Leadership Insights

Design for Pain Points, Not Assumptions 

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Leadership Insights

 

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.

Strategic Scaling 

This week, we’ve established that the demand is real: Nearly 85% of respondents to our survey expressed at least moderate interest in more professional and leadership development. So once a program is under way, how do you scale it to meet that demand? 

The most useful question to start with is: What do your department chairs, Deans, directors, and VPs need to know, and when do they need to know it? That clarity helps you to decide which elements require intensive facilitation and which can be delivered through more scalable formats. 

Three approaches that tend to work well: 

Create a tiered delivery model: Develop foundational content that can be delivered through online modules, peer learning circles, and intensive workshops. This lets you serve more participants while reserving high-touch facilitation for advanced levels. 

Build internal capacity: Train a cohort of internal facilitators from your program graduates. They know your institutional culture and can extend your reach while maintaining the quality and consistency of what you’ve built. 

Establish clear learning pathways: Design modular programming where participants can enter at different points based on their experience and development needs. This prevents bottlenecks and allows for continuous enrollment rather than a single annual cohort. 

Scaling isn’t only about adding participants. It’s also about making sure that every leader, regardless of role or schedule, has a clear way in. The institutions that do this well are the ones that treat leadership development not as a program they run, but as a culture they build. 

Pause & Reflect 

Where is your institution on this continuum right now: absent, emerging, established, or scaling? What’s one concrete step you could take in the next 30 days to move it forward? If you need a brainstorming partner, consider using Sophia, our AI leadership coach

Share what you’re thinking with us on LinkedIn using #DailyLeadershipPractice.