Andy Freed: Author of Lead Like the Boss
Episode 820
On today’s episode, Kara welcomes Andy Freed, author of the new book Lead Like the Boss. With more than 30 years of experience leading organizations through growth and transformation, Andy has built his career around a powerful belief: communication isn’t just part of leadership — it is leadership. From coaching CEOs to guiding global coalitions — and serving as Chairman of the Board at Virtual, Inc. — Andy has seen firsthand that strategy succeeds or fails based on how well leaders communicate.
In Lead Like the Boss, Andy challenges leaders to rethink how they show up in moments that matter. Drawing inspiration from Bruce Springsteen concerts and decades of executive experience, he introduces practical tools like the “Think, Feel, Do” framework — three questions every leader should answer before any meeting, presentation, or major change initiative. The book reframes leadership as performance — not in a theatrical sense, but in the intentional preparation, sequencing, and presence that shape how messages land.
In this episode, Andy shares why leaders underestimate the communication risk of change, how different “flavors” of change require different messaging strategies, and why technology has made communication easier — but often less effective. We discuss the power of recognition, the importance of planning communication like a setlist, and how small, intentional interactions can dramatically shift engagement and alignment inside organizations. Whether you’re leading a company, managing a team, or simply trying to show up with more clarity and impact, this conversation offers actionable insight into how communication can elevate performance at every level. Don’t miss it!
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Transcript
Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be. I want to be you. Just want to make sure you will get knocked down. But just make sure you don’t get knocked out, knocked out. So your only choice should be go focus on what you can control. Control. Control. Hi everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs and really, some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hey, everyone, welcome back to the Kara Goldin show today. I’m joined by Andy fried, who is, in addition to a few other things, author of the brand new book, lead like a boss. And as I mentioned, Andy is a leader who has spent more than 30 years helping organizations grow, transform and align around a clear vision, and he believes something many leaders overlook, that communication isn’t just a skill, it’s the foundation. And whether he’s coaching CEOs or guiding global organizations, he is with his company. I should mention virtual Inc, he’s been firsthand, that’s he’s seen firsthand how that strategy works when leaders know how to inspire people so in lead, like the boss, which Andy wrote, recently launched. So good. I mean, I honestly not just because I’m a Bruce. Bruce Springsteen, huge fan. He shares the principal frameworks, including, think, feel, do, so I cannot wait to hear him explain a lot more about that whole concept and how to inspire alignment. All these things, whether you are part of an organization or leading an organization, are super important to be able to do so. Andy, welcome to the Kara Goldin show. So nice to meet you, too.
Andy Freed 2:16
Thanks for having me. Kara, great to be here,
Kara Goldin 2:19
absolutely so for listeners who are not aware yet, because it just launched Lead Like the Boss, how do you describe the core idea behind the book? Sure.
Andy Freed 2:31
So I’m one of these people who is this close to selling everything I own and just following Bruce Springsteen in the East Street band around the world. I’ve seen Bruce 95 times live. You know, traveled to Europe, traveled all over the place, you know, to the West Coast, East Coast, all over the world to see Bruce live and enjoy it every time, somewhere along the way, I started learning something and not just being entertained. I started watching the way that Bruce interacted with his band, I started to watch the way he interacted with the audience, and realized that there’s a reason they call him the boss, because he’s acting that way on stage, and he’s taking charge of things, and he’s, you know, bring a lot of forethought to it. So about four or five years ago, I was coming home from a concert, and to justify my trip, wrote a LinkedIn post about what I had learned at the show, and that kind of morphed into this book Lead Like the Boss, which talks which kind of follows the arc of a Springsteen concert to give lessons on communications and lessons on that every leader can take away, whether you’re on stage with 20,000 people or talking to one person in your audience. I think there’s common lessons you can take away from it.
Kara Goldin 3:45
So what do you think most leaders get wrong on this, on this concept?
Andy Freed 3:50
I think the key piece is intention. I think that communication has become so easy. Look, look, you and I are talking. You’re out on the other side of the country, and I clicked a button, and then there you were on my screen. Or if I need to present, it’s really easy to just open PowerPoint and start I’ll take last month’s slides, change the change the title, and start making them this month’s slides for a staff meeting. It’s gotten too easy to communicate, so we’ve lost the intentionality of coming up with our message, thinking about our performance when we’re talking to people, understanding what our audience’s needs are, all of that’s gotten lost. So I think the biggest problem we have is that, you know, it’s very easy to say, I need to present, present to my staff. I’m just going to be up there. And, you know, that’s the equivalent of Bruce just getting on stage and starting to play and hoping for the best. And that’s not how it goes.
Kara Goldin 4:48
Well, he’s such an amazing storyteller, too. So it’s, I mean, he’s really he has this engagement, and he clearly understands who his audience is. Yes, too. So when, when you started thinking about why it was that you that what made him so engaging to you? How long did it take before you decided this is my book?
Andy Freed 5:17
Not long, because I thought it was such a great example. And when I started to just kind of delve deeper into the things he does from start to finish, it just made sense. So, as an example, one of the things I opened the book with is talking about how a Bruce show doesn’t start when he takes the stage. You know, Bruce show starts hours before, when he’s sitting backstage and with a pen and paper, and it’s always just a blank sheet of white paper and a pen, he sits and he writes out the set list for the show, and that set list is kind of his guide of what the audience will think, feel and do during the show. But as he does that, there’s a lot of forethought of the stories he wants to tell of you know, one thing I know from reading about Bruce is he likes to open the show really big, because he’s got anxiety and depression. And he said, If I open the show and give everyone their money’s worth in the first five minutes, now I can relax, you know. So he likes to open the show big. Then there might be a moment where he wants to take it down and tell a story, as he said, because he’s a great storyteller, then there’s a moment where he wants the audience to participate. All of that has a lot of forethought, and all of that is going through a script before he even starts playing. For me, that’s the difference between opening PowerPoint and cranking out slides and sitting down and thinking about, what do I might want an audience to think, feel and do. So that was the first lesson that I took away, and as I started going deeper, there’s just more and more along the way that are great parallels for how every leader can communicate.
Kara Goldin 6:55
So you just mentioned it, but think, feel, do when leaders are planning out a message, this message, their message, and a presentation with, think, feel, do. Can you think of an example in your practice where it was just night and day at one of your clients was able to use this? I mean, I
Andy Freed 7:21
can think of examples from clients. I can think of examples also from, you know, just internally on the company, and just, you know, internal things that we do. For me, the the whole idea of think, feel, do is it’s a three legged stool, and you need all three. You need to think about, what do you want your audience to think? How do you want them to feel, and what do you want them to do with the end of the end of a conversation, you know? So it could be as simple as something like, if I’m talking to my company about changing the health care plan, on one hand, I want them to understand what the plan is and think that it’s a good option. But if I don’t address the feeling side, that for people, this is highly personal that you know, it’s their health care. If they’re worried about are they going to have to change doctors? Is it going to cost more? Is my kid going to be able to get the meds that they need? All of those things are part of the fuel side of it, and unless you address that, they’re never going to be ready to hear the think part. And then at the end, it’s making it explicit. Well, what am I supposed to do now? And so often the CEO will present, and then the action step is unclear, and people leave the room doing all different things, and they’re not aligned, you know. So it doesn’t take a big, you know, kind of apocryphal change, changing the world message, for this construct to work. It’s about having the forethought and intention to really think about all three.
Kara Goldin 8:47
So you talk about timing and order, and a little bit you talked about in the set list that that Bruce and I think it’s a great example. But if you don’t have the timing in the order correct, I guess. Why does that matter so much?
Andy Freed 9:04
Yeah, it’s really easy to lose people, and it’s really easy to start to talk to people before they’re ready to listen, before they’re ready to hear you. I think that the mistake that a lot of leaders make when they’re communicating is they’re so worried about what they’re going to what they want to say, that they forget about what the audience needs to hear. And if you don’t get that timing and order right, of addressing things right off the bat, addressing people’s fears right off the bat, and that’s often a big part of it, of and recognizing that, if you’re a leader, communicating with an audience, sometimes there’s fear. But what’s he going to say? Is this going to be the announcement of the layoffs? Is this going to be the announcements of restructuring, or is the company doing okay? So sometimes it’s about having that timing and order of understanding that first I need to make people feel safe, you know. And Simon Sinek, once you know, that’s Simon Sinek, famous TED talk. Um. Is great leaders make people feel safe. And between Simon Sinek and me, we’ve sold millions of books together. So he might have a slight edge on me. It’s somewhere in my combined total of Super Bowl rings with Tom Brady, together, we’ve done really well, but the idea that you need to make somebody feel safe before you can deliver that message is, I think, something that’s so important, and if you’re not doing that, things can get misconstrued.
Kara Goldin 10:33
So and So, how do you do that? If the message is that you just need to show up to, like in the case of Bruce, he’s not necessarily making people feel safe when he goes out on stage. He’s really there to entertain and to, you know, story tell and do these things. But what is there? Is there room for people if they know that, you know things are going well, or people are there to entertain. I mean, what are those different? I guess forums where people might need to be showing up at leading like the boss,
Andy Freed 11:12
you know? So I’ll start with, you know, for Bruce, it’s more than just entertaining like so if you look at his new his new tour is the no kings, land of hope and dreams tour, you know. So it’s got a clear political bent, and he’s willing to use his voice towards that, but he’s trying to have people feel empowered and feel that there’s something that can be done if you feel that things aren’t going in the right direction. So there’s a clear element to how he’s feeling on this and his last show, his last tour was all about kind of his mortality as the last man standing from the first band he was ever in. So it was kind of a feel that went with that. I think just about any message that you’re delivering has some element of that. Do you want your audience to feel that, you know, back to the health care do I want them to feel that I care about this as much as they do? You know, that’s the thing I want them to come away with. You know, if it’s, you know, some of the other messages we have with organizations might be more technical. And, you know, we work with a lot of technical groups that are doing things like cybersecurity, with cybersecurity and various, various internet functions. But when you’re working with those groups, it’s also about, well, what do I want somebody to feel? I want them to feel that this, what’s this technology gonna let me do? So the idea behind, for example, like mobile payment and the idea of paying for things with your cell phone. Well, I want to feel that I can now travel the world with just my phone and like I can feel more energized and I can feel more independent, you know, because something’s out there that works as safe and interoperable. So I want to feel that that technology is safe. I want to feel that that technology is ubiquitous. You know, that’s different than just the facts. And then the do is, well, you should be using it, you know. So you can use that, you know, that example, in any number of places.
Kara Goldin 13:12
So we’re all living in at least a hybrid environment, many totally virtual environments. What do you think technology? You know, it’s definitely made communications easier, but it’s often worse. And what do you think it is that we could change there in our leadership practice?
Andy Freed 13:38
A few things. One, I think, on the Zoom calls, and the teams calls, and all the things that we’re doing. Again, I’ll go back to the whole idea of intention, and, you know, intention and preparation. So one is understanding the call isn’t just about the content, it’s about the relationships, and that’s what you’re trying to build. So sometimes the five minutes before the call, when you’re talking about just how your weekend was and all of that. We lost that with Zoom and teams, you know, we got very transactional. And we went from going to conference rooms, where it was natural to have some small talk as you were getting together, to just everyone dials in at three o’clock, and then everyone clicks end at the end, and you don’t know anybody you know. So I think one thing that would be building, you know, that look to build in is the trust and relationships that come from building those kind of side conversations that, in my mind, are anything but side conversations. They’re central because they’re how you build trust. The other piece, I’ll say, is just preparation. You know the number of zoom and teams calls that I’m still on, and we’re now six years past the start of pandemic. For God’s sakes, everyone should know where the mute button is on zoom by now. And you should know that if you’re going to be on a important meeting, maybe. Be, you should be reasonably well lit. You should be in a place where people should he can hear you. You shouldn’t have the dogs bursting in. You know, I’ll tell you that I’ve been to 95 Ruth shows, and I’ve been able to hear them every single time because they care, and they know that’s part of the job is, lights have to work, sound has to work. There’s a light check and a sound check before there’s no reason that leaders can’t have that, and they’re that’s part of your bag of tricks now, in a remote environment, is make it work and make it work well, because if people can’t hear you, they’re definitely not listening.
Kara Goldin 15:32
Yeah, definitely. I couldn’t agree more. And I think it’s, it’s it it’s, you know, definitely something that people have gotten much better about, but it’s there’s it’s still missing in many people’s life,
Andy Freed 15:50
and it’s also understanding that the technology can only get you so far. You know, there is a time that you need to meet somebody face to face and connect in a different way. You know, just the notion that eye contact is impossible on Zoom and teams, eye contact is such a key part of communication, and you cannot look at the camera and look at the person’s eyes at the same time hard as you try, you know. So you know, just things like that are missing and different from how we’re communicating.
Kara Goldin 16:21
Now, I loved your point about acknowledgement as well, how that’s such a leadership lever. I couldn’t agree more. I have a four kids, but one of my kids is just recently, just a little over a year ago, started at rivian, and they have these team virtual calls, and his manager is constantly calling him and other people on the team out on different things that they’ve that they’ve done, done mostly done well. But he also, you know, talks about he does the bad with the good, and when you do the good, then I think people don’t feel shamed, right, that they don’t think he’s a jerk. They think he’s authentic, and he just wants everybody to be a little bit better. But why is that so important in your mind, to be able to do that?
Andy Freed 17:21
No, I mean, it’s more than 100 years ago. William James, who was the father of American psychiatry, wrote that the deepest human need is the need to be appreciated. And that’s worth kind of stopping on the deepest human need is the need to be appreciated that. So that means that, like a deeper need than money, a deeper need than sex, a deeper need than than anything, is that need to be appreciated, that people just feel that you know the you’re appreciated for what you do. So one of my favorite moments of every Bruce show is at the very end of the show, when you know the you know the music’s basically done. Bruce retreats to the back of the stage and he shakes the hand and gives a hug and whispers something the ear of every member of the band as they file off the stage. And in this last tour, he was playing with 19 people on stage, and every one of them, whether it was Gary W talent that he’s been playing with since 1973 or some of the folks who were in the horn section who he just started playing with on this tour, every one of them would get something that, you know, handshake and something that he would say to them every single night. And when you hear them talk about it, I heard them interviewed on George Stephanopoulos show. They said was what the band members say is for 10 seconds every night. Bruce Springsteen makes me feel like the most important musician on the face of the earth. Like imagine that being your mantra as a CEO, that you’re going to make your team feel like the most important team on the face of the earth. How much more do you get out of them for that? How much are they willing to go the extra mile, and how much does it also go to not taking it for granted that whether you’ve been playing with this person for 53 years or playing with them for 53 days, you’re still going to acknowledge and show them that appreciation and how much that can matter to them. They say that the task of a leader is to make more leaders. That’s how you do it is to start showing that kind of appreciation and start building people up. And I love how Bruce does that. It’s something which I think every leader should be very conscious and
Kara Goldin 19:32
intentional on. When you were writing Lead Like the Boss Did anything surprise you as you were really digging into this concept. Obviously, you’ve seen him over 9095, times, and you have you are very familiar with the show, even though it changes along the way. But was there anything that was kind of surprising in his leadership that. You picked up on, I mean, I
Andy Freed 20:01
think one thing that surprised me, and there’s some things that I don’t really use as well, and then you wouldn’t associate it with a rock star. And one thing that Bruce uses well is silence from time to time. You know, there are time when he just quiets to cry it down, and you can hear a pin drop in an arena and that, you know, that’s when he’s making a point. Or, you know, there’s a point where he’s in the song 10th Avenue freeze out, and he says, you know, now, here’s the important part. And he’s quiet for a moment before, you know, the changers made uptown, the big band joined the band. That use of silence is something I’m terrible at. I need to fill the white space all the time. And you know, if there is an awkward silence. I’m talking over it and trying to, you know, to kind of go with it. So the power of that is something which you wouldn’t expect to look at a rock star and think about the power of silence and the power of listening, but I think that those are things that are just so powerful. And what he does that I can add more to my bag of tricks. And, you know, all of us is developing, you know, are developing as leaders, and all of us are developing every day.
Kara Goldin 21:05
So one thing that the next time somebody’s walking into a room and really trying to Lead Like the Boss, what, what would you say is, is the takeaway that you want everyone to grab hold of, just from from the book, but
Andy Freed 21:24
just in life. Yeah, I think it’s the intention of understanding what your audience needs. And also, there’s an element of it, you know, if you look at Bruce, you know, so much of Bruce’s music is about factory workers and blue collar workers. Bruce is anything but that he’s never worked a day in his life in a factory. He’s never, didn’t go to Vietnam, but Born in the USA, is one of the great protest songs about the Vietnam War that comes also from, instead of trying so hard to be interesting, try to be interested. And when you hear Bruce tell it’s like he learned about Vietnam from talking to Ron Kovic, and he learned about factory workers from talking to his dad and talking to other folks along the way. That idea as a leader, that it’s not your job necessarily be the most interesting person in the room, but sometimes to be the most interested person in the room can really transform your leadership and transform your communications, and means that you’re going to build those relationships with people that you can fall back on, and that can get people to the next level, because you’re sincerely interested in them and who they are as a people, and what they are, what you’re all trying to do together, and what their needs are in talking to you.
Kara Goldin 22:41
Andy, I love it. I love the analogy. Lead Like the Boss is terrific. Everyone needs to pick up a copy of it. Gift it to your team. The work that you’ve done is is so powerful and such a great reminder on intentional communications, for sure, reframing leadership as performance, especially with somebody as awesome as Bruce is, is is brilliant. So for everyone listening, be sure to check out Lead Like the Boss and follow along with Andy on social channels as well. Thank you Andy for coming on and thank you everyone for listening, Kara. Thanks for having me. It’s been a lot of fun. Thanks again for listening to the Kara Goldin show. If you would please give us a review and feel free to share this podcast with others who would benefit. And of course, feel free to subscribe so you don’t miss a single episode of our podcast. Just a reminder that I can be found on all platforms at Kara Goldin, I would love to hear from you, too. So feel free to DM me, and if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book, undaunted, where I share more about my journey, including founding and building hint, we are here every Monday, Wednesday and Friday. Thanks for listening, and goodbye for now.
