Sidecar Sync

Empowering Teams, Embracing AI: A Blueprint for Bold Leadership | 66

• Amith Nagarajan and Mallory Mejias • Episode 66

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In this episode of Sidecar Sync, hosts Amith and Mallory dive into the intersection of leadership and artificial intelligence, exploring why growing your team is the true measure of a leader. Amith shares his decades-long journey of building organizations, candidly discussing the lessons learned along the way. Together, they discuss the critical importance of AI training for teams, why failing to provide it is "leadership malpractice," and the distinct challenges of leading in a time of rapid technological change. From actionable tips to thought-provoking insights, this episode equips leaders to bridge the gap between AI awareness and effective implementation.

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🛠 AI Tools and Resources Mentioned in This Episode:
ChatGPT ➡ https://chat.openai.com
Claude AI ➡ https://www.anthropic.com/claude
Google Cloud AI ➡ https://cloud.google.com/ai

Chapters:
00:00 - Introduction
06:08 - The Sidecar Vision: Growing AI-Literate Teams
13:25 - The Critical Role of Leadership in AI Training
19:19 - Amith’s Perspective on Leadership Mistakes
25:23 - Wartime Leadership: Leading During Rapid Change
39:45 - Why AI Training Is a Leadership Imperative
40:00 - AI Learning Resources for Associations
47:05 - Closing Thoughts: Preparing for the AI-Driven Future

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More about Your Hosts:

Amith Nagarajan is the Chairman of Blue Cypress 🔗 https://BlueCypress.io, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

📣 Follow Amith on LinkedIn:
https://linkedin.com/amithnagarajan

Mallory Mejias is the Manager at Sidecar, and she's passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space.

📣 Follow Mallory on Linkedin:
https://linkedin.com/mallorymejias

Amith:

As a leader, you have to do unpopular things at times. You communicate why you're doing it and then you do it. That's what a leader is. Welcome to Sidecar Sync, your weekly dose of innovation. If you're looking for the latest news, insights and developments in the association world, especially those driven by artificial intelligence, you're in the right place. We cut through the noise to bring you the most relevant updates, with a keen focus on how AI and other emerging technologies are shaping the future. No fluff, just facts and informed discussions. I'm Amit Nagarajan, chairman of Blue Cypress, and I'm your host. Hey, everybody, and welcome back to the Sidecar Sync, your home for content all about AI and associations. My name is Amit Nagarajan.

Mallory:

And my name is Mallory Mejiaz.

Amith:

And we are your hosts and we've got something really interesting for you guys. Today we are going to be talking about AI because, well, we really can't help ourselves, but we are going to be talking about something a little bit off the AI topic proper in the context of leadership, and I can't wait to get into that. But before we get into our exciting topic for today on leadership, let's take a moment to hear a word from our sponsor.

Mallory:

If you're listening to this podcast right now, you're already thinking differently about AI than many of your peers, don't you wish there was a way to showcase your commitment to innovation and learning? The Association AI Professional, or AAIP, certification is exactly that. The AAIP certification is awarded to those who have achieved outstanding theoretical and practical AI knowledge. As it pertains to associations, earning your AAIP certification proves that you're at the forefront of AI in your organization and in the greater association space, giving you a competitive edge in an increasingly AI-driven job market. Join the growing group of professionals who've earned their AAIP certification and secure your professional future by heading to learnsidecarai. Amit, how are you doing today?

Amith:

I'm doing great here in New Orleans. We're about to go into a deep freeze which has everyone in New Orleans freaking out. I think a couple weeks ago, when we were recording I think, you were getting snow in Atlanta and we're about to get. I think four or five inches of snow is the forecast for here in New Orleans and I think that's going to be interesting.

Mallory:

I knew it was going to be cold in New Orleans. I didn't realize there was actually forecasted snow.

Amith:

Yeah, my kids' schools are shut down tomorrow. They're out today for the holiday, of course, because we're recording this on MLK Day, on Monday, january 20th, but they're out for today and then tomorrow they're already canceled school. So the worst thing about snow in New Orleans is I've only been here one other time when there's been snow is like right after I moved here and it was a little bit of snow. But the worst part about it is, you know, our roads here in New Orleans are not exactly the best, as you know from living here for a long time, and when there's snow it kind of covers up the potholes.

Mallory:

You can't really see where the potholes are are, so that's a little bit of a problem. Yeah, if there was enough snow, maybe it would pack up the potholes and then you could actually drive.

Amith:

We would have smooth roads but I guess four to five inches, not too much.

Amith:

But New Orleans, like probably most Southern cities, is not prepared for snow, so they won't be. They won't have like salt on the roads or any of the things that Northern cities or mountainous cities are used to, and so it's really treacherous for people to be out there driving around, or even walking around on the sidewalks, because it'll be icy and slick. So hopefully people heed the notice from the local authorities, who have strongly recommended that people do not go out on Tuesday when the snow is flying. So we'll see what happens. Hopefully everyone stays safe and warm.

Mallory:

For sure.

Amith:

How are you doing out in Atlanta?

Mallory:

It's really cold today, right now 25 degrees, and I think this morning it was like 17. That's pretty cold. For me, I will say, being Louisiana born and raised, that's pretty cold. We thought we might get snow again this week I was actually just checking, but it doesn't look like we are shockingly enough. But yeah, I will say I'm kind of over the cold a little bit. It was fun because it was novel, and now I would like to just, you know, be able to go outside without bundling up. But things are well, things are good.

Amith:

That's good to hear. I totally agree with that. Like, if I'm going to be in cold weather, I want to be able to use it, and for me that means going skiing. So if I'm in somewhere, somewhere where there's no mountains and there's snow, I just it's cool, but it's uh, it's not nearly as interesting as if you have a mountain to go ski down. Uh, it was interesting last week.

Amith:

Um, I was in Florida, um in the panhandle, so not in South Florida, but in kind of the North, uh West part of Florida, and we were having a hackathon, uh, across blue Cyprus. We had 13 people come together from all over the place. In fact, someone came in from Canada but unfortunately he brought the cold weather with him, so we had someone coming in from Winnipeg and then we had people coming in from California and from all over the place, all over the country, and we had a great week. Our hackathon format is pretty interesting. We spend five or six days in a row basically writing code for 18 hours a day or so, and that sounds to some people like misery, but it's really really good fun, and so we get a lot done. But it was interesting because we always get a nice house somewhere kind of beach-like, so that you're on the water and it's cool, but not a lot of time spent outside, because it was pretty cold down there too 18 hours a day sounds like a long time to be working, amit, but you because it was.

Mallory:

it was pretty cold down there too. 18 hours a day sounds like a long time to be working a meet, but, but you say it was fun.

Amith:

I enjoyed it. I think everyone else did.

Mallory:

Did everyone else enjoy it?

Amith:

I think so yeah, everyone seemed to be learning a lot and doing a lot of cool stuff. So I think the thing is it's interesting is, if you're with that many people working on lots of interesting projects and sharing ideas, you end up learning a you end up doing a lot more than you thought you would, and so in five days you get a month of work done, so it's pretty exciting.

Mallory:

I think getting everyone in the same room working together toward a common goal or even separate goals, and kind of having that like collective human capacity all together, I think is really exciting. Amit, I know we actually haven't mentioned this on the pod yet, but we've had some really exciting changes on the Sidecar front. I think we've talked about a lot on the pod how we've been building momentum and growing and expanding at Sidecar, and if you all follow us on LinkedIn, you've probably seen all the commotion around Sidecar as of late. But we actually just brought on Erica Salmrench as our chief marketing officer, which we're so, so excited about. Amit, I'll let you talk a little bit about Erica's background. She worked at Rasaio prior and we are so happy to have her on the Sidecar team.

Amith:

Yeah, I'm really excited about Erica's role as CMO. I think she's going to bring obviously a ton of experience in AI, in marketing and in the association market to Sidecar. Previously she was COO over at Rasa and did that for a number of years. She's been with Rasa previously for over seven years and so she's one of the original team members there, and I asked her to come over to Sidecar because of the growth trajectory of Sidecar and we have some really exciting things happening at Rasa as well. But on the Sidecar front, we just have an unbelievable opportunity ahead of us to go and educate the entire world on AI, and that's our goal is to go educate every single person in the association sector on artificial intelligence in the next handful of years. So having Erica as part of the team is really a remarkable acceleration for us and we're already seeing that start to happen. You know she's only been on board since the beginning officially, but we've already seen some really great things happen.

Mallory:

For sure Everybody join us in welcoming Erica to the team if you see her, or join us in welcoming her on LinkedIn. But that's not the only new news we have at Sidecar. If you visited any of our links in the past few weeks, you may have noticed we have a name change. Well, not really. We're still Sidecar, but our domain is now Sidecarai instead of SidecarGlobalcom, which I'm personally a big fan of. Amit, I know you've been trying to get that domain for a while now. How long.

Amith:

We first started exploring that domain about two years ago and we finally got it. So it was a process, but excited to have Sidecarai. It really is a good fit for who we are and where we're heading. It's obviously a much shorter domain, which does matter a lot, and so it's just succinct and hits home in terms of what we're about. So I'm really pumped about it. I think it's a great move for us to have that domain live, and sidecarglobalcom will still work, but everything we do will be off of the sidecarai domain going forward.

Mallory:

Yep, I think it really fits us in this new year, 2025. Well, today we have a really nice conversation lined up for you all, a bit different from what we normally do. We are talking about leadership, as Amit mentioned, which has kind of been a focus for us in the month of January as the new year began. So recently we've been thinking about what makes an effective leader, particularly as AI reshapes, how we work and, of course, while conversations often center on metrics and KPIs, we believe there's a more fundamental measure of leadership success that often gets overlooked, and that is the growth of your people. So today we are diving into why developing your team isn't just a nice to have, but that it's a core responsibility of leadership.

Mallory:

Leadership and, amit, you have spent decades building teams and organizations and you offer a unique perspective on what it means to truly grow people in an era of rapid technological change. So I thought we could use this pod to kind of explore that topic of leadership, of growing your people, and then also to ask you and me some questions about kind of your own past with leadership. I know many of our listeners often come to me and talk about how has Amit done this, and I'm so curious how he approaches XYZ, so I thought this episode would be a really neat way to just ask you some of those questions and see what you think. So, first question being when did you first realize that growing people was more important than hitting business metrics?

Amith:

Well, it's actually not so much that one is more important than hitting business metrics. Well, it's actually not so much that one is more important than the other, it's just that I think the business metrics are the result of growing people. So to me, I started to realize that, I'd say, fairly early on. So my journey as an entrepreneur started in the early 90s, that's when I started my first software company and I wouldn't say it was immediately obvious to me that growing people was the core function of a leader, which I firmly believe to be true now and have felt that way for probably a couple of decades. But I had some intuition around it, because what I found even early on was that if I could take someone in who had the aptitude and the attitude, I could train them to do just about anything. So they have to be obviously capable in terms of their raw intellect. They had to be willing to do just about anything, to learn and to grow. And that's what I always found very successful is kind of finding the raw materials and then molding and shaping so that the business's needs were met, of course. But what ends up happening is when you take people who are both obviously smart and obviously have a hardcore work ethic they've got to be intense to work in any of these companies and then you mix that with a lot of different kinds of experiences, including some significant challenges, and, most notably, put people in positions where they can succeed, but they're challenged to do things that they themselves probably didn't think they could do. That, to me, is where magic starts to happen, because people grow in these amazing ways when they realize they can do a lot more than they thought they could. That, to me, is what coaches do. That, to me, is the fundamental function of a leader is to see more in your people than they see in themselves at times and then to help them achieve those, those bigger things. So I started figuring that out fairly early because I had those experiences. I kind of stumbled into those experiences and I'm like, oh, this is interesting. If we can do this at scale, if we can hire lots of people, give them these paths, they're going to really love it. I mean, some people will, some people hate it. Right, in our culture it's pretty polarizing in the sense that you're either going to really love it here across our companies or you're going to really dislike it really quickly.

Amith:

And we try really hard on the front end, when we're interviewing people, to find the right fit, which I think is important for any culture, to get the people that align with your values and the values include kind of this type of thinking right. Are you about learning? Are you about adaptation? Are you about intensity? Do you want to have growth as a person, or are you more on autopilot? And there's cultures that are cool with the latter.

Amith:

That's not our thing, obviously. We're always in startup mode, right, it's always day zero in our environment. So for us, we had to have to always find people that are interested in learning and interested in continually adapting, because that's just the name of the game for what we do. Again, not every culture is like that. I think most cultures could benefit from a bit of that, a bit more of that perhaps, but for me that's always been. You know, entrepreneurs tend to be like that. I think you know I've got a lot of entrepreneur friends and I pretty much see this as a through line with all of us is that you know we're always trying to drive change, because you know you don't start a new business typically to do literally the exact same thing other people have already done. It's very difficult to do that and be successful. You're typically looking to drive some kind of disruption.

Mallory:

It's easy to talk the talk, amit, but I wanna share with all of our listeners and our audience that you really do walk the walk here, because about three years ago at this point you interviewed me in a coffee shop on Magazine Street in New Orleans in person and you talked to me about growing people and how that was something that you were passionate about and I remember at the time wanting to believe you right.

Mallory:

But I didn't really know you at the time and I didn't know the family of companies, so I thought that sounds nice on paper, but we'll see how it actually plays out and I can 100% attest to everything that you just said, that you follow through on that, that you do believe that and that you find ways to pull things out of people that maybe they didn't know were within them. But you said you felt this way for a few decades. I'm curious if there's ever been a story in your career maybe earlier in your career where you didn't quite get that right, or maybe you kind of felt like you made a mistake as a leader that you'd want to share with the audience.

Amith:

Well, I've made tons of mistakes. I've made mistakes hiring people. I've made mistakes, you know, in putting people in the wrong positions at times. I've made all sorts of mistakes as a leader. So, you know, if we have multiple episodes of a pod, if people are interested in hearing kind of an encyclopedia of that I, of an encyclopedia of that I can. That's how you learn, right. I mean, it's just been a very long journey of making lots of mistakes and I'm going to make lots more mistakes and I'm fine with that.

Amith:

I think that the whole point of it is like for me as a leader and for me as an individual to keep growing myself. I have to keep pushing myself. So if I just kind of hit the play button on something I had already recorded, so to speak, it's not too interesting. I get bored really quickly and I want to move on, but also I'm just I'm not doing anything particularly useful. So I would tell you that some of the mistakes I've made in the past are being too aggressive and trying to put people into roles where they weren't a good fit. But I just thought I saw in them something that made me believe that they would be good at X, y or Z, and so the classical mistake and I've made this mistake myself more than once is you take your best performing salesperson and you put them into a leadership role to manage a sales team and you think, well, that makes sense, because they're a great salesperson, therefore they'll make a great sales manager. And oftentimes that's not the case. In fact, more frequently than not at least in my experience individual contributors in sales tend to not be great sales managers. That's obviously not always true. There are people who can take on that different role, but if you think about it, managing a team of salespeople is totally different than what an individual salesperson does. So I think you have to be very thoughtful about the personality styles that fit best in certain areas. You have to think about it from the viewpoint of team versus individual, where people's priorities lie, their personal values and how they align with roles.

Amith:

You know we talk about corporate values or business values at the organizational level, and those are things that ultimately are non-negotiable and they're critical parts of like people either being part of the company or not. But then there's subtleties within that or there's additional elements right, where some people are fit for the overall values, but their personal values may make them a better fit for some roles versus others. Obviously there's skills and then there's this thing called preferences. So people obviously have lots of those and so sometimes you know a leader says, oh, this person's gonna be great at this and this and this, and maybe they could be, but they just really dislike it even after giving it a try. So a good example of that is in my old company.

Amith:

We used to hire more MBAs out of Tulane University down here in New Orleans than any other employer and we did that for years and years and years. We hired a whole crop of MBAs out of Tulane every single year and it was great. And these MBAs would come out and they would have, you know, freshly minted MBAs. So they had finance backgrounds and they had, you know, marketing skills. They had all these things they learned in business school for two years of intensity at a very, you know, very high quality business school.

Amith:

And what I would do is I'd say, okay, I need you guys to all do sales, and they'd go. I didn't go to business school to be a salesperson. It's kind of like looking down the nose, kind of like, oh, I don't want to do that. And I said, well, listen what do you want to do in your career? Why'd you go to business school? Almost all of them would say, oh, I want to run a company, I want to run a division, I want to not be what you end up doing full-time every day. But if you're going to run a company, you have to know how to sell.

Amith:

And so we'd put MBAs through a sales process. They'd have to learn how to do sales, and not all of them liked it. Some of them left and that was fine, and some of the people that did stick around some of them actually went into sales full-time, some didn't. Some went into other roles, but the sales experience for a number of months was really an important thing for their development. So I don't know, I think the mistakes sometimes you make mistakes based on kind of misinterpreting how people react to things, and sometimes it's also based on how open people are with you in terms of how they really feel about something. A lot of people will tell me oh, that's great, yeah, I'm cool with this, and then you find out like a month later that they hated it and then they left or whatever. So you know that's going to vary by individual. Obviously, you get better at that over time, but you're always going to. You're always going to make mistakes if you're trying to push things.

Mallory:

I had a realization at the Blue Cypress Leadership Summit, which we've talked about. It's an internal leadership gathering that we host every the fall of every year in September in Utah, and it's incredible. But I had the realization of me sitting with you at this last leadership summit that you have pretty much, I believe, only worked for yourself like your whole career, and I think I asked you a question about how many job interviews had you done and you mentioned one in high school or something, and so I'm curious for you. I know you have spent decades cultivating your leadership, reading books, learning from mentors, but do you ever wonder if not having had that experience of having worked under someone has impacted your leadership?

Amith:

Yeah, for sure. I mean. I think that, first of all, every path has its pros and cons. You know, with me, when I was in high school, I kept getting fired from jobs. You know, I worked as a shoe salesman, got fired from that. I worked at a bank, I got fired from that and so and I also was entrepreneurial, since I was like really young, you know, throwing newspapers and doing car wash businesses and just anything I could think of to make money. So I always had an entrepreneurial element, but I just figured you know what, and I didn't get fired because I didn't show up. I didn't get fired because, like you know, I was late or anything like that. I got fired from all these jobs because I kept doing things a little bit differently. You know, I kept wanting to approach, like interacting with my customers a little bit differently. You know, I kept wanting to approach, like interacting with my customers a little bit differently. Not that I had any idea what I was doing back then. I was slightly less clueless back then in my early teens than I was, than I am now. But the point is is that I just realized, ok, well, maybe I need to figure out something on my own, like from the beginning, as opposed to like go work somewhere.

Amith:

I do think if you go work at another company, even if you have entrepreneurial ambitions, going to work somewhere for a period of time is a really good thing if you get experiences in the right places, right. So a lot of people say, oh, I'm going to go work for this big corporation because I want to learn all about big business and the brand attracts them to go work for a Google or a PwC or someone like that, and that can be a wonderful experience. But the challenge with that kind of experience tends to be that you end up in a very specific role where you do the same thing repetitively and you don't really see the breadth, you see kind of the depth of one specific thing typically, and so it can take a long, long time to really get the exposure across a business to understand it. If you're starting off in life at a very large company, for some people that's perfect, though I think starting like if you're going to go work somewhere, working in a smaller entrepreneurial company where you're given lots of different chances to try lots of different things, probably would be good. So if I had that opportunity when I was younger.

Amith:

I think that might have been great for me, you know. But you know, you never know. It's one of these things that's an interesting thing to think about sometimes. But the path that I've been on, it was helpful in a way to not have that experience because I didn't know what I wasn't supposed to be able to do. And that's actually one of the best things about hiring people right out of school is that they haven't yet been conditioned by other companies to not believe they can do something right. Like I hire these young people out of a computer science program and I give them a deadline that a lot of senior engineers would say there's no way I'm going to get that done, and they turn around and get done because no one had told them they can't do it. So obviously they have to be intelligent, obviously they have to work hard, but there's a lot people can do if they don't have this preconditioning. So anyway, I don't know if I've exactly answered your question, but I think it's been an interesting path.

Mallory:

Let's say For sure, I think to that point of limiting yourself. I think of when we launched the brand new sidecar website early last year and how we met with an agency and they told us well now, if you're launching a new website, right, that's going to take two to three months, maybe, is what they told us, and I had never done that before. And you and me said, well, no, I wouldn't necessarily listen to them, let's just see how fast we can do it. I think we turned that thing out and in two to three weeks, a new website, which, mind you, not saying it was like the most perfect website ever, but kind of. Once you start to get conditioned that things take a certain amount of time or that you shouldn't be able to do certain things, I do agree that that's limiting in a way that that's limiting in a way?

Amith:

Yeah, for sure, I mean it's. There's always frameworks for thinking things through that people have come up with over time and sometimes they can be very helpful. But you know, if you, if you break it all the way down to, is there any fundamental, like you know, reason why this can't be done differently, better or faster? A lot of times you find that it's just, you know, kind of the doctrine of the thing. Right, it's like how people believe and what's what's become the standard way to do it. And the website thing is a great example. It's like, you know, that's just how people think about these projects. But there's nothing fundamental.

Amith:

If you're willing to move fast, if you're willing to take a few risks along the way, I mean, perhaps there's less quality assurance than some people would like, but you know, I'm I'm a little bit less worried about that. For brand new sites that have, you know, traffic coming to them initially, you can very quickly pivot. So, yeah, there's definitely a different perspective there. But you know, for me a lot of it is if you're, if you have people, if you are a growth oriented culture and you have people on your team that don't want growth, you will fail. You can't take people who repel learning and repel growth and somehow inspire them to want to be, like growth oriented individuals. There's some people who just don't want that, and that's fine, you know, it's just for us they're not a fit right and there's, and sometimes you don't realize that until people start working for you. What I've gotten really really intentional about across our hiring process you alluded to it a moment ago about your own experience here a few years back is we get really like kind of upfront about like look, this is what this place is about, like this is what we stand for. Our goals are ambitious, we expect a lot out of people and like you really shouldn't come here if you don't believe in these things, because this is what your experience is going to be like.

Amith:

And some people would say you're kind of like scaring people off and the way you are, but it's not so much that you're. For people who are interested in the type of thing we do and how we do it, it actually becomes kind of like a magnet right. We end up having much higher likelihood of getting those people to say yes, they want to come here. And for those that aren't a fit, we make fewer mistakes, because when we have a failure, when there's someone who's come on board and we've said all these things but yet they've made it through and they're really not that, they're really not someone who likes to go and learn new things and move fast they're going to be gone within probably 30 to 60 days because we're going to realize it almost immediately and we're going to give them a shot at correcting course.

Amith:

But we're going to say bye very quickly because I don't believe in keeping people on board for any length of time if they're a poor fundamental fit. That isn't to say that if someone has a bad day or whatever, that you're letting them go right away. That's not at all what I'm saying. There has to be a lot of empathy for people's lives and integration of life and work, but the idea is, if someone's a fundamentally poor fit, you're doing them a horrendous disservice in their career, not to mention your company and all of your other team members. By keeping them on board, you're just going to destroy your culture and drag down the whole ship.

Mallory:

Full stop. I want to get to this critical gap that we've talked about when it comes to leadership, especially on the podcast, where the acceleration of AI has created kind of an interesting dilemma for leaders. So many leaders that we talk to recognize AI's importance, but there's a big gap right now between acknowledging it and then actually preparing teams for it. So we know AI training I think we can all agree will allow you to remain competitive as a business, but we also see this as a fundamental duty as leaders to provide that training to your teams. You've taken a stronger stance on this, Amit, referring to the lack of providing AI training for your team as leadership malpractice. We've talked about it quickly on the pod, but I'm curious what experiences have led you to kind of frame it in this way.

Amith:

Yeah, so I know it's a little bit of a strong way to describe something, but I really believe this to be true. This is not intended to be, like you know, emotional clickbait for people. The whole point about going aggressive with this this year and you're going to hear us talk about this a lot upset some people, and you know that isn't the goal. We don't want to upset anybody. But the point is is that if you are not preparing your people for the future at all times, in all situations, across all economic cycles and all changes in terms of technological disruption, you're failing as a leader. You have to expect a lot from your people, but you have to give them the resources to be successful, and there is no greater measure of a leader than what happens after the leader is gone. Once the leader has left, you know what happens because is the organization thriving, successful? Are there people there that have grown enough to take over All that kind of stuff right, or does the thing fall apart? That, to me, is the number one measure of a true leader. But while you're there, you can also measure what's happening based on the growth of your team. Are you promoting people into bigger and bigger roles because they deserve it, not because they've been there a long time, not because they failed at their individual contributor jobs. So, therefore, you move them into a management job so they can stop damaging the thing they were doing individually, which sounds like a joke but actually happens on a regular basis in lots of organizations for profit and not for profit. But you can measure that success based on the true growth of your people, and so what I believe is that you have to prepare your people by giving them resources. You have to go out there and say listen, we're going to not only give you these resources, but part of it is to demand that they learn new things, and the world is changing so rapidly that if you don't require your people to get on board with learning AI now, they're likely going to be unemployable in the near future. There is no task that will not be touched in some way by AI, and so if you want your member services team or your event management team or your finance team or any other team member to be successful in the future and I hope that you deeply care about that as a leader you need to get them up to speed, period. If you don't do that, I feel that you are failing your team and that's all there is to it.

Amith:

You know, in the world that we live in today, it is abundantly clear, as we enter 2025, that AI is reshaping most aspects of life and business, and so you have to prepare for this, and there's two ways I think you need to illustrate this. First is make those resources available and make them mandatory. Don't just say, hey, we've got this training resource for AI. We'd love for you to do it, but we're not making it required. That is not leadership to me. I don't believe that that is the way that you lead to the future. You have to demand that your people do certain things, and when there is a fundamental shift happening of this type of significance, you've got to tell everyone this is your job. We appreciate everything everyone else, everyone does here. You need to get trained, you need to achieve X in terms of learning, and you have to do it by this deadline and give them a firm deadline, probably fairly soon.

Amith:

Here at Blue Cypress, across all of our organizations, even though all of our people are fairly involved with AI, we're demanding that every one of our employees across the enterprise becomes AAIP certified, which is, of course, our own designation at Sidecar Association of AI Professional Certification by the end of this quarter and we're not directly saying this, but the bottom line is real simple is that people who aren't certified by March 31st will need to work somewhere else by April 1st, full stop. And we're saying that not to be jerks, not to be mean, not to be aggressive, but because we need these people prepared, especially in the role that we're in, obviously, as leaders in this technology, and most of our folks are so deep in AI that getting a certification for them is just a matter of going through the process. But a lot of them aren't, you know, a lot of them aren't in AI first kind of roles. So we believe it's critical for our own team and I'd love to see more and more associations do something similar. Obviously, we'd love it if everyone did our certification, but that's self-serving.

Amith:

The point about this isn't about sidecar. It's about there are hundreds of different resources for learning artificial intelligence. Pick one and demand it, require it. And the last thing I'd say about it is you, as the leader, need to do it yourself. So you shouldn't go out there and say, hey, all of you guys, you need to learn this stuff and it's real important, and I am going to sit back and know nothing about this and I'll know how to spell AI, but that's about it.

Amith:

That is not acceptable. So that's also a form of leadership malpractice, because people expect you, as the leader, to be competent. You don't have to know every single detail of every single AI model, you don't have to follow all the developments, but you have to be competent at the basics of what AI is about and how it's going to reshape the expectations of your member community and, therefore, how you behave as an organization. You have to know enough about it to be able to work competently with your teams and to be able to help them think about the world and think about business and processes and service in the age of AI. So you know, I don't think that there's any other way to put it, and so, yeah, I'm personally getting out there and being pretty aggressive about it, and part of it is is that I, on the one hand, 2024 was an amazing year, certainly for across the Blue Cypress family.

Amith:

We all the companies across the dozen, plus businesses within the family experienced record growth. Sidecar in particular had a phenomenal year. It's wonderful. But I'm actually also really disappointed in 2024 because I was hoping that a lot more associations would get really, really active with this technology, and I didn't see it. I think that there's still a very small minority of associations that are really doing stuff, so we need to get everyone going right now this year, because this stuff is moving really quickly. It's not about the technology. The technology is interesting to some of us. It doesn't need to be interesting to everyone, but if you aren't getting your people ready for an AI-first future, you are essentially guaranteeing that they are going to be irrelevant and that they will be unemployed within a matter of possibly months, but definitely years, and by the end of this decade, people who don't know how to use AI fluidly are going to be at an enormous disadvantage.

Mallory:

We at Sidecar have an interesting mix of associations who mandate the AI Learning Hub for their teams and then those that don't. You can kind of never tell. I feel like talking to different associations who will mandate versus who won't. But I imagine we have some listeners here, because I've heard this multiple times from uh contacts at associations that say we cannot mandate anything else to our team. They're overwhelmed. The more mandates we we mandate, they don't do them. They don't see the value. We'd rather encourage ai learning. Encourage AI education without forcing it. It makes me think of something that you've talked about, amit, before, which is leading in a time of war versus leading in a time of peace. Can you talk a little bit about that?

Amith:

Yeah, so when I've talked about that before, I referred to this really interesting and fun book called the Hard Thing About Hard Things by Ben Horowitz, who's one of the founders of the A16Z venture capital firm and he has a long entrepreneurial history preceding that and just super interesting book doesn't pull any punches, it's very much in your face and what he's talking about is the difference between a wartime CEO and a peacetime CEO, and the way you're able to behave as a peacetime CEO is a lot more collaborative, no-transcript, that mode. Sometimes the best peacetime CEOs are horrendous wartime CEOs and the flip side is is that someone who is an adaptive as a CEO and by the way, I say CEO it's any leader but someone who's a great wartime CEO who really thrives and is great at rapid decision making and doesn't mind ruffling feathers and all that can make for an awful peacetime CEO? So what I would suggest to everyone here is that we are not in a time of peace when it comes to business. We are absolutely in a time of war from a business perspective, and that metaphor kind of only goes so far. But the point about war versus peacetime in business is essentially the rate of external change exceeding the rate of internal change, right. So whenever the pace of external change exceeds the pace of internal change, you are on the path to obsolescence. And that's true for an individual, it's true for a business, and so the faster the rate of external change relative to internal change, the more likely you are to be in big air quotes war, and so that's what Horowitz talks about in his book, and I really believe that's true.

Amith:

And I think that most associations are built for peacetime. They've been around a long time, they're super comfortable, they're sitting on a lot of reserves. Their culture is fairly stagnant, if, to use like a very direct word, some would say that their culture is foundational and their culture is, you know, based on tradition, and some of that's great Like. I don't mean to like disparage tradition, but sometimes you have to really step back and say, okay, that's cool, but you know, are we going to be around in two years or five years, right? Are we going to be relevant? Are we going to be able to serve our audience? Independent of what you think of your association, the world around you is shifting really quickly, and if the expectations of your audience for your content, for your services, are radically different than what you're capable of delivering, you have a big problem.

Amith:

I mean, a good, simple example of this is member services. I've talked to a lot of people who say, hey, our goal for our member services department is to be able to answer inquiries within 24 business hours of when we receive something. And, generally speaking, people don't do that. In most of the larger organizations it takes a little bit longer than that on average, but their goal usually is one business day, which sounds pretty reasonable. It sounds pretty reasonable as of maybe, say, two, three years ago and perhaps reasonable to some people today. That will not feel reasonable very soon because people are expecting essentially real-time, high-quality customer service coming from what's obviously going to be an AI-powered future when it comes to the bulk of those kinds of inquiries. And if you're not figuring out how to do that, you're going to have a problem because people will go to the lowest friction solution, not necessarily the highest quality, not necessarily the lowest cost, but the lowest friction, that which fits into their work stream with the least amount of pain for them, and if you're a high pain experience, you've got a problem.

Amith:

My point about all this is coming back to people and culture and leadership and, you know, tolerance for pain. Essentially, you kind of have to look at it and say it's time for us to, you know, acknowledge where we've been, but agree that we're going to drive change and not do this through going through, like, a formal board approval that results in, like you know, the whole membership voting on a bylaws change. I mean that's going to take longer than you have time for, but that's where this, you know, there's a lot of discretion in all positions, including, of course, the CEO role, but others as well. You could be a department leader and you can stand up and say, listen, I'm requiring this for our team and you can have. You can go to the team and say I really believe this is critical. I need everyone here to do this in the next three months and I'm only asking you to do like in the case of the sidecar stuff that we talk about. It's like less than 10 hours of coursework. That's a totally achievable thing over the course of three months.

Amith:

It's not unreasonable to mandate that You're not saying, hey, I want you to go get an MBA or go get a PhD in the next three months.

Amith:

We just want you to have some basic competence and that, to me, is totally reasonable. So, going back to the wartime versus peacetime thing, to wrap up this whole commentary at wartime, which we are in, you have to be willing to make decisions that are unpopular and are aggressive or feel aggressive at times, and I think the people who are taking the more passive approach, saying that it's, it's, we'd like to do it, and just using a carrot, you know, you see, maybe see how that works for a couple of months, but then switch to the stick if you need to, because sometimes you have to have both. You're going to have a certain percentage of your employee population that's motivated. They'll say, hey, this is awesome. Out of my 100 staff at XYZ Association, 15 of them got the AI training Awesome. But what about the 85 who didn't? That's where I say you, as a leader, have to mandate that for the benefit of the organization and for the benefit of those individuals.

Mallory:

And if I were the motivated employee or one of them on your team and I felt like I was a part of an organization that was committing leadership malpractice maybe some of you listening to this pod I would probably want to get out of there. You know, I feel like there's only so much you can do at that point.

Amith:

Yeah, and I think a lot of people will try to drive change. You'll hear some people starting to, like you know, raise their hand a little bit to the extent that their personality style would enable that where they'll say, hey, I really think we should be doing more. But a lot of times, you know, then the kind of the party line will be well, you know, we can't mandate it, like we can't X, y, z, and I say, why can't you do that? Right, is there a law of physics that prevents you from mandating that? Of course not, you know. Is there what it is?

Amith:

It's tradition, it's culture, it's a lack of willingness to ruffle feathers right and upset people sometimes. But I think part of it is is that for the people that you don't upset like there's some people who just don't want to go do anything, and okay, they're busy, I get it, we're all busy, but they're going to be a lot less busy pretty soon when they're unemployed. So don't wait till then. Help them now so that they end up with a good future. And so the point I would make really boils down to this as a leader, you have to do unpopular things at times. You communicate why you're doing it and then you do it. That's what a leader is.

Mallory:

Well, hopefully, at this point in the podcast episode, you all are at least a little bit on board with the idea of understanding that AI preparation matters and is important as a leader. Now making it happen right, that's another thing, and we understand that. So, amit, what is the first thing you tell leaders who come up to you at conferences, at meetings and say, amit, I want to start doing this. I listened to the podcast episode, I'm ready. What do I do?

Amith:

The number one thing is awareness. People have to understand the why. People will get behind things. That if they trust their leadership, if they believe that the leaders have their best interests in mind and the organization's best interests in mind, and they understand the why, even if they don't agree with it, people understand fairly deeply what's happening in the world around them, what's likely to happen and therefore why we need them to adapt as individuals and why we need to adapt as an organization.

Amith:

A lot of people say, oh well, like, for example, we do this thing called the AI executive briefing and we provide that to organizations and it's kind of like this landscape view of AI. It's not about a particular technology like a chat, gpt or perplexity or whatever. It's more about the exponential dynamics, what's happening around us and why that's driving change at such a rapid rate, and therefore, like what's a reasonable way to interpret what the next few years are going to look like. And that is the most important thing for people to understand at a conceptual level, because then they'll realize that the whole world is going to change. It's not just oh, next year will be just slightly different than this past year, which is what it's been for most people their whole careers. If they understand that, then I think people will get on board with saying, yeah, I really need to learn this stuff. But a lot of people bypass that because they have this mindset that, oh well, that's kind of more of a strategic conversation. I'll only share that with my execs and then for the 10x number of people I have that are not part of the exec team, I won't share that with them. I'm just going to give them the tactical tooling where I'm going to teach them just one tool at a time and tell them to go do it To me. That's where you're missing an opportunity.

Amith:

I think everyone in the organization has the capacity to understand that and needs to understand what's happening in the world. So to me, it's awareness is the easy number one checkbox you've got to check and there's a lot of ways to do that and then from there dive right into okay, now we're going to take action. This is what's happening in the world around us, like it, don't like it, hate it, love it, whatever you, wherever you are in the spectrum of your personal belief about AI okay, great, now you understand that. But this is what's happening in the world and in order for us as an association, as a nonprofit, as any organization, to be effective in achieving our mission and effective as a viable, sustainable business, we have to be able to do these things differently, and therefore this is what we have to go learn right, so, but I think you get, and therefore this is what we have to go learn right, but I think you get to the. This is what you have to go learn. This is how you have to go.

Mallory:

Change your processes once people understand the why, and I've got to double down on that. I think sometimes people feel like the why might be obvious, or maybe they just say the why one time Okay, we're mandating AI education, here's why, go forth. But you, amit, have said leadership is repetition or something along those lines, and so saying that, why reiterating it, posting it up on the wall if you have a brick and mortar office? I think all those things are essential.

Amith:

Yeah, I agree, I can't remember where I heard this the first time, but I've heard this where times from different people that you're the chief repetition officer and you know that's the reality of what you need to do. It's partly it's not that people forget what you said, sometimes that's true, but a lot of it's just reinforcement, where you're saying, look, this is what it is, this is what it is, this is what it is. We have to go do this thing and we're all in it together. Right, that's the other. I think is also super powerful. So, you know, it's people in general.

Amith:

It's kind of strange actually, because associations oftentimes their primary function is professional learning, professional education. Yet most people don't want to learn anything after they graduate college or finish their formal schooling. They just kind of are resistant to it, and part of it is it's not that the capacity is necessarily lessened so much, it's that people aren't used to it anymore. You know, going back to school if you haven't been in school, like full time, I think would be really hard. I've never done it, but I imagine it'd be extremely difficult to go back to school full time if you haven't been in school for a while and I think, if you're not accustomed to doing any form of professional learning.

Amith:

If you never read books, if you never listen to podcasts, if you never take online courses or never do experiments right, it's really hard to do any of those things. But that's just like any other form of habit building process. You have to get started somewhere. And that's again going back to leadership imperatives and why we're using this intentionally, you know, kind of aggressive phrase of leadership malpractice is that now's the time to stand up and get going. There's lots of ways to approach this, but you can't do nothing.

Mallory:

Amit, if you were leading a small association right now that had no budget for AI education, what would you do? How could you kind of get around that with free resources?

Amith:

There's so many great free resources out there. I mean, we ourselves at Sidecar have tons of free resources. This podcast, our book, is available as a free download. We have lots and lots and lots of content. We're constantly publishing blogs and in addition to that, obviously, sidecar tries to make AI contextually relevant for the association community. So what we do is take AI principles and then tailor them to use cases, ideas and the culture of this market to make them as easily adaptable or easily understandable as possible in this space. But there's tons of generalized AI resources out there. Every major company out there has free AI training. Nvidia has free AI training, microsoft, google, aws everyone has free AI training out there. There's tons and tons of places to learn.

Amith:

It's not an issue of money. There are resources out there for free. There's also tools you can play with for free, right. There's free versions of ChatGPT and Cloud and Notebook LM and all these other tools. Of course, there's paid versions as well, but there's a lot you can do for free from a perspective.

Amith:

So it's definitely not a money issue. You know, obviously, if you're willing to invest a little bit of money, then you can get a paid course like what we offer. You can go to other providers and get kind of their premium offerings and it may not be a crazy amount of money relative to your budget, but you can start off with zero dollars. And when we say, like we at Sidecar want to go educate the entire world on the importance and the capabilities of AI for associations, we expect that 95 plus percent of those people who we help educate will never pay us a dime. You know, our intention is to provide the vast majority of our content for free to the whole world of associations. That's our mission at Sidecar, which obviously supports the broader Blue Cypress vision and mission.

Amith:

Of course we do have a premium offering and that's great, but that's not the whole point of what we're talking about. The point is you can go out there and do this so many different ways. In fact, that may be the challenge. Right, if there was like two options, you could go, look at the two of them and make a choice. Here I would say you know we have a great blog We'll link to it in the show notes that talks about training resources available for associations and AI. We published that blog several months ago. It's still relevant. Obviously, our own stuff is one of the resources listed there, but there's a bunch of other things in there that are totally free. So free is the place to get started.

Mallory:

Maybe you all pick a pod episode it doesn't have to be ours Listen to that one and do like a lunch and learn internally. Or maybe you all commit to attending a webinar at the same time. I think there's a lot you can do out there, with free resources for sure. Well, amit, it's been a fantastic episode talking all about leadership. Everybody, thank you for tuning in today. Go out there, learn AI. You're already on the right track by listening to this pod and help your teams learn AI. We will see you next week and help your teams learn AI.

Amith:

We will see you next week. Thanks for tuning in to Sidecar Sync this week. Looking to dive deeper? Download your free copy of our new book Ascend Unlocking the Power of AI for Associations at ascendbookorg. It's packed with insights to power your association's journey with AI. And remember Sidecar is here with more resources, from webinars to bootcamps, to help you stay ahead in the association world. We'll catch you in the next episode. Until then, keep learning, keep growing and keep disrupting.