Why Most Managers Fail (And What Great Leaders Actually Do)

A Conversation with Dave Kline

May 31, 2025

“Build and run systems that create sustainable excellence. That’s the job.” — Dave Kline

That line hit me like a brick.

Dave Kline is not your average leadership “guru.” His resume spans Moody’s, Bridgewater, and now co-leading The Management Playbook, a platform teaching modern leadership rooted in experience, clarity, and systems thinking.

I sat down with Dave for a candid conversation on what great leadership looks like in 2025—and what many of us are still getting wrong. This conversation made me rethink not just how I manage my Chick-fil-A team, but how I define leadership entirely.

The False Divide: Why “Leader vs. Manager” is Holding Us Back

“People talk about the difference between management and leadership like it's real. It’s mostly bad managers rationalizing not being good leaders.”

In Dave’s view, there’s no longer space to separate the two.

Managers must build and operate systems that deliver excellence.
Leaders must set direction, build trust, and rally people toward a shared future.

Most organizations get into trouble because they have one without the other:

Systems but no direction = bureaucracy
Direction but no systems = burnout

👉 Takeaway: Modern leaders must be charismatic AND systematic. If you’re only one, you’re holding your team back.

The AI Tipping Point: You Now Manage Machines Too

“The manager of the future is an organizational engineer. You don’t just manage people—you manage people, AIs, systems, and how they all work together.”

Dave and I both agreed: AI is no longer optional or niche—it’s now table stakes.

I told Dave how I’ve started giving AIs to my leaders instead of hiring new admins. His reaction?

“That’s not fringe. That’s the new standard. You need to prove AI can’t do something before hiring a human to do it.”

But AI doesn’t make humans obsolete—it elevates the value of human interaction. With less admin, leaders must spend more time face-to-face. And that’s where trust, expectations, and emotional intelligence matter more than ever.

👉 Takeaway: Stop thinking about AI as a tool. Start thinking of it as a team member—and reallocate your energy toward connection, clarity, and coaching.

Feedback Is Broken Without Expectations

Accountability issues? Chances are, it’s not a “people problem.”

“Most accountability issues come down to misaligned expectations. If we’ve both written and agreed to what success looks like, then feedback becomes objective. It’s just two people staring at the scoreboard.”

The goal is to make feedback less emotional and more directional. That only happens if expectations are clear, co-authored, and consistently revisited.

Dave calls this expectation architecture—and it’s the keystone habit behind every strong team.

👉 Action Step:

Co-author role expectations with your team members once a quarter
Review them bi-weekly
Make performance conversations about alignment, not judgment

Dave’s One-Page Leadership Dashboard

This part of the conversation alone is worth its own workshop.

Dave built a repeatable, scalable structure for every manager to track the health of their team using one simple dashboard.

Here's what it includes:

Goals – Are we aligned on what you’re here to accomplish?
Measurement – How will we know you’re winning? (KPIs + qualitative wins/losses)
Problems – Where are you stuck?
Solutions – Are they being developed and driven to completion?
Development – Are you growing as a leader?
People – If you manage others, what’s the state of your team?

“Most high performers want to grow. And if they’re not growing, they’re already mentally preparing their exit.”

Founders Mode vs. Traditional 1-on-1s: It Depends

There’s a growing trend among tech CEOs (like Jensen Huang of Nvidia or Brian Armstrong at Coinbase) to eliminate 1-on-1s. Instead, they use:

Group syncs
Stand-ups
Daily async video updates or massive volumes of email

“These leaders still connect—just in different ways. What they don’t do is skip structure.”

Dave’s advice? Don’t copy headlines. Copy the underlying principle: clarity, consistency, cadence.

If you’re running a business with 15 team members, your 1-on-1s probably still matter. If you’re overseeing hundreds? You better be creating scalable touchpoints.

👉 Takeaway: Use the structure that serves your stage. But never go without some cadence of accountability and support.

The Hiring Playbook: Filter Hard, Interview Deep

This part of the interview got real.

I asked: How do you actually find great people and avoid bad fits—especially when candidates know how to game the system?

Dave gave 3 pillars:

Scare away the wrong people early.
“Your culture should repel as much as it attracts.”
Simulate real work if you can.
“A 3-day project tells you more than 3 interviews.”
Go deep, not wide.
“Pick 3 traits that matter and probe relentlessly.”

We both shared how we do the “anti-pitch” in hiring. I actively talk people out of working at Chick-fil-A Millsboro in the final interview. Why? Because I want only those who say yes after hearing the hard parts.

“Culture is not a vibe. It’s a system. Define it. Design it. Protect it.”