Episode 52

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Published on:

16th Apr 2025

Diving Deeper With Long Term Clients

Deep Diving with Long-Term Coaching Clients: Maintaining Depth and Challenge

Summary

In this episode of The Coaching Clinic, hosts Angie and John discuss the challenges and strategies for maintaining meaningful and deep engagements with long-term coaching clients.

They explore the importance of ongoing self-reflection for coaches, recognising when sessions become too conversational and ensuring that coaching continues to provide value beyond just emotional support.

Additionally, they talk about handling sensitive topics, balancing patience with the need to challenge clients, and respecting boundaries when clients are not ready to delve into certain areas of their lives.

The episode emphasises the significance of being in tune with clients, listening for what’s unsaid, and sustaining a relationship that fosters growth and trust.

Chapters

00:00 Introduction and Episode Setup

00:42 The Importance of Deep Work with Long-Term Clients

01:41 Challenges and Strategies for Maintaining Depth

02:53 Self-Reflection and Session Evaluation

04:44 Client Stories and Real-Life Examples

07:38 Navigating Sensitive Topics in Coaching

10:46 Holistic Coaching and Life Context

18:59 Handling Resistance and Respecting Boundaries

23:41 Conclusion and Final Thoughts

Want to contact the show? You can leave us a voicemail. It's free to do, and we might feature you on our next episode. All you need to do is go to https://speakpipe.com/thecoachingclinicpodcast and leave us a message.

You can send us a video or voice message on LinkedIn:

John's LinkedIn Profile or go to PresentInfluence.com for coaching enquiries with John

Angie's LinkedIn Profile or visit AngieSpeaks.com

2023 Present Influence Productions The Coaching Clinic 52

Transcript
John:

Angie,

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Angie: John

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John: do you think of

yourself as a digger?

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Angie: of you, of course.

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I absolutely dig you.

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John: Of course you do.

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But that's not where I'm

think heading with this.

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So we know how important it's to deep

dive with clients, but how do you

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keep that going with someone who's

a bit more long term as a client?

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Angie: Oh, in the sessions.

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That, my dear, is probably a

great topic for today's episode.

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John: Yeah, I agree.

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Shall we do it?

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Angie: Absolutely.

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Let's dig into this.

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John: So what happens when you've had

someone as a client for a long time

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and you want to make sure that you keep

going, doing the deep work with them?

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Angie: Yeah, I think it's something that

a lot of coaches don't really think about.

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If you're newer to coaching, you're

not even worried about that yet.

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It hasn't even shown up on your radar.

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But for me as an experienced coach,

I had clients that I've worked with

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for years and years, and I think

that it's just that idea, right?

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Once you get past the surface

the superficial things, and that

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could take, so many sessions.

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It's not oh, we got past

that in session one.

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I think that a lot of people

struggle to still find the nuggets

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because that's what they become.

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You, I think you start out with

these bigger rocks, boulders even

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maybe, but once you're you've been

doing it for a minute it becomes, oh

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wait, where are we going with this?

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How do we keep going?

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How do we keep bringing that?

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John: Yeah I feel like it's easier in

some ways to do the deep dives with

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a longer running client unless you've

fallen into bad habits where you

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haven't been doing that or where you've

maybe had a long period of not doing

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that and perhaps it has fallen into,

okay, don't say this to judge anyone.

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'cause I think I've done it

myself, almost certain I have.

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Angie: Sure.

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John: But it ends up falling into more

conversational, almost like they're paying

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to have a phone call with a friend each

week, which if that's what they want

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to get out of it, then no, no problem.

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But it's probably not, we couldn't

really call that coaching.

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It's more maybe emotional support,

perhaps even counseling to that degree.

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Or paid a paid

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friendship, which isn't really what

we're, isn't really what we're about.

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But in, for the most part, you've already

done the work on getting deep with them.

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You should be easier to take them

to those places because the trust

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is already there and to go deeper.

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You haven't been doing those things,

it's probably better to approach it

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from the way you would with a new

client to start reestablishing that.

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The same methodologies to get you back

into that habit of being able to go deeper

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with them and challenge them a bit more.

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Angie: Yeah, I think that's a great idea.

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I think the whole thing is in order to

be able to do it, I think you have to be

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much more reflective on your sessions.

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And I'm not saying that you

shouldn't be doing that from the

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beginning, but I feel like in the

beginning, naturally and organically.

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More information is there for

you to decipher and go through

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and dig into and all of that.

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But I think in terms of approach and

creating a skill set or a habit even, you

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really do you have to be able to evaluate

and ask yourself to what you just said.

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Was this just a friendly conversation?

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Or was I really still digging with them

because I know I, I absolutely know

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several people who are coaches who just

love that it's a comfortable, and we

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talked about this very recently, but it,

they love the comfort of the longevity,

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the familiarity of the relationship.

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And sometimes you get lost in that.

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You forget oh.

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You know what?

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I'm really supposed to

be challenging them.

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How do I do that?

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So I think the first thing is to

always be self-reflective, right?

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As a coach, you're, you should

be able to evaluate the session.

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Looked at it, but you also need to

evaluate yourself and say, what did I

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really do great in this session today?

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Or where could I have gone

deeper when this came up?

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You have to do that as a coach.

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You cannot just go, all right, check

that box, session number 38, done.

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And if you're lucky enough to still

be working with somebody, right?

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You, that's so I think for me, that's

the first step is to do that evaluation.

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Of the session and of you as a

coach, some self-reflection there.

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Why are you laughing?

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John: I just wanna tell you something

about, there, there was a client I

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had for, at, at least 10 years as

a client, which is an exceptionally

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long time to have a client for not

the only client that I've had for

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that sort of time period as well.

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But pretty much every session was just

him telling me what he's been up to.

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Angie: Okay.

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John: Yeah, so it really was the case.

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So it wasn't like that.

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That's just how we run the sessions.

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It was me saying to him early on.

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What do you actually want

to get outta these sessions?

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His words to me were I was told

I need to have a coach to be

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successful, so you're my coach.

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Okay, but that's really, we need to

actually do some coaching as well.

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And he's look, all I really want to do

is come in and check, check in with you,

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tell you open up to and make my plans

and make my commitments and that's it.

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I'm like, okay, it's super easy, but.

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I could honestly say we never

went deep on those calls.

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We never went deep about anything,

but that's what he wanted.

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And to, to a degree I'm in my head is

if that's what you are paying for and

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that's what you really want to get and

you are finding some value to this.

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Okay.

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It's not really what I want

to be doing as a coach.

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Not one of my favorite coaching

experiences, as it were, but super easy.

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And it was like, all right, I'll

just, yeah, I'll take your money.

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But it's probably not what we want.

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Angie: I

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was, we

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John: not what we want won.

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Angie: I'll take your money.

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John: It is probably not what you

really want in a coaching relationship.

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It's not that fulfilling for you

as coaching work even if, even if

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they're paying you for the privilege.

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It was just very easy to do that and

it's if I'd have said, I don't really

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wanna coach like that, he would've

just been assigned to another coach.

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Angie: Yeah.

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to your

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John: it is with sometimes

in the coaching companies.

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Angie: it definitely is.

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And to John's point on that

though, just by the way.

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You know what?

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Sometimes when you get on with a client,

they wanna give you the rundown they want

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to because that's their brain dump, right?

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So sometimes they get on and I

will allow, Hey, how was your week?

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What went on this week?

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I will ask that question.

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Not because I'm like, Hey, how are you?

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Like, how's the kitten?

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Maybe, sorry if they have

like animals in somebody.

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I actually had somebody recently

whose animal got sick, and

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I'm like, how's the property?

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And so of course they checked in.

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But point that I'm making is, you

wanna be able to do that, give them

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an opportunity to let that stuff

go because there's nuggets in it.

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But I also put parameters,

I do not let that go on for

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more than about five minutes.

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And then I might say, okay, so John,

let me ask you, and then, maybe

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piggyback from something that came

up in a previous session, or, your

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wife irked you or you were sick.

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How's your energy?

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What are you doing?

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It's not just how are you, it's, oh,

so you were really sick with the flu.

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What are you doing for self-care?

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You have to be able as a coach to

take almost any situation and inject.

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Coaching into it, but of course not

to the point of nauseam either where

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somebody's are you like, hello?

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I am still human.

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But I think the other differentiation

is I think there needs to be patience

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because I think in the beginning

of the relationship, as long as

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you're not just there to take their

money, like John, no one's tea.

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I'm only kidding.

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I am only kidding.

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That will be a deleted part of this.

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I'm sure that will not make it to

air, however, I'm just kidding.

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But the point is.

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I think that in the beginning there's

naturally so much more that you

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don't have to do the search, but

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There's a lot there.

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But as you progress it, it gets

like how do I wanna articulate this?

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You have to be patient as a coach

as well, and understand that as time

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progresses and the deeper you go,

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you're not always going to find the

nuggets as easily, which is why it's

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so important to keep digging, right?

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So you may not have in the

beginning they may have these

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aha moments every, every session.

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Maybe great for you if that

happens, but I'm not saying

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that's true.

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That

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John: I would,

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Angie: what.

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John: yeah, I would never set up

a coaching relationship now that

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that would allow that to go on.

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This is very much coaching clients being

assigned to your situation, and you pretty

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much have to give them what they want.

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But for my own business, for my own

clients, that's not gonna happen.

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Because they're gonna be selected and

and we're gonna have done discovery

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before, before we ever get to that point.

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But when you've been even, and then

when you've been working with someone

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a bunch of times, one of the things

that does make it easier, I think, is

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that it's easier to challenge because

they're, they expect it of you and

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the permission's become implicit.

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You probably do reach a point where

you don't, where you don't need to

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keep asking for permission to, to

challenge them or call them out.

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You can just do it and

be comfortable with it.

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Angie: Oh yeah.

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Listen, when you and I have conversations

right, and we, John and I have certainly

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developed a friendship and a relationship

and an understanding of each other.

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Then sometimes at left field, he'd be

like what are you gonna do about that?

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And I'm like, you're coaching me.

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So it is that familiarity where

you sometimes as the client, they

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don't expect it to, that's it's

not, they don't realize it's coming.

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But even as a friend, John still keeps

that mindset of who he is, right?

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And we'll come out and

say hey, what about this?

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And call me out and say, oh, I

didn't even really think about that.

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Because it's just naturally who he is.

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But as a coach, if you're, if you do have

the benefit of that relationship and that

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being familiar, you should absolutely

be more in tune to them so that you can

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listen for what's also not being said.

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I think that's another great

opportunity with longevity is

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because you become familiar enough.

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You can say, wait a minute,

something is missing here.

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Let me go to that.

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'cause we didn't even talk about it, but

I feel like it's hiding here somewhere.

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So you actually have to be more aware too.

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You have to be much more in

tune to get to that point.

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John: I think so, and I think you also

need to know whether they have complete

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life areas that they really don't pay or

seem to pay attention to, or don't want

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to touch on in the coaching sessions.

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As coaches, we should pretty well

know our wheel of life, right?

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We know what the main categories

are for working with clients.

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The main life areas are

in life coaching at least.

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And even if we're a business

coach, we prob we probably

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should know what they are.

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Because coaching does have.

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All these holistic elements to it.

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If there's a really key element of

somebody's life that they're just

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not even willing to bring up, or you

try and su subtlely bring it up and

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they try and steer the conversation

away, you do have to gauge whether

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it is your job to dig deeper on that.

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And probably do need to ask, is

this something you just don't

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want to talk about with me?

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Or is there something going on here

that maybe we should talk about?

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Angie: yeah.

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Listen, I think that's really important

too, is it's, we're talking about your

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leadership or we're talking about.

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You know how you behave at

home or whatever, and you do.

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As a coach, you have to be able

to have some kind of bird's eye

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viewpoint of them very early on.

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I don't know if you do this, John, but I

do ask them about family and things like,

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so tell me a little bit about you now.

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Tell me, let's be personal

for a good 15 minutes.

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Are you married, divorced?

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Children, where do you live?

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And I have their addresses,

obviously, if their clients

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already, but, so tell me about that.

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And I even ask them sometimes

about their home, like, how do

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you like, feel about your home?

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Do you love and again, sounds

a little what do you care?

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I'm here for leadership.

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What do you care about my house?

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But I look to gain as much of a

visualization of their entire world.

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As I possibly can in the beginning

so that I'm visually seeing it.

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I work that way.

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I'm very visual, so I'm always

looking at things in that way.

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But I think it's a good point that,

it's what they say about working out.

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I don't know.

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Like you can't, what is it?

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You can't focus on one muscle

and think it's gonna work.

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Like you can't oh, I

can't remember what it is.

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Probably shouldn't have brought it up.

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John: You probably shouldn't have

because my mind's going to places that

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I can't talk about on the podcast, but.

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Angie: Good morning.

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John: Good morning.

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Look, I think I don't, I dunno where

the workout analogy is going, but I

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do think that the categories of our

life are not so compartmentalized that

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they don't bleed over into each other.

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They do.

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Life is life is a big, messy

whole that we can categorize, but.

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This is a general coaching principle

you may have heard before, probably

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that if most parts of your life are

actually pretty good or even amazing,

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but one part of your life, one key

life area of yours sucks, you are gonna

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feel like crap because of that, because

it will bring everything else down.

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It will bring you down that you've got

this one area of your life that you

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just can't seem to get a handle of.

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I think I used to, early years

ago, used to use the example

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of Madonna on coaching calls.

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Like so successful in all these big

areas of her life, so successful

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in all these areas of her life.

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But relationships for Madonna always

seemed to be a big problem and

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something that, you know, no matter how

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Angie: Maybe you should

upgrade that to J-Lo.

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John: We could take our pick of

celebrities that seem to have

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relationship issues, right?

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Angie: Just I

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John: This is the thing of even if you

are mega multimillion selling artist and

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world famous, and life looks like success

on every level, but your relationships

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suck, it's gonna make you feel like crap.

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And you're gonna feel like there's

one thing that's missing from your

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life that you just can't get a

handle on and it makes everything

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else feel like crap as well.

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So we wanna have all areas of our life

being as good as possible, which means

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we need to pay attention to all of these

different areas of our lives as well.

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And that, so we need to have the context

and that's kinda what you're saying.

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We need to have the context of

what is going on for you at home?

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What is going on for you at work?

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Tell me a bit about, who's around and

what's around you and all those things.

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It gives us more, it gives us more

context to work with the life that you

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are in, that living, rather than just the

words that you tell us for what what you

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wanna talk about on your coaching call.

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Angie: Yeah.

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Did you ever have that happen?

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Did you ever work with a client for

a, like an extended period of time?

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Somewhere.

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Again, I'm going to, I know why 30 eight's

coming up today, but somewhere in session

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38, they say something like, I don't know.

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I had a few different situations happen.

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I'll use a very extreme one where a

client shared that they had lost a child

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and I'm, I literally was so dumbstruck

by the statement and it was so matter

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of fact when I lost my son and I was

like literally the screeching halts.

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In my mind and I said whoa.

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Pause there for a minute.

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Because I was feeling all the feels right.

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I was like, wait, what?

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What did they just say?

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And I needed clarification because I

wanted to make sure that, the loss of

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the child was actually what I thought.

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And so I was like, I'm

sorry, can you repeat that?

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And they sounded so matter of

fact . But I was like blown away.

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They're like, oh yeah, like right before

I started working with you 38 sessions

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ago, which is a long time, by the way.

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Not always within a year.

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Sometimes it takes over a

year to get to that point.

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And I was like, in my head, I was

thinking, where in the heck was

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this information in the beginning?

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But I also realize right in that moment,

people don't generally disclose upfront.

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The areas that are the most painful or

sometimes they don't even realize it.

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To your point too, sometimes we don't

realize how affected we actually are

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by the imbalance of happiness and

fulfillment in areas of our life.

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But that was like a pretty big moment.

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And it happened within the last seven

years of me being a coach and it

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was still a very eye-opening, like

conversation or even a, experience because

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I, they didn't wanna talk about it.

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And I said, I'm going to respect that.

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For today.

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That's what I said for today, because

I'm sure they didn't mean to say

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it because it had been the secret,

but it became a huge part of which

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I saw things so much more clearly.

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I was like, oh.

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That makes sense, but so did you ever

have that happen where something came

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up and obviously maybe not that extreme,

but like you're thinking, where in

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the, was this information in day one?

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John: Yeah.

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Yeah.

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There's one example that comes to

mind, which was a guy was coaching.

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Again, things seemingly

going really well in life.

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Marriage seemed to be going

well, family, all that.

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I.

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Career as a speaker actually

going was going really well.

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I'm not gonna give much

more information than that.

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But not that it would make him, not

that it would make him identifiable,

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but you get a sense to the coach when

there's something, there's something

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underlying that you haven't got to yet.

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And I wouldn't say it took us 38 sessions.

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I think it might have been at least

six, I think it might have been at least

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six months though before we got to this

of of him getting to a point where me

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challenging saying, I feel like there's

something, it's something deeper here.

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And

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he that was around the time he

decided it was the right time for him

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to come out as gay and that he had

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Angie: Oh, okay.

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John: his life.

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So it was a really huge thing it's not

the kind of thing that you really can.

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Push someone, nor should you try

and push someone to come out.

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They have to do it when

they're ready to do it.

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But it's okay to have that sense

and to maybe you'll dig around

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it rather than right at it.

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And we can at least think like an

archeological dig with this, or you

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dig around the artifact that you find

and you start to uncover it, but it's

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still hidden away under a layer of dirt.

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Because it'll be revealed in its own time.

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And you don't wanna interfere with it.

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So that's the thing of that was

a huge leap forward for him.

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Obviously completely transformed his life.

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I think his life was 12

months later I got a message.

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We weren't still working together,

but I got a message from him

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that, his life was really good.

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He was in a relationship with the guy

now, and I don't think the breakout

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with his wife went all that well.

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But yeah

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Angie: listen, it gets messy and

we all fear the messy, and I think

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another point is if you're if you're

actually thinking about how do I do

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this really, how do I really do this

digging that you guys are talking about?

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I think that sometimes you also

not, we always talk about listen

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for what's not being said.

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I think people have gotten that, but

I also pay very close attention when

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they're like, oh, this is great.

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My job is great.

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The kids are great.

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My spouse is great, my health is great.

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I will literally call out

in a very positive way.

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Alright, wait, so let's go to the

spouse or something maybe we haven't

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talked about as often and say,

tell me what's so great about that.

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I'd love to know.

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I'm gonna tell you that has been one

of my like biggest I almost feel like

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it's a hammer, if you're doing a dig,

sometimes you have to use specific tools.

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It's like somebody, working in your mouth

and they went from it's like somebody

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coming and going, oh, I'm using this

dental instrument to all of a sudden

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it feels like a hammer in your mouth.

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It's very extreme and very

scary and uncomfortable.

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But that's the, that is usually a

great segue for me when somebody is

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I asked, so tell me about so tell

me about your marriage and tell me

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about, and they go, oh, it's this, I,

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tell me about

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John: Absolutely that.

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Angie: So you don't have to call

people out in a negative, right?

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John: you're giving me

flashback, flashbacks to my

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dental appointment this morning.

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Uh, so thanks for that.

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Angie: I didn't

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John: no, I.

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I, I wondered if you had been gone

back and listened to my episode on

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toxic positivity that that I did.

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But no I don't, it doesn't

necessarily relate to that.

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I think you're right.

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It's deflection.

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It's like when people are, people

keep making jokes about, or you

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trying to approach a serious topic and

they keep batting it off with humor.

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It's a defense

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mechanism.

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it's a protection mechanism to, because

they don't want you to go there.

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It is.

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It's almost like putting

the sort of warning, warning

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lights outside saying, woo.

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Don't go there.

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Don't go there.

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I'm gonna push you away

every time you try to.

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So if I tell you it's wonderful,

you are not gonna go there.

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'cause it's wonderful.

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And it's you should still go there.

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Like nothing is, nothing in any area

of your life is gonna be so wonderful

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it couldn't be improved upon because

there's always room for growth.

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And if we're not growing in any part of

our lives, we're going the other way.

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We're regressing and entropy

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Angie: Yeah.

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Being stagnant isn't just

as bad as going backwards.

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Absolutely.

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I think, there's this other point

that I, this other piece that I used

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too, and, if somebody, depending on

what it is I had a client who had

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a, an abusive alcoholic partner.

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And very much was like and

just an enabler, 1 0 1, right?

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I was there too, and it turned into

this thing and, oh, you're at a party.

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And it turned into this, and,

but I should know better.

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As soon as I heard that, I knew that it

was like something that was recurring.

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I should have known better.

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And I was like, oh, why?

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Tell me why.

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Why should you have known better?

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'cause when it's happened

in the past, and I'm like.

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Okay.

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Red alert.

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Red alert.

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This flags going up all over the place,

so I knew that in this particular dig,

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I actually had to put the gloves on,

this was going to be very sensitive and

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delicate, and I needed to get the finest

of instruments out to be able to coach

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this person and make sure I wasn't falling

or slipping inadvertently into therapy.

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Which by the way many months later,

I did, convince this person I think

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that this needs to happen because it

was ongoing and it was problematic.

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It wasn't a good situation.

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So anyway, point that I'm

making is, you really do have

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to control your information.

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No one to tread lightly, and I don't know,

did you ever, as a coach John, did you

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ever just stay away from a topic, like

for the whole coaching re relationship,

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John: Yeah.

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Yeah, because when I did try and

broach it, and I think one client in

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particular with this and I do think.

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I do think there were probably issues

around sexuality or sexual identity.

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I'm not necessarily saying

that they were gay or bi.

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That might, it may have actually

been asexuality in this particular

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instance or something like that.

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I don't know a hundred percent,

but relationships was just

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not somewhere he wanted to go.

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And when I did challenge that

in a really nice way, and it was

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just not an area that he wanted

to focus on or talk about at all.

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At least not in intimate relationships.

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Friendship's great, but close, intimate

relationships was not somewhere that,

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that he wanted to go on the calls.

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And so I had to agree that was

the case and that maybe at some

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point it'll come up, but I'm not,

it's not something I'm gonna push.

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Angie: So listen, and I think that to

wrap up the topic, 'cause we've given

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some good tidbits today and some great

practices on how to do it, I also do think

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that, and you know me, I'm very direct.

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I am a digger, but I also know my place.

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I do not have the right as a coach to

intrude where I am actually not welcome,

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and I may not know the reasons why.

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And if I do dig and I do get more

direct and even push a little bit, pull,

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poke, prod, whatever, and I'm still

getting that, that resistance, I need

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to check myself and say, you know what?

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I have to be respectful of this person.

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So there is also a line to

draw for yourself as a coach

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and say, you know what?

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I have to stop.

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This is the place to your

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John: Yeah.

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Look, we're talking about

digging not bulldozing, right?

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We, we do not want to bulldoze, we

don't wanna, we don't wanna push

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them into something that they're not

ready for yet, just 'cause we want

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to coach them or we want to challenge

them or feel like we're doing that.

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It's like you do not have

to be the provocative coach

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on every single situation.

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Sometimes you just have

to allow and create.

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And hold the space for

vulnerability and psychological

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safety so that when they're ready, they

can, and you can lead them towards that.

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So yeah, I think that's

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Angie: And you can leave

it like that with them.

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Mo, you could say, you know what,

when you're ready, we can come back

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to this and you may never be ready.

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Just be respectful and you'll

gain so much more trust with them.

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John: I think so, I think that's a much

healthier coaching relationship to have.

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I'm sure you hope you do too, that's

pretty much it for The Coaching Clinic

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this time and we'll look forward

to seeing you on another episode.

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very soon.

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About the Podcast

The Coaching Clinic
The HEart of Coaching from learning to client sessions, starting to scaling, we've got you covered.
She's direct and he's diplomatic but Angie Besignano and John Ball are both successful coaches with years of coaching experience and very different delivery styles.
Each episode will tackle a different coaching problem from both styles of coaching, with occasional guest coaches and audience interaction. We're going to have some fun digging into your biggest coaching challenges and helping you become an even better coach.

About your hosts

John Ball

Profile picture for John Ball
From former flight attendant to international coach and trainer, on to podcaster and persuasion expert, it's been quite the journey for John.
John has been a lead coach and trainer with the Harv Eker organisation for over 10 years and is currently focused on helping his clients develop their personal presentation skills for media and speaking stages through his coaching business brand Present Influence.
He's the author of the upcoming book Podfluence: How To Build Professional Authority With Podcasts, and host of the Podfluence podcast with over 150 episodes and over 15,000 downloads John is now focused on helping business coaches and speakers to build a following and grow your lead flow and charisma.
You can now also listen to John on The Coaching Clinic podcast with his good friend and colleague Angie Besignano where they are helping coaches create sustainable and successful businesses, and the Try To Stand Up podcast where John is on a personal and professional mission to become funnier on the stage and in his communication.

Angie Besignano

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With early beginnings as an entry-level manager in the sales industry, Angie has spent more than 3 decades building her knowledge and expertise to create her master coaching and speaking brand, AngieSpeaks. After climbing the professional ladder, she started her own company and decided to focus her practice on High Performance Coaching. In doing so, she challenges individuals to elevate and grow, no matter what level they are at currently in their personal or professional lives.
Angie has created a strong following through her “tough” but “pragmatic” approach and challenges her clients to find the space that is holding them back the most. In doing so, their outcomes not only compound, but take root, so that results can be permanent. The tools she provides work in the “real” world and show up in their first interaction.
Angie has an unwavering passion toward the journey that fosters a true transformation for those that work with her. She delivers her content and speaking engagements with an authentic enthusiasm and curiosity that creates trust and rapport, allowing for a heightened experience.