Jennifer Swanson on Reinventing Business for the Era of Data and AI

Hello and welcome back to Data Driven. Our next

guest on the Data Driven podcast is none other than the digital diva

herself, Jennifer Swanson. As the CEO of

Tuckpoint Advisory Group, Jennifer doesn't just navigate the

digital transformation landscape. She practically

terraforms it. With an explanation of digital

transformation that's so clear and compelling, it could illuminate the

darkest corners of the Internet, Jennifer has the uncanny ability to

demystify the complexities of our digital age.

Her insights don't just scratch the surface. They

dive deep into the heart of how technology reshapes businesses,

cultures, and our very existence. Now on to

the show.

Alright. Hello, and welcome to Data Driven, the podcast where we explore the

emergent fields of artificial intelligence, data science, and, of course,

data engineering. And with me, is my most

favoritest data engineer in the world, Andy Leonard. How's it going,

Andy? It's going well, Frank. How are you? I'm doing alright. It's been a

wild week here at, Chateau Lavinia, and, you

know, we've had, just got back from a funeral out of state, and,

you know, it's all sad and all. But, Yeah. I it has taught

me to appreciate every moment, because our future

is not guaranteed. So true. How about you?

How things by you in Farmville? Things are good. You know,

we're in the end of February. We're doing this recording on February

you know, the trees have been budding now for about, I don't

know, 2 or 3 weeks, and you may see me do, you know, rub the

corner of my eye. Pollen seems to be getting there. I actually washed

pollen off the windshield earlier today. True story.

Not a lot. Not a lot. Just a just a little bit of a

dusting, but it was definitely pollen. Yeah. And we've been

sneezing. We've had our than that. Our interesting.

We've had our first, start of, fake spring.

It's, like, 50 degrees today. And then tomorrow, it'll probably be, like, you

know, below freezing. Might get snow again. Who knows? But speaking

of snow, our guest today is from a place

known for lots of snow. Except this year.

Right. Except this they were just talking about that in the green room. Yeah. That's

right. So I'd like to welcome Jennifer, Swanson to the show.

She is the founder and CEO of Tuck Point Advisory Group,

a collective of digital transformation experts helping world

class organizations integrate digital technology into all

areas of their business and significantly improving customer experience and their

operations. So this is the, I guess it's second episode where we talk about

customer experience and customer, success, but

digital transformation, if there's ever been a loaded word.

I know. I know. What is that? Because I I when I was at

Microsoft, they they had this, the previous leader of the

particular group I was in had had something called Digital Transformation

Academy, and I wasn't really sure what it was about. It was

Yeah. To to me, it was an excuse to go to Vegas in this particular

executive to show off her her boat collection.

Sure. But I'm pretty sure digital transformation has more to do with

actual real work. Well, I think so. But, you

know, there's still a fair number of people walking around showing off their boats

and Rolexes that are working in digital transformation too. I

I will tell you that, I usually lead

with digital transformation because I can usually gauge

whether or not somebody is gonna have the slightest clue what I'm

talking about when I say, well, sure. I'm a consultant. I work in digital

transformation, and then I kinda watch their eyes. And if they glaze over,

I leave it at that. And then I ask them about whether or not they,

you know, watch the latest whatever sports ball thing or whatever, and then

we kinda move on from there. Or if they lean in and go,

you know, what do you mean when you say digital transformation? Then I go,

They're at least interested. Right? Like, at least they know something about this.

And really honestly, for me, digital

transformation is has lost all meaning. Right? It is

really for me the end tuck point. We really actually focus on operating

models and how companies work with technology and

people to, like, bring value both to the

company and the and the people that they serve. Right? The employees,

the customers, clients, what have you.

But nobody would understand that, and that sure as heck doesn't fit on a tagline

on a website or anything else like that. So we we use the vernacular of

digital transformation because that's the space in the market that is sort

of most often discussed. But, actually, the way we

describe digital transformation was in the headline you read, which is

technology infusing every part of the business. Right?

So 15, 20 years ago, maybe 25 years ago,

technology was the thing that drove, you know, our

email, maybe our the data stack, the, you

know, the customer database, the, you

know, the the big computer in the backroom. That's actually how my dad got his

start. He worked he worked with the computer. Right?

And that was in the giant the giant clean room. Right? The

computer. Nice. Back in the sixties

seventies in grocery. That was where he got his start.

Right? Technology was this thing that sat over there, and it

was, like, a part that was one part of the business,

and then the rest of the business operated sort of independently

from technology. And clearly, we are 50, 60 years

from that genesis. And where we are now is that

technology is the business and business is technology, and there's no part

of any business anywhere that is not

touched by technology, even in businesses that are

not technical by nature. So I always tell the story,

and I always say, stop me if you've heard this one. But, you know, take

the most offline business you can think of, and I always I go

to masonry. Right? And maybe because we've we did a massive

backyard patio project last year. Right? So here you have

people who are they're ordering

patio pavers and bricks and mortar and all of that stuff.

Right? So they are coming out to my house, and they are working in an

incredibly manual manner of

measuring and, you know, leveling and everything in there,

building things with hands with

hands and and materials. But guess what? They have to order all of that.

They've got supply they've gotta manage supply supply chain

issues. They've got labor. They have to be paid.

They have to be hired. People are finding them online

through review sites, through everything else. So even these

considered, like, offline businesses still have

technology all throughout their business. And the question is,

how integrated is that? How well is it

managed? How intuitive is that?

How, easily, how easy is it for

employees to manage it? How easy is it for customers

to use it? How does all of that enhance the customer

experience? And for small companies, sometimes

the answer is it's great. Sometimes for big companies, the answer is it's

great. And usually the answer is, well, you

know, it leaves a little to be desired. And that's where we

come in to really help think about that end to end experience, whether

it's on the employee experience side, the customer experience side, or sort of

the full stack, right, to really think about it, you know,

nose to tail, stem to stern, and think about how that full

experience is gonna be integrated and that technology end to end

integration is gonna happen. The you can't do that with

teams that are functioning in silos. You have to have cross

functional teams. You have to have cross functional organizations. You

have to have funding models that support that. You have to have

governance models that support that, and you have to have very different kinds

of mindsets that are different than when technology was,

again, the computer in the room over here and business off doing

their own thing. So that's kind of my manifesto of who I am and

what we do. That is the single best sorry. The

definition of of digital transformation. The single best one I've

ever heard. Aw. Now Thank you so much. It it's awesome because, you know, you

you bring up a good point that all of the way companies

are structured, it was the computer people were kinda

off on their own. Yeah. And when

I switched computer science when I was young but a young man in university,

my mom was horrified by the fact I would be one of those weird

people in the basement. Yes. And He has with moss on his

back. Right? Yeah. Right. And, you know, it's,

my home office, ironically, is in the basement of the house. But

Sure. I have a window. But, and

and, plus, you know, a lot of the the way that organizations are

structured are very much in that that kind of that

pre kind of modern era And you bring up the point, like, cross

functional teams, cross functional budgets. And Yeah. You know,

it it's almost like and correct me if I'm wrong, that the

the the the way that companies are organized and structured

is still 60 some odd years behind the curve. Yes.

Yes. Sorry, Andy. I didn't cut you off. Yeah. Sorry.

No. Sorry, Andy. No. That's okay. You asked what I was going to, so we're

good. I was going for cross functional and and a little more depth there.

Yeah. The, and that's the part that I think is really interesting is

that I think the first wave of digital transformation was, let's

apply technology to everything. Right?

And not to steal a very another very

overused phrase, but that's putting lipstick on a pig. Right?

Because what the assumption was, we could just

take technology, you know, and

smack it right on top of all of the old structures, all

of the old ways of doing things, the old, you know,

sort of siloed structures, The the

manufacturing model of we, you know, we do something over

here, and we hand it off to somebody next to us who hands it off

to somebody else who hands it off to somebody else. And, really, modern technology

is not built that way. Right? Modern technology really has a much more

organic structure and has to be built in a more thoughtful

strategic end to end manner if you're gonna get the the ROI

out of it. And so that's where

operating model transformation comes in. Right? And that shift from

project management into product management and really thinking

about that end to end structure. And so I think that's really

where I believe that second wave transformation piece is coming

in, and that's where we find you know, that's our market is in that

second wave where people will ask me, well, what kind of technology do you work

on? And we're like, yes. All of it. It doesn't matter because it's

it's not about the technology. It's the organizations that are not

seeing their investments in that technology or those data

structures or whatever it is, whatever those investments were in that first

wave, the executive teams are going like, wait a minute.

We were promised x, y, and z, and we're

not seeing it. Why not? And it's because it stopped with the

technology, and it did not go deep enough into ways

of working and into structure and into culture and

into governance and all those other pieces.

I think back to when I was a younger man,

and I was working in a large chemical company, and they had set up a

website. Right? They set up this big ecommerce thing. There's obviously the website

to kinda explain the company and all that, but they had this idea where you

can order directly on the web. And, ultimately, what happened was

somebody got an email and somebody manually key in the order into SAP.

But it. But you're right. Like, it was it was really

more of a pressure to get some kind of way that people can

order online in a way that

it was a very much a facade, and it was very much a duct tape

solution. But I think back, and I'm like, you know, if I could go back

in time and tell myself something other than the winning lottery numbers, it

would be Yeah. You have to think about the business

structure that you're operating in as an IT person

and very much so these are not IT

experts. These are not And and the people on the board, they get these

promises from vendors, from the news media, from

this, and they don't see it because it's

people process and technology. Right? Like, in in technology, you know,

one thing of it. And, AI, I think I'm seeing this all

repeat at kitchen kids of AI. Okay. So I'm not

crazy. Right? So is this kind of like AI? And I get a lot of

customers say, we want to use Gen AI. For what? And

when you challenge them, they kinda say, well, we want a chatbot.

K? For what? For what? And

Yes. I don't think people are really fully

I I encourage people to think beyond the chatbot. Right? Because there's gonna

be more use cases for Gen AI. But I

think the fundamentals are people, process, and technology. What's

your data supply chain look like? Governance. Right? You said governance a number

of times. You know, you you're on the short path

to being one of my favorite guests. What does

governance mean to you? Right? Because you're probably talking about more than just data governance.

I am. Although data governance is a really important

part of it, I just think that, inside of organizations,

which, by the way, governance makes me, like, the least popular person at any

dinner party, but I really do like governance because what

governance says to me is that there's inside of an organization.

There is a predictable,

and it doesn't have to be overly structured.

It does not have to be onerous. It does not have

to be, you know, death by committee because, good lord, we need

fewer of those. But that does have to be a predictable

method by which,

ideas

get floated up, prioritized,

and green lit, right, according to the outcomes and

strategies that are decided as the most important ones at the top of the house.

Right? So in a in a high functioning organization in my mind, right,

in a really modern, forward thinking, outcome oriented

organization, you have an executive team saying, we

know what direction we're heading, and we know what good looks like. Right?

Which means they have a clear strategy where they're gonna play and how they're gonna

win, and they know they've defined outcomes. Right? We

they know that's what, you know, that's what good looks like. They're not

saying we wanna make more money. They're saying,

you know, they're saying we wanna grow revenue through,

you know, organic growth in this particular market. We wanna do

it through, deepening our relationship with existing

customers, like, whatever that is. Right? They've defined what good looks

like, and they've empowered teams to say, alright. Now given

that, we trust all of the business units

to now go define how they're going to do that within their own spheres of

influence. And there's there are those organizations are gonna come back and say,

alright. Well, we've got 12 ideas. Here's our 12 ideas. Which 3

should we be working on? Right? And governance is the method

by which the organization surfaces those

ideas, decides how those ideas are gonna move forward, and goes at

them because we can't that organization can't go

after a 100 good ideas. Right? Somebody

shared a quote, and I won't be able to attribute it. So I'm very sorry

whoever said it and whoever shared it with me. But, somebody

shared with me on LinkedIn the other day something that said, priorities

are like arms. Anybody who tells you that they have more than

2 is either delusional or lying to you. Right?

And so That's a good quote. Like,

the those organizations have to have a method by which they're

they're saying not even no to things,

but not now. Right? And so governance

organizational governance to me is a way by which

strategy is set, outcomes are defined, and priorities are

determined. And the whole organization holds hands and says,

this is what we're working on, and it's okay. Not it's not

just okay. It's required that we're not working on the

things that don't fit in that bucket.

Right? Because that's the only way we're gonna be able to get things

done that we say are important. And so

that governance looks different in different companies. Right?

But on some regular basis, the leadership, you

know, probably 2 or 3 levels down, all have to come together and hold hands

and say, we know what's important. We agree what's important, and

we're committed to what's important. Right? Now when you get down into

data governance, there's different layers, and that takes on a whole layer different

layer of structure and meaning and things like that. But from

my perspective, that enterprise governance is

that ability to get everybody to hold hands

on priorities. You know,

it sounds sorry, Andy. It sounds a lot like cultural

governance. Yes.

Yes. Because how many times have you worked at a

company where

you get it. There's, like, a executive board meeting and everybody nods at

the strategies. It's, yes, this is the best strategy we've ever had in a 100

years of whatever. And you look at it and you go, first of all, it's

no different than the strategy we had 3 years ago, but okay. And that there's

not really a lot of meaning there, and I'm not really sure what it means

for me 3 levels down and how I'm supposed to decide what to work on.

Right? Yeah. And every vice president in

that company is gonna go back to their desk and work on the same projects

that are their pet projects because nobody's really holding them

accountable to stop working on the stuff that they just wanna work on because it's

their pet project. Right? Yep. It's a really hard

thing to get everybody in a company to take some bold steps

to say what's in and what's out. What we're

doing and what we're putting, we're either saying no to or not now

to. Right? Yeah. It's really hard to do

that. It seems like the no or not now or

not yet. That that seems to be the hard one.

Sure. Sure. Yeah. Wow. Sure.

So that's why we do a lot of, my my advisers

and I end up doing a lot of what we call as therapy, a

lot of therapy with the executive teams. And the other

joke, I have a lot of material that I use, but a lot of it

is I come in and I say, we're gonna use the f word a lot.

Feelings. We're going to talk about our feelings a lot. That's

funny. I like that. And that's what an f word I don't have to bleep.

Right. We had our first episode go

live, I think, the overnight where it was the first time we bleeped

it. It was just kinda funny. So, but,

the interesting thing is is that you're right. Like, it it's it's really

people and egos. Right? Because Oh, yes. Some people on their on

their their pet projects. Like, how do you get them to walk away from

their pet projects? It's worth not walk away, put on the shelf for later.

Like, that seems like, a lot of therapy, actually.

Yeah. Well and some of it is too is the change

that people have to make from driving their own

agenda to driving the agenda of the company. That's a

big that's a big shift. From me to we

is a really big shift, I think, in a lot of this. It's a really

big part of why we have a lot of change management,

as a part of our services. Right? Because I think and we do

a lot in terms of, executive team dynamics because

that's really where a lot of this starts. And not just at the executive

team, but that next layer down. And, you know,

every layer of an organization sort of brings with it its own dynamics. What we

have found really is that oftentimes, it's not the executive team that has

the biggest challenge, and it's not the grassroots layer. Mostly, we

find teams, you know, product teams in particular,

even if they're new teams, you know, teams of folks that and of

engineers, especially engineers that have experience working

in agile. They're hungry for this. They're ready. They want the autonomy. They want

the empowerment. They're ready to go. You know,

some organizations do some work in transitioning project

managers and BAs into product roles. They give them training. They give

them support. When done well and done right,

those folks are hungry and anxious and ready to have that empowerment and that, like,

dedicated focus of having one thing to work on rather than being,

like, peanut butter spread on things all the time. Right? They wanna really

have that focus. So it's not the grassroots that struggles, and it's not

the executive team. But those middle layers, you know, we

always say what got them here is not what's gonna get them to that next

layer. And so really part of it is taking them through that,

that change management to building the change muscle to

say, like, you've got the right skills. You have to start to shift

how you deploy them and helping them feel safe in that

deployment that they might suck at it for at first before they're gonna get good

at it in that leadership in that leadership mode. And that's really

hard to do. It takes a commitment from that top layer, right, and support of

their people to say, look. You probably are gonna suck at this, and it's okay.

We're we've got your back. Right? That we're gonna, like, help you through it,

but that's a really big part of it. And that's why, by the way, what

have we just been talking about in the last 5 minutes? We have not been

talking one bit about technology, which is why the whole idea that this is

digital transformation is such bunk. Right? It's not about

the technology. It's all about the people. It's it's poorly named,

isn't it? It really is. Digital is almost

incidental. Right? Because it's about Right. It's

about the the people and the process, not

Yeah. Not the technology. Technology is Yeah. That's

interesting. I I I

I, some time ago when I I switched to working for a software company, You

know, I was just like, I just appreciated the difference because a

wise man once told me, and he's since passed away,

that all companies view software and

technology as a necessary evil. Just some view it as more necessary

than evil and vice versa and some more evil than necessary.

And I think I get it. And I think I know why that is,

is it really boils down to how things were originally structured. It was the

there was it it had the in a lot of companies, I'm not saying all,

but the the general flavor is IT

versus everybody else. Right? That's been my

experience. So Yeah. Maybe maybe, I'm alone

in that. But no it's all been varying degrees of that and and

and when you you know, I I I now under

see I now see that there's a much larger

reason for that. And that that's interesting. So

how do you how do you aside from therapy, I mean, how do

companies get around this? Right? Like, is this I mean, this is a mindset shift

that has to start at the top or start at the bottom and and the

middle management, the middle layers. Yeah.

Poor middle management. They're always attacked from all sides. But I know.

Like, how do you convince like, in a situation where you have

convinced mental management to change, what was the what was the commonalities where

they did change? Well, so I will tell you. I've been doing

this for a while, and it used to I used to take the stance of

you know, people would say, is it better to just rip the Band Aid off

and just, like, late like, reorgan a whole company in,

like, 6 months and just give get just do it everywhere all at once,

make a big mess, and then put it all back together, or do you start

small and roll it out? And I used to say it doesn't matter. I have

since come to a different understanding, and I think I've got, you

know, we can do it both ways. There's pros and cons to both for sure.

But I think I'm coming around to a preference, of

a maybe it's maybe it's my my my age.

Right? Is that my kinder, gentler moments of

that I think part the best way is is, like, luring

people with, you know, sunshine and honey. Right? Like, you find

the space where you can really prove the model with, you know, whether

it's one one team, you know, 3 teams, something.

And I really like this idea of taking a narrow slice right from top to

bottom. So you've got somebody from, like, say, a VP layer all the way down

to the bottom. So not just taking a frontline

team or 2 or 3, but really taking a, you know, like,

a a nice narrow slice from top to bottom and proving the

model all the way down. So you've got advocates who

can see and taste and really, like,

be your, like, oh my gosh. This actually does work right in

in, like, they can feel it. They can, you know, there's like a

visceral feeling to it, and they get excited about it, and then that and start

to spread it to almost like, you know, the teams adjacent to them and then

the teams adjacent to them and teams adjacent to them. It takes a lot of

work to find that right team, but almost in every

single circumstance, the effort to find that narrow

slice is entirely worth it. Right? If spend even if it

means you slow your roll by a month or 2 to find

just that right narrow slice until they're ready, or, you

know, 2 narrow slices and really, like, wall them off for a period

of time, 12 weeks, 15 weeks, something like that to get,

you know, the VP, the directors, the teams

themselves, get them formed, get them, you know, trained, get them up and

running, and get them doing a couple cadences where all of a sudden they start

to feel this energy of, I do own my own destiny. I

am in charge. I do understand how to work with my business partners. I do

know, you know, I can, we can

deliver value faster. It is better when, as a product

owner, I'm sitting with my engineering team and my designer

and my business partners, and we're solutioning in real time. Like, all of a sudden,

they start to feel that, and they're releasing things

in 6 weeks when they've never done anything faster than 6

months. And all of a sudden, they're going, oh,

this. And guess what? That that success and that feeling goes all the way up.

And I think once you start to get that, then it starts to spread, right,

like a good virus through the organization, and you start to go

sideways. But you have to have those you can't just have

those wins be at, like, the junior level, you know, at the

frontline level or the mid middle manager level. You have to sort of have

it all the way up, and you have to pick people who are gonna be

willing to, like, stand on soap boxes and say the same

tell the same stories over and over and over again, and then go sit with

other sit with their peers and be like, hey. I see what

you're doing, and that's an anti pattern, and you need to knock it off. Right?

Like, it can't just be coming from the consultants or from, you know,

whoever is the internal champion. It has to be like, you

can't this is not okay. Right? They have to be those

people have to be the people that are willing to go in

and be in battle with you once you go, which means it's sometimes it's really

hard to find those folks, but it's worth the time to find those

folks. You know? I was I was patting my heart because I'm loving what you're

saying. And I've seen this implemented a bunch of different

ways, and I just wanted to get your take on it because a

few minutes ago, you mentioned agile. And I've

seen from, you know, the bottom and then from

maybe the, you know, the the lower middle, I've

seen, scrum Yeah. Kinda coming

in and bringing with it some of the things you're talking about. There's

definitely a culture shift that has accompanied scrum

where scrum has been implemented successfully in my experience. And

I also see, you know, kind of spiders out again from

that lower middle level down into

more or better or starting DevOps

and and those sorts of, that those sorts of thinking.

Where where I've not seen here's where I've seen it fail is when

people try to take just that piece that works well at the lower

end and then apply it up. Right? Yes. I've seen

that fail a number of times, and and I don't know why.

And it sounds like what you do is you're looking for that

entire stack, that that Yes. Silo, that top

to bottom, and you're fixing the rest of it. Yes.

And so I'd love to love to hear you speak to that. Because let me

tell you how many organizations I've walked into where the first thing

they say to me is, well, we can't do that here because we tried

agile and it didn't work. And I'm like, okay. Say more. Tell me more.

And they're like, wow. You know, fill in the blank

how many years ago? 18 months ago, 3 years ago, whatever,

last week. I don't yeah. It kinda doesn't matter. We

we, we put everybody through Agile, and I'm like, okay. Wait. Hold

up. What do you mean by everybody? And they're like, literally the whole company. Then

I'm like, so just IT. Right? And they're like, no. No.

Everybody. We turned everybody in. Everybody was an agile team. So they went around with,

like, like, a

fairy wand and magic pixie dust. And they're like, you're an agile team,

and you're an agile team, and you're an agile team, and they gave out little

certificates, and everybody's an agile team, and they put them through, like, a little, you

know, whatever, like, a 4 week, 1 week, 12 week, whatever,

dojo, whatever. And they were like, you're all agile teams. And,

like, they didn't address ownership constructs. They didn't address, like

you know, nobody owned anything, but you were an agile team. And I was like,

okay. I know what the problem is.

You know? And I have at least a half a dozen clients in which that

is the exact scenario. Right? Wow. And and to come back

in and say, okay. So, yes, Agile's gonna be a part of this

story, but only once we address things

like, what do teams own?

Right? What is the experience or the capability or the product that

you own and then how you deliver on it.

Agile's the delivery methodology, but you don't start with

Agile because Agile's a delivery methodology. Right? The ownership

construct and the strategy has to be a

part of that. Right? And so, you know, there's no there's no magic

pixie dust in my tool belt over here. You know? And so that's,

I think, a big part of it. So what's the opposite of that? I

mean, so we've we've talked about kind of the delivery model. People at the bottom,

lower lower middle and down. What then what is

the complimentary part of that that's from there up?

Well, some of it a big part of it is getting

leadership to understand that they no longer

I'm just gonna call a spade a spade. They no longer get to say,

the shorthand that I always have is they don't necessarily get to say that the

button is blue. Right? They don't get to say

they don't get to define the features. They don't get to

say, I want you know, in the data realm, their

job is not to say to draw on a little Post it note what they

want the dashboard to look like. That's not the point. The

point is, what questions are you trying to answer? What

problem are you trying to solve? What is the customer need that

we are trying to meet? Right? And by the way, who's the customer? Right? Like,

help define that at the VP and d director level. When

you are talking about that top of that leadership stack, that is

their job, define the market, define the customer, define the

problem. When you are getting to product

teams, their job should be to set take those problems and

say, we know how to solve those because we understand those

customer problems, and we understand our products, and we know how

those things can come together. In the data realm, it's no different.

We know what problem what questions need answering. We know how we wanna use the

data, what insights we're trying to drive. We know what corners we're trying to

see around, and those data teams know what is in

every single slice of that data lake. Right? They know what's there. Data

visualization experts, data scientists know how to bring that to life,

but you're not gonna, like, draw me a dashboard anymore. That is we're done with

that. Right? We are here to those that middle layer is here to be

the experts that you are paying them so handsomely to be. Right?

So I I I don't wanna cut you off, but I hear 3, you

know, 3 tiers. Yeah. I hear executive, you know,

director level. I hear product management. Yes. And

then I hear the people that I was speaking to earlier, the

the lower, middle, and down. And that's that is a different

way of looking at it. Yeah. And the issue is is

that they all have a role to play. You

have got to get those leaders out of trying to

play all three roles because that's not

their job. Their job needs to be forward looking and outward

looking so that everybody else can be the experts that they are

paying, that we're all you know, companies pay a lot of money for the expertise

at every layer. Let's let them be those experts and do their

jobs. That explains a lot of the failure I saw

in my younger days, and I'm older than you, Frank. I've seen

more. Probably older than you too, Jen. So oh,

Jennifer. I'm sorry. I didn't mean to shorten your name without mentioning it. It's fine,

Jen or Jennifer. It's all good. Just don't call me Jenny. That's the only one

I don't like. Don't do that. But, no, I've seen that. I've experienced

it, and I've wondered why there was this lack of harmony. You

know? And I felt like I wasn't being told what I needed

as as a person at the bottom. And I wasn't being told what I needed,

and instead, I was being told stuff that, you know, I already know how to

do this, and part of what you're saying isn't the right way

to do it. Some of it is. Right. But Yeah. You know? And

it's it's you really did a great job, you know,

spelling that out. And and I I think that's again, I'm gonna

echo Frank earlier and say that's probably the best explanation I've heard of that.

So really good. Fault. And also it's a hallucination.

Articulation. That's the way I'm looking for. Articulated that well.

Alright. Go ahead. I know. It's also like, oh, that's why everything always

was messed up. I don't wanna bring myself more work and and fix

it. But That's one. No worries. Like, it was, like, fundamentally, like,

the the you were trying to, like, get, like, a diesel engine to run on

gasoline or whatever analogy you wanna use. It's just not gonna work no

matter how much, you know, you try. One thought I

had, and this is something that I've I've wondered since I heard it. So,

once upon a time, when I was on a cross functional team, at a

very large, software company, and

for folks who can use LinkedIn, you can figure out who this was. I

was in the office in Washington, DC, and

I was on a cross functional team. And I heard somebody say the phrase,

and it's the first time they used it at that company that I heard it

was, we wanna swim in our own lanes. And I heard that, and part of

my, like, brain was like, uh-oh.

So given that cross functional teams seem to be

crucial for success in this, how do you how do you

address that? Because there's definitely a let's be real. We're dealing

with people. We're dealing personalities and egos. How do you how do you solve the

territorial challenges? Or is it more therapy? Well,

there's prob I would want to pull that person aside and say, can

we talk a little bit about what was said in that meeting? Right. Right. Well,

I was Right. Without the benefit of the I was but a plead in

that situation. But yes. I mean, listen. I think, you

know, without the benefit of a time machine. Right? Mhmm.

I think the reality is

human beings are always difficult. We will always be

difficult. It's never gonna be perfect. Cross

team collaboration and cross you know, just just general cross

functional collaboration is always gonna be challenging.

We all have our own areas of expertise,

but it's the additive power of them that is always

what's gonna make breakthrough innovation happen.

Right? Mhmm. 1 plus 1 is always gonna equal 4.

Right? You're not if you're only working by yourself or you're working within

your own swim lane, you're never gonna get to, like, next level innovation or next

level, you know, whether it's service innovation or it's

technical innovation or it's operational innovation. It doesn't matter. Right? You're

just never gonna get there. And, like,

human like, the human history is just it's like littered

with evidence of this. Right? It's like it's only when

cultures and people have bumped into each other. Right?

The salons of the 18th century when poets and scientists came together,

that's when, like, literally, revolutions happened. Right? Like,

this is how it is how it works. So

so then the only way to deal with it is to deal with

it through sort of nuance and

and sort of diplomacy of,

yes. We do all have to we have to own our own expertise,

but it is a a these are the opportunities. The collaborative

opportunities is where where we're gonna shine. So how do we do

that in a way that makes us all better? You know? I

just think there's no way around it other than to, like, greet it head on

and figure out a way to do it in an as nonthreatening away as possible.

But there's just there's always gonna be

somebody who's gonna be crabby about it, and so then you just gotta figure out

how to, like, make it work with them. But mostly, I think what

you do is you find the people who I don't

know. I'm always the one that's like, yes. Let's all get in a room and

do it. Like, I just think about my last corporate experience was with

a large health care organization in Minnesota. You can do the same thing

on LinkedIn. And I will tell you that one of the most thrilling

days of my career, corporate wide, and we all

have this, right, of, like, days where you just were like, this, I can't believe

I'm getting paid to do this work. Right? The most exciting days of your

work, was a day where we were literally having the

worst day ever. Like, everything was broken.

Things were really, really bad. I mean,

bad. And

3 or 4 of the smartest people I literally have ever worked with in my

career who were pretty high up. We were like, I we were

all directors, VPs, and we

maybe were promoted due to the Peter Principle. Right?

Like, we had all like, we were all really smart people as,

like, contributors, and we'd all gotten promoted and we're managing people, but

we were really, like, we were all really good doers. And then all of a

sudden found ourselves leading organizations going, why are we leading organizations? We were

really good doers. And so that included, like, a really smart architect, a really

smart engineer, a really smart product person, a really smart, you know, like,

strategy person. And all of a sudden, we were all VPs going, how the hell

did we end up here? Anyways, we all got in our room in the room

in our really fancy suits or whatever and, like, with whiteboards and stuff.

And we all went right back to our execution days, and we,

like, literally like, I still have a vision of the,

chief architect, like, loosening his tie, rolling up his sleeves,

and was like, alright. We're gonna figure this out.

And it was like 6 hours of the hardest whiteboarding I have

ever done. And, like, that was so fun. There

was no ego in that room. I was like, Alex, I have no

idea what you're talking about over there. Like, this makes no sense to me. Why

are we doing it this way? And it was because he is, like, 25 times

smarter than me, but, like, I've made him explain it to me. And in doing

so, he found some flaws in his thinking, and we, like, you know, figured it

out. But there were no egos in that room. We figured some stuff out, and

we fixed it. That was thrilling to me. I wanna

be around people like that, not the people who were like, Jen,

get in your lane, you know, kind of stuff. And I think you just gotta

figure out how to be around people like that. That is the best

answer to that because I often wonder I often think about that, and

I hear the term cross functional teams, and, like, I

I know that just the way the wind blows, you'll start

hearing, you know, stay in your own lane and things like that. And, like, I

understand both points of view, but there's a there's a tension

there, and I think that was a really good solution to it. I've I

ever since that happened, like, I'll say 8 years

ago since I heard that phrase, I was like,

that always kinda stuck with me. It was like and then I bumped into somebody

else who was on, a cross functional team

and was very stressed out, couple years later

when I rejoined said company. And,

she's like, oh, it's you know, she was explaining situation. I was like, oh, is

so and so saying that, oh, you gotta stick your own swim lanes again. Yeah.

Yeah. I was like, okay. Oh, yeah. That is an accident.

Right? No. Right. Right. Right. Like, you know, like,

now it's interesting. So I don't have any further questions unless you wanna switch to

the pre canned questions. I love this conversation. This is awesome because it helped Yes.

It helped it helped illuminate a lot of things that I never

understood why the situation was so blanked up.

See, it's therapy, Frank. I'm telling you. It's therapy.

I can look back now on a lot of situations where, I I mean, I

just I you feel like you're stuck in a Dilbert cartoon, and it's

just like, why why does it have to be this way? Or why is it

old? Like, Dilbert's popular for a reason. Like, why is that such a common thing?

Right. And, now that kinda

helps, I have a lot of more perspective than I it is therapy. Very well

done. Bravo. Yes.

Okay. So we can questions. Alright. So you wanna kick us off, or

do you want me? I'll kick us off. How did you find your I know

we're talking about data, but how did you find your way into this line of

work? Did this line of work find you, or do you find this line of

work? I found this line of work,

by a very long and winding road. And what I will just say, I won't

take you through all the nitty gritty details, but, I found this line

of work because as I mentioned earlier in the, in the interview,

my dad is a technologist and my

mom, my mom actually got her start, her

career. She's actually an artist by education,

but, didn't wanna be a starving artist. So she went to work in banking

and was a vice president in banking, but was really a

relationships person. Right? She did a lot of things with,

trusts, and she did fundraising late in her career. So she was a really good

relationships person. And so early in my career, what I figured out was that I

was bilingual. I could speak business and I could speak

IT. And, like, back in the day where that was a much,

thicker wall between business and IT, I could speak both.

And, I just always really enjoyed being able to

bring technical people and business people together and be able to

explain those two things, and that always served me well. And that's how I ended

up in this line of work because I really liked being the being the

connective tissue between those two things. That

is awesome. So what is your favorite part of this

gig? Oh,

okay. So what I will say is that as a consultant, I

get to, be a part of lots of

different kinds of companies. So I did work. I worked corporate

and, you know, client side for most of my career. I started

consulting about, 6 years ago,

and and

I would get impatient when I would work with companies. I'd work there for a

while, and then I'd be like, yeah. Yeah. Yeah. What's next? Like you know? And

I I worked a couple places long time, for a long time. My longest gig

was 8 years at one company, and that was fine. But, really, in those 8

years at that one company, it was Capella University. I had 5 jobs in

8 years, so it was never too long. Right? Like, I kinda I get antsy

after a while. And what I really like about consulting is my

ability to go in, learn a ton about a company and a

culture and meet all these different kinds of people and feel like I really get

to experience what it's like working in and with different companies,

but not but then being able to kinda, like, jump around. It's like a sampler.

Right? And I love that because I really find organizations fascinating.

And so it's that's my favorite part.

Interesting. So we have 3 complete the

sentences. The first of 3 is complete the sentence. When I'm not

working, I enjoy blank.

This one is hard because I work a lot.

So I'm gonna say I really enjoy

reading. So I'm a big reader, and I know you have some questions about books

later, so I'll just leave that one. I really enjoy reading.

Cool. So our second one is, I

think the coolest thing in technology today is

blank. I I'm gonna answer this

one with how easy it is to experiment. So especially with things

we talked about like chat gpt and AI, There's such a

low barrier to entry. Like, just being able to go and, like,

play around with stuff and experiment with it. I I think

that's fantastic. You know, again, 15, 20 years ago, you would have had to

have had special access to a university computer or whatever to

be able to do some of this stuff. And now it's just so easy to

just experiment and try things out. I see that with my kids too. I just

love it. That's

cool. And the 3rd and final complete the sentence

is, I look forward to the day when I can use technology to blank.

Okay. I have given this thought. I want a

fully integrated solution of laundry from

hamper to washer to dryer back

to drawers. Like, I don't even wanna touch it. Like, it has to be like

a like a closed system. I don't wanna touch it. I hate

doing laundry. It's like my least favorite thing. I've tried outsourcing as

much of it as possible, but at some point, I do have put it away.

And, like, I have to, like, touch it. And I just I wanna I want,

like, an a totally closed system. That's what I want.

I I have 3 I have 3 boys, and I totally get it. Yes. Yeah.

Yeah. Yeah. You know. Okay. Yeah.

So our next is, share something different about

yourself, but we remind all our guests we're trying to keep our clean rating.

Sure. Of course. Just so you know. Well so I will

share this, and it's something kind of new that I'm really enjoying.

My, oldest son is a freshman,

at in high school, and he has joined his robotics

team. Oh, cool. And they are entering

their big competitive season. And in fact,

he is going off to a regional competition

overnight, leaving his mother. I have to put him on a bus. Oh,

no. Oh, no. It's okay. It's okay.

He's done overnight camps before, so, like, we've been I've at least he's

been away from his mama before, but, but he had his

first kinda big competition. They kinda had a practice this last weekend, and he

was he's kind of a big deal on the team, and I'm very

proud of him. And, like, learning all about robotics competition, which is a

big national organization, and I'm really kinda

into it. And so we are a robot robotics family, and it's very

exciting. So That's very cool. Very cool. My

oldest is going to be a freshman in high school, and I was

telling them the other day, like, he's ready. I'm not ready.

Yeah. Just you wait until driver's ed hits, and then it's like a whole

other level. I'm not there yet. I'm I

was hoping for autonomous cars to solve the problem, but

I'm running out of time. Yeah.

You did drop the, the the hint about books. So Audible is

a sponsor. What books can you recommend? Well, I will tell you,

I think my family may may be the top,

purchaser from Audible because all 3 of my all 3 of my boys, my

husband and my 2 sons, like, we have the

annual subscription for Audible, and it might last us 2 months

Nice. By the rate that they read read audibles.

Personally, I personally am a big romance novel,

reader, which, I take I share openly.

No shame. And so for the romance readers out there, I will

tell you that the Penny Reid series, the the

beard series. So, Andy, I will tell you, you have quite a good beard.

It's a romance novel, and it's the beard series by Penny Reid. It's

absolutely wonderful, very funny, very sweet,

not suitable for this podcast if it's a family podcast because

it's a little steamy, but it is very good and very sweet. So

That's awesome. That's awesome. You can go to the data driven book dot com or

the data driven book dot com, depending how you wanna pronounce it. You'll get,

one free audio book on us. And, you know, and

if you subscribe and become a permanent annual, or monthly

subscriber, we'll get a little bit of kickback and, help

support the show. And the reason why this is actually funny. The reason

why we kind of are fairly strict not

strict, but we're we're sticking to our guns, so to speak on the

whole profanity thing is largely because obviously there's a professional

image, but largely because I like to listen

to some podcasts, and I can't do that when the kids are in the car.

So it kind of becomes this. It's more of a flexibility thing as opposed

to Totally. You know? Obviously,

I guess those those novels you probably wouldn't be listening to with the kids in

the car. You might those might be better for after the

kids go to bed and you're having Exactly. Time. You know?

I'm just saying, but that'll be fine.

Yeah. So where can folks find I'm sorry, Anne. This was your question. Go

ahead. No. I was just can't stop talking today. Where can

folks find out more about you and what you do? So the,

the easiest place is www.tuck point.com.

It's probably the easiest point part, place.

And then also on LinkedIn, I'm at, the at

jg Swanson. I assume you'll have both on your show notes and things like that.

Make sure we put that on the show notes. Yeah. Both of those places. So

either for the company or for me personally, those are the 2 easiest

places. Cool. Sounds good. Any parting thoughts?

No. But you guys are delightful. I just just spent this has been a nice

hour to spend with you. I just have loved it. So Well, thank you.

Thank you. We I really appreciate you

illuminating a lot of mysteries that I just assumed were just

part of just that was just the cost of doing business was dealing with these

kind of weird stuff or being in IT. Right? Being one of those weird people

in the basement thing. Like and and and now I kinda I have a lot

more therapy is a great analogy. I I you know, because it's like Yeah. I

know. You walk out of a good therapy section, you're like, that's why. Like, that's

what I feel right now. Yeah. Yeah. Good. It was really good. And I scored

a compliment on the beard. You know, that's always a win. It's a very good

beard. I really like it. I'm digging it. Thank you.

It was a great show, for us as well, and I can't wait

for our listeners to, to get a chance to see it. We just,

launched a new service earlier this week, in fact, where people can

subscribe and see videos. These videos behind the scenes,

they've been asking for that for, what, Frank? 7 years

since we started. And we wanted to do it. When

we started. We first started talking about it. We were like, this is this would

be great. And then we just found a platform and the stars

align, and we relaunched, like I said earlier this week. I don't think we

even have any subscribers yet. I I'm a little probably a little too

transparent in that, but we'll see. It's either

look. It's either this is the way we roll. I'll go and subscribe. I'll be

your first. Awesome. Woo hoo. That'd be kind. But it's you know, the

way we look at things a lot of the time is it's like it's an

experiment. You mentioned that earlier when you were talking to your clients. She's that you

do a lot of experiments and see how things roll. Well, if we get

one, awesome. If we get a 100, that'd be nice. You know? But

Yeah. We started the podcast, and we thought we were gonna do, I

don't know what, Frank, 10 episodes. And this is gonna be this is

gonna be around 375 or something like that. Yeah. 348, 3

3. Okay. So almost almost 360, basically. We're Yeah. We're gonna

we're gonna do a 360 retrospective for show 3 60. Sorry. I

spoiled the surprise everyone, but That's okay. It's a good tease.

It's a good tease. That's right. That's right.

Awesome. Cool. Well, thank you so much for having me, you guys. I really enjoyed

it. Thanks. It was great show, and we'll let Bailey finish the show. Awesome.

Thank you, Jennifer, for an excellent show. No longer

will I cringe when someone says digital transformation now that I understand

the true meaning on the term. We know you're busy and we

appreciate you listening to our podcast. But we have a

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this is Bailey signing off.