Leadership Insights

Design for Pain Points, Not Assumptions 

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Tactical steps for the 2026 academic year.

Many leadership programs fail because they’re built around assumptions of what leadership should look like, rather than what specific leaders actually need.

When we surveyed higher education professionals about the qualities they most value in a leader, three rose to the top: effective communication, building trust, and vision and strategic thinking. These aren’t abstract ideals; they’re the skills people are watching for in their day-to-day experience of being led. A program that doesn’t address them is solving the wrong problem.

A few ways to uncover what your leaders actually need before you design anything:

Start with diagnostic listening: Conduct brief interviews or surveys asking leaders to name their top two or three current challenges, what’s keeping them up at night, and where they feel least confident. Look for patterns across responses. Those patterns will become your program modules.

Build around skill gaps, not just knowledge gaps: Once you’ve identified common pain points, design learning that lets leaders practice in low-stakes environments. Role-plays, case studies drawn from your own institution, and peer coaching tend to land better than lecture-style content because they require leaders to actually do something with the skill.

Create ongoing support structures: Pain points don’t resolve after a single workshop. Peer learning groups, monthly check-ins, and mentoring partnerships help leaders to keep working through challenges over time and allow you to adjust the program as new issues emerge.

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