The Pattern Spotter: Why Leaders Repeat the Same Mistakes

Reading time: 5 minutes

You’ve changed companies three times.

Different industries. Different teams. Different challenges.

But somehow, you’re dealing with the same problem.

Your boss micromanages you (again). Your team doesn’t take initiative (again). You’re working 65-hour weeks to compensate (again). The promotion that was “definitely happening” didn’t (again).

Different people. Same pattern.

Understanding why leaders repeat the same mistakes is the first step to breaking free from them.

Here’s why – and what to do about it.

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You’re Not Unlucky. You’re Pattern-Blind.

Most leaders think they have a string of bad luck:

Bad boss
Weak team
Political environment
Unclear expectations
Wrong company culture

But when the same problem follows you across multiple situations, you’re not looking at bad luck. You’re looking at a pattern.

The uncomfortable truth:
You’re creating the problem. Not consciously. Not intentionally. But you’re the common denominator.

And you can’t see it. Because patterns operate on autopilot.

This is why leaders repeat the same mistakes across different companies, teams, and situations – the pattern is invisible to the person running it.

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Why Leaders Repeat the Same Mistakes: How Patterns Actually Work

You Learned Them 10-20 Years Ago

Example:

When you were 25, you had a boss who loved detail. The more thoroughly you prepared, the more he trusted you. So you learned: thoroughness = value.

Twenty years later, you’re still preparing for every meeting like you’re defending a dissertation. Your team is frustrated. Your peers think you’re slow. Your boss wants faster decisions.

But you can’t stop. Because the pattern runs automatically.

The pattern: Thoroughness = value
The behavior: Over-preparation, slow decision-making, analysis paralysis
The cost: Speed, agility, team frustration

They Worked Then. They Don’t Work Now.

That thoroughness pattern worked when you were an individual contributor. It helped you build credibility. It got you promoted.

But at senior levels? It’s killing you.

The problem with patterns:

They’re unconscious (you don’t know you’re doing it)
They’re automatic (they run without your input)
They worked in the past (so your brain thinks they should work now)
They’re invisible to you (you can’t see your own blind spots)

They Show Up in Every Situation

Here’s how you know it’s a pattern and not just a circumstance:

Circumstance: “My current boss micromanages me.”
Pattern: “Every boss I’ve had eventually starts micromanaging me.”

Circumstance: “This team doesn’t take initiative.”
Pattern: “None of my teams have taken initiative without prompting.”

Circumstance: “This company has unclear expectations.”
Pattern: “I’ve never felt like expectations were clear enough.”

When it happens once, it’s a circumstance.
When it happens every time, it’s a pattern.

This is the key to understanding why leaders repeat the same mistakes – they’re responding to an internal pattern, not external circumstances.

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The Five Most Common Leadership Patterns (And How They Show Up)

Pattern 1: “I Need to Be Needed”

The origin:
You got early reinforcement for being helpful. Being needed felt good. So you learned: value = being indispensable.

How it shows up:

You jump in to solve problems before anyone asks
You answer questions instead of making people think
You work late to pick up slack
Your team is dependent on you
You feel anxious when things run without you

The cost:

Your team doesn’t develop capability
You’re constantly overwhelmed
You can’t delegate effectively
People stop trying to solve things themselves
You’re the bottleneck

The hard truth:
You’re creating the dependency you resent. This is one of the most common reasons why leaders repeat the same mistakes – they unconsciously create the very problem they’re trying to solve.

Pattern 2: “I Need to Be Right”

The origin:
You were rewarded for being smart. Being right felt like being valuable. So you learned: credibility = being correct.

How it shows up:

You debate every point
You can’t let incorrect statements pass
You need the last word
You struggle to delegate decisions
You reopen discussions after they’re settled

The cost:

Your team stops sharing ideas
Innovation dies
People wait for you to decide everything
Good people leave
You’re exhausted

The hard truth:
Being right all the time makes you wrong about what matters.

Understanding why leaders repeat the same mistakes like this requires seeing how being right became more important than being effective.

Pattern 3: “I Need to Please Everyone”

The origin:
You learned early that conflict was dangerous. Being liked felt safe. So you learned: safety = approval.

How it shows up:

You avoid hard conversations
You say yes when you should say no
You soften feedback until it’s useless
You don’t hold people accountable
You downplay problems to keep people comfortable

The cost:

Underperformers stay
Top performers leave
Standards drop
Problems fester
You lose respect

The hard truth:
Trying to please everyone guarantees pleasing no one (including yourself).

This explains why leaders repeat the same mistakes with underperformance – avoiding accountability feels safer than having hard conversations.

Pattern 4: “I Need to Control Everything”

The origin:
You got burned by trusting someone. Control felt safe. So you learned: safety = oversight.

How it shows up:

You review everything before it ships
You’re in every meeting
You second-guess decisions
You redo work that’s “not quite right”
You feel anxious when you’re not involved

The cost:

Bottlenecks everywhere
Team resentment grows
Innovation stops
Good people leave for autonomy
You’re exhausted

The hard truth:
Control is an illusion that costs you everything you’re trying to protect.

Pattern 5: “I Can Power Through This”

The origin:
You succeeded through sheer effort and determination. Hard work solved everything. So you learned: effort = success.

How it shows up:

You work longer hours instead of changing approach
You add more meetings instead of fixing the system
You do more instead of doing different
You’re exhausted but can’t stop
You resent people who set boundaries

The cost:

Burnout
Health problems
Relationships suffer
Diminishing returns on effort
Still not solving the actual problem

The hard truth:
Working harder on the wrong approach just gets you the wrong result faster.

This pattern shows why leaders repeat the same mistakes even when they’re working incredibly hard – effort without awareness just reinforces the pattern.

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Why You Can’t Spot Your Own Patterns

There are five reasons leaders repeat the same mistakes even when they’re smart, capable, and self-aware.

Reason 1: They’re in your blind spot
You can’t see your own face without a mirror. You can’t see your own patterns without external perspective.

Reason 2: They feel like truth, not pattern
From inside the pattern, it feels like you’re responding to reality. “My team DOESN’T take initiative.” You don’t see that you’ve trained them not to.

Reason 3: They’re validated by results (sometimes)
Patterns worked in the past. Your brain has evidence they’re correct. So it keeps running them even when circumstances change.

Reason 4: Your ego protects them
Seeing your patterns means admitting you’re contributing to your problems. Your ego would rather blame circumstances.

Reason 5: Everyone around you plays along
Your team adapts to your patterns. Your boss works around them. The system accommodates them. So you never get clear feedback that something’s wrong.

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How to Actually Change Patterns

Step 1: Get Someone Who Can See What You Can’t

The biggest reason why leaders repeat the same mistakes is lack of external perspective. You need someone who can see what you can’t.

You need external perspective.
A coach.
A mentor.
Someone who can spot patterns across situations.

Not a friend (too nice).
Not a peer (same blind spots).
Someone who’s trained to see patterns and has no stake in keeping you comfortable.

Step 2: Get Honest About What’s Actually Happening

Stop blaming:

Your boss
Your team
Your company
Your circumstances
Your bad luck

Start asking:

“What’s my contribution to this problem?”
“Where have I seen this before?”
“What am I getting out of maintaining this pattern?”
“What am I avoiding by keeping this pattern?”

Step 3: Name the Pattern Specifically

Vague awareness doesn’t change anything.

Bad: “I guess I’m a perfectionist”
Good: “I need to be right, so I argue every point, which makes my team stop sharing ideas”

Bad: “I might be a people pleaser”
Good: “I avoid accountability conversations because I need approval, which is why underperformers stay on my team”

Specificity creates leverage.

Step 4: Test New Behaviors (Even When They Feel Wrong)

New behaviors always feel awkward. That’s how you know they’re new.

Example pattern: “I need to be needed”

Old behavior: Answer every question immediately
New behavior: “What do you think?” before solving it

It will feel:

Uncomfortable (what if they think I don’t know?)
Scary (what if they make the wrong choice?)
Wrong (I COULD solve this faster)

Do it anyway. The discomfort is temporary. The pattern is permanent (until you change it).

Step 5: Notice What Changes (And What Doesn’t)

If the new behavior works:

People start solving things themselves
You have more time for strategic work
Team capability increases
You feel less overwhelmed

If it doesn’t work:

You might be doing it wrong
You might need a different approach
You might need more time
You might be working on the wrong pattern

Either way, you’re learning. Which is more than you were doing when the pattern was running on autopilot.

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The “Oh Shit, That’s Me” Moment

Real pattern recognition feels like this:

“Oh shit. I do that. I do that in EVERY situation. That’s why this keeps happening. Holy fuck, it’s not them – it’s me. I’ve been doing this for years. No one ever told me. Or they tried and I didn’t hear it.

This is the moment you finally understand why leaders repeat the same mistakes – it’s not bad luck or circumstances, it’s patterns running on autopilot.

This is uncomfortable. But also… weirdly exciting? Because if it’s me, then I can actually change it. I’m not stuck. I just couldn’t see it before.”

That moment – when you truly SEE your pattern for the first time – changes everything.

Not because the pattern disappears (it doesn’t).
Not because the work is done (it isn’t).
But because now you can see it. Which means you can change it.

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Ready to Spot Your Patterns?

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The patterns that got you here won’t get you there. But you can’t change what you can’t see.

And now you know why leaders repeat the same mistakes – and more importantly, how to stop.
You’re welcome.

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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.