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45: Driving Digital Transformation with People and Processes with Digital Consultant Jen Swanson

Published September 15, 2020
Run time: 00:58:21
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Every company thinks they’re a special snowflake, and when it comes to digital transformation, they actually are. Jen Swanson is a digital consultant who guides companies in their digital transformation journey with her philosophy of placing small bets often. In this episode, Jen breaks down how digital transformation is not just a technology integration, but a people and process integration, that ultimately delivers a more valuable customer and employee experience in every part of a business.

In this episode, you will learn:

  • Who really created the first version of LinkedIn (spoiler alert: it’s Jen).
  • Where products fit into digital transformation. When digital transformation is done.
  • How to use the iterative process of agile software development throughout your business.
  • What drives digital transformation.
  • How product management is a combination of art and science.
  • How digital transformations processes are alike and different between Fortune 500 and growth-stage organizations.
  • Why tech is just a tool, and people are where it’s at.
  • Where to begin with digital transformation and how it starts with checking your own assumptions at the door

This episode is brought to you by The Jed Mahonis Group, where we make sense of mobile app development with our non-technical approach to building custom mobile software solutions. Learn more at https://jmg.mn.

Recorded September 2, 2020 | Edited by Jordan Daoust | Produced by Jenny Karkowski

Show Notes:


Jen on LinkedIn


Episode Transcript:

Tim Bornholdt 0:00
Welcome to Constant Variables, a podcast where we take a non-technical look at all things technical. I'm Tim Bornholdt. Let's get nerdy.

Today we're chatting with Jen Swanson. Jen is a digital transformation and innovation consultant. She has a windy road of a career which she discusses in the podcast. And frankly, this entire episode is really fun and insightful. We mostly focus on how digital transformation is applied to organizations of all sizes. So if you're interested in digital transformation, you're in the right place. Let's just jump right in. Without further ado, here is my interview with Jen Swanson.

Jen, welcome to the show.

Jen Swanson 0:53
Thanks for having me, Tim. I really appreciate it.

Tim Bornholdt 0:56
I'm really excited to talk digital transformation today. But before we get going, I would love it if you could tell everybody here your origin story. How did you get into this crazy, wacky world of digital transformation?

Jen Swanson 1:09
Well, like many I came at it from a long and winding road. So I actually started my career in higher education. I have a master's in education. And I started working in traditional higher ed in dormitories and student activity offices and thought that I was going to kind of work my way through university administration. And that did not last mostly because I think what I figured out in my 20s and what I now know, you know, 20 years later, is the fact that I have career ADHD. I don't have a long span of attention on the things that I work on. I really like to go deep, fast, learn as much as I can, do some really interesting stuff, and then I like to move on and do something different. So I figured out pretty early on in my life that I am a builder and a creator. I don't run the business. I'm lousy at running the business actually and I'm much more at building and fixing things than I am at running things.

So after being in higher ed for a while and understanding that the pace of traditional higher ed was not for me, I moved on to nontraditional higher ed. I actually went to online education at Capella University. And there, really kind of expanded my horizons on what it meant to be a digital organization. You know, in traditional higher ed, I was always the youngest person in the room and I was always the person that they gave the technology projects to. In fact, my very first job, I walked in day one, and they handed me this binder, actually a set of binders that were like the big old D-ring binders that were like the eight inch D-ring binders. This was at the University of Minnesota. And they'd done a bunch of research on what at the time was called alumni portals. And they said, We want an alumni portal, but we don't want one off the shelf. At the time, there were like five or six companies that did sort of white label alumni portals. And this was before LinkedIn, so you've got to remember that. And they said, We don't want one off the shelf. We want to build one, you know, where like you can create a profile and share it with other people. So I built LinkedIn before there was LinkedIn at the University of Minnesota and if I had known that that's what we were building, I would have really taken a much different track with my career. But you know, it was these kind of projects where they were like, You're young, you're hip, you must know about technology. Come build us this thing.

And then it was, you know, a couple years laters, we think we want to start email marketing. Do you think maybe you might be able to figure that out? And my answer has always been, Yeah, sure. Totally. Let me figure it out. I'll go figure it out. I'll go dig deep. And so when I got to Capella, I was a unicorn at the University of Minnesota. At the time, not anymore, but at the time there were not a lot of people like me. I got to Capella and there were a ton of people like me, and it was super exciting, right? It was all these people trying to figure out how to do something totally different in education using digital tools, and I was in heaven and that was kind of my radioactive spider with my time at Capella. If you're going to ask about an origin story, I'm going deep on Marvel characters.

So I had kind of an unofficial rotation around Capella. I worked in marketing. I did event marketing. I did brand advocacy and referral marketing. Back in the day, we used to call it word of mouth marketing. I was a member of WOMA, the Word of Mouth Marketing Association. We did a lot of, you know, again at the this was, you know, in the mid 2000s, where we were really trying to ramp up what it meant to be not just a digital educator, educating in the digital space, but how did we really accelerate in terms of marketing and acquisition? And so I spent a lot of time in marketing. I spent time in operations. My time in operations, by the way, at the time, I didn't get why I was doing that. It was kind of a reorg. It was a tough time at Capella. There was a seat. I took it. I needed a paycheck. They offered me a job. I said, Yes, I'll do it. Now I look back at that operations time, and it was so useful for me to really understand sort of the back end of how an enterprise operates and the importance in systems in delivering a great customer experience.

So I've kind of been all over the place. After Capella, I went to Children's Hospitals and Clinics in Minnesota and I ran some digital marketing efforts there. And that was really where I discovered, or not discovered, probably more confirmed, that I'm much more of a platform person than I am a channel person. So digital marketing is fascinating, but not necessarily why I get up in the morning. I was much more interested in the content management systems we were using, and how are we designing workflows so that we were getting the most out of our very small staff and delivering content to get across multiple channels as efficiently as possible. And so that was really where I figured out that I was much better suited to the product side of digital than I was towards the marketing side of digital. And that really continued, has continued since then. That was kind of the nail in the coffin for me where I said, I'm not a marketer. I'm a product person. And I really went deep on that and then went to Optum and did some really cool stuff there working in a shared service organization within the Optum organization around common capabilities, common digital capabilities, and building out a product practice. And I did that for about three years.

And then I finally gave into a lifelong sort of question, which was, could I be my own boss, and it turns out, I can, and I started consulting about just over a year ago. And I've been having a great time helping companies figure out this product thing, this digital transformation thing, and how product fits into that and how it can really accelerate it. And it's been great fun and super interesting and is exactly where my interest lies and it kind of gives me a chance to give into that career ADHD, or that job ADHD, because I can take on new projects with clients to go deep, figure out the problems, help fix them, and then let the clients run with them. And I'm not around the business, as I said. So it really corresponds to my best skills and interests. And yeah, I've been having a great time.

It sounds like we're very much kindred spirits in that career ADHD regard because I looked at my LinkedIn a few days ago, and I noticed that working at The Jed Mahonis Group was the longest job I've ever had. I'm also only 32 right now, so it's early in my career, but growing up and being in my 20s, I jumped between different things because personally, I like to understand how things work. And I think you get kind of a similar kick out of that of like, Well, you know, maybe working in operations doesn't really fit anything directly that I have. But that's an interesting problem to learn. And like you said, you're able to take the skills that you acquired from previous jobs. And it seems like entrepreneurship is the perfect outlet for someone with career ADHD because then you can be like, Well, I guess today, I'm the janitor and tomorrow I'm doing sales and the next day I'm putting together a plan. It's very much every day is a new challenge and new skills that you can acquire to apply when people are asking you for your services.

Very much so and and yet at the same time, I will say that that is what kept me from going out on my own earlier was, Well, I've never written a business plan. I don't know how to do that. And at a certain point, I sort of stopped and said, Okay, that's a good excuse. But everything else in your career has been about learning something new. That's what you sit and talk about when somebody is interviewing you for a job is, you've not done this exact thing before, are you sure you can do it. And I talk about all of the times I've taken the skills and experiences I have, I've applied them to what comes next, and then I learn and I apply and I go on to then the next thing that I can then take this whole big body of knowledge and experience with and apply it to the next thing.

Tim Bornholdt 9:38
And I don't think that you not knowing how to write a business plan is that big of a deal, because I've never written a business plan. And I had the exact same thing. It's like, Well, I'm going to start a business. I need a business plan.

Jen Swanson 10:43
You must need one.

Tim Bornholdt 10:45
Yeah, right. It's something that's bestowed on high that you have to have a business plan and it's like, I've never done that. And I think it very much goes back to what you were saying where you don't know what you're doing, but you figure it out as you go along. And that's kind of like anyone that's building an app has to feel the exact same way. Because I know whenever we talk to new clients all the time, it's like, Hey, have you ever done anything with Salesforce? And your first thought in your head, you're like, what the hell is Salesforce? I've never heard of that before. But out loud, you're like, Well, I've never used Salesforce before.

Jen Swanson 11:22
But here's are all the other things I've done.

Tim Bornholdt 11:23
Right. And if you'd have asked anyone 10 years ago if they've done anything with Salesforce, you would have sounded like an alien. So I don't think it's unfair for you to say, especially when it comes to technology, to be on your heels or on your toes. I always forget what the expression is, but being able to adapt and go with the flow because technology changes and the whole environment changes so fast underneath you.

Jen Swanson 11:46
Right. That's right. And I actually took a cue from a friend of mine who's a career counsellor, and she said, Make a list of all the stuff you've never done before that you feel is holding you back from actually getting out there and doing this. And then at the top of it, write the following, Things I don't know how to do now but will know how to do in six months. And I just worked my way through it. I'd never written a proposal before. I'd read millions of proposals over the years because I was always on the client side. But I'd never written one. And I was like, Oh, God, how can I write one? What if that's a terrible proposal? It's like, Well, you're not going to know until you try. And so it was a really great way of saying these are the things, it was just sort of acknowledging, these are the things I've never done before, but I will in the next six months. And I just worked my way through those things. And now I have a whole new list of things, by the way, I don't know how to do but I will do. I will learn it in the next, you know, four weeks, six weeks, eight weeks, whatever it is.

Tim Bornholdt 12:52
That's amazing. I'm writing that down myself because I need to start doing that. Every six months things change and you have to learn something new anyway.

Jen Swanson 13:00

Tim Bornholdt 13:00
That's brilliant. Well, I think people probably want to hear us talk about digital transformation at some point here today.

Jen Swanson 13:07
That is why they came here, not about our synchronicities.

Tim Bornholdt 13:13
Well, too bad. This is my show and I'm going to talk about my idiosyncrasies. But let's start with the basics, bare bones. What exactly is digital transformation?

Jen Swanson 13:24
Well, that is the $10,000 question, isn't it? So for me, digital transformation is really simply about technology changing every single part of how a business conducts itself. So it's really easy for you to think digital transformation, we're going to get a really great website and we will be done with digital transformation. That is not digital transformation. Digital transformation is really about how do you look at your core strategy as a company, as a business, and think about what ways can technology help us do that work, deliver that value, in a more scalable manner, in a more efficient manner, in a more engaging manner, in a more valuable manner to our customer in a way that makes our employee experience better. Like literally looking at every part of the business, operations, finance, human resources, whether or not you've got remote workers, how remote working happens. All of that. Technology obviously has radically changed how we do business, right? And so when you talk about a company that is in digital transformation, the easiest place to look is, you know, sort of the squirrel, the shiny object that the customer is going to see, the fancy website, the chat feature on the website or a new e commerce tool or better data and analytics, or whatever. And those are a part of digital transformation. But it really is about the full transformation of the business, leveraging the technology that exists in the most efficient, scalable, engaging way possible.

And to our point a few moments ago, it is constantly changing. So, you know, I always sort of hang my head a little bit, shake my head a little bit, when I hear people saying, Well, when will it be over? I usually hear that from executive teams, from legacy executive teams, like, When are we going to be done with this transformation? And then I have to sit them down and hold their hand and say, I'm sorry to have to tell you this, but you're never going to be done. Because the pace of change of technology is never going to be done, right? The changing expectations of your customers are never going to be done. Just as soon as you think you are meeting and exceeding their expectations, a disruptor is going to come along and totally change how you have to deliver things or, you know, something like a pandemic, oddly enough, is going to come and say, Yeah, you thought you had this figured out, but you don't. And here's some ways that you're going to have to shift and pivot. And so that for me, it is all encompassing, and it's almost why I think the phrase of digital transformation is risking overuse and obsolescence. Right? Because in my mind, and maybe it's because I work in it, it is all encompassing, and it's here to stay. We're going to have to continue to transform.

Tim Bornholdt 16:52
Like you said, it's not a one and done thing, but it's not so much even we're going to start down the path and keep going. It seems like it's a lot more foundational and really hitting people right in their core. Because I would think, you know, a company that's old school that's been around for, you know, old school meaning like millions of years, like a century or something like that where it's like we build buildings, how is technology going to make this any different? I would imagine that you have a harder time convincing those people that the way that business is done in 2020 is way different than it was done in 2020 BC. And you need to evolve with the times. I'm trying to arrive at a question here. Is it hard to convince some businesses over others? Is it more of a generational thing that it's difficult for older generations versus younger generations? Talk a little bit about, like, what would be a hard sell in your case versus like an easy sell.

Jen Swanson 18:03
Yes, all of it is hard. And there's not an easy group. The fundamental way that I think about this is not necessarily in generational, although there is some of that at play. Certainly I think that legacy executives, which is a nice way of saying those who are maybe nearing retirement and ready to maybe transition to a younger generation, sometimes are the easiest to convince, because they see themselves being left behind by peers.

So let's use the masonry example. So masonry, the way that masonry is going to be laid is not necessarily going to be changing, but how their customers find them is going to and has already changed radically, right? So think about like, there was Angie's List, and now there's Yelp and there's hundreds of rating sites, and there's just the ratings that show up on Google in the feedback, like understanding how that's affecting their business is critical. How are they serving customers? Is it easy for people to pay their bills online? I know I've got some people who still want me to send in a check, including the lawn care company that just arrived in my front lawn. They want me to send a check. I don't have a way to pay them online. And while that's a little thing, you know, sometimes it can be a little thing that just becomes the reason why a customer doesn't renew the next year. And so what are the things that you're doing to remove friction for customers? Those customers want to make it easy for them to book the work, to pay for the work, to schedule the work, to give feedback on the work, and the internal employees need tools, digital tools, to be able to manage, you know what work is coming. What does the pipeline look like? How our crews scheduled? Are we maximizing efficiency of the scheduling of the crews so that we're not leaving this very expensive resource of our skilled labor idle when they are our product? And so in some ways, the the legacy executives or the legacy leaders of those kinds of, what I would consider, not traditionally digital businesses, see the value and understand that that's the way forward.

Sometimes you just have people who say, I'm going to leave it for my son or my daughter who's going to take over the business in two years to figure out. And that's fine. But you know, when you look at different kinds of businesses like financial services, or you look at education or you look at health care, there is sometimes nothing to do with the generation of the leadership and everything to do with persisting barriers to understanding how technology can change a business, and sort of people get stuck in the old way of thinking, you know. I'm a bank and people want to be able to come into my branch and do business with someone because they trust them. And this is their money that they're talking about. This is their savings, this is their home, and they need person to person interaction. They need personal bankers and all that other kind of stuff. Well, sure, and for some portion of your population, that's true. But then along comes a pandemic. And all of a sudden, that is just no longer an option. It's not something that is even if that's what's preferred, you now have huge swaths of the population who never have used online banking, don't understand online banking, maybe don't trust online banking, but are being forced to use it and have you really thought through what the online banking experience is. I have found that there are executives who of every age and every stripe, doesn't matter if they're young, up and coming, or on their way to golf course in Naples, Florida, there is sometimes a reticence and a belief that everybody feels the way I do about this product. They want to see their instructor's eyes, they want to see their banker's eyes, they want to see their doctor's eyes, and they don't think about the ways in which technology can underpin that and that's when you start to have companies that lag behind that are late adopters and late to the transformation game.

And honestly, that's my bread and butter. I work with companies that are like, you know, we haven't figured this out or we've done what we thought was enough, and now we're figuring out that that was only scratching the surface. And we are not equipped for really transforming, right? We did the bare minimum and now we know how much further we have to go and we don't have the right people, the right teams, the right ways of working internally to be able to really accelerate and drive this transformation. It's a little bit of an awakening to, Oh, this is a big deal. This is more than a website. This is more than a CRM. This is more than a little marketing automation. This is a fundamental change to how we work and we're not equipped to do it. And that's it. When they have that aha moment, that's magical for me as a consultant because I love going in those environments to say, Sorry that you're not there yet. We're going to help you get there.

Tim Bornholdt 24:09
Is a lot of your job then, would you say, is kind of teaching agile methodologies and teaching people just different ways of approaching problems? Or is it at least to start, do you kind of have to put out a fire here or there to prove that know what you're talking about? And then as you go, you kind of explain here's a better way, that you kind of teach your clients how you think, so that they start implementing that thought throughout their organization?

Jen Swanson 24:39
You know, it's really a combination. I joke about this a lot, actually, with clients is that I am a little bit of a therapist for leaders who have had some urgency of changing the internal ways of working. And I use that intentionally, that ways of working, because agile is one way of working. It is not the only way of working. And sometimes what happens is companies say, you know, We're going to do agile. And I love it when they say that because I know that that's going to be a problem. And I know that I will have a lot of work with that company, right? And I always say, Well, what do you mean when you say agile? Because agile is another term. Everybody wants to be more agile, but that does not necessarily mean you're using an agile methodology in technology, right? In your tech development? I always say, Are you using it in IT? Yep. Are you using it in the business? No. Okay, then I know where we're starting.

Because usually what happens is we've had IT organizations or technology organizations over the last 20 years start to shift from a predominantly waterfall into a predominantly agile environment. Not everything works in agile. You cannot put an ERP system in under an agile methodology. You've got to have a really strong project manager and a waterfall plan for an ERP implementation, right? Like it's just not going to happen in an agile manner. But where you start to see that predominance, you know, sort of where's the tipping point? And when IT shifts into the agile software development methodology, right? DevOps or scrum or scaled agile or whatever the sort of flavor is, it works great for a while, and then they start to bump into the fact that the business isn't operating that way, right? Finance isn't operating that way. And so part of what I do is come in and say, Okay, so there's different frameworks that we can pull together for your organization. And I personally am a big fan of the agile product framework, where it's a little bit of design thinking. Product management is a discipline. And it pairs well with agile software development, but it is not the same thing. And so how do you start to pull those pieces together where you engage in design thinking, you use things like design sprints, you've got product teams who really are in charge of these products, right?

And that's another big thing. Companies have a tough time with the word product. I wish, probably six times a day, that back when product development was developing, that there was a different term for it, because in many cases, companies that have products that are sold, physical products that are sold, actual tangible things, cans of soup on the shelf, keyboards, candles, you name it, physical entities. That's their product. And those companies have a dickens of a time trying to figure out how to apply the concept of product to software or to digital experience or platforms or capabilities, right? And so we work through language, sometimes to come up with new terminology. But we start to look at how that sort of small bets placed often, which is another phrase I use a lot with companies is, how do you take that iterative process of agile software development and pull it out of IT and into the business? And how do you need to staff teams that way? Well, what is the product manager's role in your organization? How much technology responsibility do they have versus how much business acumen do they need to have? How much do they need to be in a particular line of business versus really knowing a product that supports the business? That's different in every single company.

And so there are times where I get asked by clients to say, Well, can't you just give us some templates? And we'll just run with it? And I say, No, because the templates are useless until you start to figure out how they're going to work inside your context. And so that's really how I tend to work with companies is going in and it's a little bit therapist, it's a little bit investigative, right? I was actually a journalism minor in college so I bring that part out of conducting really good interviews with people about what's hard about your job, what are you frustrated with, what's really working, who's doing it right. And then start to come back and show leadership to say, Here's where your holes are and what you need. You need a common set of artifacts that your product teams are using, so that everyone's talking the same language. Your executive team needs to understand what product looks like. They need to ask different questions, right? They can't ask about when's it going to be done? They have to start shifting to say, How is this supporting the business strategy this quarter? What are you releasing now? What's coming next? What comes after that? And those are all mindset shifts. So it's a little bit of organizational development. Sometimes it's about restructuring teams. It's about, you know, trying to root out what the good meetings are from the bad meetings, so that people can do their work. It's all of those things together.

So I often say that I'm technology agnostic. So the product teams I work with run the gamut from operations teams with IVRs and customer service platforms, data and analytics teams with working with data lakes and big data and tableau. I don't know anything about those things. But what I do know is how teams can coalesce around them to be more effective using some of these methodologies. And that's really what drives transformation is that teams working differently, with sometimes existing tools and sometimes new tools or existing tools that are connected in new ways. And thinking about how that sort of evolves over time so that teams can do more with them. Executives want to know, Am I getting enough juice from the squeeze on this investment of these platforms, you know, big data or IVR, or whatever? Nothing is off the shelf anymore. You cannot just buy software and plug it in and be like, Yep, we're good to go. It is all about how it works inside your organization. And it's about technology integration, to be sure, but it is also about people integration and process integration. And that's usually what companies forget to do. That's when they call me.

Tim Bornholdt 31:31
So it's a good it's a good problem, for you, at least to have.

Jen Swanson 31:35
Yes, and I love that stuff.

Tim Bornholdt 31:37
I really liked when you were talking about the templates part and that's where I wanted to go next was, I think, if you were say like coaching a basketball team, you may be able to find a template that the LA Lakers use for their practices. But if you're coaching first graders, it's going to be a different template. Like you know what I mean? Like you could take the template for the Lakers and maybe apply it to the Trailblazers or to the Timberwolves, but you're not going to necessarily want to apply it to your peewee basketball team. So I think a lot of it applies in a similar way here, like where one of the things I wanted to touch on was like the difference between consulting digital transformation with a Fortune 500 company versus like a startup or kind of in a growth stage. And I think if I can make a presumption, and then I do want to hear your answer, but I would assume you'd say that it's kind of the same thing. There's some high level things that are the same, like basketball is basketball, you put the ball in the hoop, that's what you're trying to do. And it's the same with business, you're trying to bring in revenue and provide value for somebody. Now how Optum does it, for example, is going to be way different than how The Jed Mahonis Group does it because we're providing different types of value. But at the end of the day, you still have similar mindsets, and you might have more advanced mindsets when you have a large corporation versus a small one. So again, getting to my question, what are some of the differences and similarities when you're working with huge corporations versus smaller and up and coming corporations for their digital transformation strategies?

Jen Swanson 33:09
You know, you are correct in saying that there's more similarities than differences, right? So I really like that basketball metaphor and I'll just tell you right now, Tim, I'm totally stealing it.

Tim Bornholdt 33:23
Good. You're borrowing inspiration, just say baseball and then there you go.

Jen Swanson 33:31
Because here's the thing, is that I think when you have a playbook like that, just like you said, you cannot give it to your fifth grade, you know, whatever. I'm not into the sports ball, so forgive that metaphors here because I won't be able to fully integrate. But you can't give it to your fifth grade peewee team because you don't have the talent of a particular set of players like you do on the Lakers or the Timberwolves. And even going from the Lakers to the Timberwolves you have different talent, you have different skill sets. And, you know, product management for me, I say often, is a combination of art and science. So the science is some of the methodology and the framework, and things like using design thinking or agile software development or some of the ceremonies and cadences and terminology that you get with agile, that's the science part. The art is how you deploy the people you have. And I think actually this is why the investment is strong right now in digital transformation is companies are saying, Alright, look, the world is a crazy place. We don't know what's coming next, but we're going to try to figure out how to get more out of the people we've got and the teams we've got, and how can they work together better. Product management can help you do that because you start to look and you say, Okay, who do we have that has particularly good skill sets in these different areas and with training and good expectation setting and some artifacts and some templates, can we start to say, This is how we want you to work, and try it out and tell us what you learn. And then we're going to iterate on it in the next sprint. Maybe you're going to add in a different kind of a meeting that helps bring people together in a way that didn't in the last one. That iterative process is what is really healthy for teams. And that's where it's the same whether you are talking about a startup or Fortune 500.

The difference is that in a startup, you've got way more people who are trying to do six jobs at once. Right? Because they're smaller. Depending on where they are in their growth stage, there may be one person who is product manager, product owner, tester, maybe a little bit of marketing and, by the way, he also works with the executive team to prepare work for investors. Okay, that's a lot of responsibility and a lot of fracturing of attention. And so the challenge there is to figure out what the right focus is and how to really get your product person or, you know, two or three people to really focus on the most important, most impactful work in any given day. And sometimes that is just as simple as a really good Kanban board and you just work that plan, right? Because they are in constant firefighting mode.

Then you've got companies that maybe are growing and all of a sudden that one product person is going from one person to a team, or one team to three teams. And that presents problems because all of a sudden, now they're filling seats, and they're bringing in people who have done product at different places. And you've got to start to define how your company is going to do product and how you're going to run things so that you bring in the best experiences from those people who are coming from BestBuy or Target or Optum or wherever they're coming from, where they learned product, and they're doing that way of doing things. You're bringing them in and you're saying, Okay, but that's great and we want to continue to evolve. But here's how we're going to do it. Here's what our process looks like, here's what our ways of working are.

And so that's one set of challenges. Then when you've got an enterprise, where you don't just have one product leader or a handful of product people, maybe you've got 30 or 40 people who call themselves product managers across the organization. And some are doing product management and some maybe are doing more like product marketing with a little bit of product management in it and there's a lot of diversification of expectations. And the executive team is trying to get their hands around exactly what's happening in product across the enterprise and figure out how to prioritize and scale. And that's a whole different set of problems. But ultimately what it really comes down to for me, I always look at what outcomes are you trying to achieve? What people do you have? How are your teams working together? And what's out there that you could use? I mean, I joke sometimes with my product friends that Google is like my number one place that I go, right? Because there are times where I'm like, Well, I know what my prioritization framework is, right? I've got two or three that I always go back to. But they're like, old comfy slippers. Maybe there's something better for this particular team, because there's some sort of nuance here. And then I go out and I look at it and go, Oh, well, I like this parts of this one, and I like parts of that one. And I can see how we could mash them together. Like there are no new ideas here. There's just new ways that teams have to sort of bring information in and think about how they're working. So that's a very long and winding road of answering your question, and I hope I did. But for me, it's the same questions. It's the scale or the context that's different. And that being said, one Fortune 500 company is nothing like the next one. You know, I joke, every company thinks they're a special snowflake. But when it comes to this stuff, they kind of are, right? There is not a like, buy the book, read the book, apply the book to your company, and you will achieve digital transformation, right? Like there's just a lot of paths to it. You've got to commit, you've got to, you know, understand your context, understand your people, commit to a path and then you know, support those people as they go through it. And you'll notice, I talk a lot more about people than I ever do about technology. Technology is just a tool, but man, the people, that's where it's at.

Tim Bornholdt 39:55
Oh, absolutely. And it seems like the more that I read, cause you know, I've never worked in a massive corporation before. I've always done freelance stuff or worked for small companies. And so as we've been growing our business here, digital transformation is something that keeps popping up again and again. And to me, it's like, it seems like a no brainer, because just like we talked about earlier about our entrepreneurial career ADHD stuff, where it's like, you kind of need to at some point arrive to a solution. And with being an entrepreneur, you're putting on 6000 different hats and just trying to make sense of all the chaos. And it seems like digital transformation is kind of making sense of all the chaos in your business, but also trying to tie it all in together so that you have one cohesive strategy going forward and that strategy is, well, things aren't always on fire. Like I don't want to put that thought in your mind of like when we're building out digital technology and stuff, it's not that things are always broken and need to be changed. It's that you just need to be aware that the landscape is changing all around you. And even if you build your solid foundation business here in 2020, what's going to happen in 2030? Especially 2040? But even 2021, things are going to be different. And it's how can you introduce the idea that your business can evolve and adapt with all of those changes and that, like you said to your point of the people, putting the power, not necessarily being a board of 20 people that are saying, This is the way we're going to do it, and here's your marching orders and go. It's not so much of that type of structure. It's more of empowering your people to work together to find creative solutions using technology and staying abreast of all the situations and all the changes that are happening in the world and how you can adapt that to your organization.

Jen Swanson 41:50
Yeah, and so you've heard me probably use the word scalable about six times in this interview, and I talk a lot about that because I actually think that that's where the real juice is in digital transformation in 2020, and for the next couple years, because I think most companies have made the investment in the underlying infrastructure. But when they implemented things, they didn't integrate them. So you have the standalone systems that are put together with bubble gum and dental floss, right? Like they just don't hang together and the data doesn't flow from one end of the company to the next. I think, collectively, businesses are waking up with a little bit of a hangover from the last decade where it was, you know, I'm throwing no shade on Salesforce. I really believe that's a good solution for a lot of companies. But it was like, Hey, let's get Salesforce or let's do this marketing automation platform or let's get that or let's do this or new over here and new over there. We're going to replatform that, and they did it but they didn't necessarily do it thinking about the full ecosystem because they assumed they would do it later. Right?

And so, all right, I'm going to be on a soapbox here for a minute. So just prepare yourself. So they assumed they were going to do it later, right? Because they implemented it in a waterfall way where they said, there's this project we're going to have, we're going to implement x platform or x capability. And it is going to have a start, we're going to have a big kickoff. There were probably t-shirts and cupcakes, and they launched it, and then they reported on it for 12 to 18 months, and right around month 12, the executive team starts to freak out and they're looking at their watch. They're saying this has really taken a long time and, you know, you're half a million dollars over budget or a million dollars over budget or $10 million over budget, or whatever it is. And then they got people coming back saying, Well, we're going to have to descope this and descope that and then they delivered something and then you know, maybe they got a warranty period where they had people working on it and kind of cleaning stuff up for two or three months and then those people moved on to the next thing. And they assumed that at some point, I don't know maybe magic fairies or garden gnomes were going to come in and do all of the stuff that was going to connect it to be the value that the sales people who came in said that they were going to get. But all of those people who worked on it, who have their DNA all over that system or platform, have moved on to the new project in town, or the new project in the company, and they're not working on it anymore. And that connectivity is not happening. So now all of a sudden, companies in 2020 are waking up going, Alright. I have a CRM that doesn't really do what I need it to do, because I've got four different instances that don't really talk to each other because we descoped that when we put it in. We've got websites that are a proliferation of a stand alone micro site, different branding, blah, blah, blah kind of stuff. Like, they're waking up going, what did we do?

And now what do we do? Right? What happened? And where do we do from here? And that's really where I think the recommitment and sort of the fashionable thinking about digital transformation has come from is they're saying, Oh, we actually have to work to connect all this stuff to make it work together. And we don't know how to do that. And then it's also going to change because we're going to connect up these two systems. But next year, we're probably going to replatform that system. So how are we going to do it? And who's going to take care of this stuff over the long haul, right? And that's really where that shift from I was talking about, the shift from project to product mindset, is. Projects have a beginning, middle and end. A product is something that goes on, I don't want to say forever because no product is forever, it's probably three to five years and then something new is going to come along or you're going to have to upgrade, then that's fine. So if you want to think about it as a capability mindset where you're really thinking about this particular functionality or capability, not necessarily tied to the platform, but the ability to do the work that it enables. We care about that now. We're probably going to care about it in five years, right? Like, this is something around revenue management, or it's around lead gen or it's around, you know, customer engagement. Those things aren't going away. The platform that supports them might change, but those capabilities will always be important to our business, but what they look like are going to be different and we need somebody in charge of them to make sure that we're making good decisions and that we're connecting them up and we're making sure that they all work together right and that's really, I think, where many businesses are waking up today, or in the last year, and going, Oh, crap, I don't think we did that right. And now what do we do about it? Okay, over rant.

No, that was good because that spawned like 30 questions in my head and I want to be mindful of our time. So, this might be a dumb question, but I was thinking through that hangover process, right, because that kind of a hangover of your business where you implement Salesforce, you know, again, no shade, but whatever tool that's supposed to be a monolith to check one box and it did everything. When that organization is going through that hangover process, and they're sitting there thinking, how did we get here? And what can we even do next to move on? I would assume that that's like the perfect point to contact you. But who is contacting you? Does digital transformation happen as a result of a middle manager, somebody in charge of a team, that says, Hey, we need to spur it up and have our organization do this? Is it coming from on high from the executive team saying, We need someone to help us make sense of all this and move forward. Or is there not really one person it comes through? Again, dumb question, but I'm just really curious, like, how does that happen? Who comes to you?

Well, you know, a lot of times it will depend on the size of the organization. But there's two places that I really tend to make an entrance into a company and a lot of times it's with like a senior leader, not necessarily a C level executive. Although sometimes that has happened, you know, a CIO or CTO reaches out to me and says, Look, we've been trying product, it's not taking hold, we've got to do better. We're under some pressure from the market, a regulatory body, the world and what's happening in our world, you know, customer expectations, and we're not doing it right. We need some help. So, usually, it's like a Senior VP or like a CTO, CIO kind of person. It's usually a company that does not have a Chief Product Officer. Although that's not to say that I can't help companies that, you know, sometimes I'm a few extra arms and legs to be able to come in and help have a little bit more influence and span of control when there is already a product organization stood up. But it's usually, again CTO, CIO, CMO, or Senior VP in those kinds of roles who are saying, Look, IT and business, it's not working. It's not working. And you know, it's like couples therapy, we know we need help. We don't know what help, what that looks like. But we know we're not doing it to the best of our ability and we're not getting what we need out of it. Everybody's frustrated. And that's usually who calls me.

In smaller organizations, especially in startups, I tend to get called by the product person who is not the founder. It's usually one of the people that the founders hire, after they've got some funding. It's probably series A, you know, maybe seed round, they hired a product leader. And that product leader has a huge job. One is to build whatever it is that they're selling and that they're going to get investors and that they're going to have to start to show revenue and all that kind of stuff. But the other job that that person has is to wrestle away the product strategy from the founder, because the founder has it all in his or her head and getting it out of them to be able to run with it, which is an exercise in trust building, and process and all that other kind of stuff. Like sometimes I get called from those people and they're like, I just need help. I just need like, any coaching. I need you to come in and be the founder whisper to me to tell them that's going to be okay. Like I need that kind of help.

So those are kind of the two places. So in larger organizations, it tends to be a leader, not a top level leader, but a senior leader who says, This is a priority for us. We have to do better in order to compete, to win, to grow. Whatever the outcome is. And we don't know how. Can you come in and help us? And so that's usually my entry point in. And actually, I always say to people, when I network, people say, Well, how can I help you? You know, how can I help you find clients. And I say, When you're sitting, this is, again, pre-COVID when we actually sat and had coffee and drinks with people, do you remember that? And you're sitting with someone, and they kind of tilt their head and they say, I don't know what we should. I don't know what to do. And they kind of look off like, you know, they describe their problems about the conflicts between how business is operating and what they're asking for from the technology organization and where things are disconnecting and falling apart and they don't really know what to do. I'm like when that happens, say, You know, I know who you should talk to. You should talk to Jen. Because usually I can come in and suss out what the real problem is, but like, it usually feels like conflict or like missed opportunities or misaligned expectations between technology and business, or, you know, technology and marketing where they're like, we're just not quite matching and we need to do better. And we don't know how. And that's usually where I come in.

Tim Bornholdt 52:18
I think anyone listening to this that has that same thought of like the thousand yard stare of, there's a problem going on. And I don't know what to do. I think you would be the first person that all these people should call, because even in just the short time we've been talking, it's opened up my eyes to a lot of things in my own business. And, you know, I'm not a Fortune 500 company, yet. But it's good to know that there's somebody that you can turn to because my last question I was going to ask you was, what's once actionable or some small step that someone can take today if they want to move their organization to more of a digital transformation mindset? And let me actually just hear your answer first before I say what I assumed it might be. So what do you think would be one step that people can take away here today if they want to move their organization into more of a digital transformation mindset?

Jen Swanson 53:14
Well, okay, that's a really hard question because like I could answer books I think they should read or podcasts they should listen to. But the bottom line is, I think, the first thing, so that idea that when the masks fall from the ceiling, the first thing you do is secure your own air, your own mask. And so what I would say is the number one thing they can do is to check their own assumptions about what they think they're getting out of digital transformation. And if the words, when are we going to be done or can't we just, come into their language or come into their mind or they find themselves saying that to people, I would ask them to just stop and to really get real about what they want the outcome of that investment, that technology investment, to be. Because I think when you start to separate out, Well, we need more efficiency. And we need this and this and this, it can feel really overwhelming and to say, Look, what is the most distilled down, you know, whether you want to use five why's or whatever technique, but just to say, Why do we need x? Why do we need Salesforce? Why do we need the marketing automation? Why do we need to invest in the data lake? Is it to build trust with our customers? Is it anything else like that, because once you can kind of center on that top, that really fundamental value that you're trying to achieve, and you start to separate out the noise, first of all, if you can communicate that to your teams, you might be able to just get a little bit more energy.

But I do think there's no shame in asking for help. I think about companies like Cprime who, if your agile teams just aren't functioning well, there's great resources, there's trainers, there's online education, there's people like me, there's great books to read, there really is a lot of resources out there. But knowing what you want out of it is the most important thing to sort of begin that journey. And not just because we need it, or because everyone else has it, or because it's parody. But fundamentally, what are you trying to get out of this investment? And really getting clear about that can help you then sort out the noise and get to the things that you really have to focus on. It's not a great answer.

Tim Bornholdt 55:41
I disagree. It was different, actually, than what I was thinking you were going to say. So that's perfect. I don't even remember what I was going to say. It was a perfect answer. And I think it's a perfect place to end this off because I think everyone should turn off this podcast now and give you a call. So how can people get in touch with you and start going down this process of digital transformation?

Jen Swanson 56:07
You know, probably the best way is, I am on LinkedIn at JGSwanson. So that is J-G-S-w-a-n-s-o-n. And so if you Google me, I'm the one that's laughing in my LinkedIn picture. So there's not a lot of other Jen Galpin Swansons out there. Yeah, so that's probably the best bet. I also have a website at JenSwanson.net is the other place that people can find me.

Tim Bornholdt 56:37
Perfect. It's not the Jen Swanson that's scowling in her LinkedIn photo.

Jen Swanson 56:41
No, no, no, I laugh a lot. If you can't tell on this podcast, I laugh a lot. It's part of my core value.

Tim Bornholdt 56:49
Me too. I love it. Jen, thank you so much for your time today. I really hope people took away a lot about digital transformation and really appreciate you having the time to be on the show here today.

Jen Swanson 57:00
I really appreciate the opportunity. Thanks so much, Tim.

Tim Bornholdt 57:04
A big thanks to Jen Swanson for joining me today here on the show. You can find Jen on LinkedIn. It's JG Swanson, just look for the laughing profile photo. You can also find her at her website jenswanson.net. Please look her up. She is awesome.

Show notes for this episode can be found at constantvariables.co. You can get in touch with us by emailing Hello@constantvariables.co. I'm @TimBornholdt on Twitter and the show is @CV_podcast. Today's episode was produced by Jenny Karkowski and edited by the munificent Jordan Daoust.

A quick housekeeping item, if you have one minute to spare, I personally would love it if you left a review for the show on the Apple Podcast app. It shouldn't take much time at all and really it helps new people find the show. I don't get how, that's just how it is. So please head to constantvariables.co/review and we will link you right there.

This episode is brought to you by The Jed Mahonis Group. If you're looking for a technical team who can help make sense of mobile software development, give us a shout at jmg.mn.