18 DAYS AGO • 2 MIN READ

The simplest planning exercise for 2026

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Chief Fundraiser Weekly

You don’t need more content. You need room to think and someone who understands the role. Chief Fundraiser Weekly is a short Sunday executive brief with one system to try and space to ask what comes next.

The Three Questions That Will Define Your 2026

Issue #027

This week's strategic brief (2-minute read)

Most chief fundraisers will spend this week finishing elaborate plans for 2026.

I'm not.

After 30 years of running end-of-year planning cycles, I've found that the best way to start a new year is with three simple questions.

These questions will show if 2026 is just another year of reacting or the year when your time, team, and decisions align with what matters most.

1. What's the one thing holding everything else back?

Every operation has one bottleneck that slows everything.

For me, in 2024, it was our prospect research process. Every major gift strategy was held up by a research bottleneck. Until we fixed that, nothing else could move faster.

You probably already know what your bottleneck is. You've just been too busy managing around it to fix it.

2. Where would your operation break if revenue suddenly doubled?

This isn't a hypothetical scenario. It's a diagnostic test.

When our revenue grew by $10M, our donor cycle and portfolio management processes struggled to keep up.

Where's the weak point in your operation? Is it proposal production capacity, portfolio load, or board reporting systems? Figuring this out will tell you where to invest in 2026 before growth forces the issue.

3. How much of your time will be spent on strategic work in 2026?

Be realistic, not aspirational.

I look for ways to design my calendar to add more strategic time. This year I reduced three recurring meetings and delegated two approval processes I didn't need to own.

Most chief fundraisers say they want more of their time to be spent on strategy. Your team can't operate strategically if you're still modeling a tactical week.

Your Turn

Open a blank page and write down your answers to these three questions. Then, circle the one that feels most urgent. That's your starting point for 2026.

Coming Next

These three questions will give you clarity. What you do with that clarity is where progress happens.

Starting next Sunday, I'm launching System Zero: Hidden Constraints, the foundation of the Chief Fundraiser Operating System. We’ll build it together over 13 weeks.

One system each week. Practical, repeatable, ready to use.

Question for You

Before you go, I’d love your quick take. Would you take five seconds to answer this question?

If you’re wrestling with something specific, just hit reply and tell me more. I’ll help you think it through.

See you next week,
Christine

P.S. If one of these questions made you uncomfortable, trust that signal. It's pointing to the place where a slight shift will create the most movement in 2026.

I’m Christine Bork, Chief Development Officer at the American Academy of Pediatrics. I write Chief Fundraiser Weekly to help other fundraising leaders escape the chaos and build high-performing, strategy-first operations.

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Chief Fundraiser Weekly

You don’t need more content. You need room to think and someone who understands the role. Chief Fundraiser Weekly is a short Sunday executive brief with one system to try and space to ask what comes next.