Leading Through the Mess: Fixing Dysfunctional Teams and Organizations

Because sometimes the real problem isn't the people. It's the system they're stuck in. (The Art of the Fix Series)

Dysfunction Isn’t a Flaw. It’s a Signal.

Let’s say the quiet part out loud: Most teams don’t fail because they’re lazy or incompetent.
They fail because no one ever built them to function under pressure in the first place.

The truth is, dysfunction is rarely about “difficult people.”
It’s about dissonant systems, misaligned goals, unspoken rules, tangled incentives, that slowly squeeze the energy out of good people until all that’s left is politics, confusion, or quiet disengagement.

And by the time the damage becomes visible?
It’s already systemic.

Here’s what I’ve learned walking into these situations over and over again:

Dysfunction doesn’t show up as fire. It shows up as fog.
– You can’t trace a decision back to who made it.
– Meetings happen, but outcomes vanish.
– The person with the most context isn’t in the room or stopped talking months ago.

At first glance, nothing’s technically broken. Which makes the slowdown that much harder to diagnose. This is where most leaders double down on urgency.
They push harder, add trackers, assign more check-ins, thinking the problem is effort.

But dysfunction isn’t a workload problem. It’s a trust + clarity problem in disguise.

So what do I do when I sense dysfunction in the air?

I don’t treat it as failure. I treat it as signal intelligence. Because when a team stops flowing, something upstream is blocking the current:
– Misaligned KPIs across departments
– Leadership sending contradictory signals
– Psychological safety eroded by a culture of “pleasant silence”
– Or just an outdated structure that no longer fits the complexity of the work

None of these things fix themselves. They calcify. And if no one names it, dysfunction becomes the new normal. The team adapts, not to high performance, but to navigating the mess silently.

The Leader’s Job Is Not to Keep the Illusion Alive

The job is to name what’s real, without creating shame. To shift from “Why aren’t people executing?” to “What assumptions, incentives, or structures are making execution inconsistent, political, or exhausting?” This is why I say: Dysfunction isn’t a flaw in your people. It’s a message from your system. And if you learn to listen to it, not fight it, you can rebuild the environment so that people want to show up again.

Diagnosing Organizational Gridlock (Without Burning Political Capital)

Let’s get something straight: dysfunction rarely begins with dysfunction.
It begins with good intentions, wrapped in miscommunication, sealed by avoidance.
No one sets out to build a stuck organization. But layer by layer, we tolerate just enough misalignment to quietly kill momentum.

And here's the dangerous part: The longer it festers, the more it looks like normal.

Gridlock isn’t chaos. It’s coordination theatre.

Everyone’s busy. Deadlines are slipping. Meetings are happening. Budgets are being updated.

But decisions? Blocked.

Initiatives? Stalled.

Morale? Sinking, but no one’s saying it out loud, because the vibe is still “professional.”

This is what I call Operational Gaslighting, a state where the system is clearly stuck, but the signals are being minimized or reframed to preserve optics.

What’s actually happening underneath?

Let’s break it down. When I step into an organization that feels stuck, I’m scanning for four things, not in the org chart, but in the behavior patterns:

1. Decision Paralysis Hidden as “Collaboration”

When decisions ricochet between teams like a game of political dodgeball, it usually means one of two things:
– No one feels authorized to make the call
– Or they are authorized, but fear the fallout

The result? Meetings instead of movement. Slack threads that spin into infinity. And “alignment sessions” that align no one.

Real collaboration requires clarity of ownership. Without it, you’re just politely delaying progress.

2. Meetings That Sound Smart but Do Nothing

Look for the symptoms:
– Sharp language. Clear agendas. But no decisions.
– The same topic resurfaces every week with slightly new vocabulary.
– People leave unclear on next steps, but too professional to say so.

This is performative alignment. Everyone’s showing up. No one’s driving.

If every meeting ends with “let’s keep exploring,” your real problem isn’t complexity. It’s avoidance dressed in intelligence.

3. The Ownership Mirage

Here’s a phrase that should immediately raise alarms:

“Oh, we all kind of own that.” Translation? No one does.

Shared ownership sounds democratic. But in reality, it’s a way to spread blame so thin that no one feels it, and therefore, no one acts.

I’m always asking:
– If this fails, who loses sleep?
– Who owns the last ‘yes’ or ‘no’?
– And do they know that?

If there’s no clear answer in under 30 seconds, we’ve got fog.

4. Silent Disengagement

This one’s subtle. You won’t see tantrums or walkouts. You’ll see:
– Fewer proactive ideas
– More “Let me check on that” loops that go nowhere
– A tone of politeness that masks detachment

This is the organizational equivalent of emotional burnout.
People haven’t quit. But they’ve stopped investing.

Dysfunction has moved from the system into the culture, and the culture has adapted to survive instead of thrive.

My Go-To Tool: The Organizational MRI

When I sense gridlock, I don’t start with diagnostics tools or employee surveys.
I start by watching how decisions actually happen (or don’t).

My Organisation MRI questions:
– Where does energy drain most consistently?
– Which people hold invisible power but no formal authority?
– What’s being avoided that everyone feels but no one will name?

The point isn’t to call people out.
It’s to map where power, fear, and silence are shaping the work, more than the strategy is.

Strategic Insight: Most dysfunction lives between roles, not within them.

It’s the misaligned handoffs.
The undefined escalation paths.
The cultural scripts that reward being agreeable more than being clear.

And the best leaders? They don’t just fix the visible mess.
They decode the invisible forces holding it in place.

Implementing Cultural Shifts That Stick

Let’s make one thing very clear: You cannot “motivate” your way out of dysfunction.
You can’t rebrand it with a shiny values slide or fix it by sending everyone to a two-day leadership retreat with nice catering and zero follow-up.

Culture isn’t a keynote. Culture is what people normalize under pressure.

It’s not what you say on the all-hands call.
It’s what people believe they’re allowed to do when things get messy.

And most of the time? They’re looking for permission to stop pretending and start solving.

Here are the three cultural pivots I make inside dysfunctional teams, not with theory, but with actual behavioural shifts:

1. Make Directness Normal, Without Making It Brutal

Most teams think they have a communication issue.
What they really have is a conflict-avoidance culture in a productivity costume.

Everyone’s being “nice.” Which means no one’s being clear.

So I build space for constructive tension, places where it’s safe to say:

“We’re not aligned. Let’s reset before we waste three more weeks.”

How?

– I reward the first person who names misalignment without flinching
– I model non-defensive listening when someone pushes back
– I make “disagree and commit” a shared muscle, not a taboo

Clarity is kindness. But you have to make it emotionally safe before it becomes operationally useful.

2. Kill the Hero Culture (Before It Kills Your System)

If your highest performers are burning out while silently covering everyone else’s gaps, your system is broken, and your culture is complicit.

Heroism feels noble. Until it becomes structural dysfunction with a halo.

If the same three people keep saving the day, the team isn’t growing. It’s coping.

So I make two moves:
– I stop rewarding last-minute salvages that were preventable
– I shine a light on process redesigns and collaboration that prevent crises entirely

The heroes don’t need to be punished.
They need to be unburdened, so the team can grow past them.

3. Turn Clarity Into Ritual (Not a Project)

Everyone says they want clarity. But clarity isn’t a one-time statement, it’s a rhythm.

A cultural pulse that keeps everyone synced.

So I install small, durable rituals that reinforce alignment:
– Weekly 15-minute “What matters now?” meetings
– One-page project briefs written in plain language
– Shared visibility on blockers, not to assign blame, but to activate support

The magic isn’t in the format. It’s in the consistency.

Culture is what people repeat under pressure. Rituals make that repetition effortless.

Case-in-Point: The "We’re All Accountable" Trap

At a scale-up I worked with, every team was proud of being flat and “non-hierarchical.”
It sounded cool, until the product launch derailed.

Why? No one was actually owning anything.
Everyone was weighing in, no one was leading.

We didn’t change the organisation chart. We changed the behavior:
– Named final decision-makers for every stream
– Added a simple rule: If no one owns it, it doesn’t move
– Built “disagree and commit” into weekly ops cadence

In two weeks, you could feel the cultural temperature shift, from nice and unclear, to honest and aligned.

Cultural Shift Rule of Thumb: If it doesn’t show up in meetings, decisions, or how people handle tension, it’s not culture. It’s branding.

Restructuring for Flow (Not Just Control)

Let’s be honest: Most organisation structures weren’t designed for flow.
They were designed for reporting lines, permission hierarchies, and the illusion of order.

The result?

– Endless approval loops
– Ownership confusion disguised as “collaboration”
– Bottlenecks that wear suits and sit in corner offices

When things get dysfunctional, the reflex is usually to add more structure.
New RACI charts. More layers. Reorgs that shuffle chairs without changing dynamics.

But here’s the problem: You can’t spreadsheet your way out of stuckness.
Structure only helps when it aligns with how work actually flows.

So instead of starting with boxes and lines, I start with these three redesign principles:

1. Fix Misaligned Incentives Before You Touch the Organisation Chart

I’ve seen entire departments go to war not because they disliked each other, but because their KPIs were quietly at odds.

Example:
– Sales is rewarded for speed
– Ops is penalized for risk
– Finance is obsessed with cost control
– Product is stuck in the middle, begging for sanity

This isn’t dysfunction. It’s design failure.

Fix: Align incentives so that cross-functional success is the default path to individual success.

If you want flow, you have to make collaboration profitable, not exhausting.

2. Remove “Ghost Ownership”

Nothing kills velocity faster than unclear ownership.
I call it ghost ownership, everyone’s involved, but no one is responsible.

The fix is simple, brutal, and necessary: “If this fails, whose reputation is on the line?”
If the room goes quiet, the system’s broken. I implement this rule:
Every deliverable has one single accountable owner.
Others may consult, contribute, review, but someone owns the outcome.

And they have the authority, and protection, to act like it.

3. Redesign for Movement, Not Control

Most organisations are optimized for approvals.
That’s how you end up with twelve-person committees to launch a landing page.

I help teams shift from control-based structures to flow-based operating models:
– Cut handoffs in half
– Remove approval steps that serve no risk mitigation purpose
– Design cross-functional squads that solve end-to-end, not just pass the baton

Quick test: If it takes longer to get sign-off than to do the actual work, you’ve built a shrine to inertia.

Clarity enables speed. Control chokes it.

Case-in-Point: Velocity by Design: One company I worked with had a brilliant team buried under red tape.
A single product decision required five approvals across three continents.

Why? Legacy fear.

We ran a surgical restructure:
– Delegated budget control to the team level (within guardrails)
– Rewrote the approval policy: "If the cost is < X and risk is low, ship it."
– Created a post-mortem culture that celebrated fast learnings, not perfect bets

Within six weeks, delivery time dropped by 35%.
Team engagement went up.
Leadership anxiety went down, because clarity replaced micromanagement.

Control feels safe. But control is a substitute for trust.

You can’t empower people to move and demand they seek permission at every step.

Restructuring Rule of Thumb: If your structure needs a 12-page guide to explain who does what, it’s too complex to survive real pressure.

Simplify until movement is obvious.

V. From Dysfunction to Flow

Let me tell you about a team that looked great on paper, until you actually worked with them.

The setup: Mid-sized SaaS company, Series C stage.
Cross-functional product team managing one of the most public-facing initiatives they had.
On the organisation chart, everything was “collaborative.”
In reality? No one was speaking the same language.

– Product had no authority to push back on timeline changes
– Marketing kept shipping messages that didn’t match the feature set
– Engineering silently rewrote half the requirements just to make deadlines work
– Leadership kept asking, “Why are we behind?” with PowerPoint-fuelled optimism

Sound familiar?

Diagnosis: Dysfunction in Four Layers

Instead of jumping into process design or setting new goals, I spent the first week just watching.

Here’s what I uncovered:

1. No shared definition of success
   Each team had a different target. Marketing was aiming for launch metrics. Product was tracking feature velocity. Leadership wanted “strategic momentum” (whatever that means). Everyone was running… in different directions.

2. Conflicting directives from leadership
   Depending on which VP you talked to, the team had either “full ownership” or “strict oversight.” Which led to… fear-based decision-making.

3. Zero feedback culture
   Junior team members knew the misalignment was bad, but no one felt safe speaking up. Everyone was waiting for someone else to name it.

4. Workflow by avoidance
   Most critical issues weren’t blocked, they were quietly dropped, delayed, or shipped half-baked to “keep moving.”

This wasn’t a performance issue.
This was a clarity collapse wrapped in cultural politeness.

The Intervention: Small Levers, Big Shifts

Here’s how we flipped the script, without burning the house down:

Step 1: Created a Single Success Metric

We held one cross-team session where everyone, Product, Marketing, Engineering, Exec sponsors, defined a single outcome for the quarter.

We didn't wordsmith. We simplified:

“This quarter’s win: Increase activation rate by 20% post-signup.”

Suddenly, decisions started aligning.

Step 2: Rewrote the Rules of Ownership

We implemented a “Final Say Matrix.” For each key domain:
– One person had the final decision
– Others could advise or execute, but not override
– Disagreements were surfaced early, not late

No more Slack wars. No more circular “feedback” loops.
Just clean responsibility lanes, publicly agreed.

Step 3: Installed Psychological Safety Rituals

We started every weekly sync with this:

“What’s one thing we’re pretending is fine that actually isn’t?”

First week? Awkward silence.
Second week? A PM quietly called out a scope shift that no one had addressed.
By week three? They were surfacing issues before they metastasized.

The Result: From Defensive to Decisive

Within six weeks:
– Time to decision dropped by 60%
– Cross-team conflict was still present, but now it was productive
– Morale scores jumped 18% (yes, they measured it)
– Most importantly: they launched a feature that actually worked and was market-ready on day one

No heroics. No reorganisation.
Just clear incentives, honest rituals, and structural permission to move.

Leading Through the Mess (Without Getting Swallowed by It)

Let’s retire a myth once and for all: Being a strong leader doesn’t mean having all the answers.
It means knowing what questions to ask when everything feels stuck, misaligned, or quietly falling apart behind high-functioning optics.

Because here’s the truth: Mess isn’t the enemy. Avoidance is.

The best leaders I know aren’t the ones who never deal with dysfunction.
They’re the ones who know how to step into it with:
– Precision instead of panic
– Curiosity instead of ego
– And a toolkit that balances system redesign with human insight

What actually changes when you lead this way?

You stop treating teams like productivity units.
You start seeing them as dynamic systems, where clarity, trust, and structure are interdependent.

You stop over-rewarding heroics.
You start designing environments where heroics aren’t needed.

You stop managing for appearances.
You start managing for flow, the state where people move fast because the path is visible, supported, and shared.

As a leader, your job isn’t to control outcomes.
Your job is to build systems where good outcomes become more likely, more often, with less friction and more trust.

That’s what it means to lead through the mess. Not with noise. Not with optics. But with clarity, stability, and the kind of emotional posture that makes the real work safe to do.

Recap: Your Anti-Dysfunction Playbook

Here’s what we’ve unpacked:

– Dysfunction is signal, not failure
– Most gridlock lives in the space between roles, not within them
– Culture is built through consistent micro-behaviors, not grand gestures
– Restructuring should create movement, not bureaucracy
– Case studies don’t need to be perfect, they need to be replicable

And most importantly?

You can lead well without waiting for perfect conditions.

You just have to be the one who names the friction, decodes the pattern, and builds the system that flows.

What’s the messiest team or organisation challenge you’ve ever stepped into?

What shifted, and what did you learn from it?

Share your fixer stories.
Or drop your go-to playbook move for turning dysfunction into alignment.

Because behind every thriving company is someone who made it work better, quietly, strategically, without waiting for permission.