How to ask questions to find out anything from anyone

How to ask questions to find out anything from anyone

Why do I sit at the back seat of our car?

I looked down, laughing. My eldest boy’s just turned three, entering the first throes of childhood chattiness.

What I find especially interesting is that most of his conversation revolves around questioning.

He is thirsty for knowledge, yes — a never-ending stream of ‘but why?’s fall from his mouth, from the colour of the sky to the length of a stick.

But he’s also direct in asking for what he wants, or needs, or wonders about.

For my son, asking questions feels straightforward and natural. But as we get older, it seems to get harder: we become self-conscious, steeped in social norms and cultural values; we don’t want to be perceived as rude, needy or tactless.

Perhaps most crucially, we don’t like making ourselves vulnerable to rejection.

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And each question we ask creates an open space for someone else to fill. The answer may delight us; but it also might disappoint us, or make us feel like an idiot.

And so, we protect ourselves in advance by approaching questions in a circumspect way: we ummm and ahh and apologise and tiptoe around the issue, without clearly articulating what we want.

But we pay a price for that safety: it keeps us stuck.

Instead, imagine what could we achieve if we were able to go through life asking questions without fear?

Asking takes courage because we can’t control the answer. But we do control what, why, how, where, when and who we ask.

Like a diamond in the rough, effective questioning is a skill that can be uncovered, honed and polished.

The art of effective questioning: how to get the answers you need

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What, precisely, do you need to know?

On Jotform, our users ask 2.1 million questions per hour using our online forms. Yet one of the biggest reasons they still can’t find out what they want from their audiences is the lack of clarity in what they are asking for.

If you aren’t crystal clear about about what you’re asking, chances are the other person won’t be either.

Questions divide into three groups, depending on what motivates them.

We ask a question because we want or need something that can be:

  • a) factual information, an explanation, a clarification; 
  • b) an opinion, judgement or piece of advice; 
  • or c) help, permission for something, or a favour.

For most people, the third type of question is the toughest.

That’s because different types of questions have different underlying messages associated with them — and it’s these messages that can make us uncomfortable or resistant to asking.

  • If we ask for information, we implicitly acknowledge that the other person knows something that we don’t;
  • if we ask for someone’s view, we signal that we respect the other person’s opinion;
  • and if we ask for help, we show, well, that we need help.

These questions can make us feel vulnerable or feel like the weakest person in the room.

And yet, the opposite is true. As Brene Brown eloquently makes that point in her TED talk on vulnerability, strong people ask — even if they feel a little shaky about doing so.

Yes, asking for something is an admission of imperfection; but it’s precisely being able to accept — and relax with — our own imperfection that keeps us from getting stuck, and opens us up to change, learning and connecting with other (imperfect) people.

I’ve spent the last 12 years building a product that empowers people to ask questions to anyone. And here are the key things I have learned when it comes to asking questions to find out anything from anyone.

Let’s start with how to make asking hard questions as easy as possible:

1. Practise

Get comfortable with the possibility of rejection.

In his experiment, Jia Jiang proved this method leads to opportunities you might not even have considered.

The more often you do something, the easier it gets. That applies to asking, too. Ask your cab driver, your colleague, your postman; pretend you’re three years old again.

2. Prepare

If something matters, it’s worth preparing for.

Whether you’re asking for a raise or the reasons why your line manager decided not to adopt your proposed strategy, jot down some notes, drill it down, put those thoughts that are bouncing around in your head on paper.

This will help you zoom on the heart of the question, and articulate it more clearly so you can understand what, precisely, you’re asking for.

3. Give some thought to time and place

Our actions in life rely on external factors (location, weather, time of day) much more than most people realize.

You want the other person’s full attention; a query posed in a busy office, a bustling street or a crowded restaurant will be competing with other triggers and distractions.

Time pressure doesn’t help either — don’t squeeze in an important question at the last minute, when you’re in a rush or when attention and spirits are flagging.

4. Focus on one or two people only

Batting a question aimlessly around your network is bound to dilute its power, and runs the risk that nobody feels obliged to respond thoughtfully.

Asking one or two people who are well-equipped to answer your question is preferable to asking 20 who aren’t.

People love to feel needed, powerful and important. To know they’re the first/only person you thought of to help them is likely to set a little ego boost in motion.

Being one on a list of other respondents? Not so much.

5. Don’t beat around the bush

Then… You have to actually ASK. People email. They call. They drop hints. They take you for dinner. They create a group chat. They do everything but ask in the pursuit of avoidance.

So bite the bullet and be direct. Of course, it’s important to be friendly, courteous and respectful in your tone and the way you frame it. But don’t wrap it up in layers of qualifications. Own your question.

Maya Angelou famously summed this up as

Ask for what you want and be prepared to get it.

After asking

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1. Make room

Remember: by asking a question you create a space for the other person to fill.

This can be nervewracking, which is why it’s tempting to babble as soon as you’ve put your question out there.

Resist. Be generous in making space for the answer. Pause, stay quiet, and wait it out.

And when the other person has responded, wait some more. Often your interlocutor will have more information or thoughts, and bring them to the table — if you can be patient.

People like police and interrogators know the power of the pause and use silence to great effect. If you can get comfortable with silence, you’re able to create an environment in which valuable responses will bubble to the surface.

Once your conversant has launched into their response, it becomes even more crucial to stay quiet, even if there’s a natural pause. Interrupting will halt their train of thought and signal that you don’t value what they’re saying.

2. Follow up with a question

A follow-up question shows you’ve been listening carefully and are interested in the answer you’ve been given. Open-ended follow-up questions work best:

What makes you say that? Why do you think that?

Re-stating what the other person said to see if you have understood it properly will add solidity to the conversation:

If I understood well, you’re saying that…? If I understood well, you feel that …

3. Say thank you


4. Remember it’s a relationship

The relationship that arises when we ask a question isn’t static and one-way. We ask questions and we give answers.

That balance is important. Respond to questions in the way you hope other people will respond to yours.

Go out of your way when you can. The more you give out, the more that will come back to you. Invest yourself in others’ success and they will invest themselves in yours.

Asking online: it’s not what you ask, it’s how you ask it

Asking in person is one way of getting an answer. But more and more questions today are asked online, usually via email or survey.

Because you have to write the question down first, it’s easier to be methodical.

1. Surveys

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Forms are the most obvious way to get an answer from someone online.

But the process of form-filling can feel boring and monotonous, which, combined with the lures of the internet, can lead to inaccurate answers.

Questions in forms should be the most simple, light and bite-sized of them all.

Here’s how to write them.

1.1. Don’t use lead questions

Sometimes form owners’ opinions can end up in the phrasing of the question, encouraging respondents to answer in a certain way or assuming facts. For example, “How much will prices rise next year?”

Be wary of this by articulating your question in the most basic, non-biased way possible.

1.2. Ask one thing at a time

In surveys, the double-barrelled question often crops up. “Do you eat meat and fish?” could be a complicated question to answer for pescatarians. If in doubt, split the question in two.

Asking all your questions on one screen can also overwhelm your audience. Free online tools like Jotform Cards offers the flexibility to ask one thing at a time and the ability to customise online forms in engaging way.

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An example question built on Cards.

1.3. Try interval questions

Interval questions are a great way to get more specificity in your answers. These responses allow for much clearer analysis of your results.

The Likert scale is a popular way to do this, or, at Jotform Cards, we introduced the Emoji Slider: these animated faces make the process more fun instead of wading through endless options.

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Researchers use scales of 1–5 or 1–7 because they capture a high level of variation in answers, without causing information overload.

2. Email

Given people’s never-ending to-do lists plus the seductive call of social media, any email you send is competing in the attention economy.

Plus, over 50% of emails are sent and received on our phones, often on the go, meaning they’re likely to be checked at a glance: important items are flagged, the rest archived or deleted.

Your email needs to be attention-grabbing, concise and actionable. Here’s how you can get the answers you want:

2.1. Start with the question

Upon hearing the ping of their email, most people will simply glance at the two-line preview. What do you want them to see as they scroll? Your question, of course.

Putting it in the first couple of lines of the email will capture your reader’s attention and clarify what action needs to be taken.

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You can forward an email to yourself first to double-check what it looks like on mobile — if the content looks overwhelming, people will swipe it away before bothering to open it.

2.2. Propose a solution

Email isn’t the place for a debate that goes back-and-forth. It’s in everyone’s best interest for the conclusion to be arrived at as quickly as possible.

Busy people don’t want to have to decipher meaning or write lengthy responses — they want to answer yes or no.

Pre-empting an answer or solution to the question that prompts the email is a way of moving things forward.

3. Give a deadline

Jocelyn K. Glei claims that emails with a clear deadline are more effective:

It may surprise you to learn that busy people love deadlines because they help prioritize exactly when things need to get done. Emails that have no timetable are more likely to get ignored.

Does the question in your email need a response in an hour, a day, a week?

Lay it out.

4. Keep it concise

Read and re-read the email with a ruthless editor’s eye. Remove any unnecessary information, and then some.

It can be helpful to drill information down to bullet points to make the content more digestible.

Final thoughts

As author Nora Roberts once said:

If you don’t go after what you want, you’ll never have it.

If you don’t ask, the answer’s always no.

If you don’t step forward, you’re always in the same place.

Questions are part of the fabric of life. They are dynamic, they challenge us, and they can bring out the best in us.

In the words of Tony Robbins, quality questions create a quality life.

What we ask matters, as does how we ask it. It pays to slow down and reflect on what and how you ask. At worst, it will be grist for the mill; at best, it will open doors you didn’t even know existed.

Now if you’ll excuse me, I have a very inquisitive little boy to attend to — I need to explain to him why back seat is the right one for a 4 year old.

Thanks for reading.

Aytekin Tank is the founder and CEO of Jotform and the bestselling author of Automate Your Busywork. A developer by trade but a storyteller by heart, he writes about his journey as an entrepreneur and shares advice for other startups. He loves to hear from Jotform users. You can reach Aytekin from his official website

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