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Hot Seat Coaching Session: The Power of Alignment

The Power of Alignment: Leading Your Board Through High-Stakes Decisions

Leading your board through a major decision—whether it’s a strategic pivot, leadership change, or new investment—can feel like walking a tightrope. You need alignment without pressure, urgency without panic, and inspiration without losing sight of the facts.

In this Hot Seat Coaching session, Harold Wolpert, Founder & CEO of My Purple Crayon will share practical strategies for helping your board navigate complexity with clarity, confidence, and care. With real-world insights this session will give you a framework for helping your board make thoughtful, aligned, and timely decisions. We'll unpack how to:

  • Identify the problem to be solved: uncover the real factors driving the decision and the obstacles to progress.

  • Educate and inspire: determine what your board needs to know—and how to keep enthusiasm and purpose alive through uncertainty.

  • Achieve alignment: get everyone moving in the same direction (even when opinions differ).

  • Apply “constant, gentle pressure”: use Danny Meyer’s famous principle to guide steady, values-driven momentum toward resolution.

    This interactive session is your chance to bring real-world challenges to the table. If your board feels uncertain about the next step, weighing a big decision, or simply afraid to act, you’ll leave with tools to lead them forward—confidently and collaboratively.

    #nonprofits #nonprofitleadership #boards #fundraisingstrategy #HotSeatCoaching

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October 31

Hot Seat Coaching Session: Fundraising Without Fear