Dig for the Story | 5 Followup Questions that Add Depth to Your Story

I hate small talk.

It’s superficial, trivial, and feels like a waste of time. Now, I know that’s not entirely true. Navigated properly, it’s a platform to forming a genuine connection with someone. And I’m certain I’d be more successful if I applied myself to mastering the art of small talk.

But I don’t because it feels awkward.

Whenever I engage in small talk, I risk being exposed. Because inevitably, I have to admit a shameful truth about myself: I don’t watch sports.

Let me throw myself under the bus real quick. I went to UNC Chapel Hill and maybe made it to the Dean Dome… twice?

I know. Shameful.

I’m not a sports fan pretty much for the same reason I hate small talk. And since most small talk is either weather or sports… I feel like I’m playing Russian Roulette with strangers.

Stranger: You see them game last night?
Me: Ah, no. I’m not much of a sports guy.
Stranger:
Me:
Stranger: Ok…

See? Awkward and exposed.

I’m more of a movie person. I love stories. I like ideas, deep ideas, and learning new things. I guess I hate small talk because if I’m going to invest in a conversation, I want it to be worthwhile. Too many conversations, and relationships for that matter, stay in that superficial plane… and I can’t stand that.

You can basically categorize meaning into three different layers.

  1. Superficial - Trivial, fluff, insignificant and unimportant details. Basic causal relationships and situational dramas.

  2. Significant - Underlying meaning and reasoning behind to situations or disciplines. Digging into relationships, motivations, and inner workings of systems.

  3. Fundamental - Deep questions of being, identity, the nature of reality, etc.

I can’t stay at the superficial level. I have a very strong drive to dig deeper and find meaning and connection. I guess you could call that curiosity.

And I dig by asking questions. Specifically followup questions.

The followup question is the storyteller’s tool. It’s your shovel. With it, you’re able to mine for wonderful, authentic stories full of meaning, depth, and character.

For example, your initial question will always give you a topical introduction, it’ll scratch the surface, but rarely will the answer provide you with the substance necessary for deep understanding. Simply because understanding takes time, and time is limited. So we always start broad and then work our way down into details and meaning.

Our job is to dig deeper. Guide our subject from superficial, to significant, and (if we’re lucky) fundamental.

These might come off as pretty obvious, but to help you dig beneath the surface and draw out your story, here are five ways I phrase my followup questions:

  • Help me understand…

  • Explain that to me.

  • What do you mean by that?

  • Can you go into that a bit more? / Can you elaborate on that?

  • Why is that important?


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“Why Is that Important?” | My Go-To Question for Customer Testimonials