Parallel Entrepreneur with Mark Cleveland

The leadership playbooks that built today’s successful organizations were designed for a different world.

In this episode of The Parallel Entrepreneur – Innovation Series, hosts Mark Cleveland and Johnny Anderson sit down with Amalia Goodwin, Global Managing Director of Adaptive Organizations at Slalom, to confront a reality most executives quietly avoid:

Incremental change is no longer safe. It’s organizational suicide.

Amalia works with C-suite leaders and boards who understand that AI transformation isn’t about tools, it’s about redesigning how organizations sense, decide, and evolve at scale. This conversation goes far beyond technology and into the deeper work of leadership courage, organizational design, and the role companies play as architects of society’s future.

We explore what it actually means to build an adaptive organization, one capable of continuous reinvention rather than reactive survival.

In this episode, we discuss:
- Why AI transformation fails without leadership courage
- The danger of applying yesterday’s playbooks to tomorrow’s problems
- What “innovation metabolism” really means inside organizations
- How leaders can balance quarterly performance with long-term survival
- Why organizations must see themselves as civic architects, not just profit engines
- Designing decision-making systems that can keep pace with exponential change
- The overlooked societal impact of AI governance and organizational choices

Amalia brings insights shaped by 25+ years and 100+ global transformations, blending strategic clarity with moral responsibility. This is a conversation for leaders who know the future isn’t something you react to, it’s something you design.

Chapters:
 00:00:00 “Courage feels a lot like fear when you’re in it.” (Cold open)
 00:00:47 Episode introduction + why this conversation matters
 00:01:07 The systems that made you successful won’t survive the AI age
 00:01:16 Why incremental change is actually dangerous right now
 00:01:37 Amalia on helping organizations succeed in a technology shift
 00:03:54 “The definition of value is changing.”
 00:04:22 How companies are evaluating AI strategy (M&A lens)
 00:05:23 Adaptive leadership + reinvesting in continuous change
 00:06:00 Learning velocity as a new measure of value
 00:06:25 Decision velocity: when do leaders know enough to move?
 00:07:27 “Innovation metabolism” — how leaders fuel themselves differently
 00:07:56 Addressing fear in strategic decision-making
 00:08:13 It’s okay to be afraid — making AI adoption fun (Bingo + games)
 00:09:59 The moment AI “blew me away” (and rewrote an SOW)
 00:10:29 The real leader work: humility, new mindsets, new skill sets
 00:10:41 “Courage feels a lot like fear when you’re in it.” (Expanded)
 00:11:28 Relearn vs. Unlearn — why unlearning is harder
 00:12:23 Six-month roadmaps vs. 3-year plans
 00:13:19 Massive 30-year transformative vision
 00:14:01 AI as a playground — bringing back play
 00:15:03 Hackathons, bake-offs, and low-code teams winning
 00:16:00 Agentic workflows + giving unexpected leaders a stage
 00:16:55 Closing: “A bake-off sounds like the right answer.”

About the Guest
Amalia Goodwin is the Global Managing Director of Adaptive Organizations at Slalom, where she partners with C-suite leaders and boards to reimagine how organizations lead through exponential disruption.

Her work focuses on the intersection of AI transformation, leadership courage, and organizational responsibility, helping companies design systems capable of continuous reinvention. Amalia is a recognized thought leader on adaptive strategy and organizational courage, with insights featured in Fortune, Forbes, HR.com, Unite.AI, and Slalom’s global research on AI-enabled organizations.

She is known for introducing leaders to what she calls “innovation metabolism”, the capacity to transform fast enough to survive, without being consumed by change itself.

🔗 Connect with Amalia on LinkedIn:
https://www.linkedin.com/in/amaliagoodwin/

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

What is Parallel Entrepreneur with Mark Cleveland?

Mark explores the minds of visionary entrepreneurs who refuse to limit themselves to a single venture to learn how these trailblazers manage risks, innovate across industries, and turn ideas into impact.

Whether you’re scaling your first business or juggling several, this podcast is your ultimate guide to thriving as a parallel entrepreneur.

There's a whole leader session

and set of work that we have to do

and build new skill sets and mindsets

and one of those is having the humility to know

this is scary,

and we're gonna work through this together

and being able to say that as a leader.

I think courage feels a lot like fear when you're in it.

Yes, yes!

This conversation isn't comfortable

and that's the whole point.

Amalia Goodwin is the global

managing director of adaptive organizations

at Slalom and she works with executives

who already know something

most leaders avoid admitting.

The systems that made them successful

won't survive the AI age.

In this episode we dive deep into two ideas

that challenge the status quo: 1

why incremental change is actually dangerous right now.

and 2

what it means to lead organizations that can sense

decide and evolve fast enough to stay relevant.

If you're leading through uncertainty

and everyone is this conversation offers a few nuggets

you'll appreciate so let's dive right in.

So I'm all about helping organizations be successful

and this technology I think

levels the playing

playing field in so many different levels.

So it's so much fun.

That's awesome you're Portland

Oregon right?

I do live in in the West Coast,

I have had you know

ventured out living in North Carolina and other spots

so

I do love when I get to come play in the south as well.

Well I'm from Eugene, Oregon

so. You are. And I lived in Portland for 10 years

and I've got to say welcome to the south.

I appreciate that. Go Ducks!

Go Ducks! Go Ducks!

Yeah I'm, I was born and raised in Idaho.

And really I've spent most of my life in the northwest

in Oregon and Washington, Seattle and Portland,

but I always love coming back down to Nashville

into the triangle. That's probably you know

I sort of think about like the third act of my life

and what's that gonna look like?

And it and like this keeps calling me back

so We'll see. Well

come on down, come on down,

Actuall, no.

We're full thank you.

You're full. Yeah

like I say this and when I I will talk to folks and

when I go back to Idaho like

but hey I like I did my undergrad here

I did my high school here

I was born and raised you have to accept me back.

Even though I left for a minute.

So what is it? What's.

We're

On behalf of the Greater National Technology Council,

I'll ask the question, what is it?

What do we have here in Nashville.

You know what you have is, you have an interesting

I guess the

like spark is the first word that comes to my brain.

You have a energy, that is around people and culture

but is friendly to business and innovation.

And being able to bring that secret sauce all together

and have fun with it. I believe creates community right.

So

when your businesses are thinking about your community

and when your education systems. And what we

you know what I got

meet some amazing people that are

really trying to think through

how do we think about education very differently?

Because we should. I don't see that I.

I get the privilege of going to many different

cities and around the around the country

I don't see this everywhere.

So it is pretty special what you've created

and the excitement that the businesses have around okay

how do we do this how do we think about this

how do we involve the community.

Inclusive of the education system,

that just doesn't exist. So I've been like everybody

sort of addicted to this conversation about AI.

And I'm gonna tackle it from a different angle.

I think the definition of value

is changing. What is value?

What do you think is changing?

Well

I was in a conversation with a client this week and I

I do M&A work and yeah and I

and everybody is looking does

does the guy who's gonna buy you

have a better strategy than you

and are you moving in that direction.

And everybody's evaluating AI strategies specifically.

But the companies themselves often seem to wonder,

let's say for example;

if we could just get this project done in six hours

that used to take us 60 do we value

do we pass that value on to the customer?

Do we pull that value inside?

What is the value of the service we delivered

if we now know it can be done in six hours.

Yep. And all of our perspectives are defined by 60.

And these are 10 x changes in everybody's life.

Internal and external perspectives

so there's a war

I think going on about the definition of value.

I'm curious how you see that playing out?

I think that's a really great

and a good perspective to have.

What occurs to me about value is

when you save that time.

I think a couple things are happening

one is there's people are like

you often hear "it didn't work"

I'm like yeah

you got savings you got leakage.

Cause you haven't

redefined what you want people to be doing.

And I think value starts to like.

I think the organizations that will succeed is going.

The value is gonna be

how do they continue to reinvent themselves.

So we call it like how are you like continuously

like being an adaptive or an adaptive leader.

But it is reinvesting in the continuous

change that this technology is bringing.

But I also do think

how an organization measures itself

like there will always be the tried and true things

that you're looking at from an M&A standpoint

and from a business standpoint

for sure.

But I do think it starts to shift

and so you are going to start like.

What I'm valuing and what I want out of the teams

like I get the fortune to work with and manage are

what is your learning velocity?

Like how fast are we learning and pivoting

so that we can help our customers differently?

And learning velocity isn't training courses

it's behavior changes. How

how are we thinking about in an innovation cycle

and an innovation metabolism

where we take ideas to

how fast can we pivot those ideas to actual revenue.

Like that is a different

value that we need to start thinking about.

And how do we think about the

the decision velocity that leaders have?

Like that is of a different value that.

And what will stop and slow down organizations is

wanting to be sure and that is really hard.

Like it from a leader standpoint

wanting to know all the answers before you move forward.

And knowing

when do we know enough to start testing and playing.

And in a way that's like often and you hear Amazon

talking about a two way door

so when is it where we can still play

and it's not cutting us off

and

and where do we need to really slow down and go slow?

We are

we're treating everything like as a slowdown.

So I think valuing and decision velocity.

So I think there's a whole and then like

what is the overall experience

we're creating for our customers

and our people?

That will be of a different value as well.

Like I think it all does start to shift

and it becomes more than revenue,

revenue is always gonna be a a judging stone.

But I think your ability to create new revenue

because all of our expectations change

is gonna have to shift

cause you're thinking about it very differently.

I love this the term innovation metabolism

and when I think about metabolism

you know you can feed your body energy

and then not work out and get no

no muscle from it or you could

fast and and have completely different life experience

just by changing the nature of how you feed.

How you fuel yourself. So AI

is changing the nature of how leaders fuel themselves

how they make decisions how the people respond to it.

How are you stamping the fear out

cause I think fear is the root of why

people want to be sure of something

cause yeah they're afraid of something.

How are you stamping fear

out of strategic decision making

and an innovation metabolism?

Yeah. Yeah

like it's

fun.

I think it's okay to be afraid

I think part of this is there's gotta be leader

a lot of leader work that is happening right

so working with your C-Suite

and your leaders

and your executives throughout the organization.

And part of this is

we have gotten here

like I've spent almost 30 years in my career

and I've gotten to this point because like

I've Learned something and I know how to reapply it.

And now we all have to learn something brand new

and maybe all of our experience

doesn't have the same value as it once did

and my value is now relearning

and helping

people know that I can help them get through this

because we're all scared.

It's okay for humans to be scared

in the fear that exists

like it's helped us evolutionarily

we need it and

but it is okay to like

we need to acknowledge that and go okay

this is a little scary let's try.

Like let's have fun trying!

So I think the biggest thing that we've done

is make it fun.

And so we've done things like creating Blackout Bingo

to learn the new skills

to create it as like using AI in your day to day work

and Blackout Bingo for teams and departments

and like it's true

we created Tic Tac Toe for executives

made it a little easier and to

to have like you know

our our C-Suite

come in and start playing with this technology

in a different way.

But having fun with it acknowledging it yeah

it's a little scary. The first time I had it like

and I like my experience with this has been

I was lucky enough with Slalom

in our innovation lab

to be playing with the 2.0 model

so I saw it with some um early avatars

I'm like okay

that's neat and it's clunky

and a lot of the innovation teams would come through

and like they were seeing value.

And I was like that that makes sense

I'm like no Amalia

you need to be paying attention.

And I smiled at him like yeah

I got I got an org design I gotta do that's neat.

And

then three out of like six months later happened

I was like and tell and then that blew me away.

I was like oh

it just made an SOW for me.

I often tell the story I'm like

and it was maybe better than what I would do.

And and there's that feeling of oh

then what do I do but if I'm honest with myself

I don't like doing that work

I like doing the like working with the leader work

I like doing

like connecting with the teams and helping them.

So and that is not necessarily something

a GPT is going to do for you

or an agent is going to do for you.

And so

I do think there is something around acknowledging it

like

there is a whole leader, there's a whole leader session

and set of work that we have to do

and build new skill sets and mindsets.

And one of those is having the humility to know

this is scary

and we're gonna work through this together

and being able to say that as a leader.

I think courage feels a lot like fear when you're in it.

Yes! Yes!

And like it's okay to feel fear and you keep going.

Yeah. And that's like what happened to me

I was like oh

I can either be bored in my career for another 10 years

and be done

or I'm gonna jump into this and change it all

and be really scared and have some fun

and that's the only thing I know to do.

I've always.

I've always heard courage isn't the absence of fear

it's the presence of

or it's action in the presence of fear. Still no

it's there and you still move forward

it's kind of like the bison you go into the storm right.

Well you

you use some some really interesting terms and you

you mention the term relearn

I'll full disclosure

I heard you speak yesterday in present

and I was fascinated by this

this slight change

by changing two letters and use the term unlearn.

Relearns a function.

I get it unlearns a little more complicated

so tell me a little bit more about that? Yeah

unlearns hard and this is

I believe that

and one of the things I often will say is it's leaders

it's us

that's gonna get our own way with this technology.

And leader like

and part of that is we got here knowing some things

right and we were good at what we do. And

so how do I stop and go okay

what has served me in the past

is not gonna help me in the future

so how do I stop this current behavior?

And as a leader some of that is thinking

you know what's next and when

like we if we really are honest

2027 is pretty hard to predict

from a technology standpoint.

And what's gonna really be there

so how do I um

really stop and challenge what I think I know

and really start thinking of

and like a very tactical thing.

I do with leaders is

you need to think in six months increments

in six months

you can take what like GPT5 just came out

Microsoft got something coming in two months

two weeks

I think ish like they will all have something in like

you know

about the same period of time where you can make

alright what's my BHAG for the next six months

and you should

start thinking about this in six month increments

not to the two to three years.

And so that is like an unlearned behavior of like

everything I think I know I do in this time period

and I'm gonna we're gonna get to this roadmap

that's two to three years like hmm

getting your team to a spot where you can do that

in six months is a very different thing

it's a very different thing.

So how do you like things you know to be true

and everything you do

like how do you ask the question and stop and go

is that true is the strategy really to your roadmap

or is it a six month roadmap against a very large

30 year massive transformative vision.

It like feels like science fiction

but you'll probably get there

because of this technology.

A massive 30 year transformative vision.

You can string some words together.

Do you like it? Get me jacked up,

pumped up! Yes!

It's so much fun, how much fun is this

yeah right? Yeah.

I you mentioned earlier games

putting games together or yeah

you've used the word play.

And I've

I recently thought about you know

when kids get together

they're playing there is no rule set.

Then we eventually teach them the rules of the game

which sort of like wreck the play part.

And now it's a contest and a game

and then later on you know

nobody want games are no fun right.

So we've we sort of pressed the fun out of play.

Yes. And wouldn't it be great,

if we looked at this as a big playground?

Yes. For the creative expression of whatever

we haven't figured out yet.

So what's the most exciting

thing that you have seen people do

that is playground oriented?

You know. It sounds like we need to unlearn some things.

Yeah like there is an unlearning thing

I think one of the thing like I've got an.

Something that a team is working on right now to

to that answer one of the things I think is really true

what you just said there is really profound is

and there is something really

interesting to watch out of kids and like

their excitement for learning.

And one thing that something happens in

happened in my educational system around learning rote

information that we no longer necessarily need to know

we need to learn how to learn.

And so like

if we can help kids and help like

and adults really think through

really what we do now is learn how to learn.

And use this technology to help us learn

and like you know

you do our critical thinking and that sort of thing.

And you can have fun with that too

like and have a playground with it.

We have a team doing bake offs like

we always do kind of a

we've always done fun hackathons

where you gather a team together and

you present ideas. What was really fun about

this last year's hackathon within our organization

we had we had a business team with no

and low code team win the hackathon.

That was a technology hackathon because I mean

and I think that shows something very interesting

around. These were business consultants

these weren't like the tech teams.

So there

I think

there's something also happening in organizations

where we've done this bottom ups use case view

and we said OK

tech go build this for us.

And I'm like half of those use cases

I think

we could teach low and no code skills to the business

and they can self serve. And our experts in technology

should be doing the bigger harder

more complex things.

So there's a different way to think about that.

And so in that the

so we've done definitely done the bake offs

I think we're going to do another bake off

around agentic flow right now where

we'll have our senior execs do

and we've done this with clients as well

where they come in and they get to be the judges.

And so we give people a period of time

and it could be two or three days where like

they war room it and they create from like

vision through pretty much Figma

workable code to something pretty amazing

and you can get that done in two to three days.

And like do like

what's the concept that we like

that we wanna do and play with

and take to the next level.

Many clients do fun things like that as well

and you can have fun with it when you're doing that

and you're then allowing people that maybe were like

I'm not sure about this AI thing

and they're now presenting to your C-Suite

or they're presenting to their CEO

or their COO or whoever's in that organization

that

they probably would have never had that opportunity to

of like what they just built in two days is like you

you have people that will follow that forever.

A bake off sounds like the right answer.

I love it. Let's play

I love it. Thanks for joining us today.

Yes thank you.

Welcome to Nashville. Go Ducks!

Go Ducks! Thank you, so much!

Had a blast