Questions to Ask Before Strategic Planning
I've watched this happen at more than one retreat: the room comes in ready to celebrate, but by mid-morning board members, staff, and volunteers are still working out how those wins add up to real progress on the plan. There's usually a dashboard somewhere, yet not much connecting the stories people are proud of to the numbers on it, and I find myself thinking that link should have been made before anyone sat down, because it's hard to build consensus on priorities when you aren't sure where you stand. So the first half of the day goes to catching up instead of deciding.
That catching up should happen months before the retreat, and most of what you need is already in people's heads. Meanwhile, the organization is planning anyway. Every budget line that rolls forward and every program that continues because ending it feels wrong is a strategic decision, just not one anyone is making on purpose. The fastest way to surface those decisions is to ask.
Hold Stakeholder Interviews Before Strategic Planning
This fall, talk to 10 to 15 people one at a time: board officers, staff two levels down, someone who left, your biggest funder, a partner who told you no. Ask them all the same five questions:
What is this organization genuinely great at?
What do we keep saying we'll fix and never fix?
If we disappeared tomorrow, who would notice first?
What decision is everyone avoiding?
What would make you stop supporting us?
Pay the most attention to question four. Around the eighth conversation, you'll hear the same answer in different words. That's usually the center of your plan.
Sort what you heard into themes, pair it with a few honest numbers (revenue by source, real program costs, turnover), and send the board the one to three decisions the plan has to settle before the holidays. The retreat then goes to deciding instead of catching up.
One Step This Week
Email three board members one question: What decision does this organization keep avoiding?
If their answers line up, you're ahead. If they don't, that may be part of why the last plan didn't stick.
Heading into planning season?
I'm offering 8 free Strategic Planning Readiness Reviews this fall: 45 minutes and a written, scored one-pager your board can use. Apply here!
