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4 Proven Ways To Ask Powerful Questions For Better Results

Do you want to show your boss that you’re a STRATEGIC THINKER?

Would you like to motivate your direct reports to bring their BEST PERFORMANCE?

When speaking to a key customer, want to get the RIGHT INFORMATION?

If you answered yes to any of these, you need to start asking better questions. 

And not just any questions – Powerful questions that lead to better results.

In order to get better results, you’ve got to get the question right.
However, not all questions are created equal.

If you want to know what new product your customer needs, which line of questioning do you find more effective:

“What new product do you need…what’s missing in your line of products?” 


“What’s your current biggest current challenge…what product or service could help you overcome this challenge?”

Here’s why the second one is more powerful – The customer might not know what they need.

Your question has to be good enough to make your counterpart think, act or whatever it is you hope to accomplish with your question.

Furthermore, questions designed to show someone how smart you are, for example, can lead to the wrong result.

Certain questions can do more harm than good.

Consider this scenario:

You want to show your boss’ boss that you’re a strategic thinker. You ask:

“Is our current strategy to establish our market position by taking a loss on our products like Amazon did in the 90’s and then once we’re established go public like Facebook did in 2012?”

How do you think the big boss would see you?Image result for google images smarty pants

Probably more a Smarty Pants than someone who asks smart questions.

And this is exactly what a good sparring partner does – asks questions to help others make better decisions.

So if you want to be seen as a strategic thinker and “go-to” sparring partner, don’t do it like this guy.

As my mother taught me, nobody likes a Smarty Pants.

In the end, a big part of asking questions comes down to common sense.

After all, the quality of the question determines the quality of the response.

In this post, I aim to show you how to ask questions that lead to the results you seek (info, opinion, action).

You’ll also learn pitfalls to avoid (e.g. MrSmarty Pants).

Cold Hard Facts

According to current research done by Todd B. Kashdan for The Harvard Business Review:

“A child asks 300 questions a day. By middle school, the number is down to practically none. By adulthood, our disposition toward questioning can range from the timid to the hostile.”

Certainly this changes when someone becomes a professional, right?


OK, but certainly some industries and professions are better than others, right?

You’d be surprised.

I’ve read that only 30 percent of salespeople are ready for a buyer’s questions.

If none of the above benefits speaks to you personally, what about this one?

Do you want to GET SMARTER?

Since you’re reading this article, I know you do.

The best and quickest way to get smarter is by asking questions.

Whether you’d like to learn a new skill or learn about a new job opportunity, you’ve got to be proactive.

For example:

Questions to someone with a skill you would also like to develop:

  • “How did you learn how to ________?
  • “What was the hardest part of the learning process for you?”
  • “What advice can you give me starting out?”

Questions to someone at a target company:

  • “Who’s the best person for me to talk to about this opportunity?”
  • “What do you like best about working for _______?  Worst?”
  • “What do I need to know about working for ________?”

By the way, the days of someone planning your career and ensuring you move up the ladder are long gone.

If you don’t look and ask about new skills and opportunities, they won’t come to you.

Sadly, employee development is not a top priority at many firms.

Furthermore, budgets are being slashed like never before.

Most people are just looking to stay afloat themselves. You know from Hollywood what happens when the big ship hits the fateful iceberg…

And despite what Silicon Valley might say, Google, Wikipedia or Siri can never replace a real-life sparring partner.

If you’re still not convinced, here are 3 BENEFITS EVERY MANAGER NEEDS:

  1. BETTER DECISIONS – Asking a trusted partner a question helps you clarify thoughts for better decisions. At the very least, every additional perspective makes for a better-informed decision.
  2. CULTURE OF INQUIRY – When leading a team or business unit, asking questions creates a culture of inquiry, rather than blame. If your team were a garden, think of inquiry as a healthy fertilizer, blame a toxic pesticide.
  3. TRUST – There’s no better way to build trust than asking the right question – you help others discover hidden strengths, too.

Despite the trendy tips and tricks you might learn at a “Good Manager” seminar, nothing is more effective than a good question.

Truth be told, it would take a book to list all the benefits for both asker and asked.

Then how can we explain then the precipitous drop from 300 to 0 in 10 years or less?

The Psychology of Ignoring Facts

I’m not a psychologist but I’d argue that the explanation for this phenomenon is pretty straight forward.

People want to be seen as smart (or at least not stupid).

Asking a question shows that you don’t have the answer (at least not all).

Newsflash – No one has all the answers!

If they act like they do, they’re lying.

If they’re in a position of leadership, they’re making a big mistake.

Here’s Forbes on why “Great Managers Ask Questions”:

“Managers who master the art of questioning act as coaches to their team. They challenge the status-quo and reframe problems, liberating an organization to think freely and out of the box. Great managers often have a questions-only conversation with their staff.”

Ironically, asking questions is how you do learn a lot.

Acting like you have all the answers is a great way to keep you dumb.

It’s also a terrible reflection on you if you act like you know what someone is talking about and they find out later you didn’t have a clue.

Another reason people may avoid asking questions is to avoid appearing “difficult”.

Have you ever thought: ‘If I ask too many questions here they might think I’m negative or trying to find a way out?’

I have.

But then I thought: ‘No, I’m going to ask it anyway. I want to know the answer and my question could make them think of something they haven’t yet considered.’

Out of fear of rocking the boat or sounding stupid, there have certainly been times when I haven’t asked the hard question.

However, part of my development has been to face that risk and have the courage to ask the question.

Besides, if your counterpart values your opinion, they’ll value your question.

If they don’t, your question could rub them the wrong way.

But then, why would you want to work for someone who doesn’t value your opinion?

Here’s a piece of advice from a non-psychologist: TAKE THE RISK.

And despite what they say, companies don’t always value questions from their people.

But forget all these stats and studies for a second.

Take a few minutes and reflect on how you think about this topic – 

What does your question-asking picture look like (child to teen; professional to manager)?

If you’re asking fewer questions than before, what are the reasons?

If you’re asking more, why?

At the end of the day, this is the only research that is truly relevant for you.

4 Powerful Techniques

Here are four techniques to help you ask more questions:

Technique #1: Go deep.

Don’t settle for a short or incomplete answer.

Ask follow-up questions based on the response you get from your first question.

Of course, it helps if you know the specific information you want.

However, this is not always the case, especially if the nature of your question is exploratory (e.g. “What’s your experience with ______?”).

Furthermore, questions often become exploratory based on the answer (e.g. “Oh, really. What was that like?”).

Of course, open questions (what, why, how) increase your chance of getting more complete answers than closed ones (q’s that can be answer with “yes” or “no”).

Which question do you think would generate a better quality answer?

“Did you enjoy your last performance review?”


“How do you feel about your last performance review?”

In stark contrast to many communication experts, I don’t think you need to avoid closed questions.

First, it takes a lot of practice for this (I’m an experienced coach and far from perfect).

But more importantly, it doesn’t really matter how you start (as long as you start!).

However, a closed question does usually require a follow-up question – which is great, in my opinion.

Image result for ping pong images

With two Q & A’s you’ve already got a ping-pong exchange – a 2-way dialog is a big goal of any line of questioning!

What do you think of this exchange?

Q: “Did you enjoy your last performance review?”

A: “Not really”.

Q: “Why is that?”

A: “I didn’t think it was fair because I was away on sabbatical for over half the year – of course my numbers were down!”

The way I see it, two questions are better than one – you’re already “going deep”.

What’s important is that you continue the exchange, not how you start it.

There are, however, a few pitfalls you need to be aware of…

For example – the ‘mismatched words and body’ pitfall.

If you are genuinely interested in what your counterpart has to say and your voice and body match your words, the exact words don’t matter. They will feel your intention.

On the flip side, if you use perfect words but your non-verbal communication is hostile…

As the Germans say: “Der Ton macht die Musik” (it’s not what you say but how you say it).

You could just as easily get a short, non-specific answer to an open question.

Consider the following exchange:

Q: “How do you feel about your last performance review?”

A: “Not great.”

This requires a follow-up question as well.

If you did get this short answer, you could follow up with something like:

“What makes you say that?”


“In what way was it not great?”

Another big pitfall to be aware of is the negative effect that “why” can have in some situations.

A question that begins with “why” can put people on the defense – even if that’s not your intention.

Imagine this scenario:

You’ve just completed an important task and your boss asks you:

“Why did you do it that way?”

I don’t know about you but I would hear it as a judgement and immediately feel compelled to justify why I did it THAT WAY.

Perhaps he or she is genuinely curious. However, this question isn’t asked when that’s the case.

How would you feel if your boss instead asked you:

“Could you walk me through your decision process here?”


“How exactly did you come to do it this way?”

Again, it’s not what you say, but how you say it.

If either of these exploratory questions were asked in a hostile voice, the judgmental intention of your question would be clear.

It is possible to ask “why” questions without putting people on the defense. However, this is not easy.

It requires a deep level of trust and a strong understanding of your counterpart’s behavior.

Sadly, trust is often damaged during difficult conversations between managers and reports (e.g. poor performance review).

A good manager sees a difficult conversation as an opportunity to build trust.

The way you ask a question, including body language, tells your counterpart if it’s coming from a place of curiosity, criticism or elsewhere.

The final pitfall to be aware of is ‘ignoring culture and context’.

Even though I’ve lived and worked all over the world, I hesitate to bring up culture with most topics.

There is a reason for this and it’s not because I no longer want to be seen as a “cultural expert”.

By the way, I no longer want to be seen as a “cultural expert”.

In my experience, personal differences usually play a bigger role than national ones.

However, both play a significant role in this topic.

The quality of information you get greatly depends on whom you’re asking and the situation in which you ask it, i.e. “context”.

I find closed questions work just find with most Brits – a simple prompt might give you the information you’re looking for. They might even help you ask the right question.

The Germans, on the other hand, might give you a literal “yes” or “no” but no more. Not always helpful, but correct.

The Germans are nothing if not correct. Trust me, I’ve lived here for 20 years.

And when I think back to my early days in Germany, trying to get information on the phone was like pulling teeth…from a horse with no teeth.

My poor German certainly didn’t help but neither did my counterparts’ reluctance to give me extra information (info that would have clearly helped!).

A sensitive situation can turn unproductive or even hostile if you’re not careful.

Technique #2: Be curious.

Before asking a question, check your motive.

Ask yourself: “Do I really not know the answer?”

Again, I’m not a psychologist but I would guess that many questions are asked even though the answer is already known.

As previously mentioned, questions can be used as a tool of criticism and worse.

Imagine this scenario:

  • You’ve got an important team meeting on Thursday.
  • You have a bad stomach bug and can’t come in to work.
  • You call your boss on Thursday morning, apologize and explain the situation, i.e. your illness.
  • On Friday you come into the office and your boss asks you why you didn’t come to the office for the important meeting yesterday.

You don’t have to be a mind reader to infer from the question that they don’t believe you were really ill.

When a report makes a decision that pleases you, do you ask them why they did it?

I’m guessing no.

Sadly, we usually ask this question when we’re unhappy with a decision or its undesired outcome.

If you do want to build trust and motivate your reports to bring their best performance, ask yourself these two questions:

  1. What is the intention behind my question (disappointment, criticism, curiosity)?
  2. What am I trying to communicate with my question?

PRO TIP: If it’s not a real question, make a clear and direct statement instead.

When someone is disappointed in me, I’d rather they tell me directly than communicate it indirectly in a question.

Which would you prefer?

“I was disappointed by the outcome here.”


“Why did you do it THAT WAY!?”

Whenever possible, make a clear, direct statement followed by a question such as:

“I was disappointed by the outcome here. Could you walk me through your decision process?”


“How exactly did you come to do it this way?”

If it’s a super sensitive situation you could try:

“Can you help me understand how…?”

Even when hard, I believe people prefer straight talk. I certainly do.  

Plus, I don’t have the time or energy to decipher someone’s hidden meaning.

 If you clarify the intention of your questions when you ask them, you can avoid unnecessary conflicts.

Anyway, people aren’t stupid – they’ll usually feel the real intention behind the question anyway.

The next time you’re at a team meeting, try this:

Before asking a question, tell your counterpart if it’s coming from a place of curiosity, challenge, etc.


“This question is designed to challenge you: Have you looked at all possible options here?”

And if your question comes from a place of curiosity, tell them that, too.

Technique #3: Use silence.

People aren’t always ready to talk.

Furthermore, they may need time to think about their answer – or maybe they’re thinking about the intention of your question:-).

It doesn’t matter. You can’t read their mind anyway.

What you can and should do is wait.

What you should not do is jump in and answer the question for them. Or worse, jump in with another question that could distract, irritate or confuse them.

Just how accurate is an answer that comes from you, anyway?

If your intention is to hear their answer in their words, don’t muddy the waters with yours’.

If you really want to know how a report came to a decision, you want to hear it their words.

Don’t lead them to the answer you want or assume is the right one.

Never assume.

How would you react if you know that your boss wants you to improve your public speaking skills and asks:

“Do you want this new position so that you can improve your public speaking?”

Even if it’s not the main reason, I’m sure you’d let them believe it was part of the reason.

That is how humans tick.

If you want the real reason, try this question followed by these 4 simple steps:

“What are your reasons for wanting this new position?”

  1. Wait for answer.
  2. Listen closely to response
  3. Wait some more.
  4. Ask follow-up question.

By doing it this way you give them and yourself time to think.

More importantly, you create the space for the real and additional information to come out – sometimes this last bit is the most valuable.

Bottom line – silence is your friend.

By the way, you never know how best to follow-up until you’ve heard their response.

If someone tells me they want to improve their public speaking skills, I don’t need to ask a question about it.

If they tell me they’re unclear about their reason/s, I might ask:

“When you saw this job posting, what was the first thing that got you excited?”

If they tell me that they want to raise their visibility in the company, I might ask:

“What aspects of this role do you think would help you with this goal?”

In fact, I don’t believe you can really hear what your counterpart is saying if you’ve already got your question ready to fire off.

Technique #4: Don’t interrupt.

Closely related to don’t assume is don’t interrupt.

In fact, this technique is very much connected to all of these techniques.

By applying this technique, you automatically apply the first three:

  1. Go deep by allowing the space for a real exchange,
  2. Be curious by letting them use their own words, and
  3. Use silence by waiting for additional thoughts to emerge.

By interrupting, you signal that you don’t value what your partner is telling you. 

Furthermore, it signals that what you want to say or talk about is more important.

This might not be your intention. However, this is what it communicates.

Even if you’re not getting the answer or information you want, let them finish.

You can always direct them back to your question.

Take Action Today

Asking questions is important. It’s also easy.

To some people (and cultures) it comes easy. For others, it takes practice.

But, it’s an ability that can be relearned and developed.

More than just a competency for your “skill set”, it’s also an attitude for a powerful “mindset”.

On the topic of building new skill- and mind sets:

How good were you at ‘drawing boundaries’ at the beginning of your career?

It took me years to learn this skill – I’m still learning!

But, I developed it. I learned the pitfall of over-committing and giving less than 100% just to avoid saying “no”.

I’d have burned out long ago if I hadn’t. I’m guessing you could say the same.

Here’s an easy 3-step formula you can use to ask more powerful questions:

  • Ask yourself: “Do I already know the answer to this? What’s my intention behind the question?”
  • Once you understand your intention, ask your question and listen to the response.
  • Ask follow-up question. Repeat.
The very best advice I can give you is this: If you don’t like the answer, change the question.

Thanks for reading!


P.S. For advice on how to ask better questions for better results, book a FREE CALL with me.

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  • Thanks for the article, Tim!
    It really made me thinking how I ask my questions and I’m planning on practicing it more in my daily life.
    The questions really work for different people (employees, managers and also very much for me as a consultant).

    I can image to use the techniques as reflection questions for participants in my leadership trainings.

    So thanks a lot!

  • Excellent article Tim. The power of asking questions and engaging in exploration and true dialogue with people is an art hugely underappreciated. Many of the best managers I have worked with are like this: They care about their people and use questions to generate understanding and trust. This is also a feature of teams and businesses that have high engagement level and a strong culture. Of course questions badly executed or used in an accusatory style can have the opposite effect.

    Thank you once again for a superb article.

    • Yes, exploration and true “2-way” dialogue! Questions used as a part of 1-way communication don’t cut it! Thanks for sharing, Steve.

  • I really like this article. Getting the right question is always something I really have to think about. Don’t ask a question you know the answer to is a great idea. It is surprising the stats about children and the number of questions they ask! A colleague of mine is fantastic at asking really good questions to help people think and I notice he takes his time formulating a question. He’s not afraid of the silence and that point is often the downfall of so many of us. Two questions being better than one is a clever idea and it’s often the deepening of the questioning that makes such a difference.
    How about we start a list of powerful questions? I know I’ve seen one somewhere so if I find it I’ll post in in the comments.

    • Thx Laurence. Yes, a list would be great if you can find it. In addition to silence, I think the simplicity of the question is also key – how is that?, what do you mean?, etc.