The Messy Middle isn’t About Change Execution, it’s About Culture Creation
Leading Change with Insight, not Fear
Most leaders underestimate the middle of a transformation. They plan for launch. They plan for go-live. But the middle - where employees are learning, struggling, experimenting, and adapting - is where a transformation either accelerates or collapses under its own weight.
This is the space where leaders face decision after decision.
· Big decisions.
· Daily decisions.
· Quiet decisions no one wants to make.
As we discussed in a recent newsletter, you can invest time and attention to assess readiness, align priorities, and address gaps before you launch the project - or push ahead to save time, get the project started…and pay later. Choose your hard.
You can choose your hard in the middle of the implementation too.
The Hard That Creates Adoption and Accelerates Benefits
or
The Hard That Creates Resistance and Threatens Success
One hard is intentional. The other hard is accidental.
One builds momentum. The other drains it.
One earns trust. The other breaks it.
And the difference is almost always the same:
Are you leading the change with people - or despite them?
The Two Middles Leaders can Create
Every transformation creates a lived experience for employees - one they will remember long after the project team has disbanded.
That experience will determine:
whether they adopt the change or quietly work around it
whether they feel valued or dismissed
whether they stay or leave
whether future changes become easier or exponentially harder
In the messy middle, leaders unintentionally choose between two very different paths.
Path 1: Leading With Fear (The “Just Do It” Method)
Fear-based leadership doesn’t always look like shouting orders. More often, it looks like speed-at-all-costs decisions made by leaders who believe they are helping the project by “removing friction.”
Fear-based execution sounds like:
“We don’t have time to involve them.”
“Just tell them what to do.”
“They’ll get on board once they see it in action.”
“Resistance is normal - ignore it and keep going.”
This path delivers short-term activity but long-term damage.
The Damage Leaders Don’t See Right Away
False compliance. People nod in meetings and stall in practice.
Workarounds. Employees do what’s easiest, not what’s intended.
Quiet resistance. The project moves forward…until it doesn’t.
Culture decay. Trust takes months to build and minutes to burn.
Knowledge drain. Your highest performers - the ones who care - leave first.
Change fatigue. Every future initiative becomes harder because employees now associate “change” with being ignored or dismissed.
Leaders think this path is faster. It absolutely isn’t. It’s simply feels easier and is therefore tempting. But it is undeniably the harder hard.
Path 2: Leading With Insight (The “With, Not At” Method)
When leaders choose engagement, questioning, co-creation, and experimentation, the middle looks very different and so do the long-term prospects for the company. This path requires courage. It requires patience. It requires curiosity. But it rewards you with something fear-based leadership can never deliver: Real, lasting adoption.
Leading with insight sounds like:
“What are we not seeing?”
“Who is closest to this problem?”
“What will make this change stick?”
“What assumptions might be getting in our way?”
“How can we test our ideas quickly and learn from them?”
This is change leadership that invites people, not directs them.
The Benefits Leaders Do See - And Often Faster Than Expected
Stronger solutions. The people doing the work help shape the work.
Higher adoption. People implement what they believe in.
Higher trust. Employees feel valued, not overridden.
Faster iteration. Early testing exposes issues when they’re easy to fix.
Momentum. The change doesn’t need to be pushed — it begins to pull.
A culture of possibility. The next change is easier because the last one was respectful, energizing, and meaningful.
This path may feel like the harder one to start. But it becomes the easier one to sustain and it is repeatable and scalable and rewarding and...
Why Questioning is the Lever that Changes Everything
If fear-based change is rooted in assumptions, then insight-based change is rooted in questions. Questioning is what opens possibilities, uncovers risks, reveals blind spots, and invites voices leaders rarely hear.
In the messy middle, your questions are cultural signals.
Fear-based questions sound like interrogation:
“Why isn’t this done yet?”
“Who is responsible for this gap?”
Insight-based questions sound like partnership:
“What are we learning?”
“What needs to be true for this to succeed?”
“What support do you need that you aren’t getting?”
“What is making this harder than it should be?”
Your questions either shrink the conversation or expand it; create fear or create clarity; silence insights or surface them. Leaders don’t create buy-in by making decisions. They create buy-in by creating meaning - and meaning comes from exploration, not enforcement.
The Experience you Create is your Legacy
Most leaders underestimate the emotional footprint they leave during transformation.
But employees never forget what the change felt like:
· They remember if leaders rushed them.
· They remember if leaders dismissed their concerns.
· They remember if their expertise was ignored.
· They remember if decisions were made behind closed doors.
And they also remember the opposite:
· They remember when they were invited in.
· They remember when their ideas shaped the outcome.
· They remember when they had a safe place to experiment.
· They remember when their leaders were learners, not enforcers.
Those experiences determine whether employees tell others, “This is a great place to work - you should come here,” or “It’s exhausting here - you should look elsewhere…and bring me with you.”
Your change experience becomes your talent strategy. Your talent strategy becomes your competitive advantage. The messy middle isn’t just about change execution. It’s about culture creation.
Choose Your Hard… Again
Leaders often think the hardest choice is at the beginning of change - do we take the time to assess readiness, align leadership, define the case for change or just get it underway?
You do choose your hard at the beginning. Now, in the middle of executing the change, you can choose your hard again.
· Choose the one that creates insight.
· Choose the one that builds trust.
· Choose the one that turns the messy middle into the most energizing part of the journey.
· Choose the hard that helps your people, and your organization, become better than they were before the change began.
When you look at it that way, the choice is easy.
