The 2026 Planning Question You're Missing
Issue #025
This week's strategic brief (3-minute read)
Hi Reader,
You're close to finalizing your 2026 plan. Your revenue targets are set, initiatives are mapped out, and direct appeals are scheduled.
But before you call the plan final, there’s one question most chief fundraisers never ask.
It's not "What do we want to achieve?" (That's easy.)
The question is:
What infrastructure do we need to make this plan work?
Skip it, and your bold goals may become mid-year regrets.
The Planning Trap I Fell Into
Early in my career, I would walk into the new year feeling proud of our plan.
Ambitious revenue. Solid initiatives. Clear timeline. I thought we had it all figured out.
By summer, reality had other ideas.
Projects stalled for no clear reason. Strategy was shoved aside by fires to be put out.
And despite everyone’s best effort, momentum kept stalling. It took me a while to admit the truth. The plan wasn't flawed. The foundation was.
My old approach was to dream big, add even more initiatives, and hope for the best.
That approach sets you up for mid-year rework, friction, and burnout.
The strategic plan was never the barrier.
The missing systems were.
Infrastructure: The Key to Growth
Last week, we unpacked the "hidden taxes" killing momentum: coordination drag, bottleneck backups, and leadership overload.
These aren't random frustrations. They're symptoms of absent systems.
Your 2026 plan quietly assumes these exist:
- A Pipeline Stability System for predictable growth.
- A Team Autonomy Protocol to take decisions off your plate.
- An Internal Alignment OS to kill cross-team chaos.
- A CEO Partnership System that withstands transitions.
Most teams are missing two to three of these systems. Some are missing all of them. When you finalize a plan without checking the underlying conditions, you’re not planning.
You’re forecasting hope.
The One Question That Rewrites Everything
Pause your 2026 draft. For each priority, ask:
"What must be true for this to succeed?"
If your answers sound like:
- "Tighter team coordination"
- "Real-time data dashboards"
- "Early CEO buy-in"
- "Streamlined cross-dept workflows"
Those aren’t tasks. They’re system gaps.
And those gaps are your real priorities.
A quick example:
If your plan relies on significant corporate revenue growth but you don’t yet have a qualification method, sequencing strategy, or prospecting OS for corporate leads?
You don’t have a corporate fundraising plan.
You have a wish.
The Mindset Shift
When you look at your nearly-final 2026 plan, don’t ask:
“What are we trying to do?”
Ask instead:
“What are we assuming exists — and does it actually exist?”
If 40% or more of your priorities rely on systems you don’t have, don’t trust, or have outgrown, the issue isn’t your plan.
It’s your mental model.
Planning isn’t about forecasting activity.
My role as chief fundraiser is to engineer the conditions that make success inevitable.
Coming Next Week
Next Sunday: Before 2026 begins, three checkpoints to help you audit your operating system.
Starting January 4, we'll build all 12 fundraising systems together. We'll do one each week using plug-and-play frameworks.
Your Turn
Before you finalize your plan, try this 10-minute exercise:
- Pick your top three 2026 priorities.
- For each, list what must be true operationally for it to succeed.
- Circle anything that doesn’t exist today.
- That circled item?
That’s your real Q1 priority.
If you’re stuck or want another set of eyes, hit reply. I’m here, and I read every note that comes in.
Until next week,
Christine
P.S. Top fundraisers don’t rely on hope. They rely on systems that make success inevitable.
