Lead the Room: Women in Sports, Outsider Advantage, and Real Leadership | Ep. 84 w/ Toni Will

Here's a leadership myth

that needs to be

legit checked into the boards.

If you don't already know the room,

you don't belong in it.

And that's some beautiful gatekeeping, I guess,

but it's absolutely terrible leadership

because the rooms most convinced

they know exactly what they're doing

are often actually the rooms most allergic to change,

and nothing exposes that faster

than a woman walking into a male-dominated industry.

And daring to lead

without asking for permission

from the ghosts of how it's always been done.

Today's guest is one of the only women in the country

leading a men's professional hockey team.

Now let's let that land for a second.

Not commenting on the room,

not adjacent to the room,

but actually leading the room.

And I think the most dangerous sentence in leadership

might not be "I don't know";

it might actually be

"We've always done it this way."

Welcome back to "Is Anything Real?",

the reality-first leadership show

where we test advice,

publish the receipts,

and ship what actually works under pressure.

I'm Adam W. Barney,

transition leadership coach,

author of "Make Your Own Glass Half Full",

and builder of Energy OS,

where I help leaders rebuild their operating system

when the tools that got them here stop working.

Today's guest is Toni Will,

women's leadership coach,

keynote speaker,

and general manager of the Kalamazoo Wings.

And that title matters.

Now, Tony is one of the only women

leading a men's professional hockey team in the country.

Under her leadership,

the Kalamazoo Wings have earned

two Guinness World Records in 2019 and 2024.

And she's spent more than 11 years in sports

after early chapters in banking and economic development,

which means she's also seen leadership

through wildly different rooms

where power doesn't always love being questions.

Toni, welcome to "Is Anything Real?"

Hey, Adam, what a great intro!

I need to bring you around to all my meetings.

I mean, I could have added

you're also the host of Women In,

that podcast.

You know, founded Empower Her,

an annual women's leadership conference

in Kalamazoo,

and also is an author of

Rebellious Success.

So.

But Tony, let's let's sort of start there.

When you entered men's pro hockey,

what did people assume you didn't know,

and what did they not realize you could see?

Well, it was interesting

because I didn't even stop to consider

what other people thought back then,

because I, one,

I was just so focused

on understanding the business side of hockey,

because as you pointed out in that beautiful intro.

The first half of my career

was spent in banking and economic development,

so this was a completely new path for me.

So, how I led

was saying right up front,

"I don'tknow what I'm doing,

but I'm going to figure it out."

And over the years,

I've caught some heat for that,

but I know what I'm doing now,

and that's what matters.

But I, one of my core values

is integrity and authenticity.

Two core values there that I listed,

and I wasn't going to be anything other than that.

So.

I didn't know what I was doing, and that's

how I've been since day one with the Kalamazoo Wings.

That's that's that's incredible actually, right?

And you know that that distinction is everything

because gatekeeping loves to disguise itself as expertise.

You know,

it says you don't understand how this works,

and sometimes that's true.

So you know, teach me,

but sometimes it really means

you don't already belong to our club,

our language,

our habits,

our assumptions,

or our comfort zone,

and those are really different things.

You know,

and you said in our first conversation

that you walked into pro hockey

asking, "What do you want me to do?

You know,

why do you want me to do, rather, this job?"

You openly talk about

those things that you just mentioned.

It's not weakness;

it's leadership in motion.

You know, nobody knows,

nobody knows until they learn.

Nobody has experience

until they're allowed to get it.

What did you have to learn fast there?

Yeah, I mean,

really, everything from the ground up.

What I did know when I walked in

with that 15 years of experience at that point,

I knew how to build a culture internally,

and I knew how to sell.

So I knew how to do those two things.

I knew how to teach sales and coach people.

So that's what I knew.

What I didn't know was just the basics of,

okay, how do you run a minor league hockey franchise

on the business side?

I loved my community too,

so those things I could take with me.

I had to go find people,

which wasn't hard,

doing the exact same thing I was doing,

and it wasn't hard

because I just started in our division in the ECHL,

which is the league the Kalamazoo Wings play in.

So I started, I went to the Cincinnati Cyclones,

the Indy Fuel,

the Brampton Beast

when they were still playing,

just to name a few,

and I went and met with

the Tonys of those teams to say,

"How do you make this happen

in your community?

And I just started to learn

because I'm a very curious person.

So curiosity got me in everywhere.

Yeah, yeah.

And quite frankly,

none of us know what we're doing

when we start anything.

So, like, anything,

like, I mean, life literally.

We don't know how to crawl.

We don't know how to feed ourselves.

I mean, we don't know how to do our first job.

We don't know.

So this notion that we're supposed to just know.

And only people

who know how to do things

should get hired is complete BS.

So, I dissolved that myth

and really just asked other people.

I love, I love that.

That's such a strong proof point, right?

I don't think

we should take I don't know yet

as a disqualification.

It's actually the cleanest starting point in the room.

Yeah, I want to push into this

a little bit

because it feels like

the heart of your story.

You know,

in our first conversation,

you described hockey as archaic.

It's very white,

not exactly overflowing with diversification.

You said actually,

being a different gender

and thinking differently,

and having a different perspective,

those things can be viewed as a weakness.

But the truth is that difference

can be the advantage.

Where did your outsider lens become useful?

Oh my gosh, I noticed,

It took me a minute to notice

that my gender made me unique.

I never thought as a white woman

in the Midwest

that I'd be the minority in anything.

But when you walk into hockey,

my race didn't make me a minority

because it is a very white sport.

It's 97% white male.

It was my gender

that made me in the minority.

And I've never felt that way before.

And it's hard.

But, I have a choice.

I could choose to be like,

"Woe is me, this is hard."

Or I can say

this is an advantage,

because being a woman,

I bring certain characteristics

to leadership that are different.

I can look at this through a different lens.

Right.

And then not having a hockey background

also lends itself to me,

as in, a leadership perspective.

And, I'll give an example.

Sure, please.

A lot of the men in this,

well, most of the men

are very emotionally attached

to what's happening on the ice.

They are hockey fans.

I'm not.

I'm not emotionally attached to any of that.

Now, do I recognize the importance?

Yes.

I'm emotionally attached

to the people in the organization,

to the people in the community,

to Kalamazoo.

And so that brings a different perspective

to how we run these minor league sports teams.

Because only 20% of the people

that walk through these doors

are hockey purists,

so the other 80%,

they're looking for entertainment,

and that is where my strength comes in.

Yeah,

Well, that's something, you know,

that the old systems rarely understand, right?

The outsider sees, you know,

they think the outsider, rather,

lacks context,

but sometimes the outsider

actually sees that context.

They see those patterns.

They see the customers differently.

You know,

what did hockey teach you

about the cost of sameness?

Let's say.

Oh boy, I mean,

I blew that cost of sameness right up.

I really did,

and I don't encourage people

to blow much up in their lives,

and only because I've experienced it,

but it costs a lot

because if you continue to market

the sameness of hockey,

you're gonna get the same fan,

or buyer,

in return.

But not everyone is, you know,

there's just not one demographic in Kalamazoo, Michigan,

you know, in my example,

so it's like,

well, let's look outside of this,

and really, you could start in-house.

You got a female GM,

but you have a black head coach

in Kalamazoo, Michigan.

So you put Joel and I together.

Yeah.

And we represent something really important,

not just for Kalamazoo,

but for the next generation of business

or sports leaders.

And so, we just take that small sample.

And we say, okay, well,

Kalamazoo is made up of something similar.

Yeah.

So let's go to where the people are

and talk about this stuff.

And that made a huge difference.

Wow, wow.

And that's, I mean,

that's that's the difference of when it,

you know,

when difference gets real,

when it stops being tolerated as just optics

and starts being trusted as intelligence there, right?

A hundred percent.

And now,

have Joel and I had to prove ourselves more

than, say, the white male?

Yeah, I would argue that hands down.

But we've done it through execution

and through our longevity with the organization

and our outside the box thinking,

and being willing to say

what the obvious is.

Yes, I'm a woman.

Yes, he's a black man.

And yes, we have different perspectives.

Now, are they always welcome?

Of course not.

But we still stand in what our truth is.

Yeah.

Yeah, yeah,

and that's absolutely beautiful

in the scheme of things, right?

And, you know,

I want to take this

and because I think it's incredible, right?

And talk about those Guinness World Records,

because I think they're fun

and also because they're not just fun.

You know,

under your leadership again,

the wings earned two Guinness World Records,

and to me,

records like that are not only about the record;

they're about what a leader makes possible.

What do those record-setting moments

teach you about leadership, though?

Oh my gosh.

Well, first off,

you hit the nail on the head.

Fun.

They are fun,

and fun is not just a frivolous three-letter word.

I write a lot about it, about fun,

in my book

because it is one of my leadership pillars.

There's a lot of science to back up

why fun in the workplace or just in life matters.

But we're in minor league pro hockey,

and I mentioned earlier,

80% of people come in

for the entertainment aspect.

So what's more entertaining

and a brand that brings the fun

than Guinness World Records?

And when you have a facility

that seats over 5,000 people,

this is a great opportunity.

So then we pair this.

Our first Guinness World Record

was the largest lightsaber battle

for Star Wars fans out there

back in 2019.

So you take the Star Wars brand,

you take the Guinness brand,

and then you take

the punchiness of Kalamazoo, Michigan,

where there's a ton of Star Wars fans,

and we sold that arena out.

That picture hangs in the front office.

It's just a beautiful visual

of what leadership and community is

when you bring it all together in hockey,

and it just showed

that we can have a lot of fun,

and even those hockey purists were like,

"This is pretty freaking cool."

So.

Behind the scenes, though,

setting a Guinness World Record

is no joke.

It, from a leader's perspective,

it takes an incredible amount

of discipline, organization,

and accountability

because there's

a whole team of people coming together

to meet the criteria of Guinness,

and these are not,

they just don't hand these distinctions out

like candy on Halloween.

You have to earn it.

So, it was exhausting.

Well, it's funny because you know,

that's the part that I love there

because leadership is often invisible

until something visible happens, right?

You know, the events, the records,

the launch, the win, the campaign,

that's what people see.

But underneath that,

is that culture.

It's the decision-making.

The belief,

the people who felt trusted enough

to bring ideas forward.

And also, the leader

who didn't need to be the center of every spotlight.

And then that ripple goes

way beyond the walls of the arena.

It tells people what kind of team this is,

what community it is they live in,

and what kind of leadership is possible.

What do you think those moments

signal to people watching you lead?

Because I love to think

about those ripples that we emanate,

you know,

that emanate from each of us in the world.

I've gotten some good feedback on that over the years,

you know,

because a lot of times

when you're in a position like mine

of general manager,

you're not getting

a lot of the love and accolades publicly

because people love to tell you

how to do your job,

even though they really don't know what your job is,

and publicly so.

But that's the world of professional sports.

So I just smile, and you know,

but, you know what it shows,

it goes back to that

creative, outside-the-box thinking.

It goes beyond

just what's happening on the ice.

It brings the community in

and I can't emphasize that part enough

because in hockey,

there's three tiers of hockey.

There's the National Hockey League,

which is the NHL.

Then there's the American Hockey League,

which is the AHL.

And then there's the ECHL,

which is the league the K-Wings are in.

Our players move up and down that system.

And so, when you get to the higher level.

And even any level, for that matter,

these teams are in communities

that are way bigger than Kalamazoo,

like a million, like a population of a million or more.

Kalamazoo, 75,000 proper is our population.

So, community,

we have less people to sell to.

It's more work to get people in the door.

So, going back

to the Guinness World Records

or Rainbow Ice,

which I know hasn't been mentioned,

or Green Ice,

or just some of the other things that we do.

It's bringing community in

so they can get a feel

for what professional hockey is.

Because, if you're born and raised here like me,

you're taking this for granted

because you think every community,

because we've been here for 52 years.

It's not like that, it's super special.

That's incredible,

and that's where that legacy gets real

when what you build

gives other people more permission

to believe they can build too, right?

You know, and in that realm,

one of the reasons we connected fast

is that we both care so much

about underdogs and access.

You know, and I remember saying to you,

as a white guy in the world,

I've had, you know,

confidence and access handed to me

just by systems

that don't hand it equally to everyone else.

And that doesn't mean I didn't work hard,

but it means I don't get to pretend

the starting line was equal.

You lit up around that, I think,

because your work, also,

is about helping people

step into rooms

where the rules aren't written for them.

How do you think about access there?

Yeah, and I did light up to that

because most people don't want to

talk about this stuff.

Especially, and I say this with love,

because I have all kinds of white men in my life,

including my husband,

my son, my dad.

Right.

But, it is a different start line.

And then when we call out the obvious,

I think it just shows the humility that we have,

and that our activism comes from a place

of really being authentic and genuine,

and, maybe for me, a little naive,

and I don't think that's a bad thing.

But I think, to answer your question,

of what I believe,

if I were going,

cause you get me going on this, Adam, but,

is you know it.

Well, ask me the question again

because I got going.

Well, just how do you think

about access, at a baseline?

Yeah, exactly, we have access.

So how do we bring that access

to other cultures,

religions, gender, sexual orientation,

all of that?

How do we,

who our start line is at a different spot,

be able to bring that same start line

to others who are not us.

And so, that's my mission.

And the biggest part of this,

or one of my many missions,

the biggest part of this

is just saying it out loud.

Like, two people like you and I

just saying it out loud

because we're not ignoring it.

We're going headfirst into it

and doing something about it on a public platform.

Yeah.

And I look at that almost as a door handle test,

right, Toni?

When you get access,

do you use that as a trophy for yourself,

or a medal around your neck,

or use it as a door handle for someone else?

Because the work isn't only

becoming the exception, right?

You know,

I don't want women actually in sports leadership

to have to be a once-in-a-generation,

undeniable to get,

basic opportunity.

You know,

I also don't want underdogs

to feel like they need a perfect resume,

they need perfect timing, tone,

or perfect everything.

I just want better rooms.

What does a better room look like to you?

Yeah,

you say door handles

and I'm all about elevators.

You know,

you open the elevator

and bring anyone in there

who wants to do this work

to go up with you.

So those rooms, it's really about,

okay,

how can we get a seat at the table?

What rooms do we want to be in

as women in sports in particular?

It doesn't have to be

the board of governors room,

or even a layer up the executive committee room,

which I've broken through both of those barriers,

but it doesn't start there.

It starts,

what rooms do you want to be in?

So, when I stepped into this, well,

when I started to take the blinders off

as I was getting past

the first few years of this,

I'm like, wait a minute,

there's no room in our league,

a proverbial room for just women.

So I'm going to start that.

Because if I'm going to talk about this stuff,

I want to do something about it.

I can't just say,

"Oh, here's the problem.

Someone else go find the solution."

No,

I will help find the solution.

It's not about Toni Will.

It's about everyone else.

So I created this space,

and this is my definition

of servant leadership.

I don't want to get paid.

I don't, you know,

I create a committee.

I help mentor these women,

and then I'll bring speakers in,

and we do all these things together

to help facilitate change,

so they can get

in these rooms they want to be in,

and that first room starts with

the ECHL Women's Sports Network.

Yeah, and I mean,

that's a proof point there

where allyship gets real

when access becomes architecture

and not simply charity, right?

Exactly.

Toni, I want to move this

into one move our listeners can run this week,

and I want to call this one

The Outsider Advantage Audit,

and I think it's for leaders, founders.

sports executives,

or people who want to enter that room,

women in rooms

that still confuse sameness with credibility,

and men who want to be useful allies

instead of just motivational furniture.

And it's four simple questions.

The first being,

what am I treating I don't know yet

like weakness instead of learning?

The second is,

whose difference in the room

am I minimizing

instead of mining for intelligence?

The third being,

what rule am I following

that was not built for the leader I'm becoming,

And the final one,

where can I turn access into architecture?

Toni, what might you add to that list

or amend on those questions there,

for someone who just wants to start today?

I would encourage, on that list.

to when you look at that.

I love this audit, by the way.

Who's one person

that can help me get to where I want to be,

and it could fall into any one of those

because there's always someone walking the similar path,

and they can help become allies

in this on similar missions.

I love that.

That's simple,

and that's where leadership gets real

when the outsider stops apologizing

for seeing what the insiders actually normalize, right?

So.

Tony, I think you know how we end here.

After all of this,

but especially that myth

that not knowing means you don't belong,

is anything real?

Is anything real?

That's a great question.

Yeah, I do think we make it real.

Those of us who are executing

and who are listening to this,

they want to make it real.

So yeah, it can be real

if we make it that way.

We don't wait to be invited.

We create the space.

I love that.

I love that.

What you know, what feels real to me

is the outsider advantage, actually, right?

But then the courage

to enter a room that wasn't built for you,

and the humility to say,

"I don't know yet."

Maybe even that discipline to learn

and that nerve to challenge

what insiders call normal,

and then that generosity to make the next room

easier for someone else to enter.

Absolutely, and that's what it is.

Just making it a little easier

for the next person

to walk through those doors.

I love it.

Toni,

where can folks find you,

Women In...,

Rebellious Success,

Empower Her,

and your beloved Kalamazoo Wings?

The K wings can be found at

Kwings.com

and then everything else you mentioned,

the book, my coaching, podcast,

all the things, ToniWill.com,

T-O-N-I-W-I-L-L.com.

Beautiful,

and we'll of course link to that

in the show notes below,

but, you know,

I would say Toni and I are saying today,

you know,

for our listeners,

stop confusing familiarity with competence.

The person that's always been in the room

shouldn't automatically be treated

as the smartest person in it,

and the outsider

is not automatically the risk there either.

Sometimes I think that risk

is actually the rooms that are so addicted to themselves

that can't recognize the future when she walks in.

You know, so this week.

Say I don't know where it matters.

Ask the better question.

Trust the different voice.

Stop treating women, underdogs, and outsiders

like they need to prove 10 times more

just to be heard once.

And if this hits,

send it to a leader, coach,

sports executive, founder,

woman trying to break into a room,

or a man with enough power

to make that room less ridiculous.

And if you're navigating a leadership transition,

there's also a 20-minute foundational call link

in the show notes with me.

No pitch, no pressure there.

But Toni, thank you for the grace,

your own patience, your leadership,

and the reminder that not knowing was never the weakness.

The weakness is actually having those rooms

being built too small

for different kinds of knowing.

Thank you, Adam.

It's been a pleasure.

Great work.

Awesome.

Thank you.

Well, until next time,

stay grounded,

stay human,

and keep questioning the noise.

Creators and Guests

Adam W. Barney
Host
Adam W. Barney
Adam W. Barney helps transitioning leaders navigate career and leadership inflection points with clarity and momentum. Author of Make Your Own Glass Half Full and creator of EnergyOS. Based in Boston, fueled by family and music.
Lead the Room: Women in Sports, Outsider Advantage, and Real Leadership | Ep. 84 w/ Toni Will
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