The Leadership Shift Behind Every Great Team (w/ Ryan Leak)

So whether you're a solopreneur or you're managing a team, all of us fall into some form of leadership. We're working with other people, we're trying to get things done. And I don't know if you've ever felt this, but I think like a lot of us, you may have a team member that's drifting. Maybe people are showing up, getting work done, but somewhere along the way they're not putting in their best. You're noticing it. You're not sure how to get the best out of the people you work with. Because I know this, everybody in my network who's done something amazing, they didn't do it alone. They had great people. And so how do you develop great people? How do you retain great people? A lot of us are just leading on autopilot, and this will cap your growth because at some point Everything becomes a people problem. And that's the thing I've learned about leadership. And so for today's episode, this is a raw captured moment from our recent Forward event 2026. This was the VIP lunch where we sat down with one of the keynote speakers, Ryan Leak, and he broke down everything in about 15 minutes. I know you're going to get a ton of value out of this. Let's get into it. Ryan, bro, these people in this room are the leaders in the community, the Forward community. Maybe they're leading an individual small team like them and solopreneur vibes, but then some of us are actually leading teams. and different things like this. So, when it comes to leadership, what are the traits you're seeing like right now? 'Cause you're helping, if you don't know, Ryan coaches top leaders throughout the country and the Fortune 500 companies. What are the things that you're seeing that we could help this group with?

Yeah, that's a good question. I think, you know, sometimes leaders can get on autopilot and they can make the assumption that they know how their team is actually doing because they simply showed up to work, smiled, and did their job. But I think leaders are actually losing touch with how their people are actually doing. And so my next book is called Stay Culture and the Architecture of a Workplace People Never Want to Leave. And one of the things that we've discovered in research is that oftentimes when the right people leave, The leader didn't see it coming. They're like, wait, what? You weren't doing well? I mean, you were doing, you were performing well, but they're like, no, I'm actually making a shift. The other thing we see often is people will leave their jobs and not be honest about why.

Yeah.

You've left jobs before and you didn't, you weren't honest with your boss before. And so I think the leaders who can really get honest feedback, just because you say you can handle the truth does not mean you can handle the truth. you handling the truth is proven in your facial expressions, not in what you actually said back to them.

It's funny when you say that, 'cause I remember the same thing happened to me. Someone would be like, well, I didn't feel like that. Like, give me feedback, bro, what's going on? And then they would give you the feedback and it was very hard to take. Like, because you're like, well, wait a second, what about this? And what about this? And you immediately become defensive. And it took me a while to get to the point where like, You know what? Good point. I could have done better there. I'm sorry. You know, like, it's a blind spot for many of us who are just—

Totally.

In my mind, and maybe it's 'cause I have ADD, but also I think a lot of you guys would relate, in the entrepreneur's mind, in the salesman's mind, you have single focus. We're on a path to greatness. We're going, or we're on a path to fill this event, or we're on this new campaign. I'm just single focus, and I fail to see all the things outside of that vision. And my peripheral vision goes down.

Yeah, it's hard because you can't, the bigger your organization gets, you can't sit with every single person every single day. But I think the leaders who have these intentional checkpoints, not a yearly review, but a consistent check of the pulse of the culture, are the organizations where things don't drift because they're really in touch with There are people, a lot of people will hold on to, this is what you did last year. You're like, you haven't told me that in a year. Which, you know, everybody can get feedback. Not everybody can get honest feedback. And to get honest feedback, you have to be the kind of person who can really take it.

Yes, sir. So when you think about the part of leadership, which is the conversation right now, and specific for this room, I think that it's been a big help to me to lead from the front and not be able to check in with all the people and not be able to talk to people. But if I'm trying to lead a group of people through my personal brand, through the content, and I feel like it's been a huge unlock because I'm sharing my values, I'm sharing the things that are important, I'm sharing what the work we're doing and the work matters.

Yeah.

Like, I think letting people know The, like, even with this, our Forward team here, everybody on our squad, our work makes a difference.

Yeah.

It's not Neil's thing. It's like what we're doing, everybody here makes a difference. And I see, I see like—

Can I pause you? Can I pause you right there?

Please.

Can we just make some noise for the Forward team? Because like each and every, and this is a compliment to you, Each and every person I encounter, from security to sound person to— I'll even just tell you what just happened during the AV check. I said, hey, I'll do the AV check whenever you want. I'm here to serve you. They said, well, there's still people in the room. I said, I don't mind people seeing me. I mean, I'm here to speak. I mean, that's not a big deal. And one of the production managers said, yeah, but— I think we wanna save that moment for later.

Yeah.

He's thinking, Neel didn't tell him to do that. Like, it just shows you how much each person is caring about their portion of the business and of the event. And that's leadership. Like, you didn't know that. You didn't tell him to do that. Like, you didn't say, hey, we wanna save it for this moment. But he was thinking it. And we both went, you know what? You're right. Yeah. You know what? You're the expert. We'll follow you. You know? So kudos to you and your team, 'cause everybody here has This has been A1 for sure.

Thank you, bro. Yeah, clap it up one more time for the squad. The squad, the Forward Squad.

Yeah.

Um, and we did have— it's funny you say that because we had a conversation with the team yesterday about moments that matter, creating the moments, and all the moments combined. And that's why our event's full, and that's why the energy is good. So yeah, what do you think? What do you say to the person? Like, okay, if you don't necessarily say all the things, you don't appreciate all the people as much as you do, yes, you could do a better job, What can we do from a leadership, like, communication standpoint?

Yeah.

Like, to communicate at a high level so it all comes down and filters in and it does the work while you're sleeping?

Well, I think we are all always communicating our values all the time. You are always telling people what you care about the most by what you spend the most time on and what you talk about the most. So, you can either intentionally communicate your values or you will unintentionally communicate your values, but you are always communicating your values in some way, shape, or form. Most people default to unintentionally stating their values through the way that they email, through the things that they care about, through the things that they complain about, through the things that they celebrate, the things that they get excited about. Some people will get excited about a video going viral. That doesn't mean you sold anything, but, but, but now you just told the team, this is what they— care about. You communicated a value. You technically just had a meeting and told your whole team what's the most important thing to you, even though you didn't actually do that, but technically you just did. And so I think leaders who are intentional about communicating their values to be able to say, this is what is important to us, this is what matters to us, and is infusing that daily, weekly through social media, through their personal brand, I think are the leaders that, again, Because you can have a great culture on a Tuesday, but then you start to notice every single— one of our clients was the fastest-growing cybersecurity firm in the country at one point. And he said they were hiring, I think, like 60 people a week. And he said, our culture is literally under attack every single day. They literally had to hire one person and say, hey, we just cannot drift. So every time you bring in a new person, every time you onboard a new person, every time you hire a new vendor, think about it like that. Culture is under attack and it drifts really, really slowly unless you are absolutely intentional. The top brands in the world, they just have intentional cultures. I was talking to a buddy a couple days ago who fired his sister. I said, dude, you fired your sister? He goes, yeah, and she didn't even do anything wrong. I said, so why'd you fire her? He said, Well, because people were afraid to tell her the truth because we shared the same last name. And he said, I will do anything to protect the culture. That's intentionality. Some people just go, oh, you know, well, we, we could, we could talk through that. He says, he said, hey sis, love you. I think you will soar better in a place where intimidation isn't a part of your name, even though you didn't do anything wrong.

Dude, I love that.

Like being able to make those kinds of tough— and then The whole team pays attention to that move. They go, oh, he's, he is protecting the culture, which means I think I better protect the culture. I better send things up the ladder a little bit to say, hey, uh, here's a caution sign. Here's some things that I'm seeing. Like, because they know, oh, this matters to him so much that he'd fire his sister. I'm like, man, like, like that's going to get the attention of your team.

That would definitely do it for me too. I'd be in trouble. Yeah. That'd be crazy.

Yeah.

But I will say this, like, what— oh, I think this would be super helpful for everybody here, just to leave you guys with something actionable on this topic. Whether you have one assistant or whether you have somebody in this room has 100 people in their squad, and then I know somebody else in here is leading an entire company. Well, in those different variations, what is one thing actionable that could that we could do a better job to let this people, let everybody know the values? And I think some people might have like the company values and then check it out, maybe it's on a wall, maybe you haven't talked about it. But like, if you assume the person is active on social media, they're trying to communicate, they're building a personal brand, that's why we're all here. What is something we could do that would be actionable for the room?

I think, you know, a couple of things depending on the size of your team, obviously you're gonna have a touchpoint of some sort every single week. I think before you get down to business, I think writing down, hey, I wanna spend 5 minutes sharing a story of why our values matter, how we showed up for a client, how this story matters to our people in some way, shape, or form, because stories carry. And sometimes people can kind of get into the monotony of just doing the same old thing week in and week out and just going with the status quo. But I think for you to take 5 minutes of intentionality of that meeting, 5 minutes of intentionality of, you know, sometimes we have this thing when somebody does a good job and, and my video team shared this with me, you know, we do what, 150 to 200 pieces of content, of video content a year. And so I get sent a lot of links. Hey, Ryan, here's a video. Heart. You, it was good. I paid you to do the video. You did a very good job. If it was bad, I'd let you know. Heart. Next video. Like, I just kind of move on. And, and one of our videographers, he, he said, hey, can I, can I talk to you? I said, sure. You know, I, I, I'm very open to, to honest feedback. And, and he just goes, hey, uh, your feedback is underwhelming.

Yeah.

And I was like, you are so right. Like, it's just heart, heart, heart, heart, heart. Maybe a like, like thumbs up. Like, like, Maybe I'll do a, a, you know, okay emoji every now and then. He's just like, did you like when we used this B-roll? Did you like this song? And I just went, man, that, that's totally on me because I'm thinking I pay you, you do good work, move on. You know?

Bro, you're like, hey, the thank you was the check.

Yeah. You know? And some people think that way, like the thank you is the check. But, but when you can take just 5 minutes to just go, hey, I really appreciate the work that you're doing here. You know, like we've, I mean, we do a lot in the content space. We're building workbooks, we're working on 2 books right now. We've got a research thing going. I mean, we got so many different moving parts that I just, I can just be kind of short with my feedback and they're all doing really good. So I'm like, hey, it looks good to me. Hey, what'd you think about what we did with this chapter? Man, you did your job.

It's awesome.

Yeah. Yep. That's exactly what I said in the meeting. You took what I said and you put it in the book.

That's wonderful.

And I just, I can be underwhelming with my feedback. And so I actually had to start taking the beginning of my emails, you know, taking just a couple minutes on a phone call to go, hey, I just, hey man, not just watching the video. Like, I hope you know how good you really are. Like, this was amazing. You know, the shot of my Jordans going up the stairs, man. Like, I didn't even know you were sitting there. Were you under the stairs? Like, that's awesome.

You know?

Like, but sometimes people just need a reminder beyond the paycheck, beyond the direct deposit, that their work matters and that you see it. Your top performers, if you have some top performers, they don't just want a pat on the back, they wanna get better. They don't want to just stay with the status quo. They want, hey, good job here. Hey, actually, you wanna know what would take this to another level? If we, and then you fill in the blank with how they, how they can grow. And so I think it's, it really comes down to the word intentionality. The more intentional we are, whatever your communication method is going to be, whether you have a team huddle, whether it's on social media, whether it's an email, a phone call, a voice memo. Did, did you know a 1-minute voice memo could make somebody's whole year?

Yep.

Just a voice memo. Like, just record. Like, you don't even gotta call 'em. Like, sometimes you're like, oh, I don't have time to do this full-on conversation. Send them a 2-minute voicemail. They'll probably save it on their phone and play it at night before they go to bed. Like, it's one of those things about just being intentional.

Dude, I love that. And, you know, I think about even I'm in a leadership role, but then also I'm in other groups. And I just think about the way I feel when that group leader or somebody says, Dude, Neil, you guys know Neil? He's freaking killing it. And I'm like, bro, look at me. And I'm like, my chest goes up and I'm like, wow, that made me feel really good. So, if you're in a unique position in this room to have that power for somebody else, let's use it more often. Let's do a little more, that's all.

It's amazing. I checked into a Hyatt in Minneapolis about a month ago. I walked in and the lady at the front desk, she goes, Hello, Mr. Lee. We're glad you're here. I said, oh my God. How do you know my name? She goes, I checked you in the last time you were here. I said, oh my goodness. I called a VP at Hyatt. I speak for Hyatt. I said, dude, you won't believe what happened today. He goes, what? I go, she said my name. He's like, yeah, that sounds pretty basic. It's amazing how just saying somebody's name or just the smallest compliment just gives them a— dude, I travel to speak for a living. You know, but for some odd reason, this Hyatt worker just made me feel like a million bucks by calling me Mr. Leake. You know, it's like—

And what did it cost? Nothing.

Nothing.

Just a little time, a little bit of intentionality. So I hope you guys leave this conversation with just the one theme that I wanted to get out of this was just, let's just be more intentional with our communication. Also, we're not just talking about work. Let's be more intentional with the way we communicate with our families. family, like with your wife, your husband. How many times you don't tell your spouse that you appreciate them and you think it all the day and you never say it? And how many times would you appreciate if it's told to you? You know, like, what about the kids? Like, I was just showing Trev, my son posted this video that's badass, and he, he never posts videos because he's like scared to post them. And even though I'm his dad, you know, it shouldn't be like that. But yeah, um, he posted it and he was pumped about it, and I was like, I was razzing him up, I was like hyping him up about it. This is so dope. And I just think like we need to do more of that with everybody. So guys, clap it up for Ryan. Thank you.