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June 24, 2025 24 mins

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What happens when a coaching conversation completely falls flat? In this episode, Zach Hensrude reflects on the worst coaching appointment he’s ever had—and the powerful leadership lesson it left behind.

Leaders often think they must say more, give more advice, or solve the problem. But real transformation happens when we learn to listen deeply.

Zach breaks down the 4 pillars of powerful leadership listening:

  1. Be Present – Your focus is the gift.
  2. Ask Clarifying Questions – Not to guide, but to understand.
  3. Facilitate Self-Discovery – Help them find their own answers.
  4. If They Can’t Self-Discover… Help them unpack what’s getting in the way.

If you’ve ever left a conversation wondering, “What just happened?”—this one’s for you.

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Episode Transcript

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SPEAKER_00 (00:03):
Welcome to the Different Thinking Podcast,
where creativity is welcome,conventional wisdom is tried and
tested, and growth anddevelopment are nourished so
that someday you can help tochange the world.
Now here's your host, ZachHensrood.

SPEAKER_01 (00:19):
I had, hands down, the worst interaction with a
coach ever.
in my life.
And this recently happened.
And so I had to hop on thepodcast because I know that
there's an opportunity to learnhere.

(00:40):
Now, if you know me, you knowthat I am all about coaching.
I think it is an important partof any personal development.
If you're trying to developyourself personally, you not
only need mentors, you not onlyneed people to train you, but
you need someone to coach you.
And that is someone to hold youaccountable for the things that

(01:01):
you want to do, not what someoneelse wants you to do.
And I think that's the beautifulthing about coaching is when
you're ready to make a change,when you're ready to do
something, there are people thatyou can hire, that you can bring
in your life that can hold youaccountable to the things that
you want to do.

(01:22):
And when you want to do them,that's the motivator behind
that.
So I tell you, after beingcoached professionally for eight
plus years and personally forthe last five years and having
some congruency betweenprofessional coaching and
personal coaching, hands down,had the worst coaching call

(01:47):
interaction being coached thatI've ever had in my entire life.
And it happened today.
Because it was absent ofsomething I'm going to discuss
today.
I knew it was bad becausegenerally when I'm being coached
and if there's a set time,whether it's 30 minutes, an

(02:08):
hour, hour and a half, I willtake up all of that time.
And there's sometimes thosecoaches that I work with are
very, very gracious and they goover time.
And we have a, a, a, asympathetical relationship
where, where we're workingtogether.

(02:29):
And I have good relationshipswith my coaches, even when I
miss on expectations, when Idon't do what I say I want to
do, even when they're giving methe, the medicine, the, the, the
stuff that doesn't taste good,the, the things that I need to
hear that I'm not very pleasedabout.
I mean, I'm willing to acceptthat.

(02:50):
because of my relationship withmy coach.
And I will tell you, thisinteraction with the coach was
actually not my regular coach.
It was somebody substituting formy regular coach.
And I will tell you that this isnot something that commonly

(03:11):
happens because if it was, Iwouldn't be working with that
company at all.
Actually, I believe that.
If the coaching does...
If it does not connect with you,then you should not be wasting
your time or money.
The coaching has to connect withyou.

(03:31):
You have to want to change.
No one can force you to change.
And if they do successfullyforce you to change, it's not
going to stick.
You are going to want to wantthis.
You have to want to want this.
So...
If you've been listening to mefor a short time or for since

(03:52):
the beginning of the show, youprobably can gather and I'll
just say it out loud now.
I don't just accept things theway that they are and just go,
okay, moving on.
I like to do something what Icall triage.
Some will call it debriefing oreven autopsy.
But what I like to do is I liketo walk back through whatever

(04:14):
that whatever that interactionwas, whatever that event was.
And I like to process it good,bad, the okay.
And I like to understand thepotential gifts, the lessons,
the empowerments that can comefrom an interaction.

(04:37):
And so just like I normally do,Yeah.
Yeah.
Yeah.

(05:04):
because of that interaction.
So going back through it anddoing my normal triage or
debriefing of that coachingcall, I do want to start off
with this caveat or right out ofthe gate that I subscribe to
what Jocko Wilnick and LeifBabin call extreme ownership.

(05:26):
So I'm never wanting to everlevel or lay blame on somebody
else because I Really, you havethat control over that entire
process.
And I'll show you in just amoment as I walk through this
podcast episode and the oneelement that was missing from

(05:48):
the coaching call that we asleaders, you and I as leaders
can give to other people.
So from the jump of it, whilethis was missing from the call,
I'm never going to blame thecoach.
The coach was not at fault.
I think if she was listening tothis, I think there could be a

(06:11):
lesson learned and she couldprobably get more from me of
that call than what she did.
And I hope if she's listening tothis and she goes, ah, you know,
I really felt like I helped him.
I'm really sorry that he didn'tfeel that way.
That's normal, by the way.
That's totally normal when youmiss on this one thing.

(06:33):
But let's go ahead and get pastthat it's not the other person.
It's not the coach.
The coach was not the problem.
Right off the bat, the problemreally rested on my shoulders.
I was the problem.
Let me just right out, get outof the gate.
I was not prepared for thiscall.
I checked my calendar that dayand go, oh, crap.

(06:56):
I got a coaching call.
And I knew it wasn't with myregular coach.
I knew it was with thesubstitute coach.
And so I, right out of the gate,wasn't necessarily prepared or
here, let's just be honest.
I wasn't prepared for the call.
And as I started to try to prepfor the call, I couldn't even

(07:16):
remember what I wanted to beheld accountable for.
Like there was enough going onin my life and there still is,
but there was enough going on inmy life that really, I just was
in a place where I I'm justtrying to take it day by day.
I really don't have these goalsthat are way out in front of me.
It's how do I take one step at atime?

(07:38):
And so when I got on the call, Ididn't even remember prior to
what I was being heldaccountable for, which this
person really needed to know toproperly coach me.
I had what I like to call anEeyore mentality.
Eeyore is a character in Winniethe Pooh.
He's the donkey that's, hey, youguys, right?

(08:00):
Like he has always thatdowntrodden negative mindset
that bad things happen to him.
I was in that kind of mood andattitude.
And so it's something wheresomebody that's meeting you for
the first time and you come withthat type of attitude, it also
can be somewhat off-putting.

(08:21):
And so going through this call,I started to do what I normally
do in every coaching call.
My coach taught me this, beopen.
No one can help you if you'renot open.
What do you need?
What is going on?
Open up.
If you're just like, Oh,everything's all right.

(08:42):
You know, it's just what it is.
You're not going to get the mostout of it.
If you're, unless you are, Hey,this is what's happening.
This is why it's happening.
This is what's going on.
And now I need to see aroundthis corner to get to my goal.
I mean, the more open you are,the better a coach can help you
because they can't get in yourmind and know what you're

(09:03):
thinking.
And so already we were headingtowards disaster just from the
start.
Partway through the call, Irealized where I was at.
So I had a lack of preparation.
I also had a lack of preparationwhen it came to the location of
where I was going to be coached.

(09:23):
This is a point that you shouldwrite down when you are going to
be coached.
Make sure you're in a place thatyou can be open, by the way,
because if you're not open, thecoach can't help you.
And if you can't be open whereyou're at, then you're already,
again, setting yourself up forfailure.

(09:44):
And so halfway through the call,I realized that I might not be
alone in this conversation thatactually where I was sitting and
doing the conversation, thewalls were extremely thin and
somebody was in the next room.
And so it was something whereall of a sudden I started to
shut down.
And that's why I said this call,probably the coaching call could

(10:06):
have ended 10 minutes earlybecause I started to shut down.
I started to just agree witheverything the coach was saying
and worked to try to get her offthe phone as quickly as
possible.
So where's the lesson?
Where's the empowerment?
What was missing?
And I know we're already wellinto this podcast and you might
be wondering, okay, what wasreally missing and what was

(10:29):
missing out of the entirecoaching call that would have
changed it from the worst of alltime was the gift of listening.
That's right.
Listening.
Now, We might have anunderstanding of what that is,
but let me really break it downand define it of what I mean by

(10:50):
listening.
Because as leaders, we need tohave this gift.
We need to provide this gift toour people.
And if we don't, they will notfeel served.
They will not feel valued.
And while conventional wisdomis, We'll tell you that our

(11:13):
people need to listen to us.
They will not emulate unlessthey see it.
We can't have them listen to usif they don't see it from us as
leaders first.
And so the first point oflistening, the first definition
point, and it's the mostimportant.

(11:34):
If you get nothing out of thispodcast episode, here's the
number one point that you needto to adhere to.
There's no, there's no debate.
If you do not have this, you arenot giving the gift of
listening.
Now, the other ones, they willhelp you.
They will take you to the nextlevel, but they will not get you

(11:56):
to the place of where peoplewill actually feel like you're
listening to them.
If you don't have this oneelement, which is very simple,
you need to be present in theconversation.
It's really funny in this, eraof life that we live in, the act

(12:16):
of presence, which used to becommonplace, is actually
becoming more and more unique.
See, with the advent oftechnology, our attention can be
robbed within a second.
Our attention can be removedfrom a conversation within a

(12:36):
moment.
And how does that happen?
With a simple notification.
A simple ding, a ping, some sortof buzz, whether it's on your
phone, your watch, your computerscreen, there's all sorts of
places where notifications canhit you.
And it can be so easy as aleader to be present in a

(13:00):
conversation one moment and gonethe next, even though physically
you're there, even though you'retrying to listen.
You can rob that person the giftof listening within a moment.
Not a second, a moment.
I mean, it is so quick how itcan be robbed.

(13:21):
But the non-negotiable is youhave to be present.
I have a hard and fast rule thatwhenever I'm training, I'm
teaching, whenever I'm reallyconsulting, my cell phone is
always put away.
And it's on do not disturb orwork mode.
So that way it doesn't bother meon my watch.
It doesn't come up on mycomputer screen.

(13:42):
I always want to put my cellphone away.
I don't want it on the table.
I don't want it on the desk.
I don't want it in the room thatI'm at.
Really, honestly, I want my cellphone so far away from me.
Now that can create someawkwardness when I have to look
something up when I'm talking tosomebody, but I've really
learned that it might be worthjust writing it down what I need

(14:05):
to look up and getting back tothem without having to go, Oh,
let me grab my phone and we'llfigure it out.
Now there's times where I'llhave to stop the meeting, grab
my phone because I need to looksomething up or they've asked
for me to pull up a text orsomething like that.
And I could totally go do thatand I will do that.
But then I immediately put myphone away again.

(14:25):
And so it's never sitting outfront because again, any
notification, it doesn't matterif it's my phone or their phone,
it actually can rob yourattention span.
And the gift of listeningactually requires attention
because you can't, I mean, youcan hear somebody, you can
somewhat recognize that they'resaying something, but you can't

(14:46):
purely listen to somebody unlessyou give them your full and
undivided attention.
And so it's incredibly importantto be present.
Next, I think one of the otherelements to truly listening is
when you know the answer, not toanswer the answer, but to answer

(15:09):
it with a question.
I always say ask clarifyingquestions to learn.
So even though I may know theanswer to their problem, or I
may know the answer to whatthey're thinking.
I always ask clarifyingquestions to get a little bit

(15:32):
deeper.
And I will tell you why I dothat.
Because when I think I know theanswer, I'm assuming I know the
answer.
And we all know what assumptionsdo.
Because let's say I'm wrong withthat assumption.
Now they don't feel like I'mlistening.
And so you rob them of the giftof listening.

(15:53):
When you ask clarifyingquestions to learn, you can see
with your idea of what youassume is correct, if it truly
is correct or not.
And so I always ask clarifyingquestions as answers.
And when I say clarifyingquestions, it's, do you believe

(16:15):
this?
Or do you think this?
Or do Share with me a little bitmore why you think that way or
why you think that this might bethe answer.
Or that's a really greatquestion.
Let me ask you, what is yourthoughts on it?
I'd be curious to see what youthink.

(16:38):
Because it's something wheresometimes people are asking
questions because they want toknow something or they just want
confirmation that they're right.
I don't know how many timesyou've had a conversation like
this.
I've had a conversation multipletimes like this where I'll say
an answer and they'll go, that'sexactly what I was thinking.
Okay, perfect.
That makes sense now.

(16:59):
And so they already are thinkingof something.
So why not help them?
By asking clarifying questions.
Now, when I've been reallywrong, by the way, with
assumptions, that's when someonegoes, you're not listening to
me.
I don't feel like I'm being I'mbeing heard.
I feel like, you know, thatyou're not present.
You're not connected.
And so instead of trying to playdefense, asking clarifying

(17:24):
questions in a polite manner, bythe way, not again, not like
trying to do it in an aggressiveway.
I mean, don't do it in adefensive way.
Especially if what the person'sbringing forward is something
where they have a problem withyou, with conflict resolution.

(17:45):
You don't want to ask clarifyingquestions in a way that feels
like now they're beinginterrogated.
I would always, when it comes tosomeone having an issue with me,
going, oh, I really apologizethat I made you feel that way.
Or that what I did...
came across that way.

(18:05):
I just want to apologize that Isaid that because hearing it
from you, I can understand orempathize what you're feeling.
May I ask you this man may askby saying this, how would you

(18:27):
get this across to somebodyelse?
Like if this was the desiredresult of, you know, you needed
to, uh, make this change, or ifyou needed to, uh, do something
differently, how would you liketo get it across to somebody
else and listen to what theysay?
Because within there, it doesn'tsound like you're playing D

(18:51):
you're playing defense, butyou're there to learn.
And then once people are, areunderstanding that you are
giving them the gift oflistening, the conflicts result
resolved themselves.
Yeah.
Now, I think it's alwaysimportant that by asking
clarifying questions, you getthem to a place where they're
self-discovering the answers.
But let's say in this coachingcall, and I'll bring back up

(19:14):
this coaching call because init, I didn't actually have the
answers.
There was one point where thecoach said, hey, what do you
think you need to do?
And I said, I don't know.
I have no idea.
I don't know what the next stepsare.
The coach assumed what the nextstep should be.
And that's what they ended thecoaching call on is giving me
action steps of what would fixmy problems.

(19:39):
But I don't think that's the wayof going about it.
Because again, I got off thecall feeling like I wasn't
listened to.
And so if I wasn't getting intoa place of self-discovery,
getting to a place ofunderstanding how to get to the
solution, I think the next stepis to try to get the person to
unpack further.

(20:00):
And I think you do that byclarifying a question of, hey,
Zach, you know, I'm feeling likein this conversation, while I
understand what the problem maybe, I feel like I need to have a
firmer grasp on that.
So can you open up a little bitmore?
And in that moment, if I wouldhave been asked that question,
because I've been ponderingabout this, if I would have been

(20:23):
asked that question, I wouldhave been very honest.
And I would have said, coach,I'm sorry, I cannot Because
where I'm at right now would notallow me to be that open because
I have other people that arelistening that I don't want to
be a part of this conversation.
At that point, then I could, asa coach, respect that and go,
well, it sounds like we're notquite prepared for this coaching

(20:46):
call.
And so here's what I would likefor you to do on our next call
is I would like for you to bebetter prepared.
So I want you to think throughwhat action steps did you commit
to?
Be in a place where you can beopen so I can help you.
And if you need be, please emailme more specifics about your

(21:09):
situation so therefore I cangive you some more insights on
potential action steps that canchange the route that you're
going.
And in that, what you give thatperson is that gift of
listening.
Now again, I don't fault thecoach.
And maybe that last statementmade it sound like I'm faulting
the coach.

(21:29):
I'm not, I'm not at all.
I know because I've been coachedfor so long by multiple people
in multiple different programs.
I know what I needed to do tochange that.
And I did that through myprocess of triage.
But what I learned from it as aleader is that there are times,
and again, I don't have this allfigured out.

(21:51):
I'm going to be the first one totell you.
I don't got this all figuredout.
Actually, this podcast episodeis for me to remember the next
time I don't have it all figuredout.
And so with that being said, Ineed to give the gift of
listening to others because oncethey feel listened, they'll feel

(22:11):
served.
See conventional wisdom as aleader says, Hey, I'm the
leader.
You must listen to me.
But I would rather now flip thaton the head and say, Hey, I'm
going to listen to you.
And because I listened to you, Iexpect the same respect back.
And I know that if I show youthe proper way of being a leader

(22:32):
of, of being someone thatlistens, that connects, that
cares that you will start toconnect and care.
This is one of the most powerfulgifts that we can give somebody
else.
And I hope as a leader, thisepisode has been extremely
helpful for you.
I hope the next interaction withan employee, a client, whoever

(22:56):
that might be, that you put thiswithin practice.
Because this is the way that youactually become a different
leader.
This is how you do thingsdifferently.
This is how you create adifferent business.
Thank you so much.
Thank you.
Thank you.

(23:40):
Thank you for listening

SPEAKER_00 (23:46):
to the Different Thinking Podcast.
Please follow the show onYouTube, Instagram, and
Facebook.
Don't forget to rate and reviewus.
And remember, today is a greatday for you to apply different
thinking.
Thanks again for listening.
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