Summary: Do you find it hard to start a conversation with someone or to continue with a good conversation during an event? This article is about asking good questions to create a connection, show empathy and to help people reflect. It contains 35 good questions you can ask others (or answer for yourself).
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I enjoy talking to people and I am always curious how people live their life, what stories they have, where they came from, what their challenges are and where they’re headed.
Why ask good questions
The art of asking good questions helps you connect, show empathy and the be authentic. Chances are that people will be surprised when they hear a good question. Most people I meet, love to talk about their own experiences, their goals and challenges.
It’s good to ask questions during a conversation. Especially, if you’re the type that likes to talk a lot.
But perhaps you’re just too afraid to start a conversation. The “Hi, what do you do?” or “Great weather for this time of year, huh?” will not really get things going.
Avoid asking Closed-ended Questions
When I ask you if you originate from a certain city or country, you’d probably answer ‘yes’ or ‘no’. Also if I would ask you how you’re doing, you’d probably answer ‘good’ or ‘not so good’. These are closed questions and will unlikely invite to further conversation.
Sometimes it’s necessary to ask closed questions. Especially, if you need an answer fast (‘Who wrote this report?’ or ‘Did you call the client?’). It’s about getting the facts.
If you want to ask good questions, avoid the closed-ended questions to obtain facts.
Ask Open-ended Questions
Open-ended questions start with ‘How’, ‘What’ or ‘Why’. These questions invite others to give meaningful, thoughtful and deep answers. People tend to open up because you’re showing authentic interest in what they have to say. The questions invite others to share their feelings, thoughts, opinions or ideas about something.
Sometimes questions are not really questions but a sentence will invite others to respond to you. Examples are: ‘Tell me about…’, ‘Describe me…’ or ‘I don’t understand, please explain it to me.’
During my coaching- and training sessions, I ask a lot of questions. Goals can be to motivate people to make them reflect, to become aware of something, to make a connection or to create trust. Some work well and other less. This depends on the situation and the person. If people don’t feel safe, they won’t likely answer questions. Especially those relating to feelings or opinions.
Be aware of boundaries. When people don’t want to talk about things, they will let you know. They will nod, hum or look away. Other signs are that they move away from you, that they cross their arms or simply fall silent. In that case, the best thing you can do is to verify if they feel uncomfortable talking to you, to apologize if necessary and to thank them for their time.
And then there are those questions which are not really appropriate to ask in certain settings. I would not ask about the results of a sports match at a shareholders’ meeting (but I would do this when I meet contractors). I try to adapt to setting, the people present at a meeting and what is needed at that moment.
My favorite questions
I do listen to a lot of podcasts and I read a lot of books. From those resources (and sometimes TV or radio), I started to write down my favorite questions.
My intention with these questions is to get to know people, make a real connection, to show empathy, help people to reflect and to give others the opportunity to share valuable stories and tips.
Find below 35 of my favorite questions I like to ask people I meet, I work with or guests on my Podcast. Most of questions are from books, courses, other podcasters or people I meet. I am sure there will be one that you would like to ask or be asked!
- What is your greatest challenge now?
- What (or who) are you most grateful for? Why?
- What have you learned new this year, this quarter?
- Have you experienced something exiting lately, what was it?
- Who do you look up to? Who are your mentors? Who inspires you, why? What have you learned from them?
- What makes you different? Who trained or influenced you?
- What are your favorite books? Why and what have you learned from them?
- What new habit has greatly improved your life?
- What is a silly habit you have?
- What makes you happier in life? What excites you?
- What were the steps that got you to…?
- What do you need to let go of to take the next step?
- What do you do when you‘re unfocused?
- How did that make you feel?
- What’s happening now?
- What do you want?
- What do you think the most of during the day?
- Could you share something about yourself that is not known to many people?
- What do you believe in that other people think is crazy?
- What are you really good at? What are you able to give?
- When was the last time you over delivered on something? What was it and why did you work so hard?
- When was the last time you were in a state of flow and you totally lost track of time? What where you doing?
- What are you proud of?
- Tell me about one of the mistakes you’ve made and what you learned from it.
- Why do you do what you do?
- What is your vision now?
- What would you do, if you knew you could not fail?
- What are you more afraid of? Being relevant or irrelevant? Why?
- What do you love helping people with? How do you most commonly help people?
- Out of all your work roles, what would you gladly do for free?
- What course would you teach and to whom?
- What do people thank you for?
- What do you want to be remembered for-what do you want to have put in the world?
- What question would you like people to ask you more?
- Is there anything I haven’t asked you that you want to say?
When you’ve received meaningful and touching answers to your questions, please acknowledge the other person and thank them for being vulnerable and being open. I am sure that they will appreciate this and that a deeper bond of trust and acceptance between the two of you has been created.
And then there are also some good questions to ask during a job interview.
Do you know any good questions to ask? Let me know in the comment box below. I, and other readers of this article look forward reading from you!
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