Hi Reader, A few weeks ago I made you a promise. I said I was turning something we'd been building together into a tool you could actually use. I said CFW readers would get it first. That's today. The Systems Investment Playbook is the exact process I used when I had five builds on our list and no good way to choose which one went first. One build that quarter. No more debate. The gift officer who was managing 1,000 prospects manually is now working a portfolio of 50 — the other 950 in...
about 7 hours ago • 1 min read
You Can't Systematize This One Issue #414-minute read Hi Reader, Last April, budget season handed me a gut punch. My CEO and CFO have watched us grow 69% without adding a single frontline fundraiser. They believe in the model. And then the revenue goal for the new fiscal year landed. Revenue target: up. Headcount: same. Strategy conversation: not on the agenda. They didn’t do it to be dismissive. They did it because that’s how budget math works. Revenue must grow. Expenses need to stay flat....
2 days ago • 3 min read
The System That Keeps Strategy Alive Issue #404-minute read Hi Reader, I realized something uncomfortable. If I stepped away, our execution would soften. The team would keep working. Meetings would still happen. Revenue would come in. But the strategy would drift because it lived in my head. Not in the system. We didn't have a scorecard. We didn't have a planning rhythm that the whole team could see. We had instinct. That's how a lot of development operations run. The leader isn't weak. The...
9 days ago • 3 min read
Your Forecast Won't Warn You Issue #394-minute read Hi Reader, Two years ago, we learned something the hard way. A corporate donor surprised us by deciding not to renew a seven-figure partnership. By the time it hit the dashboard, the window for recovery was already closing. The system wasn’t broken. It just didn’t warn us. Most fundraising dashboards are built to measure what happened. Very few are built to surface where you’re exposed. That difference matters when conditions change. Why...
16 days ago • 2 min read
Your Portfolio Is Shaping How Your Team Thinks Issue #384-minute read Hi Reader, Last week, I asked why board connections stall. A — They don't know the prospect well enough and won't admit it. B — They know them, but the ask feels too risky. Here's what those of you who replied said: mostly A. Board connections stall for the same reason portfolios stall. Wrong design. Not wrong people. Let's start with a question. What is your portfolio actually built to produce? Revenue - of course. But, is...
23 days ago • 3 min read
System Nine: Board Leverage Issue #374-minute read Hi Reader, Last week, I asked whether you absorb the CEO's mid-quarter requests or stall for time. I only heard back from one person — and that tells me something. Either the question didn't land, or the answer felt too uncomfortable to put in writing. I've been in both places. So I'll answer it myself. My default used to be absorb. Every time. And it cost me before I built a system that gave ideas somewhere to land. That's what last week's...
about 1 month ago • 3 min read
The Monday Email That Breaks Good Plans Issue #364-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...
about 1 month ago • 3 min read
How to Complete Your Strategic Priorities Issue #353-minute read Hi Reader, Your annual plan is solid. You know which systems to build. You have the budget and the team buy-in. And then Q2 ends. Only half of your priorities shipped. You were buried. Urgent donor calls. Board prep. Event planning. Forty-seven other things that felt critical in the moment. This is the gap between annual planning and actual completion. The fix isn’t better time management. It’s System Seven: Quarterly Planning —...
about 1 month ago • 2 min read
Which System Do You Build When You Can Only Build One? Issue #343-minute read I could build five systems right now. Each one would add $2M-$5M or more in revenue capacity over the next three years. But I can’t build them all at once. Between staff capacity, training requirements, budget approvals, and my own bandwidth, doing everything is a recipe for doing nothing. So the real question isn’t what we should build. It’s what do we build first. This is System Six: Systems Investment — deciding...
about 2 months ago • 3 min read