Conversation Tips: How to Ask a Big Favor From a VIP
Asking a big favor from an important, busy person takes planning and rehearsal. Here are ten strategies to get a yes.
An early-morning thought made me fly out of bed. “My book coach was right. Jacquelyn Mitchard could endorse my book! She has 7 kids. As they grow up and go on dates, they could benefit from my questions and tips. Not that she’ll EVER allow them to date. At least not without a life jacket with a GPS on it. And a doodad that signals when the jacket gets wet. Perhaps a 911 call if the wet is 86 proof.”
[If you think I’m kidding, I am. Read her Q&A and you’ll see a vast sense of humor, even when it comes to her children. Especially then. When you finish this article, visit JackieMitchard.com.]
I rushed to the computer to learn more about her. YES! She’s perfect. She’s written 14 books, we both scuba dive, and best of all, I might see her today at the Maui Writers Conference. I’ve already escorted her to the bookstore and chatted about the knee she wrecked last year in a mud bath. (She called it “a vicious spa attack.”) We’re almost best buds!
Leaving My Common Sense at Home…
I drove to the conference. Spotting Jackie outside the Hibiscus Ballroom, I zoomed in. “I’ve written a book….”
If Jackie were a fencer, she would have cut that statement into 44 ribbons before it hit the floor. We’re in a WRITERS conference, for Pete’s sake. Even the walls have written books.
I forged ahead: “It’s called Do You Squeeze the Toothpaste in the Middle? Playful Questions for Dates and Mates. Would you consider endorsing it?”
She said, “I don’t think I’m the right person.”
Here’s where the director yells, CUT! Then she outlines the best way to make a big request. Her movie is called
10 Strategies to Get to Yes:
- Establish the right time to ask a big favor; and say how long it will take. The shorter, the better, but be realistic: don’t say it’ll only take a minute when it will take five because you will lose credibility. Say, “I have a favor to ask. It will take 2 minutes. Is this a good time to talk?” In my case, it wasn’t because Jackie was on her way to give the morning’s keynote presentation. I could have said, “Could we connect after your talk?” Find a time that works for both of you.
- Establish common ground if you can. Drop a name if it’s appropriate and honest.
- Acknowledge that you’re asking a big favor from a busy person.
- Use the WIIFM (What’s In It For Me?) approach. Give reasons why you’re asking this favor of this person. What’s in it for THEM?
- Make a specific and reasonable request. (A common request—“Could we get together sometime?”—is air-headed and meaningless.)
- Talk slowly. Pause at the periods. Let your information sink in.
- Listen, really listen, to the reply.
- Answer any objections. And stay cool while you do it.
- No matter what the answer is, say “Thank you” or “Thank you for your time.”
- Follow up.
My Ideal Pitch Would Have Sounded Like This:
“Jackie, could I have 2 minutes of your time?”
“Sure.”
“Thanks. Our friend Sam Horn suggested that you’d be a good one to endorse my book. It’s called Do You Squeeze the Toothpaste in the Middle? Playful Questions for Dates and Mates.
If you ever let your teenagers out of their cages and into the dating world, this book will help them sort the cream of the dating crop from the crud. It will boost their conversation IQ, even if they’re shy like you.
And you could use its questions to find out what’s going on inside those heads of theirs.
“I know you’re a busy, busy writer, and I think it’ll take only 10 minutes for you to get a feel for the book because it’s made of questions, tips, quotes, and anecdotes. Would you consider endorsing it?”
In my ideal world, she’d say, “I’d love to.”
Did I Get the Possibility of an Endorsement?
Did I eventually, excitedly, haphazardly and awkwardly provide enough information to overcome Jackie Mitchard’s objections and stumble my way to yes?
Jackie said, “Send it to me in January.”
Really. She did.


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