How I Plan My Quarters Like a CEO (And Why Most Plans Fail)

Most business owners don’t fail because they’re lazy.They fail because they’re busy.

That’s exactly why I hosted my recent YouTube session, “Plan Q1 With Me.” I wanted to pull back the curtain and show you how I actually think about quarterly planning as a CEO running real businesses — not just a pretty planner and a wish list.

Here’s the big shift that changes everything:

CEOs don’t ask, “What should I do?”

We ask, “What must be true by the end of this quarter?”

That question forces clarity. It moves you out of task mode and into results mode.

The CEO mindset

Employees think in terms of tasks.CEOs think in terms of outcomes.

When I plan a quarter, I don’t start with a to-do list. I start with a destination. I decide what needs to exist, be built, be launched, or be stabilized by the end of the quarter. Only after that do I work backward into actions.

If you skip that step, your calendar fills up…but your business doesn’t move forward.

Why most quarterly plans fail

I see this over and over:

People create these massive, unrealistic lists with 20–30 “priorities.”That’s not a plan — that’s overwhelm.

When everything is important, nothing is.

Real progress comes from focus. In my world, I limit every quarter to three real priorities. Not goals. Not ideas. Priorities.

These are the three things that, if they get done, make everything else easier.

What a real priority actually is

A real priority removes a bottleneck.

It might be:

• Getting your marketing system in place

• Filling your first (or next) house

• Hiring or delegating something that’s holding you hostage

• Fixing a financial leak

A priority should create momentum, not just check a box.

If it doesn’t meaningfully change how your business operates, it’s probably just a task.

Execution is where CEOs separate themselves

Planning is easy. Execution is where most people fall apart.

That’s why I don’t just write goals — I build accountability into my quarter. I do weekly CEO check-ins. I assign ownership. I use frameworks like DARCI so everyone knows who is driving what.

If you don’t review your plan weekly, you don’t have a plan.You have a document you once opened.

Quarterly planning isn’t about doing more.

It’s about doing the right things — in the right order — with intention.

That’s how I run my group homes.

That’s how I run Group Home on Autopilot.

And that’s how I help my clients stop spinning and start building.