What Your Board Should Actually Be Asking About Teacher Retention
Board meetings on staffing tend to follow a predictable pattern.
How many positions are unfilled? What's our recruitment timeline? Are we competitive on salary?
These questions aren't wrong. But they focus on the symptom—vacancies—while often missing the disease: why teachers leave, and what would make them stay.
Better questions lead to better retention. Here's where boards should be pressing.
"What Does a Typical Day Actually Look Like?"
Most board members haven't spent meaningful time in a teacher's daily reality. They remember school from their own experience—which is decades out of date—or they see carefully orchestrated visits that don't represent ordinary conditions.
The gap between how boards imagine teacher work and how teachers actually experience it is enormous.
Teachers today manage complex data systems, navigate multiple disconnected platforms, respond to communication channels that never close, differentiate instruction for increasingly diverse classrooms, and document everything for compliance purposes—all while teaching.
Understanding retention requires understanding burden. Boards should ask for honest accounts of daily teacher experience, not sanitized summaries.
"What Would Make Our Best Teachers Stay Five More Years?"
Retention conversations often focus on struggling staff or potential departures. They rarely focus on thriving teachers.
Your best teachers—the ones everyone wants to stay—know exactly what's working and what isn't. They see the friction points clearly. They know which systems help and which hinder.
Ask them directly: what would make you confident you'll still be here in five years? What would make you hesitate? The answers are usually specific, actionable, and different from what administrators assume.
Your best teachers are also the most mobile. Other schools want them too. Retention strategy should prioritize their experience, not just at-risk staff.
"How Do Our Systems Create or Reduce Teacher Burden?"
Every tool, process, and requirement either makes teaching easier or harder. There's no neutral.
Boards should ask for honest audits: which systems do teachers appreciate? Which do they work around? Which create more work than they save? Are our tools integrated, or do teachers manually move information between platforms?
This isn't about cutting budgets or eliminating tools. It's about understanding the cumulative effect of decisions that seem small individually but combine to create the daily reality teachers experience.
Burden compounds. Relief compounds too. Knowing which direction you're heading matters more than any single decision.
"What Are We Measuring That Actually Predicts Retention?"
Exit interviews tell you why people left—after it's too late. Turnover rates tell you what happened—after it happened.
Better metrics predict rather than report. Teacher engagement surveys, if done honestly. Time studies showing where teacher hours actually go. Comparison of planning burden across buildings. Adoption rates for district tools and platforms.
Boards should push for leading indicators, not just lagging ones. By the time turnover spikes, the problem has been building for years.
The Deeper Question
Ultimately, boards need to ask: have we designed a system where excellent teaching is sustainable?
Not possible—sustainable. Can someone do this job well for decades without burning out? Can they have lives outside work? Can they maintain the passion that brought them to teaching?
If the honest answer is no, retention programs are bandaids. The structure itself needs examination.
At Lamppost, we believe educators deserve systems designed for sustainability—where planning tools reduce burden instead of adding it, where technology serves teachers instead of demanding service from them.
Because the best retention strategy isn't programs or incentives. It's making the job worth staying in.
Onward and upward,
—JBJL
