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Improve Your Question Skills: Watch Your Step

This lesson is a part of an audio course 5 Ways to Improve Question Skills by Dean Heffta

With any tool, there are potential traps or tripwires that we need to be mindful of – and questions are no different.

Here are seven that will help you stay out of the quicksand.


Believe it or not, my first watch-out is the question "Why." What's extra interesting is so many experts tell us how we have to ask why, the famous Japanese business method to get to the root of a problem called the "Five Why's," and the list goes on.

So what is it about this question that's so dangerous? Well, I'd bet if you think back to some experiences you've had with people asking you why – you know what I'm talking about.

A why question is the most likely question we can ask to invite defensiveness in others.

Think about it: Why was this done? Why didn't you tell me? Why did you think this would be good enough?

You see – why questions quickly direct the problem toward the person. When I'm asked why I think it was good enough, I'm left to defend my entire ability and judgment as an individual. I can then go into protection mode with defensiveness.

So what to do instead? The good news is nearly every Why question can be asked by another question – often a what or a how. Let's tackle some:

Why aren't you here yet? (what we really want to know is) When will you be arriving?

Why isn't this finished? What's prevented this from getting finished?

Why didn't they buy? What kept them from signing the deal?

You'll notice that with why, we can feel this impulse to defend, and there is no possibility or momentum that emerges. When we use what's and how's – we start seeing new ideas and the real answers we're looking for.

Trap Questions

Sometimes we end up using questions to paint people into corners. Some sales trainers even teach these as techniques to get buyers to yes. The problem is; you remove people's freedom, and over time they'll resentment you.

Its questions like "Don't you agree?" I'm forcing an agreement. Or the sales questions limiting choice "Do you want to pay in cash or finance it?" "Would you prefer the red or the blue?"

Or, how about…

Isn't that right?

Wouldn't you say?

Anytime I'm baiting people into an answer that favors me, it runs the risk of creating annoyance in the relationship.

Symbiotic Demands

A strange term for something that we experience all the time.

"I'd love to go to that new restaurant."

"It'd be nice to go on a trip this weekend."

"I don't remember where I put my keys."

These are non-questions, that are enlisting you to think, to try, or to help. When you hear the phrase – you begin working to decipher if it was a request or just someone thinking out loud.

You may even feel compelled to clarify with…

"Do you want to go to that restaurant tonight?"

"Would you like to get away somewhere for the weekend?"

"Do you want help in looking for your keys?"

So, if you find yourself with the habit of making comments that are really veiled requests – my challenge to you is to shift them into clear questions, directives, or requests.

"I'd like to go to that new restaurant. What night would be best?"

"A weekend getaway would really be so recharging. Would you be interested in a three-day trip?"

"I can't find my keys. Would you help me look for them?

See how much more clearly what you want and what you're looking for becomes?

Paradoxical Injunctions

This is where we ask for someone's thoughts or opinions on something. Then once they share, we punish them for it or maybe reject outright what they've said.

You've seen it happen, or maybe even done it.

"Adam, what are your thoughts on this new product?

Adam: "I like it. I think it could really be popular with the construction industry."

"That's a terrible idea unless you're looking for ways to waste millions of dollars entering a new market. I hope you don't have any other bright ideas like that."

You invited me to share, I answer, then you punish me.

If we look at our relationships over the course of time – when Paradoxical Injunctions are present – expect psychological safety to collapse. This leads to the disappearance of candor, open sharing, and innovation.

It's like calling a dog over in a kind voice to pet him, and then punishing it for coming to you.

Beware if you have a history of doing this.

Too Deep / Too Personal

I worked with a fellow many years ago who was well known for asking people – even one's he barely knew – remarkably personal questions. "How much did you pay for it?" "So, what led to your divorce?" and the list goes on. People who overheard these questions were startled at the topics he'd ask about. The consequence was a reluctance to get into a deep conversation, and if you did – you had to be prepared to have ways of not answering things you didn't want to share.

Connected to this is when our questions try to get too deep to the why of someone's behaviors or decisions. It can begin to seem too much like a therapy conversation that you haven't signed up for.

One litmus test if you have a comfort in asking deep and personal questions is reflecting on what your motivation is. If it's because you really want to be supportive when people are struggling – that seems fair – as long as you aren't trying to be everyone's rescuer. However, if you're just really curious – and the conversation is an opportunity to uncover information that exposes people simply because you want to gossip or to feel better about yourself – then beware of what that kind of questioning can do to the relationship.

Too Many!

You may have had an experience like this – you're talking with a sales rep – and before you know it, you're in the middle of what seems like Twenty Questions. They're asking about for how long, who, how many, which other, what else, and the list goes on. It can feel like we're stuck in a fast spiral, and the only benefit is to the seller who's loading up on facts.

When we're asking questions – we need to be clear on what few questions will get us the critical information needed.

If you're in a role where it's necessary to ask questions so you can best do your job – here's two things that can help. First, prune down to the key questions that are most necessary. Second, let them know what to expect. If people are expecting a presentation, but instead, you launch into an inquisition – they can be taken aback. Explain what the benefit is for them for you to ask questions and ask for their permission. "I have a handful of questions that will really help me best tailor our solutions to you. Would it be alright if I ask some questions of you before we talk about some of the things we do to help our clients?"

Never Sharing

If you look at a conversation as a type of dance between two people – if we are too focused on gathering information, the other person can begin to feel at a disadvantage.

You'll hear people say things like, "I've been doing all the talking." "You've been asking all the questions." "I feel like you know a lot about me, but I don't know anything about you."

Even if our intent isn't to be secretive, when we're asking all the questions – but never sharing anything about ourselves – we slow down rapport. Whether it's our background, our mistakes, our fears, or whatever that could be relevant to the conversation.

Rapport requires a sharing and understanding of each other's thoughts and emotions – if it's only one way – you lose the balance of understanding.

If you have this tendency, be more open about your own experiences in the areas the other person is sharing. When they ask you questions, don't deflect and take back control with another question (unless you're running an interrogation.)

There you go. Seven potential traps: Why questions, Trap questions, Symbiotic Demands, Paradoxical Injunctions, Too Deep/Too Personal, Too Many, and Never Sharing.

Your assignment is to reflect on which of these you may be at risk for and identify what you can do differently in the next situation where it may come up.

In our next session, we'll discuss the habits that can help us to develop our question skills.

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Written by

Dean Heffta

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