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June 30, 2025 54 mins

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What if the best leaders aren't the ones with the answers, but the ones who know how to ask the right questions?

In this episode, I sit down with former Army officer turned leadership coach Chris Duprey to explore the mindset shift that turns managers into powerful communicators. Through his Pathfinder’s Compass framework, Chris breaks down the difference between leading by instruction and leading by inquiry. Spoiler: It’s less “boss mode,” more “Ted Lasso with a mission.”

They get deep into the four pillars of breakthrough communication, Yes-And energy, vanguarding concerns, a question-first mentality, and the Law of Three, and explain how they help leaders develop other leaders. Whether you’re navigating team dynamics, family conversations, or your next big presentation, this episode reveals how curiosity, self-awareness, and intentional listening are the tools that change everything.

Chris shares how the military taught him the importance of active listening and how that lesson stuck with him far beyond the battlefield. His approach isn’t about surface-level leadership tips, it’s about building trust, growing initiative, and empowering others to find their own answers.

Connect with Chris:

https://www.linkedin.com/in/cduprey/

https://questionfirstgroup.com

Visit TimNewmanSpeaks.com to grab your free eBook, The Top 21 Challenges for Public Speakers and How to Overcome Them, and start building the confidence you deserve!

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Want to be a guest on Speaking With Confidence? Send Tim Newman a message on PodMatch
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Episode Transcript

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Tim (00:08):
Welcome to Speaking with Confidence, a podcast dedicated
to helping you unlock the powerof effective public speaking.
I'm Tim Newman, a recoveringcollege professor turned
communication coach, and I'mthrilled to guide you on the
journey to becoming a powerfulcommunicator.
I want to thank each and everyone of you for your support.
It truly means the world to me.
If you have questions or if youwant something covered on the

(00:31):
podcast, just send me a message.
Please visittimdenwithspeakscom to get your
free ebook the Top 21 Challengesfor Public Speakers and how to
Overcome them.
Today's guest is Chris Dupre.
Chris is a former Army officerturned business leader and coach
dedicated to helping peopleuncover their untapped potential
.
His journey began in the 82ndAirborne, where he learned the
power of listening, leadershipand guiding others to find their

(00:53):
own solutions.
After the military, he ledteams in business, earning his
graduate degree and shaping hisapproach through mentorship,
mindfulness and the power ofgreat communication.
Now a partner at the QuestionFirst group, chris helps leaders
and sales teams have betterconversations, build deeper
connections and create realbreakthroughs.
His mission is simple todevelop leaders who create other

(01:16):
leaders Outside of work.
He's a musician, a devotedfather and someone who believes
that with self-awareness andintentional communication,
anyone can achieve extraordinarythings.
Chris, welcome to the show.
It's always great to welcome aveteran and fellow 82nd Airborne
member to the show.
I really appreciate you comingon?

Chris (01:39):
Yeah, tim, I'm excited to have this conversation and,
again, like when you talk tosomebody that knows what all the
way means, it's a.
It's a totally different thing,right.

Tim (01:47):
It really is.
It really is, yeah, yeah.
I say that to some peoplesometimes and they just kind of
look at me and I said, no, justget out of the way.
Yeah, yeah, please.

Chris (01:55):
I remember signing emails ATW.
Exclamation point.
Exclamation point Anyway.

Tim (02:12):
So you know a couple of things before we really get into
it.
You know what?
One of the things I reallyloved about your, your
information that you sent me, isyour devoted father, and
anybody who puts that in their,in their bio or introduction,
really touches my heart, becauseto me, there's nothing more
important than family.

Chris (02:22):
Yeah, yeah.
So, I mean, you know, my kidsgrew up sort of during covid
yeah and by grew up, they're 15and 11 today, right.
And so, as they went to schoolfrom home, dad went to work from
home, right and one of thecraziest things that I saw is

(02:42):
they listen right like I'm in myhome office and the kitchen's
right there like staircase overthere, and when they get home
from school they're hanging outlistening to the conversations
that are happening.
They're like part of it andthey get to see you know what it
takes to do some of the stuff,and so it's just such a cool

(03:03):
like I feel like, even thoughyou work a ton in today's new
world, like they're here with meand you know getting your kids
are lucky to be in that position.

Tim (03:15):
My kids were lucky to be in a position that I was in.
You know, they grew up incollege campuses and interacting
with people and and that, that,that, that that really kind of

(03:35):
gives them a leg up or helpsthem stand out, because they
feel so much comfortable, somuch more comfortable, talking
with and dealing with peopleoutside of their age group,
outside of their comfort zone,and they see how it works.
So it's it's, you know,modeling that behavior is really
going to benefit them in thelong run yeah, yeah, 100, agree

(03:57):
100 so you play music.

Chris (03:59):
Oh yeah, I mean.
So you want to talk about thetwo biggest fans of my band?
Oh, okay.
Now, my daughter's too cool now, but like she loves a couple of
tunes, my son will sit thereand sing every word of every
song.

Tim (04:13):
Awesome.

Chris (04:14):
Yeah, so, so, and and my younger, so my son is the
younger one.
He can play a little bit ofguitar, he can play a little bit
of drums.
So he, you know, I meanfootball is his, his thing right
now, but he can also pick up aguitar and play seven nation
army and you know.

Tim (04:33):
But but again, you know, think about this from from a
developmental perspective.
You know, the more things thatyou can do, the more things that
you have experience in that.
That helps up here, right, ithelps how it helps in how we
think.
It helps in how we becomecritical thinkers, how we
interact with with, withdifferent things.
That that come our way and byexercising different parts of

(04:55):
our brain is what really makesus a more well-rounded
individual.

Chris (04:59):
Oh yeah, and you know it's.
It's an interesting thing.
I, my kids, learn how to dotheir own laundry and cook, and
and I know that some parentsthat like they don't do that,
but for me it was.
My kids can handle themselves,right, and so it's the same

(05:19):
thing with, like, trying toteach them how to communicate,
how to.
To your point of like, how doyou talk to people outside of
your age range?
Right, how do you do some ofthose things, those basic
lessons, even if they're outside?
Like my kid, he played SevenNation Army was the tune that he
loved, he had to.
He took some guitar lessons forabout six months and he did a

(05:42):
little recital where he playedthat up in front of 25 families.
Right, and what's that?
It's a huge deal for for this,for this little dude, right?
Yeah, and so setting up momentslike that is just key it.

Tim (05:56):
It really is, and and it's it's also teaching them a couple
, a couple things that I reallywant to talk about is, and you
know, there there are sometraits that that make people six
or or there are, they don'tmake them successful.
There are traits of people thatare successful in the military
and in in in private industry,in in in the civilian world

(06:20):
initiative and awareness.
You know, what have you foundin your current position, with
people revolving aroundinitiative and awareness, and
the difference between thepeople that are successful,
somewhat successful, and notsuccessful.

Chris (06:39):
Yeah.
So I think the number one Imean I don't want to call it the
number one killer of potential,but I think the biggest thing
that holds people back is thislack of self-awareness.
So when you go, look at leadersleaders that don't know how
their energy impacts a room,other communication impacts a
room, how simple things theysaid, like when they can't see

(07:02):
it, it has really negativeimpacts on an organization,
right.
The same thing is true Ifyou're not the leader, you're
just you're on the team, right,right.
The more aware we can becomeand I and I think what I mean by
that is the more we understandhow we show up and impact those

(07:24):
around us by just being the moreeffective we become.
Right.
Then you get to initiative, andthis was a huge part of being an
officer in the 82nd AirborneDivision, and I think it is a
limiting factor that I see in alot of folks and I don't want to

(07:45):
blame the folks.
It comes from dependency thatgets built from leaders.
Usually and this is the example, and this is this you see this
all the time Young leader getsput in the role of leader like
manager, super, whatever.
That is because they were thebest at the thing they did.

(08:06):
So, tim, they were the personthat took initiative.
They were the person that justgot after it, that just went all
in, did everything, took it.
Then we make them leader and wedon't teach them anything.
And so now we've added humansunder them and more things to

(08:27):
achieve, but they're so focusedon just achieving it that when
you, as the subordinate, come tothem and ask a question, they
just answer it right, and theyalways answer it and they always
.
You know, I don't like the wordmicromanage, but they basically
micromanage right.
So we create this bottleneckwith these new leaders, so the

(08:52):
people under them never practiceinitiative because they're just
told to do certain things.
Yes, and it creates this cycleof non-existent leadership.

Tim (09:06):
Yeah, because when that person that was elevated to
leader was never trained how tobe a leader, eventually they're
going to move up because that'swhat happens and they're not
trained there.

Chris (09:16):
They're not training this person and then it just becomes
roll over, roll over, roll over, and so what ends up happening
is the folks that work under.
Those folks feel no autonomy,they feel micromanaged.

Tim (09:31):
Managed.

Chris (09:32):
They go to be compliant, do the things I need to do so I
don't get fired versus committed, which is like I'm into the
mission, I'm into what we'redoing, I'm here, I'm giving you
everything I got every day,exactly Again, which leads into
the disciplined initiative.

(09:52):
And so when you look at folksthat have been super successful,
they're self-aware and theyhave this discipline, this drive
, right, right, and they havethis discipline, this drive,
right, right.
But what we don't ever talkabout is they usually have had a
great leader, leader that is, amentor that has helped them

(10:14):
break out of that horrible cycle.
Yes, yes.

Tim (10:20):
And that person then becomes a great mentor, correct,
and that's that's how that andthat's how how it kind of rolls
down.
You know, um, I had a last week.
I had, um, four of my formerstudents come to town.
They do a buddy trip every yearand and, and I was really
touched, this year they theychose to do it where I live so

(10:42):
they could come see me.
I mean, I keep in touch with mewhere they're.
They become, you know, closefriends and like family.
And one of them is a is acollege professor at 40 years
old.
Um, he's a department chair,full professor, and he was
telling me about some things andI had to take him back to some
of the things we talked about.
When he first started I saidyou know, first off, you've lost

(11:04):
sight of what your actual joband what your actual role is
because you haven't been trainedin these things and you have to
understand, you have to touchback with that.
Your job is to develop peopleto be successful in life.
It's not to teach them sportmarketing.
It's not to teach them this,that or the other thing.
Your job is to teach them sportmarketing.

(11:25):
It's not to teach them this outof the other thing.
Your job is to teach them how tobe successful in life.
Your job as a department chairis to help your, your, your
faculty members, help yourstudents be successful in life
right and get back to doingthose things.
And everything may not alwayswork out the way you want them
to do, but ultimately you'remeeting.
You're meeting your mission,you're meeting the things that

(11:48):
you're tasked to do.
The most important thing istake care of those students.
Yeah, yeah, and we forget thatsometimes, on all levels, in all
industries.
It happens in the military, ithappens in private business, it
happens in education, it happensin families, it happens all the
time.

Chris (12:06):
We get so with stuff, with life yeah, because there's
all these pressures, right,right.
So in the business world, right, you have, like you have
revenue targets, you have salesquotas, you have you marketing
kpa, like whatever it is.
That's a weight that you arecarrying around.
Yeah, and we can't, as leadersthat were aspiring leaders, let

(12:32):
that keep us from that missionof we have to create other
leaders and get them to developand grow right, right, because
eventually we're not gonna behere and somebody's gotta take,
take charge, somebody's got todo it, that's right.

Tim (12:46):
And just just something that kind of popped in my head.
You, you talked about beinginvolved in being committed, and
I always think about it fromfrom the breakfast perspective.
You know, the chicken isinvolved, the pig is committed,
hmm, yeah.
So, yeah, remember that.

Chris (13:02):
Yeah, oh, I like that.

Tim (13:04):
So you know we also talked about, you know, how we can help
.
One of the issues with youngpeople is they don't have a
framework in how to talk topeople Because, again, we're
never taught how to talk topeople.
It's just go, Go figure it out,go figure it out, and that's

(13:25):
what we had to talk to people.
It's just, yeah, go, go figureit out, go figure it out, and
that's what we had to do and andthat's great.
But we're in a different timein life.
We're a different time insociety.
That you know.
Again, go back to the, thehelplessness.
Because we've got this screencovering our face all the time,
there's no need to talk toanybody, because I've got this
screen covering our face all thetime.
There's no need to talk toanybody because I've got it all
right here.

Chris (13:46):
Yeah, and so I think that this is this is where it all
comes down to is becauseeverything's so much faster
today, because everything isjust immediate.
We think that we can keep thatjust text based communication
going, and the reality is, whenyou get to a certain level, you

(14:08):
can't, because I've never, I'venever seen conflict get resolved
or a breakthrough happen in anemail exchange or in a Slack
exchange.

Tim (14:19):
Exactly, it doesn't happen.
All those do is it creates moreconflict, it creates more
confusion.
And here's Chris.
Let me just say this there'snothing.
A lot of things aggravate me,but there's really nothing that
aggravates me more than whenpeople complain that things
aren't being solved through anemail.

(14:41):
Pick up the daggum phone, callthem.
You can resolve this in fiveminutes, yeah.
Get up walk down the office.

Chris (14:51):
Yeah, when I was, when I was the COO at impact, used to
hear this all the time and belike I'd see it in Slack and
just go.
Why didn't you just call themor get on FaceTime or something
like, like some sort of where wecan see and hear each other if
we're not in the same building?
But it's become so air quoteseasy, right To just send a

(15:16):
message, and I think it it itstems to what you were saying,
tim, is that we don't have aframework to go back to.
Him.
Is that we don't have aframework to go back to, we
don't get taught how to, quitefrankly, get past some of the
junk that ends up in our ownbrains that gets in the way of
effective communication.

(15:37):
Exactly one of the one of thebiggest things and I think it
was reading James Clear's bookAtomic Habits that he talked
about this about how the brainuses the most calories of any
other organ in the body.
Right, and so it it then to tryto resort, like to save energy.

(15:57):
It buckets things together andthis is where assumptions come
from.
Right, so right, we hear thesame thing over and over, so we
automatically make the jumps inhere to that thing, yeah, and
assuming is good in planning.
Okay, like you remember fromback in, our days in the 82nd
right.
You have to assume when you'remaking a plan, but the first

(16:20):
thing after the plan's done isyou send out reconnaissance to
go confirm or deny thoseassumptions Exactly Right.
Right, but we don't teachpeople how to do that
reconnaissance in communication.
And it's so simple.
Yes, it's just asking questionsit's, it really is.

Tim (16:41):
And you know, for those, for our listeners.
You know, chris and I did a apre-show call and I record.
I record all those calls, youknow, for for my research, to go
back and plan for this.
And it hit me when we had thecall.
But it hit me again when I wentback to watch.
You asked you know we weretalking about, you know where

(17:01):
people were getting hung up, andthen you thought for a second
and then you asked anotherquestion and then you asked
another question.
You said now you get it.
And that's how simple is that?
How simple is that?
Just ask the questions.
You know, if you don'tunderstand something, ask the
questions.
If you want clarification, askthe questions and let's pinpoint
what the issue is and then wecan deal with that issue and

(17:23):
then we can move on to the nextissue.

Chris (17:25):
Yeah, and, and so we we call it that the question first,
we call that the law of threeright.
Where it's like, hey, yourfirst answer is likely never the
real answer, it's not the rootcause thing.
So if you ask somebody, solet's, let's.
Let's stick with my daughterfor a second.

(17:45):
If I asked my daughter when shegets home from school today, I
was your day, she's 15, she's asophomore in high school tim.
She's gonna say the f word.
It was fine.
Do I know anything in thatmoment?
nothing no, I don't knowanything right.
But then so too many of usaccept that non-communication

(18:10):
and we just move on.
Yes, but I go well, hey, what?
What happened today?
It was like different from anyother day.
And she'll say something likewell, how did that impact this?
And now we're in what?
now you have so many parentsdon't get into, which is a
conversation with the kidconversation yeah, yep, you know
, I love going even a stepfurther, going, hey, brooklyn,

(18:32):
on a scale of zero to 10, 10 wasthe best day ever.
Zero is the worst day ever.
Where was your day?
Because there's a thousandthings to unpack them.
Yep, absolutely.
But we can do this withanything a team conflict, a
research, like.
If you're curious, tim, like Ithink this is the.

(18:59):
So you've got self-awareness,you've got discipline, but we
have to be curious, not curiousin the way that we just ask siri
or we like type it in, butwhere we're like well, I want to
hear what Tim has to say.
So, tim, what do you thinkabout that?

Tim (19:14):
Right, it can be that simple, yes, and.
And you know, just just in thatexample or scenario, what, what
, what is happening to Tim?
He's thinking wow, chris, chriswants my opinion.
What.
Nobody's really ever asked memy opinion before.
Right.

Chris (19:35):
And, and what do people love to do tim?

Tim (19:37):
talk about.

Chris (19:37):
We love to talk about ourselves, right, we do when.
When I meet young sales repsthat don't ask questions, I'm
like gang.
You know, if you just ask themwhat their day-to-day looks like
, they're gonna tell you yeslike, yeah, if you.
It's like, it's like field ofdreams and now I've dated the
two of us.

(19:58):
It's a movie where, if youbuild them, they will come right
and kevin costner builds abaseball field and what is it?
The 19, I don't know.

Tim (20:08):
It's like it's a black socks the black socks black
socks scandal, you know scandal,the early 19?

Chris (20:15):
It doesn't matter.
The whole point is, if youbuild it, they will come.
If you ask questions, peoplewill answer them.

Tim (20:26):
Unless your wife Asked you what you want for dinner.

Chris (20:29):
Whatever you ready for, the here's the deal.
That one's a hard one.
Here's the deal, tim, and it'snot like that one's a hard one,
but here's the, here's the onethat we always joke about.
Where do you want to go fordinner?
And your partner says I don'tknow.
Here's the, here's the quick,quick win.
Yeah, but if you had to chooseone place, yeah, what would it

(20:50):
be?
And people could almost alwayschoose that one place because
when we say where do you want togo?
It's broad, right, yeah.
But if you haven't just give meone choice, they're going to
answer you.
It's the craziest thing.
It works.
I use it with uh.
I use it with my partner allthe time.

Tim (21:10):
That's awesome.

Chris (21:10):
I hope she doesn't listen to this and go.
Oh, that's the thing.

Tim (21:14):
So that's what you've been doing all these years.

Chris (21:15):
Okay, now I got it.
Yeah, there you go, yep.

Tim (21:19):
That's awesome.
So, you know, let's talk aboutthe, the, the, the graph from
radical candor that we went over, because I think that that
number one that's going to helpsimplify it, for our audience.
That's going to help simplifyit for our audience, and then we
can start to really kind oflook at wow, this is what

(21:43):
happens.

Chris (21:43):
And this is where I don't want to be and this is where I
really want to get to, yeah, sobefore I share it, let me let me
give you a quick rundown here.
So when the partners of thequestion of first group got
together, we were going to filmour first course and we're like,
hey, we were all huge fans ofKim Scott's work radical candor,
we.
We love teaching it.
It's the simplest frameworkbecause of this graphic that she

(22:06):
has.
And so we drew the baselinegraphic, which was just a North
South arrow and an East Westarrow, right, and we said what
is our version of this?
And so that's what we're goingto go through.
We call it the path, excuse me,we call it the pathfinders
compass.
Okay, and you can use it toassess any, um, any leadership

(22:29):
situation, any communicationthat you that you go through,
any communication that you gothrough.
So let's start at the basemodel of this.
So you've got the North Southarrow.
This is who is the beneficiaryof the conversation?
Is it our audience or is itourselves?

(22:50):
Then we have the East West, andnow this is the spectrum of
curiosity, right, are we askingquestions or are we telling?
And so take a moment and drawthat and the reason that I say
that that's what we have to do,tim, is that that gives us this
blank canvas to go.
Okay, if I were to assess myconversations in the last month,

(23:14):
here's where I generally fall.
Well, they're really about megetting my needs met and I
really just tell people what Ineed.
So I'm in that bottom leftquadrant, okay.
So good, go think through that.
Now let's look at what thoseactually are and as we go
through them, I'll build out thewhole thing.

(23:37):
So we have here in the bottom,so where the folk, the intended
beneficiary, is ourselves, andwe're primarily telling this is
the command and control stylethat we call the dictator.
So think of early steve jobs atapple.
This is just to do what I saybecause I've said it.

(23:58):
Then we go over to the bottomright, engineered manipulation.
So think of harvey specter fromsuits.
Right, this is the lawyer, thisis the prosecutor.
Right, they're trying to justthey're asking you questions to
say the thing they want you tosay, right, okay.
Then we go to the instructor.

(24:19):
This is prescriptive engagement.
Think of this.
Could be like the sales leaderthat got promoted because they
were the best salesperson.
It's like hey, just say itexactly this way and you're
going to win.
I'm rooting for you.
So they tell you everything,but it's for your benefit.
Then we have guided discovery.

(24:39):
This is the pathfinder.
This is where we want to be.
My favorite way to put this isthis is the Ted Lasso character.
Yes, ted is a great, that isawesome.

Tim (24:49):
I'm glad that is awesome.

Chris (24:51):
Yes, so so that's the Ted Lasso is the Pathfinder, and
it's this idea that we'refocused on.
The other, like our audience,we're focused on helping them,
but we're asking them questions.
Because, tim, when I ask youquestions, what does it force
you to do in a conversation.

Tim (25:13):
It forces you to think and engage yeah, to think and engage
.

Chris (25:18):
And when we think and engage, that's when we actually
develop this disciplinedinitiative, this awareness of
what we're doing or not doing.
This is how you create moreleaders yes if you just tell
them exactly what to do, youcreate clones that follow a

(25:40):
system, and that's it right,exactly.
Here's the tricky part nobodystays in one box all the time.
Right, right, right.
And so go back to thisawareness pieces.
When do I find myself tellingmore than asking?

(26:02):
When do I find myself worryingabout me and getting what I need
done versus helping the personthat comes to me?
And the biggest thing that I seeespecially younger leaders
helping the person that comes tome, and the biggest thing that
I see, especially youngerleaders will have people come to
them.
They'll answer every question.

(26:23):
They will be the instructor orthe dictator.
They fall into one of those two, and when you ask them why
they're like I just don't havethe time to have the real
conversation.
Yes, but the thing that helpsget the breakthrough is like
well, how many times does personA come see you in a week?
Oh, like four or five times aday.

(26:43):
Okay, so is spending one30-minute conversation to get
them to see the thing betterthan having 30 or 25
interruptions throughout yourweek?
Right, but sometimes we have topaint that for leaders Exactly.
The key, though, is that we'refocused on this, because if

(27:06):
we're not focused on it, thenthe vicious cycle that I will
call of non-leadership continues.
I will call of non-leadershipcontinues, and you have all of
these sort of lemmings doingwork and you have the stats that
you see from Gallup and Gartnerof unengaged employees at work.

Tim (27:29):
Yep, yeah, and I think you nailed it with the whole time
thing.
If we were to step back andlook at it.
Yes, it takes time to buildthis relationship.
Yes, it takes time to teachthem and guide them, to be able
to get to this point.
And, like you said, what youdon't really think about is all

(27:50):
the time that you're wasting wayover here, just, you know,
telling them what to do, tellthem what to do again, do it
this way, do it that way, gocall steve, go, go do whatever,
as opposed to taking the time tosit down with them, teach them,
guide them and build.
Build the relationship, becauseI know we're going to get into

(28:15):
this, but that that it's thatrelationship that is, is, is the
ultimate, is our ultimate goal.

Chris (28:21):
Right, and just think about this.
It can be as simple, tim, as anemployee comes up to you If
you're a new leader, to say whatdo you think we should do with
this, you just say, hey, listen,I've got some ideas.
Before I tell you what I'mthinking, what's coming to mind
for you, exactly, exactly.
And so there's a.

(28:42):
There's a.
One of the things that a lot ofpeople struggle with is they'll
hear this message and they'lljust say, well, what do you
think?
And now, with certain people,that's going to be fine, but
certain people also want to knowthat you still got their backs.
It's like, hey, I'm going to befine, but certain people also
want to know that you still gottheir backs.
It's like, hey, I'm going tohelp you and we're going to
spend some time here, right, andthat gets the ball rolling.

Tim (29:03):
It really does.
You know, and I did.
I did something similar to thatwhen I, when I was a professor,
you know they would want me togive them examples of this,
example of that.
I said you know I can do that,but if I'm going to do that, you
can't use any of those examples.
So let's, let's talk it throughtogether.
You know what are you thinking,because what you're thinking is
probably going to be a littlebit different from what the

(29:23):
student over here is thinking.
So let's, let's, let's sit downtogether and start walking
through it, and then you can seetheir faces go.
Oh my gosh, now I really haveto think about this, instead of
just taking what somebody elseis telling me to do, doing it
and then, once they get it it'skind of like that email that you
got a little bit ago, it's.

(29:44):
It makes you bingo.
You know you want to high fivepeople and just kind of it's you
got it now Now.
Now do that all the time.

Chris (29:57):
Yeah, it's, you got it now.
Now, now, do that all the time.
Yeah, I, I gotta tell you this.
I listen, I've been a coach nowfor about five years.
I probably have 4500 hours ofcoaching under my belt,
something like that and I'dnever received an email like
this one from a young leaderwho's who's likely around the
you know, like the same age as alot of the listeners, right,

(30:20):
like a lot of folks.
And the overarching message thatshe she said to me was how
unequipped she felt in herleadership abilities.
She was like thrust into thisthing.
She was shooting in dark,trying to understand how to
develop people, and she had thiscaring about it.
She wanted to do it.
She had a strong desire to doher job, be the leader that she

(30:42):
looked up to, but she had noidea how to do it.
But she had the initiative, tim, and the awareness to go.
This training is hard, but I amgoing to suck it up and get
through this discomfort, and nowshe feels like she understands

(31:03):
how to actually coach and teachpeople.
The burden of leadership isless.
The training is something thatshe likely will talk about for
the rest of her life.
Yes, now that is from.
So you're ready for thecraziest part.
Yeah, I've never met this humanin in like real life.
We've only met virtually andwe've only worked together for

(31:27):
about five months how about that?
that's awesome yeah I read it inthe car at the post office as I
was about to file the company'stax return, and I like started
crying because it was like holysmokes.
This is what you can do whenyou just have real conversations
with people.

Tim (31:48):
Exactly, exactly.
And, and you know I love thewhole idea that, that she um
admitted that it was hard,because, you know, that's that's
where the learning occurs, thehard part, when it's the
learning, it doesn't happen.
When it's fun and nice and good, and the learning is the hard
part, it's that, it's that, it'sthat struggle, that's where the

(32:08):
learning occurs.
And so you, you better embraceit, you better embrace that
learning.

Chris (32:13):
Yeah, it's the.
I had this old sales coach whomI love, a guy named Jack
Carroll, and he used to talkabout the different, like the
cycle of learning, and he waslike you start with unconscious
incompetence, you don't knowwhat you don't know no, right,
so it was like you know, thinkabout your kid learning how to

(32:36):
ride a bike.
They have no clue when theystart.
Then you get to consciousincompetence.
So you know what you'resupposed to do, but even with
the training wheels it's likereally tough then.
Do you remember when you tookthe training wheels off your
kid's bike?
oh yeah and so this is when theyget the conscious competence.
So they had to think abouteverything they were doing, and

(32:59):
I remember my son started goingand he couldn't turn because he
was so focused on stay balanced,keep pedaling, and I just
watched him go right down thedriveway and then right into the
road.
Granted, we live on acul-de-sac, so it's fine, but he
didn't know because he was sostuck in it.
That's the hardest part, right?

Tim (33:19):
Right.

Chris (33:20):
Then you get to unconscious competence, where my
kid just jumps on a bike, he'snot thinking about anything and
he's off and running.
That's how we basically learneverything right Exactly it is,
it is.
And the hardest part is that,getting past the hump of knowing
what right looks like and beinglike you're constantly thinking

(33:40):
about what does right look like, so how do I do it until it
gets ingrained and that's, and II believe that that is where
this young woman is now of.
It was really hard to get,really hard to get, really hard
to get, and then she got it.
that's awesome good for hersecond nature right, yeah, but
this can be true, like this is.

(34:01):
The thing is that I I love herto death and I don't think that
she's super special.
She just did the work right tobecome the leader she wanted to
be, so so anybody listening canlearn how to lean into, how do
we put our focus on others, andbe super curious and like

(34:24):
hopefully, you're lucky enoughthat your organization invests
in leader development aroundthis stuff.

Tim (34:31):
Right and and again, that's also a big key.
You know when, you know we.
We talk about a number ofdifferent things.
Number one you, you as anindividual, need to to know who
you are, what your values are,and so when you go and you
interview with a company, youneed to know that already and
you need to have an idea of what, the what, what does that

(34:52):
company value?
Um in in in terms of you knowtheir employees and and and how
they're going to help them.
Because I, I, I truly believeit's our responsibility to to,
to be leaders.
You know, I I don't wantsomebody I mean to to not ever
develop and just stay in oneposition all the time.

(35:13):
I would much rather havesomebody come in and develop and
move up.
Or you say you know whatthere's, as much as I love it
here and as much as you'rehelping me, the next position
for me is in another company.
I would much rather have thatperson Because, you know, not
not only do they do, they valuewhat we did for them and what we
would continue doing for them,but they're ambitious and they

(35:35):
want to get better themselvesperiod, and they may eventually
even come back to us and I findthat, working with a lot of
small to medium-sized businesses, they really want to invest in
their people.

Chris (35:47):
Yeah, and I think even in the bigger organizations that's
still a piece.
In the bigger organizationsthat's still a piece.
The big mission that that I'mon is getting both large and
small companies to understandthat the problem we have is a
lack of real leadership training.
Yeah, like it is a workshop onhow to do one thing of like that

(36:14):
isn't enough.
The like I mean.
I remember I remember being inthe 82nd, the amount of times
that we jumped to just, and allthe practice and rehearsals that
went into every jump.
Um, the amount of time youspent on the rifle range.
Like you insert anything, aflippant parade, right yes, a

(36:37):
change of command ceremony yesoh, there's a whole week's worth
of practice, right, but that'swhat it takes to get to these
points, right?
So if we think a annual retreatwhere we have a speaker come in
and talk to us about the bookthey wrote, that's not enough.

Tim (36:56):
No that's right, that's not that's, that's that's some time
off, that people aren't payingattention to that.
They're aggravated that they'renot getting things done that
they want to get done and itit's.
It may touch a few people, butbut you they completely missed
the boat.

Chris (37:14):
Yeah, and so when you get into real leadership
development and coaching andtraining, you get leaders
together, you get young andseasoned and all this stuff and
you have real conversations.
I was with Tim.
I was with a company yesterday.
It was a leadership team and wetalked about what are all the
issues and I'm just looking at Ihappen happening to be looking

(37:35):
at the piece of paper.
It's like it's over 15 thingsthat they all had about how they
communicate, about all thesedifferent things, and it was
like y'all have this gift.
Like the two owners were in theroom and their wife
participated and it's like we'reactually going to go get to
solve that stuff.
Yeah, and most of it's becausey'all don't know how to
communicate with each and that's, that's the thing.

(37:58):
So when I think about you know,my daughter is going to be in
college in a couple of years.
A couple of years after thatshe'll go into the workforce
she's a hundred percent going tohave to learn how to
communicate correctly and bycorrectly I just mean just be
curious, curious, stop assuming,lean into asking questions and

(38:23):
let's get that to be the normand have this like where we show
up with, like this questionfirst, mentality of.
Hey, before I get defensive,before I make a judgment, let me
unpack what they mean.
Like too often, you know, haveyou ever, um, you think of a
sales professional?

(38:43):
If you tell a sales guy, well,I just think that it's a, it's a
bit expensive.
What's the first thing thatthey usually do in that moment,
tim?

Tim (38:52):
Well, they ask the following question what is that?
What's too expensive?
What is it that you want themto do?

Chris (39:00):
So listen so that's if they get trained right.

Tim (39:02):
Like well, hey, what does too expensive mean?

Chris (39:04):
Yeah, yeah, but here's what you're a communications
coach so of course you answeredthat way.
But let's talk about mostsalespeople, brother.
They're going to go to adiscount or they're going to
lean into their pitch.
Well, you know, it's reallyabout the value and blah, blah,
blah.
And we, as the consumer, likeI'm good, right, right.

(39:27):
But the simplest thing is justhey, what do you mean by too
expensive?
Because too expensive forperson A might be completely
different than for person B,exactly Right.
And all we have to do is askthe questions and that's how we
get there.

Tim (39:43):
Right, right, I'm sorry, I that's just.
Yeah, that's what you know.
I mean, but that's but.
But you're absolutely right and, and, and, and.
Here's the thing when you startdoing that, that doesn't just
carry over into yourprofessional life, right?
Oh, that carries over intoeverything, yeah.

Chris (40:06):
So the funniest thing is the second that I learned this
stuff and worked with Marcus, mypartner, or one of my partners,
to like work on what isbreakthrough conversations.
What is this thing that we wantto do?
Made me a better dad, made me abetter partner, made me a

(40:26):
better human.
Just because, instead ofsitting there with this judgment
, you I got curious.
What well?
What the heck?
Well, what does that mean?
Right now, you know there'slots of things.
When you start getting curious,you like are open to more
things.
Right, and I fundamentallybelieve that that is just a

(40:49):
better thing than being closedoff absolutely it's, it's 100,
it's 100 better, better thing tobe yeah, it's, it's like the
idea of if you have no foodallergies, right, but this is I
learned, this happened over thelast like two years.
I'd never done one of thosefixed menus where a chef just

(41:11):
creates and like, but I but Iwent on this experience and I've
never eaten ceviche scallopsokay, and I live in new england
and they, they brought those outand it's like, well, I could
judge it, because it to me itwas air quotes, uncooked and
cold, it's like.
Or you could try it just try it,and so you just try it just try

(41:34):
it now.
Now here, I am talking aboutthat because it was like such a.
It was just trying somethingnew, yep, and curious about it.
Yep, open it up to somethingthat I actually do, sort of like
now, how about that?

Tim (41:50):
Yeah Right, the food referencing is a good one.
You know my wife loves sushi.
I can't stand it, oh yeah.
But, but every year on herbirthday, she says she wants to
go and get sushi.
So so we go.
So what do we do?
We go and get sushi and shesays are you going to eat it?
Yeah, I'll try it, becausemaybe I'll try something

(42:11):
different than I like, or maybeI'll try the same thing and I'll
like it this time.
It's yeah, it's about curiosityand and it makes her happy.
Yeah, heck, yeah, I eat so muchfood anyway.
If I have a bad meal or if Idon't like something, I will be
okay, trust me.

Chris (42:31):
I share that with you, my friend, I share that with you.

Tim (42:35):
So what are the four pillars of your framework?
You mentioned the rule three,which to me is yeah, I'm going
to say it's the most important,because that's the only one
we've talked about so far.

Chris (42:46):
Yeah, it's very important .
So listen, there's four, here'sthe deal.
There's nothing new or novelwith them.
They are four things that areout in the world, right, but
when they're brought togetherand we teach them the right way,
they become this great thing wecall breaks of conversations.
So the first one, which ispotentially my favorite, is yes,
anne and Tim.

(43:06):
This is literally stolen fromimprov comedy.
Right, we take whatever isgiven to us and we move forward
with it.
And I'm a huge Star Wars nerd,so I'm like for me, yes, and is
like the force that surroundscommunication.
Okay, so that's yes, and we'realways positive energy.

(43:27):
Our body language, everythingneeds to be moving us forward
positive energy.
Second one is vanguarding.
This is the idea of when's thebest time to address a concern
Before it becomes a concernright.

(43:48):
Right, Like if we address aconcern before it becomes a
concern.
We are not objection handlinganymore.
We are having the rightconversation.
Having the right conversationright, and sometimes it's as
simple as like hey, you might bethinking, and then you, you go
into it, right.
So vanguard is getting ahead ofconcern before they become
concerns.
You know, it's like what areall the but statements somebody

(44:11):
could make and how do youaddress them so they can't say
yeah, but what about this?
And and?

Tim (44:17):
that a lot of that goes revolves around the preparation,
research and knowing who,knowing your audience, knowing
who you're talking to, all ofthat stuff.
It's, it's it's so important toto have an understanding of
those things as opposed to oh,you know what I'm talking to
Chris today.
I have no idea what he's goingto say.
Let's, let's, let's wing it.

Chris (44:36):
Yeah, well, and it's also reading your audience, right,
yeah, so, hey, you're about tosay something like that.
They might sound weird.
Hey, I'm gonna say somethingmight sound weird.
To prep it right, and now it'sless awkward.
Okay, right, that's vanguarding, now that, like that, we chose

(44:56):
that as the title of this, goingback to, like the, the Roman
Legion, when they'd have thevanguard, would be out in front,
this idea that we're out infront of these things.
The third is question first.
This is it's not a leader's jobto tell people what to do.
It's their job to help themdiscover it for themselves.

Tim (45:16):
Yes.

Chris (45:17):
When I talk to sales folks I say it's not a
salesperson's job to sell thething, it's to guide the buyer
to make the right buyingdecision.

Tim (45:24):
Ooh, I like that.

Chris (45:26):
These are just think about the power of that one for
sales Right.
The second you stop trying tojust pitch and sell the thing,
you become a guide.
Yep, and we don't likesalespeople, we love guides.

Tim (45:42):
Yes, I like that.

Chris (45:47):
I really do, and it's just lean into curiosity.
And that last, that fourth one,law three.

Tim (45:54):
Yeah.

Chris (45:55):
They all tie together and that's how one becomes a
pathfinder is they leveragethose four pillars in all their
different communication.

Tim (46:07):
And and and again it comes back to you know, in, in, in
terms of that breakthroughcommunication piece you're.
You're building thatrelationship.
You're building thatrelationship and the more, the
more you're doing, the more openthey're going to be, the more
information you're going to beable to share and where you're
really going to get to the point, and then the more you're going
to be able to build that trust.

Chris (46:28):
Yeah, because the idea around all of this is it's we're
selling or we have people thatwe lead.
How do you build trust withpeople?
How do you build thatconnection they feel seen and
heard.
They believe that you actuallydo care about them have their

(46:49):
back right, right.
I mean, if you think of I knowyou go to, to the dictator,
right the steve jobs early appletype thing, he was just a jerk
and he wanted things done hisway.
Now I think he's a brilliantdude.
I think that I mean I haveprobably six apple devices in a

(47:10):
two they're all running.

Tim (47:11):
They're all running right now.

Chris (47:12):
Right, yeah, right yeah, like I'm on, like I'm looking at
four of them right now and myip I can't see, so there's like
at least five right, but theidea is he struggled at first
because he was just demandingwithout understanding people and
letting them do things Right.

(47:32):
And then, if you think of TedLasso, I was man, I, I love Ted
Lasso, tim.

Tim (47:39):
Like.

Chris (47:39):
Ted is like my like I just I, I love Ted, Lasso, Tim,
I do too.
Ted is like my like I just Iaspire to be more like him.
But if you think of the end ofseason one, he gets Roy to
self-discover that he shouldbench himself.
Yes, In that last game.
Yeah, Because Ted like I.

(48:00):
I mean I think the showportrays it pretty solidly that,
yeah, he would have let roystart if roy had said he was
going to start.
But he asked them somequestions, they talked about it
and you could tell that thecharacter of roy felt the
character of ted actually caredabout him.

Tim (48:19):
Yes.

Chris (48:20):
And actually wanted him to do what was right for him
Right, not what was right forTed Ted.
Not that was going to makeeverybody else happy, right, but
it was about what was going tobe right for Roy, and so it's
like how do we, as leaders, assubordinates, as humans, go, hey
, how do I help the person I'mtalking to?

Tim (48:43):
just just get better, yeah, do their thing and and you know
I tell people all the time, Idon't care what, what business
or industry you're in, what youdo, I don't.
If you're an accountant in acubicle, if you're an artist, I
don't really care.
It all it's all comes down tothe relationships that we build.

(49:05):
And you can talk about AI, thisand AI that, at the end of the
day, it's going to still beabout interpersonal
communication.
It's still going to be aboutthe relationships that we build.
Ai has has its role and has itsrole in communication, has its
role in business, but at the endof the day, it's about people,
it's about the relationships andconnections that we build.

Chris (49:26):
A hundred percent, a hundred percent, and that's why
this is important work, yeah,and it doesn't matter where
you're at in your journey, right, right, you could be.
You could be in a position abusiness owner, ceo, whatever,
you could be high school student, these things apply.

(49:50):
And the second that we realizelike, hey, I'm not as good a
communicator as I thought I was,and you start working on it,
yeah, your life will change.

Tim (49:58):
Your life will change and it's and it's a skill like
anything else.
Like I said, one leadershipclass where some guy comes and
talks about his book is not realleadership change.
Taking a class in high schoolor taking a class in college,
that's not.
You got to practice it.
Yeah, you have to go out and doit.
You have to do it and you haveto get better at it.

(50:19):
Yeah, you have to go out and doit.
You have to do it and you haveto get better at it.
You have to seek out the helpand again, remember that
frustration.
That's the learning.
Yeah, embrace it and get overit.
Chris, thank you so much.
Where can people find you towork with you?

Chris (50:33):
yeah, so on linkedin chris dupre, bald bearded
gentleman.
Um, right, or you can go toquestionfirstgroupcom and you
can find us there.
What if they want to see yourband play so you'd have to come
to band practice in middletown,connecticut?
Um, we, you know, this is the.

(50:54):
This is the fun thing of havingpeople at different stages in
our life.
My kids are old enough to behome alone.
Two of my bandmates have reallyyoung kids oh, so we have not,
we've not gotten out yet.
We are going to record soon andwhen we record I will make sure
that there are links on linkedinto to where the music is.

(51:16):
That's awesome.
That that's awesome.

Tim (51:19):
And you know what?
One of my favorite movies.
It's called the Drummer.
I don't know if you've seen it.

Chris (51:23):
I haven't With.

Tim (51:24):
Rainn Wilson Dwight from the Office oh yeah, yeah yeah, I
mean, it's classic, I'm writingit down.

Chris (51:33):
Yeah, yeah, yeah I will tell you last night not that
anybody's going to care aboutthis, but I saw Mumford Sons in
a 2,700-person thing Did you?
Really Wow.
And here's the takeaway thatactually is there.
For some people, that's a lotof people, but when you think
about a band that playsfestivals, that's a very small

(51:56):
intimate crowd.

Tim (51:56):
That's a small, intimate environment.
Yeah.

Chris (51:58):
Now here's the thing that's a very small, it's a
that's a small, intimateenvironment.
Yeah, now here's the thing whenyou get like-minded people
together, so at a festival, whenthere's 50 000 people maybe,
maybe five percent know all thewords to all the songs last
night, 2700 people knew everyword to every song and it was
this coming together and it was,and you could, you could see,

(52:21):
like just this, the piece aboutconnection, like you could see
them on stage looking at us inthe crowd and being overwhelmed
by the connection that was there.
And so if you haven'texperienced something like that,
I strongly recommend.

Tim (52:39):
That's awesome, that's, that's a it's.
It's powerful for for you, butit's really powerful for them to
see the, the, the marketthey've made.
Oh and yeah, you know the, the,the amount, the amount of time

(52:59):
and effort that goes into beinga musician and to the.
There's a smaller percentage ofpeople that make it as
musicians and bands than peoplethat become professional
athletes.

Chris (53:12):
Yeah, it's all about luck .

Tim (53:14):
It's all about being in the right place at the right time,
and to have that and to be inthose types of environments,
it's, it's, it's powerful yeah,and and so, and the funniest
thing is, as I'm trying to be acurious dude, that's what I
focused on.

Chris (53:29):
I was like look at, them like I want imagine what that's
like, and it was this whole newmoment, leaning into curiosity
rather than what a lot of folksmight do is lean into judgment,
and so I'll leave you with that.
It was super fun and, you know,someday, someday maybe I'll

(53:52):
play the 3000 in front of 3000people.
I don't think so, but we'll see.

Tim (53:58):
Well, you've got, you know, two of the best fans there
anyway, so that's all it reallymatters.

Chris (54:02):
That's right.
That's right.
They're honest to God.
The fact that they like themusic is a win in and of itself.

Tim (54:09):
Exactly Well, chris.
Thanks so much, buddy.
I really appreciate theconversation.
It was great and we'll talk toyou soon.
Yes, sir, thanks so much.
Be sure to visitspeakingwithconfidencepodcastcom
to get your free ebook Top 21Challenges for Public Speakers
and how to Overcome them.
You can also register for theFormula for Public Speaking
course.
Always remember your voice isthe power to change the world.

(54:32):
We'll talk to you next time,take care.
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