Making AI Work (Without the Buzzwords): People, Process & Building a Team That Grows with You

0:00I'm Jamie Seeker and this is what it takes. Each episode I sit down with real business owners to talk about their journey. The wins, the challenges, everything in between. Let's dive in. Hello everyone, how are you doing today? I'm so excited to have our guest on. You know how everyone's talking about AI right now. LGBT automation, digital transformation, but very few people can actually show what making it work really looks like. And today's guest absolutely can. I'm sitting down with Greg Gillespie, the co-founder and principal at Collective. It's a data and AI consulting firm based in the Chicago area. He's been in the game since 2016 when he started his first data consulting company. In 2019, he co-founded Collective, which has since made the ink 5,000 lists three times. So what stood out to me is that Greg isn't only about flashy tools or trendy buzzwords.

1:02He's about helping mid-size and enterprise companies get their hands dirty and actually make AI and data work. It's not just in theory, but in everyday ops. So he's got a background in electrical engineering, years leading data programs and industrial and utility sectors. And he brings a really grounded system thinking approach to all of it. So we're going to talk AI, data, process management, and even get into how people actual humans fit into all of this. So if you're a business owner trying to scale smarter, build better systems or avoid expensive mistakes when it comes to data and tech, this episode is for you. So let's jump in. Hi, Greg. How are you doing today? Hey, Jamie. Doing all right. Thanks for having me on here. Yeah. What pushed you to start your first consulting business back in? What was it? 2016? Did I get all those stats right? Yeah. Yeah. It feels like it was just yesterday. Sometimes. Sometimes it feels like it was ages ago. But I got pushed into that because actually for a variety of things.

2:06So ever since I was like really little, my dad had me doing all types of entrepreneurial stuff. So mowing yard, you know, odds and ends, doing things for, you know, people. And I think that built some of my entrepreneurial spirit. And you know, as I went into the workforce, I always said like, I want to do some type of, I want to own my own business of some sort. Well, that led to an opportunity through a layoff that I was, I basically was laid off at the organization I was at. And I got exposed to Microsoft Power BI that year that I got laid off. And I was like, this is a great tool. I think there's some opportunity here. So instead of going to find another job somewhere else, I was like, you know what? I think this is my opportunity. I've been talking about this forever, which is kind of see what happens. And if it works, it works. If it doesn't, I'll go back to work for somebody else. And ended up working. There are a lot of ups and downs and rollercoaster rides. I found myself, you know, starting collective in 2019. And it's really been, it's really been a rollercoaster ride since then. But it's been great. Like you said, we've made that eight five thousand less three times.

3:08But it's been with a lot of hard work and, you know, great team members, great partners that have helped us get there along the way. Well, let's talk a little bit about that. First of all, good job, dad. I love that he exposed you to that. Because we were just having a conversation before we started recording this podcast about how most people get into entrepreneurship and their own businesses because they have a specific trade or like some skill set that they're good at. Or they see some problem in the market and that they want to go and solve. But you're like kind of the opposite. You very rarely do I talk to somebody who's like, oh, I've always, you know, kind of had that entrepreneurial itch, you know, in the back of my head. Like, that's really cool. So big ups to dad on that. But you mentioned building your team. And so let's talk people. What does it take to build a team that's comfortable with change, especially like AI and automation, everything's happening so fast when that kind of stuffs in the mix, you know, how do you build a team like that? Oh, it's well, I'll start off by saying I didn't know how to build a team right away when I first started my organization.

4:09I was, I was the individual that basically did everything, right? I kind of micromanaged and that just came from when you, I feel like that came from when you start your business, you have to do everything. You're wearing every hat and then everything's got to be perfect. And, you know, quite frankly, I'm a bit of a bit of a perfectionist. And that doesn't help things when you're trying to delegate. So we run a system called EOS and one of the things that they promote and there is all delegate and elevate. So in order for you to basically get yourself out of the business and start working on the business rather within it, you have to delegate tasks. And that was really hard for me. Luckily, I had a business partner that kept pushing me very hard to basically saying, you've got to get the stuff off your plate so you can focus on other things that help you grow the business and that starts with getting the right people around you, getting the right team and really investing in them. So they can do the things that they're great at and you can do the things that you're great at. So there's a lot of ways I could kind of dive into this.

5:12But what are your thoughts around something like this? Have you had experience around it? Well, yes. I mean, that is with Secret Solution, we work with small medium sized businesses and HR is one of our solutions. So that is absolutely what we've been doing the last 10 years in the company. But I really love hearing about your perspective on it and how you kind of faced it coming in. So what is your approach to the internal training upskilling stuff like that? Because that's something that stood out to me that you said is investing in them in their skill sets. That's not something that I think everyone lands on on their own. It's kind of like it's moving so fast and they just want to pick the right person that like fits into this puzzle piece. But to say, Hey, like, I'm going to mold this into, you know, something that could be usable, that's a different take. So I'm, I'm really interested in hearing about that. Like how did you help employees grow into, first of all, an AI literate,

6:13you know, contributing team member, right? But also just like fitting in your company culture and build a your own team. Like there's two different aspects there. Right. So at first, I'll kind of take us back to the beginning of collective of how we used to do it and how we're doing it now. And I think we're starting to do it the right way. But I'm sure, you know, if you talk to me in another six months, I'll, you know, kind of take this piece of people, crumble it up, throw in the trash and say, this is what we're doing now. But that's the life of entrepreneurial ship, I guess. So when we started collective, we thought we were going to be a running organization on all contractors. So we started basically, you know, all 1099s and the idea of collective was, is the way we came up with that name is we're going to collectively bring together all these 1099 contractors. And we're going to start doing all this work for all these clients out there. There's a great concept, but it was a pain to manage because with a lot, with some contractors, some are bought in and some are only worried about their hours are going to punch in the hours are going to punch out.

7:14And that's it. You can't get a whole lot of commitment. You can't get them to buy into company culture or anything like that. So we gradually started shifting to a W2 based with, you know, about 80% W2, 20% contractors, but that took us while to get there, right? And along the way, we just started hiring people like, Oh, this person knows how to do Microsoft Power BI. This person knows how to do, do they as your data stack? How do we just come on board and you're a part of the team? But then what we weren't really looking for was the right culture, the right people that, you know, that we went on the team that can't, that aren't just technical, but they fit well and they gel well as your organization. They actually have the core values that my business partner and I both have and see the entire organization needing to have in order to be successful. And we were starting to have a lot of problems. So even though we had W2s, we went from the, from the 1099 to the W2 route, we were starting to see, you know, like project slipping, you know, people showing up lay all these different things or like just what's going on here?

8:16How do we get this better adoption? And we, I was sitting, so I, I mentioned we implement EOS and we had put core values as a part of our organization a while back and, you know, back in 2021 and I remember I was in Chicago one day, I was walking along the like Michigan and I'm like, thinking about these core values and I'm like, it hit me like a light bulb. And I'm like, if these core values don't mean anything to me, you know, if they're just a bunch of words out there in the ether, then how in the heck am I going to get the organization to adhere to them? How am I going to basically create a great team that can, you know, work hard, have a growth mindset, you know, be an empathetic and proactive communicator and all these things that I think that is important to basically delivering a great project for a client or having a great organization to work out. I can't expect anybody else on the team to adhere to these things if I don't truly believe in them. So that basically boiled down to basically a long meeting where we all got together and we redid our core values.

9:17And then after we got these core values in place, we kind of started looking at everybody on the team and saying, does everybody kind of, you know, fit these core values? And you know, not everybody did. But that didn't mean we're going to go off and fire everybody and say, we're going to hire new people with core values. One, that's not, that's not who we are as an organization. But we did start changing how we operated. And eventually those individuals who did not adhere to those core values, they kind of just saw themselves out the door because it, you know, the culture kind of led them out the door, right? And then what we started doing after that was starting to hire based on, quote, not just technical competency, but the core value competency, right? And we started using tools like, if you put the tools like culture index, predictive index, things like that, we started using culture index. And what that allowed us to do is see, we'll do certain individuals fit within the types of roles that they're in because the last thing we want to do is hire somebody and, you know, put them in a role that they're not going to succeed.

10:20So they might be great, they might be a great technical person, but are they a great consultant who is also technical at the same time? Because you have to hit all these different levels. And the last thing we want to do is put somebody in a role that they're not going to be successful or at least not successful at collective based upon who we are, what we do and what our company is all about. So we started putting in these processes. We started making sure everybody was aware of like, these are your, this is what is expected of you. This is, you know, using these core values is not just a, you know, something that you plaster on your website, but actually it's tools. So anytime, you know, a client issue comes up for a personal issue comes up. We look at these things and say, well, where are we not doing correctly? Are we not having this growth mindset to where we're bringing solutions to the table? Are we not getting our time sheets in on time, which is kind of like a proactive communication thing? Are we not proactively talking with our clients, you know, making suggestions before they come to us with them? So there's, using these core values as a tool is kind of a way that we've helped

11:22us identify the right people and help them grow into the, the true consultant that they need to be here at collective. And I know I haven't got to your other question about like, well, how do you get these individuals in and then cultivate them and help them grow to the next level? No, this is great. The process, right? So once we get them in, you know, let's say we hire them in as a senior analytics consultant and they're doing a lot of Microsoft Power BI work, maybe some Microsoft fabric work. They are basically paired up with their manager and their manager's role is really helped them understand is here's where you're at today. Here's basically the path. Do you want to become a, you know, solution architect within, you know, your specific role within the data analytics space? Do you want to bring that up and get that into a data platform or you're doing more data engineering, transformation? Do you want to be a full blown solution architect? Where you're working with pre sales and your help and sales. So we help identify that and then we put training programs in place to where they can get to where they need to be and then start exposing them to certain projects.

12:25They're going to help them get there even quicker. So it's not just about training, but it's exposing in the things within the workforce, like with in projects within other areas within side of our business that helps them get there. So there's a little bit more to that, I think that I'm probably missing out on. But for the most part, that's how we try to get people in that one match who they're supposed to be like, or match who are looking for set them up for success right away and then put a plan in place to help them get to where they want to be as far as a professional individual. But also I think that is a fair statement who they're supposed to be or who they've been created to be like their natural giftings and skill sets. I think that that is definitely a part of it. So there's that need that you have in the company and matching that with, you know, the direction that they're going to. But I love that shift because we see that when I talk about working with businesses over the last, you know, decade or so, one very common theme that I think businesses typically do is they have a need in the company and they hire to fill that

13:27need, which is simple answer to us, you know, a problem, a simple solution. But what we do at Secret Solution, and that's was, you know, previous to all of that work leading up to it is that we've found that if we hire for culture and fit and shared values, that's the foundation. And we train for skill sets that is a much better hire. And it might not, it might not be best in the short run, like right away, you can't hit the ground running like, hey, I need an expert in, you know, whatever Microsoft program you guys were working on, right? It might take a little bit longer, but in the long run, it just, it paid off for a dividends in our, especially like early in my career, prior to working with the companies that we do now. But in operations, and when I started hiring for the people and the direction that they want to go within their career, their culture fit into how, how we work our team in evaluating fit as well, like looking at my current team.

14:30And how does this piece fit into this current team? Because this person might be a great fit for our company, but I've got a team right here, and I can't have, you know, two left hands, right? Like I need to have, you know, I need to have all, all the parts of the body. So I think that's a really good shift that you kind of grew into and, and something that I think was very important to touch on. But how important, one thing that is very clear is that you, you were able to grow your teams, right? You're growing your company. So how important was this HR strategy when it came to starting to scale your business? Yeah, it was extremely important. It still is because you don't realize how much time and effort and actually cost goes into hiring the wrong person. Right. Yeah. That's another big thing. So when you're scaling and you need to get people on quickly, a lot of times you, you mess a lot of these things. And we did that when we were scaling quickly, we hired a bunch of people. And sometimes they went the right fit. And then what you end up, what ends up happening is, is those people

15:31exit the business either on their own or through some other way of, you know, of leaving. And it just costs money. And if you would just spend a little bit more time up front putting these processes in place, you know, aligning your core values with your culture and hiring the right people right away, it saves you just a lot of heartache and stress at the end of the day. So, you know, I think we've got it right. We've got a pretty good process in place now. There are times that we have rapid fired, rapid fire hiring. We have to go through and we check corners. Those cut corners usually come back to buy this in the rear end, but I think we got it about 85% of the way there. And hopefully we can keep putting that up as we continue to grow. Well, that's good. How big is your team now? Yeah, we have about 30 people. And then we're growing an offshore team as well over and so on. So are you keeping to that like 80, 20 that you landed on from the earlier years? It goes in spurts, but I think it just really depends upon the time of the year.

16:33So in the consulting world, you have a lot of peaks and valleys. And it's really just to depend upon this how cyclical the business is. So, you know, usually one more on our peak and we have a lot of work come in. We'll hire some of our contractors that we know we can trust and we'll bring them in. And then when we go down in that valley, when it is cyclical, then we'll let them go. And then we'll keep our full team on board. Wow, that's a, that's a really great strategy. Well, before I let you go, we ask every guest this one question in your own words. This is business owners tell all. So talk a little bit about those struggles that you, you know, that you experience the long way. What does it take to sit in your seat, make these kind of decisions, build these kind of teams, you know, let, let our listeners know what, what your take is on that. Yeah, there's a couple of things. I think about this a lot, this question does come up a lot. And I think grit is kind of like the obvious answer, but I think commitment is there as well, like if you're going to do this, like you do it, you go all in or you don't do it

17:35at all, there's no point of just kind of, I mean, half-ass in it for lack of better terms. I remember when it was in 2018, and I was kind of seeing the trend of what was going on before we sort of collected, and I kind of had a sit down meeting with myself and I said, are you going to do this thing or not, Greg? Like if you're going to do this, you got to get outside of your comfort zone and you got a fully commit and give it everything you got to make this thing great. And I think that's what it did it for me. It's what allowed us to kind of get to where we're at today with collective, but you got to fully commit because if you don't do it, then there's someone else out there that's committing more than you are and they're going to surpass you, whether that's your competitor or whatnot. So that'd be my, I guess that'd be my two cents on what it takes to really be successful in this industry. I think that's a really good word. And I think to the commitment to it also sustains you when times get tough, because it's easy to kind of waver when you're experiencing really big obstacles and, hey, am I going to make it through this, but that commitment to, all right,

18:38well, we're just going to see it through like that's off the table of walking away. And I think that that definitely can help you through that. So that's the mindset of like, you know, even when you hit obstacles and roadblocks, because everybody in the industry, you know, some people call it ceilings, some people call it walls, you keep hitting your head up against it. And you got to have that grit and that commitment saying like, I'm going to figure this out. And then eventually you plow through that ceiling or you plow through that wall and you're like, huh, can't believe that was so hard, but that commitment helps you get there, I think. Yeah, I love it. Being all in, I always love hearing from leaders who aren't just building cool companies like yours, but also helping other companies grow smarter. I think your company collective, the work that you've done really shows that it's really powerful when you combine that kind of stuff. And I especially love the people first leadership. I think the fact that you've poured into your team and created the teams that the way that you have is also showing in, you know, the services that you provide and things like that. So if you want to learn more about

19:41collective or even get in touch with Greg, Greg, how do listeners find you guys? Yeah. So they can go to a variety of places. So the easiest place to find this is our website, which is gocollective.com without the end, the end. You can also connect with me on LinkedIn. So please connect with me on LinkedIn. We have a LinkedIn website or I mean, sorry, a LinkedIn page. You can follow collective on it. And then we have a YouTube channel that has a ton of content on it. So we're always pushing out content in our space, which is all around the Microsoft Data Stack, Microsoft Fabric, Power BI as well as Databricks. So that's what we're all about. And then if you are going to be at FabCon here at the end of March, you know, please see us there. We are going to have a booth. So if you're in the industry, if you're looking to see what Microsoft Fabrics all about, come and check us out. Oh, that's great. Thank you so much. I'm all posting that on our show notes as well. So Greg, thank you so much for being on our show. And thank you for listening to what it takes. Awesome. Thank you, Jim. Thanks, Jimmy.

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