May 13, 2026

People-First AI Strategy with Joe Messina

People-First AI Strategy with Joe Messina
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AI is everywhere — but are we actually using it well? In this episode, Cristina and Alex welcome back return guest Joe Messina, an enterprise technology leader with 20+ years of experience navigating complex transformations. Together, they unpack why so many organizations are rushing into AI adoption without asking the most important questions first: What problem are we actually solving? And are we making things better for our people, or just moving faster toward a cliff? Drawing sharp parallels to the cloud migration era and the dot-com boom, Joe and the team make the case that history is repeating itself — and that the real risk isn't AI itself, but the absence of strategy behind it.

The conversation goes deep on what authentic, courageous leadership looks like in the middle of an AI transformation — from setting up meaningful gates and guardrails, to listening to your people before rolling anything out, to measuring what actually matters instead of just tracking adoption. Joe offers a refreshingly grounded perspective: AI should be in service of humans, not the other way around. If you're a leader trying to figure out how to cut through the hype, bring your team along, and actually do this right, this episode is your roadmap.

Credits: Raechel Sherwood for Original Score Composition.

Links:
YouTube Channel: Uncover The Human

Linkedin: https://www.linkedin.com/company/wearesiamo

Instagram: https://www.instagram.com/wearesiamo/

Facebook: https://www.facebook.com/WeAreSiamo

Website: https://www.wearesiamo.com/

00:00 - Pro AI With A Plan

02:14 - Welcoming Back Joe Messina

04:16 - Avoiding The Cloud Migration Trap

10:26 - When AI Erodes Trust

13:55 - A People-First Rebuild Like IKEA

17:20 - Governance Security And Accountability

24:40 - Pumping The Brakes On Hype

36:15 - Turning Resistance Into Curiosity

43:38 - Authentic Leadership And Wrap-Up

44:51 - Where To Find Us

Joe Messina: We've got to be pro AI in the sense that we are pro, a new technology that can help us. Let's figure out exactly where it can help us and do it smartly.”

Alex Cullimore: Hello, Cristina.

Cristina Amigoni: Hello.

Alex Cullimore: We just had a return guest on the podcast, Joe Messina.

Cristina Amigoni: I know. It's return guest season.

Alex Cullimore: Return of the guest. Yeah, opposite vibe.

Cristina Amigoni: I know. I wonder who we should have next to return. I have to look at our list. Yes, it was always great to have Joe on.

Alex Cullimore: Yeah. Joe's a very thoughtful leader and technology leader. We got to talk about what's on everybody's mind these days, which is AI transformation. How do you bring people onboard? How do you do this right? How do you avoid making the mistakes of the past? We've seen enough technological revolution in –

Cristina Amigoni: And present and future.

Alex Cullimore: Yeah. We've seen so many technological little revolutions, and he has a lot of good comparisons to some of the cloud integrations, as well as the dotcom boom. There's times and there's differences and there's similarities, but there's a lot of similarities in how people are approaching it, unfortunately, in the mistakes that are being made.

Cristina Amigoni: Yes. It's like, somehow, history is repeating itself and not the good way.

Alex Cullimore: Yes. That was to say the phrase, those who don't learn from history are doomed to repeat it, but those who do learn are doomed to sit on the sidelines and watch everybody else repeat it.

Cristina Amigoni: We're watching, and we're with the heartburn and I told you so song.

Alex Cullimore: I’ll be honest, this popcorn’s feeling stale.

Cristina Amigoni: Every time there’s a new headline. Yes. Yeah. Great approach on how to do it right, how to do it in a successful way as a leader and as a company. Hopefully, we'll speed enough towards the cliff of the train on how it's not working, so that we can then pick up the pieces and do it the right way.

Alex Cullimore: We can all make the better decisions that we're going to have to make at some point. But yeah, we could have done it the first time. Anyway, that's a different soapbox. I won't get on that one. That's enough of the episode.

Cristina Amigoni: Yes. Yeah, look out for our new throw pillows, quotes on throw pillows in this coming at the end of the year.

Alex Cullimore: See, I'm going to throw pillows coming at you.

Cristina Amigoni: Or thrown at you, if you repeat the same mistakes.

Alex Cullimore: Yeah. They come at you fast, like a projectile.

Cristina Amigoni: Have fun.

Alex Cullimore: Enjoy.

[INTERVIEW]

Alex Cullimore: Welcome back to this episode of Uncover the Human. Today's a special day, because we have a return guest. Welcome back to the podcast, Joe Messina.

Joe Messina: Happy to be here. I've never been invited twice to go on vacation with anybody, let alone on a podcast. So, thank you.

Alex Cullimore: Same level of special.

Cristina Amigoni: Yes.

Alex Cullimore: As going to be.

Cristina Amigoni: Slightly wilder ride to be on the podcast.

Alex Cullimore: Less known destination.

Cristina Amigoni: I like how we matched glasses, for anybody watching on YouTube. Everybody got the memo. We wear the same type of glasses, same colors.

Alex Cullimore: Glasses, colors, and mugs. That's what we all decided on subconsciously.

Cristina Amigoni: Yes. It's the mugs. It's the mugs.

Alex Cullimore: Joe, for anybody who doesn't remember your first episode, can you give us a little background on who you are and how you found us?

Joe Messina: I'm an enterprise technology leader. I've been doing this for 20-plus years. Transformations in complex environments is usually where I end up. Step into the, if your IT environment’s legacy fragmented, you have an operating model that you don't like and you need IT to be integrated in a service-oriented function, stabilize it, check out the risk, and then modernize in a way that makes sense is where I've spent the last few gigs in my career in all kinds of shared services. Been involved in multiple acquisitions, which I found really interesting.

As part of one of the transformations recently, that's how I hooked up with you guys and have been invited to two podcasts out of that gig, which is more than anybody could ever expect. Thank you.

Cristina Amigoni: For good or bad?

Joe Messina: Yeah.

Alex Cullimore: We can definitely vouch for exactly that bio. We met you in the middle of that environment in a swirling enterprise change.

Joe Messina: Yeah. For this topic today, viewing technology as an institutional capability, not just a utility and developing people to deliver better, stronger, more scalable, resilient organizations, I think AI hits right in the center of the bullseye for that and is top of mind for just about everybody. Kudos to you guys for having this as a topic.

Cristina Amigoni: Yeah. I mean, we started almost a year ago talking about this with, I think Chuck was on a year ago talking about it and then again, a few weeks ago talking about it, and we're still talking about it. It's not going away.

Alex Cullimore: Turns out, things are changing all the time and things are accelerating.

Joe Messina: Yeah, and it's not going away. I get the feeling that we've seen this before. With cloud, we did the same thing and asked, how do we adopt this? Not, what problem are we solving, or how do we do something better? I think we're at risk of repeating the same mistake in some ways. Also, the stakes are higher, because the cloud migration, it was mostly around discomfort with change and upskilling and delivery of services happening differently. This has a lot more to do with fundamental business model and people at the core of your organization. I think as leaders, we need to think this through now.

Alex Cullimore: Yes. Ideally, they perhaps should have thought of it first. But here we are. We are now having jumped the gun, so now let's think about it.

Joe Messina: Sure.

Cristina Amigoni: Yes. Yeah.

Joe Messina: It's a great opportunity, though, for us to learn.

Cristina Amigoni: It is.

Joe Messina: Looking at our people and business outcomes, how do we enhance that with AI? Recap from you guys, you've been at this for a year, you've talked to multiple perspectives. What are you seeing out there and what are your insights and reactions?

Cristina Amigoni: I would say, it's the same theme and it could be that we gravitate towards the same guests, or the same – the guests that have the same narrative. Along the lines of what you said, it's really about not just, how do we adopt these new things, but how do we actually – I mean, that's ultimately the goal is how do we adopt this new tool, this new way of doing things? That's an afterthought. That's almost like a success measure. It’s like, we've adopted, we have not adopted. Figure out, unpack the problems. The beginning of the journey, it's like, what problem are we trying to solve and how does this new tool, new technology, new way of doing things help us get there?

A lot of the conversations that we've had is how, oh, it's happened and reversed and how way too often, the what are we trying to solve is completely missed, because there's this just rush to just use AI, use AI, use the technology, lay off 30,000 people. Just write them an example from recent history.

Alex Cullimore: Cough, Salesforce, cough.

Cristina Amigoni: Exactly.

Alex Cullimore: Oracle.

Cristina Amigoni: Oracle. It's because we need all that money to be invested in technology. There are so many holes in that logic. From the mental one is what problem are we trying to solve and how is this new way of doing things and new technology going to get us there faster, better, bigger, more of service, in cleaner ways, in more ethical ways, as opposed to just rush, get rid of the humans, same humans are going to buy your products, so you may not want to eliminate them from the economy, just saying. And success. Isn't it success, though?

Alex Cullimore: I think that there's so much fear out there of becoming the next Kodak, or Blockbuster, where this is the next digital wave. If we miss it, we're going to get washed out and washed under. There's this rush to grab and be a part of it. It's exactly those questions, yes, the ante, Cristina, that people didn't ask in the beginning. It just immediately jumps to like, oh, we can replace people now. Then a bunch of companies did. Then people got panicked that they weren't replacing people fast enough.

Meanwhile, the people all suddenly got the hint that like, “Oh, if we work on this and if we implement this, this is the fast track to the exit for us.” It's a moment of a lot of fear. I like that. The cloud migration is a great example and a great metaphor. We jumped into cloud and it was more a move of where things live, and you had to just move your technology into the cloud and how you interrupt with the cloud. But with AI, it's now like, how do you replace some of the people, rather than just some of your infrastructure? It's not moving a server from the closet to some data center, it's moving thoughts from your people to a bot.

There's this uncertainty of how they're doing that, and there's overconfidence in what it can deliver. If we were seeing a lot of people who jumped in, tried a lot of things, aren't necessarily getting returns, and adoption is the metric that they all tried for. That means very little when they haven't planned how it's supposed to even help them.

Joe Messina: Yeah. I would agree with everything that you said. The parallel with cloud, also, is when adoption is your measure and then it doesn't deliver what it's supposed to, then you're reversing your direction in a year and we saw some of that. We saw, like any technology tool, it should enhance the business outcome and the people, not erode them with job loss and increased cost, wasted money. If you anchor on that enhancing the business outcome in the people before you step into something, then you're not in the position of a lot of cloud migrations where there is all this activity, but no real intent on what you were supposed to deliver. More cost effective, is it more scalable? Was it more secure? If you don't do it right, or you don't do it thoughtfully, then that shift to the cloud doesn't deliver those things.

I think we're in danger of making the same mistakes in the sense that the cloud technology didn't necessarily fail. The movement without a strategy failed. I think that is the thing that we're observing now.

Alex Cullimore: I'm going to stitch that into a throw pillow. I think that's exactly what happened.

Cristina Amigoni: Wallpapers, billboards in Times Square.

Joe Messina: Yeah.

Cristina Amigoni: I mean, everywhere. Airplanes plastered.

Alex Cullimore: Skyride that one over the next bit.

Joe Messina: Yeah, there's a series of throw pillow insignias I can start to see.

Cristina Amigoni: Yes.

Joe Messina: Use the tool.

Cristina Amigoni: Maybe that's our next business.

Joe Messina: AI should be in the service.

Alex Cullimore: Don't forget the strategy within extras.

Cristina Amigoni: Yes.

Joe Messina: AI in the service of humans, not the other way around.

Cristina Amigoni: Yeah.

Joe Messina: Use the tool, or you end up looking like a tool.

Cristina Amigoni: Now that's it. That is everybody's Christmas gift right there. Throw pillows, throw blankets, sheets, capes.

Alex Cullimore: I'm going to put that as a stick on the back of my laptop.

Cristina Amigoni: Exactly.

Joe Messina: That's great. But not to minimize what a massive change it is, really. One of the things you have talked here on this podcast many times about is authenticity. I can't stop thinking about, going back to season three and listening to some of those, because we're seeing so much of that come into play right now. There's hackers using AI to hack into systems and the SOCs are defending our systems using AI. There's everybody who's applying for a job is tweaking their resume and cover letters with ChatGPT and there's some AI agent on the end with the talent and acquisition people weeding you out automatically. It's a game changer in so many ways.

I was just reading in the paper this morning that people over 50 are just dropping out of the job market and retiring, rather than go through the massive change in mindset that's necessary to adjust to this. I think that's a good part to dig in. How as leaders do we lean into this and use it effectively to make our business outcomes and our people better?

Cristina Amigoni: On the people part, it's my current, one of the many current soapboxes, but it's definitely growing into my biggest soapbox right now is that I'm not an economics major. I'm a philosophy major. I did get an MBA, so I was forced to take some finance and accounting and economic knowledge at some point. From a very basic point of view, it doesn't make any sense to eliminate the humans from the equation. It doesn't make any sense to see hundreds of thousands of people getting laid off. It doesn't make any sense to do all these things, where even in the job market, applying for jobs, where it's now bought versus bought. It's almost like you're in a sci-fi future movie and it's just robots fighting each other, when all of this, any company and any business and anything that we knew is ultimately for humans.

I mean, who else is it for? It's not going to be for the bots, so it's going to have to be for humans. But if the humans economically are now struggling with just disposable income, or just income to even survive, who's going to buy your services and your products? Why would you lay people off? Which then, can actually come help you to participate in the economy.

I saw this very short clip from an economist explaining how the economy is going to collapse at this rate, because of all these economic factors. Of course, it is. Again, I don't have to be an economic major to know that. Of course, it's going to collapse. Because nothing that you're doing as a company after you laid off 30,000 people is going to matter if people can actually buy it.

Alex Cullimore: Yeah, I agree. That's the outcome. I think it goes back to what you were talking about, Joe, of say, having the people as part of the strategy, after understanding what this is going to do for your business and for the people, because why are you doing it otherwise? I mean, if the business succeeds, but nobody can buy it, that doesn't succeed. You're just good. The business will eventually fall over. If the business succeeds and you have no people, you can run out of support. You can do things, like Salesforce has started to admit like, “Oh, we shouldn't have just laid off 4,000 people, because AI wasn't A, ready to do this, and it's hurt a lot of trust.” That's just outside of the company. I can only imagine what morale is like inside the company when 4,000 of your colleagues disappear.

All of those human factors of what's the morale going to be? How are people going to take this? What are you even trying to accomplish, I think, are the first things leaders have to ask. Because there are things that AI can absolutely help with. They can actually speed up lots of tasks. They can do plenty of things now and it's getting better at the tasks that it has been assigned. That doesn't just mean that you can replace people. I did actually see one great story recently. I think you shared it, Cristina of Ikea, who they figured out that they could create an AI that answered most of the customer support questions that would come through. They had, I don't know, some 4,000 people who were part of their customer support that no longer really needed to do the job, because a bot could very quickly get to the answers.

What they did is hey, we've always wanted to create this interior design aspect of Ikea and we have these 4,000 people who have intimate knowledge of an expansive catalog of Ikea offerings, so they just retooled them and created an entire interior design section. I mean, I think that's a perfect example of what AI implementations could look like, where you can figure out what it really can replace and then what can you do with the people who have so much intimate contextual knowledge of your business that can do something totally different now empowered by AI, rather than just replaced by AI and you have the same functions.

Joe Messina: Yeah, exactly. I mean, back to the cloud example, it's got to deliver what you were intending to deliver. One of the other anchors you can use as you think through this as a leader, I think is let computers do the stuff computers do really well, and humans do the stuff humans do really well. We need clarity on what those things are and the courage as a leader not to jump on the bandwagon and say, I implemented AI and adoption as my metric, but the courage to lead through that. Because we tend to, I think because of the way some of the bots are presented, we tend to think they're thinking and they have a personality and we're supplanting them as a human. Technically how they work, it's not the same as the human brain. 

They're “learning,” but they're learning from large language models, not the same way that you are. If in the same way that when you migrated things to the cloud without the skill set to manage it appropriately, just for cost, well, then you had not the skill set to implement it appropriately, so it wasn't secure. It didn't function in the same way as it did when it was in your data center, and there's massive sprawl if you don't have proper governance around it. It became more costly, and then people panic and we're trying to move parts of it back and understand how they could be in the cloud better.

I think in the same way, without governance, how do you fire a bot that “makes a bad decision”? What if they do something that's not in the best interest of your company? There's issues of accountability and governance and security that need to be thought through and built around a successful AI deployment. Then when that happens, sure, it may free people up to do other things your business needs that it needs people to do.

I find it really hard to believe any business, especially in IT doesn't have tons of things that they would love to throw more people at, especially anybody who has gone through M&A activity, because any merger, or acquisition leaves you with a lot of really intricate sweeping up that needs to be in a thoughtful way. That happens through people who understand the environment and can think through it strategically. That's a long comment on your part about eliminating the humans, Alex.

Alex Cullimore: I really appreciate what you said, not only about it does feel like the cloud. Make sure you have security. There's a huge security and compliance issue that we really haven't resolved at all. In AI, we're just using these things. They're public tools. There’s a lot of people adding company data to these pieces, like we don't know where that's going. We don't know how secure that is, or how much can be regurgitated. Also, I love what you said about the leaders need the courage. We've talked about, hey, you need to establish, what do you really want this AI to do? What can it actually accomplish? What is AI able to do? But then, that leadership courage to stand up and say like, great, so it's not just that I implemented this, and that's a huge portion. It'd be best if that comes from the top and that leadership courage isn't just leaders at the top saying, “Oh, I hear AI is big. I'm going to be the one who tells everybody they have to implement AI.”

You need the top level to be a little bit more courageous and say, “Let's go deeper and let's figure out what we can do with it.” I'm sorry to put this on the middle layers that already are squeezed in so many ways, but the middle layers have to have the courage to be like, “What are we really trying to accomplish here? Can you please help me understand the why?” That's not easy to do, especially in a lot of companies that have created pretty rigid hierarchies and reduced the ability to ask questions of what the goal is. But that does take a good amount of courage, and I think that's a great word for one of the huge parts that's needed during this AI transformation.

Joe Messina: Yeah, I agree. I think, like we said before, it's tempting for a leader to want to make a splash with this, but it takes authentic leadership and courage to implement something like we have in the security world. There's a security gate. The earlier it is in the process of development, the better off everybody is. It's not a wall. It's a gate. So, that what you release is secure in the best that it can be. In the same way, say you're in a leadership position that's driving AI strategy, a simple gate that asks questions like, does this meaningfully improve a business, or human outcome? Does it strengthen, or weaken a human connection that is foundational to our business? Flat out, are we removing friction and making things more efficient? Or are we just removing people in creating something that nobody's going to monitor in eight whole months? If you answer those questions honestly and then thoughtfully implement from there as your anchor as a leader, I think you will have much more success.

Alex Cullimore: I love those questions.

Cristina Amigoni: Yeah, those are great questions.

Alex Cullimore: I think there's so much just, let's reduce friction. But if you reduce friction on the road that goes off of a cliff, that's great. You're just going off a cliff faster. That's cool.

Cristina Amigoni: Yes. Or if you reduce friction so that all sorts of passengerless and driverless cars go around, but there are no people in them, then why do the cars exist?

Joe Messina: Yeah.

Alex Cullimore: Yeah. I like the comparison with the security one, too. I mean, the better the sooner you ask those questions. I think it's also something that leaders can take advantage of. Ask those questions and it's okay not to have those answers, but the next question is, how do we know if we're moving towards it? My hypothesis is this will be more efficient for these reasons and we can have people do this. How are you going to test both of those things are true? Are you actually getting that efficiency out of the AI? What are the other abilities and how are we showing that we are making progress towards that? I don't mean just metrics that you can show on a KPI, but really think through, hey, are we making meaningful progress towards what we have stated as our goal?

Joe Messina: Absolutely. Yeah. As a leader stepping into an environment, implementing any new tool to observe the current state and listen to people first. How's that from Father and Son, the Cat Stevens song, “From the moment I can talk, I was ordered to listen.” In the song, glamorizing making the mistake of he just wants to talk and do his own thing. But as a leader, as an authentic leader, we need to get in there and listen first. That is as some people in Siamo are very apt to say, an active thing. It's not a path, slow, something that necessarily has to make progress crawl. That kind of active listening gets you the information you need to progress in a way that makes the most sense.

Alex Cullimore: That's the kind of thing that can uncover an opportunity you didn't know was there, right? You ask your people like, hey, if we could replace some of these things, what are things that you would want to do? I mean, it's like having a hackathon. Unleash people's creativity on issues they experience right now and what they would do if they were given the time not to just do their day job, or given the autonomy to take on something, have some ownership. These are opportunities that you could have faster with AI if you're doing that correctly. If you do that active listening up to your people, what opportunities might you uncover that you've never even thought of and that nobody in the boardroom and nobody at the C-suite and nobody at the leadership level has considered yet, because they're not at the ground level feeling that exact pain.

Joe Messina: Yeah. We're on a podcast and we're talking about leaders that should listen and everyone's like, yeah, we know that, but it's such a simple thing. It is also so difficult to do in a very quickly changing high-pressure environment. That is why I think AI almost makes the need for authentic, solid, clear leadership more important and less important. Sure, I can probably use 80% or more of ChatGPT to help me with a RACI chart, or a business plan, or something like that. But that just frees us up to do the other things that are above that that leaders should be doing, as far as thinking strategically.

Cristina Amigoni: For sure. Yeah, in that race of what everybody else is doing this, we got to do it as fast, or we're going to turn into Kodak, or Blockbuster, or Blackberry, Nokia. Name one of the many. But it's that, what happens if you don't? What's the cost of not having the strategy? What's the cost of not thinking people first? What's the cost of not including the people? Because eventually, you will end up like Nokia, Blockbuster, Kodak and the rest of them just in reverse.

Alex Cullimore: Must be one good historical examples of running and winning that race. I mean, one of the first search agents was Ask Jeeves. Does anybody ask Jeeves anymore?

Joe Messina: Going back that far is not a bad analogy. Going back to dotcom boom or whatever, that was a time of excitement and people were being hired up so quickly, because that was a technology, that was almost as revolutionary for businesses. It was as disruptive and mind-boggling and changing the way that people were thinking, in the same way people were telling you that, “Hey, oh, hey, I won't last. Oh, that Internet thing is a flash in the pan.” It's the same thing and that it's not going away. But it was a technology that people were excited about. I think the reason was they did not feel devalued by it. They felt energized by the possibilities. We as leaders need to make sure that as we're implementing AI, it isn't something that devalues our people. It's something that they look at as a way that they can use to improve their business outcomes.

I think that psychological shift within an organization to cut out the fear and be clear about how we're going to implement this into organization that is secure and more productive and better for our people and better for our clients and better for our bottom line, that's where we need leaders with that vision and strategy.

Cristina Amigoni: It's another five throw pillows right there.

Alex Cullimore: Devalue your people.

Cristina Amigoni: Yes.

Alex Cullimore: One thing I'd love to get both your perspectives on, we talked about there's this feeling of this anxiety and this rush and we had to be like, we got to get there. How would you as leaders say, hey, let's pump the brakes on this? Or, how would you approach something that feels like and can give this external rush? At least to my perspective, it doesn't seem like that is actually paying any dividends to feel that rush. How do you help yourself and your people not get overwhelmed, or get overtaken by the hype?

Joe Messina: Confidence and clarity about what you're trying to do. As a leader coming out and saying, we got to be careful about this is probably not the right thing. We've got to be pro AI in the sense that we are pro a new technology that can help us. Let's figure out exactly where it can help us and do it smartly. Set up boundaries about how we're going to use it. Be very honest about the auxiliary implications, or ethical problems that might come up for your business. Small example that I was just seeing again in the paper today is you're starting to see ads from companies, like Aerie certifying that no human was modified with AI in the presentation of this ad. To me, that reveals on the part of the consumer, at least a thirst for authenticity in a world where you don't know what you can trust.

To see that a company is putting that out as a market differentiator tells me that as a company, we need to have a very broad view and be very clear about how this fits into our organization and our image and our final product, right? To answer your question, which I really didn't do.

Alex Cullimore: You did.

Cristina Amigoni: No, you did. Yes.

Joe Messina: First, in making people and outcomes better, we can lead the systems there, then we're absolutely pro AI.

Alex Cullimore: Big confidence and authenticity, absolutely.

Cristina Amigoni: Well, and I think from a human perspective, because again, all of this is done for humans, because without the humans, I don't know why.

Alex Cullimore: It's an increasingly big assumption, but okay.

Cristina Amigoni: Well, eventually, it's going to have to be done for humans, because without the humans, there's no point in any of this. It's all going to collapse. But it is interesting to see, I wonder when the tipping point of there's so much technology AI bought customer service replacement, even on the phone, that it's going to swing back to this primordial need for human connection. I just read yesterday, actually, that malls are coming back after crisis of malls through pandemic and even before because of online shopping. Now, I guess, Gen Z is like, “No, no. I actually want to try things on and buy them after I tried immediately as I see them. I don't want to have to wait in the mail and then go through all of that.” I wonder how something like that is happening.

How much of this having AI bots doing so much of replacing so much of the human connection is going to swing back to like, now I'm only going to deal with this company if I'm guaranteed to talk to a human. I'm going to start eliminating all the companies that don't even get me to a human interacting with me.

Joe Messina: Right. Smart companies, I think, are realizing that issue around you used the word authenticity for sure, but it's trust. You've got trust that you've built up, or consumer confidence in your clients, vendors, consumers, and the trust of your employees. If your implementation of any technology isn't eroding that, smart companies are realizing that they need to head it off and either change the way that they're implementing it, or back off in certain areas. Like I said, enhance a human connection, rather than – I recently encountered, I think it's called WISP. I can't remember the name of the company. But if you apply for a job there, you take a personality test. Then instead of them sending you an email, you get an email with a video attachment of a person, I mean, clearly manipulated by AI, but they're saying your name and telling you about your results. I'm like, someone's really try. It's a little creepy, but someone's really –

Cristina Amigoni: I was going to say, it’s a little creepy.

Joe Messina: AI to make a personal connection. I appreciated the effort. It felt a little weird, and it wasn't under the guise that it was – that they went and recorded one for everybody at all. We were trying to enhance a personal connection, instead of it being one of 50 emails you get. That kind of creative thinking, I think, is necessary. I got to give them kudos for that attempt anyway.

Alex Cullimore: Yeah, that makes me think about the uncanny valley, the idea that if there's things that are very similar to humans, but not quite, it's really off-footing to us. When the Polar Express was released and animation was getting much, much better, but it really wasn't quite human and we were all like that, doesn't feel right. It feels a little bit creepy.

Cristina Amigoni: I still can't watch that movie.

Alex Cullimore: Yeah. But that feels like, maybe where companies end up landing and if we want to make the progress, we're going to have to get through that valley, but there is going to be, I think, a lot of time where there's going to be those uncanny experiences like that, where it's clearly, like you don't know my name, you sent that too quickly. You didn't have time to produce a video to give me my results. But it is trying to be more personal and it's an understandable move. It makes me think about the need for human connection and the desire for the authenticity.

It's starting to come out in lots of different places. Like, the algorithm for LinkedIn is definitely trying to weed out AI content, because it got so easy for people just to have AI generate 30 posts, schedule them all for the month and suddenly, you're up to the races with just basically, AI slop over and over again. People would get tired and they didn't want to read it and then it started driving people away from the platform, and LinkedIn had to bake adjustments to the algorithm to be like, “No, no, no, no, no. We're going to find the way that humans are now actually going to try and find ways to see if this was actually made by a person and boost those results.” I mean, there's companies already seeing the, “Uh-oh. We're going to lose people if we lose people.”

Cristina Amigoni: Yes. Another throw pillow. It's a collection of throw – 

Alex Cullimore: That one's going to look so stupid with no context. We're going to lose people if we lose people.

Cristina Amigoni: It's like the saying, you can change the people around you, but you can't change the people around you.

Alex Cullimore: That one’s a good one. That one could work on a throw pillow.

Cristina Amigoni: If you had a magic wand, Joe, which you will have and you do have a magic wand as a leader, how would you implement and deploy AI? How would you help a team? How would you think people and problem first?

Joe Messina: Yeah. Just everything that we talked about here today. You start by listening, and that doesn't mean slowing things down, and then put up a gate and for those questions that we talk about. Is it enhancing business outcomes in people? Is it eroding trust? Be clear about what we're trying to accomplish. Then put up guardrails so that you can do it cost effectively and securely and meaningfully and sustainably, and then progress, and to your very initial point, measure the right things, not just adoption. Those things should do with things that matter to your business. It should be a measurable business and outcome that you're improving.

I think in the overall scheme of it, leaders who get that right are going to be the ones who are most impactful, and they're going to be the ones that we remember navigating AI successfully, and they're going to be the ones that people imitate, just like there were a few people who took the time to do cloud right. I think it's a great opportunity for us to get out there and do it right and really have a huge impact. I'm not scared about it, if we have the leadership that's authentic and courageous enough to do it correctly, to not make the same mistakes we did with other technologies, to learn from it. To me, it makes good leadership more important, rather than less important and it makes having good people who understand the technology and how to use it properly more important, rather than less important.

Alex Cullimore: Yeah, that obviously makes sense. I think that's one thing that we see over and over again is people not establishing the why upfront, which takes a lot of listening, because it's not just going away and putting yourself in a sweat lodge and then coming back with a beautiful vision for your company. It's figuring out what people really need, what people are able to deliver, what currently exists and what you believe should be the right move in the future, getting people onboard with that and then really, that measuring the right thing I think is one thing that ends up being missed so often, because we go to the things that are easy to get a metric on and they can be gathered without too much effort. You can make sure that people have logged into something, new tool, or make sure people have posted on some new tool, or have asked a question if it's in the terms of AI, or use AI for some task.

Those are easy to find out if somebody's doing, but this is nothing about whether that's helping anybody, or it says nothing about whether that's accomplishing the things. I think there really is a huge importance in figuring out what you're measuring and how to ask questions, even if it's a feeling around the leadership team of like, okay, on a scale of one to 10 now, how are we feeling on whether we're any more productive than we were before? See why people start to answer that and that gives you that chance to listen, that chance to dig in deeper. That feels like such a subjective measure. But if you can start to feel that pulse, now you know when people are actually adopting, adopting, not just using but adopting and actually feeling like they're making a change.

Make sure that it actually does feel like making a shifting efficiency. Of course, that requires trust that people are going to give, not just a positive answer, but a helpful answer. But it's something that to think about.

Joe Messina: Yeah. I think you're getting to the crux that as a leader looking at the company and not seeing a bunch of dumb people, but seeing people who are doing important jobs. I'll tell you, I swear leaders look at us like, sometimes we're a bunch of dumb people. There are people who understand the company, who understand the jobs they're doing and they know a leader who has a strategy that is authentic. If you're a leader who can clearly enunciate that to people, where they can understand it and get onboard, that's where you will have success. Because without that, people are smart enough to know if your new technology is just a new shiny toy, or a science experiment. Because without strategy that you have and then communicate to people, that's all it is, and it will never work the way that you think it is.

Alex Cullimore: It's like all the infomercial lines and just buy one, get one deals that became popular. These things might work one time, they might work as a one off, but eventually, we all just become numb to them and we're all very aware when we're being sold something. Now in this world to get pinged with ads so much, everything feels like it puts – I personally feel like everything, it puts me a little on edge of like, what is this trying to sell me? Where's the edge here? Where's the angle? We are so especially suspicious now that I think you're absolutely right. If you don't have that authenticity, if you can't seem genuine to people, which the only way to actually seem genuine is to be genuine, you can't just seem it, but people are really listening for that and really able to know, “Hey, this doesn't feel right. This doesn't feel genuine. What am I missing?” The second you feel like that, what am I missing? Now you're looking for it, instead of trying to be onboard with whatever is coming down the pipeline.

Joe Messina: Yeah. I think in our last podcast, we defined authenticity as not having to uneasily ask the question, am I being manipulated? We worked about then from a leader perspective. But that environment where you're dealing with AI, either with a vendor, as a consumer, or with your own company, you need to have that same level of comfort that this is a tool that we're using and I'm not being manipulated by it and it's not being used by people to manipulate, or eliminate me.

Cristina Amigoni: Yeah. I have a challenging – elite challenge, if we want to say that way. Elite alumni challenge. I don't know the answer, so this is not a trick question. But as a leader, how would you approach people on your team who are just really resistant to adopting, integrating, thinking through how do we use AI, and there's just so much resistance and fear, or resistance? You don't know whether it's fear now, but so much resistance that they’re definitely are in the realm of the same when the dotcom era was happening of like, “This is just a flash in the pan. I just have to wait it out and it'll go away.” But we know it's not going away. Most people know it's not going away. How do you get those people on board somehow, and to not spend so much energy putting up the wall when they could still contribute in a lot of ways and they still do, but they're almost held back by this need to fight against it?

Joe Messina: That's a complicated question. A simple answer is when people feel empowered, or excited about a technology and not devalued by it, like we said earlier, then they’re more apt to accept it. Depending on the employee. I've not to make fun of Unix admins, but they take an almost religious fervor to their systems. That may be in a side bar, like there's a different psychology maybe at work in certain situations, but I think there are different approaches you'll take the people depending on the function.

If the first thing you can do after you clearly, as a leadership team. Now, if you are a single leader with a strategy that makes sense and then senior leadership changes at every 12 or 18 months, you've got an environment where you can either insulate people from that, or as a leadership team, get on the same page. Once you have that strategy and can clearly enunciate it to people where they understand that their work life will be enhanced, and that may be starting with look at what we can do to make this horrible task that you do better. Tell me five other ways where this might apply to your job, where you can do those other things that you never have time to do. That's one tactic. Just manager to employee that I would like to see people take.

But generally, having a strategy that makes sense that is foundationally based on business outcomes and when an employee start to see the fruition of that and see the fruits of it, that speaks almost louder than just what the leader is saying, then that creases the trust that they have in the organization, the strategy, and the leader. I think those were the people we are talking about who are going to be successful at this.

Alex Cullimore: That's a great answer. I think that's a good virtuous cycle to be a part of. I think that is, and really, you've established that genuine why that this is going to help. This isn't going to be devaluing of people. That's definitely the first step. Like, our intention is this and this is how we're going to do it. If you're not genuine about it, people will see through that. But if you're genuinely there and people have something they can get behind, it's a great start. I think beyond that, there's going to be individual reasons that people are resisting and getting really curious about, hey, what's driving this? What are you particularly worried about? What's the worst-case scenario that you think is going to happen?

Then you get to address it on a more personal level and maybe it's, I'm going to get replaced. Okay. Well, what are the – It's exactly back to what you said, Joe. Hey, what are five things that this could improve if we can get this one irritatingly tedious task off of you? Also, figuring out that there are other ways to do things. We talk a lot about working genius on this podcast. I do a lot of the WI, because that's where I live in my geniuses, or the initial generation phase. I didn't love that AI was generally generating things. At first, I was like, okay, well, I like the putting things together portion coming from a blank page. On the flip side, Cristina does not like that. She s to have something that's generated and be able to go and edit through it.

What I found out was that I could generate things and then use AI to evaluate them/ I could have an AI bot come back and sharpen up a bunch of writing, or a bunch of ideas and come up with, “Hey, here are some angles you might want to think about, or here's then.” Suddenly, I was being boosted, because I was using it in a different way. It was on my end a misunderstanding of oh, this is only generation. Then when I realized, oh, I can I can use this to take off some of the things that I don't like doing. It's not just a generative thing, it can do some other things that would help me just improve my own work. Suddenly, I could use that in a different way. Finding out how it plugs into people's frustrations might be a great place to start, too.

Joe Messina: Yeah, I agree. Looking at it as joint learners is a great approach that puts you shoulder to shoulder with people, instead of any strategy that's an imposition against people's will. I think that's change management 101. This is change management on steroids. Because you're walking organization with a technology that's this groundbreaking and life-changing in many ways. No organization is just sitting there completely static waiting for it. It's always, we're buying this company and AI's here, or AI's here and we're buying a company and I move into it and 15 other things.

Cristina Amigoni: And you're in the department and you have a new leader and you have new people to work with. Yes.

Alex Cullimore: No, wait. We just shuffled again. Now, you have a new-new person.

Cristina Amigoni: But it's just one transformation. Why is it so hard?

Alex Cullimore: Change happens all the time.

Joe Messina: Leadership is more important. A lot less important in those situations.

Cristina Amigoni: Absolutely. Yes. I love the reality of changing organizations today, and the assumption that it's just it's just one transformation. It's just one change. What's the big deal? Let's just go. But like you said, it's 15 things stacked on each other all at the same time, and then again next month.

Alex Cullimore: That's one of my favorite examples it's explicit of leaders doing exactly what you said, Joe, and just looking at their people like it's a bunch of dumb people. Like, what? Change happens all the time guys. Come on. Okay, but do you understand what's happening?

Cristina Amigoni: I remember when we – well, I guess, it wasn't that reason. It was maybe a year ago, when there was another one of those just, it's just one change. Let's figure out the communication and the training, or whatever the change management plan is. Then when we list it out, I think it was 25 rows in Excel with another probably 10 columns of who's impacted, how they're impacted, what's the ripple of those impacts, what's the ripple of those impacts. I remember seeing the people staring at the screen and be like, oh, maybe we need more time for this and a different plan. I'm like, yes. It's not just one change. Look at this. And this is just the first layer of analysis of the impact on people. That's not even the second layer.

Joe Messina: Yeah.

Alex Cullimore: It's a wild world out there, and there's so much change. I think you're right. AI, it's just one of many things going on, and it feels like the biggest one, because it's currently one of the bigger black boxes, but it is one of just a wave of change that people are experiencing.

Joe Messina: But the opportunity is huge and. That's why it's fun, because to do this, right, the impact on the business and the people for good should be energizing for any leader who really wants to tackle it and fun.

Alex Cullimore: That's a great reminder that there is an opportunity, and that it doesn't have to be scary can actually be really fun, because there's something novel that we can do. We can change some things. It's not always a bad thing. It doesn't have to be changed on to you. You can do some change.

Cristina Amigoni: Joe, you did a great job at bringing your definition of authenticity from our first podcast, which is, can you – I think I'm going to butcher it. But can you ask questions without wondering how you're being manipulated? What's your definition of authenticity today?

Joe Messina: I think in context of AI in our discussion today, it's being yourself as a leader that people can see and trust and understand. Even if it's not agree with, it's trust and understand and for lack of a better word, to follow to success. As you prove that over time with results in dedication to business outcomes and people that's flexing that courage in the clarity of communicating your strategy, that makes you an authentic leader.

Alex Cullimore: Right then.

Cristina Amigoni: Where can people find you?

Joe Messina: Find me on LinkedIn. You can find me over email. You can find me running around the park.

Cristina Amigoni: You can find out the throw pillows in your local stores by Christmas.

Alex Cullimore: This is a Home Goods special now. Well, thank you so much for rejoining us, Joe. It's great to have you on all the time and always good to get to catch up and talk to you.

Joe Messina: I surely do appreciate it sincerely. Thank you both. It's always a pleasure to be here.

Cristina Amigoni: Yeah. Thank you.

[END OF INTERVIEW]

Alex Cullimore: Thanks so much for listening to Uncover the Human. We Are Siamo, that is the company that sponsors and created this podcast. If you’d like to reach out to us further, reach out with any questions, or to be on the podcast, please reach out to podcast@wearesiamo.com. Or you can find us on Instagram. Our handle is @wearesiamo, S-I-A-M-O. Or you can go to wearesiamo.com and check us out there. Or, I suppose, Cristina, you and I have LinkedIn as well. People could find us anywhere else.

Cristina Amigoni: Yes, we do have LinkedIn. Yes. Yeah. We’d like to thank Abbay Robinson for producing our podcast and making sure that they actually reach all of you. And Rachel Sherwood for the wonderful score.

Alex Cullimore: Thank you guys so much for listening. Tune in next time.

Cristina Amigoni: Thank you.

[END]

Joe Messina Profile Photo

Technology & Transformation Leader | Coach | Teacher

Joe Messina is a technology and transformation executive, coach, and people-first leadership advocate with more than 20 years of experience leading complex IT organizations and enterprise change initiatives. He specializes in aligning technology strategy with business outcomes, with deep expertise in M&A integration, cybersecurity, IT operations, and large-scale organizational transformation.

Throughout his career, Joe has led cross-functional teams and advised senior executives on navigating complexity, driving operational effectiveness, and modernizing technology functions to support growth and resilience. His work increasingly focuses on the role of AI in the modern enterprise—championing a pragmatic, human-centered approach that enhances workforce capability and delivers meaningful business value.

Known for his authentic, grounded leadership style, Joe combines strategic insight with practical execution, helping leaders and teams build trust, clarity, and momentum during times of change. In addition to his executive and coaching work, he is actively engaged in his community as a youth athletics coach and a volunteer teacher for adult learners, reflecting his commitment to developing people both inside and outside the workplace.