Why Most Training and New Initiatives Fail (and How to Roll Them Out the Right Way)

Early in my career, I trained hundreds of leaders and sales professionals across telecom and corporate retail environments.

High volume.
High pressure.
Aggressive targets.
Constant change.

The mandate was simple: train fast, deploy quickly, drive results.

And on the surface, it worked.

Sales went up.
Energy was high.
People left sessions motivated.

But something never sat right with me.

A few weeks later, performance drifted.
New behaviors faded.
Old habits quietly returned.

At the time, I assumed the issue was execution or accountability.

It wasn’t until years later after becoming an executive coach and corporate facilitator with Maxwell Leadership, and leading workshops and learning labs with Fortune 500 companies, that the real pattern became impossible to ignore.

That realization was a huge eye-opener.

Most training programs don’t fail because the content is bad.
They fail because they are rolled out incorrectly.

They ignore how adults actually learn.

The Pattern I Saw Everywhere

Across industries and organizations, the same pattern repeated itself:

• A new initiative is announced

• Training is delivered in a compressed format

• Leaders are told, “Now go execute”

• Follow-up is minimal or nonexistent

• Coaching is optional. If it exists at all

Then leadership wonders why:

• Behavior doesn’t change

• Teams resist

• Momentum stalls

• ROI disappears

The problem wasn’t motivation.
It wasn’t intelligence.
It wasn’t buy-in.

It was design.

The Model That Changed Everything

As my work shifted deeper into executive coaching and leadership development, three principles kept showing up, consistently and predictably.

When learning stuck, these were present.

When it didn’t, they weren’t.

Space.
Time.
Repetition.

And eventually, the most important realization of all:

Without coaching, none of the three are fully activated.

1. Space: We Need Room to Think Before We Can Change

In high-performance environments, leaders are rarely given space.

They’re rewarded for speed, decisiveness, and output not reflection.

But adult learning requires psychological and cognitive room.

Early in my career, we packed sessions tight:

• More slides

• More scripts

• More tactics

What I didn’t yet understand is that adults don’t learn by accumulation.
They learn by integration.

Space allows leaders to:

• Step out of reaction mode

• Reflect on their patterns

• See themselves in the material

• Connect learning to real-world decisions

Without space, training becomes noise.

2. Time: Change Needs an Incubation Period

Adults don’t change on command.

Insight follows a predictable arc:

Insight → Resistance → Application → Reflection → Integration

That arc requires time.

When training is rushed or treated as a one-time event:

• Insight stays intellectual

• Behavior remains unchanged

• Old habits resurface under pressure

When learning is spaced over time with room to test, fail, adjust, and reflect...real change begins to take hold.

This is why:

• Ongoing leadership programs outperform intensives

• Quarterly strategy sessions beat annual offsites

• Coaching engagements outperform workshops alone

Time doesn’t slow growth.
It enables it.

3. Repetition: Familiarity Builds Ownership

One of the most common things leaders say is:

“I already know this.”

What they usually mean is:

“I haven’t been held accountable to apply this.”

Repetition isn’t redundancy.
It’s reinforcement.

Under stress, people don’t rise to new ideas.
They default to familiar patterns.

Effective repetition looks like:

• Revisiting the same principle in new contexts

• Applying frameworks to real decisions

• Increasing expectations for ownership over time

Repetition ensures the right behaviors become automatic.

The Missing Link: Coaching

Here’s the biggest realization and the one most organizations miss.

Even space, time, and repetition aren’t enough without coaching.

Training explains the what.
Coaching addresses the why and the how.

Coaching:

• Translates insight into behavior

• Surfaces resistance safely

• Creates accountability

• Sustains momentum

Without follow-up coaching:

• Learning decays

• Initiatives stall

• Leaders feel unsupported

• Culture absorbs the change instead of being changed by it

Training introduces change.
Coaching makes it stick.

 

Why Communication Breaks Rollouts 

Another realization emerged over time:

Most initiatives don’t fail at the strategy level.
They fail at the communication level.

Leaders assume:

“We communicated this clearly.”

What they really did was communicate it once, in one style, through one lens.

DISC helped make this visible.

People don’t resist change; they resist how change is communicated.

Results-oriented leaders need clarity and outcomes.
People-oriented leaders need vision and connection.
Stability-oriented leaders need reassurance and time.
Process-oriented leaders need logic and structure.

Same initiative.
Different message delivery.

When leaders communicate with behavioral styles in mind, adoption accelerates, and resistance drops.

The Flywheel That Actually Works

When development is designed correctly, a flywheel forms:

• Space creates awareness

• Time allows integration

• Repetition builds confidence

• Coaching drives ownership

This is the difference between:

• Training and transformation

• Compliance and commitment

• Knowing and doing

A Question for Growth-Minded Leaders

Where in your organization or your own leadership...are you:

• Launching initiatives without follow-up?

• Expecting behavior change without coaching?

• Communicating once and assuming it landed?

Your answers may reveal why progress feels harder than it should.

Once you see this, you can’t unsee it.

If you’re a growth-minded leader preparing to launch a new strategy, system, or organizational change or trying to rescue one that’s stalled...I created a practical guide will help you:

✔ Avoid common rollout mistakes
✔ Increase adoption and buy-in
✔ Design initiatives that actually stick
✔ Lead change with clarity, intention, and follow-through

Comment "Rollout Guide" and I'll send it to you.