People First! with Morag Barrett

Welcome to this week's

episode of People First.

And my guest this week is

Jonathan Bennett.

Jonathan is an advisor and

executive coach for

purpose-driven leaders who

need help solving their

organization's toughest obstacles.

With experience in urban, rural,

remote and First Nation communities,

Jonathan's expertise is in social purpose,

business strategy, governance, branding,

change and communications.

His coaching draws on twenty

five years of creativity and leadership,

success as a CEO,

board member and founder.

He is known for his deep

listening and his

breakthrough solutions that

create insights and new strategies.

Jonathan, welcome to People First.

Thanks so much for having me, Maureen.

Okay, well,

I'm looking forward to the conversation.

And for those of you who are

watching and listening, listen deeply,

channel your inner Jonathan Bennett,

because you are going to

hear dueling accents at

play here and recognize the

differences and the

similarities from both of us.

But to soften us into that

and help people just to get

a feel for where we are,

my opening question, Jonathan,

each time is, so when you were a wee lad,

What did you want to be when you grew up?

Yeah, so when I was a wee lad,

I was in board shorts

running around the surf and

beaches of Sydney, Australia.

And while I was mad into sports,

deep down the thing that I

most knew I wanted to do

was tell stories and to become a writer.

And that's really eventually

what I ended up doing.

I went on and

uh, got an English degree and, uh,

started to write, scribble, you know,

all those sorts of things.

Um, and went on to publish, uh,

seven books, poetry, novels, uh,

short stories, and, uh,

had a really nice literary career.

And it was, uh, it was really great, but,

um, you know,

I suppose this is where it

comes down to it.

Like, uh, like crime doesn't pay.

So, uh,

I had some choices to make

as I kind of ended my thirties, which was,

this is all well and good,

but probably need to be a

grownup at some point,

probably need to make a living.

And I ended up moving into

kind of corporate communications,

public affairs,

eventually into general management.

And that led me to kind of

where I am sort of today

over a long period of time.

But that's how it all began,

was as a storyteller.

Storyteller.

I love it.

I love the fact that you

actually realised that childhood dream.

And then there's a bit of me that goes,

poetry, go on then,

read one to me or recite one to me.

So, I mean, a bit of a spotlight round.

You don't have them memorised.

But there you go.

Wow.

But seven books.

So as much as you say that like crime,

it doesn't pay.

obviously successful because

having written three books,

I know the effort that goes into that.

So seven.

And so you've pivoted then

from writing for your own

pleasure and your reader's

pleasure to then corporate communications,

et cetera.

So tell me,

how was that for you in making

that shift?

You know, in hindsight,

it looks organic and

thoughtful and intentional.

As I experienced it,

it was like a mad dash from

one thing to the next.

I was definitely somebody

who just began by saying

yes and I'll figure it out.

What I learned about myself

is that I'm good at making

decisions and I'm good at

helping other people make decisions.

And so I quickly found

myself as a head of

communications for

increasingly more complex organizations.

And I was a proximal to CEOs

and senior leaders and

boards when I was pretty, pretty young.

And so that exposure allowed

me to be sort of in the

room when hard things were happening.

And I was able to weigh in

on pieces along the way and

eventually to become

people's trusted advisor

and head of comms to be

able to support them with their thinking.

So I think that's what I

kind of learned when I made the switch.

So I was kind of in my early forties.

I was on the C-suite of a

large regional hospital

here in Canada where I live.

And I'd been, we built a new hospital.

I made it through two CEOs.

Seven years later, I was still standing,

but I was really burned out.

And I thought it was time for a change.

And I thought,

how hard could this consulting thing be?

I mean, really?

So I quit and hung out a

shingle and started a consulting company.

And that's what I did for

the next ten years is I

grew a management consulting company.

And that's where I learned

what it was like to

actually be on the net.

to actually make decisions

and be the person that was

actually responsible for

driving business and

delivering on the work as

opposed to just being next

to the person who was doing it.

So that was also an important life lesson.

So in answer to your

rhetorical question in that,

where you talked about all

how hard can it be, on reflection,

how hard is it to be an

entrepreneur and to start your own firm?

It's pretty hard.

pretty hard um I thought it

was thrilling and exciting

um I mean you know we

started with just may

classic uh started winning

too much work drew a few

you know colleagues around

a few networked people

realized this made no sense

financially I should just

hire them next thing I know

I've got a few employees

next thing I know we're

growing um you know over

the course of ten years we

became a b corp uh and I

sold the company three

years ago to one of my

colleagues so it was a management buyout

And, you know,

we had thirteen full time staff.

So as a professional services firm,

we got to a decent size and

we did some really amazing work.

And the company continues on

to this day and shifting

and growing and changing

and it feels great.

But it was lumpy up and down.

I learned all the hard things,

all the hard ways.

And I feel grateful these

days as a coach and an

advisor to be able to

support other people

because I've been there.

And I made some really juicy

mistakes and learned some lessons.

And other things, they weren't mistakes.

They just learned them too slowly.

And so, I mean,

the call that I had before this one today,

I was helping an

entrepreneur just do

something that I'd learned

the hard way over a long period of time.

But for her to do it like at

the start and quickly when

it would be easier to build.

And so they're the sorts of

things that I love now is

they get to trade in on.

you know,

the hard-learned knowledge along the way.

I listened to that just

short snippet of the ten

years with your original firm,

and I can just relate along

the way the lumpiness, the hardest,

I think, that I've ever worked.

A corporate role felt easy by comparison.

And also juicy.

I love that adjective.

The juicy mistakes that I

still make even after

seventeen years now with Sky Team.

And I think one of the biggest challenges,

as I reflect,

certainly for the last few years,

my team will attest to this.

I've carried a cloud.

Actually, this time of now, this fall,

I'm through the cloud.

The cloud has parted and the

sun is back out.

But I felt like I was carrying a weight.

It was heavy.

And so with the coaches,

your own experience,

but also the leaders that

you're coaching right now,

What are you hearing that is

challenging them?

Is it that, similar to mine, my experience,

that isolation of the, well,

I've just got to walk it off,

nothing to see here, just work harder.

Who can I turn to?

What are the challenges

you're helping them to

solve and overcome?

Well, they feel like, and it's often real,

is that they're on the nuts.

It really is them.

They've created this machine.

They have to feed it.

uh and everything is on them

the accountability is deep

and they made promises

across this table uh and um

it's deep they don't want

to let people down that

they realize like if they

don't win enough work or

they don't have enough

business uh that they'll

have to downsize or they'll

have to lay people off and

that's heartbreaking no one

wants that and so that's

what keeps them up at three

in the morning is just

keeping this thing going

and whether they like it or not um

You can debate whether or not,

there's lots of men that

don't like the word lonely.

I've learned that.

So you could describe what

the feeling is of being

kind of quote unquote lonely at the top.

A better word that I've felt

that lands is it's isolating.

And that's because you're by yourself.

There's only so much that

you can tell your board of

directors or your investors

without worrying them.

There's only so much that

you can tell your staff and

your team without scaring

the proverbial out of them.

There's only so much you can

bring home to your spouse

because that's just boring work stuff.

And so what do you do?

You keep it to yourself.

And you keep it to yourself

and you keep it to yourself

and you bottle it up and

you put the lid on and you

re-put the lid on tighter and tighter.

And then at some point,

you're not doing great.

You're not doing well.

There's one too many things.

And that can be when things

don't go well and when

you're not at your best.

And or it can be when you

think to yourself,

maybe it doesn't need to be this hard.

Maybe I could get some help.

And that's when people like

me are able to show up and

just walk a journey with a leader,

be able to just hold the space,

ask hard questions,

be the only person to just listen.

I'm not invested in your

success other than I care

about my clients.

So I don't like have any

financial stake in their success.

So I can just be that person

to just catch the hard

stuff and say what I think

I'm hearing and where I've

seen it work before and

help them untangle

They're thinking.

And sometimes they'll talk

themselves just through it themselves.

They just, you know, like at the end,

they'll just talk for an

hour and they'll be like, oh,

I feel so much better.

And I'm like, yeah,

I literally said nothing.

And again, it's having this safe space.

And you described yourself

as a trusted confidant earlier on.

And my guess is from the

research that we're doing

here at Sky Team and the

articles that I'm reading,

when they talk about loneliness,

when they talk about

isolation or disconnection,

often the focus is on the

more entry level within the

organization or those

middle tier of leaders.

And from what I'm seeing and

hearing from my executive

coaching clients is that

the illusion that it's okay at the top

is just that.

If anything,

that data is underreported in

terms of that feeling of

having to keep yourself at

an arm's length or consistently filtering,

how am I showing up?

Am I smiling today?

What am I saying?

What impact ripple does that create?

And that's the power of

that we bring as executive coaches,

as those trusted confidants

in being that safe space

where they can show up more

authentically and share

what's on their minds and

either sort it through on

their own by talking to

think or leveraging your experience,

et cetera.

So what's your advice then

for a leader who may be

listening to this

conversation who suddenly goes, huh,

isolated.

Yes.

Lonely.

No,

I've got mates to go down the pub with.

I've got family to hang out with.

I don't feel lonely,

but I do feel isolated.

What's the first step for them?

Well, I mean,

I suppose the first step is

to just do a check-in with yourself.

How are you doing?

Are you noticing that you're

dysregulated in meetings?

Are you doing your best work?

You know what good looks like for you.

Are you in a good period?

Maybe you're killing it.

Maybe you're in control and

the other things in your

life aren't crowding out

your ability to personally

think through your stuff.

Maybe you have a business

partner or your executive

team is very open and super

honest and genuine and

you've created enough trust

and psychological safety

and all the good things that, in fact,

you've got everything you need.

And that's great.

For a lot of folks, though,

those ingredients aren't

all there at the right time.

And there's sort of two

things that happen.

One is that people feel like

they need to fake it and

look like they've got it all together.

And then the other part is

that folks are kind of not

plugged into themselves,

like they're faking it to themselves.

They think they're okay,

but they're actually not doing okay.

And they're not paying a lot

of attention to how they're showing up.

And so that's when a spouse,

a dear friend will look at

you and smile and say,

but how are you doing actually?

And when people start doing that for you,

that's a signal that maybe

some additional support might be helpful.

I describe it a lot of the

time when I'm starting to

work with somebody is like

the first couple sessions

that I spend with somebody,

it's just plot and characters.

They're telling me the story

of the company and all of the people,

the board members and the

names and what they did

wrong and the VP and why

it's so dumb and the

clients and why they do and

they didn't pay on time and

whatever's going on.

And at some point,

the plot and the characters

settle down and together we

figure out what's really going on here.

Do we have a leadership issue?

Do we have a business model,

an underlying business model problem?

Do we have external forces

that are changing and

reshaping this business?

Like what is actually going on?

Because rarely the presenting problem

and what people think is

wrong or is going on for

them is actually what is

really there and it can

take some time and a bit of

patience as you kind of

untangle the plot and the

characters for me and

usually my client together

to kind of co-figure out

what is really going on and

then from there what do we

do about it what changes

what interventions can we

make to make things better

or to reset this course and

sometimes there's big life

decisions we're at a t

intersection and a big

choice needs to get made

other times it's just small

degrees of difference and

we just need a plan we just

needed to articulate where

we're at and where we're

going and we just need to

you know move things a

little so it's different

for everybody and I like

just trying to meet my

clients uh like as a

trusted advisor I just try

to like meet them wherever they're at

and go.

And sometimes it's, yeah,

just really practical things,

day-to-day things.

Other times it's quite philosophical.

Other times it's quite emotional.

Like I just go wherever they are.

It's interesting that you

describe it as a plot

because that's quite a

powerful metaphor in of

itself because is it a soap opera?

Is it a thriller?

Is it a drama?

Is it a romance?

What narrative and what

story are they living right

now and what do they want it to be?

Earlier, and in your bio,

you talked about whilst

deep listening is one of your superpowers,

you described that when you

were in your corporate role,

and I think you spent a lot

of time in healthcare,

but at those senior levels,

you were able to help

leaders to cut through the

noise and make decisions.

What are some of those

strengths then that make

you such a powerful partner

to achieve that?

Yeah.

Appreciate your question.

I do the basics really well.

People notice that I do that.

I'm really good at mirroring back.

So if we're in a session and

you tell me a whole bunch of stuff,

I will stop you.

And before I start problem solving,

I will look back and say,

here's what I think I'm hearing.

And I will double check that

the thing that I thought

I'm hearing is actually what I'm hearing.

And when I get a yes,

then I try on what I think

is under the thing that I just heard.

And sometimes it can be feelings.

You know, I play a game with,

especially my male clients,

which is like pick a feeling.

And so then it's just like, well,

just like not very good at it.

Like we're just not

socialized to be like super

in touch with our feelings.

and um look I'm obviously

horribly generalizing but

uh it it can be kind of fun

so um you know they'll I'll

they'll tell me a story and

you know and I'll say wow

how does that make you feel

and they'll be like what do

you mean I just like I need

to get through it like we just you know

It's like a problem.

I'm like, yeah,

but you're having a feeling.

I can sense a feeling.

Tell me the feeling.

Sometimes they just either

refuse or can't find the right one.

And I'm like,

I'm going to give you a pick list.

Are you pissed off?

Are you angry?

Are you upset?

Are you frustrated?

Are you sad?

Pick one.

Yeah, pick one.

Are you miffed?

you know, BAFT, you know,

and at some point they'll

like get one and then I'm like,

and then you watch them and like, ah,

and like,

there's something powerful about

just naming the field.

Right.

And you just,

just on a basic psychological level,

just like attaching the

emotion to the thing that

you're experiencing.

It's actually really quite helpful.

And we're not very good at

that for ourselves.

And so, I mean,

they're just some light

things that I like to do.

I do spend a lot of time

listening for the story

under the story and helping people, like,

reconnect with what is really going on.

And I'm very boundaried.

So, you know, my wife is a psychotherapist,

so I have way too much

respect for people that do

clinical mental health work.

Um, you know,

and I'm not a lawyer and I'm

not an accountant.

Like I, I, I know where my bounds are.

Uh, so I'm very careful.

Like if we hit something

that feels like childhood trauma,

I'm like referring out.

Right.

Um, but I, uh,

but I do really know where I'm,

where I'm good.

Uh,

and so helping people make decisions is

something that I'm good at.

And so like,

I'll frame up what I think the

choice points are.

I'll work with them on consequences.

I'm pretty good at scenario planning.

If decisions are actually

just hard conversations,

and often they are really

hard conversations,

something that I'm also, I think,

pretty skilled at is

scripting people to have

difficult conversations.

So I'll play the other

person and I just make them say it to me.

And I'm like, let's do it again,

except say these words.

And I give them the words

and usually we can rehearse

a conversation enough that

when they do it in real life,

it's way easier than they

ever imagined it was going to be.

It's interesting,

as I listened to you there,

especially the piece around emotions,

because certainly when I

started my career being told, you know,

it's not personal,

it's just business and

leave your emotions.

And for many of us,

we've been raised on that, you know,

nothing to see here,

British stiff upper lip, walk it off,

you know, just keep going,

keep calm and carry on.

In fact,

I have here the coaster that even says it,

but there you go, keep calm and carry on.

But to your point,

if you can name the emotion

and not just go with the

generic umbrella of I'm angry,

but actually, no,

are you angry or are you miffed?

It's all valid.

But depending on whether

you're at the angry, you know,

incandescent rage end of

the scale or just miffed,

it's a lightweight irritation.

All of it's influencing our

behavior and what we're

thinking and the stories

we're writing and therefore

how we're showing up,

not just for our colleagues,

but for ourselves.

And so when we can get to that underlying.

I won't even say truth,

but that underlying aha, as you said,

the story below the story,

the meaning between the words,

it can be like a light bulb moment.

one of my as well it is a

relief so what I will often

do in order to help elicit

that relief is I will

assign homework and my

favorite homework when it

comes to emotions is get a

bag of popcorn or your

favorite snack of choice

and you've got to watch

inside out inside out too

is pretty good too but

Inside Out, the first one, I mean,

it just reinforces the

importance of all the

emotions need to be there.

You can't have joy without

sadness and so on.

And seeing leaders come back,

having actually followed

through and then talking

about it just opens that

door a little bit more for

them to be able to explore

their own relationship with themselves.

Yeah, for sure it does.

What does that spark for you?

Well,

I think what it does also is one of

the secondary benefits to

working with somebody that

does the kind of work that

you and I do is that we're

actually kind of modeling

how they can be in their

relationships and their direct reports.

So I'm teaching how to ask

questions and how to hold

the space and listen.

And often people that work

with me for a long time, they'll say, oh,

I was doing a Jonathan

yesterday in this meeting.

I just sat there and all I

did was ask questions.

And it was amazing.

They figured it all out by themselves.

And like that to me is great

because like I'm modeling a

kind of a way of managing a

way of leading that takes practice.

It's not just intuitive.

Like we've been, you know,

you talked about like how

we've been socialized,

the stiff upper lip and all that.

We've also like been socialized, you know,

in a really like

predominantly male

corporate culture that

rewards speaking up first,

taking up a lot of space, being right,

being assertive.

And all of these things are

really being called, appropriately so,

into question.

And like I do a lot of work

with Indigenous people in Canada.

And they are the greatest teachers for me.

And they have a way, what they call,

like there's a Cree word for it,

but they have a way of

basically like called visiting.

And so they visit before they meet.

And so their meetings take a long time.

It's kind of like a

well-known understood thing.

If you're meeting with indigenous people,

it's going to take a long time.

But there's enormous value

in why it takes the time

that it takes because they

go slow to go fast.

So they meet and they

connect deeply and they

share and they make sure

that as and when they're ready,

that they don't have,

they know who each other is

and they connect, they're connected.

And so they can actually

bust through stuff super

fast when the time comes

because the relationship

has been nurtured.

And I think about those,

I think about those things a lot.

Yeah, well, it's that connection,

deep connection that goes

beyond just the job title or, you know,

I'm meeting Jonathan in thirty minutes.

What does he want?

And then can I give it to

you or get what I want from

you as quickly as possible

because I'm on to the next

meeting in thirty minutes and yada yada.

And super transactional.

Yeah, it does.

It drives super transactional.

And to your point in that great example,

just slowing down long

enough to spend a few,

even a few minutes at the

beginning of a meeting with

the how you're doing.

Hey, it's snowing here in Colorado.

How is it where you are?

It feels like you're wasting time.

But it is actually starting

to build those seeds of

connection and trust that

will make it easier for us

to work together on the tough days.

So you talked about

relationships or you used

the word earlier.

What role have relationships

played in your success?

I think they're everything.

I mean, like,

like relational dynamics are

kind of everything.

I pay an enormous amount of

attention to them.

I sit on three corporate

boards and one nonprofit board.

And really like the best

thing about boards is that

there's a study and

human dynamics and

relationships because it's, you know,

a group of humans that are

brought together to act in

the best interests of this entity.

And all of that is about how

we relate to each other and

how we incorporate each other's thinking.

So I feel like they're kind of essential.

There's something that they

need tending to.

They, you know,

they grow weeds and they wither, you know,

picture metaphor.

uh but um I think with the

right amount of attention

on them then um they're the

most beautiful things and

um they're also the things

that carry our businesses

up and out and you know

there's a lot of talk about

scaling um you know really

what scaling is is building

relationships with people

with clients with customers with

uh, staff and, um,

and suppliers and all the things.

Um, and,

and that's really at the heart of it is,

you know, do I trust you?

Are you going to trust me?

Are we going to follow

through and follow up on

the things that we've said

we're going to do?

And if we are,

and we can count on one another,

then we can do it together.

And, you know,

that times one times one

times one gets us to, uh, you know, grow.

And I think at the heart of it, that's,

that's, that's what,

that's what sparks it.

So I'm curious then with all

of the relationships, personal,

professional in your life,

what's one habit that you

consciously adopt to

nurture those relationships?

I have a very precious newsletter list.

There's four hundred and

fifty three people on it.

And I know every single

person on that list.

I write a monthly newsletter.

And every year I go through

my list and I look at who

haven't I spoken to on the

phone in the last year and

I book a meeting with them.

And so I don't need ten

thousand people on my newsletter list.

I just need four hundred and

fifty people that really,

really care about me and my

work because they all know ten people.

And that's a way better

number for me in terms of

like my universe of referrals.

So I just I care about that a lot.

You can't like you can sign

up for my newsletter and go

ahead if you're listening.

That's great.

There's one hundred percent

chance I will reach out to

you and book a call.

if you do uh because I

actually want to know

people that are getting my

monthly uh emails and um I

it's not a transactional

salesy thing I like get

quite philosophical I get

quite deep uh in my writing

when I'm when I'm putting

it out and I want readers

that care about the things

that I care about um to be

you know on my on my list

so um I suppose that's my

People don't ask me about that, but anyway,

you did.

So that's something that I

do that's very intentional.

Well,

it's wonderful because it's inspired me.

I am similar in mindset in

that it's not quantity that matters.

It's quality.

And so the same with my socials,

the same with my list.

What I had not thought about doing, though,

which you've just inspired me to,

is that personal outreach of, hey,

it's the holiday season.

And I was thinking of you, you know,

what's happening in your world.

So four hundred and fifty

three on your list in a few minutes,

it will be four hundred and fifty four.

puppy dog okay now we have

to pause the podcast

conversation so tell us

about the dog that just

appeared behind you unless

it's the neighbors and you

do no it's my that's my dog

chloe uh if you're

listening to this on a

podcast uh she's a black

lab crosshound um thirteen

years old and she lives on

that couch mostly she

doesn't move during podcasts so yeah

No,

that was delightful to see her come in.

Well, Jonathan,

it has been a pleasure for

this first date conversation.

Thank you for spending time

with me today on People First.

Where can people learn more

about the work that you're

doing and your executive

coaching practice?

Yeah,

so you can find me online at

clearlythen.com.

I'm also really active on LinkedIn.

So you can just look me up,

Jonathan Bennett on LinkedIn.

Reach out if you want to

book some time with me and

hang out and learn a bit

more about my work.

I'm a real person.

I respond to DMs and happy

to spend some time with

anybody that's interested.

If you're a leader with some

things in front of you that feel hard,

happy to talk.

Well, Jonathan,

from one real person to

another real person,

thank you again for your insights.

We were definitely better together.

And with the added bonus of

Chloe joining us too,

I wish you all the best for

the year end and continued

success and happiness in all that you do.

Thank you.

Thanks, Maureen.

Thank you so much.