The Leadership Questions That Matter

Posted on July 30, 2026 by Sharon Hollister

Most leaders don’t struggle because they lack answers, but because they rarely have time to ask the questions that matter.

The pace of leadership today can leave little room for reflection. Staffing concerns, operational priorities, budgets, compliance, and unexpected challenges demand immediate attention. Before long, an entire month—or year—can pass without stepping back to consider the larger questions that shape an organization’s future. Questions like:

• Where are we trying to go?
• What do our employees need from us now?
• How are consumer expectations changing?
• What kind of culture are we creating?
• How do we lead through uncertainty without losing sight of our mission?

None of these questions have quick or easy answers. They require time, perspective, and conversation.

That’s one of the reasons LeadingAge Minnesota has gathered leaders together at the Annual Meeting & Leadership Forum for generations.

Strategical & Practical

This year’s program is designed around the strategic issues leaders are navigating today — from workforce and artificial intelligence to payment reform, consumer trends, and organizational growth. Along the way, nationally recognized speakers and experienced Minnesota leaders will offer practical ideas, new perspectives, and opportunities to learn from one another.

Keynote speaker Amanda Brinkman will challenge attendees to think about the connection between purpose, leadership, and lasting impact. Her message complements the broader goal of Annual Meeting: creating space for leaders to think beyond today's challenges and prepare for tomorrow's opportunities.

The conversations you have at Annual Meeting won't solve every problem you face. But they may help you ask better questions. And for leaders, that's often where meaningful change begins.

Annual Meeting is Sept. 15-18 at Grand View Lodge in Nisswa, MN. Early bird registration is available through August 14. Click here to view the conference brochure, explore the agenda, apply for a scholarship, reserve lodging, and sign up for the golf tournament today.

Questions? Education@LeadingAgeMN.org