Why Mid-Level Leaders Struggle (and What Actually Helps)

There’s a level in organizations that carries a huge amount of responsibility for results…and gets almost no support.

Mid-level leaders.

They’re expected to:

• drive results

• lead teams

• navigate complexity

• translate strategy into action

And most of the time, they’re left to figure it out.

No coach

No real-time support.

Maybe a workshop… months ago.

The Gap Isn’t Insight—It’s Application

Most mid-level leaders aren’t lacking in awareness.

They’ve been exposed to frameworks and taken assessments.

They understand concepts like communication styles and team dynamics.

But what I hear from their leaders is consistent:

“We’ve given them the tools for self-awareness—but they can’t catch themselves in the moment when it matters.”

That’s the gap.

Not insight.

Application.

Where This Shows Up Every Day

This gap doesn’t show up as a lack of effort, but instead in moments like:

• The moment before a tough conversation and subsequently avoiding it

• Right after a meeting that didn’t go well, moving on without reflection

• In the middle of a decision under pressure and defaulting to old patterns

• Over-functioning instead of delegating

• Struggling to align across functions

These are the moments that actually define leadership.

And they’re exactly where most development disappears.

Why Traditional Development Falls Short

Most leadership development is episodic:

• A workshop

•  A training session

• A one-time assessment

These can create valuable insight.

But without reinforcement, that insight fades—especially in fast-moving environments.

Mid-level leaders don’t need more information.

They need a way to use what they already know, in real time.

From Insight to Behavior: What Shifts

A leader I worked with described a common frustration:

“I know my patterns—I just can’t catch them in the moment.”

Like many leaders, they had done the workshops and understood their Enneagram type. But under pressure, they defaulted back to old habits.

What changed wasn’t more insight, but rather having a way to engage with it consistently and in the flow of their work.

Such as:

• Talking through situations before responding

• Reflecting after key moments

• Recognizing patterns as they were happening

Over time, something shifted.

Not just awareness but their behavior.

Their team experienced them as more present, more thoughtful in decision-making, and less reactive in challenging moments.

A More Practical Approach

This is the shift we’re making with EnneaEDGE.

Not more content. Not another standalone program.

Instead, we've created a way for leaders to engage with insight:

• before a conversation

• after a meeting

• during a decision

In the moments that actually define their leadership.

It supports different ways of learning:

• Seeing patterns

• Talking things through

• Reflecting over time

But more importantly, it helps leaders apply insight when it matters.

Why This Matters

Mid-level leaders are the ones who:

• shape the day-to-day experience of teams

• drive execution

• carry culture forward (or not)

When they’re supported, performance improves.

When they’re not, even strong strategies struggle to take hold.

If you’re a mid-level leader trying to lead well in a complex environment—without a lot of support—you’re not alone.

And you don’t need more theory.

You need a way to catch yourself in the moment—and choose how to respond.

That’s where leadership shifts.

And that’s exactly the problem I’m focused on solving with EnneaEDGE. Learn more about my Growth-to-Action program working with EnneaEDGE here and begin catching yourself in the moments that matter. 

I also wrote more about this here and here!