Get New Ideas by Email. Join 3k+ Readers.

How to Ask Good Questions: 5 Ways to Discover the Truth

A Gretchenfrage is the queen of all questions. It strikes deep to the core of an issue. It makes the person being questioned think deeply and hopefully come up with a genuine answer. The German word has its origins in Goethe’s tragic play Faust. Having sold his soul to the devil himself, protagonist Dr Faust is thrown off balance by a simple question coming from his beloved Gretchen: “Now, tell me, how do you feel about religion?” No doubt, a great question can make a difference. But what lends them their power? How do we best ask them if we want to discover the truth? And which ones – if any – should we avoid?

The Power of Asking Questions

As author Neil Postman put it, questions are “the principal intellectual instruments available to human beings”. They’re available to anyone regardless of status and education. Gretchen may be young and innocent, inexperienced and naive. Yet, she manages to perplex Dr Faust, the adept scholar and eager intellectual, with her probing curiosity. Questions, we might say, are a great equalizer.

They’re quite versatile instruments, too. Questions can be used to elicit information or persuade. They can be employed to assess someone’s level of knowledge or serve as a catalyst to establish a relationship. They can also be used as a means of control; in interrogations or job interviews, for example. Those who ask the questions tend to be in charge. Those who get asked feel the social pressure to reply. Sometimes, the absence of a good answer can be just as insightful.

So questions are powerful conversational tools. There are myriad ways to ask, let alone to answer them. While their usefulness will depend on the topic and context of the conversation, there’s one distinction pretty much all of them have in common. It’s the distinction between closed questions and open ones.

Closed vs Open Questions

Granted, the difference between closed and open questions is a pretty basic one. But it’s worth repeating as the foundation for the strategies to come.

Closed Questions

Broadly speaking, closed questions can be answered with a single word (Yes, No, Egypt), or with a short phrase (Down there., On my 18th birthday.). Closed questions tend to be:

  • easy to answer (How old are you?)
  • quick to answer (What time is it?)
  • useful to ask about specific facts or events (What revolves around the earth?)
  • useful to seek confirmation (Are we in agreement?).

This, of course, informs when they should be used. Jerry Seinfeld’s “secret technique for talking to regular people” illustrates the benefit of closed questions quite nicely. His advice is to ask people “questions to which the answer is a number. There’s always an answer.” People had no trouble saying how long they’ve been living in a place or when they started work, Jerry explains. Plus, they don’t have to reveal too much about themselves to a stranger.

A potential downside of closed questions is that you can easily get stuck in a taciturn one-sided conversation that becomes awkward really fast. Imagine someone asking you a series of yes/no questions for an hour. It’ll probably feel like an uncomfortable interrogation really fast. This is why it’s important to master the art of asking open questions as well.

Open Questions

As opposed to closed ones, open questions are much more likely to receive an elaborate answer. At least, that’s the rationale behind asking them. They tend to be:

  • great to make the person questioned think and reflect more deeply and share their thought process with you (How has it come to this?)
  • more difficult to answer as the respondent has to sift through all the possible replies in their head and structure their reply into coherent sentences (How can I ask good questions?)
  • more likely to elicit emotions, feelings, beliefs, wants and needs from a person (What happened to you?)

A potential downside is that the respondent is much more in control of where the conversation goes. They can change subjects, go on an endless tangent or engage in a Chewbacca Defense so incoherent that the answer is virtually useless. Yet, it goes without saying that there’s nothing intrinsically good or bad about using open questions or closed ones. Each has its own utility.

Still, it’s possible to answer a closed question with a long rant or reply to an open one with a single word. Whether they work depends on many factors, including the person we’re talking to, our relationship with them as well as the context of our conversation. Then there’s the question of the purpose of our questions and the goal we’re trying to achieve. For the sake of this list, let’s assume we’re aiming for the highest goal of them all, discovering the truth.

5 Ways to Discover the Truth

With the basic distinction between closed and open questions out of the way, let’s get more specific. Here are five approaches we can employ to elicit information and discover the truth.

1. Story-eliciting Questions

What happened?

The term Story-eliciting Questions was coined by Shawn Callahan, an executive coach who specialises in teaching leaders how to master business storytelling. Humans tend to think in narratives. As social psychologist Jonathan Haidt once put it, “our minds are story processors, not logic processors.” With Story-eliciting Questions, we can use this to our advantage by prompting a respondent to reveal information in the form of a narrative.

In his book Putting Stories to Work, Callahan has collected those questions that are most likely to get people to tell you a story. This is useful whenever we don’t want to be given a series of dry facts, justifications or opinions. Because stories tell us about a personal journey, how someone got from point A to B while overcoming struggles. For our purpose of discovering the truth by way of storytelling, the following of Shawn’s suggestions can work:

  • What’s one of the hardest choices you’ve made in your life? can be asked to reveal someone’s true character.
  • When have you said to yourself, “I’ll never do that again!”? is a question that prompts people to share a crucial life lesson.
  • What happened? is a universal story-eliciting question that can be used to follow up on everyday statements such as I’ve made a pact with the devil.

The example of Story-eliciting Questions shows the importance of knowing the purpose of our questioning before engaging in the conversation. One way to find the right question to ask is to reverse-engineer it from the kind of information we want to elicit.

2. Chunking Questions

Can you tell me more? What does it all mean?

Asking a good initial question is one thing. But what if the answer we get is incoherent? In this case, Chunking Questions can help. They’re useful for navigating the level of detail in a conversation and come in two flavours. We can chunk up or chunk down.

Chunking down is practical when our conversation partners’ answers are too general or abstract. Perhaps because the details seem obvious to them. Or because those details are incriminating. Questions such as Can you tell me more about…? can be used to steer the conversation and elicit the specifics from the respondent. As a follow-up to a Story-eliciting Question, it would prompt them to break down their narrative into smaller parts.

By the same token, we can chunk up by asking questions such as How does that fit into the larger picture? Sometimes people get lost in the details. It may be unclear how all those fascinating details fit into the larger story. Even for respondents themselves. So it can be worthwhile to chunk up, probe the details for their relevance or have your conversation partner put them back into the larger context.

If the person before us doesn’t happen to be a skilful and efficient speaker or storyteller, it’s probably necessary to chunk up and down throughout the conversation.

3. Calibrated Questions

How am I supposed to do that?

Calibrated Questions are the brainchild of former FBI hostage negotiator Chris Voss. They harness the power of open questions that start with how. These how-questions are then “calibrated” depending on the context of the situation. In his book Never Split the Difference, Voss notes two main purposes.

For one, they’re great for eliciting information from a counterpart who’s making demands you’re inclined to reject. According to Voss, “calibrated “How” questions are also a surefire way to keep negotiations going” as “they put the pressure on your counterpart to come up with answers, and to contemplate your problems”. Sounds like a great way to get people thinking and steer the conversation towards the truth, doesn’t it?

Calibrated Questions are an exception to the rule that open questions put respondents in control. Used smartly, you can keep someone’s mind pretty busy to come up with answers to your problems. All while they feel in control of the process. This is why calibrated questions such as How am I supposed to trust you if you don’t tell me the truth? are a cooperative way to say ‘No’ without actually uttering the dreaded word, or feeling guilty.

4. The Columbo Method

Columbo was a popular TV show from the 70s to the 90s. The cigar-smoking homicide detective was famous for his washed-out trench coat, rundown French car, goofy-looking basset hound and perpetually confused demeanour. He regularly investigated rather intellectual, high-profile murderers. Cunning killers who had planned their killings down to the minute detail.

The secret to Columbo’s method of questioning lies in his very persona. Make others feel “smarter than you are,” writes Robert Greene in The 48 Laws of Power. “Once convinced of this, they will never suspect that you may have ulterior motives.” Inspector Columbo knew how to make the suspects underestimate his intellect and break through any resistance to being questioned. Here’s how it works.

First, get people talking by asking them casual, random open questions. Faint ignorance, act genuinely confused and incompetent to make yourself appear harmless. Once people are put at ease, drop a question that gets to the heart of what you really want to know. With their defences lowered, your counterparts are much more likely to respond sincerely.

Columbo’s signature move, however, was that “one last thing…” he wanted to know after he was almost out of the door. Just when the suspects thought they got rid of the pesky detective. Just when they assumed the questioning was finally over. Just when they relaxed. The inspector turns around, scratches his head and drops an observation that leaves them (and the audience) at the edge of their seats. Does he know?

5. Alexander’s Question

What new information would it take to make you change your mind?

Sometimes we’re too obstinate to see the truth. Alexander’s Question forces respondents to reconsider their level of confidence regarding their decisions. Once we’re closing in on a judgment, we’re prone to confirmation bias. Groupthink can lead us to abandon independent thought and seek concurrence with others. When asking what it would take for someone to change their mind, they’re prompted to reassess the standards for their assumptions and decisions.

It can be useful to apply to ourselves, too. As Charles Vandepper, author of Applied Thinking for Intelligence Analysis, writes: “Alexander’s Question promotes analytical humility by forcing us to consider that our initial judgement might, in fact, be wrong.” In that sense, we can see it as an opportunity to look for evidence that would disprove our assessment so we can recalibrate it. Hopefully to uncover the truth in the process.

When the conversation happens within a group, and the stakes are high, we might want to consider Premortem Analysis, a method closely related to Alexander’s Question. It’s essentially an exercise in preemptive hindsight designed to catch fateful decisions before they’re implemented. By asking, Imagine our project has failed. What went wrong? the conversation is reframed, and dissent is legitimised. It goes to show how simple questions can make all the difference.

BONUS: Beyond Words

Beyond Words?

Even the best questions will fall flat if your counterparts don’t recognise when you’re asking them. This is where a more deliberate use of the tone of your voice comes into play. Roughly speaking, we use downward inflections (voice falling at the end of a sentence) to convey factual information. We use upward inflections (voice rising at the end of a sentence) to signal curiosity and our intention to get a reply.

The great thing about upward infections is that we can use them to turn any piece of information into a good question. Simply echo a whole sentence, phrase or the last few words someone has said, ending on an inquisitive upward inflection. Try it out and see how it prompts people to elaborate on whatever they said. The best part is, by merely echoing the other person, you don’t even have to think of a particular question to ask.

Here’s a final suggestion, though. How is your question supposed to work if people don’t have time to answer it? So remember to pause and give your counterparts time to gather their thoughts and formulate an answer. The more profound your question, the more time someone will need to consider an answer. As every teacher knows, learning to endure the endless awkward pause is the gateway to the most truthful answers you’ll hear all day.

Closing Thoughts

A Gretchenfrage may very well be the queen of all questions. But as hard-hitting as such questions are, they’re usually part of an excellent strategy. Without a flexible approach that adapts to the responses of the person being questioned, getting truthful answers is left to chance. Without a clear goal, we can’t even know if our questions have been answered.

The secret lies in combining and balancing approaches such as the ones above. The right words, perfectly delivered and spoken at the right moment, can indeed make a difference in discovering the truth. There are, however, some questions you should be careful of. To learn more about them, check out my bonus content for paid newsletter subscribers with five questions to avoid.