The Chaos Looks the Same Every Time
Let me guess:
Your leadership meetings go in circles.
Your team’s OKRs exist… somewhere in Notion.
Your founder is still signing off every decision, three layers deep into operations.
You’re not alone. I’ve worked with dozens of leadership teams in scale-ups, PE-backed businesses, and first-time founder orgs—and the pattern is almost always the same. The names change. The chaos doesn’t.
Here’s what I see constantly—and what I’ve done as a Chief of Staff to fix it.
🚩 Problem #1: The Endless Debate Loop
What it looks like:
You’re in your fourth meeting on the same topic. Everyone has opinions. No one makes a call.
By the end of the meeting, you’ve got 10 Slack threads, a Figma file, and a shared doc—but still no decision.
Why it happens:
• No single point of accountability
• Fear of making the “wrong” choice
• Leadership team dynamics (too much consensus-seeking, not enough clarity)
What it costs you:
🚨 Execution paralysis
🔁 Burnout from constant context switching
🧨 Missed commercial opportunities
🔧 How to Fix It: Run a Decide & Own Sprint
Every leadership meeting should answer:
What decision needs to be made? (No more “just discussing”)
Who owns it? (One person. Not a committee.)
What’s the next step? (With a deadline)
What gets communicated to the rest of the business? (Execution needs clarity down the chain)
💡 Pro tip: Add a “Decision Audit” column to your next 1:1 or leadership sync. Track decisions left open for more than 2 weeks—and why. That’s where your real work is.
🚩 Problem #2: OKRs That Don’t Drive the Business
What it looks like:
Your team has quarterly OKRs… but you’re halfway through the quarter and no one can tell you what they are.
Or worse—they know them, but they’re not using them.
Why it happens:
OKRs are disconnected from day-to-day work
They’re too vague (“be more efficient”)
They’re written like aspirations, not operational goals
What it costs you:
🌪️ Misalignment between leadership + teams
🫠 Prioritisation chaos
💸 Wasted energy on “low leverage” work
🔧 How to Fix It: Make OKRs Your Operating System
Try this next quarter:
1. Rewrite all company OKRs using this formula:
“We will [measurable goal] by [doing something operationally real] to impact [customer/revenue/risk].”
Example: We will reduce churn by 15% by implementing a new onboarding sequence that launches in April.
2. Tie every leadership 1:1 to OKRs.
Ask: “Which KRs are you closest to? Which feel blocked?”
3. Add OKR review to your team’s rituals.
Fortnightly = rhythm. Quarterly = irrelevance.
💡 Pro tip: Assign each OKR a “business owner” who’s responsible for escalating blockers to the leadership team weekly.
🚩 Problem #3: The CEO Bottleneck Spiral
What it looks like:
Your CEO is still across everything: ops, hiring, decks, product decisions, even reviewing email copy.
They’re exhausted. Or even worse, they're pretending not to be and letting their tension out on everyone around them. And the team is frozen.
Why it happens:
The business scaled faster than systems did
Lack of trust in the team
There’s no operating model to support real delegation
What it costs you:
⏳ Founder burnout
❌ Delayed decisions at every level
💥 Inability to scale revenue-driving teams
🔧 How to Fix It: The 3-Month Delegation Sprint
Month 1:
CEO tracks every decision they touch.
Identify categories: ops, hiring, product, external, fire-fighting.
Month 2:
Assign categories to the right leaders (and make those assignments public)
Add documentation + approvals to reduce Slack panic
Month 3:
CEO steps back from 50% of decisions.
Let something break. Seriously. That’s how you find where you need new structure—not where the CEO needs to “just keep doing it.”
Pro tip: Run a “Bus Test.” Ask: If the CEO went offline for 7 days, what wouldn’t happen? That’s your CoS focus list.
💥 The Real Talk: Execution Is Leadership, Not Logistics
These patterns don’t occur because your team’s bad.
They happen because no one has made execution their job.
That’s what I do.
I come in as a Fractional Chief of Staff and:
Build leadership operating models
Run execution sprints
Align strategy, team priorities, and internal comms
Clear the bottlenecks without turning your startup into a corporate machine
✨ Want Help With This?
If your team is stuck in cycles of chaos, misalignment, or under-execution—
You don’t need more ideas. You need structure.
📩 DM me to find out how we can work together
Let’s get this thunder rolling.