Leadership Lessons from a NYC Tour Guide

S6 Ep2: Jackie and Courtney share leadership lessons from an unexpected teacher.

Courtney: Welcome to Slingshots25’s Shotcast, a series of bite-sized podcasts that’ll feel like an espresso shot to your brain. I’m Courtney.

Jackie: Oh, I’m Jackie.

Courtney: Something we’ve been thinking about is a trip. This is a very special episode.

Jackie: It is

Courtney: Because we don’t normally do vacation sharing, but today we’re going to talk about a trip that we took to New York City, and the best part of our trip to New York City was.
Our tour guide.

Jackie: Steve. We love Steve.

Courtney: Steve was just like the highlight. And so, a little shout-out to the Sydneys. We took my daughter and Jackie’s niece to New York, and we met Steve, and he took us around New York City, and he has, we took this trip a while ago, and we’re still quoting Steve, and we felt it was time to share some of Steve’s leadership lessons with y’all.
So that’s what we’re going to do. Um, Steve from Queens, here’s the first we get on a tour bus. The first thing he says as he’s introducing himself, he says, I’m from Queens. I got a lawnmower and an above ground pool. And right off the bat, he gives us a very important leadership lesson, which is. Let people know what they can expect from you.
You start to talk, get a vibe for Steve, right off the bat.
Jackie: We did. I’m not sure what vibe I was supposed to get from the above-ground pool and the lawnmower and queens, but somehow, it was important.

Jackie: I still got it. Even though I don’t, you know, I’ve never been to Queens. I really don’t know what to make of that, but somehow, I still managed to get Steve’s vibe.

Courtney: Yep.

Jackie: I love it. So, as leaders, we should be thinking about what your version of “my name is Steve, I’m from Queens” is. I have an above-ground pool and a lawnmower. Like what is your version of that

Courtney: and how often leaders skip that step? There’s like, we do a ton of executive coaching and very rarely is there not a point where we talk about, and we’ve talked about accountability and expectations on the podcast lately, let people know.
About you share your philosophy, share your history, share your values. It’s important.

Jackie: Yeah. Yeah. I love that. And because who you are and your values, um, you know, say something, say a lot about you. So, I, I’m going to skip to the lesson that Steve gave us about, uh, standing on your values. So, here’s, uh, I’ll have to, I have to set the scene.
So, we’re standing in Central Park. And there is, um, what, what do you, uh, what do you call that? Where there’s just like a, a guitar player and they’re just singing and they’ve got their guitar thing acoustic? No, no, no, no. I’m talking about like, it’s, it’s, there’s, there’s a term for this just like hanging out in the park and playing your guitar and hoping people give you money. Okay. There’s a word for that. I don’t know what it is.

Courtney: Unemployment,

Jackie: Actually, they probably make a lot more than I do. We’re standing there and we’re across the street from the place where, um, John Lennon lived and died. Um, so, you know, and John Lennon, you know, sang about peace and, and joy and love.
Um, and so. So, Steve is listening to this person, you know, sing about peace while playing their guitar in Central Park, and he says, I’ve never seen so many people sing about peace while fighting over a few square feet of concrete. Apparently, this is a really prime spot to play guitar. Uh, in, in Central Park.
And I’m not kidding when I say I am pretty sure they probably make more there in a day than I make in a year. Um, so, you know, that’s hilarious. Um, and true. Uh, but it, it makes us think about, there’s a leadership lesson in that is do you stand on your values if you are going to sing about peace? Are you about peace?
If you are going to, if you are going to hang a poster on the wall that says we’re all about people speaking up and, and sharing their ideas, do you stand on that? Do you allow people to speak up and share their ideas, or do you shut people down and, and just really pursue your own ideas? So, you know, as, as they might say in the south, are you all hat no cattle?
Um, do you really stand on your values? And I think that’s important as leaders that we are constantly staying aligned in that space.

Courtney: I love it. I love it. Uh, probably the things that we quote the most from Steve a couple times, he said things like, and there’s what, probably 50 people on this tour. Yeah.
He’d say to us, hurry up. But take your time. Yes. Or he had water getting in, off, off and on the bus. Help yourself, but don’t be greedy. And there’s probably a hundred other ones, but the, you know, the constant giving of advice to this team was paradoxical. Two different ideas at the same time. And there’s a very important leadership lesson here that like, first of all, leadership is a series of tradeoffs, but also.
How often as leaders, we are faced with challenges where there actually are two things true at the same time.

Courtney: And it’s recognizing that our brains don’t like to say, take your time, but hurry up. Mm-hmm. Like, which one do you want from me? Pick. Right. It just, it’s so almost cause us to suffer, to have to think about two different things at once.
But as leaders, we do it all the time. We have to do very personal work.

Courtney: And not take it personally. We have to do hard things and trust ourselves and be scared while we do them. It’s just like I could go on and on and on with examples of two different ideas at the same time. And I think really good leaders can hold space for the paradox, for the difference.
And I think to be a good leader, you need to stay curious and practice, pay attention to where you’re falling into it. You know, your own judgment, your judgment’s becoming a truth, you’re being inflexible because there’s probably another version of that story, and both things might be true, and what would that change about what you’re doing and how you’re responding?
Jackie: I love that of just having to learn how to live in that nuance. Without giving in to your desire to create clarity where clarity should not necessarily be created, you know, help yourself, but don’t be greedy. Yeah. Both are true. Both are true. And you’ll, you’ll get employees that want to try to back you into a corner of what, which one do

Jackie: Yeah. To remove the nuance. It’s really hard. It’s, it, it’s an incredibly hard space to stand. Um, but really important. And Steve got it just right. Um, let’s see. The last one I think we’ve got from Steve that, um, we don’t, we don’t say this a lot, but we thought it was really a clever leadership idea, which is walk fast and don’t make eye contact.
Now remember, we’re in New York City, so I guess that’s supposed to mean something. I think people just got to, you know, like walk fast, don’t make eye contact. That sounds like how you should live in New York City. But specifically, we were, we, he was teaching us. I’m not even sure if we should tell people we did this.
Um, he was teaching us how to cut the line, the Stanton Island Ferry. And, you know, he’s, he’s been doing this a long time. He knows he’s got to keep his people together and he knows he is got to get ’em all on the same ferry and he knows that we’re on a schedule and all these sorts of things. And there’s just, I don’t know, like 4 million people standing in this lobby it seemed like.
And so, he takes us around the, the, you know, the edge of the, of the room. And, and he doesn’t, you know, he knows that we know. We’re cutting the line and maybe a little uncomfortable with that. So, the whole way, he’s like, walk fast, don’t make eye contact, walk fast. Don’t make eye contact.

Courtney: Walk like a New Yorker.

Jackie: There you go. So, I think we can snatch a leadership lesson out of that. Um, even though that was maybe cheating the system a little, but it’s, you know, we see this as like, sometimes you have to ignore the crowd and move with purpose to achieve something of value. It’s not always about asking everyone. For their advice and their feedback.
Like sometimes you’ve got to get a direction and go with it. You don’t want to do that often. And you want to be aware of what you’re doing it, and you want to maybe take some others along with you. Um, but you know, it’s not always, again, I think this kind of takes us back to the place of there’s some nuance in leadership that we sometimes don’t appreciate.

Courtney: Yeah, it’s super fun. Really fun remembering old Steve. Um, all right. Anything else you want to say about this? I don’t think so. Well, I’m going to say check out TripAdvisor. Look for Steve. Great bus tour. And while we’re recommending ourselves, we’ll recommend him. And then I’m going to say that’s all for this episode of our shot cast, but we always have much more to say.
If you want more, drop us a line at Slingshot25.com. Until next time.

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