Why Leaders Break Trust Without Realizing It | Michael Eskenasy, Founder of ChefreyOS

In this episode of The Leadership Match with Martin Rowinski, Martin sits down with Michael Eskenasy, Founder of ChefreyOS, for a quick leadership conversation about trust, context, accountability, communication, and what leaders often miss when pressure starts building inside a company.

Michael shares why the people around you may not be experiencing the same reality you are in the moment, and why great leaders need to understand where people are before pushing a message. If someone is not ready to receive the message, forcing it can create more confusion, panic, and fracture.

The conversation also explores:

- Why trust is one of the most important leadership assets
- How unclear roles and expectations create stress inside teams
- Why leaders need to explain the pressure behind decisions
- How accountability and personal responsibility changed Michael’s career
- Lessons from working with companies including Disney, Twilio, and Amazon
- Why impact can matter more than money or status
- Michael’s lesson from In "Search of Greatness" and Wayne Gretzky’s mindset

If you are a founder, CEO, executive, entrepreneur, project leader, or business owner trying to build stronger trust, communicate better under pressure, and lead with more accountability, this episode is for you.

The Leadership Match with Martin Rowinski is built around quick conversations that connect leaders with better ideas, better people, and better action.

Subscribe for more leadership conversations, founder insights, executive lessons, and practical action steps.

#Leadership #Trust #Accountability #TheLeadershipMatch #MartinRowinski #MichaelEskenasy #ChefreyOS #FounderAdvice #StartupLeadership #BusinessLeadership #ExecutiveLeadership #LeadershipDevelopment #Communication #FounderMindset #PersonalResponsibility #CompanyCulture #Entrepreneurship #ImpactDriven #LeadershipLessons #BusinessGrowth #TrustBuilding #LeadershipCommunication

Transcript

SPEAKER_00 0:00

Welcome back to the Leadership Match. In the next few minutes, we're going to uncover one idea, one lesson, and one action that can help leaders grow. These are real conversations, practical insight, and action you can use. Today I'm joined by Michael Eskenezzi. Did I say it right that time? You did. I mean you're getting you're getting closer, and that's all that matters. It's progress. It's okay. As long as we're making progress, that's awesome. I'm there. All right, let's jump into this. Um, what is one leadership lesson you believe more people need to hear right now?

SPEAKER_01 0:42

I would say that that the people who are around you don't have the same perception of reality that you do in that moment. So you need to understand where everybody is and make sure the message is designed for that specific person in that specific moment. Because if they're not available to take the message, you need to find a way to preserve it for the time that they are. Because if you continue to push on someone who doesn't understand, you're just creating more fracture, more panic, more everything. Get give them the minute, like, hey, let's not solve this unless it's brain surgery, let it go and come back to it.

SPEAKER_00 1:21

Yeah, no need to confuse them even more, right? That's exactly it. Um, what is an idea, belief, or strategy that changed the way that you lead?

SPEAKER_01 1:38

That trust is is probably the most important thing. Um I understand part of the problem is that nobody under nobody is able to really trust their situation in any given time. So if we're gonna if we're gonna pull words together, I think that's the way that I would do it on the fly, which is if if people are working within a a business and they know the business is always looking to cut corners, cut costs, find ways to to bring things down. And then people who are project managers are just like, hey, I'm a project manager, but now I need to become an accountant for this for this job, you're now stretching people in ways that they don't understand that they're not able to do, creating roles that never existed because of gaps. So if that's something that is happening to someone, then that is that is going to leave them unaware to be able to fill that job in any way, and their ability to communicate and step out of the loop is gonna become impossible because all those weird contextual fibers that hold that role together are now gone. And then when somebody leaves, you got to rebuild it in a different way. So so for me it's it's maintaining that context.

SPEAKER_00 2:53

Awesome. Now, a little personal, who helped shape your leadership journey and what did they see in you that maybe you did not see in yourself yet?

SPEAKER_01 3:06

That's a wild, that's a wild story in itself. It started with it started with a like I don't know how deep you want me to get into this, but the craziest experience I ever had is I was I was 26, uh 20, 25 or 26, right? And I was in a position where I wasn't making much money. I didn't have, you know, I I was not life was not people say, hey man, this is this is great times, and like noob's not great times. Um and I was not happy with where my life went. So a weird twist of events happened, and I saw, and I um ended up taking something that was illegal at the time um in in the state of California, but is now very much uh appreciated in some of those states. Um and I took a little bit too much. And what happened was is the abstractions that I was never able to put together and the fragmentations in that moment seemed to disappear. So I was listening, my buddy was like, hey, dude, listen to this Adam Corolla podcast. This guy's hilarious. So I'm like, okay, cool. So I listened to it, and and I like this was like the second time I'm like, okay, this was awesome. I need to try this. And then I flipped this guy on, and he was talking about like, hey, get off your ass, go to school, do these things. And I'm like, I'm like having because I'm I'm new to this, right? So I'm like having this moment where I'm like, oh my God, he's talking to me. So so five days later, I enrolled in college, got my bachelor's degree, bachelor's degree, MBA, started at Disney a month after I graduated, and we were off. So I was like, okay, dude, this guy sees the light. So I was like listening to him. And what's interesting about him is his stances have haven't changed in like the 30 years that he's been doing radio. Politics have shifted shifted around it. But it was all about personal responsibility, all about accountability, all about those things. And I'm like, I'm in this moment and I hear this, and I'm like, okay, this is now became a core value that was already somewhat instilled in me, but now it just became uh the catalyst for everything that started.

SPEAKER_00 5:28

That's awesome. Yeah, and and you went on from Disney to other great companies, including Twilio and Amazon, right?

SPEAKER_01 5:36

That that's exactly right. And it was, it was just it was never because of technical skill. It was always about accountability. And, you know, if I was gonna get fired, I was gonna get fired, but I was gonna be honest with whatever whoever that individual was, and being that buffer between political situations is is what allowed my career to do anything.

SPEAKER_00 5:55

That's awesome. What is one action leaders can take this week to get better results?

SPEAKER_01 6:03

Acknowledge their mistakes. Acknowledge, and and it's not it's not mistakes, it's almost more of social pressures. It's it's people go the the VP, and I always go to the VP level because I think it's the most understandable from every front line. Like everyone kind of deals with a VP in some way, shape, or form. So so the VP is now getting pressure from whoever is putting pressure on this. We need numbers, we need this, we got to hit whatever it is, it's fine. But people don't know where that's coming from. And it's kind of like when your mom says to you, because I said so, it's like, now I can't draw boundaries. Because you've said that, I now don't understand what is okay because there's no logic behind it. So as that trickles down and people don't understand, people are happy to do it for you. They care about you. Um, they want, they want to deliver for you. But if they don't understand what's driving that, then they're gonna draw their own conclusions and they're gonna start drifting in the wrong direction, and you're never gonna get where you need to go. If you're honest with them, you're just like, dude, this is the reality that we live in, it's gonna clear a lot of things up and build trust.

SPEAKER_00 7:10

Awesome. I love that answer. When you look at leadership today, where do you see the biggest mismatch between people, roles, and expectations?

SPEAKER_01 7:21

People's roles. So when you talk about, when you talk about it, right, it it really starts at the at the uh level, right? You got let's look at someone who's in HR. Someone in HR, what they're doing, right, is they're they're really marketing. And what they're what they're marketing is they're marketing a deal, a brokerage deal between you and a human being. You give me your cognitive ability, and I will give you this life that I promise. Here's your insurance, here's this, here's this. Your family's gonna love it, kids are protected, uh, your kid needs some dental work, covered, you know, all that stuff is then presented to you in exchange for your cognitive. So, so now there's a deal that's happening, and you get in there and you're now catching up, and you gotta be agile, which means we don't know what we're doing. So you gotta, you gotta jump on the fly. You have to. Um, I had I had a bunch of examples of these that I've actually I actually wrote and and started thinking about, but it's like all those all those cultural words meet mean so like be an owner, which is like you're the one who's gonna get slapped when this goes wrong. It's all those things mean something, and they're not clear about what those mean and the ambiguity that comes with them. So everyone's left to their own devices to figure out how do I survive in this role. And because of that, everyone's expectations of what you need and what I need to be successful, like you may need this project to go, but I need this to stay under budget. So now we're battling over this thing, and it's not that we don't get along and that we don't like each other, it's that I gotta feed my family, you gotta feed my family, and these people are pitting us against each other to create the best result in our stress. So I would say that's probably where I'd lean into.

SPEAKER_00 9:10

Got it. And what is a mistake or a hard lesson that made you a better leader?

SPEAKER_01 9:17

Probably the realization was so, so, so let me let me take you through this. So I got this dog Sheffy, which is what I named, I named the business after because he he's he's my ride or die. So so Sheffri, uh, we got him. He was a puppy. Um I was working in um I was this was this was during the pandemic. I was working for True Pill. I got a they gave me a sweet offer. My wife um my at the time was starting our starting our bakery. Um so she was off doing that, but the but the money was there. And then all of a sudden, when the pandemic started pulling back um on that, you know, kind of money and funding that was going out for the companies like Twilio that were growing as a result of everyone going digital, um, and that crashed, then they looked at me and they were like, dude, you're expensive. And I'm like, I got it. I'm gonna I'm gonna help myself out the door. So I got laid off and I had to start working in the bakery with my wife. Not had to, I really wanted to. I was done. I was done. I wanted to go. So we went there, but the problem was is we had this, we had this four, five, six-month-old puppy at the time. Uh uh, you know, he's a he's a burnadoodle, a big big boy. Destroyed the place. So just just destroyed it. So then when we were, we were in San Francisco, so we started looking at um at the actual numbers that were going out. We're like, okay, I'm not making, I'm not making bullshit tech money anymore. I'm now, you know, we gotta, we gotta, we gotta hunker down. So we actually our stuff, our place was trashed. Um, everything was done up. So we're like, why go buy a let's go live in a van? We got a bakery, we got everything, let's just throw a bed in the van and let's go live in it. So we built this van. We built this van. We had this this Mercedes, like, not like the huge ones, but like a sprinter. And and my wife parked around the corner and she opened the door, and this car came around and hit the open door so hard that it shifted the van off its frame the night before we were gonna move into it. So now we don't have a place. So we're using like like hotel like points to get into a place until we could figure out like, okay, what do we do? And what we ended up doing is living in a U-Haul that we rented by the day and had to pay for parking and had to do that while we were working. And all we had was literally me, my wife, um, my dog, and my dog. It was like, it was that that was the unit. And and we were in San Francisco living in San Francisco, and edit this part out, it was enough for me, and that's where I really found out, so I can say that again for you. Um, not her. And that's that's you know, something that you realize, which is you need to align with people all across the way. I was happy being there with my family, and because of that, it changed my ability to what I find is important to me. And one of the things that isn't specifically important to me is money. And because I'm in this position, it means I can do a lot of things because that number, that status, doesn't drive me. I would rather help people with it, and it's gonna be a it's gonna be a fun ride because of that.

SPEAKER_00 12:40

Yeah, you're you're driven by impact.

SPEAKER_01 12:44

Yeah, it and that's and that's and that's where we are. So it's just about banging the drum and hitting it because, like I said, I have no marketing budget, but the result of that, which is gonna be amazing, is going to be because I have no marketing budget and people see the quality in which that comes with um my system and everything else, that that badge now becomes a marketing tool on its own for everybody else who's using the system and standing up to that level of of discipline and respect and um and all those other things I probably just misclassified.

SPEAKER_00 13:17

What is, and this is a final match question. What is one book person habit or just an idea that you would match with every leader listening?

SPEAKER_01 13:29

Oh, I quote this all the time. So there's this movie, it's called In Search of Greatness, if you've seen it. And it's where Wayne Gretzky, where he's like, hey, dude, I was sitting there, and he's like, and he's like doing the mapping with the puck and watching it, and then they're like, Wayne, who who who pushed you to train, who did this? He's like, nobody. And that answer is is the key, and it's the the thing that I'm running on, which is I'm doing my way in Gretzky. Like, like this is my version of doing what I want to do unbounded. No one's pushing me to do this. Imagine if everybody could do that. Imagine if everybody could remove the administrative and coordinative ability off their lives and put 120% into whatever they want to do. Imagine what we can create, and that's that's what it's all about. And and that that quote by uh when Wayne Gretzky said that, it was uh it was everything for me.

SPEAKER_00 14:26

Awesome. I gotta I gotta re-watch that one. All right, leadership is built one conversation, one connection, and one action at a time. Thanks for listening to the leadership match. I'm your host, Martin Ravinsky. And if this conversation gave you one idea to act on, subscribe, share it with another leader, and I'll see you in the next match. Thanks, Michael. Thank you.