Having a philosophical conversation that is light and playful yet profound

Having a philosophical conversation that is light and playful yet profound

By Kristof Van Rossem

Kristof Van Rossem (°1969) holds a Master degree in Philosophy and in Sciences of Religion. For more than 20 years, he has been an independent trainer working with dialogue and reflection in various organisations. His specialities are the “art of questioning” and variations of “Socratic dialogue”. Kristof is teaching Business Ethics at Odisee University College of Brussels and he is a teacher trainer in the department of philosophy of the University of Leuven (KUL).  

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Reflection begins where the expression of personal opinion is disrupted. After all, anyone who only repeats in a conversation what they have thought of something for a long time does not think. Philosophizing together teaches you to think more sharply, to pay attention to the interests of others and to tell your own story with more conviction. It takes you into a free world full of new thoughts and feelings.

As a student of philosophy, I was intrigued by how I could use philosophy to improve people’s thinking in daily life and work. I became an independent trainer and I have been working with all kinds of people, from detainees to top managers. But how to have a constructive philosophical conversation with others? Which philosophical skills do you need for that? As I couldn’t find any decent book describing how you keep dialogues on an elevated philosophical level, I decided to write one myself.

In “The philosophical conversation. The basics” you will find the most important philosophical skills for having, or leading, a philosophical conversation that is profound and yet light and playful. Here, I highlight two basic skills that are needed. First, you need to listen properly and second, you need to ask the right questions.

Stop thinking, start listening 

The art of asking questions is the result of the art of listening. A well formulated question is the result of careful listening to the interlocutor. There are mainly two ways of listening, a ‘full’ way and an ‘empty’ way. In a philosophical conversation, you need to listen with an ‘empty’ mind. 

The full way of listening is called ‘full’ because your own thinking is fully present. In listening to your interlocutor, you think like: ‘I recognise that’ or ‘I can apply this to my own situation’. You check whether what the other says fits your standards or your judgement. In other words, this type of listening is selective, judgmental, coloured by one’s own thinking. 

This way of listening is not wrong in itself. The listening is for instance done by experts and is inspired by the need for solutions. It is common in situations where action needs to be taken quickly: at the doctor’s, as a plumber, as a researcher, when collecting data. In a philosophical conversation, this way of listening is not recommended. After all, there is no problem to be solved of which you would know more than the other.  

The ‘empty’ way of listening is different. This way of listening starts from an attitude of ‘availability’ or ‘presence’. This attitude implies a complete openness to everything that is happening, not only in the conversation but also in the environment: the energy, the aesthetics of the environment, the emotions, the details in the speaker’s body language and tone. It implies an awareness of both what is happening inside of you as well as what is happening in the other. 

Only in your silence can the other reveal himself as another person and develop his ideas. The silence implies the acceptance of every sentence the other person will produce, and also the realisation that it will always be different from what you think. This attitude stems from a familiarity with silence and that silence is fundamental to the process. In being silent, you give space and time to your interlocutor to express what he wants.

The basic questioning skills

Questioning seems simple but it isn’t. It requires an empty head and a full focus on the other. You can compare it with archery. Your question is like an arrow. It comes out smooth and simple, straight and in the direction you want. You don’t get a second chance. Archery as well starts with the acceptation of what is there. And then you need to practise. These are the most important tips:

1. Formulate one question at a time

It’s Sunday morning. Mum asks her sixteen year-old daughter: ‘So, how was the party yesterday? Were there a lot of people? Did you have a good time? Did you see Sandy?’ The daughter is silent, scratches her head and goes on Instagramming. What do you expect? If you ask many questions at once, you are actually busy with your own thinking. You are not paying attention to the other person! One question at a time allows you to pay more attention to the other person’s reaction.

2. Formulate your question as simply as possible

When you ask a question, your intention is that the other thinks about the answer and not about the question. If your question is too difficult or too vaguely formulated, the other will not understand you. Try to formulate your question as simple as possible. A philosophical conversation is difficult enough! So, instead of, ‘Would it be possible to test this out empirically?’, just ask ‘Can you give an example of this?’.

3. Formulate your question as briefly as possible

A characteristic of a well formulated question is that the other remembers the question. A question like ‘What is your responsibility as a parent given the fact that you are in charge of two adolescents who are struggling to find their own way in life?’ is difficult to remember by the interlocutor. So it is better to ask, ‘What is your responsibility as a parent of two adolescents?’. A good maximum is about ten words.

4. Ask questions like a chameleon

Do not introduce new concepts in your question. Just like a chameleon sitting on a tree takes on the colours of the tree and becomes invisible to enemies, a good questioner uses the other’s words as much as possible. In this way, the other can recognise himself in the question and will be more motivated to answer it. If you copy the words, it is a sign that you have listened well. Besides this psychological advantage, there is also a cognitive advantage: your participant can concentrate better. He will not be distracted by new concepts. 

An example:

The other: ‘I am afraid to stand up for myself’.

Non-chameleon question: What is the cause of this fear? 

Chameleon question: Why are you afraid?

5. Ask open questions

Often ‘open questions’ are understood as questions to which you can answer anything whereas with closed questions, you are restricted to a limited amount of possibilities like yes, no, maybe, I don’t know. This is so in a questionnaire. It’s a more formal distinction. It doesn’t talk about the character of a question.

I see therefore an open question as a question where the other person feels free to answer anything. A closed question is a question where the other person feels pushed in a certain direction. An open question is for instance: ‘What do you think of this training?’ The closed variant is: ‘The training is boring, isn’t it?’ A question like: ‘Is there life after death?’ would ‘grammatically’ be considered as a closed one because there are a limited amount of possible answers like ‘yes’, ‘no’ or ‘maybe’. I see it as an open one because you are free to answer whatever you want. The conversation will then go on on the basis of the arguments.

A closed question can also be called a ‘suggestive’ or ‘rhetorical’ question. Here, ‘Don’t you agree that we all go to heaven after death?’ is a closed question. These questions do have advantages. They enable you to win people over to your side. After such a rhetorical question ‘Right?’ you are no longer alone. You are supported. An open question is much more ‘lonely’. The chance is about fifty per cent that you will have people who will answer something you like. But they will answer what they think and not what you want them to think. 

6. Provide emotional comfort

Finally, there must be freedom for the other to answer your question. He will not feel this freedom if you dominate the other or make him afraid. You make the other feel at ease by having an open, inviting attitude. The other needs to feel that he is a person who is accepted. The more you can enable this emotional support, the further you can take your questioning and the more you will be able to make more far-reaching interventions in what he says and thinks.

The book “The philosophical conversation. The basics” shows you how to get started with the most important philosophical skills. A variety of exercises helps you think more precisely and shows how to communicate that to others. This book is your guideline to uplift the quality of reflective conversations.


To order the book, see https://www.amazon.com/Philosophical-Conversation-Kristof-Van-Rossem/dp/1803412712/ref=sr_1_5?crid=3PFBATPCSNZSQ&keywords=philosophical+conversations&qid=1707765896&sprefix=philosophical+conversations%2Caps%2C308&sr=8-5

Or www.thephilosophicalconversation.com