Issue #002
This week’s strategic brief (3-minute read)
The Hard Thing About Being a Chief Fundraiser
It’s not the fundraising.
I asked 12 chief fundraisers what’s stealing their time.
75% said they spend 60–80% of their time on tactical work.
Why?
Because leading through complexity is harder than doing what we’ve mastered.
It’s grant reports.
It’s burnout and backfill.
It’s “just jumping in to fix it.”
But underneath all that?
It’s fear. The fear of getting leadership decisions wrong.
The Hard Thing is Leading When:
- Your board wants growth, but won’t invest in infrastructure
- Everyone expects you to solve problems you’ve never faced
- You must choose between major gift cultivation and operational stability
The brutal truth:
The work that got you to $10M won’t get you to $25M.
Why Strategic Leadership Feels Impossible
Three fears show up for nearly every chief fundraiser I know (including me):
- Fear of being exposed:
“What if the board realizes I don’t know how to scale this?”
- Fear of disappointing:
“What if I can’t deliver on the growth projections I agreed to?”
- Fear of choosing wrong:
“What if I hire the wrong person and set us back two years?”
These fears are normal. They show up for every chief fundraiser stretching beyond their comfort zone.
The Strategic Decision Framework I Use
When I’m stuck in a lose-lose scenario, I fall back on this 3-step system. I try to move fast when I can (within 48 hours) to avoid the sleepless nights of indecision:
- List your non-negotiables
(Mission alignment, values, legal or reputational boundaries)
- Define what you can live with long-term
(How will this impact culture, growth, or stakeholder trust in 3 years?)
- Make the call and communicate your reasoning
(Upward to the board, downward to your team, sideways to peers)
Real Example: When One Donor Wants Too Much
Right now, I’m managing a high-stakes challenge.
A major donor seeks exclusive access to a highly placed member of the senior leadership team to obtain inside information.
But two other $1M+ donors also need that level of engagement.
I applied the framework:
- Non-negotiable: All donors deserve equitable, values-aligned stewardship
- Long-term concern: Exclusive access sets a dangerous precedent
- Decision: Developed a limited, structured rotation where the senior team member meets virtually and only as needed
Why this framework works:
- Forces clarity: Naming non-negotiables prevents emotional decision-making
- Considers precedent: Long-term thinking stops short-term relationship fixes that create bigger problems
- Enables communication: Clear reasoning helps explain decisions to all stakeholders
Next steps: I'll implement the rotation system over the next 30 days and track how all parties respond to the structured approach.
The Truth About Executive Decision-Making
Strategic growth means disappointing someone.
Your team wants stability.
Your board wants growth.
Your CEO wants certainty.
Your donors want attention.
You can’t please everyone. But you can lead them through it.
Build your systems for:
- Upward communication: Frame decisions in strategic context
- Downward communication: Share rationale without airing every tension
- Stakeholder management: Stay connected—even through tough calls
My Go-To Communication Script
When I roll out a difficult decision, I rely on this 4-part script:
- Context: “Here’s the strategic situation we’re facing…”
- Criteria: “Here’s how I’m evaluating the options…”
- Conclusion: “Here’s why this decision supports our long-term mission…”
- Next steps: “Here’s what happens in the next 30–60–90 days…”
It brings clarity.
It shows leadership.
And it keeps your team aligned, even when the stakes are high.
Scale Check: Are You Making Strategic Decisions?
Ask yourself:
- Do I have a consistent framework for evaluating competing priorities?
- Can I explain my decision criteria without defensiveness?
- Do I track the outcomes of my strategic choices as learning moments?
If you answered “No” to any, you’ve just identified your next leadership development opportunity.
If you answered “Yes” to all three, well done. You’re operating at the strategic level your organization needs.
Coming Next Week
The Team Structure That Actually Scales
The specific roles and reporting relationships that work after $10M, based on real lessons I’ve learned building our current team.
I'd Love to Hear From You
What’s the hardest leadership decision you’re facing right now?
Reply to this email. I read every response, and I'll try my best to help.
Until next week,
Christine
P.S. Help me shape what I write next. Take my 3-question insight survey. It only takes 2 minutes. Your input directly shapes future issues.
