Do You Hate Asking People For Things?

Do you also hate asking people for things?
Below are tactics to make the asks easier!

Do you hate asking for help? I sure do. Which is odd because I'm generally happy to help others when I am able. It's less about the fear of rejection for me, and more about inconveniencing someone else. This summer, I've had to confront that weakening feeling directly.

In the summer of 2020, I started interviewing people who told stories in different ways. Orchestral Conductor, Editor, Actor, User Experience Expert, Ghost Writer, Photographer, and Author. I asked each about their approach to storytelling. We explored where they struggled, how they knew when a story was good and where they sought inspiration. These interviews were so fascinating.

It was important to me to include interview vignettes like this at the end of chapters. If you want to be a great storyteller, you have to consume different things to get insights and ideas. Which is the intent of these interviews. To share compelling stories and highly the different ways you experience stories in the world today. It is one of my favorite things about the book.

As I wrote the book, I wanted these interviews to be with a role or organization you recognize. My wish list was big. It had names like Levar Burton and Indra Nooyi on it. While I didn’t think they would say yes, having them on the list had me work through, “How do you make a compelling ask of a stranger?”  

I learned so much from the process that I wanted to share my insights.

Write your ask, then write it again

Right after I emailed my first request, I played this podcast episode during a walk. I wished I listened to it before I pressed send. Adam Grant walks through how to make an effective pitch. From describing the problem you are tackling to demonstrating your expertise. This episode is a masterclass in preparing an unsolicited pitch.

After I listened to the episode, I reworked my email. It turns out, it was too short. I was erring on the side of brevity. But I had omitted the things they needed to say yes: how my book is different and the role these interviews play. I also pulled my ask up to the top and made sure it was humble and not presumptuous. Plan for multiple versions of your request. Write it and challenge yourself to do a different version. The perfect one emerges through iteration.

Be specific

My friend Jeff Tetz gave me great advice: ask for 27 minutes. I was asking for 30 minutes, but that shift worked! 27 minutes is specific. Odd numbers are memorable. And it reinforces that I am going to honor their time.

Every person who said yes commented on it and asked, “Why 27-minutes?” It is mutually beneficial. Not only did it respect their time, but it was also the right duration for these interviews. You can learn a surprising amount in 27 minutes. If these were an hour, I’d have to edit out 75% of what they share. Specific requests stand out, especially when using odd numbers.

Do your homework

While I didn’t know who would say yes, I did draft questions for each. The questions often solidified the yes for those who responded.

When someone did say yes, I did my homework. I listened to any podcast episodes they were on. I read their books and articles. I checked out their online presence. Those 27-minutes were extended by doing the prework so we could start three questions deep and not with superficial ones.

I often get people reaching out to me. I’ve been disappointed when I do get on the phone with someone, and they haven’t prepared questions to ask and don’t know what they want. They sit there and expect me to ask all the questions and provide free real-time coaching. Most people are willing to help, but you have to do your homework and drive the process.

Make it easy for them

My goal is for the interview guests to have an easy, enjoyable experience. While each tells stories in different ways, most don’t normally get to talk about their storytelling approach. This was a fun and different conversation, and the 27 minutes flew by every time.

After the interviews, the guests get the transcript, the vignette to be included in the book, and a sign-off form. Their time is simplified into participating in the interview and reviewing the summary. Logistics can make or break an experience!

Constraint breeds creativity

My completed interview list includes storytelling in fields I hadn’t initially considered – like climate change, medicine, and video games. Hitting dead ends on my wish list brought me there. Those constraints forced creative thinking. A dead end becomes an opportunity when reframed with the exploration of “What next?”

You can’t win the lottery without buying a ticket

I’ve made over 40 requests. Many have ended up disappearing in the Bermuda Triangle of communications, never to be heard of again. Some people graciously declined. And so many cool people and organizations have said yes. When I made my wish list, it was easy to say “Oh, they will never say yes.” Many did. The only way to know is to try.

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Follow along with my process of publishing my book or catch up on previous book writing blog posts.