Episode 89

I'm terrified to coach my best people

If you've ever thought these words, you are not alone — but you might not actually own your business anymore. Dennis Collins, Leah Bumphrey, and Paul Boomer pull a confession from the archives: a founder who is "hostage" to their top revenue-producers. When your busiest people start skipping steps, ignoring training, and hiding sloppiness behind a wall of "momentum," your business is in a state of drift.

We dive into why founders avoid these hard conversations, and the reality that your company's standard is actually defined by the weakest person you allow to stay on staff.

In this episode:

[02:13] The "Busy" Trap — why busy doesn't equal success, and how high activity often hides a lack of efficiency

[04:01] The Hostage Situation — how to reclaim ownership of your business when you're afraid your top earners will quit if criticized

[05:12] Defining Drift — how to tell the difference between true momentum and just "moving fast" away from your core purpose

[31:02] The Abdication of Kindness — why withholding coaching from high performers isn't being "nice," it's an abdication of leadership

Resources Mentioned

The Sales Trust Playbook — a free guide to help founders find clarity and empower their teams. Download it at ConnectAndConvertPodcast.com

Connect With Us

Website: ConnectAndConvertPodcast.com

Got a "true confession" or a question you want us to cover? Email connectandconvert@wizardofads.com

Transcript
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(Music)

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There are founders that think every

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single day things that

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they never say out loud.

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And here we are, Leah and Paul Boomer and

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Dennis, to try to help that, right?

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They're worried about the shortcuts

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they're taking, they're

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worried about their fears.

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They're worried about decisions that

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quietly don't get made.

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So this is Connect and

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Convert, Connect and Convert.

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I'm Dennis here with Leah and Paul.

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We work with business

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owners and business founders.

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We have for decades, I kid that we have

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over 100 years of experience working with

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small business owners,

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97% of those are mine.

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The world was black and white.

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Yes, it was, yeah.

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So what we're sharing is

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a series of confessions.

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Confessions, real confessions, real

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stories of real business

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owners and real founders.

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These come from the archives, right guys?

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We've heard this stuff and now we wanna

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share it because if you're feeling this

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or know someone who is and you can't name

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it, you can't solve it.

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You've gotta name it to solve it.

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So if you're building something that

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matters and I'm sure you are, that your

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business matters to

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you, you're safe here.

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We get you.

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We understand what you're going through

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and we're gonna have a series of

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discussions, confessions, so that you can

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know that you're not alone, okay?

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So here we go.

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Hi guys, ready to go?

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Hello again.

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Let's go.

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I got a confession

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here, boy, I got a good one.

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I'm always waiting for something juicier

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than you have, Dennis.

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Well, I don't know.

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You live down in Florida.

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Come on, I'm up in Canada.

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Cold, wild north.

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We don't get to.

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Well, if you want Florida man

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confessions, that's a different podcast.

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Okay, we can

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do sales confessions.

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Okay, sales confessions.

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Both kind of like me, he's

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in the great Midwest, right?

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Or both sides.

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That I am.

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The great Midwest.

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I worry constantly

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about my busiest people.

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That may sound weird.

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Maybe the techs or the sales people,

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they're crushing the activity.

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They are working hard.

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They are not lazy.

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But the busier they get, the more

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shortcuts they take.

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Okay, how do I know that?

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Because their activity, the high level of

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activity, is hiding sloppiness.

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I can see they're starting to accept more

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excuses for not buying, for not closing.

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They skip steps in our process.

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They tell themselves,

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experience is enough, boss.

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I don't need any more training.

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I don't need any more critique.

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I don't need one on ones.

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I don't need any of that stuff.

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Just let me do my thing.

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I'm beginning to understand for the first

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time in my business life that busy

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doesn't mean success.

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Not necessarily.

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It could, but not necessarily.

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So here's where my biggest fear.

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Okay, let me, let me say this quietly so

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no one can hear my fear.

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Okay.

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These guys

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still bring in a ton of revenue.

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Okay.

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They could be doing better, but they're

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still bringing in a ton of revenue.

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So I'll be honest, my confession.

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I am afraid to coach them.

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I don't want to coach them.

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I don't want to criticize them because

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the minute I start interfering, they're

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going to say, screw you, I'm out of here.

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I'm done.

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But they're leaving

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money on the table guys.

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And yet I'm afraid they'll quit if I

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criticize them and I can't afford to have

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these guys walk out.

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What do you think?

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I don't think you own your business.

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I think they do.

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Oh,

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well, I'm being clear.

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You don't, you, you, as soon as you start

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letting somebody dictate to you how

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things are going and you have a, you're

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that afraid they're going away.

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You,

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you, you are not

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running your business anymore.

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You don't own that.

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They do.

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And you know what?

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If I can figure that out, they have long

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ago figured that out.

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So how do you, all

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right, let's talk about that.

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Paul, any, any input on that?

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I love what you just said, uh, in regards

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to you don't have a business, you know,

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the, the, the, because, because what they

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are doing is they're

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giving them permission

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by not being able to, by not sending in.

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Tell us more.

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It goes into the idea that, you know,

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they might be hitting

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their activity goals.

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They might be hitting, um, they might be

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showing motion and such, but, but what

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steps start getting skipped and as those

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start being skipped more and more, um,

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follow-up gets assumed,

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earned.

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So it looks like momentum,

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but it sounds like

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confidence, but it's actually drift.

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It's drift away from the

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purpose of the business.

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Okay.

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Say it again.

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It looks like momentum.

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It looks like momentum.

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It looks like you're busy.

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You're busy.

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You're doing things and

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it sounds like confidence.

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Yeah, it does.

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It feels confident.

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Doesn't it?

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It feels, it feels great sometimes, but

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you're drifting away from the core of the

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business, from the purpose of the

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business, from what it is that the

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business is really doing

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because.

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But I've seen it.

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I don't want it to

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micromanage or they've earned my trust.

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Exactly.

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You know, yeah.

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And, and this starts much earlier for

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business owners who have tuned in and

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you've only just started

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to scale your business.

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You, you don't have those people that

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have the experience that you're better,

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better reflecting this and,

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and running the show for you.

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This starts early on by you being afraid

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of coaching, being afraid of saying, no,

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this is how we're doing it.

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Being afraid of owning it.

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Afraid.

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Also afraid of to disrupt productivity.

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Well, okay.

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Let me go back to the confession.

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I'm telling my intent

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and sharing that one.

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Yes.

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I am afraid of

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disrupting my revenue stream.

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Okay.

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I could go in there and say, boomer,

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uh, you're not, you're, you're skinnier.

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You're skipping three steps in

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our agreed upon sales process.

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I want you to start immediately putting

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those three steps back into your process.

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Okay.

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And it's for your own good and for the

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good of the company.

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Okay.

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And that guy says,

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well, he's going to

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say one of two things.

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Okey dokey.

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This guy means

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business or I am out of here.

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Yeah.

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I'm not going to work or they're going to

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say Okey dokey and I give a crap.

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Yeah.

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Just say, just to get you

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out of their face, right?

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Yeah.

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Okay.

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So I'm still stuck.

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Uh, my confession

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is real.

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It's happening.

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And I fear losing my revenue stream by,

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by taking action by corrective action.

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They're not going to put up with it.

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They're going to, they, you're right.

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They have me held hostage.

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They, I am hostage.

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Having, having someone work for you,

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owning a business and having staff is a

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lot like being married if you're not

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going to talk, if you're not going to

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have a conversation, if you can't have an

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honest conversation about what's needed,

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what's required, what's wanted, because

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if they're skipping these things, and I'm

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going to assume that previously they were

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doing and following the sales.

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Initially they were.

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So now they've stopped.

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So, so why is it what's going on?

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This is when you're making an assumption.

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Maybe, maybe their spouse is sick.

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Maybe they are really

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toying with the idea of retiring.

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Maybe they need, maybe

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they need an assistant.

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Maybe you know what, being at the office

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at seven 30 is just no longer cutting it.

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We don't know until we talk to people.

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So that's the first step.

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If they're getting close to retiring, I

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would rather know that and be able to

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say, okay, you know what?

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I appreciate everything you're doing,

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which accounts do you want

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to continue looking after?

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What is it that you want to be doing and

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not doing this to them?

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But if they are

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looking at you as being their cash cow,

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I'm going to keep getting this check and

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I'm not really working at the business.

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Do you really want them?

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So does that, does that teach other

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people, um, in the staff on the staff

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that, oh, well, if he's doing this and

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he's getting this, you know, gracious,

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uh, he's able to skip these things

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because of a situation.

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And why am I not getting those?

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I've seen it happen.

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I have absolutely that that

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is absolutely going to happen.

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And as a business owner, you have to be

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expecting that it's going to happen.

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Cause you have to decide

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who's worth hanging on to.

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Why are they worth hanging on to?

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And it again, it all comes down to having

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those conversations with people,

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especially if you've been in business for

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a long time, you might have a whole

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stable full approaching retirement,

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approaching change, approaching.

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Well,

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you know, I think it's a valid point that

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at any point in a person's life, you

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know, you might have four or

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five people who sell for you.

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They're all going through

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something in their life, right?

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Maybe some are close to retirement.

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Maybe some are having problems at home

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that there's always something.

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Am I now supposed to be a psychiatrist?

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Am I supposed to, as the business owner

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now turn into a counselor?

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Because what you're

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saying is applies to everyone.

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We all have something

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going on in our lives.

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That's not related to the business.

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If I own a business, I want to know.

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I do not want to be surprised by the fact

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that my best salesperson is leaving his

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wife and didn't tell me and is struggling

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to keep, you know, struggling to.

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Personal.

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That's what it's affecting.

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It's affecting his, if it's affecting

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what he's doing for me, I need to know

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that I need him to be able

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to tell me if he wants to.

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You can't enforce that.

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Well, again, I have met maybe you guys

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have a lot of people who keep their

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private life private.

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Okay.

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And they don't want to

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mix it with the business.

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And

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how do you deal with that?

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I, Leo, first of all, let me say that

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what you're saying, I endorse that the

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more about my team, the better, but some

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teammates may have a

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boundary and say, that's it.

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That's all I'm going to share.

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But then it's up to me to lead by example

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and come in during the week and say, you

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know what, I'm just so that you're aware,

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struggling a little bit.

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My brother is in hospital and it's kind

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of detracting from what I'm able to do.

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I don't need to write a book about it,

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but they need to know that I

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live a real human life as well.

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So that then when things are not quite

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that great, it's not an excuse.

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I still need them done.

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I'm the business owner.

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Similarly, if I know this other stuff is

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happening for you, at least I know

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because the fear is

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that they're going to quit.

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If you criticize them, well,

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you have to criticize them.

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You're, you're

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leaving money on the table.

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What the hell is going on?

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Wow.

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That Leah, she doesn't even realize that

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I'm going through all this stuff.

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Look, she can't.

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No one's telling her.

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Yeah.

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It's a, it's a, it's kind of

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a vicious circle, isn't it?

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Who talks first?

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I wonder why

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do you have just a

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few, and this is implied.

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So, but I've seen this many, many times

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where there are four or five people who

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are the busiest and not just salespeople,

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but four or five of the

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busiest people in the organization.

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And yet there's 20 other people.

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Why are they the

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busiest four or five people?

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I want to back it up to that question.

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Okay.

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Why is that?

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Let's define our terms.

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Maybe they're hard workers.

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Yes, ma'am.

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Wow.

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Maybe they're hard workers.

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They're hard.

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They have a huge, uh, work ethic.

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Okay.

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They, they, they work

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from morning till night.

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They've been trained that way.

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That's what they do.

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There was a client of mine and they had a

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stellar sales manager.

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She was 10 out of 10 and you just had to

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ask her, she would tell you how good she

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was, but she really was, she really was.

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And she would tell you all

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about her 85 hour work weeks.

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Finally, finally, the owner, the founder

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of the company said, why, why?

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Can't you get your work

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done in a 55 hour work week?

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Really?

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Like, like maybe, maybe you're not that

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good at what you're doing.

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If it's taking you 85, she was, she was

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wearing it like a, she

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was wearing it like a badge.

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And, and boy, did that take the wind out

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of the sails and it validated the other

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people who are not running around like

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chickens with their heads chopped off and

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coming in on Sundays

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and doing all the things.

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So that's, that's interesting.

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That's why we have to

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define what's, what's busy.

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We've all had those people.

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I'm thinking of a guy

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right now who I worked with.

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He was one of my department

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managers, department heads.

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This dude worked harder than any human

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being that I've ever known in my life.

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Okay.

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So his hard work was because he loved

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what he did and he was

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extremely good at it.

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He won a lot of awards doing his work.

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And so what do you say to that guy?

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Don't work so hard.

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That doesn't, that

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doesn't compute with me.

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Can I help you with the process?

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Maybe you have to help them by hiring an

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assistant or giving them

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more time with an assistant.

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No, I tried that.

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He said, screw that.

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I don't need an assistant.

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I know what I'm doing.

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I'm going to do it.

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And I work this hard because I love it.

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I love what I do.

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So is he doing

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everything you need him to do?

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Yeah, he was.

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Good.

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Absolutely.

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Let him go.

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I did.

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Paul, Paul has, has a pause.

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I hear that.

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I hear the wheels all the way.

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Yeah.

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All the way across the, you see the smoke

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coming out of my head.

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There are so many different

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ways to look at this though.

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Yeah, there are.

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Because you, because you, as, as Leah

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said, what is the definition of busy?

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And there are some people who are just

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busy because that's all they know.

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Exactly.

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They've learned in their life.

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That's not necessarily the right thing or

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the wrong thing, but there's something

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there that's deeper.

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What would happen if that person realized

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how many other powers that they actually

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have that they're not yet utilizing?

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Because they're so quote unquote busy

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because they're so

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focused on this one area.

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And I hate the word busy.

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That's interesting.

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I hate being when people

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tell me they're too busy.

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What, what, wait, we're back to an

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important point here.

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Define your terms.

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I like where you guys

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are going with this.

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Um, there's a guy, Steven Covey, you've

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all heard of Steven Covey.

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He, I used him a lot when I was running

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radio stations because I had a lot of

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busy people who were doing, doing things

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that were merely

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urgent, but not important.

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I don't know if you remember the four

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made the square, the four boxes that

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Covey had the Eisenhower square.

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Uh,

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so what I would do, so to your point of

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defining busy, I would ask them the

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question, all right, let's

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look at what you're doing.

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Is it busy work?

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Just urgent stuff that you

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failed to take care of in time.

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So it became urgent or

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is it important stuff?

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Okay.

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That was the first distinction.

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Is it urgent?

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If it's urgent and important, do it.

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Right.

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If it's merely urgent,

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why are you doing it?

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Does that make sense?

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Not what you guys are talking about.

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Define busy.

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Are you just covering your butt because

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you failed to take action two weeks ago

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when it would have been

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just important and not urgent?

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Does that make sense?

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And if you're making your, your sales

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goals, if you're hitting your quotas

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without following the process, then as a

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owner manager, it's up to me to say,

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maybe there's something

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messed up with my process.

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Maybe.

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Cause like, is it

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really like, is he missing?

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Is he actually, or is she missing doing

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something that is critical?

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I thank you for saying that, Leah,

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because that's what I was thinking too.

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It was like, okay, you're going to have a

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salesperson who's just kicking it and not

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following the process.

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Why are they not following?

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And actually this reminds me of a

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conversation I had with my

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wife and my son the other day.

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He doesn't like to wear his Apple watch.

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We have an Apple watch

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on him for many reasons.

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All right.

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But he doesn't wear it.

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So my wife says

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the kid, he just needs to wear it.

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I'm like, no, no, no.

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Why is he not wearing it?

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What is the reason he is, or is not doing

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the thing that we're asking him to do?

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Understanding that first allows you to

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understand, to look back at the sales

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process or whatever it is that you want

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to figure out and

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understand how it works.

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And you might have to adapt and realize,

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Hey, that is an important thing that

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we're not doing as a system.

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That's true.

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So you're saying

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reflect on the process, right?

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Yeah, I'm saying exactly.

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We've got to ask them.

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Ask them why not?

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Yeah.

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Yes.

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Okay.

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Now let me kind of, I'm sorry.

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I'm going to go, go, go, go, go.

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Here's, here's what I'm thinking.

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You know, we're talking about having all

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these conversations, right?

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We're going to have conversations about

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what's bothering you.

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We're going to have a conversation about

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why you're not following the process.

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We're going to have conversations about

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what's going on in your life.

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That's causing you to maybe have to work

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too hard or something.

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Do you know, do you

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realize guys, I'm sure you do.

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You're smart people.

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Most people have no freaking idea how to

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have those difficult conversations.

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Do you realize that they don't know how

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to have this conversation?

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Now the three people on this call, on

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this, uh, episode of connect and convert.

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Sponsored by wizard academy.org.

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Excellent job.

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Well done.

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The, we probably are a little more

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knowledgeable about how to have those

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conversations, and I

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know I'll speak for me.

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If I think what the hell I

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can do that, why can't you?

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That's not fair.

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That's not fair to my managers.

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That's not fair because

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they don't know how to do it.

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And I have made it a part of my life to

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figure out how to do it.

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Okay.

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That drives me crazy.

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Sorry.

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I'm interrupting you.

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I hate, I hate, hate, hate, hate.

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I hate, hate, hate.

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I mean, this job, this is

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what, but I can't do that.

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I don't know how to do that is.

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But it's real, but I hate it.

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It is.

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Hey, Dennis.

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She hates it.

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You can hate it.

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Doesn't make it go away.

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If you are in a position just because you

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don't know how to do something in this

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world of YouTube and connect and convert

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and people who are there to help.

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If you can't figure out how to do

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something, find a resource.

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Then why are you in this position?

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Wow.

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Like that's pretty, are you a driver?

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Right now I am.

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Because, oh, I just can't for heaven's

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sakes, then do something else.

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So can I share with you what happens?

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Okay.

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Okay.

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So let's say that I say

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that to my, one of my managers.

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Okay.

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Get, put your big boy pants on and go

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have that conversation.

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Okay.

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Well, boss, I I'm uncomfortable.

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I don't know.

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I know.

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Just do it anyway.

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Okay.

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You know what happens, Leah?

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Nine times out of 10, they screw it up to

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the point of completely botching an

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already bad situation and possibly

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bringing legal action on to me and my

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company because they said something or

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did something that was illegal.

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Okay.

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I mean, I've had this happen guys.

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And, and, and they take a situation that

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was already bad and they make it worse

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because they don't know how to, they,

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they botched the conversation.

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But that's what happens when you don't do

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those things I said, ask for help.

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Figure out how to do it.

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They're not as smart as you, Leah.

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They don't know where to ask for help.

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Do you see?

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And why are they, and I

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don't want them in that position.

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Wow.

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I'm king of the world.

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If I'm king of the world, then I don't

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want them doing that.

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So they, so on that, so on that note, you

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can go to connect and convert podcast.com

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and then the show notes, you can download

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a little nice, cool thing called the

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founders owners, sales trust playbook.

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Yep.

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Sales trust, trust playbook.

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And tell us what, what is in there

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precisely there, Dennis.

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Precisely.

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Yes.

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We understand that most founders and

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owners were not, did

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not come through sales.

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They came through some skill, some, some

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technical ability that they use to create

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their business and sales

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confuses them, confounds them.

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And they don't know what to do.

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Pick up this playbook.

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There are seven easy to understand, easy

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to read tips that you can read in about

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30 minutes and you can implement one, two

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or three easily in a day or two.

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And that will at least give you some

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traction, some idea of what the owner

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founder should be

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looking at in regards to sales.

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Okay.

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And, and it goes into also what we're

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talking about right now.

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And what Leah just mentioned, maybe that

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person shouldn't be in that position.

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That's true.

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It may be that it's possible,

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but you know, I, being, you know, I

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thought I was the most driver S person

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I'm beginning to wonder, uh, you know,

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here's how I handle it.

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I made it a point that if I, I would not

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ask my management team to do anything

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that I wouldn't do myself.

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Okay.

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So I trained myself and I studied myself.

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Like Leah said, I figured out how to have

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these tough conversations.

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Not everybody has figured that out.

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So I made sure that before I told them to

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go do a tough conversation, they better

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sure as hell know how to do it because

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not knowing how to do it

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puts me in a complete bind.

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Okay.

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Does that make sense?

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You know, you know,

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I mean,

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I, I'm up and you guys know I have a big

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heart and I'm people first, but you do

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sometimes, sometimes this stuff bugs me.

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And Dennis, you might remember where I'm

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remembering this from.

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This would have been back in the eighties

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and it's always haunted.

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I wasn't around.

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When you are building a sales team, when

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you are building your ideal sales team

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and we'll use 10 easy

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math, maybe in Gal here.

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Okay.

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So what you want is on a sales team, you

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want to have three people that are, like

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they are following perfectly.

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They are textbook.

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They are making the calls, the follow up.

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They're writing the thanking notes.

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They are nailing,

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they're nailing their budget.

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Three of them are just

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doing that like clockwork.

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Then you have two that are goal driven.

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They are going to kill that.

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They are, they kill their, their budget.

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They are going to go hard and

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nothing's going to stop them.

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Then you're going to have two outliers

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that drive you crazy.

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They will or won't make budget.

Speaker:

You don't know, but they're going to do

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it in weird ways and you just leave them

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alone because one of them is going to go

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and they're going to make enough that it

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doesn't matter which one of them makes

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budget and which one of them doesn't.

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It's going to help

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your overall team goals.

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But then you have these other three.

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Then you have these other three and

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honestly, they're going to always come

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pretty close to making budget.

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They're going to do everything.

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They're going to come pretty close and

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you're okay with that because frankly, it

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saves the company bonuses.

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It's you don't care.

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You're okay.

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You're okay.

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I want my people to have bonus.

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I want them to have.

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No, but the company doesn't want a

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hundred percent bonuses.

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I did.

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You want to, you want

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about 30% of your team.

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I wanted a hundred percent to get bonus.

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You know what?

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30% of them.

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If they don't, the company

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actually makes more money.

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Well, you just, I don't like that part of

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it, but I do like that your description.

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You just described probably

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every sales team in the world.

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There's going to be a

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stratification, right?

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And you learn that quickly as a sales

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manager that not everybody has created

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equal, but we're not talking about that.

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We're talking about.

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We're talking about people who are

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pushing back who we need to have a tough

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with and we are not doing that

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conversation because we're

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afraid of repercussions, i.e.

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They're going to cost us in sales.

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Okay.

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So we're talking about the not wanting to

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make the discussion because I think that

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having that on your team is

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a reality based on that 10.

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Yeah.

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No, I agree.

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I totally agree with that.

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So not wanting to have the discussion

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that that again is figure it out, man.

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Because if they leave, you're just going

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to have to replace them.

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I love this.

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Leah, we're seeing a side of you that we

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haven't seen before.

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I love it.

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But, but, and I'm sorry, I'm going to

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start wrapping it up just a little bit

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because, you know, it's, it's, we need to

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go from the question isn't about whether

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to intervene with these people.

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It's how early are you willing to protect

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the standard of the organization?

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Absolutely.

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And, and that's a great question.

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But once again, who has the

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responsibility of helping that manager,

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that person, whether it's you or someone

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who works for you, who has the

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responsibility of making sure they can

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have that discussion properly?

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Is it them or you, or

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is it a joint venture?

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It's start from the top.

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Always starts from the top.

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And I always saw it that way, which is

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probably why I sometimes over managed,

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but you know what, I can't send a person

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into a lion's den if they

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don't know how to fight lions.

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Okay.

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I just can't do that.

Speaker:

And the first conversation is about

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gathering information.

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Of course it is.

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Right.

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So that's, that's not the

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hard part of the conversation.

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The hard part of the conversation is

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said, I've gathered my information.

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It's now time for me to tell you what you

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need to do to get in step.

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But if you, that's a hard conversation.

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Okay.

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But any salesman worth keeping knows

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right away as you gather information, you

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start asking me questions.

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Yeah.

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You start asking me hard

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questions about shit I'm not doing.

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I know where this is going.

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Of course you do.

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I know.

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So let's not pretend that the salesperson

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doesn't know they're not doing it.

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Oh, they know.

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And that, that, you know, the supervisor

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does it and that the, oh, let's do it.

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Because.

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Well, they're,

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they're waiting to see Leah.

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How, what, okay.

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How serious are you Leah?

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Yes.

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Paul Dennis, how serious are you?

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Are it, what are the

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consequences for nonperformance?

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That's the first thing

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that goes into their head.

Speaker:

And let me track back to one last item

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that I want to talk about.

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And that is we talked about,

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I think Paul brought it up.

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You have a different conversation with a

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person depending on where

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they are in the hierarchy.

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Uh, let me say this.

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There is no standard in business and any

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small business other than the standard of

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the weakest person you

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allow to be on your staff.

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Okay.

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Why?

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Because everybody knows who the weak

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people are and their mental process says,

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you know what, they're

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going to go before I do.

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So I don't have, first of all, I don't

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have to work too hard because they're

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doing nothing and they're still here.

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So I'll just work here

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and just keep myself level.

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And I know that I have job security.

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They set the standard,

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the lowest performers.

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So to not have a

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conversation with them is malpractice.

Speaker:

You have to, you have to, but what if

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you, you know, again, back circling back,

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what if you don't know?

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And that's, that's where I, that's where

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I maybe differ with you, Leah.

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I would make sure they know how to do it

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before I'd tell them to go in there.

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I'd go, you go with them, but I just, why

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did you put them in that position?

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If they can't actually really sincerely

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want to help their team.

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Cause that's what this is.

Speaker:

That's that's a wrap this up.

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Yeah.

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But that's a complicated question.

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She just asked.

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It is.

Speaker:

It's very, very complicated question.

Speaker:

And I guess the answer to it is you saw

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enough good stuff, right?

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You saw enough good stuff, but, but is

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any higher, I don't know.

Speaker:

I've probably hired a

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thousand people in my life.

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Was every one of them a hundred percent?

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I wish I could say, yeah, hell no.

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They weren't.

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So in

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one sentence, one set on each of you to

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try and wrap up this

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conversation from your point of view.

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Oh boy.

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That's tough.

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You go, Leah.

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If you know, you gotta have the

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conversation, have the conversation,

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start it, start somewhere.

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You're risking more by not having it.

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That's three sentences.

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Yeah, that's all right.

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Now I know I should coach you because you

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know, you did over more than you.

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Dennis.

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Before you have the conversation, make

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sure as Leah always says, define your

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terms, make sure you understand what it

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is you want to come

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from that conversation.

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What, what results do you want to have

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and make sure you know how to, to

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structure a difficult conversation.

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Paul.

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Now you.

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All right.

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For so withholding coaching from the high

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performers isn't kindness.

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It's abdication.

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You nailed it.

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We're done.

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Mike drop.

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Hey guys, we have a theory here at

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connecting convert most founders, most

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business owners, they

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don't need more advice.

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They just need a place for honesty.

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And that's what we do.

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This is your place for honesty.

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Connect and convert.

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We'll see you on the next episode.

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(Inaudible)

About the Podcast

Show artwork for Connect & Convert: The Sales Accelerator Podcast
Connect & Convert: The Sales Accelerator Podcast
Insider Strategies for Small Business Sales Success