Asking Shouldn’t Make You CringePosted on November 17, 2014 by Alia McKee Here’s how an Executive Director went from magic to misstep in 10 seconds flat. Last week, I spent a full day in community with the membership of my meditation center — my spiritual home — and met the leader and teacher Sakyong Mipham Rinpoche, a rare treat. It was transformational. After the event, the Executive Director of the center stood up in from of 250 people and very apologetically said, “This is when we have to make an ask. It’s going to be painful. But we need you to stretch.” Wow! Talk about whiplash. It took a beautiful moment to awkward very quickly. The day after the retreat, I had the privilege of speaking alongside the inspiring Karen Osborne who specializes in training ED’s and board members in the art of the ask. She had some great insights: – Fundraising should be joyful. Yes, we are solving urgent problems. Yes, we are needed. But fundraising is not painful. It’s a way we can channel our donor and prospects passions into building a better world. – Lead with stories about the people you are helping. Everybody making an ask should understand the cause. They should know the emblematic stories and be able to tell those stories. – Don’t offer donors a shopping list of giving and naming opportunities. Share the societal problems you are solving, the lives and conditions you are saving and changing. Lead with mission and vision. Who cares about your campaign goals? It’s about your ultimate goal. I sure wish the ED I heard had talked with Karen before her pitch. Who in your organization could learn this lesson? Send them to Karen’s blog. Here she is.