“I just love asking questions. I love people. It’s in my DNA. I’m both cursed— and blessed.” Larry King

So you’ve got a problem. Another one. It’s landed on your lap and you have to solve it. Fast. It may be with your partner. Your colleague. Your boss. Or with getting more sales.

Fact is — it’s yours. And your back’s against the wall.

What’s the best solution?

Answer: Ask the right questions.

Lessons From The Cradle

“Asking questions is what brains were born to do.” Alison Gopnik

I learned at an early age not to ask my parents too many questions. Because I rarely got answers that made sense.

“Why doesn’t that sign in the shop window (‘To Let’) have an ‘i’ in the middle so people know there’s a toilet in there?”

“No idea.”

“What does ‘sets’ mean?”

“Don’t know. Ask your father.” (She thought I’d asked about sex, not sets.)

I came to the conclusion that my mother was either very dumb or very busy. Either way, I learned to keep quiet until I could ask in such a way that my questions weren’t ignored.

The ‘Why’ questions children ask aim to open a vault most are too young to understand.

How can anyone tell a child in less than ten words about the business of leasing shops? And the art of commercial enterprise? Especially when my reference point involved spelling errors and mispronunciation rather than the bigger concept at hand?

At age seven, commercial leasing was better left alone.

Ask A Stupid Question: Get A Stupid Answer

“The art and science of asking questions is the source of all knowledge.” Thomas Berger

If you’re in a role where getting results is important, then the quality of your questions better be good. Because they’ll dictate the answers you generate.

Questions starting with ‘why’ rarely gather new information or reveal the answer needed.

‘Why’ questions can sound like you’re out to blame or accuse. They don’t lend themselves to opening a dialogue and getting to the heart of issues. More to confirm a suspicion.

If you’ve ever been head-to-head with a child asking never-ending ‘why’ questions, you know the loop you’re in.

Any answer you give is followed by: ‘But …why?’.

The ‘but’ negates any plausible reason offered. Meaning you’re back in a never-ending Q&A to satisfy their curiosity.

It’s how they learn to engage with their world. … And control the conversation.

In the gentle art of relationships, business or sales — the quality of your questions dictates the quality of your answers.

While my “to-i-let” question kept me guessing for a few years, the lesson I learned was to ask better questions.

Ones that couldn’t be dodged with blank responses.

Parents of teenagers often fall into the ‘why’ pit.

“Why weren’t you home by 10 pm like you promised?”

“Why did you take the car out when I asked you not to?”

“Why aren’t you listening to me?”

Or in relationships:

“Why do you stay late after work?”

“Why don’t we go out to dinner any more?”

“Why don’t you help around the house?”

It’s similar with emerging leaders.

“The ability to ask the right question is more than half the battle of finding the answer.” Thomas J. Watson

Some of these emerging leaders are establishing their business. Others are running departments or organisations.

In the heat of a moment, the reversion to ‘why’ questions shows their apprenticeship is incomplete.

For anyone on the receiving end of a ‘why’ question, they’re hard to answer without sounding defensive.

‘Why’ questions are lazy questions. They place the work of ‘thinking’ onto the receiver.

Rather than the questioner taking time to frame a question that moves the conversation further, they’re throwing the concept, structure and resolution onto someone else.

Much like my ‘to-i-let’ question did. When you have no idea — you have no starting point.

On a personal level, the answer to a ‘why’ question is buried so deep in one’s subconscious that answers require counselling sessions to flesh out nuances.

“Why didn’t I apply for that job?”

“Why wouldn’t he go out with me?”

“Why didn’t I see this coming?”

Theses questions achieve no more than a spinning top twirling in ever-shrinking circles on a table. Before landing flat on the floor with a loud thunk.

The essential link for anyone wanting to ask better questions, whether an emerging leader, a parent or a young person is to improve the skill of asking questions in these five different areas.

#1. Observe More.

“Management teams aren’t good at asking questions. In business school, we train them to be good at giving answers.” Clayton Christensen

Observation requires more than a quick glance. It’s in seeing an object, a person or a problem in its environment that you can build better questions. On-demand answers miss the subtle. Avoid intricate layers. Skip depth.

Instead of:

Why won’t my team stay on task and finish a project on time?


  • How are the team dynamics working for or against the outcome I want?
  • Which team members are on track and which seem easily distracted?
  • What skill sets could be missing from the team that need addressing?
  • When does the team produce their best work?

2. Be Curious.

“I’ve always been really curious about things and slightly confused by the world, and I think someone who feels that way is in a good position to be the one asking questions.” — Terry Gross

When a biologist or engineer gets curious, they go deep. They’re searching for what isn’t obvious on the surface. And this means not bringing any pre-set judgement to the problem.

Being curious also means being opening to vulnerability. It doesn’t mean having all the answers.

Scientists publish their mistakes. They don’t hide them and pretend the research didn’t happen. This advances the field — it doesn’t make the original author look ridiculous.

Instead of:

  • Why are we failing to find an answer to this problem?

Instead ask:

  • What would the solution to this problem solve?
  • If we looked at the problem from the perspective of an end-user, how would they want this to look?

3. Recognise Patterns.

“A person is a pattern of behavior, of a larger awareness.” Deepak Chopra

Nature provides most answers to our problems. Whether in an engineering field (biomimicry is a fascinating area of research-based design solutions drawn from nature) or a personal one.

Patterns are self-emulating. Get the original pattern right and it’s possible to scale the design so it consistently works. Get it wrong and it means pulling down original pre-cepts to start again.

Instead of asking:

  • Why is a solution not coming together?


  • What animal or plant in nature has already solved this problem?
  • Who can help me think about this problem from a different perspective?

4. Show Empathy.

“Genuine questions are not leading to an ask in return.” Brian Grazer

Design schools like IDEO ask its students to ‘walk in the shoes’ of those their design solution aims to help.

From field work and embodiment of the problem, a different viewpoint appears.

The questions aren’t about fast solutions for economic rationalisation, rather the environment a community or person inhabits and how they’ve adapted to it.

Instead of asking:

  • Why does this problem exist?


  • How can I get closer to the source of the problem?
  • What can I do that will help embody the issue?
  • How can I make this solution easier and more practical?

5. Be Present.

“We get wise by asking questions, and even if these are not answered, we get wise, for a well-packed question carries its answer on its back as a snail carries its shell.” James Stephens

Seth Godin solved a problem for a not-for-profit organisation selling glasses in India. Women weavers, whose eyesight was failing as they aged, could no longer contribute to the family’s economic needs.

The marketing problem: the glasses( which were within an affordable budget and needed) weren’t selling as expected.

While Seth Godin’s solution was brilliant (he reduced the range of options available and streamlined the buying process) — he could only do this because he was present to the cultural nuances involved in ‘buying’ a product.

While ‘being present’ was essential, Seth also:

  • Observed
  • Brought his curiosity into play
  • Recognised patterns occurring in the buying behaviour (and non-buying behaviour)
  • Empathised with the user (by working through the buying process)
  • And was present to cultural differences

Questions were flipped from:

  • Why aren’t these glasses selling?


  • What’s causing resistance in buyers who clearly need the glasses and can afford them?

Flipping the focus meant changing the lens.

It’s too easy to get caught in how our own insular culture and environment works. Asking better questions can mean wearing different shoes, changing glasses, shifting environment and looking to different industries to see how others resolve problems.

Do the questions you ask reflect your mind’s … ‘To Let’ sign?

“How dare you settle for less when the world has made it so easy for you to be remarkable?” — Seth Godin

Sometimes it’s easy to vacate the mind, hanging up the ‘To Let’ sign because it’s easier to go with the flow and not make a ruckus.

Are your questions asking someone else to put the dots together rather than spending time to train your mind to ask better questions?

Ones that help others tackle issues from vastly different paradigms?

Let’s put the ‘I’ back in ‘To Let’.

And no … this doesn’t mean putting things down the toilet.

Note: the word ‘toilet’ is from the French word toile (meaning ‘cloth’). In English ‘toilet’ referred to coverings made of textile: a wrapper for clothes (in Scotland), or a shawl or covering used while being shaved, for example.

For example: In 1714, English translators of travel books may write: The ordinary citizens Wives and Daughters wear a kind of Toilet on their Heads, with a long Fringe which covers their Faces, and drives away the Flies like Horse-trappings.

So, let’s put the ‘I’ back in ‘To Let’ and regain a sense of ownership and responsibility by asking questions that unpack concepts and leverage thinking.

Rather than posting ‘brain space for lease’ by dumbing down questions that leave other people hiding from blame.

Hot Tip:

Asking better questions starts by thinking more openly. More creatively. More inclusively.

It starts with the habit of turning up in your life with an attitude to observe more, be more curious, recognise patterns, showing empathy and be more present.

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Originally published at blog.usejournal.com