Episode 9

full
Published on:

28th Jul 2026

Why Contractors Stay Trapped After Hiring Managers

The primary focus of this podcast episode is the critical distinction between management and mere delegation of titles, emphasizing that a title does not constitute a system. I recount my experience of hiring a manager with the expectation that he would alleviate my workload, only to discover that he inadvertently became a liability, resulting in a regression to my previous role as an operational firefighter. This episode elucidates the paramount importance of establishing genuine accountability within a team, as well as the necessity of managing not just tasks but the efficacy of management itself. We delve into the concept of a corrective action timeline, underscoring the need for swift recognition of issues and prompt corrective measures to maintain operational standards. Ultimately, the discussion advocates for a balanced approach that integrates both empathetic leadership and rigorous accountability, fostering an environment where standards are upheld and team members are genuinely engaged. A profound exploration of management dynamics unveils the critical distinction between mere titles and effective systems within an organization. The speaker reflects on personal experiences with a managerial hire who, despite being well-compensated, failed to alleviate the burdens of operational oversight. Instead of fostering independence within the workforce, the hiring of a manager led to an exacerbation of existing issues, such as declining standards and increasing customer dissatisfaction. This revelation leads to a pivotal understanding: that the mere appointment of a manager does not equate to the establishment of a functional system. The realization that dependency on the owner's presence signifies a lack of true management clarity compels both owners and managers to reassess their engagement strategies. The emphasis is placed on the necessity of creating a management structure that empowers team members and fosters accountability, thereby enhancing overall operational efficacy. The speaker delineates the journey towards refining management practices, ultimately emphasizing that true leadership requires an intentional shift towards building sustainable systems that operate independently of the owner's direct involvement.

Takeaways:

  • A title of manager does not equate to a functional system within a business.
  • Management must focus on accountability, ensuring standards are upheld regardless of presence.
  • Effective management entails addressing root causes rather than merely extinguishing immediate issues.
  • Establishing a rhythm in management fosters a culture of accountability and prevents frustration-induced reactions.

Links referenced in this episode:

Transcript
Speaker A:

I paid a manager really good money to give me my time back.

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And for almost a year, he actually cost me more than anyone else on payroll.

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And I'm kind of laughing about it, but I shouldn't be laughing about it because it wasn't funny.

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And I was supposed to be out of the field, and instead I kept getting dragged back in.

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Same fires like every week.

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And the standards were slipping on jobs, and there was rework, unhappy customers, collections falling behind.

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And I did what most owners do.

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I ran in and put the fire out myself.

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Until I finally admitted the thing that I'd.

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That I'd been avoiding.

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The problem was never really the fires.

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The problem was that I had handed a man a title of manager and called it a system.

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And a title is not a system.

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So here's the standard I want you to hold today.

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If results only hold while.

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While you're there, present on the job site or in the room, whatever.

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You have not built a standard.

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You've built a dependency.

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Welcome to the Contractor Freedom Podcast.

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I'm Jason Phillips.

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If you're tired of feeling trapped by the business you worked so hard to build, you're in the right place.

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As a multimillion dollar contractor and founder of Contractor Freedom, I've learned that freedom comes from mastering yourself and leading others and building systems.

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Each week, I'll help you build a business that serves your life, because the goal isn't to build a bigger prison, is to build a business that creates freedom.

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Welcome to Contractor Freedom.

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Let's go.

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So there's two kinds of people tuning in right now.

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Some of you are the manager running the team yourself, and some of you have managers.

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And, and your job is to make sure that management is actually happening.

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This is for both of you, because the bar is the same either way.

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Here is how you build management that holds when you walk out of the room.

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So let me finish the story that I opened with, because the lesson is buried in how it ended.

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So the production manager paid really well, and the guy was supposed to keep me out of the field, and instead I kept getting pulled back in.

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You know, the fires were landing on my desk instead of on his.

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And, you know, I. I thought that I hired someone to take care of all that for me.

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So, you know, the, the list was.

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It was every week, the standards, the standards were not held on jobs.

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The rework, the unhappy customers, projects slipping on the schedule, collections falling behind, and it just, it just gets a.

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To be a tangled web.

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And so my move every time was, jump in, put it out.

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My you know what, it feels productive, but it's actually a trap.

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And you know, the truth is that I finally faced was this manager was serving his team.

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And he wasn't a bad guy, by the way.

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This manager was serving his team, but he wasn't leading his team.

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He had no real influence over his team or in his team, on his team.

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And he held no one truly accountable.

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And so the decision I had to let him go, but guess what?

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The fires stopped.

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And that's the part that just gets me.

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They just stopped.

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So here's the lesson.

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A title of manager is not a system.

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Serving your team and leading your team are not the same thing.

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And delegating, delegating a title is not delegating ownership.

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So, you know, you get, you get pulled back into firefighting the second that you or your manager stop fixing the actual root cause of, of what's causing the fires in your company.

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You know, and I guess, you know, someone shows up late, someone doesn't follow a process, doesn't check a box, doesn't put down, you know, protect the customer's property, whatever it is, doesn't answer the phone, right, it doesn't matter.

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You have a way of doing things for a reason.

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So, you know, putting out the fires, it feels like leadership, and it feels like you're being superman, but it's actually you subsidizing a standard that nobody's holding.

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So whether you manage the team or you manage the manager, the job is the same.

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Fix the root cause, not just the flare up.

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There's actually three levels of management that I want to talk about today.

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And you know, if a title is not a system, then what is starts with knowing which of the three levels your business is actually running at.

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And the whole game is moving your business up the ladder.

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So here's level one, the bottom.

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The owner is the manager at this point.

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You are the bottleneck.

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You make every decision, you put out every fire, you solve every problem, and every standard runs through you.

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And the goal here is not to stay, it's to manage well enough to build so you can move up, so you can move to the layer above, okay, where you can start owning a business and not just owning a job.

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Now level two, that's the middle.

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And that's when you have managers.

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Actually managing a manager's job is to hold the standard.

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They own the outcomes and they hold the team accountable.

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The tell that you've reached this level is that your presence is no longer the accountability system.

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If things only get done right, when you're around and you have a manager, you don't really have a manager.

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You may have a glorified coordinator.

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If you can leave and the standard stays, you've arrived at level two.

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Now level three.

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Level three is, is a little bit different and it's amazing.

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This is where the, each role actually owns their outcome, whether it's a manager or not.

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And the outcome is tied to their paycheck.

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And the standard holds because the person is invested in it, not because someone's, you know, policing it.

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Incentives and time compensation to results are very important, but they're also, I need to say this, extrinsic external motivators.

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And these external motivators only work when you have the right person aligned in the role.

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Because if you don't have this alignment right, external motivators do not work.

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But when you have the right person and the right KPIs there and the clarity, these, these extrinsic motivators work.

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Okay, so now if you're the, if you're the manager today, if you are the manager, your job is to manage so well that you build the layer above you.

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And, you know, if you already have managers, your job is to keep moving ownership up that ladder and not pull, and not pull it back down.

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Every time that you solve a problem that your manager should have solved, you just move the business back down a rung on that ladder.

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Ownership only goes up when you stop catching it on the way down.

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So the next most important thing is this.

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And this is the most important idea of this whole episode.

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And I call it the corrective action timeline.

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And it's managed by the numbers.

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It's managed by the numbers made concrete.

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And it is the number I use to tell whether management is action actually happening or not.

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Let's, let's build a picture here.

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The moment a standard gets broken, picture a clock starting and two gaps open up.

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Gap one is the time from when the standard is broken to when the manager knows about it now gap two is the time from when the manager knows about it to when the manager takes action to fix it.

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So now picture two companies with the exact same problems, Team A and Team B.

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Team A lets both gaps stretch for weeks, but Team B closes both gaps in a single day.

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Same problems, completely different business.

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Completely, completely different performance.

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Team B is going to way outperform Team A.

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We have to shrink those gaps.

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We have to notice sooner and we have to take action sooner.

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The gap is the whole difference.

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So we have to shorten both.

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So let's talk about the first gap the you know when you notice, how do you find out sooner?

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Well, you inspect what you expect.

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You stop assuming that everything is running smooth just because you haven't heard any bad news.

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You go check on key areas on purpose.

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Okay, if you, if you are managing or leading over managers, okay, you have to inspect what you expect.

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And if you're one of those fast paced leaders, this is going to bite you.

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It's probably already biting you.

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Okay, so review your numbers daily or weekly.

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Not just your numbers that roles, numbers that managers numbers.

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The trend is going to show up in your KPIs before it shows up as a crisis.

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Now where do you want it to show up?

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Do you want it to show up as a crisis or do you want it to just show up as a trend and you can address it?

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So another way is just to set up like automated, automated reports and alerts or you know, so a dashboard gets flagged if there's a deviation in like real time.

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Instead of you finding out after the customer complains or after you've already lost a ton of money or something like that, you know, build.

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Another thing you do is build a feedback loop.

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Customer net promoter scores, nps, you know, employee check ins.

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Let the problem surface early while it's small instead of waiting.

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Now here's the harder one because most managers see the problem and then they just still sit on it.

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So we've got to shorten that second gap by acting sooner.

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And there's three reasons that managers tend to delay actually taking action.

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One, they're too busy.

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Two, they don't know how to handle have the conversation.

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Or three, they're scared of the pushback they're going to get when they have the conversation.

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But here's the problem.

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None of those serve the team.

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Listen to this.

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When you delay, you approve.

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I'm going to say that again.

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When you delay having that conversation, you approve of the behavior.

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And a standard that you don't correct is a standard that you've accepted.

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Let that sink in.

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Let that sink in.

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So you know, whether it's hey, 10 minutes late today, you let it slide in week one, by month three, it's now part of your culture.

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You have to hold new people accountable from day one.

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If you're late the first day of the first week of your job, dude, there's no way I would ever be late the first week of my job.

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You're just, they're on their best behavior the first week.

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So another thing you do, block time for coaching.

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So small issues get handled when they're small, you know, use like a structured model so it's clean every time.

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And how about sbi?

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Situation, behavior and impact.

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So here's what you do.

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You name the situation, you name the behavior, and you name the impact.

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Your objective.

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It's not personal.

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It's not personal.

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Now if you have managers, this is, this is the whole trick.

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So do not inspect the work, inspect the management.

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Don't inspect the work, inspect the management.

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Sit down with your manager and ask two questions.

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How fast did you know about this?

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And how fast did you act?

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The corrective action timeline is the number that tells you whether management is happening.

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You're not measuring the job, you're measuring how fast they close the gap.

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So let's talk about management by rhythm and not by explosion.

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So here's what most contractors, here's what most contractors do in those gaps.

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They only manage when they're already frustrated because they're busy.

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Hey, I get it.

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You're busy, I'm busy, we're all busy.

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But if you're only managing when you're already frustrated, you're not going to do a good job.

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So if you're, if you're, if you're mad and correcting, that's not management.

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That's like, that's an explosion.

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You show up like a hand grenade and blow up on people and hurt people get hit with shrapnel, okay?

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And it teaches your team.

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Here's what it teaches your team.

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They're now, they're now trying to manage your mood instead of hold the standard.

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Think about that.

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Are your people always trying to read your mood when you walk in the door?

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Are they going to get Jekyll or Hyde?

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Are they going to get nice guy or angry guy?

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So you have to replace the mood with a rhythm.

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That means one on ones are actually on the calendar.

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Your team meetings actually happen.

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And performance conversations, they need to follow a process, not a temper.

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So when accountability becomes a cadence, it stops being personal and starts being normal.

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And nobody's bracing for the blow up or the impact because there is no blow up.

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There is a rhythm.

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We have to have a management rhythm.

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You need a management rhythm in your company.

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So here's the formula for the conversation.

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Direct, specific and sooner.

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State the specific behavior result.

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Name the gap of what you expected.

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Hey, here's what I observed, here's what I expected.

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There's a difference.

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What's getting in the way?

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Ask them what's getting in the way.

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And then close with a clear expectation and a timeline on what you expect and ensure they understand what's expected.

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That's the whole formula.

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Courageous conversations build healthy cultures and avoided conversations.

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You know what?

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They build resentful cultures.

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Okay, I've had resentful cultures.

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I have an award winning culture.

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I know the difference.

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One is dragging your company down, holding it back like a ship trying to sail with its anchor on the bottom of the sea.

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And the other is like the wind is in the sails and there's nothing holding it back.

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Great cultures have accountability.

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Okay, now we're going to talk about something different.

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So you're inspecting, you're closing the gap.

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You're having the conversation on a rhythm.

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Someone is still underperforming.

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Here's the one question that tells you what to do about it.

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Ask, is this a can't or a won't?

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Because can't is a skill gap.

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They're willing, they're just not able to do it yet.

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You can coach that.

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If they have a can't, you can coach them so that they can.

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But now won't, on the other hand, is a will gap.

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So you have a skill gap and a will gap.

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Won't is a will gap.

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They're able and they're choosing not to do it.

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This is, that's a character and accountability issue.

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And it usually ends in one of two ways.

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You know the number one management mistake?

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The number one management mistake is coaching a won't like it's a can't.

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You can pour more training into someone, into a willingness problem and wonder why nothing changes.

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So how about this?

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What's the one issue you're dealing with right now?

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Decide what is it?

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Ask that question.

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Is it a can't or won't?

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Because the diagnosis of that is the decision on how you need to handle it.

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Now here's a fear that comes up every time I teach about this.

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This is what I call timely.

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It's the standard and the heart.

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And there's a fear that comes up every time I teach about this, and that is the talk of systems and accountability turns you into a cold leader or cold manager.

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So let me close the loop on that because it's just the opposite.

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The best cultures run a professional standard and genuinely care about people.

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Most companies pick one.

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They're either they're either all about the people and caring about the people or they're all about the standards and the numbers.

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And neither one of those are going to produce great results nor a great culture.

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So that's what I call teamily.

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It's team plus family.

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It's standard and heart at the same time.

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And here's what most people miss.

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Almost everything your people want beyond a paycheck is free.

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Clarity is free.

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Recognition is free.

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Respect is free.

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Knowing where they stand with you and where they're going.

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It costs you nothing but attention.

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Build people up.

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Call them higher.

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Hold the line.

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Those things aren't opposites.

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That is the whole job.

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Lead from the heart.

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Manage by the numbers.

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You don't choose one or the other, you do both.

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So here's everything in one breath.

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A title is not a system.

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Move everything up the ladder.

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Do not catch it on the way down.

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Watch your corrective action.

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Timeline how fast you know how fast you act when you delay, you approve.

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Manage by a rhythm, not by an explosion.

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Ask can't or won't and answer honestly.

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And run the standard and the heart at the same time.

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That is teamily the one move this week.

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So it's two tracks depending on what seat you're in.

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If you are the manager, pick one standard that you've been assuming is holding and go inspect it.

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And if it's broken, correct it the same day.

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Shorten your timeline by one.

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Make it shorter.

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Now if you have managers, sit down with one of them and don't inspect the work.

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Inspect the management.

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Ask you know how fast did this?

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Did you know about this?

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How fast did you act?

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Then hold them to a timeline.

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The standard you walk past, friend is the standard that you accept.

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So this week, don't walk past it.

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If today's episode helped you, don't do this journey alone.

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Join thousands of other contractors inside the Contractor freedom community@contractorfreedomlive.com and start building the business, the team and the life you really want.

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We'll see you next time.

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About the Podcast

Contractor Freedom Podcast
Escape Contractor Prison and Live With Greater Freedom and Purpose
Contractor Freedom is the podcast for growth-minded contractors who are tired of chaos, overwhelm, and feeling trapped by the very business they built.

Hosted by Jason Phillips, owner of the multimillion-dollar Phillips Home Improvements and founder of Contractor Freedom, this show helps contractors break free from “Contractor Prison” through leadership, people, systems, and personal growth.

Each episode delivers real-world insights on building winning teams, creating scalable systems, increasing profitability, improving leadership, strengthening culture, and designing a business that serves your life instead of stealing it.

Whether you’re trying to grow your company, reclaim your time, develop leaders, or simply rediscover your purpose, Contractor Freedom will equip and challenge you to lead at a higher level and live with greater freedom and purpose.

About your host

Profile picture for Jason Phillips

Jason Phillips

Meet Jason Phillips, a visionary entrepreneur who transformed his one-man show into a thriving empire. His journey from struggle to success with a move into roofing and gutters, his company skyrocketed, earning a spot on the Inc 5000 list five years in a row. Overcoming roadblocks, he reinvented the business, achieving astonishing results. Now, he's dedicated to helping other small business owners to break free by helping them foster a team built on trust, faith, teamwork, and excellence. Join him to create "ABLE-Systems" for scalable, repeatable success and customer satisfaction. Don't let mistakes drain you; let Jason guide you to new heights!