Ep 147 Leadership: Judgment, Taste, and the Five Things AI Still Can't Touch

0:00Not too long ago, we probably all could have sat down and had a discussion around, is AI going to be a thing or not? Is this going to be the next NFT, the technology that has its moment and then fades away? Or is this going to really change the landscape? I'd say right now, we don't need to have that discussion anymore. AI is obviously here. And I think the real question that so many leaders are wrestling with right now isn't the question of whether do you let it in or not. It's what does this do to my leadership? How do I need to think? How do I include it in my team? And then ultimately, I think the thing that so many people are quietly wrestling with is how do I actually change my leadership?

0:50Do I just keep doing what I was doing three years ago and hope that nobody notices or do I evolve? And at a time whenever companies haven't quite figured it out, a lot of the landscape seems to change every day. that's not an easy question, but that's what I want to look at and talk about today is what does leadership look like in the age of AI? What are the things that we need to think about and how do we need to approach things? Some of the things the same and some of the things differently. So welcome to episode 147 of the crazy one podcast. As always, I'm your host, Stephen Gates. This is the show where we talk about creativity, leadership, design, and a whole bunch of stuff that matter to creative people.

1:33As always, usual spiel. If you've heard a show before or any show, you know it. Do me a favor. Subscribe, leave a review, share it with your friends, all that good stuff. You know it. We're not going to belabor it. But why now, right? And look, I think that for me, I've had so many conversations lately with different leaders, with different creative directors and other things like that, that they're sort of seeing a similar trend. I'm seeing it on my team. I'm seeing it in clients we work with, where it feels like the team output is up, right? We're doing a lot. We're producing a lot of documents, but like something just feels off.

2:17It feels hollow. And I think that whenever you really slow down, and I think we say the quiet part out loud, we all know what it is. It's that what we're producing is more output, but we seem to be thinking less, right? That AI seems to be kind of filling this gap where our judgment used to live, where teamwork used to live, where respecting other people's positions or expertise used to live. And the reality is, as we all know, is that that's not a tools problem. That's a leadership problem. And I've talked about this before with the trend of plausible noise, that specifically this is a failure to define what is the team actually for.

3:03It's a longstanding problem. I think that in the same way that during COVID, when everybody went remote, all of their cultural sins of every company came to the surface because if your culture was, you know, you only relied on seeing people in the hallway to get work done, you had a lot of problems. I think in the same way that for so many teams right now, if what your company values is only output, then you've got a real problem because there's no shortage of output right now. But there seems to be a real shortage of impact. There seems to be a real shortage of quality. There seems to be a lot of those sort of things.

3:38So what does leadership look like when execution is no longer your primary value? And I I think that this is something, especially on the design and the creative side, we struggled with for a long time. But I think that this is going to be a reckoning moment for a lot of people in a lot of different ways that we just we've got to stop leading that old team. Because, again, I think that in a lot of cases, I'm seeing leaders that are managing teams that just no longer exist in ways that don't have the value that they need. And a lot of this to me is, and it's interesting because I have to have this conversation a lot because even with me, whenever I built my agency crazy, it was really built to challenge this idea that like headcount does not equal quality.

4:31Headcount does not equal output or a lot of those sort of things. But I think that's what a lot of this comes down to is that headcount based structure was really built around executional throughput. Right. We need a lot of people to do a lot of work that we need a lot of sort of specialists and those sort of things. And at the end of the day, I think that AI, it hasn't added capacity. It's changed what the team is fundamentally supposed to do. And so I think that this is why for so many leaders and things like that, I keep trying to get them to hear me that if you have a team and if you have a roadmap that is mapped to executional roles, production designer, copy editor, layout specialist, WordPress developer, whatever, you're optimizing for the wrong problem.

5:22And again, I think that you have to start thinking about how are we going to transition to a different organization? Because I think the leaders that I'm seeing right now that are thriving, the teams that are doing the best, the ones who are ahead, this isn't about reducing headcount, right? And again, I think that's where a lot of people are getting it wrong. There's a lot of AI washing going on that this isn't about just get rid of everybody. and because i think in that case it's like oh how do we do the same work faster or something i i don't know i'm still trying to figure out what some people are thinking but look i think that what what the best teams are doing is that they redefined what the team produces and it isn't just executional output but i think what they're doing is creating irreplaceable thinking And I think the org chart question isn't who do I need to do this?

6:18It's what can only people on this team do that actually shapes, focuses, and really hones in on what are outcomes? And I think that's going to be the part that really becomes so critical here is the thinking is the decision is is so many of those sort of things. And for me, I think that's a lot of then we need to sort of ask the question of like, what does your team actually owe the organization right now? And I think this is the question that a lot of leaders are avoiding. Because there's on the other side of this conversation on the other side of what this is. There's a lot of coaching that needs to happen for the people on your team.

7:09There's a lot of sort of thinking about things differently. There's a lot of change for how you need to change as a leader. And none of that is easy. None of it is comfortable. Some people will take that coaching and really excel. Some people may really fight it and get left behind. This is always, I think, one of the most profound and most challenging moments in leadership is that moment whenever you have to sort of face the reality that there's a chance that the team that got you here may not be the team that you're going to need to get you to that next point in the future. It's a longstanding cycle as we look at organizational maturity.

7:48But I think that was the thing, right? Before AI, most of your team's value was probably really defined by quality and speed of execution. Probably more the latter than the first, but a lot of it was if you tried to do design thinking, you're going too slow. If you ask what the brief was, it was just get it done, get it done, get it done, get it done. That formula has been broken for a long time, but I think a lot of companies, and especially on the digital product side of the graph, learn the hard way. And again, I keep saying this, that producing bad work faster, not an advantage. But I think that what the team owes the company, what you owe your team as a leader is to understand that what is going to set them apart is going to be things like judgment and taste and content and connection.

8:45Because I think that those are those sort of things, right? Like judgment in that there are calls that AI can't make. And that's true for a brand and audience, for a moment, right? Like there's always going to need to be those sort of things of like, what are we willing to do? What are we willing to not do? How do we, again, this is what the entire episode on pre-mortems was focused on, was how do we get that moment of judgment in place? I think that it's going to be taste. And I know, especially on the creative side, the word like taste is going to save us, gets talked about a lot. But I think that taste, for me, is in a few different ways.

9:26I think that for me, it's mostly recognizing when something may be technically correct, but may be creatively, tonally wrong or unoriginal, or again, where we need to bring a different perspective on it, because the models tend to be good to sort of finding the middle of an idea. I think it's incredibly important to recognize that you need to bring context. This is history. This is culture. This is those sort of unspoken rules about what actually works here, because not every great idea is going to get launched by a company. There's a lot of nuance to how do you get something from the spark of inspiration to the reality of execution.

10:09That sort of context matters. And I think there's also just connection, right? Like the human relationships that make ideas possible, that make them get approved and to actually ship. That I think a lot of what this is, when we strip it back to just the execution, it should be like, oh, well, of course the best idea wins. No, it doesn't. It doesn't. Right. Like it's just we all know that most big ideas are made smaller and safer and that it is a lot of work to protect them and to do a lot of those sort of things. But I think there's also sort of a fifth one that leaders really aren't thinking about yet.

10:45And I think this is something I've tried to talk about on here a lot over the years, and I think it's something we need to take much more seriously, is that a lot of what it is going to be is that our ability to be systems thinkers and stewards of these models. Because that's the thing, right? When you think about it, your team just doesn't use AI. Or if you do, you shouldn't use it just off the shelf. You have to shape how it performs for your organization. You have to teach it. You have to give it feedback, whether that's to get it to write in the brand voice or to work in the way that you want or to understand your brand.

11:22There's all of these things every single day that you have to do. And who on your team knows how to train outputs, refine those prompts, build institutional knowledge? Because the thing is that that's not a tech skill. That's a leadership skill. And this is the thing that I find the most interesting is that in many cases, a lot of the conversations I have, the people that are the most resistant to AI being leaders are the ones who I think are probably the best equipped to be able to use it so well. Because I think that that's the sort of thing is that doing that training, giving feedback, having perspective, having the judgment, taste, context, connection, right?

12:03Like that's what really good leaders do really well. And I think that's something then that we need to sort of be aware of that that is our role to step up into that. And because this is the thing is that right now, too many teams just they treat a like a vending machine, right? Like they bring a sort of a search mentality to AI that I'm just going to type something in. I'm going to take whatever it tells me and then I'm just going to go paste it into whatever I needed to do. And my thing is just like, look, if you're going to have a vending machine approach, you're going to get vending machine results.

12:38And I think that that's one of those things is that it is how do we be involved in developing these models, in owning them, in maintaining them, in how do we – from everything from how do we use them to making sure that the output is right, to understanding that there are jobs that were never part of our core value. and that's the thing is that none of this stuff that we're talking about i'm seeing on any job descriptions and that is as a leader i think to do two things one is to recognize your role and your skill set probably has far more value than what you thought and how you approach ai but also like this is your job to to fix right like this is some of the stuff you've got to start to lean into And I think a lot of that, again, transitions back to like, how do you position your team's value?

13:27Because this has been the longstanding thing. And I talk to leaders again all the time. They don't like to engage in uncomfortable conversations. They don't like to push back on colleagues who are trying to sort of define what their team is. And this is one immutable truth that I have found over the years is that either you are going to define your team, you are going to define your value and how you work, or your organization will define it for you. The latter never leads to outcomes that people enjoy, are good for your career, are good for your team. And that's the thing, right, is that if you are not defining your team's value in the age of AI, somebody else will.

14:09And I can guarantee you they're going to get it wrong. they're going to value the wrong things. They're going to disassemble the value of your team. And so look, all of this is, I think we're all aware of the pressure and the problems, but the heart of this is like, great, what the hell can we do about it? And here are the three things you can start doing today. One is to name what AI can't replace on your team, not in theory but in practice right like be specific that these are the things where we deliver value this is how we work with it this is what it cannot replace and you need to define it you need to tell it to your team you need to be able to make sure that that is integrated into meetings into presentations into how you talk about yourself right like do those sort of things To be on the way to do that, build some proof.

15:05Show where your judgment actually changed an outcome versus where AI would have gotten it wrong. Use examples, not arguments, not theoretical, not what do we think it's going to do. Actually show it. And that's one of the biggest things that, again, for creatives, we tend to be really bad where we just want to focus on the output. People don't want to hear about the process. They don't want to hear about you've got to show it. You've got to show your thinking. You've got to build these proof cases. We've got to, again, do more about decision logs than just reviewing output. And again, I think that a lot of what it is then is also start to think about how do you position your team as a systems thinking or an editorial or a guidance or leadership layer, right?

15:51Where it's like, look, AI generates, humans decide that that is how we need to position it. We need to talk about how we're using it in our work. We need to be able to be transparent about this because that's the thing, right? Like you can't just be the production floor anymore, right? You've got to be the filter. And look, this isn't about arguing for or against headcount. It's about making the case for what a team actually does. What do we create? How are we open and loud about this? Because as it goes from you up through any layers of an organization, right? If you're a really senior executive, if it goes through a CMO or CTO to a CEO to the board, if you're further down an organization where there's a lot more layers, you have got to get strong on what this is because there's a decent chance that the meetings where this value and the future roadmap and those things are being decided, you might not be in.

16:53So you have got to make sure that people are crystal clear that you are on top of this, you are thinking about it and how you're approaching it. But I think that for us, it is also going to mean that we need to start to rethink how we build and develop a team. And again, I've talked about this all the time on this show, right? Like I'm a huge foodie, I love to cook. But more than that, I've traveled the world really seeking out the world's best chefs to understand how do they build teams? How do they build culture? How do you bring a kid who is brand new out of culinary school and put them into one of the world's best kitchens and have them produce at a level where they can actually contribute?

17:35And look, the interesting thing to me is that they all tell you the same thing, that you have to have a great palate. Do you have to be able to have eaten great food to cook great food? Because if you don't know what great tastes like, you can't make it, right? And I think that's the thing is that a technique can be taught. Technique can be taken over a lot of cases by AI and do those things. But a palate, that decision making, that judgment, that has to be cultivated. That's always been true for leaders. That's always been true for creatives. But I think that that's the problem is that for too long, too many of us have hired on technique and ignored the palette.

18:20And man, you just look at some recent car designs and a bunch of things like that and you're like, these are people who have hired creatives off of Instagram. But I think that in the world of AI, palette means do you know what great looks like? Do you understand what the creative process is? Can you tell the difference between output that is technically complete and work that is actually good, work that's going to move the needle on your business? Do you have a point of view, right? Not a style, a perspective, a perspective on problems, a perspective on what we need to do, a way of thinking about things that isn't like everybody else.

19:05have you ever been exposed to great work to recognize when something falls short right because I think that's the part of it that this is honestly kind of the core of how you need to work with and ultimately defeat plausible noise is to be able to say that's not good enough that thinking doesn't work yes it looks pretty but here's all the reasons why we need to put thinking into this, not just grab something that looks pretty. Because all of those things that we're talking about, that's not something that AI can give your team that has to be built deliberately. And that this comes back to another age old problem, where organizations like to invest in easier problems, they like to invest in process, they like to invest in sort of easier ways of doing things.

19:52That's why they focus on output, the output as much as an easier thing to focus on, than process, than palette, than judgment, than doing these sort of things. And I think this is where a lot of us on the leadership side have just either been beaten down or broken or given up or just taken the easier road. Or we just said, like, you know what? Fine. If you just want to be about the execution, that's what we're going to do. I'm tired of fighting. And it's a really hard, it's been a hard reality right now. It's been a hard reality, I realized, in my career, is in a lot of cases to create change, to do something differently, to deal with some of these problems, in a lot of cases, you almost have to be prepared to be fired to make your point and to create change.

20:34Because in too many companies, it seems like anything short of that just gets ignored, right? This isn't going out and being a raging asshole, but just saying, look, like this is what we believe in. And I think that that's what it is, because I just think in a lot of cases, a strong palate only matters if you have the conviction to cook that food in that way every single day. That just the palate, and I think that's why a lot of us are getting it wrong, because when we talk about, oh, our taste is going to save us, oh, our taste is going to save us, I just, I don't, it's not. That alone is not, right?

21:11Like, that's the first half of the sentence. The second half of the sentence we need to focus on is that it has to be our taste and conviction, our willingness to do the work, to change, to evolve to be able to do that. Because I think that's the thing that the cook who knows food, like it, it's just one of those things where just AI output is generic, right? But it gets approved anyway, because people either they don't have the palate, they don't care. They know that they're just going to be rewarded on shipping. But that's the sort of thing, right? How are we now developing our teams? How are we hiring?

21:53How are we doing those sort of things? And I think in a lot of cases, this is what it is to me as a leader, what you need to start looking at coaching, holding people accountable to are things like, can they think out loud, not present finished work, but actually walk through the real reasoning in real time for why things are getting done. That if they are just, again, if you're just getting briefs and JIRA tickets and whatever else that's just like, here's a bunch of output, that's not thinking. And for me, on the creative side, you've got to push back on that because those aren't problems I can solve whenever it's just, hey, here's an output.

22:31Can people actually push back on AI output, on briefs, on each other? This is one of the longstanding issues that a lot of design and marketing teams have, is that we tend to be the dumping ground where everybody's bullshit. They just send it like, Like, oh, design will figure it out. Oh, marketing will figure it out. But the thing that we forget is that whenever somebody brings you a bad problem, bad thinking, a bad brief, and that we take it on and say yes to it, we are agreeing that we think that we can find a solution to this bullshit. Whether you can or not, that their problems have now become your problems.

23:08And at the end of the road, nobody remembers who did the dumb thing. Everybody remembers, oh, it didn't work. So that's why this sort of pushback has got to be important to be able to do that. I think that can you learn your way through ambiguity? That right now there's a lot of ambiguity in role, in value, in output, in a lot of those sort of things that like how can you get in there and actually, like we keep saying, define your team, your role, what you do. Can you work with the model? right not just take its output can you iterate it can you train it can you improve the output not just prompt and take whatever comes off the shelf that that's a lot of this shift in thinking and in team development that has got to change we have to stop fetishizing the output and focus on these things and again I think that this has to start with the team you've got today you've got to start evaluating them you have to start coaching them towards this way you have to help them see what the future is going to be if they do not change, what the challenges are going to be.

24:17And that's often the thing is that this is not something that's going to be a challenge just in your current role or their current role. This is going to be no matter where they go. This is going to be trying to get a job. These are going to be the things that right now the best companies are looking at is they're asking these sort of things. But it's not going to be long before everybody else catches on to this too. And this is then, it leads to what is the hardest, the most heartbreaking sort of truth in this is that, look, the reality is that some people on your team probably aren't going to make that transition.

24:50It's not because they're bad. It's just, I think that their entire professional identity is built on doing things that either don't have the value that they think it does, that AI can do faster. And I think that it's real. It's painful. It's heartbreaking. It's not the first time a lot of us have had to go through this. But I think as a leader, that's what they need you to do, is they need you to name it. They need you to help them see that. They need you to sort of recognize that they are going to go through a really uncomfortable journey that's going to be filled with a massive amount of insecurity.

25:33And I think that that's the thing. The leaders that are failing the team right now, they're not the ones making the hard decisions. They're the ones that are avoiding these conversations entirely. And I'm such a big believer in just put the shoe on the other foot. If the roles were reversed, what would you want? And in a lot of cases, I think the kindest and the most humane thing you can do is just tell the truth. And I think that's the thing that I've learned is that in so many cases, even if I had to tell somebody that was hard, I've had to tell them something they didn't want to hear. If I had to say something I didn't want to say, if I was able to do it honestly with some level of humanity and some level, even if they didn't like it in the moment, I think in most of them, certainly not all of them in the long term would at least appreciate that I was willing to just be honest.

26:23Because that's the thing is that, And this is not a moment where as a leader, your job is not to protect people from change. It's to help them navigate it. It's to help them coach it. It's to help sort of be, and again, I always go back to like the best advice I ever got from my mentor was a leader needs to be three things. And this is one of those moments where you need to be all three. He always said, you need to be a lighthouse, a punching bag, and a lightning bolt. A lighthouse because you need to show people the way. You need to keep them off the rocks. You need to be able to help them see what's out there in the darkness.

26:54You need to be a punching bag to be able to help absorb a lot of the noise and a lot of the BS and those sort of things to help give them that sense of confidence. I always think for most leaders, at least 60 % of what you do, your team should never know about. And I think a lightning bolt, because sometimes you just need to energize people. You need to blow something up, right? Like you need to, that's why I have a lightning bolt tattooed on my arm is because of that. That's how I like to show up. But this is the moment to be able to do that. And so there are three kind of things that I want you to think about doing today, this week, no longer than this month, right?

27:31Because I think if you aren't already doing this, you've got to start today. I think the first thing is that you need to actually audit what your team actually produces. And whenever you do that, you need to be specific. I think you need to break it into a few different things. You need to look at what are the things that AI could do. What are the things that AI could assist with? And then what are those things that only my team can do? And at the end of that, I think you need to write all that out in a list. And then the sobering part will be, I think at the end of that, you need to honestly look at that ratio.

28:10That if the things that AI could do, if it could assist with is far bigger than what only humans on your team can do, you've got a lot of coaching and probably a lot of really rough conversations in the near future because you're not the only one that sees your team that way i think that these are the conversations that your leaders don't have with you these are the these are the conversations a lot of executives don't have with you is that they see that ratio maybe they haven't done it that explicitly but they feel it and i think this is why i've said before i think this is the ugly truth is that for too many teams and too many people, AI didn't take your job.

28:48AI just finally gave executives a viable alternative to do and to act on what they have thought for a really long time. It's hard to hear. It's disheartening to say. Again, but it's just, I think that's the reality of that. I think then the second thing you need to do is you need to have that kind of palette conversation, right? Like what are you doing to make sure that your team is exposed to great work, is exposed to great thinking? What are you reviewing in meetings? Because like this, it's just, it's not going to happen by accident, right? You have to point to other brands and say, look, this is the standard.