How Asking the Right Questions Will Take You Far

Tweak questions, shape answers.

You might think there’s not much you can do to influence the answer you receive to any question you ask. After all, answers mostly depend on the answerer. Or do they? I used to think so too. But we’ve been so wrong! Turns out, we can shape answers — or at least point them in the right direction — by tweaking our questions. The secret lies in choosing the right words. Two questions with the same purpose, but with a different word choice, will probably yield different results. The “how” matters more than the “what”. And the answer depends on the answerer as much as it depends on the questioner.

I’ll further illustrate this point with a brief example:

Picture two tribes living in two different villages in the same rainforest. One of them is known as “The Tribe of Liars”. The other one is “The Truthful Tribe”. Members of The Tribe of Liars will always tell you exactly the opposite of the truth, whereas members of The Truthful Tribe will tell you nothing but the truth, since they don’t know how to lie. You would like to visit the village where The Truthful Tribe lives to interview them about their lifestyle and traditions. So you set sail on an expedition to the rainforest. You follow the map that takes you to a spot where the path splits into two smaller ones. A man, who belongs to one of the two tribes, is standing right in the bifurcation. You need to pick one of the two paths, only you don’t know which one takes you to The Truthful Tribe’s village. You decide to ask the man standing at the entrance. But keep in mind you don’t know which tribe the man belongs to, so he could be telling the truth, or he could be lying.

What’s the question you would ask to get where you want to go?

If in a hurry, you might impulsively choose the most straightforward question, “How do I get to The Truthful Tribe’s village?”. Think twice! How would you trust the answer to such a question? You don’t know which tribe the man belongs to. If he belongs to The Truthful Tribe, he’ll tell you the truth. But if he belongs to The Tribe of Liars, he’ll send you straight to their own tribe’s village.

So, now you feel tempted to ask, “How do I get to The Tribe of Liars’ village?”. But beware! If the man standing there belongs to The Tribe of Liars, he will eventually lie to you, and send you to The Truthful Tribe’s village. However, if he belongs to The Truthful Tribe, he’ll tell you the truth, and send you to The Tribe of Liars’s village, since that’s what you’re asking him.

In the above example, mentioning the exact place you want to get to (or the one you don’t want to get to) in your question seems to send you to an unknown destination.

How could you narrow down the possibilities? Is there such a thing as a “sure bet” equivalent question, whereby you can never go wrong? Is there any way in which you could get someone to respond exactly what you need to know?

Take the following question, for instance:

“How do I get to your tribe’s village?”

By asking this question, you’ll always be pointed toward The Truthful Tribe’s village, regardless of which tribe the standing man belongs to.

That’s the question you need. The one that will always take you where you want to go.

If we extrapolate the above depiction to a real-life situation, I think there’s always an equivalent question for most circumstances. There’s really such a thing as a million-dollar question. And it pays to take the time to craft it because it will yield the million-dollar answer.

Now think about this for a minute. Do we really have the power to choose the answer we want to receive to any question we ask? Well, yes, in a way. Suppose you want to know something, get somewhere. There could be one question that will take you there for sure. Other questions might take you nowhere, or they might take you anywhere. A simple question can make you or break you. It might save you, or it might endanger you.

I was 13 the first time I heard the tribe riddle. I always found it to be a perfect portrayal of the way asking questions really works. But most importantly, it shows that, even for ill-intentioned people or risky contexts, the right question can turn a situation to your advantage. It could even wipe out the chance of going wrong. Power can shift from the answerer to the questioner with just one question, and even when you’re the one who doesn't know something that your answerer knows, you still get to influence and “customize” the information he/she gives you.

It’s about mastering the art of asking killer questions, which could translate to:

• being more efficient
• better management of interpersonal skills
• professional growth
• a potentially life-saving strategy

Smart questioning can be the difference between all or nothing. All you need to do is to change your approach.

A few years ago, I was waiting for a friend to pick me up. In the meantime, I did some channel hopping just to kill time. I ended up watching about 20 minutes of an episode of an Investigation Discovery show. I don’t remember the name of the program, but I do recall the girl who was speaking. She had survived the attack of a women’s serial killer. She believes one question saved her life. The killer had told her he believed in a better tomorrow. When he was about to finish her, she asked him, “I’m a believer too. Will there be a tomorrow for me?”. He stared at her, and for some reason, he chose to spare her. He left as quietly as he had arrived.

That’s just about how powerful a question can be.

Here are some specific benefits of learning the art of asking questions:

• An opportune question can save you a lot of time. It might provide guidance or spot potential issues.
• A good question is a magnificent tool to avoid misunderstandings and communication shortcomings.
• A tricky question can neutralize ill-intentions.
• A moving question can resonate with someone and stir emotions.
• A wise question might turn the odds in your favor. It works as a smart — and hopefully well-intended — manipulation technique.
• A disarming question makes people let their guard down and be more receptive.
• A provocative question sparks interest and gets a conversation going.
• A strategic question might prove life-saving.

Now that you’re aware of the important role questions play, it’s not only useful to use it to your advantage but also to make sure you understand what you’re being asked and how to respond properly.

Learn to recognize manipulative and tricky questions. The ones that intend to make you say more than you’d like to, to make you contradict yourself, to compromise you, to confuse you. Questions that leave you trapped with no easy way out.

Asking the right questions is mandatory when dealing with kids, who might be elusive to more obvious questions. Besides, they are the masters of questioning. They try really hard to get what they want (candies, toys, play time, etc), so they are skilled manipulators by nature. The 4-year-old daughter of a coworker wanted her dad to take her to the park, so she asked him, “Dad, you know you’re my king? What would you tell your princess if she asked you to take her to the park?”. With a question like that, do you really think “No” was a likely answer?

A friend of mine met a guy who came to work as a business consultant during a short period of time for the same company she worked for, and she immediately felt attracted to him since the moment she saw him. She knew he would stay for a few months only, so she wasn’t really expecting a relationship. She had recently divorced, so the last thing she wanted was a close attachment. One night they were hanging out at a local bar, and they got closer. So she asked him, “You’re not married, are you? I would hate to date a married man since my husband repeatedly cheated on me with his coworkers.” He said, “I’m not married”. Turns out he wasn’t married, but he lived with his partner and had two kids. She then told him he had not been honest with her. He said, “I have, you just asked the wrong question.”

Another close friend had an ugly dispute with a coworker. At the time, my friend and I worked together. Turns out our coworker had made a mistake, but she didn’t want to admit it. Her omission had compromised an important client. My friend just wanted her to be accountable for the damage and help her solve the issue. It had turned into a battle of egos, as they were both feeling under attack. So, my friend received another furious reply from our coworker. She was about to reply back when she asked me to come and help her. She said, “I’m trapped here. I don’t know what to tell her anymore. I don’t want this dispute to go on forever.” She wanted to send a final mail asking her something along the lines of, “Will you just admit you screwed up and help me clean your mess?”. Then I told my friend, “Wait, let’s pretend it doesn’t matter who screwed up, what do you really want? You want her to help fix the mess?” My friend nodded. I told her, “Well, then I’d tell her something like ‘Dear Xxx, we’re getting nowhere here, and we could really use this time for something way more productive. Whatever happened, we can’t undo it. What really matters now is that we need to help this client. Can I count on you for this?’”. My friend sent her the email. She received a response in under 10 minutes. “Yes, I couldn’t agree more. You can count on me. We’re on the same boat here.” Maybe she didn’t get a confession, but she received enthusiastic cooperation. The idea behind that last mail was to ask her something she couldn’t say no to unless she wanted to get into deeper trouble at work.

I believe a good question just pops up if you give it the opportunity, but there’re a few ways in which you could make sure you’re not leaving out anything crucial.

• Each time you come up with a question, think how and where it could go wrong. Think about all the possible interpretations the question admits. Some limitations could be a very narrow range of answers (or a very broad one), an ambiguous answer, lack of clarity in the question.
• At times, it’s better not to be too obvious. It could be useful to approach the question from a different angle. Remember that staring directly at the sunlight might burn your eyes. It could be better to orbit your subject than to land on it. But this is not always the case, depending on the situation, you might want to be as direct as possible. You’ll learn to develop a “sixth sense” that will help you read between the lines and tell which is the best way to ask something.
• The truth is that, usually, you won’t have the time to craft your question. So you’ll need to sense it. Just stop thinking, observe the situation without judging it, and your subconscious will probably tell you what to do (and what to ask).

Mastering the art of questioning can change your life for the better. Awake the wise one within you, and you can never go wrong. You’ll get used to thinking about the type of answer you want before asking your question.

Have you ever seen or been through an experience where a question made ALL the difference?