10 Practical Tips to Better Ask Questions [to Understand]

“Hey John, the [poor] way the new division is collaborating with us on pre-sales is actually worsening our conversion rate, right?”. If the aim was to genuinely better understand something, such a question contains at least three mistakes: have you spotted any one of them? If you think you have, leave a comment with “yes”, if you haven’t, leave a comment with “no”. In this article, I’m going to share 10 practical tips to better ask questions, when your purpose is to better understand.

In a comment to a previous post, Nicoletta asked me: “What about a follow-up video on business interviews for process mapping made easy?”. So here I am. Although this is not focused specifically on process mapping, I believe it is perfectly suitable for that kind of task.

Why am I specifying the purpose of “better understanding”? Because, if you had a different one, such as, for example, winning an argument, my tips about the way you ask questions would be completely different. Whether you’re analysing someone’s business model, observing an existing operational process, or listening to the account of a past event, you’re in a context of better understanding.

If you haven’t already, by the end of this video, you will also be able to tell which mistakes can be associated with the initial question. And, if you want to get access to more content in the future, make sure you subscribe right now!

How to Better Ask Questions

Before we start, a brief warning: the whole topic of asking questions is huge, involving disciplines ranging from linguistics to neuroscience through cognitive psychology. What we are covering here are a few safe-to-use, practical tips.

There’s plenty of attention you can put to improve the effectiveness of your questions, before, during, and after you actually ask them. Here are my tips.

Tip n. 1: Have a Framework in Mind

Depending on the object of your inquiry, whether it’s about business models, strategic decision making, business process mapping, etc., having a framework in mind will be of great help. How? In at least in two ways:

  1. By providing an ordered place to store information that usually comes in random order;
  2. By making relationships between parts more easily evident.

I won’t go deeper now into the distinction between categorization and sense-making frameworks. Framework as a topic would deserve a separate discussion.

I’ll limit myself to a few examples:

  • Alexander Osterwalder’s Value Proposition Canvas can help you better understand a business value proposition.
  • Prof. Dave Snowden’s Cynefin is a sense-making framework to help you determine what approach you should apply based on the level of disorder and complexity, in a certain decision scenario.
  • In a talk about processes, you should be able to quickly discern what refers to an actor, a task, a decision point, a tool, a sequence, an information exchange, etc..

I’ll provide links to some useful frameworks in the credits and sources section below.

Now, beware: frameworks are a means to achieve better understanding, not an end in themselves. Leave some space for information that doesn’t fit your framework. Don’t get framed by your framework: allow some space for the possibility that you’ve chosen the wrong one!

Tip n. 2: Plan for Appropriate Time

You’ve just finished your scheduled meeting time and the answers to your doubts are still all there uncovered. What a shame!

No shortcut here: either you’re able to reserve a sufficient time to clarify all doubts or you’ll be left with them. If the person you need to interview is very rigid on her schedule, you can try the following three tactics:

  1. Anticipate to your counterpart the possibility of a later follow-up;
  2. Find alternative sources;
  3. Narrow your scope, reach an intermediate goal with that, and use this to get credit for a second round.

Tip n. 3: Culture Matters

Depending on cultural factors, the quality of the answers you get can be heavily affected:

  • by the content of your questions,
  • and by the way you ask them.

For example, making funny jokes when meeting a German director for the first time or asking the age of a female Colombian team-mate may not be that smart. On the other side, doing the same two things could be less critical in Italy and China, respectively. The rules of thumb here are:

  • Country-based cultural categorizations are at best rough stereotypes;
  • in case you are in doubt, abstain.

Whenever the cultural context is likely to be different from your usual one, be careful and do your homework before you start. If you don’t understand why I’m suggesting this, I promise you will. Or else you’ll become one of those culturally ineffective persons who keep on saying phrases like: “the Indians are…”, “the French are…”, “the Mexican are…”.

Tip n. 4: Start with Easy Questions

Conversations are smoother when people are at ease. One good way to ensure this is to start with easy questions. Make the other person confident about her ability to answer, before you move to more complex topics. In the end, this also contributes to building trust: a scarce resource and the most powerful facilitator of all.

For example, if you’re analyzing a process that you know in advance has some issues, start by asking how it works when everything goes well. After the baseline is set, go deeper into the critical points.

Small talk can also be used, with care. Depending on cultural factors – see the previous tip – small talk could be perceived as a pleasant icebreaker, or as a waste of time. If you don’t know and you use it, it’s generally safer to keep it short.

Tip n. 5: Look for a Story, Rather than Judgement

Let the narrative flow without interruption, filter out judgements and opinions, and look for behaviors.

Judgements and opinions usually carry purposes with them. Paying attention to them might be useful for understanding people’s intentions, values and individual criteria, rather than for understanding facts.

Tip n. 6: Never Suggest the Answer

People sometimes tend to tell you what you want to hear, rather than their plain truth. This does not necessarily imply dishonesty. Sometimes it is just most people have a strong need to please other people. That’s why you should never include an answer in the formulation of your question.

Tip n. 7: Ask About them, Not About You

Help people feel that they are talking about themselves, rather than about something that is useful to you. Show genuine interest in their lives, problems, challenges.

You may connect with them, by comparing theirs with your personal experience. But never let your ego prevail over their need to tell you their story.

Tip n. 8: Mind the Bias

As human beings, our judgement is biased. And if you think that this applies to others, but not to you, this is in itself a proof of what I’m saying. Sorry for revealing this to you.

One for all, and one of the most common among our biases is the so called “confirmation bias”. According to Wikipedia, it occurs when we “search for, interpret, favor, and recall information in a way that confirms one’s preexisting beliefs or hypotheses. It is a type of cognitive bias and a systematic error of inductive reasoning.”.

Being aware of your biases is no guarantee that you will not suffer from them. But self-training yourself in paying attention to evidence that contradicts your established beliefs is an extremely useful practice.

Tip n. 9: Listen until the End of the Answer

Why do I generally hate having other people with me when asking questions? Because, too many times my efforts of grasping the truth have been frustrated by other people intervening and interrupting at the wrong moment.

Some people feel uncomfortable with silence. Some feel uncomfortable with keeping silent when someone else is talking. If you’re one of these, start training to listen an answer until it’s finished. If you’re really committed to understand, let people complete their answer before talking. Treat silence as one of the most powerful tools in your hands.

In particular, never ever try to complete someone else’s answer. Chances are that the other person is thinking of something even more important. Interrupting this flow of consciousness might compromise your only opportunity to know the truth. Even worse, your attempt to ease the completion might compromise the authenticity of the answer.

Tip n.10: Take Notes… and Review Them Soon After

Take notes during the interview. Whenever appropriate, ask permission to do so.

Some prefer taking notes with some kind of keyboard and screen. I prefer paper: I find it less intimidating, faster, and more flexible. But this might be due to my limited typing skills.

Whatever the method for taking notes, the longer you wait before reviewing them, the larger is the amount of information that you’re losing. So, make sure to allow some time in your schedule to review your notes after the interview.

The Importance of Being Trained

Interviewing people is like language proficiency: the more you practice it the better the outcome. Good news is that you can train in almost any place.

Practice by asking questions to your friends, family members, taxi drivers, colleagues, waiters, train commuters, barbers.

Start with simple questions, like “How long have you been doing your job?”, or “What is your favorite Vietnamese restaurant?” Then gradually move to more difficult ones. At a later stage, you’ll be able to ask a taxi driver in Lisbon what he thinks about Uber, or a first-generation Algerian immigrant in Paris about Zinedine Zidane’s behavior in the football world cup final match in 2006. Disclaimer: these are mere examples, you ask questions at your exclusive risk and I take no responsibility for their consequences!

Initial Question Mistakes

Now, getting back to the initial question: “Hey John, the way the new division is collaborating with us on pre-sales is actually worsening our conversion rate, right?”.

Let’s review the tips:

  1. Have a framework in mind
  2. Plan for Appropriate Time
  3. Culture Matters
  4. Start with Easy Questions
  5. Look for a Story, Rather than Judgement
  6. Never Suggest the Answer
  7. Ask About them, Not About You
  8. Mind the Bias
  9. Listen until the End of the Answer
  10. Take Notes… and Review Them Soon After

Have you spotted at least three mistakes? If you have, write the corresponding numbers in the comments below.

Conclusions on How to Ask Questions

When someone is answering your questions, it is safer to expect them to be less concerned about the accuracy and the completeness of their answer than about your judgement or about possible consequences. Being aware of this fact, together with some practical tips, can help you reach better results, when you’re trying to understand something through questions.


Subscribing to my YouTube channel is just one or two clicks away, if you haven’t done it, yet. By doing so, you’ll make sure you won’t miss the next episode.

I’ve told you my tips. Now, tell me your favorite one for asking better questions. Leave it in the comments below! I will add the best ones to the list in the post on my website, lucaorlassino.com.

Credits & Sources:

Categories and Tags

Topic: Frameworks & Tools

Language: English

Tags: business process, interview skills, Business Model Canvas, Value Proposition Canvas, questions

Posted in English, Frameworks and Tools and tagged , , , , , , , , , , .

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