The Wingdale Harbors Newsletter

A monthly letter from D.A. Abrams on leadership, growth, and building organizations that last.

This Month's Theme: The Art of Inquiry

Dear Reader,

This month I want to talk about something deceptively simple: asking questions. Not the rhetorical kind that leaders use to steer conversations toward predetermined conclusions. Real questions. The kind that open space for thinking, surface hidden assumptions, and occasionally change the direction of an entire team.

I have spent three decades observing leaders in boardrooms, strategy sessions, and one-on-one conversations. The pattern is clear: the leaders who ask the best questions consistently produce the best outcomes. Not because they are smarter, but because they engage the intelligence of everyone around them.

It is a skill. And like every skill, it can be learned.

From the Blog

This month's featured articles explore the themes of curiosity, resilience, and strategic execution:

• The Power of Asking Better Questions — Five questions that transform meetings, and the discipline of silence that makes them work.
• Building Resilient Teams That Recover from Setbacks — Resilience is a team skill, not just a personal trait. Here is how to build it before you need it.
• Why Most Strategic Plans Fail Before Execution — The five reasons plans die in the hallways, and the execution architecture that prevents it.

A Question Worth Sitting With

One of my favorite practices is ending each week with a single question. Not a question that has an easy answer, but one that creates useful reflection. This month, I have been sitting with this one:

"What conversation am I avoiding, and what is the cost of avoiding it?"

In my experience, the conversations we avoid are almost always the ones that matter most. The feedback we are not giving, the strategic question we are not asking, the relationship we are not repairing. The cost of avoidance compounds silently, and by the time it becomes visible, the repair is far more difficult than the original conversation would have been.

If you identify one such conversation this month and have it, you will be ahead of most leaders.

Lessons from the Field

I recently worked with an association board that was struggling with engagement. Attendance was declining, committee work was stalling, and the executive team was frustrated. When I asked the board chair what she thought was happening, she had a detailed theory about generational shifts and competing priorities.

When I asked the board members directly—"What would make this board experience more valuable to you?"—the answers were different. They wanted less reporting and more strategic conversation. They wanted to feel like their expertise was being used, not just their attendance recorded.

The solution was not complicated. The board restructured its meetings to dedicate 60% of the time to strategic and generative discussion, moved routine items to a consent agenda, and created small working groups around emerging issues. Within two quarters, attendance improved and the quality of board conversation transformed.

The lesson: the right question, asked of the right people, often reveals solutions that were hiding in plain sight.

What I'm Reading

This month I have been revisiting sections of Association Management Excellence on board governance. If you are involved in nonprofit or association leadership, the chapters on generative governance and meeting design are particularly relevant to the themes in this newsletter. Browse the full collection on Amazon.

Coming Up

Next month, we will explore the topic of navigating uncertainty—how the best leaders make decisions when the data is incomplete and the stakes are high. We will also share new content on emotional intelligence and its practical applications for executives.

In the meantime, if you or your organization could benefit from structured leadership development, explore our online courses or inquire about custom corporate training programs.

Until next month,
D.A. Abrams