thinking loop a lot less often and working [00:16:00] on, all right, what am I gonna do to just deal with this?

Is this something that I can like grow through? Can I like do this? Am I willing to do this? Is I know that the, the stakes are going to get larger and my responsibilities are going to be more significant. So along will come the anxiety with it and. Am I like ready, willing, and able to handle all this.

That's been a, that's been a frustrating conversation to have with myself, to just also imagine like, if I didn't deal with this, I feel like things would be so much easier. I roll my eyes at saying that because everyone's got their things, everyone's battling something they're trying to grow through.

Mine is just anxiety. Next time on Scared, confident. I think the biggest thing for me is the work that I've done with Westgate. He's my coach. A lot of our work ended up centering around how do we have hard conversations. I think that the exploration of where does this come [00:17:00] from, in particular, the anxiety and the facing it head on actually made it worse for a while, which is very frustrating.

I am actually curious about like it got worse before it got better. Mm-hmm. Like what did you have to realize? Through that struggle that got you to a place of where it started to improve.

‍