How Leadership Coaching Works: A Behind-the-Scenes Look

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Most people think leadership coaching is about learning new skills.
Or becoming accountable.
Or having someone keeping asking you questions until you “discover your own answer.”

I hate to break the news to you, but that’s not how leadership coaching works.

Strap on your seatbelt, because I’m about to tell you how leadership coaching works in reality. And, if you’re lucky, maybe I’ll give you the reasons why it creates longer lasting change than other approaches.

Intrigued?
I thought so.

To understand how leadership coaching works, you have to first start with understanding what it isn’t.
And most people get it wrong.

What Leadership Coaching Is NOT

Here are a few things that leadership coaching is not.

It’s not training. Training teaches you behaviors. If you just try to change behaviors, it won’t last. Coaching, on the other hand, doesn’t simply teach you new behaviors, it exposes the environment you’ve unconsciously built that supports the old, unwelcome behaviors.

It’s not therapy. Therapy helps you understand your identity. That’s great to do, I’m pro-therapy. But without understanding the patterns that are happening now, therapy won’t change anything. Coaching helps you spot the patterns in your identity that create todays problems – and redesign the environment to transform your identity.

It’s not consulting. Consultants talk to you about systems. Systems are great, but they won’t work if it doesn’t address your identity and behaviors. The secret to how leadership coaching works, is that it exposes your leadership blind spots, and all the other things you can’t see from inside your own silo.

It’s not motivational speaking. Let’s be real – you don’t need a pep talk. Oh, if it were only that easy. You need someone who can spot the patterns you’ve been repeating and understand how it is manifesting itself in your behaviors, identity and systems. Once you see those things, the motivational part naturally comes from inside you.

Behavior, identity, systems. Those are the three things you need to know to understand how leadership coaching works.

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How It Actually Works: The Three Phases

Phase 1: Environmental Diagnosis (Weeks 1-4)

What happens:

The first few sessions aren’t about solutions – they’re about diagnosis. You’ll be describing situations that frustrate you and I’m listening for what you’re NOT saying. I’m looking for patterns in your behavior. I’m good at that, because regardless of your position at work, despite whatever challenges you may have – I’ve been there. I know the nuances of what you’re going through. (Check out my story to understand more.)

A lot of this is about the environment you created.

If you tell me your team doesn’t take initiative, I hear: “I’ve unconsciously trained them to wait for my approval.”

If you say your last three hires didn’t work out, I hear: “I’m hiring people who need me to be involved, then complaining they need me to be involved.”

If you explain how everything runs through you, I hear: “I’ve architected a siloed environment where that’s the only option.”

The “Oh Shit, That’s Me” moment:

The thing I like most about how leadership coaching works, is when you suddenly see yourself in a way that you never have before – and it puts your entire life in perspective.

Sometimes this happens in the first call. Usually it happens in session 2 or 3. You’ll be explaining a problem about how this person always does that, or that person always does this… and then I’ll ask you a question about it.

You’ll start giving an answer about how the problem happens every time and, if only…

And then you’ll stop.

Because you just realized what we’ve actually been talking about. You just uncovered the pattern you’ve been running on autopilot. The environment you built without realizing it.

That’s your Unconscious Operating System… and it’s guiding everything you do. You just don’t realize it.

Once you do, that’s when the real growth begins.
And that, my friend, is how leadership coaching works – it creates awareness, not just knowledge.

What you’ll feel:

Exposed. Uncomfortable. Then aware. And then relieved.
And that’s the beginning of how leadership coaching works, but the fun stuff comes next.

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Phase 2: Pattern Recognition and Redesign (Months 2-6)

What happens:

Now we’re working with real situations as they happen. Not case studies or hypotheticals. We talk in real time (when appropriate) about actual decisions you’re making and actual conversations you’re having.

If you have a meeting that goes sideways – we reconstruct it. Yes we’ll talk about what they did, but the more important part of how leadership coaching works is the part that YOU did.

The moment you unconsciously took over.
The question you asked that shut down someone else’s thinking.
The way you “improved” and subtly gave them the message that “your way is wrong.”

If you’re frustrated a project isn’t moving, we look at the environment, your behavior and how that reflects on your identity.

See the pattern?
I thought so.

The caveat:

I’ll challenge you. A lot.
My job isn’t to be a yes-man or to always lift you up on a pedestal.

This isn’t therapy, so I’m not going to spend six months helping you feel better about the problem. That’s not how leadership coaching works, my friend.

I’m going to ask you questions that help you expose all those things cowering in your blind spots that nobody has pointed out to you before. And here’s the crazy thing about that:

Everybody knows what’s wrong with your leadership… except you.
That’s what I do. I hold up the mirror for you to see.

The redesign :

Once you see your patterns, we begin to redesign the environment.

Keep in mind, this isn’t about “delegating better” or “empowering your people.” Those are tactics that operate inside the same broken environment you’ve already created.

This is about architectural changes:

  • How decisions get made
  • How you respond when someone does something differently than you would
  • What you measure and celebrate
  • How you structure projects
  • What behaviors you unconsciously reward, and which ones you dissuade.

We’re not fixing you. We’re rearchitecting the environment you built so there’s room for everyone’s talents to flourish, including yours.

What you’ll feel:

A little uncomfortable, but also increasingly clear. You suddenly notice the problems you’ve struggled with for years start resolving. Not because people changed – because the environment changed. It’s actually quite magical. And, if I’m going to be honest with you (which I am), it’s another part of how leadership coaching works that makes me love my job.

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Phase 3: Integration and Independence (Months 6-12)

What happens:

By this phase, you’re spotting your own patterns before they create problems. You catch yourself taking over a meeting and course-correct in real-time. You redesign projects with greenhouse conditions from the start instead of fixing them later.

Most importantly, you feel like an A-player again, and other people are treating you like it.

The goal of coaching is that you eventually don’t need me. This is the beginning of that process. It may happen quickly or it may happen slower, we’ll figure it out together. Actually, we’ll both feel it when you start flying out on your own.

I’m not a crutch, that’s not how leadership coaching works. I’m a trampoline, allowing you to jump higher on your own.

By this point, you’ll have developed the capability to:

  • See your own patterns
  • Diagnose the environments you’re building
  • Architect conditions where everyone can excel
  • Catch yourself before the pattern runs

What you’ll notice:

Your team operates differently. They make decisions without checking with you. They bring you solutions, not problems. They disagree with you more (which means they’re actually thinking) – and they take ownership because the environment finally gives them the space to.

You’re no longer the constraint – you’re the multiplier.

And, guess what, you’re working less, not more. Because you’re not the twine holding trying to hold together a bursting package.

By phase 3, you understand how leadership coaching works – and you can apply the process yourself.

Fun right?

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How Leadership Coaching Works: What a Typical Session Looks Like

Before the session:

You prepare. Not with a formal agenda – with awareness. What patterns showed up this week? What situations frustrated you? What decisions are you facing?

During the session (60-90 minutes):

First 10 minutes: You download what’s happening while I’m listening for patterns.

Next 40-60 minutes: We dig into one or two situations. I ask questions that make you uncomfortable (fun for me!):

  • “What did you do right before that happened?”
  • “What would have happened if you’d said nothing?”
  • “What are you getting from being indispensable?”

We reconstruct the moment and try to spot the patterns. Then we connect those patterns to the environment it created.

Once we see the patterns, we can rearchitect the environment. Not with a standard framework but with specific behavioral changes.

Last 10-20 minutes: We talk about simple ways you can implement the changes immediately. You’ll be surprised how easy the changes are. In fact, you won’t even believe such small changes can make a difference. But that’s the magic of how leadership coaching works.

Between sessions:

You try out the new behavior and report back what happened. Then we refine, with miniscule changes, based on reality, not theory.

That’s the cycle: Spot pattern → Redesign environment → Test in reality → Refine → Repeat.

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Why This Works When Training Programs Don’t

Once you understand how leadership coaching works in practice, the difference from training becomes pretty obvious.

Training programs teach you tactics:

  • Better delegation frameworks
  • Improved communication techniques
  • Leadership processes

The problem: You’re applying new tactics inside the same environment with your same identity. You may make some changes with training programs, but after 30 days most of it will revert back to how you’ve always done things. The environment wins every time.

Leadership coaching is different – it redesigns the environment to allow for long-lasting change.

Once you see the environment you’ve built and how it supports the patterns you don’t like, tactics become unnecessary. You’re not trying to delegate better inside a system that revolves around you. You’re rearchitecting the system so delegation isn’t even needed – people just do the work on their own.

Here’s an example:

Training approach:

“This is a 5-step delegation framework. Use the RACI matrix. Schedule check-ins. Provide clear expectations.”

Coaching approach:

“You keep saying you want to delegate, but your calendar shows you’re involved in every major decision meeting. By always being there, your team will always default to your opinion. You’ve unconsciously designed a system where they NEED your input to proceed. Do you see that? Now let’s talk about how we can change that environment.”

See the difference?

One gives you tools to use inside the environment (it’ll never last). The other shows you the environment and helps you dismantle it.

(If you’re interested in learning more about this, check out Why Most Leadership Development Programs Fail)

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What Changes (And What Doesn’t)

What changes:

  • How you see problems
  • The environments you build
  • Your team’s capability
  • Your stress level
  • Your effectiveness

What doesn’t change:

  • Your core strengths (you’re still exceptional at what you do)
  • Your standards (you don’t lower the bar)
  • Your ambition (you scale it properly)
  • Who you are (you just lead from it differently)

This isn’t about becoming someone else. It’s about architecting environments where everyone can excel, not just you.

That’s why coaching is much more effective, and it’s how leadership coaching works for lasting transformation – it changes what you build, not who you are.

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The Questions Leadership Coaching Actually Answers

Not “How do I get my team to take more initiative?”
But: “What am I doing that prevents them from taking initiative?”

Not “Why can’t I find good people?”
But: “Why do I keep hiring people who need me to be involved, then get frustrated with their dependence?”

Not “How do I delegate better?”
But: “What am I getting from being indispensable that makes delegation feel threatening?”

Not “My team is underperforming, what are they doing wrong?”
But: “What environment have I built that keeps their talents dormant?”

The secret to how leadership coaching works is that the questions shift from “them” to “me.” Not because you’re the problem. Because you’re the architect.

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How Long Does It Take?

To spot the first major pattern: 1-3 sessions

To see real behavioral change: 3-6 sessions

To redesign the environment: 3-6 months months

To make it permanent: 6+ months

This isn’t a weekend workshop where you feel inspired then nothing changes. This is architectural work. Sure, it takes time. But it lasts.

Most executives who do this work stay with coaching for 9-18 months. Not because they’re dependent on it. Because once you start seeing patterns, you keep finding new ones to address. And as you find new ones to address, you’ll see your career flourish.

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What You Need to Bring

Honesty about what’s actually happening

Not the board-ready version. Not the version where you look good all the time. You need to talk about what’s actually happening, including your contribution to it.

If you can’t be honest about the pattern, I can’t help you see it.

Willingness to be uncomfortable

Good coaching feels uncomfortable. I’m going to point out patterns you don’t want to see. I’ll question narratives you’ve been telling yourself for years. You’ll start seeing behaviors that have worked for you in the past but no longer work now.

If you want validation, get a yes-man. If you want transformation, expect some discomfort.
That’s just how leadership coaching works.

Commitment to immediate application

Insights without action = expensive therapy.

The coaching cycle requires you to test new behaviors between sessions. Report what happened. Refine based on reality. Test again.

If you’re not willing to change anything, don’t hire a coach. But, the reality is that in choosing the right leadership coach, you should find a coach that understands how small behaviors lead to big changes.

In fact, you may want to check out a little bit about me to understand more.

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The Investment

Time: 2-4 hours per month (sessions + preparation)

Money: $3,000-10,000/month depending on the coach’s experience and the structure of the engagement.

Effort: Meaningful mental effort. Whether the work is hard or easy, depends on your openness to trying new behaviors. My goal is to make small behavioral changes that can transform an environment – little effort for huge gain.

ROI: One avoided bad hire ($500K-$2M), one pattern fixed before it scales ($5M-50M), one promotion that comes quicker than you thought it would (priceless).

In fact, if you want to understand the ROI for coaching, check out the complete leadership coaching ROI analysis.

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Ready to See the Pattern You Can’t See From Inside It?

Now you understand how leadership coaching works. The question is: are you ready to see what you’ve been building?

Option 1: Join The Free Leadership Diagnostic Workshop
Identify the unconscious patterns limiting your growth.
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Option 2: Take The Leadership Assessment
Identify which patterns are keeping your team dependent on you.

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Option 3: Start With My Newsletter
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Jeff Matlow spots patterns for a living. Specifically, the ones keeping your team dependent on you – and the siloed environment those patterns create. Then he shows you how to rearchitect the whole thing into a greenhouse environment where people can actually excel. 3x entrepreneur (all companies acquired). 25+ years working with leaders at L’Oreal, Disney, Nestlé, Porsche, Citi and hundreds of high-growth companies. Think Ted Lasso meets Brené Brown meets a Navy SEAL.