December 10, 2020 / Esther Choy


Asking for stories

Furious typing. That was usually what greeted my friend, Heather, each morning when she walked into the office she shared with her boss. Heather would head to her desk and see her boss hunched over her keyboard, elbows out, clattering away. Then her boss would hit the final key like she was striking the last note of a piano concerto, whirl her chair around, and lean back.

“Now,” she would say, signaling that the concerto was over and it was time to gather thoughts and take stock of the day’s tasks.

And often, it was time to tell stories. Her boss found other people fascinating and funny and could recall past events in detail. So she used this early morning time to share a story or two.

My friend often thought of these stories as a break before the real work began, but she suspects that her boss thought of it as the glue that held the day together. And looking back on her time working for this boss, she realized that the stories inoculated her against institutional amnesia—they provided context she wouldn’t have had otherwise.

If Heather was headed over to talk with Marjorie at HR, for instance, she now knew that Marjorie had adopted five kids and coached her oldest daughter’s soccer team after work. Now Heather could scurry over to HR, tedious forms in hand, knowing the human behind the transaction.

Heather started to love having her days enriched by stories. But what if you work for someone who does not make a habit of telling stories? What if, for instance, you want to find out the human side of a project you’re about to take on? Or what if you’re headed to a networking event and want to make meaningful connections? Or, in a more formal setting, what if you want to capture the stories of your team, your clients, or stories to share in presentations? Maybe in that case, you’re interviewing someone you don’t even know yet.

Asking for stories might involve different practices based on whether the setting is casual or formal. There’s an art to story-gathering in each setting. Leadership Story Lab can facilitate story-gathering among your team, provide one-on-one guidance as you practice your own story, and teach you to be a story facilitator. Here are some of the insights we’ve found in ten years of business storytelling.

In a Casual Business Setting

1. Don’t shut down the conversation before it starts. Keep the questions open-ended.

Questions for your manager might be:

  • “Can you tell me about a time when you’ve worked with this department in the past?”
  • “Can you describe the key players?”
  • “How have we solved a similar problem before?”
  • “Where do we tend to get stuck?”

Questions for a networking event might be:

  • “What made you choose your occupation/cause/hobby?”
  • “What do you like to do when you’re not working?”

2. Fire up the follow-ups.

With follow-up questions, the goal is not just to get them to keep talking, but to refine your understanding of the story. Try questions like, “When was this?” “How did we get to that point?” Or even, “tell me more about that.”

3. Demonstrate your interest.

“They’ve got to believe you’re interested,” story-capturing maven Studs Terkel once said. How do you convey interest?

In our distracted age, speech coach Nick Morgan says “we have an epidemic of fake listening.” But when people know you really are listening, it makes them feel respected, especially since real listening is so unusual!

4. Sprinkle in the delicate questions.

If you have to ask delicate questions, don’t ask them all at once, advises David H. Mould in the oral history handbook Catching Stories. Spread them out among easy questions. Maybe you have to question a prior decision, or ask what happened to Carl from Sales… but be sure to get the information you need without stacking sensitive question upon question, which can come across as aggressive.

5. Recognize that the teller is vulnerable.

Taking time to tell stories can make the teller feel vulnerable, first of all, because setting this time aside bucks workplace norms. We tend to disparage “water cooler conversation” and think of workdays as the sum of the things we got done. We hardly take time to consider what aspects of our workday made us feel like human beings, or how the things we did actually got done better because of the sociable interactions.

And beyond that, a story—even a business story—is personal. The story may involve making a tough call or weave in facts about other people—facts the storyteller might not feel at liberty to share. Stories are not cut and dry, and part of the vulnerability of telling a story comes from fear of saying more than we intend, leaving things open to interpretation.

Lastly, when it’s a boss telling a story, they might worry that telling stories makes them seem weak. (But see my post on the power of compassionate leadership!)

Don’t let any of this stop you from asking for stories, but do realize what you are asking, and show respect and give encouragement.

In a Formal Story-Gathering Session

In a more formal setting—where you are doing some intentional story gathering—all of the same rules apply. But there are further considerations when you are asking a client or colleague to tell you a story you plan to share publicly.

1. Share the “why.” Tell the storyteller why you want to hear their story. No one is going to open up if they don’t know where their words will end up! And if the teller is busy, they may not want to make time unless they’re sure you have a clear purpose and that purpose fits their own priorities. So be honest about your goals.

2. Realize it’s a two-way street. The teller is going to get something out of the process, too: a chance to help others, a chance to promote a cause they believe in, a chance to champion their team’s accomplishment. Be aware that sometimes the teller’s agenda will conflict with yours—and prepare some conversational tools to redirect them to the session’s goals (my favorite from this list of tools is “I’d love to hear more, but I also want to know about…”).

3. Iron out the logistics.

  • If you’re recording the story, check that all associated technology will cooperate. Do a test recording before your interview. Check the recording device’s storage capacity and make sure it’s been charged.
  • Silence your phone.
  • Consider the time of day. What is the most distraction-free time for your storyteller?
  • Locate a quiet place to capture the story.

4. Don’t script it. Nope, formal doesn’t have to mean scripted! In Catching Stories, Mould suggests writing down topics or themes rather than carefully worded questions. Differentiate between what you must ask and what you would like to ask.

5. Let them choose the ending. End by asking the storyteller if they would like to tell you anything else. Sometimes, says Mould, they’ve had a great story all along, but the questions have not naturally led to it. Or sometimes I will find that, at the end of the session, someone wants to underscore what they think is most important about what they’ve told me. I might agree, or I might find it fruitful to explore why they think it is key.

6. Keep it short. Gathering someone’s story requires more focused listening than we’re used to, says Mould. It’s exhausting! And it’s exhausting for the storyteller, too, to consider apt responses to your questions and relive past events. Mould recommends keeping sessions under an hour and a half.

Your attention to the teller’s story will create a supportive environment. That will be good for you—mining the stories you need for your next presentation, making a valuable connection at a networking event, deepening your rapport with your boss, and helping you see the nuances behind your work assignments. And it will also be good for the teller, who will have practiced this valuable persuasive skill in a safe space.

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Esther Choy

Esther Choy founded Leadership Story Lab in 2010 to help others leverage the art of storytelling to create extraordinary opportunities.
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