Day 1: Why You Should Ask Strong Questions (and How to Do It)

Howdy friends, and welcome to our series on how to become a better listener!

If you missed the introduction post yesterday, I’d recommend going back and reading it real quick. It lays the foundation for this whole thing, and it has two important mindsets that you’ll want to keep in mind throughout this entire process.

All caught up? Good. Let’s dive right into day one, which contains my single favorite tip for becoming a stronger listener. Quite simply, it’s this: if you want more useful information to listen to, you’ve got to ask strong questions.

The reasoning here is pretty simple. At the core of every great story is a compelling character (or several), and strong questions are one of the most powerful tools we have for evaluating the strength of the potential characters in our story.

In the language of Muse (the step-by-step process we use for telling stories), there are three super important qualities that a character must have in order to be strong enough to carry a story. We call them the Big 3 Things, and they are:

  1. Uniqueness - What makes this character different?
  2. Complexity - Why does your character do what they do?
  3. Desire - What does the character want more than anything else?

When we’re diving into the process of telling a story, we’re listening for anything and everything that might help shape the story. But in regards to people, we’re listening specifically for information that gets us closer to the Big 3 Things.

If a character has them, they’ll be compelling to carry the story from start to finish. If they don’t, they might still be good as a supporting character, or maybe they’re just not the right fit for this particular story. Either way, you won’t really know until ask the right questions.

So now let’s dive into a few of our favorite tips and tricks for designing strong questions for your initial conversations, pre-interviews, and recorded interviews.

Do your homework

This should go without saying, but before going into an interview or pre-interview, you should have already uncovered plenty of information about your subject. As my third grade teacher always said, “You’ve gotta do your homework and come to class prepared. No excuses.”

Spending some extra time up front doing research benefits the interview process in a couple of ways.

First, it puts you in a position where you can focus more time and energy on strong questions. When you know the basics, your questions will become more informed.

All of your research should provide the context you need to dig deep and move beyond surface level questions.

Second, it’s a sign of respect and courtesy towards the interviewee when you’re well-prepared. Not only does it make them feel valued, but it shows that you’re serious about your craft and about making the final product as good as it can be. It shows that you value their time and yours.

I’ll talk more about why that’s important in tomorrow’s article. But for now, suffice it to say that being well prepared helps create an atmosphere for the interview that’s conducive to getting the answers you need.

As for how you actually conduct research, it really varies from project to project. Depending on the size and scope of your film, this research phase might take anywhere from a couple of hours to a couple of weeks.

It might involve diving into a rabbit hole of google searches and social media. It might mean talking to additional people. It might mean immersing yourself in the world of your character completely for a couple of weeks. It really depends on the depth and scope of the story you’re telling.

Regardless of how involved your research process is, though, it usually starts on the internet. Almost everyone has an online identity these days. Make sure you find it and study it and use that information to inform your interview process.

Beyond that, use your best judgement. Some stories require more hands-on research and more immersion. Others, not so much.

Designing Questions to uncover the Big 3 Things

There are many schools of thought on how to ask strong questions (seriously, just google it), and most of them are perfectly valid.

However, during documentary work, I like to use a simple two-pronged approach for coming up with interview questions. It’s an approach that allows for spontaneity, and it’s really helpful for uncovering new pieces of the story, which is the whole point of this series.

I’ll explain it in a bit more detail later, but here’s a quick rundown of how the approach works:

I start with an open-ended question that allows the interviewee to dive into an explanation/exploration of some facet of the story. After that, I like to follow up with a question designed to shed light on their purpose, and to uncover how they think and feel.

This approach is helpful for a couple of reasons. First of all, it helps you avoid asking too many leading questions (which come from assumptions you’ve made or answers you want to receive). If you value real, spontaneous answers, leading questions will almost never get you the results you want.

Second, the open-ended nature of the questions often leads to new information and pieces of the story that you wouldn’t have found otherwise. Targeted, specific questions often lead to targeted, specific answers. This isn’t always a bad thing, but when you’re trying to listen for new pieces of the story, you want to make room for spontaneity and delightful surprises.

Lastly, the open-ended questions allow for a more relaxed, conversational interview (more about that tomorrow).

My two-pronged approach to interview questions

Alright, so let’s get into a bit more detail about this process for asking questions.

First up, you ask your interviewee to walk you through something related to the story. You should have done plenty of research, so ask them to tell you about a relevant event, person, company, idea, etc, and then just let them talk. Push further and ask more when you have to, but this is really about giving them free space to say whatever they want.

Here are some examples of how you might start a question like this:

  • Tell me about a time when…
  • Walk me through the conversation you had with…
  • Do you remember much about…

More than anything, these are lines of inquiry rather than direct questions meant to elicit a specific answer. Their purpose is to shed light on interesting details and to uncover things that might not come out with more traditional, direct questions.

It’s through these open-ended questions that you’ll come upon pieces of the story and interesting ideas that probably wouldn’t have surfaced otherwise.

And now for the second prong in this approach. When something strikes you as really interesting and worth digging into deeper — especially if you feel like it might shed light on someone’s Big 3 Things — don’t hesitate to ask followup questions like:

  • Why is that important to you?
  • How did you feel about that?
  • What were you thinking about as you did that?

I know this may sound a little bit like a cliché therapy session, but trust me, it works. This is a great way to get to the good stuff.

These simple followup questions should help you get a very clear sense of someone's uniqueness, complexity, and desire. In the grand scheme of things, “why” is one of the most powerful, revealing questions you can ask. And digging into motivations and thought patterns and feelings is also a great way to really probe into the complexity of a character.

Even dumb questions can be valuable

There’s one other major point that I want to touch on before we wrap up today. Don’t be afraid to ask dumb questions

As the storyteller, it’s your job to make sense of all the information you’re given and present it to the audience in the most thoughtful way. But how can you how do you expect to tell the story properly if you don’t have a grasp on everything the interviewee tells you?

Even if you’ve done all of the research in the world, interviewees will inevitably say things that leave you scratching your head. It’s just something that happens, especially when you’re talking to people about technical topics.

If asking a question will give you a greater understanding of the story, then ask it.

So, when someone mentions something you don’t fully understand, don’t hesitate to stop and ask for clarification. Ask for details. Ask for definitions. Even if you feel dumb for asking.

Wrapping up

Alrighty, that’s all we’ve got for day one of the series. Here’s a recap of everything we’ve covered so far:

  • Strong questions help you identify whether a character will be able to carry your story.
  • Do your research beforehand. It’ll help you ask better questions, and it shows the interviewee that you’re invested in making the best possible film.
  • Use open-ended questions like “Tell me about a time when…” to get detailed, often unexpected pieces of the story. Follow up and dig deeper when you hear something that interests you. Make it a conversation.
  • Use more targeted questions like, “Why is that important to you? and “How did that make you feel?” to really get at a character’s Big 3 Things.
  • Don’t be afraid to ask dumb questions. It’s your job to fully understand the story, so if a question helps you understand better, it’s worth asking.

If you have any tips or strategies of your own for asking strong questions, be sure to leave them down in the comments! I'll see you tomorrow for day two.