The Myth of Neat Progress
We celebrate neatness in business. The tidy board packs. The crisp KPIs. The slick strategy updates where every milestone is green.
But let’s be blunt.
“Real transformation never looks neat in the middle.”
Change is jagged. Growth is awkward. Progress is often dressed up in confusion, conflict, and second-guessing.
And yet… leaders are rewarded for polish. Investors want certainty. Executives strive to look in control.
That pressure keeps organisations stuck. Because when you sanitise the messy middle, you don’t eliminate risk — you eliminate possibility.
The Leadership Bias Against Messy
Why do leaders avoid messy?
Because messy looks dangerous. Messy means conflict, hesitation, or admitting “we don’t know yet.” That doesn’t play well in quarterly reviews.
Here’s the paradox: when everything looks smooth, you’re probably stuck on repeat. Safe. Familiar. Comfortable.
And comfort doesn’t get you to your next $5M, $10M, $20M+ in growth. Comfort doesn’t help you respond when AI rewrites your industry overnight. Comfort doesn’t inspire your talent to stay when the market offers them ten other choices.
Messy isn’t the risk. Avoiding messy is.
What Messy Really Signals
Messy is not chaos for chaos’ sake. Messy is the friction that signals growth is happening.
In just the last few weeks, I’ve seen messy show up as:
Strategic collisions – when priorities clash and the easy path is to smooth it over, instead of confronting what really matters.
Conflict surfacing – long-avoided tensions that finally come to the surface, creating discomfort but also the chance for resolution.
Confidence wobbles – a senior leader second-guessing themselves before presenting to their peers, only to step up with renewed clarity.
Radical candor – the uncomfortable honesty that temporarily destabilises trust but ultimately deepens it.
Unexpected decisions – external shocks that upend assumptions and force recalibration.
Every one of these moments felt disruptive. But handled well, each one created momentum:
Strategies became more cohesive.
Teams started collaborating across silos.
Individuals found the confidence to use their voice.
Decisions gained clarity and speed.
The messy middle is not a problem to solve. It’s a signal to leverage.
The Cost of Avoiding Messy
Too often, leaders confuse messy with risk. They rush to tidy things up. They shut down debate, postpone hard decisions, or bury discomfort under a pile of “action items.”
Here’s the danger:
Stagnation disguised as progress. Teams stay busy but stop moving forward.
Safe but irrelevant strategies. Leaders stick with what worked yesterday, even when tomorrow is screaming for something different.
Lost trust and innovation. When employees see leaders avoiding the real issues, they disengage.
We’ve all worked with, or for, organisations where avoiding messy turned them brittle:
They relied on certainty, refusing to act without perfect data.
They hesitated at the first sign of change, missing opportunities.
Or they chased reckless change, testing scenarios without insights, creating chaos instead of momentum.
In each case, the result was the same - wasted energy, missed opportunities, and leaders wondering why their teams felt stuck.
The adaptive business? It treats messy as insight. It listens to the discomfort. It reframes the friction. It uses messy as the energy to create new momentum.
A Story from the Room
A few weeks ago, I facilitated a leadership development day with a small group of executives. They knew each other well… and had drifted into silos. Growth had stalled. The market was shifting, yet they were clinging to old playbooks. Protecting their departments. Doubling down on what had worked before.
The symptoms were clear:
Cost-cutting positioned as “strategy.”
Passive-aggressive riddles in place of direct conversation.
Circular discussions where no one would commit.
Leaders quick to identify what others should change, yet blind to their own habits.
That’s the paradox of leadership silos: we see everyone else’s blind spots, yet not our own.
The energy in the room was heavy - think tense silence, sucked lips, suppressed frustration. Everyone felt it, no one named it. And their instinct, again, was to circle the hard conversation.
Circling carries a price: if they avoid the discomfort, the conflict, the discussion again, profit would nosedive, competitors would seize the upswing, and the business would be left stamping on old ground while the market moved on.
So instead, we went there. We actively invited conflict to the table.
What followed was messy, but transformational:
From tense silence through shaky voices and emotional uncertainty to courage in sharing opinions and perspectives.
From uncomfortable discussion of alternative perspectives (i.e. real conflict) to defining the actual challenge.
From circling blame to opening dialogue that clarified expectations and revealed the whole-of-business challenge, providing clarity to unlock solutions that can finally be actioned.
The room moved from avoidance, through candor, to alignment.
That day didn’t hand them an easy answer, there’s still work to do (there always is - that’s why it’s called growth…).
It did something more important.
It stripped away the noise and made the real challenge undeniable.
Messy didn’t derail that leadership team. Avoiding messy would have.
How to Lead Through the Messy Middle
So how do you stop messy becoming mayhem?
You strip it back to the real business challenge. Impartially. Unemotionally. Defenselessly.
When leaders stop making it about ego, turf, or blame, messy loses its sting. It stops being personal. It starts being progress.
One tool I use with leaders & their teams is the Good–Better–Best Framework:
Good – The first tangible step forward, however small. Move something this week.
Better – Compound the wins that build confidence and trust.
Best – Keep the long-term milestone in sight, without crushing the team with perfection right now.
It’s simple, but it works. Because it reframes messy from “we’re failing” into “we’re building.”
Use it like this…
Three Questions for Your Leadership Team This Week
Where are we mistaking discomfort for danger?
What’s the real business challenge under our current “messy”?
What’s our next Good step — and how do we build from there to Better?
If you’re not hitting messy, you’re not stretching. You’re looping safely in the familiar.
Messy is the dip before the lift. The recalibration before the acceleration. The uncomfortable signal that you’re on the edge of extraordinary.
So here’s my challenge to you…
Stop chasing neat. Start leveraging messy.
And if you want to explore how messy is showing up in your leadership team, and how to turn it into momentum, let’s have that conversation.
Because in the end, neat is a story you tell shareholders. Messy is where transformation is born.
👉 Download a copy of the Good, Better, Best framework - your 10 min guide to momentum - using this link.
To your extraordinary.
Sandy