The Monday Email That Breaks Good Plans

Issue #36
4-minute read

Hi Reader,

Your Rocks are set. Your team is aligned.

Then Monday happens.

Your CEO emails about a donor she met Saturday night. She wants to move on it this week. It feels urgent.

You know what’s at stake if you say yes. You also know what’s at stake if you hesitate.

This isn’t a CEO problem. It’s a systems problem. And it’s the most common reason well-planned quarters fall apart.

The Gap Nobody Talks About

Most chief fundraisers handle CEO ideas in one of two ways.

They say yes immediately. They drop what they’re doing and spend a week chasing a lead that may or may not go anywhere. The quarter slips.

Or they push back. The CEO feels dismissed. The relationship takes a hit.

There’s a third way. And it requires System Eight in the Chief Fundraiser Operating System.

What This System Actually Does

A CEO partnership is not about managing up. It’s about creating a predictable place for new ideas to land.

Here’s what it looks like in our shop.

I meet with our CEO every two weeks for 50 minutes. Not to report. To align.

Three things on the agenda. Every time.

1. What’s in flight this quarter
2. What he’s hearing from donors, board members, or the field
3. What needs his involvement in the next two weeks

That third item changed everything.

When he knows where his attention is needed, he generates less reactive work.

When New Ideas Arrive Anyway

They will. That’s just part of leadership.

So I’m building something simple: an Opportunity Register.

It’s a shared document so every new idea lands here instead of in my inbox or in my team’s queue. It does not automatically touch our Rocks.

At the next quarterly planning cycle, we’ll scan the Register together. I’m betting some ideas will still be live. Most won’t. A few will probably become our biggest wins of the year.

I haven’t run a full quarter with it yet. But it’s already helping me manage new ideas that have come up.

It protects the quarter. And it protects the relationship.

That’s the point.

Three Things to Test This Week

If you don’t have a CEO alignment meeting on the calendar:

• Schedule one. Biweekly. At least 30 minutes.

• Send a one-page summary of your current Rocks before you meet.

• Start an Opportunity Register. Name it, share it, and put the next idea there instead of putting it into motion.

If you already meet regularly, ask yourself honestly:

Are you spending most of the time updating your CEO or aligning with your CEO?

The difference is bigger than it sounds.

On My Radar

What I’m reading, using, or thinking about this week.

What I’m reading:$100M Leads by Alex Hormozi.

It’s a book on lead acquisition. Not a fundraising book. That’s exactly why I’m reading it.

We have 950 major donor prospects that our team cannot personally manage. For a long time, I called that a capacity problem.

Hormozi’s framework is forcing me to see it differently: it’s a demand generation problem. We’re not short on people. We’re short on a system that moves prospects through a pipeline without requiring individual attention at every step.

I’m halfway through. It’s already changing how I’m thinking about our engagement funnel.

If you’re sitting on a list your team can’t touch, this might reframe the problem for you, too.

Coming Next Week

Your CEO isn’t the only person with power who brings new ideas mid-quarter.

Next Sunday: System Nine — Board Partnership. How to turn your board from a compliance burden into a revenue multiplier.

Your Turn

Quick one. When your CEO brings you a mid-quarter idea, what's your default?

A — Absorb it. Figure out how to fit it in.

B — Stall. Buy time while you assess the impact.

Hit reply with A or B. One letter is enough.

Next week I'll share what the pattern looks like across readers and why neither answer means you're doing it wrong.

Until next week,
​Christine​

PS: I’m building the Opportunity Register right now, and I’ve drafted a one-page template to start from. Reply with “Register” and I’ll send it to you. Use it. Break it. Tell me what’s missing.

PPS: Starting this week, I’m adding “On My Radar” to every issue. This is what I’m reading, using, and thinking about.

Chief Fundraiser Weekly goes out every Sunday for chief fundraisers building from $10M to $25M. If someone forwarded this to you, I hope you'll consider subscribing.

I’m Christine Bork, Chief Development Officer at the American Academy of Pediatrics. I write Chief Fundraiser Weekly to share what I’m learning as I lead a growing team and try to do the work in a way that’s sustainable and thoughtful.