Cultivate Great Stories

Interviewing Tips for Nonprofit Writers

Don’t go into an interview thinking you already know the story—odds are you only know a piece of it. Let your speaker share their expertise, and learn from it. It’s GREAT to be surprised during an interview, because it means your readers will likely be surprised too.

Create a list of 10-20 questions in order by theme, but don’t force yourself to stick to the list and don’t ask the questions in strict order—you’ll need to constantly re-shape your questions based on the responses from your subject. I check my list every few minutes and cross off questions or highlight those I haven’t yet asked so I don’t miss any big items.

If your interview prep is boring you, you’re not doing enough work. Nonprofits tackle fascinating problems, so if you find the topic dull, odds are you’re not digging deeply. If you somehow get to the interview and still find your interest wavering, ask the subject why it’s so important. Find out why they’ve devoted years to the topic. Admit your own ignorance on the topic, and ask them to help you “get it.” Odds are the subject will be happy to do so.

Don’t worry that you’re taking up too much time or asking too many questions. Most people love to talk about themselves. Just think: In your day-to-day life, how often is someone completely focused on every word you say, just dying to learn more, to share your story with hundreds or thousands of people? You’re putting the subject on a stage—odds are they’re excited about it.

Keep asking “Why?” Yes, be an annoying little 5-year-old. After two or three or four why’s you’ll almost certainly unearth a fascinating nugget.

Tell the subject what you find fascinating, surprising, or perplexing about the subject. Interviewing isn’t an interrogation—it’s a conversation. By sharing your point of view and showing your excitement, you’ll rekindle their excitement.

Isolate pieces of the challenge. Ask if there was ONE key moment where this problem exploded. Or one mistake that let it get out of hand. Or one person who had an outsized impact on the challenge. Or one promising opportunity that could turn things around. Life isn’t always that simple, but sometimes it is.

Don’t be afraid to look dumb. Some writers think “I need my interview subject to see that I’m smart, so I’m going to do hours of research, ask tough questions, and never admit there’s something I don’t know.” Big mistake. Conduct enough research to get a solid grasp of the topic, but remember, you need an expert to explain things in simple terms; you can’t possibly match your expert’s knowledge on the topic. Accept it, and you’ll get great quotes.

When you’re confused, tell the subject you’re confused. If you don’t understand something your subject just said, you can’t use any of it, and your next 2-3 questions will be the wrong questions. Stop, and get them to explain it again. You represent the reader—put your ego aside and fight for their knowledge. (See “Don’t be afraid to look dumb.”) And odds are it’s not your fault—the speaker probably just didn’t do a good job of explaining the issue in simple terms.

Use the old “Some people argue…” or “What do you say to people who insist…” to set up a hypothetical argument with your speaker. Even if it seems practically impossible to disagree with their viewpoint, this question forces them to spell out their thinking in concrete terms that tend to generate good quotes.

Bring up recent news about the subject or popular knowledge around the topic ala “I just read an article that said X…” or “Most of us learn Y in high school….” The subject will probably respond, “Yes, that’s a great example” or “Actually, that’s a common myth.” Either way, the next quote is likely to be good.

Notice when your subject gets particularly animated—whether they’re happy or angry, it’s an indication of a topic they want to discuss more. Stray from your list and follow them down that path—it almost always leads somewhere interesting.

If your subject is going on a tangent, give them a little slack, but reel them in if they’re going too far afield. You only have so much time, and there are things you need to accomplish. Sometimes a good tangent leads down a fascinating path, but if you sense it’s going nowhere, find a gentle way to rein your subject back in.

Be OK with silence. Let the speaker fill it. This is a tough one. In most conversations, silence is awkward, but if you’re asking good questions, your subject will need time to think, to generate a good answer. Even when they seem to be done talking, try to pause for 2-3 seconds before replying, because there’s a good chance they’ll say more.

Focus less on facts and more on the colorful stuff. Good articles contain a mix of facts, stories, emotions, and opinions. In most cases, the writer captures the facts and lays them out clearly, then the subjects’ quotes provide anecdotes, emotions and opinion. To use a TV sports analogy, the writer is the play-by-play announcer (“She dribbles by the defender and takes a shot!”) and the subjects are the color commentators (“That was an incredible shot—the keeper had no chance of stopping it.”) You’ll get plenty of facts from your subject (and you may write many of them in your own words), but the best quotes are typically the color commentary.

Repeat a portion of the subject’s answer back to them. It’ll often spur their next thought.

Record every interview. Some people scribble notes and try to recapture what the subject said. In my experience it’s impossible to write it all down AND think of your next question. Record it and you can relax, knowing you can always refer back to it.

Recognize that unless you’re writing a straight Q&A, you’ll probably only use 3-5% of the words that come out of the subject’s mouth—that’s the way it should be. Automatic transcription software typically captures 80% of the words spoken—you can fill in any gaps by going back to your recording, but don’t worry about getting a perfect transcript because few of the words will end up in the final piece.

Make sure every quote represents 100% of the subject’s idea/tone/point of view. People don’t speak as clearly as we all write, so it’s OK to delete a few words here and there, put a LITTLE polish on an awkward phrase, and move clauses and sentences that appear out of order. My hope is that when the subject reads the piece, they’ll say “Yeah, I definitely said that,” when they see the final version or review it in advance.

Close the conversation with “Is there anything I didn’t ask you but should have?” Again, have the humility to know what you don’t know. There’s a good chance the subject is passionate about something you didn’t know enough to ask. Often that one simple question leads to 2-3 follow-ups that generate great stories and quotes.

As you’re reviewing the transcript, you might use one color to highlight the best quotes from your subject(s), and use another color to highlight the key points you’ll make in your own words. I typically build my stories around those items, with the quotes as the “bricks” and the remaining details as the “mortar.”

Don’t be afraid to go back to your subject with 1-2 questions via email, or even hop on the phone for another quick call. When you listen to the recording of an interview, you’ll often discover a quote that needs a little more context, or a question you failed to ask. You don’t want your readers to walk away with unanswered questions too.