29 November 2023 |

Two tips for mastering the art of interviewing

By Tracey Wallace

Interviewing is an art, and it takes time and practice to get good at it. I could honestly end this week’s newsletter here by saying, “Just do it more often,” and overtime, you’d develop those skills naturally. 

That said, I’ve gotten two main tips in my career around interviewing that I think can be helpful. So, let’s dive on in!

Follow the pain: 

This is the best piece of interviewing advice I’ve ever gotten. Part of your job as the interviewer is to pick up on subtle cues from your interviewee about where something was harder than expected, more challenging than expected, annoying, etc. All of these cues lead to more pain, and pain makes for an interesting story, even when you’re writing about B2B. 

A lot of folks will hide the pain behind a joke or a laugh, and that’s always a telltale sign. But you can also tease it out of them: “Oh, that sounds like it was hard. How did you handle that?” 

Anything can cause pain for folks, but you’re mainly looking for the root causes of all human pain and suffering in these interviews, because that’s what makes people relatable. Often the root pain is:

Stress that causes lack of sleep, distraction at home, over-working, over-thinking, over or under eating, and basically disrupts the normal and natural patterns of our lives. 

I’ve written great stories about stress based on RFP processes (can you imagine?!), starting a business (my favorite got started as two new parents tried to care for triplets that had gut issues, and led them to the rabbit hole of Google at 4 a.m. looking for some kind of future sleep relief), and the fear of losing your job (which is honestly one of the main stressors and thus motivators for non-entrepreneurs). 

Get curious here and listen intently. Set yourself up for success so you can listen intently rather than taking notes.

  • Always record the call––but ask them if they are comfortable with that before you hit that record button. It’s a courtesy. 
  • Drop the recording into a tool like Rev.com afterward to transcribe it. This will make your life easier, and pulling in quotes from them easier, too. 

Make them the hero of the story:

When you follow the pain, you are most likely trying to set up a “Hero’s Journey” or “Stranger in a Strange Land” storyline. These are two of the most popular storylines in the world. Heck, Disney uses them almost exclusively.

For the Hero’s Journey, the main one you’ll likely tell, the setup, simply, goes like this:

  • The departure. The hero leaves the familiar world behind.
  • The initiation. The hero learns to navigate the unfamiliar world.
  • The return. The hero returns to the familiar world.

Your goal in the interview is to figure out the peaks of each of these phases, and make your interviewee the heroes within them. 

So, you start:

  • Asking questions about the before:
    • What were they doing / how were things before?
    • What was hard about that before? What was easy?
    • What caused the change—a need by the company to solve for some kind of pain or an external force like covid or economic uncertainty? 
  • Asking about the initiation: 
    • What was that change like? 
    • All change has a slog of time and confusion that comes with it––what was that like? How long did it take? How did the person deal with it? 
  • Asking about the return: 
    • What is the world like now? How is it better, and how did this person contribute to making it such? << This is where you really get into their heroness. 
    • How is this new world more resilient than the last? Why is it better? 
    • What did they learn through his process? What advice would they give others going through something similar? What would or wouldn’t they do again, with hindsight?  
    • What’s next? Is there another change on the horizon? (there always is!)

Finally, make an emotional tieback from this storyline to their life in general. Here is how I set it up, 

“Thank you so much for all of this, and getting so deep on how this all came together. I only have one last question, and its pure curiosity at this point. This was a lot. And you handled it so well. On a personal level, I’m just wondering, why? Why do this? Why get out of bed in the morning and work on this set of problems? What inspires you about it? What do you learn from it? Why this?” 

On that question, I have had at least two people cry in my career of interviewing, and only one person not soften up (there’s always the one). 

Most people take this question to heart because it 1) Shows you were listening to the story and 2) Gives them a question they probably haven’t even asked themselves. Every single one of us does what we do for a reason. We are creatures of motivation, and understanding the motivation of our characters is crucial. 

You might not use what they answer to this question specifically, but you can weave it through the entire piece because it gives you a sense of why––why they started, why they ended up here, why they approached it the way they did, why they are who they are. 

And it is that humanness that connects us all that interviewing is ultimately after—to tell a great story, yes, but to tell a story only a human could tell.