Stranger 32, Day 32 – Meet Kyle, the “New Leader”

Stranger 32, Day 32 - Meet Kyle

I met today’s Stranger at actually a customer I am selling to. How great is that? He’s one of the new sales leadership in a growth-stage startup doing very well here in Atlanta. Going to dive right into our “meet”.

Meet Kyle, 34

Who are you?

“That’s a really broad question…” I tell him that’s the beauty of the question.

“I am a son, a brother, a sales guy… a sales leader, former football player and baseball player, surfer, skier, passionate about my religion.”

What are your passions? What are your dreams, if you have any?

“So passions would begin with…,” he thinks. “… winning… or rather, not losing. And helping others do the same, right? So help others get better — I’m pretty passionate about. I’m passionate about what we’re doing here” at his company. “From a technology standpoint, very passionate about SaaS, in general. From personal, very passionate about reading, family, and my faith.” He thinks more.

“Surfing, skiing, seeing things, traveling, sports… all those things.”

I was once asked from a sales respective, “Do you love winning more than you hate losing?”

“I hate losing… if I had to pick one, it would be, ‘I hate losing’.”

What’s a Life Lesson you’d like to share based on some of things things you’ve done?

“A life lesson? Hmm…” He thinks about this again. “This is a deep interview.” We both laugh. He appreciates these questions beyond the superficial stuff.

“Life lesson I’ve learned from something in my past… is that change is inevitable, so you should learn how to embrace it.”

Kyle talks about how he’s lived through being in a startup that was acquired by “a large fish” that was later acquired by a “much larger fish”. He shares how life constantly changes, and how great things have occurred by embracing these changes.

Have you had a Life-Defining Moment?

“Life-Defining? Still waiting for one,” he laughs.

“I’ve had a lot of Life-Defining Moments.” I asked him for just one that has brought him to this moment.

“Moving from an individual contributor and a leader without a title to an actual leadership role,” Kyle explained — this occurred a couple months ago.

“It was a change. It was a decision I made to say this was the path I wanted to pursue because I loved what I was doing.”

What’s one of the biggest challenges you’re facing now as a leader?

“There’s going to be many challenges. I think it’s just going to be… Time management’s always a tough thing, especially when you have more people depending on you. They’re all challenges I enjoy. There’s a lot of things I’m trying to get down.” I think Kyle was also thinking about what things could be in the future in terms of responsibilities and how challenges will be much bigger.

Kyle continues with another big challenge, “having less control. As an individual contributor, you can 100% make your sales number. You can find a way to get there. And when you’re a leader, you can do the same, but you’re also very reliant on the people who are rolling up to you, and who you’re serving as a leader. So how do you inspire them to have that same drive to get there?”

“It’s a different way… you have less direct control, and you have more indirect control.”

“… can’t control your income as much, right? As an individual contributor, you have a lot more control.” Here, Kyle was referring to commission-based sales reps and being a leader who is dependent on the output of many.

I asked Kyle how he’s able to be both confident and vulnerable as a leader now. I asked him if he found himself needing to be more vulnerable as a leader.

“Yeah, I think that being transparent and vulnerable… both are keys to leadership. You need to be approachable and someone they can relate to. Everyone’s vulnerable. You just might not show it. There’s something about you that you wish you could change, or something you’re not great at, or you might be great at, but you know you messed up… Most leaders that I’ve ever worked for have had that space. But they were also very confident in the direction they’re in, and they realize the best ideas come from the group vs. just your one way of thinking.”

“At the end of the day, you’re the one who has say, ‘yeah, we’re going to do this.'”

“And you have to have confidence in that, and you have to convey the why behind it. If you can convey the why and have confidence, you can influence people to do it.”

Who would you like to meet with — what person in history would you want to sit and talk to, and then, what would be the number one question you would want to ask? (Thanks to Kellie, Stranger 31)

“So many people…” he ponders. “Depends on how far back… Jesus would be one.”

“For me… Martin Luther King Jr. would be a great one.” I ask him what would a question be that he would ask. There would probably be too many questions for Jesus.

“How did you do it?” I was curious…

“I feel like I know why he did. I’d probably confirm those things — social injustice. How did he overcome all of the adversity he faced. How did you do that? How did you influence all those people? It’s fascinating. The why is obviously what you want to know why — probably a good place to dip in there, too, but I feel there’s pretty good knowledge among every person that knows who Dr. Martin Luther King Jr. was, and why he did what he did. Really the how…”

What question would you like to ask tomorrow’s Stranger?

“What did yesterday teach you?”

After the handshake.

During my interview with Kyle, I got a strong sense of confidence from him. He’s buttoned-up, confident, and speaks well. He’s really adapting to life as a sales leader, and I could tell that he was enjoying the challenge.

I also enjoyed asking him some more thoughtful questions to which he realized, too. Thinking about my role at the startup I’m at and a recent recruiting career fair, I’m very cognizant of who we interview and hire. I’m interested in knowing deeper habits and motivations of the sales and marketing candidates because we want to build a company with a great culture.

So meet Kyle. No longer a Stranger.

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