Ep 30 - AI, Leadership, and the Future of Team Management

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Ep 30 - AI, Leadership, and the Future of Team Management Podcast and Video Transcript

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Dave Dougherty: All right. And welcome to the latest episode of Enterprising Minds. We're going to do a quick deep dive on a particular topic today. Just to see what we come up with on one particular thing and it should be fun. So if I'm talking a little weird, it's cause I just got done hanging out with family in New Jersey for a week.

So sorry, I gotta get back to my normal voice. And anyway, we were talking.

Exploring AI's Impact on Leadership and Team Management

Dave Dougherty: About AI and leadership and all these things. And my question to you guys is when we look at managing teams, being a leader, effective leaders what do we lean into now that AI is around your teams using AI and AI will inform how people are acting and reacting?

You know, the idea for this question for you guys came from sitting in the airport reading through my Harvard business review. That's been sitting on the counter for three months before I finally read it. And in there was an article, it was called Leading in the Flow from the January, February 2024 edition.

If you guys want to check that out but the author.

The Five Core Energies of Effective Leadership

Dave Dougherty: Has this idea that there are sort of five core energies that you can tap into, right? So it's purpose, i. e. you're committed to some sort of noble cause, something, you know, bigger wisdom and it's calm and receptive to the truth, like what's actually going on around you.

Growth is the third one. So, you know, you're curious and you're open to new things. Love, Her words, not mine, connected to those you work with and serve and then self-realization, you know, which means you're more centered and joyful in your spirit. And then in the article, the author goes through with, you know, these 25 other things like most business articles, you know, there's the main idea and then all of these sub things that are over-prescriptive, but You know, thinking of our conversation and then in reading in this article, I was thinking, man, you know, it, it does seem to me that this sort of like whole person, holistic, some would say woo woo kind of, you know soft skill kind of thing really might be the, the things to lean into now, because Yeah.

You know, so much of the reliance will be on AI and whatever else. So anyway, that's the setup. I would like to know your thoughts. Who wants to go first?

Alex Pokorny: I can go this is a really good idea. This was a really fascinating idea because three of us, we've been throwing around the idea of two of like post AI.

What does that look like? Are jobs secure? How are things going to change? How are teams going to change, you know, our structures or companies going to restructure themselves if they have the ability to offload a lot of work, you know, how does that change things? This is a really good point.

The Shift from Technical Skills to Soft Skills in Management

Alex Pokorny: I think I brought up before the idea of like a pendulum manager and that's the entry-level manager.

It's a, It's a phrase that I've totally stolen from a conference that I was at, and I just love the imagery of it because an entry-level manager, first-time manager, or if you're managing up, you have this same kind of dichotomy that's always pulling at you. On one side, you are the most experienced, best hard skills, technical skills person, which is how you're kind of rose up in the company in the first place.

And then the absolute opposite side is all these soft skills. And. That's actually how you're going to continue your career trajectory. So you shoot up on one ladder and then you have to basically slide on over and then start somehow being an expert at that, you know, more senior level. So the expectations are pretty high of having somehow gained those skills already.

And then that's what actually will keep you succeeding as you go forward in your career and keep moving up. And that's, that's that struggle point of right when you're at that crux of Technical and you kind of reach the top of the technical side and management on the other side, you're kind of getting pulled in between the two.

It's tough as an entry-level manager because you are the most technically capable person for any project. However, you need to lay off and just go do something else or else you'll end up being a micromanager. And we see a lot of micromanagers, especially at that entry-level, because they can't let go of the fact that they know a lot and they do.

But as especially over time, their knowledge starts to kind of degrade and not become so applicable anymore, but they kind of lose their confidence. So they kind of struggle back to that and try to grab onto it and saying, I still know what I'm doing. And it's like, no, you, you did five years ago, 10 years ago, but things have changed, you know, context has changed technical stuff, especially in the world of search.

Changes super fast. Quick story on that. I had a manager once that it was in front of some executives from a very, very large multinational corporation, which is one of the rare times this small agency ever got an audience like this. And my manager, who used to do SEO from years ago, stated something that was about canonical takes that was completely wrong.

Like absolutely, absolutely positively wrong. And I had to correct him in front of that, like group, because we were going to like launch onto how are we now going to execute on the thing? And I was like, God, like, and that's the, I think I try to keep that memory in mind because that's a problem as we kind of move forward in our careers, just always the further you get away from that technical experience that really hands-on experience, you need to understand your knowledge is degrading, even though It felt fresh and it feels fresh.

We got to kind of pull away from that, too. And I think with the reliance on A. I., it almost becomes even faster with that, where those skills are going to degrade, but we're going to try to, like, grasp onto A.I. to bolster our skills and to check ourselves and try to, like, still hold on to those things. But really, you have to move away and further, further away.

So this is a great article to bring up. The idea of getting into those soft skills. And understanding like that's, that's a very different way of working, but it also is a way of working that makes sense when the technical is, you know, being handled elsewhere, either by your team who should be handling it or by software who can handle it at efficiency too.

Authority vs. Leadership in the AI Era

Ruthi Corcoran: I really, I like that take a lot, Alex, and it's quite distinct from my initial reaction which was more along the lines of, hey, there's this concept of authority versus leadership that we've heard about writers and speakers like Simon Sinek has talked a lot about this sort of distinction.

And when you talk about those soft skills, I think those sort of fit nicely into this leadership idea. And then you toss on this layer of A. I. I fully agree with Alex. That's a cool lens in which to think about these different soft skills and how we might adapt them as we move into this new world of technical change that's coming with A.

I. And what occurs to me is that authority is a very valuable way of driving results when the process is known and when you're sort of in the process of optimizing what already exists. Leadership is much more effective in cases where there's a lot of uncertainty. And you have to lean into those soft skills a lot more because there's not a known process There's not a right way of doing things and therefore that sort of Authority focus on here's how you've got to do it and you've got to drive it in this particular way Is not going to be so effective instead.

We need to focus more on that. How are we growing? How what's our purpose? What are we driving for so that we can continuously adapt to the new world?

Alex Pokorny: quick little side question for you Just thinking about authority and leadership and that topic Dave, we'll get back to the first point. But I'm just curious about this because I had a very distinct kind of memory in my mind of being at a large company and the VP, I swear, changed roles every three months.

Yet another one, the latest reorg, right? So, He has a massive audience and I don't know, 200 people maybe in this giant room, and 10 minutes passed by, 15 minutes passed by. He's in the front of the room talking to various people and we're all just sitting there waiting. And then eventually he gets up to speak.

And at that point, people are just annoyed, like the feeling of the room. Was palpable, like, you know that this was not going well. And I thought about this just at the very beginning because authority, he had authority, but he did not show the leadership skill side of it, right? So he was in charge of giving the responsibility of this entire organization and he has these people just sitting there waiting for his desire of his, his whim, right?

So it was really kind of showing off that authority side of things. Is he a leader by doing that? Absolutely not. Do you, however, go through the same kind of feeling of distrust when there's a brand-new leader? Where you're not sure about them yet, like who is this new person sort of thing? And then as they stay in their role for a period of time, do they somehow gain authority and leadership by literally just being, Oh, that's the VP.

He wants this. And we just do it instead of being, here's a brand new guy. He wants something being like, wow, let's see what he actually wants. Do you ever feel that feeling of, and does that change with time? Is that literally an aspect of time or is that an aspect actually of leadership qualities being shown over time?

Dave Dougherty: I think you said it with trust. Right. You know I immediately, you're always reading all the, the, you know, seal team six, you know, General MacArthur's daily advice kind of books, you know, like, so I'm surprised you didn't make the military connection where like, and, you know, like World War Two, right, you would have the lieutenants that would come in out of West Point.

And for these people who've been in the trenches, like completely disrespect them because you know, they haven't actually seen actual combat. They only know the theory, right. And they would be switched out really quickly. So yeah, you have to earn the trust of the people around you to know that you're going to be acting in, in their best interests.

And that, that develops over time, but there's, you know, some important markers you can do. With how you conduct yourself and how you speak like for me, I would be pissed about that because, you know, you're wasting my time. That's disrespectful. My brain when Ruthi was talking. Especially with this distinction between authority versus leadership.

I was like, well, then, you know, that whole category of thought leadership content is mischaracterized. It's not actually leadership. It's everybody's peacocking for authoritativeness. I am an authority of this thing. You know, hear me roar.  

Yeah, because on the one hand, it's like the reason those books by Malcolm Gladwell or Daniel Pink or Simon Sinek are interesting is because they've done a bunch of research. They're an authority on a very niche topic that they've put the book together on, but then there's that so what, which is to me is that leadership piece, right?

Like there's you know. If you go on some like old school leadership idea, ideology, right? The theory behind the leadership, you, there's really like three jobs for a leader it's to, you know, come up with a vision, galvanize trust around the vision, and then make sure it gets executed against, right.

And I'm talking broad brushes, you know, and. I think we've, we've jumped around on that, you know, galvanizing the troops mostly because we are in that midsection with our careers right now. You know, we're getting it from both ends and you have to translate both things. So yeah. Do you think with the changing landscape that we have right now, like with the tools and whatever else, like, have you changed the way that you're managing your teams in terms of like, I know?

They're going to be bringing, you know, AI-influenced or you know, AI materials as their work deliverables, even if they won't necessarily cite it. Cause you're seeing articles, a bunch of, you know, 80 percent of people are, you know, using AI and blah, blah, blah, blah, blah. It's like, okay, fine, fine. I expect everybody to at least be trying it, you know, whether or not you're using it, you know, in your day-to-day is a different thing.

Ruthi Corcoran: I know, I think it's the short answer. When I, when I think about Shifting the way that I might interact with colleagues or team members from direct reports or even management. And it's there. It's a shift in the different tools that we have to use and available. But that's kind of like, that's like checking how somebody did their busy work.

You know, it's just, it's, it's not very interesting. I think what's much more interesting is. Are we able to encourage our colleagues and our team members to be as effective as they possibly can be? And so I have a tendency, I think, even before you laid out this framework, which is very helpful to even think more deeply about it.

I have a tendency to lean into those more with the folks around me. Because I think that that's going to be much more impactful. I'm much more interested in leading into what are, what are the things, the natural talents, the skill sets that people already have, and how can we amplify those to help that person or that team be much more effective than they otherwise could be.

One of the things that the questions that I asked both my team and myself is what is your production function which is I've taken, this is a variation from something I've gotten from the economist, Tyler Cowen, who asked on his podcast, or at least used to a number of guests, what, what their production function is.

And the way I think about that question is. What are the things that allow you to be most effective at what you're best at? So as an example, one of the things that is a huge core part of my ability to be successful and effective in my day-to-day life is reading or listening widely and taking walks to be able to think about it.

Like those are huge. And I noticed a drastic difference in the days or the weeks where I do less of those versus when I do more. And so it's almost like, okay. AI is there, but it's just one more tool in our kit. And the more we can lean into these other elements, the more we can, we can really amplify the core of what makes us most effective, which then allows the power of AI to be amplified right along with it.

Dave Dougherty: Yeah. And I think for me, this, this piece on authority. Versus leadership is interesting because you know, when we've talked about content marketing strategy and, you know, you can use all of the articles to or all the tools to generate all of these articles and that's fine. But that, you know, as. Old school SEOs, we know, you know, building spammy sites is a very short-term thing and there's always a way to game the system and it always fails eventually, right?

But building up that library of things so that people can know that, okay, this is coming from this individual. This is their particular take on it. Do I like it? Do I not right is going to be better for that. And then we'll lead to the opportunities for leadership or You know, being an authority on a particular thing.

So Alex, are you thinking deep thoughts? Do you have anything else you want to go on? You have that look. Yeah.

Alex Pokorny: Well, there's one other one.

Adapting Communication and Management Styles for Different Generations

Alex Pokorny: And I know it from some people in close to her managers of younger teams. And there's a generational difference between basically from kind of the millennials, Gen Z preference towards more task.

Focused kind of work versus more emotionally open kind of work, basically, if I could cut broad strokes here between kind of the top and bottom of that, and that changes throughout that spectrum of basically of how they respond well to different styles of leadership to. the way that they want tasks described to them, like how they want to be managed.

I mean, it changes drastically because the expectations that each one of those groups has gone through and over the course of their career has gone in very different directions. So substantively different cultures. Right now I'm basically managing a team of millennials and I've been, Trying to find more articles like this because I'll eventually be managing Gen Z and That's going to be a shift for me because I've leaned heavily into this much more technical side of things I need to basically be able to pick up those skills and I know that I know that's a deficiency that I got I got to figure out this kind of stuff too of How can I be more open-minded towards this?

How can I be more adaptable to this? And then what kind of things do I kind of need to be keeping in mind even though just dialogue in the way I communicate like it's real easy just to get real bullet point focused and that's not gonna work and Communication styles are going to shift. I mean, is it a heavy preference for email versus Text which I stay away from because I try to have a strong separation between work and personal I don't know

Go ahead.

Ruthi Corcoran: I was just gonna run with that thread for a moment because I find myself squarely caught in the middle of Five different types of communication styles and you have to do all of them simultaneously, even though my preference would to just be using, you know, team's chat all the time, like just teams chat means that's fine.

But no, I find myself very much caught in the, the sometimes generational preferences, sometimes team-based or organization-based preferences of Just this wide diversity of how we communicate, and that I think I am hoping we find sort of a Convergence of how we move forward because I think it's a huge time suck

Alex Pokorny: Yeah, there was a just quick funny story.

I used to work for a company that did a company retreat and there were a few people This small company a few people who came up with this presentation, which I think is one of the best presentations It was called Emojis for OGs And it was a Gen Z team presenting up to the leadership and the rest of the company and showing different emojis and saying, okay, raise your hands if you think it means this or that or the next thing, then that it kept on going and the shock and horror on the faces of some of the people in the crowd was just.

It was hilarious. I mean the idea of like if you end all of your chat messages with a period or not or with like ellipses, three little dots at the end, like what kind of feeling are you presenting forward and one manager who like Always was like, I need this, bam, I need this, done. There's just, she was really big about punctuation, but her team was just intimidated as heck because they're like, oh my gosh, she's so angry all the time.

It

Alex Pokorny: was just astounding because it was like this group realization of these hidden emotions behind the screen. You know, it's a mainly virtual company. Everybody's off in different states, even so, it's just really funny to see that happen. But yeah, those styles have to change are the way in which we speak about things.

But I think the mindset has to change too. I mean, even behind that of how are we going to present these ideas? How am I going to get my team on board with this? It's going to be very, very different from that. Authority is kind of driven here are the bullet points to a leadership more driven soft skill set.

Dave Dougherty: I know I know somebody who for a very long time thought Netflix and chill meant watching movies and relaxing

and

Dave Dougherty: was using that At work frequently.

And this is like, so now we know what you're doing. Okay. We just won't go there.

And yeah, it's interesting to hear, you know, so for me and, and reflecting on what's going on, I'm working so cross-culturally, you know, globally that, you know, it's kind of nice because everybody's on the same page where everybody's just. Like, hyper-focused on, am I communicating the correct message, will it be understood properly, you know, given varying levels of everybody's ability to speak English so that you don't run into the same sort of trouble spots of, well, you're always over-explaining everything to me.

Well, yeah, because I don't know. I'm trying to be as clear as possible, you know

Ruthi Corcoran: there's a different expectation set, which then allows everybody to be a little bit better. And I think also from what you mentioned, I think it's important, which is it sounds like the culture within what you're working just takes that extra second to think a little bit more about how they're communicating, which is not the case in a lot of social circumstances.

Alex Pokorny: And there are a lot of it is unique, kind of a break to be given to everybody. That's a much wider birth than you might give individuals who are in the same culture with different assumptions.

Dave Dougherty: Yeah, it's interesting.

Concluding Thoughts and Encouragement to Explore Further

Dave Dougherty: So I will encourage everybody to check out this article. I will put a link in the show notes. I think Harvard Business Review gives you like three free articles. So I'd recommend you use that. So links in the show notes on the webpage and hopefully. This was interesting.

I know for me, it is it'll be something we circle back on a lot, just with how everything's changing and where we find ourselves. So with that, I think we'll see you in the next episode of Enterprising Minds, take care and like, subscribe, share all the things and see you next.

Cheers.