Interview Fundamentals: 3 Perfect Questions

Years ago, when I first started interviewing folks for alumni magazines, I could not have been more terrible at asking questions. Once, while interviewing a recent grad whose short stories had been widely praised, I asked the following “question.”

“I read that your work has been compared to Italo Calvino’s. That must be pretty cool.”

Her response? “Uhhhh, yes. That was nice.”

GREAT JOB, PETERSON. Prepare for that quote to go viral.

Good interviews lead to great stories.

A good interview can help elicit incredible anecdotes, unique insights, and unexpected details. Bad questions often lead sources to share vague, unhelpful quotes and empty platitudes.

It’s true that there is no one-size-fits all list of interview questions that you can have for every source. But over the years, I’ve found that there are a few questions and approaches that have led to better interviews, better quotes, and better stories.

Here are three of my go-to questions.

1: How did you end up at [school]?

What makes this a great question? 

I’m not going to pretend that you don’t already ask this question of most of your alumni sources — you probably do! It’s not rocket science.

But I often make this the first question I ask after confirming the spelling of their name and title. You can, too.

I like this question because it eases people into the interview. It’s something people don’t have to “prepare” to answer. Many people have a surprising story behind their decision to attend a school, or will offer up information that is helpful later — perhaps they are the first person in their family to attend college, or they picked the school because of its chemistry program, but ended up majoring in English.

It’s also a good question because it immediately helps you understand how they’ll likely be answering the next questions.

Are they giving a curt reply, meaning you’ll probably need to ask lots of follow-up questions during your interview? Are they giving a 15-minute monologue, meaning you’ll probably have to pick just a few important questions to focus on?

Getting clues from the outset on a question like this can help you make some on-the-fly decisions that help you get great responses later on.


2. Can you paint me a picture of…

What makes this a great question?

Sometimes, people I’m interviewing speak to me as though I am an expert in their field.

For example, a scientist might tell me that they’re synthesizing molecules in their lab. Unfortunately, that means almost nothing to me.

When sources tell me about what they’re doing in a way that feels abstract, I dig in by using a variation of “Can you paint me a picture of…”

Can they paint me a picture of their lab? Paint me a picture of the process? Paint me a picture of the moment that they understand that they’ve found something meaningful?

I’ll even come up with some examples, both so they understand the level of detail that I’m looking for and so they understand my level of ignorance and tailor their responses appropriately: “Can you paint me a picture of what you mean when you say ‘synthesize a molecule?’ Are you looking through a microscope? Are you putting something in a petri dish?”

The details that come from that questions are almost always illuminating and worthwhile.

Yes, it sometimes makes me look really dumb. But I’d much rather look dumb in an interview than end up putting something in print that is vague, boring, or incorrect.

Versions of this question are very common in radio and podcast interviews — do a search for “paint a picture” and you’ll find it in all sorts of Q&A radio interviews and podcasts. Here’s one, for example, in an episode of Without Fail with Alex Blumberg and another in a modified Q&A on Reply All.

Start listening and you’ll hear it everywhere, I promise.

3. What are you optimistic about?

What makes this a great question?

Over the coming months, a lot of us will be talking to our alumni and administrators about tough issues, including COVID-19, economic challenges, and social unrest.

In my own reporting, I hear quite a bit of pessimism. But if there’s one thing I know about alumni magazines, it’s that it’s rare for stories to end on a note of cynicism or hopelessness. The whole point of education is to help people improve their lives and the world!

Asking people what makes them feel optimistic about the topic they’re being interviewed about can help change the frame.

One infectious disease researcher I spoke with shared with me his many concerns about the federal response to the pandemic, nursing home outbreaks, and testing gaps. I asked him if there was anything we could feel optimistic about during this moment.

He had to really think about it. But he came up with a response I ultimately used as the story’s kicker: “The whole world is focused on this problem,” he told me.

It’s true! And honestly, it made me feel better.