How to Ask without the awkward

Do you know what’s the worst? The moment right before you make an Ask — and also the moment right after a conversation doesn’t go as you expected. So today I’m sharing 3 of the most awkward moments for me as an auctioneer and what you can do about each, if they are awkward for you, too.


You have your script ready and a whole plan laid out. That’s great.

However, you also need to acknowledge what’s going on in the room.  How do you connect if there’s not any connection initially? You want to get connected really fast.

Use one simple observation or joke around a shared topic or celebration or even an embarrassment that can be light and fun to shine a spotlight on. The moment you do that, it snaps you into a more connected state. From that place of connection, awkwardness disappears.


When I step on stage for auctioneering, I’m frequently making a financial Ask of a room full of strangers who have no idea who I am. The solution is to borrow status. How I do this is by asking the executive director or a board member to introduce me, which lends me credibility from them. Then, I’m making my Asks from a stronger stance.

In your case, find a sponsor, mentor or somebody who understand who and what you’re looking for and can originate a potentially successful situation for you more easily. Your mentor can set up your Ask with an introduction so you can go into the Ask emboldened, without the awkwardness of a cold approach.


Having a plan can be a real lifesaver when things don’t go as desired. Not all fundraising goals are achieved.  Sometimes engagement and bidding is low. The room is just a bit cold. But I don’t let the icky feeling in the room define my experience. Even if we didn’t quite align, I’m still sharing my final words to close out the interaction. For concluding an evening of auctioneering, I may say:

“Thank you all for coming and letting me stand on this stage. I’m glad to help you give the way you did. You all did an amazing job. The bar is open.”

Mic drop. Exit stage.


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