Bet on People with Al Dea

In this episode of the Bet on People Podcast, Keegan Evans, executive coach and AI Consultant at Euda and Limited Partner at Beyond Earth Ventures, sits down with Al Dea, Keynote Speaker, Advisor and Founder & CEO of The Edge of Work. They explore the principles of human-centered leadership, emphasizing how investing in people drives both individual growth and organizational success. Al shares insights from his career spanning Deloitte, Salesforce, and founding The Edge of Work, discussing how leaders can navigate change, develop trust, and maximize potential in their teams.

Expect to Learn:

• How human-centered leadership principles apply in a changing, AI-influenced workplace.
• The role of feedback, curiosity, and empathy in developing high-performing teams.
• Strategies for spotting and nurturing talent even amid systemic and structural challenges.
• Lessons from early leadership experiences that shaped Al’s approach to trust and people development.
• How to balance competence, warmth, and relational trust as a leader.

Episode Breakdown with Timestamps

[00:00:00] – Teaser
[00:01:22] – Introduction: Keegan welcomes Al Dea and highlights his background in consulting and leadership thought leadership.
[00:04:43] – Navigating Change: Al explains the concept of the “liminal space” and how leaders face uncertainty in transitional periods.
[00:08:16] – Foundational Leadership Lessons: Al shares an early career example of prioritizing comfort over giving constructive feedback and the lessons learned.
[00:15:56] – Coaching Through Feedback: The importance of two-way feedback conversations and curiosity to support growth in employees.
[00:18:46] – Recognizing Potential Amid Structural Challenges: How Al helped a high-performing team member find the right role to fully realize her potential.
[00:28:34] – Early Leadership Experience: Managing a caddy program at age 14–15, learning empathy, context, and understanding before acting.
[00:35:37] – Advice to His Younger Self: Focusing on the present moment and the long-term perspective on growth and leadership.
[00:43:27] – Lightning Round: Al reflects on his first job, leadership skills he wishes he learned earlier, leadership myths, and worst professional advice he ever received.
[00:48:21] – Personal Insights: Favorite media outside of work, showing how curiosity and balance in life inform leadership.
[00:50:00] – Closing & Resources: Where to find Al Dea and The Edge of Work Podcast, and connecting with UTA Executive Coaching.

🔗Connect with Guest Al Dea:
👉 LinkedIn: https://www.linkedin.com/in/itsaldea/
👉 Email: al@al-dea.com
👉 website: www.al-dea.com  

🔗Connect with The Edge of Work:
👉 Website: https://theedgeofwork.com/ 
👉 LinkedIn: https://www.linkedin.com/newsletters/the-edge-of-work-7051281049510686720

🔗Connect with Host Keegan Evans:
👉 LinkedIn: https://www.linkedin.com/in/keeganevans/

🔗 More from Euda:
👉 Website: https://www.euda.io/
👉 LinkedIn: https://www.linkedin.com/company/euda-io/

🔗 Follow the Podcast on:
👉 Apple Podcast: https://podcasts.apple.com/us/podcast/bet-on-people/id1882863281
👉 Spotify: https://open.spotify.com/show/5HgXTMbgkDsmuqzUiDGcXc
👉 YouTube: https://www.youtube.com/@Euda-io

Transcript

SPEAKER_02 0:00

You've had a career that has spanned Salesforce consulting. You've launched your own thing with Edge of Work. You spread out and have impact at scale. What's one leadership skill you wish you learned earlier?

SPEAKER_03 0:11

I think it really is in delivering a challenging message. Most of us want to be like it can be so challenging because we're human.

SPEAKER_01 0:19

Today's guest is Al D, keynote speaker, advisor, and founder of The Edge of Work. He is also the host of the Edge of Work podcast, on a mission to help leaders build more human organizations where people and performance grow together.

SPEAKER_02 0:32

Can you tell me about a time that started your foundation of human-centered leadership?

SPEAKER_03 0:38

I assumed that part of leading people also meant, honestly, being liked. What I learned along the way is that being liked and doing the right thing don't have to be mutually exclusive from one another. There is an element of this too of the micro versus the bigger picture, which is in any given moment, you may not necessarily be thrilled with your manager or leader, but in the macro, you can still respect the hell out of them.

SPEAKER_02 1:02

This is such an important piece, and I really like that you just go straight to the language of it's it was about being liked. You're not sugarcoating this around. How have you incorporated that when you're coaching and developing managers externally? Even your clients now.

SPEAKER_03 1:14

Ooh, great question.

SPEAKER_02 1:22

Welcome to Bet on People, a podcast where we explore the decisions behind human-centered leadership and why betting on people isn't just good for people. It's smart business. I'm Keegan Evans, executive coach and founder of UTA. My guest today is Al D, founder of The Edge of Work and host of its NameSake podcast, where he helps organizations develop leaders and navigate the changing world of work. Al is a former Deloitte and Salesforce consultant, whose writing on leadership and talent has appeared in Forbes, Fast Company, and Business Insider. Al, welcome to the show.

SPEAKER_03 1:54

It's great to great to be here, Keegan. Always enjoy chatting with you.

SPEAKER_02 1:57

Likewise. And to kick it off before we dive into the decisions in the format, you and I met almost three years ago at Charter's Workplace Summit with that focus on future work and AI back in 2023. In the intervening three years, what's the biggest change to how you've seen developing leaders and leaders had needing to develop since then?

SPEAKER_03 2:19

Ooh, great question. I think more than anything, it has been a back to the basics kind of thing. It has really solidified that some of the fundamentals of what we know to be a great leader still really matter and are still really important. The ability to set strategy, the ability to drive clarity, the ability to offer guidance and feedback to employees, the ability to enable an employees to navigate through change. Those are all things that mattered before AI really came into the ether of how we think about how many of us knowledge workers do work today. And I think they just have shown that they've become even more valuable and even more important, both in terms of what is needed to lead effectively in this changing world of work, as well as, for that matter, as the workplace does start to, in some cases, shift more towards workflows that are being done by both humans and machines. Some of those same human leadership skills actually still matter in a lot more ways when you're not just working with humans, but also with machines. And so I think we're at the early stages of that, I would, I would say, at least in my own observations. I'm not sure if that's something that is broadly applicable across the enterprise, but I think it just gives even more credence to some of those fundamentals of what we know uh makes an effective and an impactful leader.

SPEAKER_02 3:45

There's uh no argument there uh in terms of of keeping clear to the basics and and and effective team organizations that how team frameworks and how and how they can be applied. Kind of as a as a high-level status check. What when you're talking to leaders at all different levels, how how we do it on maintaining that.

SPEAKER_03 4:04

I spend a lot of time that uh on this word. It it really is around change. Um that's the basis for a lot of the work that I do. And to me at least, I don't necessarily think that change is a new word. I think it's something that to many degrees has always really been there. But at least in my observations and the work that I do and the conversations I have on the Edgework podcast, change certainly has felt different uh over the last, I will just call it 12 to 24 months. And I've been trying to put a pulse on what is it that makes change so different this time around? You know, we've had change before, we've had technology change before. And to me, what I what I've come back to, uh going back to your question about leaders of all levels, is that it really does feel like right now we are collectively in a liminal space. Uh, if you're not familiar with the term, it's this general idea and concept of an in-between or transitory period between two sides. And to me, there's one side, which is the past, which is well documented and well uh trodden and is very, very clear. But most of us don't necessarily want to navigate and make choices by indexing to the past because every day that goes by, the past becomes less relevant. On the same token, there's the future on the other side where we can see some of it. And if we squint a little bit, we can see some through lines, but it's not fully formed. And so we get to the present, which is the liminal space, which is the in-between, where you know you don't want to go to the past, but you're not quite sure about how to go towards the future, or you feel uncertain about it. And so then what happens? You kind of get into this uh challenging moment where it can feel really hard to make a decision, or you kind of get stuck in this uncertainty with all the change that's happening. And I think, to me at least, when I think about the change that is happening and why this feels different, that notion of the liminal space is is what really comes up the most. And, you know, bringing this back to leaders, I think when you're in those moments when you're not quite sure how to make a decision, what happens? You either spin and get stuck in analysis paralysis. Um, you kind of retreat inward in terms of hopes of that this too shall pass. And so once we get to a point where things settle, then you can go and move forward. And I think it can be a really tough place to be, particularly when it feels like everything underneath you, that ground is really shifting.

SPEAKER_02 6:34

I've heard you talk about the liminal space uh concept before and where we are and and the role of leadership. And I'd like to tie it in with falling back to kind of the basics of leadership. And we've had conversations that uh even in people and machine uh combined workforces, the name of the podcast has been on people. So we're you're on here uh with a certain alignment. How did you come to I'd I'd love to go through kind of the path and arc you have gone on to find uh that human-centered principle that it can help guide you through this liminal space? So we always like to start with a decision of where maybe you you didn't quite achieve what you wanted to uh by making a buy-the-book decision. So can you tell me about a time that started your foundation of human-centered leadership with that kind of a decision?

SPEAKER_03 7:25

Sure. So early in my career, I was meeting a team. And as a leader at the time, I would say that I I I understood that I had a responsibility in that role in terms of not just executing the work, which was important, but also in terms of watching over and looking out for my people. So I think conceptually I understood that was part of the job. I think tactically and day by day, I certainly struggled in the execution of that. And, you know, I think for me at least, one of the things that I know now, having delivered at this point, God knows, maybe a hundred workshops on how to give feedback and the ways to give feedback and how to do it in a way that that helps people. I I recognize how important it is as a leader or manager to be able to provide feedback in a way that helps people make better choices and uh about how they go about their day. But back then I I I don't think I fully understood that. And I think at that point in time in particular, I assumed that part of leading people also meant honestly being liked. And so what ended up happening was I had someone on my team who was a high performer, but also just observing them and just their uh the way in which they moved throughout their work and their interactions, I could also tell that they were a little bit more on the sensitive side. When things did not go their way, or when they did get uh feedback that one could consider to be uh constructive or whatnot, they tended to get uh defensive. And again, trying to pair those two things together, I think what that ultimately I uh reflected on upon that was if I ever have to give this individual feedback, I am definitely going to think twice about how to do it, or if I should do it for that matter. And so what ended up happening was there was a project that our team was working on where this person in particular, the way in which they were going about how they worked with other people, was off-putting to a lot of those other stakeholders. And so much so that it got to the point where even though the project got completed, uh, those stakeholders actually pre-out proactively reached out to me to volunteer hey, this is how that process went in terms of working with this individual. Here's why that was hard. And if we're gonna work together in the future, we we hope that there can be a better outcome the next time around. And I think again, there's this this like I was saying before, I think early on in my career as a leader, I think rationally I understood what my job was, but tactically I really sometimes struggled in terms of the execution of it. And in my head, taking that information in and trying to figure out what to do about it, my best course of action at that point in time was not to action on it. And in fact, not to give that person that feedback. The result of that was eventually this getting back to the individual, uh, much later down the road, where they did not end up getting the performance rating that they would have wanted. And part of why they did not get that performance rating that they wanted was because uh the feedback that they got at the time was that there were people who had some feedback about the way in which not just had how they delivered results, but how they worked with others in the process. And so eventually we did have a conversation, and this conversation was a heck of a lot harder in hindsight than it probably would have been had I not been a little bit more proactive about getting ahead of it. But I think at the time, uh, going back to like the spirit of the question, there was a set of calculus I was trying to do in my head around what should I do here? And I think I prioritized, honestly, my own comfort over what arguably might have been better for the individual. And I ended up paying a price. So I'll leave it at that and let you kind of dive in and wherever, wherever it makes sense.

SPEAKER_02 11:41

Sure. Yeah. Was uh was this a um you were a leader of a team and this individual was on the team, or was it a peer-to-peer? Okay, so there was there was the established author a gradient authority. You don't have to talk specific names, but I'd love to get a little bit more kind of picture and clarity. What were you observing? What were you feeling along the way when you were noticing these behaviors? Uh you talked well about the macro decision not to not to kind of give the feedback, but tell me about kind of the day-to-day when you were observing these things and deciding or not to on the I mean, I think for me, the big thing was I was at a point where, again, like I think that part of what I thought being a good leader was was being liked.

SPEAKER_03 12:22

And the barrier of that is if you're going to index on wanting to be liked, there will be times when maybe you make dis other uh uh disadvantage or there are times when if you are indexing on wanting to be liked, that you may decide to make a decision about doing something, or in my case, not doing something uh that might actually be beneficial for the person or the business, but might not be beneficial for you. And in my case, like I think just that fear of well, if I give them this feedback, then that will kind of take away that goal of of being liked. I think that was really ultimately like the crux of it. And you know, I think as I mentioned, I think more than anything at that time, I think I put my own insecurity, uh, my own desire to be liked ahead of what probably was best for the outcome as well as for that individual. And I think the what that looks like in the micro is just the unwillingness to at that point do the hard thing, or you know, more more objectively, to do my job as as what a reader was.

SPEAKER_02 13:39

Sure. Thank you. That that's and I push down into that kind of individual day-to-day thing because it is a continuous series of choices um when we're going through it uh for that for that part. This is such an important piece, and I really like that you just go straight to the language of it's it was about being liked. You're not sugarcoating this around, trying to professionalize, formalize that that that you had that you had this experience of I thought being a good leader included getting like being liked. How have you incorporated that in when you're coaching and developing managers uh externally, even your clients now?

SPEAKER_03 14:12

Look, I mean, I think most of us want want to be liked, right? Um I think it's a it's human human nature, right? And I think that's I think that's okay. And I think that's I think that's human. So I'll I'll say that. Yeah. But I mean, upon reflection, and you know, certainly after that point, having had other chances to be in those situations and have made a different choice and having seen the impact of that, I think what I learned along the way is that first off, being liked and doing the right thing don't have to be mutually exclusive from one another. I think in some ways at that time I I tended to look at that as a false binary, but uh I've come to believe that that's not necessarily true. Yeah. Uh I think the second thing is that there is an element of this too, of the the micro versus the bigger picture, which is in any given moment, you you may not necessarily be thrilled with your manager or leader, but in the macro, you can still respect the hell out of them, right? And so I think there's an element of this of being in that moment of being a little bit short-sighted. But I also think the third part, which I didn't give enough credit, which is something I do help a lot of people think about now, is I thought at that point in time that delivering the feedback was a one-way conversation and a one-way door. When in reality, it could be that, but it doesn't have to be. Those moments of feedback where you are being objective, where you're trying to paint a picture of a behavior that someone did or didn't do, and in some cases trying to encourage or offer up perhaps more constructive ways of doing that thing, those don't have to be just you pontificating or sharing. Those can be invitations for a bigger conversation that could be helpful to you and it could be helpful to them. And what I didn't know then, what which is what I know now and what I encourage now, is that you can actually learn a heck of a lot if you are a leader, if you are giving feedback and treating it as a two-way conversation. Because there are gonna be times when maybe you are wrong in what you said, and you're gonna get some more insight that's gonna inform what you do. There are gonna be times when maybe you are right, but you're gonna get better insights by just actually having them play back to you uh what they saw or what their perspective was. And I think what it ultimately taught me is that those are moments when you actually can learn a lot by just having the conversation versus feeling like you have to be the definitive sole arbiter of what is said in that conversation. And of course, there will always be conversations where they tend to be a little bit more one-sided versus not, but not all of them have to be that way. And so I would say that is one perspective shift that I try to help managers and leaders see, which is that particularly when it tends to be feedback that can be really challenging to take, that it isn't necessarily meant to be a one-way door, that it can be like a two-way door. And so I think that's one thing that that I've I've come to learn and I've tried to really incorporate in terms of how I try to help other people shift their thinking on it. Because the reality of it is that feedback can be really hard to both give and to receive. And so I think sometimes it's just helping people see a whole uh uh a different side of it and a and a and a fuller side of it.

SPEAKER_02 17:40

Yeah. Approaching a crucial element in that two-way conversation or two-way version of feedback is curiosity, and especially from a leader towards the employee or towards the the other other participant. And I I know that uh you not only teach that as a conceptual thing, but in the second example you gave us, uh, it sounds like you leveraged that kind of curiosity to recognize that there was a high performer, wasn't getting opportunities, maybe wasn't in the right fit, and learned uh and and figuring out how to what is the best thing for that person and the team at large for a better fit. Can you tell us a little bit more about uh about that example?

SPEAKER_03 18:18

Yeah, I mean, I think the reality of that example is learning from, in that case, really uh some of the mistakes I made it the first time around, which is number one, certainly it is oftentimes, more often than not, better to have the hard conversation than to not have it at all. And then number two, not necessarily having to feel like you have to have all the answers to have the hard conversation, but that you're willing to come to the table and at least have it and offer suggestions and ideas. And in this case, I I did have someone on my team who they were very, very capable. And there was just a lot of change that was going on inside of our organization at the time. And we had been through at that point probably three re-orgs within a year, and there were gonna be more that were coming. And they were just not in a role where we were actualizing off of their full capabilities, and I could see it, and we had conversations about it. You know, this was we had a pretty collaborative relationship, and I could tell they were frustrated, but they were also uh just in terms of their voice and their tone, but also we we had open conversations about it, so this was not necessarily a surprise. But after the last set of uh reorgs that had happened, it was very clear to me that things were not gonna get better anytime soon. And so, you know, in that moment, I mean, I would have loved to have had her stay on because I could have definitely used the support going through the next couple of months, but I also knew what she was capable of and what she could do if she were on a different team, or quite frankly, were just in a role that just had a little bit more stability and was actually actualizing on some of her talents and strengths, and so it turned out uh there was another team that was hiring for a role, and I knew the hiring manager, and so I had just reached out to this person on my team, and we had that hard conversation of like, hey, look, I know things that are not great right now, and if I'm being honest, I am not sure that they're going to get significantly better. I would love to have you on for the ride, and I know what we've talked about, and I also know what you're capable of. But if you are open to it, there's this other role is this something you'd be interested in? Because if it is, I would be happy to do what I can to try to help you land over there. I can't make promises, but it's something I'm committed to because I would rather see you be successful than to have you continue to do some of the work that you're being asked to do now. And sure enough, they were open to it. And I was fortunate enough to have had a good relationship with the hiring manager that so much so they were actually in the midst of like actually about you know getting pretty close to to to to doing final round interviews for the role, but uh they were willing to make an exception, and the person who reported into me, um, she crushed it in the interview so much so that eventually they they gave her they gave her the offer and she was able to move teams and she's still at the company this day and is still killing it. But you know, it it was those one of those things where honestly in hindsight, I don't want to make it out to be that it was easy, but to me, the writing was just so clear on the wall that this person was just so incredibly capable, but it was also just so incredibly clear-eyed to me that if they stayed on our team, they were just gonna get caught in the shuffle. And I think I just I I wanted to I wanted to know that they could have they could get a fair shot at fully using everything they had to be able to to contribute because I really, really believed in them and still very. Much believe in them, and yeah, I was fortunate enough to play a small role in making that happen.

SPEAKER_02 22:04

Yeah, that's great. What were some of the strengths that uh she had that that were the signal to you that and and maybe the painful things to lose on the team?

SPEAKER_03 22:13

First off, they were pretty junior and they had a much clearer understanding of the nature of our business than many people who were at my level or above. So that was the first thing. I think the second thing was that they were constantly coming up with ideas about things that would potentially help the business that were just never seeing the light of day, even you know, with the right coaching, even with raising it through the right levels, even through all of the things. And so it just was very, very clear that they had both like the potential as well as the acumen to do more than what we were giving them. And for that matter, they also just were very willing to always roll up their sleeves to do whatever was being asked, and that was both good and bad in so many ways. Good in the sense we were grateful for it, but bad in the sense it was just so clear how much more capable they were than what we were asking them to do. And every time we gave them something like that, it just was very clear that Delta just grew farther and farther away of like what the potential was to what we were asking them to do, just because we were going through a period of change and we just kind of needed all hands on deck, and you know, there was no I had no problem giving her that work in the sense of it needed to get done, but it always grated me a little bit because I just knew what they were actually really, really capable of, and think that over time it just kind of got to a point where I was like, if there is a way to shift some of this, it would be great. It would be great to to try to do that because I also selfishly I sort of knew what it felt like because I was there at one point too, and just kind of reflecting back on my own experience and and what leaders had done for me, I kind of went back to that bag of trips to be like, okay, well, there's there's there are some things that are at my disposal that I might be able to do to help in the situation. Let's see, let's see what we can do.

SPEAKER_02 24:17

You mentioned even with the right kind of coaching, the the great ideas weren't getting elevated. Uh, it sounds like there's a lot of structural and systemic challenges to this person finding the right groove or the or the right uh the maximum potential growth pattern, which you were trying to get them on. In addition to that, though, were there uh opportunities for them that you were trying to provide feedback that just wasn't taking because in the team or that they needed someplace else to to grow?

SPEAKER_03 24:44

I mean, I think you're probably right in it being systemic and structural in terms of the challenges that were going on. I mean, certainly there probably was an element of it of the hierarchy that was in place in terms of what her level was versus relative to what some of the other people in the rooms that she was in were at. And and some of that, regardless of where you are in the org, doesn't go away. That said, there were a lot of structural things where quite frankly, like we just the the orb we were in just was going through a lot of change. And there was just a lot of things going on that just in those those moments, it uh um it just wasn't really conducive for some of those things to really marinate to the top or really be acted upon. And I just not that you can ever really get a quote unquote normal um uh uh opportunity, but in the back of my head, I was just thinking to myself, like, man, like if we could just get her over into a role or a team or an environment that is quote unquote normal, I think she could really do a lot. And and it and again, like this had less to do with her and more just to do with some of the systemic stuff that was going on at that point in time.

SPEAKER_02 25:56

Yeah. What I really like about this is the is the by the book business wisdom is you've got this really high performer, you've got this team that's going through a lot of change and therefore probably needs some shoring up with high performers. The by the book is keep them on the team. They're they're comfortable and say junior enough to do a lot of the scut work uh and and what comes to them. But you saw the potential, you saw you knew that the team could handle like with all the change, whatever was going on, and this person longer term had a lot more potential for the organization at large and and and themselves. Is that is that a fair read?

SPEAKER_03 26:31

I think it's fair. It's it's we probably said it better than I could have I've thought about it. I mean, yeah, like I I do think that the I think the reality of it was is that there really was that part of me that understood and could empathize a little bit of the situation that they were in. And thinking selfishly to myself, you know, what would I have wanted someone to do? But I also I also think part of it really was my own belief in their potential of what they were capable of, and just wanting to to see if I if there was anything I could do to facilitate them getting a shot to do that, that they they would. And sure enough, you know, within uh probably about uh a year, they ended up getting promoted after being in the role and the team that they were on. And so uh, and let me be clear, that was everything that they did. Uh, I had very little to do with it, but in many respects, I felt vindicated knowing of like, okay, like I I I I uh I knew that this person had a lot more than what they were able to show because of where they were and what we were doing. And clearly they were able to show that in this other role because they wouldn't have got promoted it that quickly if they weren't. You could take the victory lap on the vindication on that one.

SPEAKER_02 27:47

So we've got two examples of feedback and insight and spotting out spotting potential decisions that have been formative for you. And I know for your for your third favorite story, we're going all the way back to the beginning and probably cannibalizing my uh my lightning round questions. Um, but tell us about this this favorite experience, this formative experience as a manager for you.

SPEAKER_03 28:07

Sure. So the the first time I became a manager actually was in the first job that I ever had, which was working at a golf course growing up in uh in my hometown. And I started working there because I played golf at the time. And part of the deal was most of the time, if you worked at a golf club and you worked a couple times a week, you would get to play for free at least once or twice a week. And so part of my motivation, I think, at the time to even get a job was so that I could go play for free because uh I was 13 or 14 years old, and you know, that was the way you made money uh uh and whatnot. So I ended up joining as a caddy. If you're not familiar with a game of golf, caddies are the individuals who often carry the golf clubs and the golf bag around for the player who's playing and they help them navigate around the course and and all that kind of jazz. And so I loved it, and it was a lot of fun. Uh, who wouldn't want to be outside a couple hours a day around a sport that they enjoyed? And more than that, though, it definitely also allowed me to be in an environment where you're around a diverse group of people. Most of the people at the country club I uh uh worked at, you know, were fairly well-to-do, you know, middle class, upper middle class, and the like. And so at a very young age, I was exposed to a lot of professions, a lot of business owners, doctors, lawyers, uh, all the like. And in many ways, it was a really eye-opening professional development experience and exposed me to a lot of things at a young age that I think would prove very valuable down the road. More specifically, after about a year or two of being a caddy, uh the gentleman who ran the caddy program came to me and said, Hey, what do you think about basically ticking over and being the manager of the day-to-day manager of the caddy program, where you'd be responsible for all for all of the day-to-day uh management um opportunities uh uh of running the caddy program and the 60 or so independent contractors who were caddies. So I said, sure. Um, and you know it's funny. And how old were you again? I was fifty, I was 14 or 15 at the time. Okay. Um so even back then, uh this whole idea of being very good at your job and then getting asked to be a manager existed in you know the early 2000s as it very much still does today. But that job taught me so much. And I certainly think it in with the benefit of hindsight, certainly helped pave the way for some of the work that I do today. But at a very young age, I really had to learn the art uh and science of managing and managing people. And it was challenging, it was rewarding, it was fun. Having to manage uh at the time as a 14 or 15 year old, people who were your age or older was a really big challenge. I mean, if you think managing adults is hard, try managing a bunch of teenagers who I won't don't. Yeah, exactly. But also so rewarding in so many ways. But there's a particular story in there that I I'd be happy to talk about because I think it sets the stage for uh I think a lot of how I see the world and how I try to operate today. So one of the nuances of being a caddy at this club was that everyone was an independent contractor, which more or less meant you could choose when you wanted to work, right? And our busiest day times of the week were Saturdays and Sundays, naturally speaking, because that's when a lot of people want to play golf. So there was a period in the summer where we were just getting slammed. Like it was just was so busy, the weather was great, everyone wanted to take a caddy, like that's all a good thing. But in particular, there was a period where just it was really hard to keep up with the demand of just not having enough supply. And so we needed more and more caddies to come, and they just were not coming, and I was getting a lot of pressure on the other side of it because I was like the manager. So had a situation where one day, after a pretty busy morning where we didn't have enough supply and way more demand, there were a bunch of caddies who ended up showing up in the afternoon. And one of them kind of came over and was just started talking about, hey, yeah, sorry, I I was late. Uh, and before they could really launch into what they were explaining to me, I think I just hit a you know, a frustration point and I just started lashing out. Not so much at them, but still yelling out loud, just you know, hey, this is like not helpful, like we really could have used you. Um, you know, you know, uh why are you coming now? All these types of things of not really being angry at them, but they just happened to be the person that was in the way of what I was frustrated at the moment. So naturally I was taking it out on them. And after I finished pontificating on whatever I was saying, they began to talk and they were talking about and they were trying to apologize for the fact that they weren't there and why they had been missing these past couple weeks. And part of why they had been missing is because someone in their family had gotten shot and had been in the hospital, and that person was the person who was responsible for driving them around. And they had not been able to come to the club because they couldn't get a ride, and finally this person had gotten out of the hospital and they were doing much better, and so they were back to being able to take them. And immediately, because I was a 15-year-old and a decently smart enough one, I immediately felt awful and I immediately knew that I was not acting in a way that was uh effective or for that matter, just very caring at all. But uh, you know, and so I apologized and fumbled through some stuff and and and said what I thought I needed to say in the moment, but that moment really stuck with me in my life as a human being, but as well as as as a manager or leader, which is you you can only see from your seat. Um you you you can't really know what's going on in someone else's world unless you you you actually go and like find out, right? And I think it was um it taught me a lot about empathy and and not just empathy, but also in taking the time to understand where people are and where they're coming from before making any assumptions about how they might be communicating, how they might be behaving or anything like that. And so that's just something that I've tried to take with me in the interactions I have uh on a day-to-day basis, as well as for that matter, in terms of how I think about things like leadership or anything else, which is that the unless you actually take the time to see from someone else's seat, unless you take the time to really understand someone's context, it's really hard to know precisely where they're at. And until you actually go and do that work, it can be really difficult to get a message to land or to really uh work with them in a way that gets them from where they are to where you want to go. And it really is something that I take into account whenever I'm trying to work with anyone.

SPEAKER_02 35:05

That's powerful. Uh, and over a series of conversations, you I I've always felt pretty valuable aligned with you. Our our first leadership principle at UDA is treat everyone as if uh they're trying to do the right thing. And that is opening up the curiosity that it's kind of a through line of our conversation here so far of where are they coming from, what's going on. The leader's responsibility is to find the bridge and support and get more out of the collective group and the sum of the parts. And you can only do that through knowing the people uh underneath. So that's uh that's a powerful lesson to learn at 15.

SPEAKER_03 35:38

It was a lot. I mean, it's and it was to the point where you know, over 20 years later, I'm I still remember it as vividly as when it happened. But yeah, I'm in many ways, I'm I'm grateful for it. I'm grateful for that for that it happened, but in the sense of what it taught me, but also for that matter, while I wasn't perfect in that moment, sure. I'm grateful that I at least at that age I was young enough. Uh even though I was young, I was mature enough to know that there was something in there that I needed to sit with and understand and to to be able to to wrestle with so that I could be a uh effective leader and also in my view, uh just a a good a good person that I would that I would want to hold myself to a standard of of being in an interaction.

SPEAKER_02 36:25

So not for nothing. I tend to find the best leaders are also those who want to be good people. Yeah, yeah, yeah, yeah, yeah. It's been 20 years-ish. Uh, we'll say I won't I won't pin you down on that on on the air.

SPEAKER_03 36:39

23 if we're being in if we're being precise, but who's counting?

SPEAKER_02 36:43

You've got you've had a career that is spanned. Uh, we talked about on the intro. Salesforce consulting. You've launched your own thing with edge of work, you spread out and and it have impact at scale. Uh you talk about this all the time. What is something that that 14-year-old uh when when the the boss of the uh the country club first threw it out there? What is something that that 14-year-old uh needs to hear from you uh from her right now, Al?

SPEAKER_03 37:12

I'm trying to think of something that's not so cliche. I think what what I would I would want them to hear is that at that point in time, and I'll be honest, I don't spend a lot of time around 14-year-olds as much anymore. Um but at that point in time there was a lot of focus on where are you going next. And I would encourage them, that 14-year-old, to try as much as you could to just think about what is happening right now. And I would say I'm still not great at this, although I just have the benefit of understanding it rationally at my age now versus understanding it rationally at 14 or 15. But there will always be a next thing. And instead of worrying about what that is, so much of what that is, if you could worry about what's right in front of you, there will be a time to worry about that next thing when it comes. And and again, I I can't say I'm perfect about this right now, but I rationally understand it a lot better, and unless I think I'm able to modulate a little bit better. Yeah. But I think if I had known that at 14, I think I think that could have that, I think that would have been a worthwhile thing to to intuit and to to understand.

SPEAKER_02 38:30

Yeah. And it's not a binary of uh going back and forth. We we sure like you said it, you said yourself, that you there's time to think about what that next thing is. But if it's always just about the next thing, uh and especially as a leader, uh there has to be defining reality uh and and the vision, but yeah, creating a time for people around you. We didn't use this word in in the in the different conversations, but but the the concept of like a through line of trust comes up for me, uh and a leader's responsibility to trust. And before we move on to the lightning round question, I'd love to hear how that plays into the work you do now and and um how you think about leadership and and around building trust.

SPEAKER_03 39:13

Yeah, I mean, without being tried, I think it is one of those foundational currencies. And uh so I'd say a couple of things about trust, because I I love love talking about this. So the first thing is that I think it's one of those things where if you're thinking about building it, then you lost the plot. It's something that you naturally do each and every day. Sure. Right. And uh that's not to say you shouldn't think about building it, but but it's more of just the the the thinking and the and the mindset behind it.

SPEAKER_02 39:40

I'll take you we'll we'll have you back and we'll talk about metacognition and all that fun stuff. But sure. Yeah, but I but I under I I like the I like the point that it needs to not be the only thing you're architecting.

SPEAKER_03 39:52

Sure. Well, and it's more along the lines of I I think the where I was going, what I was trying to articulate was if you're at a point where you're thinking about it like that, it's usually because in that moment you need it. And if that's when you're thinking about it, that's a really tough thing to generate quickly, just because it isn't something that you can just naturally generate quickly, right? Uh it's a lot of time to be you know, because you need the buy-in and support, because you need those resources, because you need that opportunity, um, be because you need the side-off, because uh and so forth and so forth, right? And so uh the build it before you need it, I think is is the the message that I'm trying to communicate. Um, there's a bunch of different models to think about this, but ultimately the one I always go back to is that the there's two kinds of trust, cognitive trust and affective trust, right? And so the cognitive trust is more along the lines of do I believe, Keegan, that you are capable of doing and will do the thing that you said you will do. And then the affective trust piece of it is the idea that Keegan, do I believe that you have my best interest in mind, right? And and so said it another way, it is competence and warmth. And so the more you can think about both those and and how you demonstrate those, I think both matter, right? Um, if you imagine, you know, a two by two, sorry, consult old old habits die hard as a consultant, but if you imagine a two by two, trying to be to project both competence and warmth is in that that top right hand corner of what you want to do. And then the last piece of this is what I've said before, which is if you're thinking about it in the moment, it's probably too late. It's really thinking about what am I doing each and every day in my interactions and my communications, in the way in which I show up for people, in the way in which I relate to people, in the way in which I engage with people, where I'm demonstrating those small interactions of cognitive trust and affective trust, right? And so the and that is also why I think if you are someone who is wanting to be seen as as trust, someone to be worth that is worth being trusted, that it really is about how do you take what you're already doing and just being more intentional around it. And and maybe supplanting a few things on top of it, but uh it isn't as much about you know doing a massive big thing or a group thing of grand scale. I think it is more about how do I take some of those everyday moments and interactions and sprinkle them a little with a little bit of ways in which I can be seen as trusted.

SPEAKER_02 42:14

Yeah. Thank you. Uh and I really appreciate the breakdown and of the passion clearly around around trust and the uh and the thinking about it. It's also very clear to me how you learned that lesson across the three stories, uh, putting them in chronological order. You learned the lesson in the uh in the in the caddyshack. Uh I was going to get that out once it with that kind of immediate reaction, reactive moment, and then and then figuring that out. And then thinking about, is it better to be liked or give this feedback? Uh and then the story about finding the right place for that high performer, that was a story of ongoing long-term trust that you had to have have continued to have these trusting um and trust-building interactions to understand and to know where they uh where they were going to shine, where they weren't, and for them to trust you to move on. Uh and the last thing I'll say about this is I appreciate you indulging in it uh and coming back with cognitive trust because I know the last time we recorded a podcast, it never went to air. Uh, and this time we are getting it out on the air. So with that, uh, I'd love to transition over to the the lightning, uh, the lightning-ish round. Al, if it wasn't the uh the caddy job, what was your first job? And it's fine if that was the caddy, if it was the first job.

SPEAKER_03 43:27

That was in fact my first job, but I think if I reflect on this a little bit more, uh one of the other jobs that or one of the other jobs that actually came out of the caddy job was um there was someone in there was a specific member at the club in particular who I used to caddy for all the time. And one of the things that uh he offered me, particularly because I was in upstate New York when uh you can only play golf about six or seven months a year, was actually a chance to basically work at his construction company. And I wasn't working on the job site, but I was working. in the office and just doing a lot of office and clerical work. And so uh but the I guess the lesson you know in there in that is that um you know sometimes when you do good work for people other opportunities you know really come your way and it was through that that really honestly showed me the power of one of the ways in which I've witnessed the power of just having trusting relationships you know because if a guy can trust me to carry his golf clubs around and uh pick the right clubs for him and to hit uh he can also help you know trust me enough to uh answer the phones in uh in in his construction company.

SPEAKER_02 44:36

So all right what's one leadership skill you wish you learned earlier?

SPEAKER_03 44:39

I think it really is in delivering uh delivering a challenging message. And I would also say at least in my line of work that is like one of the most requested topics that people really stress still struggle with right um because it is it can be so so challenging because we're human right and so I think and I'm still honestly I'm still learning it so yeah I would say that one. The good news for folks like us is it's easier to help other people uh deliver that yes uh while we're still on our growth yeah of course exactly uh what is the biggest myth about leadership that you've come across in your in your travels so I'm gonna cheat on this a little bit I wouldn't call it a myth but I do think it is worth worth mentioning I think a lot of times it tends to focus so much on the individual leader itself and that absolutely matters but the whole point if you look at the definition of leadership in any textbook any textbook it's about being able to drive results of a group of people and while an individual plays a role in that it's ultimately not about you. And so I think that the shift that we miss sometimes is that it is more about the collective versus the actual individual itself. The worst professional advice I've ever received so this is uh it's less of a trite thing and more specific I remember when I was working on one of my first consulting projects uh at Deloitte I I was on a specific work stream and there were some a couple other work streams that were doing both work that was impacting mine but also work that I was genuinely curious about. And so one of those people I reached out to them and I set up time to go and meet with them just to better understand what it was they were doing because it it just sounded really interesting. And I think she must have mentioned it in passing just not without anything thinking of it to another leader on my team at the time. And so eventually it got I was talking with this leader and he you know had said something to me to the effect of like oh I heard you were talking to this other team about their what they were doing and that you showed some interest in it. And I was like yeah and he and they were like I would be careful about that if I were you I would really just focus on like what it is that you're doing. I will very much tell you that pretty much I have had success in my career by doing the exact opposite of that. And I have every belief that that leader was trying to look out for me and like I don't think he meant anything ill will by it. But if I look at the biggest successes in my career and I look at that advice everything that enabled me success was going against that. And so I think what the the the anti-pattern to that would be like yes like do your job and if you've got an interest or curiosity run with it particularly if you've got intrinsic motivation behind it. Because what I didn't say those two other work streams that I was trying to investigate they were all about change management and org design which is part of what I do today. So yeah like I I I think in that case like that was really really tough advice to get but I'm glad that I didn't listen.

SPEAKER_02 48:02

Yeah I promised our producers that I'm gonna make a lightning ish all the guests so I'm not gonna go on my thing. But strong tie relationships versus weak tie relationships and weak ties is where the career growth and context building actual success for for the company comes from is you made the right choice is what I'm trying to say. Thank you.

SPEAKER_03 48:18

All right last lightning round question not a leadership or business related uh media recommendation book a show podcast video game anything that you're that what makes Al Al outside of uh edge of work this is actually probably the hardest question to answer and because uh Van like I that this is a separate conversation but my wife is enthralled that sometimes on our big screen TV we watch YouTube videos of how people are building projects in quad code but um uh I have always loved just really basic feel good comedies like for TV shows and things like that uh or and my wife um she likes procedurals but we just finished watching uh RJ Decker which is more or less like a very comedic like barely scratching the surface of murder mystery I mean it's basically like Miami Vice just a a knockoff and it combined like slapstick humor with the murder mystery that my wife likes and so it ended up working out uh for the both of us I don't think it's winning any Emmys or anything anytime soon but it certainly in my wife's mind was much much better than watching someone figure out how to claude code uh and a whole bunch of new workflows and so that was a win for for both of us as a uh as as a fellow entrepreneur and knowing how all consuming it can be I'm I'm very proud of you for finding that win-win with your wife thank you all right Al D is a speaker advisor and founder of the Edge of Work uh Al, thank you so much for joining us and we'll have all this linked of course in the show notes uh but where can people find you?

SPEAKER_02 49:58

What else do you want uh our listeners to check out?

SPEAKER_03 50:00

Thank you, Keegan it's a pleasure to speak with you uh they can uh they can come listen to the Edge of Work podcast wherever you get your podcast or you could find me or connect with me on LinkedIn. Just mention that you know uh Keegan and uh be happy to connect with you.

SPEAKER_02 50:16

Always a pleasure and thank you for coming on and uh I always love running into you at the when when our event schedules uh overlap and I look forward to the next time uh that uh that that happens. Likewise uh as always follow like and subscribe to Bet on People on Apple Podcasts, Spotify and YouTube. Uh and if you want to learn more about how we think about leadership at Uda, visit Uda.io slash executive coaching. I'm Keegan Evans and this is Bet on People