Why Teams Fail: 80% Attrition Exposed with Jon Cheplak

Jon Cheplak told me something this week that changed how I think about leadership forever.

"I can predict when a leader is about to fail," he said. "Not from their numbers or their team size. From their vacation schedule."

"The moment they put someone in place and disappear, the countdown begins."

Jon coaches some of the highest-performing team leaders in North America. He's built teams, scaled organizations, and watched plenty of both succeed and implode. What he shared on this week's podcast about why leaders fail hit me harder than I expected.

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THE LEADERSHIP FANTASY THAT DESTROYS EVERYTHING

"Too many people get into business to do less work," Jon explained on the podcast. "That's their picture of it."

Walk into any business conference and you'll hear the same story repeated like gospel: "I built this team so I could step back and work on the business, not in it."

It sounds sophisticated. It sounds like growth. It sounds like what successful leaders are supposed to say.

But Jon's seen this movie a thousand times. The problem is, it's based on a fundamental misunderstanding of what leadership actually means.

Here's what really happens when leaders "step back" from execution:

Their physical absence sends a clear message: this work isn't important enough for me to do, but it's important enough for you to do. The best people start questioning why they're grinding while leadership is in meetings about meetings. The worst people realize no one with real authority is watching, so standards become optional.

I know a sales leader who went from being the top performer to managing a team of 20. He immediately delegated all the selling and spent his days reviewing reports and attending internal strategy sessions. Within six months, his team's performance had dropped 40%, his pipeline was empty, and he couldn't understand why his previously successful approach wasn't translating to leadership.

The answer was simple: he stopped doing the thing that made him credible and started doing things he was mediocre at. His team stopped following him because he stopped leading by example.

WHY THE BEST LEADERS NEVER REALLY STEP BACK

The successful leaders Jon works with? They're doing more work than ever.

"You look at what you're doing," he told me, "you're doing the activities today that you did as a team leader."

They're executing the same daily fundamentals they did as individual contributors, just at a higher level. Not because they have to be, not because they can't afford good people, but because they learned something most leaders never figure out.

Your physical presence in the fundamentals isn't just about getting work done. It's about setting the standard for what matters.

When your team sees you doing the work you're asking them to do, it creates something most leaders spend years trying to build artificially: credibility.

This isn't about micromanaging.

It's about understanding that leadership is modeling, not just directing.

The moment you remove yourself from the core activities that drive results, you lose the moral authority to demand excellence from others.

I learned this from watching a real estate team leader who closed more deals than any of his agents while managing a team of 50.

When he asked his agents to make 100 calls a day, they knew he was making 100 calls a day.

When he talked about follow-up, they'd seen him follow up.

When he set standards for client service, he was demonstrating those standards daily.

The result wasn't just better performance—it was unshakeable loyalty. His team had the lowest attrition rate in the industry because they respected a leader who was willing to do what he asked them to do.

THE PSYCHOLOGY BEHIND WHY THIS WORKS

Jon pointed out something in our conversation that completely reframed how I think about team dynamics:

"When the leader is out there having the experience, their agents' activities lift up."

There's something powerful that happens when leaders stay engaged in execution that goes beyond just getting things done. It taps into basic human psychology about respect and credibility.

As Jon put it during the podcast: "You're asking me to do hard and you're sitting back there not doing the hard."

Think about the leaders you've respected most in your career. Chances are, they weren't the ones hiding in corner offices making strategic pronouncements.

They were the ones rolling up their sleeves when things got difficult, solving problems alongside their team, and demonstrating rather than just delegating.

This creates what I call "earned authority":

The kind of leadership that doesn't come from a title but from proven competence.

When someone has earned authority, their team doesn't follow them because they have to. They follow because they want to.

The opposite is also true. When leaders delegate all execution and focus only on high-level strategy, they often develop "hollow authority"—leadership that exists only on paper.

Their team complies but doesn't commit. They get mediocre effort because they're providing mediocre leadership.

THE EXPENSIVE LESSON ABOUT SMART DELEGATION

Here's what nobody tells you about delegation: most leaders delegate the wrong things. They delegate the activities that made them successful while keeping the meetings, reports, and administrative work that doesn't move the needle.

Smart delegation isn't about getting rid of work you don't want to do. It's about multiplying your impact on the things that matter most. Your team doesn't need you to have all the answers—they need to see you doing the work that matters.

When you're willing to make the calls you're asking them to make, handle the difficult customers you're asking them to handle, and solve the problems you're asking them to solve, everything changes. Not because you're doing their job for them, but because you've earned the credibility to hold them to a standard.

The best leaders I know are ruthlessly selective about where they spend their time:

• A restaurant owner who stays involved in food quality and customer experience while delegating inventory and scheduling

• A software CEO who stays close to product development and customer feedback while delegating HR and legal

• An agency founder who remains engaged in client relationships and creative direction while delegating operations and finance

They understand something most leaders miss: strategy without execution is just planning, and planning without involvement is just hoping.

THE INVISIBLE COST OF STEPPING BACK

What happens when leaders remove themselves from day-to-day operations isn't just about productivity—it's about culture.

Culture isn't created in meetings or documented in handbooks. It's reinforced through daily actions and decisions.

When the person who created the culture stops demonstrating it, the culture starts dying.

I've seen companies lose their competitive edge not because they lacked strategy, but because the leader who built their reputation for excellence thought excellence would maintain itself.

It doesn't.

Standards only stay high when someone with authority is actively maintaining them.

Values only matter when leadership visibly lives them.

Culture only thrives when it's constantly reinforced by the person at the top.

The warning signs you've stepped back too much:

Your best people are having conversations about problems you don't even know exist. Customer complaints are reaching you third-hand instead of directly. Your team is making decisions based on what they think you'd want instead of clear standards you've demonstrated.

Most telling of all: when you do step back into execution, you discover gaps everywhere. Processes that seemed solid are full of holes. Standards that seemed clear are being interpreted differently by everyone.

This is the tax of premature delegation—you don't just lose momentum, you lose institutional knowledge about what actually works.

THE NETWORKING TRAP THAT KILLS MOMENTUM

Here's where many leaders go wrong: they confuse networking with leading.

They start spending their days at industry conferences, speaking engagements, and strategic partnerships while their core business suffers from lack of attention.

Don't get me wrong—external relationships matter. But they matter a lot less than internal execution.

I know a founder who became so focused on being seen as a thought leader that he stopped leading his actual team.

He was getting invited to podcasts and panels while his company was bleeding talent and losing market share.

When he finally realized what was happening and got back to the fundamentals, it took him two years to rebuild what he'd lost in six months of distraction.

The timing trap most leaders fall into:

There's a difference between stepping back because you've built something sustainable and stepping back because you're tired of the work. Most leaders confuse the two.

Real scalability isn't about removing yourself from execution—it's about building systems that amplify your execution. The best leaders I know have learned to scale their involvement, not eliminate it.

They've moved from doing everything themselves to doing the most critical things exceptionally well while building processes around everything else. But they never fully extract themselves from the activities that define their company's competitive advantage.

HOW TO LEAD WITHOUT MICROMANAGING

The key isn't avoiding delegation—it's delegating smart.

Stay involved in the activities that:

• Directly impact your core metrics

• Reinforce your company's values

• Require your specific expertise or relationships

• Set the standard for quality and performance

Delegate everything else.

A manufacturing CEO I know reviews every major quality issue personally—not because he doesn't trust his team, but because quality is their competitive advantage and he wants everyone to know it matters to him.

A marketing agency founder still attends client strategy sessions for their biggest accounts—not because she has to, but because client success is what built their reputation.

A tech startup CEO still interviews every engineer they hire—not because HR can't handle it, but because culture starts with who you bring on the team.

The moment you step back from the fundamentals, you lose the moral authority to demand excellence from others.

WHAT TO DO RIGHT NOW

Look at your calendar from last week.

How much time did you spend on the activities that directly drive your business forward versus meetings about the activities that drive your business forward?

If the ratio feels wrong, fix it.

Pick one fundamental activity that made you successful as an individual contributor and put it back on your daily schedule.

Not because you have to, but because your team needs to see that it matters to you.

Stop confusing:

• Being busy with being productive

• Meetings for progress

• Strategy sessions for leadership

Your business doesn't need another strategist. It needs a leader who's willing to show them what excellence looks like every single day.

THE REAL SECRET ABOUT SUSTAINABLE LEADERSHIP

The leaders who build companies that outlast them aren't the ones who step back the fastest.

They're the ones who stay engaged in the right things for the right reasons while building systems and people around them.

They understand that sustainable leadership isn't about working less—it's about working on what matters most and doing it so well that others want to follow your example.

Ask yourself:

What fundamental activity have you delegated that you should be modeling instead?

What standard have you let slip because you thought someone else would maintain it?

What part of your business needs your direct involvement, not your strategic oversight?

Your team is watching. They're always watching.

The question is: what are you showing them?

Here's to leading from the front,

Leo

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