Behind the Clipboard: Strategy’s Side of the Story
Welcome to “Behind the Clipboard,” a satirical talk show where the guests are the very real challenges nonprofit founders face—and the conversations are honest, hilarious, and just a little too relatable.
Each “episode” features a fictional character—like Burnout, Mission Drift, or Strategy—getting interviewed by your host (that’s me!) in a mock talk-show setting. But beneath the humor? A real issue we need to talk about.
This series blends humor and insight to help you name what’s really going on in your nonprofit—and what to do about it—without the guilt, fluff, or burnout.
Cue the dramatic music and an overstuffed file folder being slammed on the desk.
Today on Behind the Clipboard, we’re bringing out a guest who knows exactly what went wrong, but no one wants to listen to them until the crisis hits.
Please welcome… Strategy.
🛋️ The Interview
Host (me):
Strategy, welcome to the show. You’ve had a rocky relationship with a lot of nonprofits. What’s going on?
Strategy (in a sharp blazer, holding a clipboard):
Let’s just say I’m tired of being a one-night stand. People love me in January. I’m hot stuff when they’re making vision boards. But by March? They’ve already moved on to event panic and grant deadlines.
Host:
Do you feel like you’re being used?
Strategy:
Absolutely. They draft me, print me, and never look at me again. I’m more neglected than the organization’s Facebook page.
Host:
What would you say to the people who claim they “just don’t have time for planning”?
Strategy:
I’d say that if you don’t have time to plan, you’re going to waste twice as much time fixing the mess later.
And honestly? I’d like a little respect. I keep the mission on track, the programs aligned, and the board out of your hair.
🎯 What This Looks Like in Real Life
Not prioritizing strategy doesn’t always look like chaos right away. But over time, the cracks start to show:
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Random program launches with no clear connection to your mission
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Fundraising goals that shift based on how people feel this month
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Teams working hard in opposite directions
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You wondering why everything feels reactive instead of intentional
You might even hear people say, “We need to be more strategic”—but no one defines what that means.
Here’s the truth: thinking strategically means pausing to ask,
“Does this decision move us toward our mission and current priorities—or just fill space?”
Being strategic is less about a giant binder and more about choosing the next right step on purpose.
Strategy isn’t about locking yourself in a room with a whiteboard. It’s about giving your organization a shared language, direction, and focus.
🛠️ What To Do About It
Let’s bring Strategy back into your organization, without making it overwhelming.
1. Set a Review Ritual
Pick a day each month to revisit your plan. No edits, no pressure—just reading it. That alone can reconnect your team to the bigger picture.
2. Prioritize 3 Things at a Time
Strategy doesn’t mean do everything. It means do the right things. Keep it focused by choosing just three organizational priorities per quarter.
3. Share the Strategy
Get it out of your head and into meetings, staff check-ins, board updates—anywhere people need clarity. Strategy is a team sport.
4. Treat It Like a Living Document
You’re allowed to change the plan. Strategy is guidance, not a prison sentence. You can pivot and still stay grounded.
💬 Final Thoughts from the Couch
Strategy (crossing arms):
I’m not here to control everything. I’m here so you don’t get lost in the weeds.
Host (me):
Fair. No one likes a reroute halfway through the year.
Planning isn’t about being rigid—it’s about being ready. And when you bring Strategy back into the room? Everything works better.
Even the budget.
