10 strategic questions to pressure-test your 2027 benefits strategy

Healthcare costs are expected to keep climbing through 2026 and into 2027, intensifying pressure on employers to contain spend while improving outcomes and simplifying an increasingly crowded vendor landscape. Planning season is the moment to pressure-test whether your current strategy is built for that reality — or whether hidden risk is compounding beneath the surface.

This guide provides 10 strategic questions to bring into your planning sessions, along with insight on what a strong answer should include for each. It covers where the biggest cost-containment opportunities sit, how to track true ROI beyond engagement metrics, when vendor consolidation makes sense, and how reporting and compliance expectations are shifting for 2027.

It closes with a final diagnostic to help you separate warning signs from signals of strength across cost, member experience, clinical quality, reporting, and long-term readiness — so you can see where your strategy is strong and where it may need attention before the next plan year.
What’s inside:

10 questions to guide your 2027 benefits planning sessions
What a strong answer should include for each question
How to measure ROI beyond engagement metrics
A final diagnostic to pressure-test your strategy for hidden risk