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Do You Really Want to Know? Why CEOs Dodge Honest Feedback
Episode 706 • 30th September 2026 • Scaling Up Business with Bill Gallagher • Bill Gallagher
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Everybody says they want to know how they're doing as a CEO. Then they fill the board with friendly faces, let the team filter the bad news, and cancel coaching when the numbers get ugly.

Bill tells the story of interviewing his own leadership team at the jewelry company he ran for eleven years, and hearing two leaders tell him he was the wrong kind of leader. He explains what he did with that, why it led to a turnaround, and why feedback lands like a verdict when your identity is wrapped up in your role.

Then the prescription: a real scorecard for the CEO that someone else holds you to, anonymous questions to your team, and the discipline to say thank you instead of explaining.

In This Episode

  • Why "how am I doing?" is usually asked in a way that guarantees "great"
  • The Fernando Flores style assessment interview and how to run one
  • Five ways CEOs avoid the truth: no CEO scorecard, a friendly board, a filtering team, skipped coaching, and cancelled quarterly planning
  • Why you know you are a micromanager but not how severe it looks from the other side
  • This week: ask one person an uncomfortable question, then shut up and listen

Host Links

Scaling Up Business Podcast with Bill Gallagher

Transcripts

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I wonder if you really want to know

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how you're doing as a CEO.

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See, everybody says, yes,

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I want to know how I'm doing and

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how I can improve.

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But then the other behaviors and suggests

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that either consciously or unconsciously,

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you probably don't actually want to know.

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So I'm not sure that I believe you

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when you say you want to know.

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Everybody, I'm Bill Gallagher,

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Scaling Coach and host of the Scaling Up

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Business podcast.

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Also author of Busy Is Broken.

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This show comes to you every week with

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tales, stories, that kind of thing.

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This solo episode explores CEO feedback

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and how do we level up as a

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CEO?

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Let me start off with kind of my

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personal story.

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Look,

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I never really liked to know how it

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was, although I said I did.

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The truth is,

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if I talk to you about a problem

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that I was dealing with,

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I used to go to my wife all

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the time complaining about this or that

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with several different companies.

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But I remember one time in particular

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talking about our jewelry business,

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the one she started years ago that I

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came in and ran for eleven years as

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CEO and worked on scaling.

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Anyway, so I'm complaining about,

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I don't know, probably at any given time,

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lots of people, people on my team,

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vendors, partners, customers,

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like all that kind of thing.

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And then Lori would always flip it back

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to me.

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She'd be like,

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here's what's wrong with you.

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Here's what's wrong with you.

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Here's what you're not doing.

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And I would get so mad.

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And I'm like, no, there's a real problem.

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I need to fire those people,

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fix those people.

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discipline those people.

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I need to do something.

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And I just always wanted to focus on

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the other person in whatever the matter

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was, right?

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And every time I'd be having a problem

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and somebody told me it was my fault,

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it'd be very upsetting to me.

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And in general, I don't walk around going,

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what's wrong with me that I have this

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situation in life?

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I go, what's wrong with the other people?

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Now, maybe I'm more arrogant than you,

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right?

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That's definitely a good chance.

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But I know some of you are like

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me,

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and you want to focus on what is

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wrong with everybody else.

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And it's really hard to think that you

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have something to do with it.

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So here's the thing.

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There's definitely issues with other

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people, but my wife, Lori,

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would always flip it to me.

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She's like, yeah,

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maybe there's an issue there,

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but who are you that you hired them,

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kept working with them,

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didn't draw the line with them who are

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you that you created and tolerated this

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situation to get to this breaking point

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and I I think that it's uncomfortable and

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I get defensive and I don't like to

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hear it but I've learned to know that

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the very easiest person for me to work

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on is me

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And while there might be things to do

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with the other people around me, right,

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customer, employee, partner, vendor,

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like whatever,

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there's always then me who created that

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situation.

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So it is ultimately like liberating and

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empowering to realize you and I are the

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ones who created the situation.

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And there are lots of ways of doing

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it.

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So we know the 360 review.

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We know what it is to have a

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coach.

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Hopefully you have had a coach.

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I shared, I started having coaches,

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business coaches in my twenties.

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And this friend of mine,

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Mike Maddock last night at dinner was

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like, oh my God,

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you had a coach in your twenties?

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I'm like, yeah, it was about twenty-five.

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And I started,

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I had another one at twenty-seven.

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So I had at different points.

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business coaches,

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and it was really useful because I could

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just say, tell me what to do next.

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What am I missing?

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Where do I need to go?

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And it made my life a lot easier.

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One of the things that I got coached

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to do was to find out how I'm

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doing as a leader in a deep,

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rich way.

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So a coach can give you feedback.

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You can look at your numbers.

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You can have an advisory group like a

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forum or a Vistage group.

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And you could do a 360 review.

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All of these things are good.

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I actually suggest you do all of them.

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But the other one that we talk about

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in the book Busy Is Broken

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that I did is, um, uh,

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this kind of in-depth rich interview

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assessment from Fernando Flores.

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So Fernando Flores, really interesting,

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um, philosopher, business politician,

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et cetera.

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Uh, and he said,

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we are so focused on like being polite

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and not really telling the honest truth.

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It'd be really great to get a rich,

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like, uh,

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in-depth assessment for people.

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So I got coached by my coach to

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go do a handful of these.

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And I interviewed some of the people on

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the leadership team for the jewelry

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company that I had come in to get

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over that I was running now.

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Um, and it was, it was, uh,

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It was, in moments, uncomfortable.

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And I think a lot of times we

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are afraid to open up this can of

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worms, like start something,

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then have to deal with it.

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But I've always been a good student,

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a good coachee.

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And so I like, you know,

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if I get the assignment,

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I'll do it even and go through the

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uncomfortable places and notice what I

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notice and then share that back with my

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coach, teacher, trainer,

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like whatever it is.

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I went and did a couple of these.

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I probably did four of them on the

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leadership team,

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maybe some of the others in the company.

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And I said, all right,

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how am I doing as a leader?

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I need your feedback for me to lead

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this company effectively,

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and I'm really committed to growing us,

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and I want to know how I'm doing.

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I want your honest opinion.

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I want your, the real truth.

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I don't want you to tell me what

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makes me feel good.

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I really, I'm serious about it.

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I want it.

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It's okay.

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Like anything you say.

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So I spent a moment or two giving

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like rich permission and, and, and,

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and meaning it.

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And then I started with the easy part.

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So this helps to continue to build that.

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Yeah.

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What am I doing that's good?

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Like, what's good about me?

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What's reliable?

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What are my strengths?

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Like, tell me all the good stuff.

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And then I brought curiosity to that.

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Is that really true?

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How do you feel about that?

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Not defensive or deflection or like, yes,

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no, whatever.

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I'm curious.

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Tell me more.

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So now we're into all of it.

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And it's starting to be like, oh,

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they can tell.

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I do actually want to know.

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And we get a bit of it.

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And then after we've got the main points

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and I've kind of probed them a little

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bit and I'm really seeking to understand,

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I'm demonstrating that I seeked out.

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I said, okay,

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let's talk about maybe the things that you

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don't love so much or where I'm missing

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something or like that.

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And then I probe that.

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Messes or upsets.

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weaknesses gaps like talk to me about that

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tell me and again I'm curious and so

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as I'm curious and like bringing more

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curiosity digging into it a little bit now

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more and more is coming out and I'm

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getting more of it along the way two

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of the leaders in particular said to me

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You're the wrong kind of leader.

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We like the old leader, your wife,

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who's the founder of the company.

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And the way she worked with us was

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like this.

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And she did these things and helped us

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in this way.

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And you don't do any of that.

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And I was like, oh, wow,

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that's interesting.

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Yeah, I get that.

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I could see why you'd like that and

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why you miss her in that role.

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And I thought about it for a minute.

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And I thought about, well,

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what should I do with this?

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And then I had this insight.

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I'm forever going to be a disappointment

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to them.

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It's just not in my nature.

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Like I could stretch to do that some

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of the time, but it'd be fake.

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And I have zero commitment to being that

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kind of leader like she was.

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Fine.

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It's a valid kind of style of leadership

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and role as a founder of a company

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to do what she did in that way.

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But I wasn't that and I wasn't going

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to be that.

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And I had a different intention for where

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we were going with the company.

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So in the minute there in the thing,

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I said, you know what,

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I'm probably forever going to be a

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disappointment to you in that because I'm

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never going to be like that.

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And I'm committed to these things and I'm

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going to focus on that.

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And I'm never going to do those things

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that she did.

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And they're fine, good things,

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but they're not the only way to lead.

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And they're definitely not the way that

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I'm going to do it.

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And like, if you need that,

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you're never really going to be happy with

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me.

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And I didn't say you should move on

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or whatever,

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but that is what I was thinking.

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Anyway,

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not long after they both left the company

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and it was somewhat disruptive and good,

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but ultimately actually really good.

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Because I could bring in people who were

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willing and interested to work with the

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company in the way with a leader that

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was going to do what I did.

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And there were good points there, right?

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So I had to actually deal with what

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was there.

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It was uncomfortable.

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I didn't like hearing it.

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And again and again,

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like leaning into the discomfort and

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opening the conversation,

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even though it led to a shift and

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vacancies like upsets,

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like disruption in my leadership team in

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the company,

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ultimately led to good things and a

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turnaround in the business that was

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necessary.

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So here's what it looks like.

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When you do it,

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when you and I do it,

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there's a few things that I see again

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and again.

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The first one is no scorecards for the

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CEO.

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So everybody,

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we go to work on building scorecards and

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you maybe do it through the motions,

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but you never finish yours and nobody else

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uses your scorecard to hold you

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accountable, right?

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You don't.

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say,

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finish and develop your scorecard like you

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do with everybody else on the team,

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and you don't give it to the board

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or to me or your coach or whatever

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and say,

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or even a buddy or your COO and

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say, okay,

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now I want you also to hold me

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accountable for living up to my scorecard.

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um you ask how I'm doing but you

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ask it in a way that guarantees you're

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doing great man you ask it in a

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way that skirts the like in-depth the

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critique um so you ask how am I

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doing or how like things like that and

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but you do it in a way that

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that guarantees you're not gonna get the

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biting comment

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You fill your board,

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whether it's a fiduciary board,

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a controlling board, or an advisory board,

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you fill it with people that are friendly

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to you, that share your point of view,

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and they don't push you and challenge you.

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And you surround yourself with a team that

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filters the bad news.

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They know what's going to trigger you and

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have you lose your cool in the office,

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and they filter it and they make it

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easier and smoother for you.

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You hire a coach,

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but then you cancel sessions with me or

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with your coach when the numbers are ugly,

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when there's a crisis.

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You're like, oh,

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this isn't really a time for the scaling

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up coaching.

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I'm going to go work on this separate.

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You don't bring whatever you're struggling

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with and upset about to the coaching

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conversation.

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You keep that separate.

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The coaching conversation is just for

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doing the big growth things,

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the good news stuff or whatever.

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And you put it on pause.

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You delay it.

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You do whatever.

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And you avoid those kinds of things.

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And even you'll cancel or skip quarterly

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planning.

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I see this all the time.

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Oh, we got a big situation right now.

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We can't do planning.

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This is a really common thing.

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We're going to cancel it.

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Now,

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I don't usually fire clients for doing it.

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It's all too common.

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But I point out that the very...

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significant emergency or thing that you're

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grappling with,

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I actually ought to come into the session

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and we ought to talk about what's like

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wrong with you as a leadership team,

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as a CEO,

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as a company that you're in this

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situation.

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What do we do about it?

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We want to take a long,

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hard look in the mirror and collectively

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look at how we're doing to do it.

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So these are some of the common things

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that I see again and again,

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and you and I both do them.

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So here's why, right?

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Why is that your identity,

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in particular founders and CEOs,

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who you are for yourself is so tied

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to the role that you have.

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It's so all encompassing.

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The feedback that you get lands as a

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verdict, like an indictment on you.

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And not knowing,

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like focusing on something else,

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lets you feel good,

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lets you get through the day and grapple

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with that.

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And feeling good is important,

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like finding a way to feel good enough

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to get your job done.

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And the bigger you go,

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the bigger your company is,

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the more people on your team,

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the layers of your management,

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the less the truth reaches you.

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And ignorance becomes kind of the set

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point.

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And then when things are like whatever,

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the things you don't want to look at,

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you busy yourself, right?

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So busy is broken.

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We don't talk as much about this in

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the book,

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but we will busy ourselves and work on

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things that we enjoy or that we like

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doing, that we're comfortable doing,

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rather than going to the more

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uncomfortable things to look into where it

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is.

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So

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There's a prescription and I want to talk

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to you about like,

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what are some things that you could do

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right now?

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So first of all, develop a scorecard,

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create an actual scorecard with metrics

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and things like that,

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and give it to at least one other

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person to hold you accountable to

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delivering on your role.

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Ask your team anonymous questions.

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What should you stop doing?

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What should you retire?

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Where should you level up as a leader?

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Ask questions like that in anonymous ways

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so that people can give you feedback with

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some safety, right?

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And when the answers come back to you,

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don't get defensive.

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Don't explain it.

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Don't whatever.

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Say, well, thank you.

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Like I did with the leaders on my

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team.

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Thank you so much.

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I am always going to disappoint you.

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You might go and clean it up.

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You might shift something in some way,

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right?

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But notice if you haven't heard something

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that stung, that felt uncomfortable,

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like that was calling you out personally,

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then there's an issue.

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Now, ultimately, the way to shift it,

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right,

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is to create a goal and to go

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to, like in the book,

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I talk about my going to Italy,

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the Italy test.

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There's a whole chapter on that and a

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forcing function that helps.

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But in order to do that and to

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go from where you are today to where

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you need to be with a company that

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doesn't rely on you,

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a team that doesn't rely on you,

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we have to know where you are right

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now.

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You want to know how you live for

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other people.

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And here's the thing I know again and

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again.

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The leaders that I work with,

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you and I, we kind of know, oh,

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I'm a perfectionist.

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Oh, I'm a micromanager.

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You've been it again and again in your

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life, maybe even today,

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and you do it in response to stress

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and pressure and that kind of thing.

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You're like, well,

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I have to be a perfectionist because our

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work matters in that way or whatever,

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like that kind of thing.

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So you know.

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What you don't know is the severity of

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of how it is and you have like

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rationalizations or justifications for how

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it is because I did everybody I work

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with does the same thing well I am

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that way because we have this because it

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really matters because it's life or death

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because it's financial because we have an

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obligation because there's regulatory

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because we're in a time of crisis because

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of look on and on and on you

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have an explanation for why it's not so

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bad and why it's actually a necessary

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behavior on your part

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but you probably have very little

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appreciation of what it's like to be the

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other person, persons dealing with you.

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So you don't know what it looks like,

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how severe it looks from their

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perspective,

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And you don't know what it feels like

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to be them.

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You don't know how bad it is.

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So start this week.

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Ask one person an uncomfortable question.

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Shut up and listen.

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Go read the chapter on the interviews.

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Do some form of that.

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Do the 360.

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If you're in a workshop with me,

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do our live diagnostic,

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but get your team's input after you do

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the personal one.

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And then see the whole thing.

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Get at least three people in that.

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So you get kind of a rich,

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anonymous picture of how you are.

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And that's an opportunity to level up,

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as it's easy for me to say, right?

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So that's your invitation for this week.

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Start to pull out some of the input.

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Then start to upgrade it.

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Keep looking for how you are.

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You could also look at home.

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How am I as a mom or a

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dad, right?

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All really,

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really useful things to begin to look at.

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Hope that's helpful for you.

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Keep watching.

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Keep listening.

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Go read Busy Is Broken if you haven't

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done that.

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And until next time, keep scaling.

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