The Messy Middle of Transformation: Hard Lessons That Make The Work Actually Work
Hard lessons from the part no one puts in the plan
Image: David Villasana
There’s a point in every transformation where the language changes.
The early phase is all ambition.
Vision. Energy. Big words. Big promises.
Then you move into delivery and the tone shifts.
Suddenly it’s about timelines, resources, dependencies, approvals.
About who owns what.
About what can and can’t be done.
About what was assumed… and what turns out not to be true.
That’s the messy middle.
And it’s where most of the real learning happens.
When the plan meets the organisation
I once walked into a role that had been sold as a greenfield transformation opportunity.
New direction. Senior sponsorship. Space to build. All the right language.
Within the first few weeks, it was clear the reality was very different.
Budgets were still being negotiated.
Decision-making authority was split across multiple leaders.
Key stakeholders were aligned in public and divided in private.
And a multi-quarter programme had quietly been condensed into a matter of weeks.
On paper, the role existed. In practice, it didn’t.
What existed instead was urgency without infrastructure.
Expectation without alignment.
And a team that was already stretched before the work even began.
We delivered. Of course we did.
But the way it happened, the constant recalibration, the political navigation, the trade-offs no one wanted to acknowledge, taught me more about transformation than any framework ever could.
Because that’s the reality most plans never reflect.
The things you only see once you’re inside
From the outside, transformation looks linear.
Inside, it’s anything but.
You start to notice:
how long decisions actually take
how often “alignment” is assumed rather than tested
how many people have veto power without being obvious about it
how frequently priorities change without being formally reset
You see how work gets stuck between functions.
How initiatives lose momentum because no one quite owns them.
How politics creeps in when pressure rises.
How people protect their territory when they feel exposed.
I’ve worked in environments where three leaders thought they owned the same decision.
Where “agreed” meant “agreed for now”.
Where speed was demanded but process was missing.
Where delivery teams were blamed for delays caused by governance.
None of that shows up in the deck.
All of it shapes the outcome.
When pace becomes the problem
One of the most consistent patterns I’ve seen is compression.
Timelines that shrink because someone wants momentum.
Scopes that expand because ambition isn’t matched by restraint.
Teams that are expected to absorb more because “this is important”.
It always starts with good intent.
But when pace outstrips structure, things begin to wobble.
People cut corners. Trust erodes. Quality drops. And relationships start to fray.
You might still launch something. But you pay for it elsewhere.
In energy. In goodwill. In credibility.
The cost just shows up later.
The politics no one names
Another thing you learn quickly: transformation redistributes power.
New roles appear. Old ones fade. Influence shifts. Visibility changes.
And people notice.
I’ve seen leaders who were supportive on Monday become obstructive by Friday because something moved underneath them.
I’ve seen collaboration dry up because someone felt sidelined.
I’ve seen decision-making slow to a crawl because no one wanted to be seen to lose.
Not because people are malicious.
Because they’re human.
And when change threatens identity or status, behaviour follows.
If you don’t design for that, it designs itself. Usually badly.
The lesson that sticks
The biggest lesson I’ve learned from the messy middle is this:
Transformation is rarely a capability problem.
It’s usually an alignment problem.
Between strategy and structure.
Between ambition and resource.
Between leadership and reality.
When those things drift, no amount of enthusiasm will save the work.
And the only way to see that drift is to be close enough to the detail.
Close enough to the conversations.
Close enough to the friction.
Not managing from a distance.
Not directing from above.
Being in it.
Why this matters
Because most organisations don’t struggle with ideas.
They struggle with execution.
Not because people aren’t capable.
But because the system around them isn’t ready.
Because decisions are unclear.
Because ownership is fuzzy.
Because the pace is unrealistic.
Because politics are unacknowledged.
The messy middle is where all of that surfaces.
And if you’re not prepared for it, it quietly undoes the work.
The truth about the middle
It’s not glamorous.
It’s not neat.
And it’s rarely where credit is given.
But it’s where transformation is either built properly… or compromised.
The leaders and teams who navigate it well aren’t the ones with the best slides.
They’re the ones who:
notice where things are getting stuck
name misalignment early
slow down when the system needs it
and aren’t afraid to deal with what’s actually happening, not just what was planned
That’s the work.
Not the announcement.
Not the launch.
The middle.