Sidecar Sync

Getting Your Board on Board with AI | 82

• Amith Nagarajan and Mallory Mejias • Episode 82

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In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias take on one of the most pivotal—and often overlooked—challenges in association innovation: getting your board on board with AI. Drawing from Amith's personal boardroom experience and Mallory’s deep dive into board psychology, they break down how to navigate internal politics, craft compelling AI use cases, and turn skeptical board members into innovation allies. From emotional storytelling to small pilot wins, this episode is your roadmap to aligning AI ambition with boardroom approval.

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Chapters:

00:00 - Welcome to Sidecar Sync
01:00 - Setting the Stage: Why Board Buy-In Matters
06:55 - What Motivates Board Decisions in Associations?
10:15 - Volunteerism, Ego, and Career Goals
13:55 - Navigating Volunteerism, Legacy, and Tradition
25:37 - How Can You Build an Irresistible AI Use Case?
27:21 - Selecting the Right Pilot Project
32:59 - The Role of Demos and Emotional Buy-In
37:19 - Is an AI Data Platform the Right Starting Point?
40:34 - What’s the Pathway to Getting Board Approval?
42:53 - Building Support and Presenting With Impact
51:14 - Closing Thoughts and Next Steps

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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.

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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:
https://linkedin.com/mallorymejias

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Speaker 1:

Maybe it's not so grandiose, maybe it's just a couple of projects you'd like to kick off and you want the board's approval. But if you start with these little bits, I think you can go a long ways, and that's one of the coolest things. Like to your point, mallory. Ai is so vividly understandable when you demonstrate it. 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. Greetings everybody and welcome to the Sidecar Sync, your home for content at the intersection of all things artificial intelligence and the world of associations. My name is Amit Nagarajan.

Speaker 2:

And my name is Mallory Mejiaz.

Speaker 1:

And we're your hosts, and today we have an exciting episode for you that I think will be really compelling for leaders within associations all about how to get your board on board with AI.

Speaker 2:

Amit, I feel like we've been talking about this get your board on board with AI episode for a while now. What inspired you to bring it to the Sidecar Sync docket?

Speaker 1:

You know it's so critical in nonprofit organizations and associations especially, to have alignment and that's true, of course, for all organizations.

Speaker 1:

But with nonprofits and associations, having your volunteer leadership and especially your board of directors, fully bought into what you want to go do is critical.

Speaker 1:

In fact, the board largely sets the high-level priorities for most organizations.

Speaker 1:

So if the board isn't bought into AI and doesn't understand the importance of AI and kind of the significance of it in the world, the board is not going to be able to do its job effectively in governing the association and certainly in being involved in setting strategies.

Speaker 1:

So to me it's a really critical part because they're key stakeholders.

Speaker 1:

The board is there to represent the membership at large and in all boards of directors, whether it's a board of an association or a board of a corporation, they have a duty to the organization in terms of its long-term health and they're there for a very clear purpose. So having the board on board with AI is critical because you know, many people in the world still don't really understand the magnitude of what artificial intelligence really means for the world at large and certainly for their industry or for their organization or for their organization. So I think that's why it's such a key topic for leaders in associations, whether you're earlier in your career, or if you're leading an entire association and you're potentially working with a board that isn't yet on board with AI or maybe they get it, it's there but they're not really sensing the urgency or they don't believe it's necessarily the top priority. I thought it might be helpful for us to talk about it essentially for a while and talk about different components of what might help motivate the board.

Speaker 2:

Yep, it's a great idea and I'm excited to discuss it because, as I've told you, amit, I don't have a ton of direct experience working with boards in general, so I think this will be a great learning experience for me, too. To unpack, amit, in your experience working with association boards and directly with association leaders. Do you get the sense that boards right now are pretty open to the idea of AI? Are they putting up a fight against it? What's that dynamic?

Speaker 1:

I think that putting up a fight against AI is no longer the case. I think that probably was true a year ago. It's much less the case now. I think there's a realization in the broader world that AI is here and that AI is a real thing. It's not hype, maybe overhyped in some ways, maybe underhyped in others, but it's a real thing, it has real utility and it's changing the face of pretty much everything in our world. So I don't see boards fighting against it. What I see is that boards often still don't give it the face of pretty much everything in our world. So I don't see boards fighting against it. What I see is that boards often still don't give it the degree of prioritization that it should have.

Speaker 1:

Obviously, in our opinions, as people talking about the intersection of AI and associations all the time, we believe strongly that associations need to prioritize AI. So some of the things boards are not doing consistently or doing, I would say, somewhat rarely still is allocating additional funds, pulling from reserves and saying, listen, this is a moment in time that reserves are there for. The whole point of reserves is to protect the organization, surely, from potential issues like economic problems and things like that, but it's also to make investments in the future of the profession or the industry. And when there's times of radical change going on, the board should take action to say listen, we want to release some portion of reserves to make investments in experiments and in infrastructure to go build the future. And there's a lot of associations out there who struggle mightily because they have very restrictive operating budgets. And boards have the power to potentially unlock some of their existing financial resources to make experimentation and to make deployment of AI possible. That's one example.

Speaker 1:

Another one is just actually being supportive of the executive leadership having a little bit more discretion day to day.

Speaker 1:

Some boards are wonderful with that, where they really are much more of a governing body, but others actually quite frequently are quite involved in, I wouldn't say, daily operations of the association.

Speaker 1:

But the degree of approval required from the board for, let's say, purchasing decisions is quite granular and so that really slows things down. You know, when you talk to association leaders and they say, hey, I have to go get this approved by the board and it's a $10,000 or $20,000 purchasing decision. It's non-trivial, certainly, but it's, I think, well within the discretion of what certainly the CEO should have, and possibly even a divisional director or VP within an organization like that. So sometimes the structures are overly cumbersome, overly restrictive and don't really provide an opportunity for the culture to thrive in a little bit more nimble and experimental way. So these are some things I think boards could definitely be looking at. There's plenty more as well, but I would say, to answer your question more succinctly, boards are probably somewhere in the middle right now, but they need a strong nudge to the side of hey, let's go hard at this.

Speaker 2:

Yeah well, I'm excited to dive into this episode's topic. We're going to break this down into three conversations, more or less. First, I want to get into the nitty gritty of what motivates board decisions in general across associations and see if we can help listeners figure out what motivates their board specifically. Then we'll talk about the idea of building an irresistible AI use case that your board can't refuse and then we'll kind of talk about the pathway to getting that AI use case approved by the board in the end. So, first and foremost, I will say I had a little bit of fun with this first conversation, amit, because my background in undergrad is in psychology and typically on the podcast I am, you know, trying out new tools, I'm demoing things, I'm making new accounts with new AI companies. This one, I was kind of getting a little bit psychological. I was working with Claude in chat UBT to say if you were a board member, what would motivate you to serve on a board? Like, what do you really care about? So I wanted to, before we dive into the whole getting your board on board with AI thing, I wanted to figure out what drives board decisions and associations. So, unlike corporate boards focused primarily on shareholder value.

Speaker 2:

Association boards have a dual focus advancing the organization's mission and responsible stewardship of resources. Board members, as Amit said, are typically volunteers who deeply care about the industry or profession, bringing their own expertise and perspectives to the table. Frankly, this might be hard for you to hear, amit, but I would say your board may not care that AI is perhaps the biggest technological advancement we'll see in our lifetimes. They probably don't care about Moore's law or AI capabilities doubling every six months like we do. They care about member impact, strategic alignment, resource implications and potential risks.

Speaker 2:

Now, of course, each board has its own unique dynamics, but they all share common concerns when it comes to significant technology investments. Will this truly benefit our members? Is this the best use of limited resources? Do we have the capacity to implement this successfully and can we measure whether it's working? Successful proposals address these core concerns directly framing AI not as tech for tech's sake, but as a strategic solution to member needs and your organization's challenges. So, amit, I know you have served on several boards or currently still do. I am curious what motivated you to take on those roles.

Speaker 1:

Boards that I've served on in the nonprofit sector are primarily focused on either some cause that I was focused on personally, or something community related, where I was trying to give back to my local community and my motivation has been to just, you know, help out in some way. And I think a lot of volunteer leaders in various different types of roles, including board roles, specifically have that same motivation. So people tend to care deeply about the profession or the sector or the industry that they're in, and that's extremely important. And that is the key commonality that I tend to see across different organizations is that people are volunteering their time. They're typically busy people, so that's one piece.

Speaker 1:

Another motivation that I think is quite common is career advancement. So if you are in a particular industry and you are a volunteer leader, especially if you're on a board, and you know that means what are you doing? Well, you're spending your time collaborating, connecting with other people who are probably pretty far along in their career in that particular profession. So it can be quite good in terms of increasing your that particular profession. So it can be quite good in terms of increasing your visibility in the sector. It can be quite good in terms of creating potential direct opportunities, and so there's definitely an opportunity there. And I say that not because I think it's a bad thing at all. I think that's just a natural part of the duality of some of these motivations that exist. But I think in some cases actually that particular motivation may be stronger than anything else. I've definitely seen that myself with people where there's a lot of ego and there's a lot of interest in kind of advancing their own I wouldn't even say agenda, but it's more of their own kind of fingerprint on things.

Speaker 1:

So this is particularly true sometimes when you get a new board chair or board president comes in, and oftentimes these terms which is that's an important concept to talk about for just a second is that different boards have different rules around how long the board serves, so something along the lines of like a term in Congress, but there's a term of the board. Sometimes boards you know kind of have rotating terms where different roles have, you know, two years or three years or sometimes longer. Typically it's a couple years as a typical term, and some boards have like an automatic escalation where you have like a president-elect or a chair-elect and then that becomes the chair and then that person becomes, like you know the immediate past chair, and there's this whole kind of ascension and dissension kind of thing built into the governance structure. And so some of those roles are actually even more important than the board overall, because they tend to have the political clout amongst the whole group to move the needle on decision making. And so the question is is like when you look at the overall board's motivation, then you look at those specific roles and their motivation.

Speaker 1:

A lot of times when a new board chair comes in, they're thinking, hey, how am I going to put my mark on this organization for the two-year term that I have? Some are much more of hey, what do I need to do that will really serve the industry? Some are much more of I'm a visionary, I think the industry needs to go in this direction, and others might have some kind of pet project or something. So it really totally depends. Just like, as varied as our personalities are, are the motivations behind why people would do such things as to volunteer their time on a board. But I think those are some of the common ones.

Speaker 2:

In my research. I definitely hear what you're saying about the deep care of the industry, but also that professional advancement piece, and I think when presenting a use case for AI implementation to your board, you can kind of tap into both things so kind of how it will impact your industry. But then also, if you do have someone leading your board that's trying to leave a footprint, as you said, or a legacy, tapping into that and saying how this could kind of change the future of the association, I don't know, that might be important on the motivation side.

Speaker 1:

Yeah, totally, and you know, the thing I would say too is boards tend to be primarily external facing. I think some of the boards do look to the operations of the association as part of what they need to keep an eye on or what they need to at least have some familiarity with. But typically the board they're there to represent the membership, they're there to represent the sector, and so they're focused on what's going on in the world of the members, what's going on in the world of that industry. And that's good. That's part of the value of a board is that there are representatives who work in the field. And so typically I think the motivation tends to be like how do we, as you said earlier, how do we better serve our members? But what are the issues our members are facing in their lives and in their professional roles day to day, week to week, month to month, that we as the association could or should be potentially helping with or doing a better job, with points where saying, hey, the association hasn't done a good job in areas A, b or C. Or maybe it's more opportunistic where, yeah, we're doing a pretty good job in all of our classical areas of service, but we could be doing these other things, and so it just depends in a number of areas like that.

Speaker 1:

The reason I bring up the kind of the external and internal piece is that a lot of association folks, the staff, tend to be focused on the internal issues, not exclusively, of course, but think about where you spend your time, and the people you talk to you tend to kind of reinforce the patterns that drive where your energy goes. And so if my job every day is to work within an association, running membership or running events, I spend a lot of time thinking about that naturally. So I think that's actually one of the sources of friction is that boards often want to spend more time thinking about the external world, and a lot of times staff is coming to the board with much more of the internal mindset from the industry. Once they're working in the role of the staff CEO or leader, a lot of times they focus on whatever the biggest fire is internally, which may have really, from the minds of the board, like no value or no importance, even though it's obviously critical to the operations of the association. So that's one thing to keep in mind.

Speaker 1:

Coming into this is that what's the perspective of each person around that table and you pointed this out earlier to Mallory that the board is a bunch of people, just like when you're, if you're selling something to an organization. There is no such thing as the organization. An organization is a made up fiction. There is no such thing as an organization. There is no such thing as a company or an association. In biology or in physics, it's just something we made up. So we got to remember that, like the actual creatures that are there, thinking and listening and interacting with you, are a bunch of individuals that happen to be organized at that point in time as the board, but they all have other things going on too.

Speaker 2:

Oh man, that's such an interesting point that you make and I'm sympathizing with all of our association CEOs, listening and executive directors, because you are the one straddling the internal of your staff versus the external with your board, and I cannot imagine how complicated that must be when you want to move things forward.

Speaker 1:

Yeah, it's tough. It's a really tough job. In your experience serving on boards, have you ever had to be part of a discussion around like a really big technology investment or something kind of that land, but also the bylaws and kind of the structure the organization has there, and the board has a duty to ensure that that is the case. That's one of the fundamental elements of good governance, but that shouldn't take the majority of the board's time. The board is a composition of smart people who have a lot of experience, and so they should be bringing ideas to the table, which isn't to say that they should be setting the agenda or the vision. That's ultimately the CEO's job, in my mind, and both not-for-profits and for-profits. A lot of times, though, the board does set the direction and the vision, but I do think that the board even when you have a strong CEO who wants to and is capable of leading the vision and the charge ahead towards that vision I believe the board should contribute ideas and say, hey, this is what I see in the world and here's some ideas, and so, therefore, the board should be having discussions about big strategic topics.

Speaker 1:

So, in nonprofits I've been involved with, we've talked about things like the fundamental economic engine of the nonprofit. What is the business model right? And so what I always bring to these conversations is like that's kind of a foreign concept. What's the business model of the nonprofit? Does that seem like an oxymoron? And in fact it's not, because all organizations, whether they're for profit or not for profit in terms of their style of tax return, have to have a business model if they want to be sustainable.

Speaker 1:

And far too many not-for-profits, particularly like community organizations, tend to be basically hand-to-mouth kind of thing, where they are basically out there asking for donations to fund way too much of their ongoing operations. And so the question is what kind of maybe recurring revenue model can we come up with? Is there a way to create some kind of differentiated value or some kind of product or a for-profit subsidiary that can generate consistent returns to fund the operations, so that we're less dependent maybe not exclusively independent, but less dependent upon things that we have less control over? So there's those kinds of conversations. Those are big discussions.

Speaker 1:

Ai tends to be something that I think could influence those discussions deeply. But yeah, I mean, the board in my experience is involved in that. I've also been involved in boards that I tend to very quickly resign from when they don't talk about this stuff and they're just talking about kind of the minutiae, because I feel boards like that really aren't adding value. So in cases where I've been recruited to join boards like that after a fairly short period of time, I've realized that's really what's the discussion.

Speaker 2:

I'm like look, I'm not adding any value, I'm out of here. Yep, you said something interesting that boards should be able to bring in ideas to the association. They are experts in their respective professions and industries. If that is the case, what role do you think the association leadership team plays in helping to educate their board on new technologies, emerging technologies? I know with our Sidecar AI Learning Hub we do have many associations that have chosen to provide that education to their board. Do you see're in the business of running an association?

Speaker 1:

You are the professional that knows how to run the association, and obviously you're always improving that knowledge, but that's what you do. So your board is the expert in the field and the profession or in the sector. You're the expert on how to run the operation of the association. And so part of that is you know, and the board might be you know, they might be bringing AI to you. They might be saying hey, there's this amazing stuff going on. Are you guys using it enough internally the association? That certainly is happening too, but oftentimes that's not the direction of the flows.

Speaker 1:

So I think the best executive directors and CEOs are bringing to the table with their boards hey, look, these are some emerging trends, either macro level trends or industry specific things that we've got to pay attention to. And sometimes the board has awareness of these things and a lot of times they're like oh, that's interesting, I really didn't know too much about that. In the case of AI, I've personally done this a number of times for friends of ours where they've said hey, Amit, can you come talk to our board? And I've spent a lot of time doing that where I've said look, I'll give your board an executive overview of what AI is doing to the broader world and how it might impact your sector. That type of exercise, when you do that yourself or you have someone who's very deep in AI to come help you, is, I think, a good thing to do for boards. Where I think that association leaders get a little bit nervous about that is if their board is somewhat technical and technical of any flavor, so like doctors or engineers that have nothing to do with AI but they're, let's say, mechanical engineers, and or actually if they're in a field that's actually quite close to AI, the board tends to be kind of imposing and the staff tend to be pretty afraid of, like, talking to the board about this stuff.

Speaker 1:

What I find really funny is this is that some of the people who are deepest to, like the research center of a given field actually have the least practical know-how of how to use the technology. So, for example, when I talk to leading AI research companies and individuals, they're craving input on how to actually use the tools they've built. Like, people who build foundation models oftentimes don't know the use cases. People who are doing research on like the next generation of neural network architectures often don't know what CLOD 3.7 can do, the way you do, Mallory. It's kind of crazy actually, but it's. You know, none of us can be experts in everything, right? So that's the whole thing. Is we got to look at it as again, this collection of people? So I think, going back to your question, I think the real key point is, I believe it's the responsibility of the association staff leadership to educate the board on contemporary topics that the board must understand to govern the association, and AI is clearly one of them understand to govern the association and AI is clearly one of them.

Speaker 2:

The last question here I want to touch on with motivation, and I imagine this is an issue across many associations. But let's say your board is really motivated by tradition. They want to do what's worked, they want to keep things flowing, they want to keep the association going as it has in the past. What would you and me do with, like, if your board is really stuck in tradition but obviously AI is not traditional, how would you approach that?

Speaker 1:

I mean, I think that in some cases it's appropriate to put a little bit of fear in them in terms of the tradition being upended, whether it's the association helping with it or not. So let's say you're in the legal profession somewhere and your board is not interested in AI for whatever reason and they have that kind of mindset you just described. Well, if you go and show them the kind of disruption that's happening right now in legal services, in in-house law, all this stuff due to AI, it's something that can't be ignored. I think that's a field that probably I would doubt there's a board of directors of any bar association or other legal association out there that isn't thinking about this stuff because it's such a dramatic impact in that particular field. But you can find certain fields that haven't been as impacted, certain branches of medicine maybe that haven't been as affected operationally by AI. So I think you have to kind of go and meet them where they're at but then try to compel them with like, look, this isn't a generalized idea, this is how it's affecting us. You may not see it, but this is what it's going to do and make the case. And the other thing to remember is that, as a leader, your title actually is chief repetition officer. So, and that's for all jobs, at all levels. If you want to get something done, you're going to find yourself saying the same thing over and over and over again.

Speaker 1:

So do not think that going and you know, really advocating for AI with your board is a one and done thing. Maybe it's unlikely. It's probably a journey. You have to take them on the journey, starting with something that isn't even like an ask, where you're starting off with like an education session and you don't start with any assumptions. You bring in someone from the outside who knows this stuff and says, hey, I really want to introduce this person to you, to like give you an hour of this topic. That can be a great way to kind of make it a little bit softer. And then maybe the next board meeting you talk about hey, what did you guys think of that? Let's have a conversation about it.

Speaker 1:

What do you think the impact of some of these technologies will be right? So there's a number of different techniques I think you could use for that, but don't think of it as a one and done. It's going to be a continual process In some cases. You just have to be really persistent. So in some cases you just have to be really persistent. So after a while, if the executive director keeps asking for something, maybe the board gives in, maybe the executive director isn't looked upon as favorably. That's always a risk and I realize that's a real practical consideration for a lot of staff execs. But it's just a factor I think you have to consider is it's likely a many, many step process?

Speaker 2:

Chief repetition officer. I love that. It makes me think of an acting example in my own life where there's, you know, a couple acting books that I'll keep going back to over and over again and, even though I've read them multiple times, rereading it for the sixth or the seventh time I'll get one more thing out of it. Oh OK, I get this now. Now that I've had these life experiences, that makes a lot more sense.

Speaker 1:

So I love the idea of repeating over and over Totally, and that is why Mallory and I both wholeheartedly recommend that you listen to.

Speaker 2:

Sidecar Sync episodes more than once. Over and over all, 70 something 80 episodes that we have. Okay. So hopefully at this point in the episode you're feeling like you have reflected on your board's motivations. Maybe you're understanding where they're coming from in a little bit of a deeper way. So I want to talk about the next step, which is building that AI business use case.

Speaker 2:

When it comes to securing board approval for your AI initiatives, the quality of the business use case can make or break a proposal. The key is to build a case around organizational priorities and member needs rather than the AI itself. A compelling AI business case connects the dots between your association's strategic goals, current challenges and how AI can bridge that gap. Are your staff overwhelmed? Is your content not reaching the right members at the right time? These concrete problems provide the foundation for a proposal and then quantify the potential impact whenever possible, not just in cost savings, but in member value, improved service delivery and or competitive advantage. Effective business use cases also address implementation realities, including resource requirements, timeline considerations and potential risks. Boards, we can help you narrow down some options. So, amit, I want to hear your kind of thought process or framework for helping an association identify kind of the best pilot project. Ai use case to get the board on board.

Speaker 1:

Well, forgetting about boards and forgetting about titles and all that other stuff, just thinking about the individual. So I would take some time to study who these people are. So, of course, if you have a board of, like you know, 700 people or something, that's harder and actually that sounds like a joke. But there are some associations that literally have boards more than 100 people. I've seen that fairly often and it's quite common to have boards in the many dozens, like 30, 40, 50 people. That's a whole other conversation because fundamentally, boards that large are definitionally ineffective at making any kind of decisions. So that's a different problem, one that we won't tackle in the sidecar sink today. Maybe some point, but probably that's not really in our wheelhouse. It's more of like governance experts can talk about. How do you potentially get to a more streamlined board. There has been board reform and a lot of associations to get to seven person, nine person, 11 person boards that are still representative of a. Obviously the board chair people like that, but also other people who tend to be vocal at past board meetings. Even if you have 50 people, think about the four or five people who tend to talk the most and study their backgrounds. Think about what the roles are how long they've been practicing in that profession or that industry, and try to think about the types of problems that they encounter in their job. So you know, I think that's a really key thing to do in any type of interaction you have with someone is you want to relate to them, you want to do the translation. You don't go to them and say, hey, ai can translate video from English to Spanish. That's cool, but what we want to do is take it all the way to them and make it bite sized and super attractive to eat, which is to say that you make the content something that they understand. You don't say, hey, we have this generic translation capability, but rather, hey, you know how you have patients who don't speak English that well. They can kind of speak English, but they really would understand Spanish or French or something else better. Well, now AI can actually help with that, because this is incredibly great tool, and let me give you an example.

Speaker 1:

And then use a consumer grade tool. You don't necessarily try to do this at enterprise scale first, but you use a HeyGen or you use one of these other tools and you create a version. You take maybe even a video of that person, because a lot of times, board members have YouTube clips and other things about them and maybe get their permission for this because this might freak them out. But, like, put their video through hey Jen, at the beginning of a board meeting. At that, by the end of the board meeting or even in the middle of the board meeting, you'll have a translation and that hits home because it's actually them speaking with their permission, right at the beginning of the board meeting to do this.

Speaker 1:

So there's some things you can do like that to make it a little more personal, to make it actually matter. And so if I'm a doctor and I deal with a lot of patients who don't speak English and I have content that I can't really communicate as effectively and I don't speak Spanish, that'd be amazing, right, and so maybe that's not association business, right, but it's really relevant to the person. And they go oh, my God, I had no idea that AI could do this and do it this well. So you have to make people remember through the way they feel.

Speaker 1:

People don't remember what you said, people don't remember what they read. They remember how you made them feel. I think that's a Maya Angelou quote from something, this unbelievable thing and that's been stuck in my head for years, and it's really powerful because, that is true, like we're information overload all the time, but we do remember our feelings, particularly strong ones. Preferably, you know, we can help them get excited, but also it's appropriate at this time for them to have some degree of fear over what happens if you don't do anything.

Speaker 2:

Yeah, and there's this concept I think I talked about it on a previous pod, I don't know if it's out yet in psychology called a light bulb memory, where emotions are so strong that you kind of can remember an event with a lot of specificity. And I kind of have my own light bulb memory around generative AI, which was at Digital Now 2022 when Thomas showed us the GPT Playground and Dolly 2 at that time and I'll never forget it for my whole life because it was a strong emotional feeling. So thinking that you as an association leader could help your board have that light bulb moment with AI, that's really powerful.

Speaker 1:

I think it could be, and I think that part of it is you don't have to go all the way to the finish line of like, how would you solve the problem at scale, for your association across all of the different things you might want to do. And maybe you have like a grandiose vision for AI and you want to get the board sold on it and maybe it's not so grandiose, maybe it's just a couple of projects you'd like to kick off and you want the board's approval. But if you start with these little bits, I think you can go a long ways. And that's one of the coolest things. Like to your point, mallory. Ai is so vividly understandable when you demonstrate it and a lot of times people don't do that.

Speaker 1:

And this again goes to assumptions we all make about other humans. Is that, especially with highly highly educated people doctors, lawyers, engineers you know we tend to feel like, oh, we don't want to tell all these really smart like PhDs or doctors about how to do video translation or whatever. The use case is Right, something, something you think is cool, like, show them notebook LM? Well, of course they're going to know about that. There are PhDs. Of course they're going to know about that. They're PhDs. Of course they're going to know about this. They're doctors Well, probably not.

Speaker 1:

Actually right. There's a very good chance they don't know about what it is that you've discovered that you're excited about. So some little demo can be very helpful, and I wouldn't make assumptions about their level of knowledge just because of their overall intellect or education or how prestigious they are in terms of their roles and titles and all that stuff. So those are some things that I think can help break down a room like that. And again, you don't need the whole room, you just need the handful of influencers that really can drive the direction of the conversation.

Speaker 2:

So let's say you do your example, amit, where you do a video translation. The board is really impressed, and then their follow-up questions are so what are you proposing, right? What are you going to do with this? That's really neat. How does this apply to our organization? Do you think it's best to start with a smaller project, a quick win that may have less impact on the organization as a whole? Or would you say, kind of, shoot for the stars a bit, transform your association with AI so you can see bigger impact, or somewhere in between?

Speaker 1:

I think it's advisable to start small in almost every case, even if you have complete board buy-in. Let's say they have this collective light bulb moment and they're like we're all in, you can have all the reserves, just take them, just do whatever you want. And the board says just do whatever you want, mal, are you the executive director? We're handing over 100% of the reserves. Go spend them all in the next year. Right, that's not going to happen, but let's just say hypothetically that were to occur. If I were you, and as the executive director of this association, I would still recommend you start off really small, assuming you haven't done much yet. Start off with learning, which we always say over and over again ad nauseum, but it's really true, as the foundation is that if you're not educated even at a fundamental level, you shouldn't try to do like any type of experiments really, because you don't have enough of a basis to understand what to go experiment with. So start with some learning. The big thing there is get buy-in to train everyone. This is something we talk about a lot at Sidecar, that we believe it is this leadership imperative, perhaps even a moral one, that you really need to look at how to bring everyone along on this journey. And you know people say, oh, I'm just going to train the handful of people on my staff who are interested in AI. I don't want to mandate it. Or they'll say, oh, I have a technology team that are, you know, more forward thinking in terms of tech. Let's have them do the AI training, and perhaps the people who need it least. But also, I would suggest to you that you have no idea where the best ideas are going to come from. They might come from people you would never think to be included in that group, and there's ways of doing AI training across your whole staff. So, but I would. I would always start with that. Let's assume you've already done that or you're doing that. Then, yes, certainly a small experiment followed by a little bit bigger experiment. So it's, you know, crawl, walk, run, that kind of thing. I think that's important to see. You get some organizational, you know, stimuli that builds reps, that builds learning and all that stuff. So and we spent a lot of time in this pod talking about those types of topics I won't go into much more detail, but I think, even if you have total buy-in from the board, you want to have something lined up. That's pretty bite-sized that you can come back to the board with right away and say, hey, we're going to report back to you guys in the next 30 days on the success of this project. And, by the way, that's the only thing I'd say is set narrow timelines.

Speaker 1:

Boards of directors typically meet quarterly, sometimes less frequently. That doesn't mean that these people like go into hibernation in between board meetings If it's an important enough topic. What I would say to the board is listen, I'm not requesting a special board meeting, but I'd like to have an asynchronous update to the board. We're going to send that midstream in the next quarter with an update on this project so that you guys are aware of what we're doing. Of course, if you are making some kind of special request, you can ask for a special meeting.

Speaker 1:

If it's an important enough thing, you can actually ask the board to say listen, I want the board to authorize me as the executive director.

Speaker 1:

Or if you want to have more governance, you can say let's form a special subcommittee of the board with three people on it who will meet monthly with the executive director to talk through this, and that special committee actually has some capability right. They're not just, they're like pay attention to what the ED is saying, but they actually maybe have the ability to authorize more reserve spending or whatever. So there's a lot of ways that the board can get creative about this and be supportive. But the staff has to kind of put it out there and say this is what you need to do Because, also remember, you're a professional association leader, you know all about boards, you know all about your governance structure, your board of directors. They're typically not professional board members. They're professional doctors, lawyers, engineers, bankers, whatever. So you kind of have to guide them and tell them you can do this, like, as a board, you could do this or you could do this. So sometimes you have to put like a menu in front of them.

Speaker 2:

Hmm, I like the idea of a menu. So in the event that an association has kind of AI education checked off for all staff, maybe even their board members as well, and they're looking to start small, as you said, is kind of an essential first step for enterprise AI across your organization. But I don't know if I would call an AI data platform implementation like bite-size or quick. Do you think that's a good place to start or do you think even something smaller than that?

Speaker 1:

Assuming you've done some basic learning. I think an AI data platform is a good thing. To at least think about the concept of bringing all of your data from all of your different business applications, as well as your unstructured data, into a unified platform that you own and control is a strategically important concept in AI. Whether it's your first or 20th step in your roadmap really depends on a lot of factors like what else you have going on, how much technical skill do you have? What's your budget? So I don't generally refer to it as like the first step. In some cases it totally makes sense to make it like the first significant step, but it's definitely not like a little bitty project. It's an involved thing. It's not a year, but it's probably a couple months to get it set up, so it's a non-trivial effort. And the other thing is is it's kind of like doing plumbing. It's not going to like have a lot of sizzle initially, because you're putting this effort into building something that will then later be things. You build other stuff on top of which will then have the sizzle. So I think that's something to consider. You want to go you remember you're always selling right, so you want to go back to the board of wins quickly. You want to establish more credibility, grow that credibility. So I would start with things that are almost like consumer grade style AI use cases. So let's just say you don't even have right now everyone using Clod or ChatGPT. Well, get that done right, get everyone trained on it, do some real basic things, get some policies in place, get everyone trained and then go back and show the board the efficacy of that basic, low-level investment with just a consumer-grade tool.

Speaker 1:

And then maybe the next step is oh, there's some application If we put in place, let's say, some kind of AI around abstract submission. Let's say that's a pain point. Now, perhaps your board this is often the case are active content contributors because they're some of the deepest experts in the field right, they're at the pinnacle of your profession. So probably they're people who've contributed to your journal or they've spoken at your events and therefore they probably have had the personal pain of having dealt with both sides of that process where they have submitted a paper or submitted something for a conference and they've had to wait and wait and wait. And perhaps they've been on the approval committee side of it where they've had to review countless submissions, most of which are totally not on track for what your rubric suggests you're looking for.

Speaker 1:

So what if we can solve that pain point on both sides? What if AI can help us make that process much, much smoother? That's actually a fairly easy use case for AI. If you have an AI data platform or other tools where you can kind of take this unstructured data, put it through a process and do even like an initial ranking, that can help. So I think there are ways of taking smaller and then bigger steps for sure. But again, you know you started this part conversation by saying think about the pain points people have, and I would suggest that that's exactly what people need to be thinking about with their board, but at the individual level, think about what their personal pain points have been with your organization, because that's what they're going to remember.

Speaker 2:

So hopefully now you've got maybe a couple use cases in mind, maybe smaller pilot projects, as Amit mentioned, or maybe something a little bit bigger like an AI data platform, depending on where your association is. I want to wrap up this episode talking about that pathway to approval with the board. So you've got to look at your association's unique approval process. As Amit said, some boards meet quarterly, others monthly, some rely heavily on committee recommendations, while others handle most discussions as a full board. As a side note, amit, I did not know there were boards with like hundreds of people, so that's shocking to me, but I'm sure all of our listeners we've got a wide, diverse array of boards.

Speaker 1:

They're nodding their heads right now because it's a thing. It's a thing that's crazy.

Speaker 2:

Understanding the structure helps you plan your approach, so the key is to work backwards from decision points, identifying when your proposals need to be submitted, which committees need to review them first and how much lead time is typically required. When preparing your case, gather practical info that addresses the board's priorities. So, as we said, clear budget requirements, both initial and ongoing implementation timelines, necessary resources, security considerations and expected outcomes. Focus on translating technical capabilities into concrete benefits and, whenever possible, include examples from similar organizations, if you can. Your presentation approach also matters significantly. Balance visionary possibilities with practical implementation details. Be prepared to discuss both opportunities and challenges honestly.

Speaker 2:

Building support through targeted conversations before formal meetings can make a critical difference. Identify potential champions and skeptics and engage them individually to understand their perspectives. These conversations help you refine your proposal while creating advocates who can speak to its merits during board discussions. Amit, I want to zone in on one piece here where ideally you could, if you're presenting to your board, reference another association who's done something similar and what that impact has been. But, as we both know, while a lot of associations are moving on this, we don't have a ton of use cases or studies to look at right now. So how do you recommend approaching maybe ROI from that angle if we've just never seen this done before or even just kind of a more like qualitative impact.

Speaker 1:

So if it's a truly novel use case that doesn't have any kind of peer examples in the association market and to your point, by the way, I think we are starting to see more and more and more success stories with AI in the association community, which is incredibly exciting. But if let's just say you're pursuing some path that doesn't have a comp right where you can say, hey, this association did this or this similar organization did this and this is the result they got, you might want to think about it. Let's say it's aspirational. So if you rewind time, say five years, even fewer years, personalization technology was largely out of reach for most associations. So personalization AI was extremely complex, it was difficult to implement, it was very narrow in its applicability. So an AI recommendation or personalization tech was very specific to a given type of thing. Personalization tech was very specific to a given type of thing. And so back then, if you wanted to try to do these things, you would have to really point to hey, look at what Amazon does, look how effective they are at recommending products and how much cross-selling they're able to do, which is a significant portion of their revenue and an even bigger portion of their margin. And look at how great Netflix is at engaging audience by showing you shows that you might be interested in. Those are examples of AI-driven personalization, but up until fairly recently, those examples were largely like, out of reach for most associations. There wouldn't have been like association examples. I guess the point I would make is now personalization, of course, is a lot more capable and a lot more available, so it's possible to personalize anything all the time, which is super exciting. I love that. My point, though and there's tons of associations doing it, which is also cool but let's just say, you're doing something different. Like this.

Speaker 1:

Abstract submission stuff is a little bit more on the frontier. It's more about unstructured data and, let's say, there aren't a lot of associations, or any associations you can find, that are doing that. We'll find a comparable use case in a different industry. That's not about abstract submission, but maybe it's about some other unstructured data process where they are able to take a process from months or weeks down to days or hours, right, and then show like kind of the value creation there. A lot of times, automation actually favors only one side of the table, meaning, think about classical customer service technology. We've talked about this on the pod before Mallory, where, like you know, customer service tech up until now has been all about saving money. It hasn't been about making the customer's experience better, but now something like what I described with abstract submission can actually serve to both make the association more efficient, but also dramatically improve the quality of the experience for the customer essentially the person who's submitting. So I think that's a really important thing to be thinking about.

Speaker 1:

My bottom line on it, though, is that I think you're going to have to get creative. I think you have to really thoughtful about this. There's still not tons and tons of this. If we were at the point where you know every other association had great use cases, then you know you'd be kind of in the mainstream of adoption, and then people would perhaps even start ending up in the laggard category if they weren't doing this, and so you know we're not there yet, like. So if your association doesn't have a website in 2025, that's kind of you know you don't want to be there, right? So I think that's another thing to point to maybe is prior tech curves and not being behind again if the association has been in the past.

Speaker 1:

I do want to say one quick thing, just to double click on a point you made earlier. As we're wrapping all of this conversation about the idea of kind of this pathway to success with the board and getting people to approve. You said something about like again targeting the potential champions and the skeptics. I think this is again critical. It's similar to what I was saying earlier about the folks in the room thinking about them as individuals and, you know, garnering support. If you watch, like you know, political dramas, a lot of times you see people that are on the staff of the White House trying to figure out who in Congress is going to vote in favor of their bill, and it's kind of like that right in a way, maybe not as high stakes or as dramatic, but it's the kind of thing that you need to think about is how do we move the individual in order to move the group?

Speaker 2:

I want to talk a little bit about the actual board presentation. So I want to share an example with all of you that an association professional told me once so I don't forget it and they talked about using ChatGPT to practice for their board presentation and they assigned it different personas of people on the board and maybe like, provided their bio and said this person tends to be a skeptic about X, y, z and then had ChatGPT critique their presentation. So I think that's an excellent use case that you all can try pretty much ASAP if you want to. But, amit, you mentioned this AI executive briefing that you give. You often give this session it's about an hour long to association staff, leadership teams and to association boards, and I feel like you have really nailed down how to present this information in a way that's a little bit alarming but also exciting. But also people can walk away from understanding.

Speaker 2:

Okay, yeah, we got to start talking about this ASAP. So can you share some of your tips and tricks when you're thinking about presenting to association boards or any kind of new tech? That's kind of scary. How do you approach that?

Speaker 1:

I mean a lot of it is just contextualizing the moment in time we're in. So part of what I spend my time on probably the first eight or 10 minutes of that presentation you're referring to is talking about kind of economic cycles and prior periods of transformative general purpose technologies, like think about, like the printing press, or think about when electricity was first harnessed. Think about, like you know, the overall scale of what happened in the industrial revolution. I think about, you know, the digital revolution, what about the internet? Like what happened in each period of time in history when these general purpose technologies, you know, kind of diffused into society at large, and how long did it take? And what you see is two things Number one is that these technologies build on each other and, as a result of that, the period of time it takes to diffuse or fully penetrate, you know, the world at large is shorter and shorter and shorter, and so that's, you know, a radical decrease in time from, like, mainstream adoption of, let's say, the printing press, to when steam engines came out, to when the telephone was adopted, to, obviously, when computing, when mainstream telephones. You know, is all this compounds right Because they're able to work on top of each other, and then ultimately, obviously, with AI, we're seeing a faster rate of impact than anything we've ever experienced, because it's the compounding of everything we've ever done.

Speaker 1:

Of course, it's a different type of thing entirely too. So part of what I try to do is to frame the moment in time that we're in to say listen, you have to recognize that this is the beginning of another moment in time, similar to what we've in some cases. Some of us have lived through the Internet or you know, earlier days of digital computing revolution, and we've realized how transformative it was if you take a moment to reflect on it. So we want to take advantage of that perspective and so, if we level set that way initially, I tend to find that people from all walks of life take a moment, take a breath, they're like huh, yeah, I didn't really think of AI that way. I thought of it as this next whiz bang thing, but I never really thought deeply about it, right? So starting with something like that can be helpful, I think.

Speaker 1:

And then, from there, talking about like well, exactly what is AI? Let's demystify it, let's make it approachable, let's like not make it this nonsensical you know jargon soup that it tends to be but let's actually talk about what it actually does and apply it to like things we can do in our association. So the rest of it's pretty much just practical use cases of like this is the stuff you can go do and, like a lot of times people see like video translation demo. I have one of those of me. I did it like a year and four months ago with HeyGen and the technology has gotten way better. I still use it because the one I had was was really good and people like, oh my God, I can't believe that you translated yourself into six different languages and it took no time to do so. People, even if you have seen a demo over and over, it oftentimes doesn't mean anyone else has.

Speaker 1:

Or like a lot of times I talk to audiences all the time no-transcript Maybe you should do a like a stock recording of your executive briefing that we could share one day. You know, if our listeners would find that helpful, I'd be happy to do that and post that on our YouTube channel or somewhere else that would be easy to access.

Speaker 2:

Well, everybody, thank you for tuning into this episode. Hopefully you figured out a few strategies, tactics, to get your board on board with AI, and if you have had some success in this area, we would love to hear from you, maybe bring you on the podcast to interview you. So please let us know and we will see you all next week.

Speaker 1:

Thanks for tuning into 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 boot camps, 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.