Episode 280: Leadership in the Age of AI with Molly Rosen

Darrin Peppard (00:00.62)

Alright, my friends, welcome back into the Leaning Into Leadership Podcast. This is episode 280. One of the biggest mistakes leaders make when they step into a new role is assuming that the skills that made them successful before will automatically make them successful again. But in leadership, it just doesn't work that way. The shift from contributor to leader, from player to coach, from expert to visionary requires an entirely different mindset.

And right now, in a world rapidly being reshaped by AI, uncertainty, and constant change, leaders who cling to old approaches, well, they're gonna struggle. That's exactly why I'm excited. That's exactly why I'm excited for today's conversation with Molly Rosen. Now Molly is the co-CEO of Project Next Leadership.

And in that role, she works with organizations around the world helping leaders prepare for what's next. Not just in title, but in mindset, communication, and in agility. This conversation goes deep into succession development, emotional intelligence, AI adoption, leadership trust, and why today's best leaders are the ones who are willing to ask more questions instead of pretending that they have all of the answers. Now before we jump in.

Let's pause for a moment and thank today's episode sponsor, Heytutor. Hey Tutor is more than just a tutoring provider. They are a true partner for districts working to create real, measurable impact through personalized learning. With the National Student Support Accelerator badge for high-quality tutoring, Heytutor delivers targeted support programs that help close learning gaps while strengthening literacy and math foundations across your schools.

And in a time when leaders are trying to balance innovation, staffing challenges, student needs, and rapid change, having the right partners matters more than ever. If your district is looking for meaningful academic student support solutions that align with the goals that you have to help your students thrive, I highly recommend you check out my friends at heytutor.com. Now, let's lean into leadership with Molly Rosen. I'll see you on the other side.

Darrin Peppard (00:00.886)

All right, folks, here we go with this episode. I'm excited to welcome Molly Rosen into the show. Molly, good to see you. I'm so excited to have this conversation with you.

Molly Rosen (00:11.492)

It's great to be here with you, Darren. We've really been looking forward to it.

Darrin Peppard (00:15.4)

Yeah, absolutely. So here in a minute, I'll give you an opportunity to maybe tell the audience just a little bit about you. something that's been kind of sticking in my mind that maybe I'll share to frame our conversation a little bit today. Recently, one of the leaders that I work with was talking with me about how she was struggling a little bit with getting others

kind of all working towards the same thing. And a part of what we hashed out as we went through this conversation was she was still, I guess, injecting herself back into the roles that she used to hold instead of focusing on that leadership role that she's in now. I know that's indirectly or directly that we're going to talk about today on the show. So with that, I'll give you an opportunity

Tell our audience if they don't know Molly Rosen a little bit that they need to know about you.

Molly Rosen (01:17.938)

Yeah, thanks, Darren. So I am a co-CEO of a company called Project Next Leadership. And the work that we focus on is succession development. So that is helping leaders to prepare for and succeed in that next level.

wherever they're going next. So we tend to work with leaders in the corporate realm, but this is true for leaders in any realm. It's just thinking about that leadership pipeline. So we work with director level through C-suite, knowing that it's different as you get to these different levels. And often we don't know it until we get there. And sometimes we really don't know it until we step in it and realize that, OK, this is really a different role than what we've had before.

So our company works with larger firms who build rather than buy talent or build and buy talent. so this is kind of what we do every day. So that example of what you just gave is really, common of how do you get out of

what it is that you've done that's made you successful, that got you to the role where you are right now. It's a very classic issue and that doesn't mean it's any less difficult to not do it and to repeat it like people have before us. So I think it'll be a good thing to talk about.

Darrin Peppard (02:43.17)

Yeah, absolutely. Well, and just listening to you talk about that makes makes me think about a couple of things. You know, what what I've experienced even in my own leadership career, you know, and of course, I was in the K-12 education space. And, you know, when when you move from being a teacher to being a building level administrator, usually it's because somebody taps you on the shoulder and says, man, you know what, you ought to think about being an administrator. You'd be a great leader. But the skill set that

allowed you to be really good in the classroom and the skill set that's necessary to lead a building are two completely different skill sets and they don't easily transfer. I'm curious, certainly in the corporate space, I'm sure that there's some definite correlation there between the role here and the next role.

getting too granular on this. What are some of the things that you notice or that through your work with your company that you've identified that what we need to be thinking about, one skill set to the next?

Molly Rosen (03:55.356)

Yeah.

So I'm thinking about when you go from kind of individual contributor to the manager role and then manager to senior manager. So we'll kind of start with those. you're moving up, as you said, it's a very different role, even if you're a player coach kind of role. you can imagine in a school system where you've got maybe the head of the pod of teachers, right? Like at my kid's school, we would have like the three second grade teachers were a pod and the third grade teachers were a pod, et cetera.

So there's different roles, kind of those coaching roles. So that's different in terms of we're not always the problem solver and we shouldn't always be the problem solver. We're trying to develop capacity in others to be the problem solver. And it often feels really good to be the problem solver, right? To be the one doing the work, to be the one who can figure out the challenging things and they're, ooh, they're bringing something to me. So that means that...

to show my value and to feel valued myself, that that is what I do. And so stepping back from that is an identity shift that we need to go through. What it looks like later.

And I know you've gone through this, Darren, with your own career is when you're going through and the job's getting bigger and bigger and you have people reporting to you that are doing jobs that you've never done before. So that's even a whole different thing because then it can really feel like imposter syndrome that here I am leading people who are doing jobs that I haven't done. so in an extreme situation where you've got a CEO who's leading a company and functions that they've never been in before and regions that are under them.

Molly Rosen (05:40.353)

that they've never worked in before, that imposter syndrome really comes up. So there's just, different levels of this and different challenges at different levels as we move up and realizing that, you know, we may be strong leaders, but we may not be strong leaders in this next role because it's a different skill set and it requires a different way of being indifferent at different levels.

Darrin Peppard (06:08.225)

Yeah, you said several things in there that I really appreciated, but one that resonated, and I just read an article a couple of days ago about the player coach concept. And I know it's not a new concept, but it's something we're seeing more and more in the corporate space, in the nonprofit space, that we're...

we're seeing this almost duality of a role versus just the manager or the boss.

in your experience or what maybe you're seeing right now, how is that player coach role translating in terms of helping not anchor people in just the, well, I'm the boss or the, wow, this is what I used to be good at.

Molly Rosen (07:01.968)

Yeah. So as you said, Darren, it's not new. It's probably just as common now as it ever has been, perhaps more so. In fact, there are organizations, again, going back to maybe we don't even need managers, which is kind of

because of course Google tried to do this maybe 15 years ago and they ran a whole experiment because they're Google and they do these things and they realized that yeah actually we do need managers. So they did a whole study on this and realized that they need managers but you know whatever whatever's old is new again and people try different things.

So what ends up happening, and I don't know if this happened with you, Darren, is when someone's a player coach, what do you think they're going to lean on more? What do think they're going to do and feel more comfortable with? They're going to bleed into the player.

Darrin Peppard (07:53.495)

player. Yeah.

Molly Rosen (07:54.033)

Right? Because they know it. They've been there. It's comfortable. We all love checking things off the list. Right? We just do. And so often when we're playing that coach role, there isn't that feeling of the end of the day of like, achieved things. I got stuff done. And so it's A, it's a new skill set. B, it doesn't feel as achievement oriented. And C, it's like it just it feels right.

Right? It just feels right to us. And so what happens in that player coach role tends to be that there's a lot more player, there's a lot less coach, and there's just a little more mayhem. Now, sometimes that's not the case, but that is pretty often true. And that player coach role at this point is getting higher and higher in the organization. And it's a challenge because leaders are having a hard time making time for...

the manager role, the one-on-ones, the leading the team.

that communicating the vision. It's doing the stuff, like seeing your role as one that is pointing the way to where we're going when, frankly, most leaders don't know exactly where we're going right now because things are changing so, quickly. But being able to clear away obstacles, being the one to clear the way by talking to people in other departments and getting the resources. mean, these are the things that managers are supposed to be doing.

knowing that it's a harder job. Those are harder things to do. And so that's why they often get, they fall along the wayside, which is why there's kind of, there's a lot of churn going on in organizations right now. And I don't mean just people turning over. mean, just there's a lot of miscommunication. There's a lot of vying for resources right now because there is an...

Darrin Peppard (09:38.689)

Right.

Molly Rosen (09:51.011)

aura of and feeling of fear and anxiety. We know this, right, in the world that we're living in right now. And I just learned a term the other day called phobo, fear of being obsolete. So that fear of, my job gonna get taken over, is really resonant right now. And leaders need to be aware of that.

Darrin Peppard (10:16.877)

Yeah, but I think that's where the work that you and your company do with succession development that can at least help alleviate some of that. when I think about, when you brought that up earlier, you were talking about succession development, what it made me think about are two very specific things. So you're gonna have three options when I'm done talking. You could either say, Darren, you're crazy, you completely misunderstood me.

Or you can choose either of the two things I'm going to share to chase after and let's see where it goes. I hope you don't go with Darren, you're crazy. That's not what I said. when, I'm giving you the opportunity. So, so when I think about succession development, I think about, I think about really two things. One is being intentional as an organization of growing our leadership bench. How do we ensure that?

Molly Rosen (10:49.522)

You

Molly Rosen (10:55.824)

Well, you know, it's always choice A, but we'll see.

Darrin Peppard (11:16.801)

that the talent we're seeing in our organization, either in the individual performer that we see potentially moving into a management role or somebody in those management roles moving into a more senior role. I think that's an extremely important piece that some organizations have been very intentional about who they've really thought it through. We need to be doing this so that

when the churn happens with the human capital, we're ready. We're not just saying, boy, what do we do next? The other thing that I think it really sparks in my brain is as executive leaders, we have to be able to, I call it balcony level leadership, getting up on the balcony, getting to 30,000 feet, whatever you want to say, and being aware.

of our organization and understanding that when someone moves into the role, there's going to be this, hey, my skillset doesn't transfer. I've got to develop. I've got to grow. But how do we do that intentionally? Really the two tie together or again, option one was Darren, you're crazy and none of that made sense. I'll let you chase whichever direction you want to go with that statement.

Molly Rosen (12:36.242)

I'm not taking option one. yeah, so I'm going to start at the balcony because I agree that broader picture and of course, the higher you go up in the organization, the higher you are in the balcony and there's more to survey.

What is happening right now and what is so complicated is you've got AI is a part of the organization, right? And the stats around AI adoption right now are fairly abysmal, actually. It's not going well. People are talking about it with their investors, but...

the, you know, phobos that I mentioned, and there's lots of reasons that we can go into that this that is going well yet. But, you know, it's going to take time. And your listeners are probably also thinking, yeah, I'm not sure if I want a lot of AI adoption. It's coming. It's here. It's not even just coming. It's certainly here. And for for when people are using it.

with the full expertise that they bring as well, that combination of AI and human can be quite amazing actually, and fun even actually at times. But when we're up on that balcony, what we need to be looking at right now is not just the work that needs to be done and the people that we have to do it, but the technology as well. so...

What this looks like right now is how do we frame, right, as leaders, how do we frame where we're going and how technology and humans need to work together in our organizations? And it looks different in every company, but they've got to frame it. And the resounding frame that leaders have been putting forward lately has been we're using AI and we're letting people go. Well, that is very, very short-term thinking because every organization is going to have

Molly Rosen (14:33.902)

AI. The question is, who are the people who are going to be left? And it's the people who are going to be left who are going to make an organization successful because at some point people want to talk to people. So yes, of course there's going to be AI in every single organization, but if that's all your...

planning on, that's what you're leading on, people will catch up with you. It will happen. So the question is, do you have people left in your organization who care, who know how to get along with other people, who know how to work with other people and know how to lead? So it's a lot of this is, how do we frame? Why are we doing AI adoption? I went there because frankly, that is the world that we're living in right now. So what's the frame? How do AI and humans work together? What is our identity as an organization with this?

Darrin Peppard (15:16.407)

Yeah.

Molly Rosen (15:22.644)

What is the structure that we need? So if I'm up on this balcony, what is the structure that we need to be able to make this happen? And a lot of that is that we need different parts of the organization to work together differently. So whether you're in a school, whether you're in a company, that's siloing that has been so typical.

You know, it's it's never worked well, but it's blowing up everywhere because you cannot implement AI in a silo. It doesn't work right when you're having data here and data here and data, you know, like all over the place. And it's not communicating and not getting to the experts who need it to be able to see what the output is of AI and whether it makes sense and to question it. Right. Because you can't just take what comes out of AI and believe it. Because, of course, it's not, you know, we need to use our

our brains. this framing plus reorganization plus then evaluating how things are going, like this is what's needed and this is what leaders need to be able to do so that ability to be able to communicate where we're going, helping people to understand you can be part of this with us if you're willing to be agile, come along and re-skill. And if you're not, you're probably

going to be obsolete. It is true. But there is a lot of place for people if they can learn and be agile and learn to work with AI.

Darrin Peppard (16:50.131)

That makes so much sense. it makes me wonder, especially in the AI-driven world that we live in now, technology is changing at an unbelievably rapid rate. So if I'm leading an organization and I'm reaching out to you, how do we ensure that we're developing those plans that

We're not building a plan that's obsolete by the time we get this complete because things are changing so rapidly. I love that you talked about getting different parts of the organization to work together in ways that they haven't previously. What are some other strategies that are really critical so we're not building a plan that basically we might as well put on the shelf because it's going to collect dust?

Molly Rosen (17:43.799)

100%. Well, any sort of five-year plan right now is out the door. I mean, forget it. But what we're seeing, I mean, the whole notion of like an AI czar, and I know that's not where you're going, Darren, at all, but that's kind of obsolete, too. It's looking, there are leaders in every organization right now that are the ones who are adopting and trying to move fast. So it's looking at who are those leaders, and it may not be who you expect, but who's trying to move and how do we

Darrin Peppard (17:55.147)

Right.

Molly Rosen (18:13.692)

equip them and have them help in creating this plan. a lot of this, mean, AI adoption has to come from top down because there has to be a vision for the how and the reorganization.

Agility is the name of the game right now. we need to, it's something we call lily pad leadership. You know, if you are at one side of a pond and you're trying to get to the other side of the pond, you know, it can be hard to see that other side of the pond these days, but you can see the lily pad that's right in front of you. And then the one after that, and then the one after that. So it's, here's the vision is we are going to be a company or an organization that leverages technology in a way that supports our

our our students, you know, whatever, whatever's at most, who are you serving? And be able to support our staff.

our teachers, our employees, by helping to ensure that they are doing the work in their zone of genius, the work that only they can do. So this is the frame. So that's kind of the bigger picture. We're doing it within the context of our values, right, as an organization. And so that's the bigger picture. Now, the how specifically, yeah, we may reorg to this first structure.

And then we may realize six months down the line that actually there are some things that don't work. it is this, don't think we can promise as leaders that we know exactly what this is going to look like, but we know the why and we know the how in terms of values, in terms of what we care about. then, so some of the what is going to change as we go. So that's what leadership looks like now, that we don't have all the answers. We've never had all the answers as leaders, to be honest.

Molly Rosen (20:06.546)

to recognize that any strong leader is going out with as many questions for people as they are going out with answers, right? Because, I mean, nobody knows. And anyone who pretends that they do is fooling themselves and fooling everybody else. Because, well, they're probably not fooling everyone else because everybody knows that. No one knows what's happening a couple months from now. But that agility is the name of the game right now for leaders and for the people who follow them.

Darrin Peppard (20:25.613)

That's very true.

Darrin Peppard (20:32.525)

Yeah, absolutely. Now, what I just collectively heard you say in that specific context, but on a much broader context with leadership, is very much gone are the days of the leader owning all of the knowledge and then just giving the directive.

I heard you say one of the most important things we can do right now as leaders is to empower the people around us to listen to the people around us and to give them their their opportunity to own the direction we're going to go. And the direction we're going to go is driven by our values is what I really heard you say there. So that was just like, that was an absolute masterclass in leadership right there, Molly. I think that was absolutely fantastic. I love that.

Molly Rosen (21:19.602)

You summarize that perfectly, Darren. It's true. I mean, we like to talk a lot about this idea of sketch-based advocacy. So what we mean by that is, you know, not coming out with, here's the polished PowerPoint slides of where we're going and the whole thing, right? Instead, it's, here's a sketch. Here's where I think we're going.

right now. And I'm putting this as a sketch because

while I'm totally confident we're going to get there, I also know that things change. And so I want input from others. So a leader can go to their executive team with this and say, here's my sketch. I need feedback from all of you. Okay. And then we're going to have something that's even better. People are already leaning in towards it. Right. So the sketch rates based advocacy is, a very different approach than this notion that we need to have all the answers. And the CEO of Nike, actually he made a

statement a couple days ago. And you know, the company has been struggling. So this is kind of a related but slightly different point.

But he said, you I know that there's a lot of frustration. I know that we've been talking a lot about how to get the business back on track. I'm paraphrasing. But he named the emotion. He said, I'm tired of it, too. But he named the emotion. He named their emotion, showed confidence that we're going to get there and said, and we want to be having fun, right? Because fun is, you know, it's kind of a Nike thing. So this combination of the humility of knowing that we don't have all the answers, being able to

Molly Rosen (22:58.676)

communicate generally where we're going, right? I mean, and the confidence that we're going to get there. But also the emotional intelligence to be able to say, this is how I'm feeling right now. And I imagine this is how you're feeling right now, because that builds trust. I mean, these are the things that we need to be doing. I've seen this everywhere where there's a lot of layoffs. I was telling you before I had a client that just got laid off today. I mean, there's just it's happening a lot of places. And I was talking to someone else, a leader who just laid off some

team members who said, you know, we've been talking about this for three weeks. I mean, can we just get over this and move on? And I get it. I get it. They have been talking about it for three weeks. They're under a lot of pressure. But the conversation that we had was, you know, how are

How are they feeling about it? How are the people who are surviving still feeling about it? How are the people who are still here feeling when they're looking at their colleagues having left? You have to make hard decisions. It happens. But if we don't name that and don't name how we're feeling, which may be, you know, I'm feeling the pressure of moving on and I'm also recognizing that you all are still hurting and you know, just saying it builds trust.

to be able to move ahead. So these are all the things that are critical in leadership right now. And not everybody's up for it, to be honest. I mean, it's not an easy role. And it's an incredibly important role right now. We need more people to be able to lead with empathy, humility, and confidence. And it's not as common these days as you might expect.

Darrin Peppard (24:20.887)

Yeah.

Darrin Peppard (24:36.597)

Yeah, absolutely. And like you said, I mean, that is just incredibly important. I think that's one of the big shifts, the big evolutions that we've seen in leadership as we've moved away from the stoic, you know, directive type of leader and much more to the one who I love that you talked about that, that, that, you know, sketch advocacy that to me, I think of it like

Here's my clear, compelling vision, but I know I can't get there on my own. I want everybody to help me shape that so they take it on and we together move forward that leadership now is so much more about being able to build a team than it is about that individual who's doing the driving, if you will, of the work.

Molly Rosen (25:17.51)

Thank you.

Molly Rosen (25:27.73)

Absolutely. Absolutely. there's apparently Mark Zuckerberg is working on an AI bot for CEO bot. So we were asked recently, what do you think about that? That's a longer conversation. But yeah, there's some things that certainly can be helpful, right? Hopefully asking good questions.

Darrin Peppard (25:42.529)

Yeah.

Molly Rosen (25:47.101)

But an AI bot is never going to assemble the team you were just talking about, Darren. An AI bot is not going to motivate a team to be able to work together, share resources, and figure out where we're going. There's a lot of things that we need to do as humans, which means that we need to be unbelievably strong communicators more than ever before right now.

You know, back in the day when things didn't change much, people stayed at the same companies, the businesses didn't change much, the industries didn't change much, the technology didn't change that quickly. It was a lot easier to know what was coming and a lot easier to be able to be that stoic, confident leader that knew what was happening because they'd been around and they'd seen it and they could see what was around the corner. You know, no one can see what's around the corner right now.

And anyone who's an AI expert, we're based in Northern California, but believe me, San Francisco, we see a lot around here. But any AI expert is actually going to tell you that AI begins and ends with people. That's actually what they say, because you can't have AI adoption without people adopting it.

whether it's your customers, your employees, what have you. So that's what it takes to be able to make this happen. And this is the revolution in our lifetime. I mean, it's crazy. It's as big as the internet. It's as big as electricity. I mean, this is what's happening. So it's that leading change is so critical right now.

Darrin Peppard (27:17.131)

Yeah, absolutely. Man, this is such a great conversation. I could just keep going and going and going on this. But we're at the point in the show, Molly, where I'm going to ask you the last question of the show, the same question I ask everybody here on the Leaning Into Leadership podcast. It's the Leaning Into Leadership podcast. So how are you leaning into leadership right now?

Molly Rosen (27:21.33)

I love you too.

Molly Rosen (27:39.227)

Yeah.

I would say, well, so I run a company with my business partner. This is the first time I've run a company before, which is a different role, right? We started this role six years ago. so leaning into it for me, something that I've done recently is used an assessment called the lateral agility assessment. We used it with our whole team, but we are all getting feedback. And so one piece of feedback that I'm leaning into right now, as you said, Darren, is

that I got feedback from my team that while they love the fact that I'm full of ideas, full of that idea of, you know, how can we make it better? What can come next? You know, etc. That that's a strength that like many of us, you know, when we've got a strength, if we overuse that strength, it becomes a liability. So what I'm working on is that, you know, I'm always looking at what that next thing is, but we have to sequence it.

And we have to like prioritize. So what I'm working on right now is really looking at where does this next idea fit into our priorities? Where does it get sequenced? Where are the resources? And to be better about that rather than just kind of the new idea generator and just piling on. So that's my learning edge at the moment.

Darrin Peppard (29:02.293)

Yeah, I love that so very much. That's fantastic. So Molly, people are going to want to get in touch with you. They're going to want to learn more about Project Next Leadership. What are the best ways for them to go about doing that?

Molly Rosen (29:12.526)

Yeah, yeah, you can find us at projectnextleadership.com or you can find me on LinkedIn at Molly, Molly Rosen.

Darrin Peppard (29:20.353)

All right, awesome. We will put links for all of that stuff down in the show notes for everybody. Molly, this has been so much fun. I've absolutely loved this conversation. Thanks for joining me here on Leaning Into Leadership.

Molly Rosen (29:30.788)

Me too. Thanks, Darren.

Darrin Peppard (02:26.155)

Man, what a great conversation with Molly. Super, super happy that she came and joined me here on the program. Make sure that you get down there in the show notes, check out all of her links, get connected with her, and with Project Next leadership. And now it's time for a pep talk. So I spent my week this week in Virginia working with one of the districts that I am fortunate enough to support. And during my time, I spent three full days.

in the district, but one of the days was a full leadership workshop. And half of the day I had everyone. I had the operational leaders, the instructional leaders, district level, building level, coordinator level. I had them all. And then the second half of the day I had all of the instructional leaders. What was interesting and what I really want to get at here in the pep talk is in the morning we did three different

reflection exercises. And I'll be honest with you, when I structured this particular day of training, I was a little bit hesitant. I was a little bit reluctant. And I even told the group at the start of the day, I said, you know, I made a bunch of changes last night. And I'm I'm curious to see where this goes. The feedback I got was incredible. And the reason that they felt so strong about it was the multiple opportunities to reflect.

not only on their own, but to reflect with others, to share not just within their own usual circle of influence, but to talk to other leaders and learn and learn ways that they and learn ways that they found success and things that they wanted to reflect on. You see the power of reflection isn't just in your own reflection.

But sometimes it's in sharing your reflections with others. It gives them opportunities to ask you questions that maybe push your reflection even deeper. It was such a powerful day, and I felt so good driving away and felt even better getting the text messages and the phone calls and the conversations the following day about the importance of that reflection. So my challenge for you this week, find some opportunities to deeply reflect.

Darrin Peppard (04:50.473)

On the year that you are closing out right now. If you're a school leader, a district leader, make sure you put the time aside and then find yourself a reflection partner, somebody else who will hold up that mirror to you and ask you a few really good questions to push you even further. Hey, that's what I've got for you this week, folks. Thank you so much for joining me here. As always, rate, review, and subscribe because that truly makes a difference. It truly drives that algorithm that gets leaning into leadership in front of.

and in the ears of more people. Get out there. Have a road awesome week.