Exploring the Role of Transformational Leadership and Small Bets in Tech with Jen Swanson

In this episode, host Dave Sobel discusses the topic of digital transformation and leadership with guest Jen Swanson, a seasoned professional with extensive experience in customer advocacy, marketing technology, and service channel operations. They delve into the importance of staying on top of your business and explore the concept of transformation in both the digital and leadership realms. Jen shares insights from her career and highlights the need for continuous adaptation and growth. Tune in to gain valuable insights on digital transformation and leadership.

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[00:00.000 --> 00:12.000] I dipped my toe back into digital transformation because I found somebody who had a similar perspective to mine and we've talked about the way to stay on top of your business. [00:12.000 --> 00:24.000] Jen Swanson, whose career spans over 25 years of roles in customer advocacy, marketing technology and service channel operations and higher education and healthcare organization, joins me. [00:24.000 --> 00:40.000] She's worked with organizations like the University of Minnesota, Capella University, Children's Minnesota and United Health Group. Her consultant career began in 2019 and in 2023 she expanded that work by creating Tuck Point Advisory Group. [00:40.000 --> 00:45.000] This is the Business of Tech. [00:45.000 --> 00:58.000] Today's episode is supported by Coreview. Your customers need your Microsoft 365 expertise and Coreview has the only M365 management platform designed for MSPs. [00:58.000 --> 01:06.000] Manage hundreds of tenants, automate manual tasks and monitor compliance, all while intelligently comparing to the baseline. [01:06.000 --> 01:20.000] With a no-code control approach, Coreview revolutionizes your Microsoft 365 administration. The powerful platform enables automatic reporting and remediation, ensuring optimal performance and security. [01:20.000 --> 01:29.000] The best part? You achieve this high level of service without the need for a large workforce, allowing you to focus on growing your business through efficiency. [01:29.000 --> 01:36.000] Want to know more? Visit coreview.com slash MSP radio and find out more. [01:36.000 --> 01:41.000] Well, Jen, thanks for joining me today. Yeah, it's nice to be here. Thanks so much, Dave. [01:41.000 --> 01:49.000] I always like sort of revisiting the idea of transformation, both digital and in leadership. And you spent a lot of time in here. [01:49.000 --> 01:59.000] I thought I'd actually start with helping me understand the idea of transformational leadership and how it sort of differs from transactional leadership. [01:59.000 --> 02:07.000] Sure. Well, I mean, I like to think of myself as having been in transformation my entire career, right? [02:07.000 --> 02:17.000] Which is, it would be a little long in the tooth if you ask me, but, you know, part of me thinks I'm still 23 and the other one starts to look at the years stacking up and I'm not super excited about that all the time. [02:17.000 --> 02:28.000] But I do what I think about transformation and especially what we've seen in the last, you know, 10, 20 years and think about that constant acceleration of technology and what it's done to business. [02:28.000 --> 02:40.000] I think that when we think about the people that are leading companies today and what got them to their point in their seat in whether it's the C suite or VP senior leadership. [02:40.000 --> 03:09.000] There is very little about what got them there today that's equipping them to deal with what's coming at them tomorrow, right? And so that idea of transformational leadership really is about sort of checking, I think, checking your skills, checking your capabilities, checking your tool belt and figuring out, okay, what if I got here that's going to equip me for this absolutely breakneck speed change that we are seeing in technology, in the workforce, you know, in what, you know, [03:09.000 --> 03:25.000] whether we are talking about hybrid working environments, whether we are talking about AI and everything, whether we are talking about trying to keep up with what technology is doing, you know, in operations, in sales, in, you know, every part of our business. [03:25.000 --> 03:44.000] I think leaders are really struggling to understand how to keep up. And I think that part of transformation leadership is about that idea of assessing sort of what's inside us to know what to keep and what maybe to let fall away so that we know how to move into what's next. [03:45.000 --> 03:55.000] You know, you've even said it in there. And oftentimes, I think digital transformation is kind of code for what you actually said, which is just keeping up with technology. Totally. [03:55.000 --> 04:11.000] Okay. And then in a way, like, we're just acknowledging companies that did a bad job of it by calling it something cool, like digital, oh, you'll digitally transform, which is easier to say as a consultant, then oh, you haven't been paying attention and you fell behind. [04:11.000 --> 04:25.000] So kind of screwed up for me. Am I wrong in thinking you're not this way? You're not right. So I have to laugh a little bit because when people ask me what I do, I always start with digital transformation. [04:25.000 --> 04:35.000] And I see what the reaction is. And there are some people whose eyes plays over because they're not working in the space at all. And they say, oh, that's nice. You have children. We go on. [04:36.000 --> 04:47.000] There's other people who lean in and say, oh, what part, you know, do you do software? And then that's when I say, actually, I don't do digital transformation. I do operating model transformation. [04:47.000 --> 04:55.000] People are like, what is that? I don't know what that is. And I say, well, I actually don't care what the technology is. Technology is totally irrelevant. [04:56.000 --> 05:12.000] What I care about is how organizations are evolving around technology, how leaders are evolving to sort of fully move in, move their organizations forward into competing in an experienced economy. [05:12.000 --> 05:24.000] How are they leading their teams differently? How are they transforming their organizations structurally, emotionally, spiritually, all of those other pieces, right? [05:24.000 --> 05:36.000] To be able to compete in this sort of totally new, totally, you know, completely rapidly changing environment. That's the stuff I care about. The technology piece is kind of, doesn't matter because it's going to change tomorrow anyways. [05:36.000 --> 05:48.000] That's the part that, you know, when you hear whatever stat you want to pull out of Harvard Business Review, whether it's, you know, 70%, 80%, 90% of companies are either in or done. [05:48.000 --> 05:54.000] That's my very favorite air quotes done with digital transformation, which you never are now, right? [05:54.000 --> 06:02.000] The ones that are getting stuck are the ones that think you can just like slap a technology on an old structure and don't worry about the rest of it. [06:02.000 --> 06:09.000] Those are the ones that are getting stuck because they're not paying attention to the leadership competencies. They're not paying attention to team structures. [06:09.000 --> 06:28.000] They're not paying attention to how you have to articulate strategy differently, right? Moving to outcomes, moving to thinking about things like, you know, not just saying, oh, we're an OK, our shop now, so everything's fine, but really understanding what that means about how you talk in outcomes, how you think about results and success. [06:28.000 --> 06:35.000] Totally differently than just saying, hey, let's go make some, let's go make more money this year than we did last year. That's not meaningful. [06:35.000 --> 06:42.000] How are we going to do it? Who are we serving? What do we want to do? What do we want to stand for? And what do we mean that we want to grow, right? [06:42.000 --> 06:49.000] Those are very different ways of leading today and technology becomes the enabler of it. It's not the way that we're showing up. [06:49.000 --> 07:00.000] I mean, again, to oversimplify a little bit, isn't this just a matter of like looking at your service offerings on a regular basis and realizing that you have to retire some because they have to launch. [07:00.000 --> 07:12.000] Yes. Yes. Oh, my God. Yes. But how many companies ever retire anything? I mean, so many companies I know when I go in, I say, when's the last time you sunset anything, right? [07:12.000 --> 07:21.000] You took anything off of your service offering or you retired a, you know, a tech stack or anything. And they'll say, what do you mean retire? Right? [07:21.000 --> 07:27.000] Like, that's just not what is in anybody's vernacular. It's only about adding and layering on. It's never about retiring. [07:27.000 --> 07:37.000] But how can you do that in perpetuity and still be able to serve your customer in any kind of way? It just gets, whoa, think about carrying all that baggage around, right? [07:37.000 --> 07:49.000] Like companies can't do that forever. And that I think that transformation piece, so that's where the leadership comes in is to say, I mean, you know, the old adage strategy is you have to say no to something. [07:49.000 --> 07:54.000] If you're going to be strategic, it's as much about what you're saying no to is what you're saying yes to, right? [07:55.000 --> 08:04.000] I mean, I'm glossing over some complexity there, obviously, and it's the innovator's dilemma, right? Is the ability of you hold on to these things because they generate you money. [08:04.000 --> 08:14.000] But my impression is, and I'd like your your take as somebody who spends more time on it, but it's easier to do when you do it more often because it's not so damaged. [08:14.000 --> 08:26.000] And it doesn't damage lines of revenue that if you're constantly sort of slicing at the back end of your offering, it makes it easier to walk away from older stuff and move customers to newer stuff. [08:26.000 --> 08:29.000] Am I right thinking about that way? What are the challenges? [08:29.000 --> 08:34.000] Well, you're totally right at thinking about that. And part of it is it's a muscle that like the whole organization to have. [08:34.000 --> 08:43.000] It's not just like, you know, a couple of tech guys in the dark room somewhere that have to be good at the whole organization, top to bottom, left to right has to be good at it. [08:43.000 --> 08:49.000] And especially the C-suite. We're just going to keep coming back to that first question you asked me about transformational leadership, right? [08:49.000 --> 08:55.000] Because it's very easy at the top of the house to get really comfortable with that recurring revenue that's out there, right? [08:55.000 --> 09:03.000] That monthly recurring revenue to the old systems that are getting older and older and older and harder and harder and harder to move away from. [09:03.000 --> 09:08.000] But it's about diversification of revenue streams, first of all, right? [09:08.000 --> 09:19.000] And it's also about, I mean, one of the core tenets of product management and of agile software development is small bets placed often, right? [09:19.000 --> 09:27.000] And so part of what you have to do is take these little bets of where can we perhaps diversify revenue streams? [09:27.000 --> 09:35.000] Where can we perhaps try some new experiences that, you know, I just love it when people will say, oh, we can't do that. [09:35.000 --> 09:40.000] We'll cannibalize our, you know, cannibalize ourselves or we'll cannibalize our revenue streams. [09:40.000 --> 09:43.000] And I just say, well, better us than somebody else. [09:43.000 --> 09:49.000] Don't you want to cannibalize your own revenue than to have somebody come in and disrupt you and take that money outside your company? [09:49.000 --> 10:00.000] Let's do it ourselves and retain that and not worry so much about whether or not we're, you know, taking money out of the right pocket, putting it in the left pocket because it still aren't money. [10:00.000 --> 10:04.000] And that's the part at the leadership level you have to get really comfortable with. [10:04.000 --> 10:08.000] So that the teams feel that freedom of innovation. [10:08.000 --> 10:15.000] Try things that give you the freedom to maybe not put all your eggs in one basket as the old adage goes, right? [10:15.000 --> 10:22.000] So what are the most successful businesses that you're working with doing that's a little different and unexpected? [10:22.000 --> 10:24.000] So I'll be honest with you right now. [10:24.000 --> 10:30.000] I'm working with a lot of really large companies who have really gotten entrenched to be super honest with you. [10:30.000 --> 10:32.000] They're really stuck. [10:32.000 --> 10:35.000] And you know what? My favorite companies to work with. [10:35.000 --> 10:42.000] I really like the companies and legacy industries, financial services, manufacturing. [10:42.000 --> 10:47.000] The companies that sort of are like the companies or the industries that Silicon Valley forgot, right? [10:47.000 --> 10:52.000] I live in the Midwest, but people have to call us flyover country. Fine. No problem. [10:52.000 --> 11:02.000] I love working with companies that are flyover company because there's this like hunger and desire to like try new things. [11:02.000 --> 11:05.000] There's this sense, I think there's a better way to do this, right? [11:05.000 --> 11:10.000] And there's this idea of being able to try again, small bats play stock. [11:10.000 --> 11:14.000] And we find a couple of teams that maybe we can try working differently with. [11:14.000 --> 11:21.000] Instead of working in these super rigid, you know, these are organizations that got really good at like Six Sigma. [11:21.000 --> 11:26.000] And, you know, really great operational excellence. There's no fat anywhere. [11:26.000 --> 11:32.000] They can just, you know, they can get it down to the, you know, a single paperclip of efficiency. [11:32.000 --> 11:40.000] But that doesn't leave a ton of room for opportunity and innovation and what if and how might we? [11:40.000 --> 11:47.000] And so I really love that these sort of old stodgy companies that you think are just like the dinosaurs walking around are going, [11:48.000 --> 11:55.000] Oh, let's go. Let's go try some new things. Let's maybe carve out a space and just see what happened. [11:55.000 --> 12:04.000] And I really am energized by the fact that even in these companies that sort of tend to be forgotten in our economy as maybe not being super sexy or super exciting, [12:04.000 --> 12:12.000] are really trying some new things and, you know, advancing a tech stack. [12:12.000 --> 12:17.000] You know, I know a lot of your audiences in managed services, they're bringing in things. They're trying things in DevOps. [12:17.000 --> 12:25.000] They're trying automation. They're really pushing sort of new APIs, new ways of bringing, you know, [12:25.000 --> 12:30.000] sort of the old server room that's in the back of some, you know, manufacturing facility, [12:30.000 --> 12:36.000] migrating to the cloud, looking at new data structures and like just seeing what would happen. [12:36.000 --> 12:42.000] What if, how might we again, you know, that kind of that design thinking and maybe not in the most, you know, [12:42.000 --> 12:48.000] they're not designing an app that's going to be displayed from a stage by somebody in a black turtleneck, [12:48.000 --> 12:55.000] but it's still really exciting for them. And that's the stuff that I get really excited about because they're really looking at how people [12:55.000 --> 13:01.000] and technology can come together to solve problems for the company. And that super exciting. [13:01.000 --> 13:10.000] Well, I'm with you because I think there's a direct correlation between how boring something sounds and how much opportunity there is to build businesses there. [13:10.000 --> 13:12.000] Yes. Oh my God. Yes. [13:12.000 --> 13:16.000] The more boring it sounds, the more likely there's a ton of opportunity. [13:16.000 --> 13:25.000] That's where the opportunity is, 100%. And I, yeah, I can geek out for a long time over like, you know, [13:25.000 --> 13:33.000] data structures or, you know, testing automation or whatever it is because I think that stuff gets really, you know, [13:33.000 --> 13:37.000] gets overlooked when you're not working on the hottest, you know, the hottest app. [13:37.000 --> 13:45.000] I'm sure that those people are going home for, you know, whatever holidays coming up and they're probably not looking forward to talking about their very mundane day, [13:45.000 --> 13:49.000] you know, next to whatever cousin is working on the West Coast on something exciting. [13:49.000 --> 13:58.000] But for me, that is the exciting stuff because it's those little wins that really pile up and I think make huge differences for companies [13:58.000 --> 14:08.000] because they're really moving, you know, moving the needle on some of these opportunities where historically I don't think they've gotten the attention. [14:08.000 --> 14:12.000] Well, I'm a good East Coaster. We like to just get stuff done. So that's why you'll just... [14:12.000 --> 14:14.000] Yes. We'll just bow in on it, right? [14:14.000 --> 14:24.000] Exactly. You've also worked with some managed services providers. Tell me where those relationships have worked really well and what skills they bring that you really value. [14:24.000 --> 14:38.000] Yeah. So when I am in with a client, oftentimes what will happen is I'm working with IT leadership to look for, you know, sort of, again, where can we try out some of these ideas? [14:38.000 --> 14:50.000] And I'll be honest with you, I tend to go in and piss off the business partners a lot. That's like my main job, to go in and ruffle feathers on the business side. [14:50.000 --> 15:01.000] But once we start to make some inroads on the business side of starting to think about not just throwing things over the wall to IT, right? [15:01.000 --> 15:09.000] Because that typically is when I come in, there's this sense of IT saying, like, we're not order takers, for God's sakes. We have strategic chops here. [15:09.000 --> 15:22.000] We have creative chops, but we be a partner. And as you start to create those inroads with the business where you start to see that we could partner on solution, partner on ideation, partner on innovation, [15:22.000 --> 15:36.000] inevitably there becomes awareness that there is skill sets missing on the engineering side, and they prop up really quickly, right? [15:36.000 --> 15:45.000] But it all of a sudden will realize we need to push into some new space because of a competitive issue, because of sometimes a compliance issue, whatever it is. [15:45.000 --> 15:59.000] And we don't have the skill set inside, and we've got to move fast. And that's where I really like having great relationships with management service providers and staff log teams where we can say, [15:59.000 --> 16:08.000] we need three engineers with this super obscure thing, and they can just go out and tomorrow we can have somebody on the team working on it. [16:08.000 --> 16:18.000] So those tend to be like band-aid approaches. And for other teams, there are times, and I mentioned DevOps before, and that has been one of the biggest opportunities for us, [16:18.000 --> 16:31.000] really looking for teams that can help to build out DevOps capabilities. The organizations I've been working with for probably the last 18 months, I think are largely immature in the DevOps capabilities, [16:31.000 --> 16:42.000] and they are the most reliant on external talent in DevOps, both to meet immediate needs, but also to help them develop the internal capabilities to meet DevOps opportunities. [16:42.000 --> 16:52.000] So it's kind of like a player-coach duality, right, that they're looking for. They're looking for teams to come in and actually just start to hit those backlogs and do what needs to be done, [16:52.000 --> 16:56.000] but also teach their internal teams so that they're not in there forever. [16:57.000 --> 17:06.000] So for me, I have a bunch of consultants that I work with all the time. I'm a small shop, work largely with 1099 consultants, [17:06.000 --> 17:16.000] but I also have a bunch of service providers that I work with that I know kind of where their sweet spot is, what they're really good at, who their bench is, [17:16.000 --> 17:23.000] that when I need to sort of send up that signal, who I call on for those things. And that, for me, is really helpful. [17:24.000 --> 17:31.000] Now, it works opposite, too. Sometimes these are partners that are in there, and they're fighting fires, and they'll say, [17:31.000 --> 17:37.000] Jen, could you go talk to the IT leader? Because I think they need your help, you know? [17:37.000 --> 17:49.000] And I'll try to go in and help them a little bit more on the strategic side. So it becomes this sort of, you know, a symbiotic relationship where we can kind of help each other sort of meet each other's business needs. [17:49.000 --> 17:52.000] And that's been really, really fruitful from over the last couple of years. [17:52.000 --> 17:56.000] Well, we've just identified the opportunity, so that's a perfect time for me to say. [17:56.000 --> 17:57.000] There we go! [17:57.000 --> 18:00.000] So if people are interested in learning more and getting in touch, what's the best way to do that? [18:00.000 --> 18:11.000] LinkedIn is really my main channel. So I'm at Gen, well, JG Swanson. So J for Gen, G as in George, not what it stands for. [18:11.000 --> 18:21.000] I come from a very German family, so G for German, Swanson. But Tuckpoint, Tuckpoint Advisory Group is on LinkedIn, and you can find me there as well. [18:21.000 --> 18:26.000] So give me a follow. I post a ton, but that is the best way, and you can also DM me there. [18:26.000 --> 18:30.000] And that's probably the quickest, also at tuckpoint.com. [18:30.000 --> 18:34.000] Jen, thanks for exploring this because we learned a lot and figured out exactly where to focus our attention. [18:34.000 --> 18:38.000] There you go. Awesome. Thanks so much, Dave. I really enjoyed it. [18:41.000 --> 18:47.000] The Business of Tech is written by me, Dave Sobel, under ethics guidelines posted at businessof.tech. [18:47.000 --> 18:51.000] This episode was edited and produced by Picture This Video. [18:51.000 --> 18:57.000] If you like the content, please make sure to hit that like button and follow and subscribe. [18:57.000 --> 19:01.000] It's the free and easy way to support the show and help us grow. [19:01.000 --> 19:13.000] You can also check out our Patreon, where you can join the Business of Tech community at patreon.com slash MSP radio or buy our Why Do We Care merch at businessof.tech. [19:13.000 --> 19:20.000] Finally, if you're interested in advertising on the show, visit MSPradio.com slash Engage. [19:20.000 --> 19:25.000] Thanks for listening today, and I will talk to you again on the next episode of the Business of Tech. [19:31.000 --> 19:35.000] Part of the MSP radio network. Transcription results written to '/home/forge/transcribe.sonicengage.com/releases/20240204155445' directory