Fixing a Dysfunctional Leadership Team: The CEO's 90-Day Playbook

Read Time: 3 minutes.

The Reality Check

Your leadership team is broken. Meetings are political theater. Decisions get relitigated in hallways. People protect territory instead of pursuing outcomes.

Here's the hard truth: A dysfunctional leadership team is a tax on every person, initiative, and decision in your company.

This isn't a "when we have time" problem.

This is your real work as CEO.

Note: Even if you’re not a CEO, this playbook works for any team where power and politics are crowding out purpose and performance.

Step 1: Diagnose the Scope (Week 1)

Is This a Must-Solve Problem?

Ask yourself: If fixing your leadership team always takes a backseat to "real work," nothing will change. Be brutally honest—is this worth solving or not?

If yes, commit fully. Half-measures create half-a$$ed results.

What's Your Role in the Dysfunction?

You hired these people. Or inherited them and changed nothing. Or tried ineffectively for months.

Own your part first. If you can't see yourself clearly, you won't see the full problem clearly either.

Is the Problem Narrow or Broad?

NARROW (One Person):
The choices are simple—recovery or removal. Have a direct conversation: get better fast or get out. Set a 30-day timeline. If they can't or won't change, make the change for them.

BROAD (Normalized Dysfunction):
You have three typical root causes to address systematically. Which brings us to…

Step 2: Identify the Root Cause (Week 1-2)

Root Cause 1: POWER

The Problem: Status games overshadow the mission. Leaders protect territory instead of pursuing outcomes.

The Fix:

• Eliminate fiefdoms through single-thread accountability

• Make collaboration a KPI, not a suggestion

• Restructure reporting to prevent empire-building

Root Cause 2: INCENTIVES

The Problem: Your compensation rewards individual performance over team outcomes. You're literally paying people to be dysfunctional.

The Fix:

• Tie meaningful compensation to collective goals

• Reward leaders who make others better

• Make it expensive to be a lone wolf

Root Cause 3: CULTURE

The Problem: Normalized behaviors (heroics, aggressive communication, conflict avoidance) no longer serve the mission.

The Fix:

• Name the toxic behaviors explicitly

• Define 3-5 non-negotiable standards

• Remove people who violate them repeatedly

Our Next Free Workshop for Playbook Readers

Step 3: Set the New Standard (Week 2)

Call the "Day One" Meeting

• Name what's broken explicitly

• Write it down and date it

• Declare the old way is over

• This isn't another initiative, it's the new OS

Define Non-Negotiable Behaviors

Vague calls for "better collaboration" won't work. Get specific:

Examples:

• "We debate in the room, then commit publicly"

• "No gossip. Issues go direct to the person involved"

• “We share full credit and own our mistakes fully"

Post them. Reference them. Reward them. Enforce them.

Step 4: Install Accountability Systems (Week 3-4)

Create Systems to Support Opting In

Dysfunction thrives in ambiguity. Install systems that surface reality:

• Real-time feedback tools

• Public scorecards on team performance

• Regular retrospectives with actual consequences

Give People an Easy Exit for Opting Out

Some people won't want to change. Give them 30 days to opt out with dignity and a reasonable package.

No shame, no blame. Just clarity that the new way isn't for everyone. The people who stay are opting into your new standard. Hold them accountable to it.

Step 5: Model the Change (Ongoing)

You Can't Delegate Culture Change

• Want vulnerability? Be vulnerable first

• Want direct feedback? Give it and receive it publicly

• Want collaboration? Show them what it looks like

Your leadership team watches your every move.
Your behavior sets the ceiling for theirs.

Step 6: The 90-Day Checkpoint

Measure Dramatic Improvement

Set a 90-day checkpoint. Are things dramatically better?

If yes: Celebrate and reinforce the new behaviors.
If no: You haven't been decisive enough.

Either:

• The wrong people are still here, or

• You're tolerating behavior you said you wouldn't

This is your moment of truth.

The Hard Choices

The Recovery Conversation

"Your behavior is inconsistent with our leadership standards. You have 30 days to demonstrate sustained change. Here's specifically what that looks like..."

The Removal Decision

When someone can't or won't change: "This role requires [specific behaviors]. You've shown you can't consistently deliver that. Let's discuss your transition."

The Team Reset

Sometimes you need to remove multiple people simultaneously. Better to have a smaller, functional team than a larger, dysfunctional one.

Your Next Move

This week:

1. Honestly assess if this is worth solving (if not, stop reading)

2. Identify your role in the dysfunction

3. Diagnose if the problem is narrow (one person) or broad (systemic)

4. Schedule the "Day One" meeting

Remember: Fixing a broken leadership team requires hard conversations and harder choices. That's your job as CEO.

If you're not willing to have those conversations and make those choices, you're not leading. You're enabling the dysfunction.

The question isn't whether your leadership team can change.
The question is whether you will lead them through it.

6 Month Update: Dave vs dAvId The Rematch

Last April, I snuck out a close victory over my AI Clone. But AI is changing fast. We’re going to check in and see how it’s progressing in stealing my job.

Hit reply on this note and give me some real leadership challenges for the two of us to square off against. You’ll get to vote on the winner.

Note: Your issues will be anonymous. Free coaching (times two)!

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Thank you for reading. Appreciate you!

Dave