How to have great (and meaningful) conversations.

2. Practice good conversations

While it is completely possible to have incredible conversations by accident, it can also definitely be induced by a little effort. If you have never before had a great meaningful conversation, you wouldn’t know one when you see one. If you have never shared a deep conversation, when you have one, chances are, you might get inundated. Or let me put it this way — if you have had one of those before, you will be able to respond much better when you have one in the future.

3. Prepare

As a student of theatre, I am professionally trained to improvise. And thus for the longest time, I was way too comfortable in my ability to “wing it”. I mean, I know my crap, I know how to use it and how to turn things around, what can go wrong, right?

4. Ask good questions

  • Don’t ask what you could find on Google. Or, as a friend once told me, don’t ask because you are too lazy to find those answers on your own.
  • Open-ended questions. Always. Not just in how they are framed, but mostly just making sure that the other person always has the space to explain, that this doesn’t feel like either a a job interview or a trial. When in doubt, a “why do you think” and “what do you mean by that” are the safest options.
  • Don’t ask if you are not willing to really hear the answers or if you aren’t ready to hear with an open-mind.
  • When I go with a particular end in mind, I always let the other person know that in advance or at least in the beginning of the conversation, and give context to make sure they know why I am asking. This rule is also helpful when someone else has initiated a conversation with me — it helps the conversation feel like one rather than an interrogation, because the motive is consensual and no one has anything to prove.

5. Listen. Pay attention. Be present.

Probably the most overstated advice when it comes to conversations. With good reason.

6. Invite them into sense-making

This is the one you don’t get very often (although the same sentiment is often brought up differently in many places), but in my experience, it is mostly this that gets people to open up. Like I have said before, vulnerability is different for different people — not just in how vulnerable they are willing to be, but also what vulnerability looks like for them. Some people would be perfectly okay sharing a personal anecdote, but won’t tell you how they feel, some would never tell you what they really think of something, whereas some others might tell you the lessons they have learnt from their experiences, but never share the experiences. Having put a lot of thought and work into what makes me vulnerable, I know what my style is and what my boundaries are, and that helps me quickly also know what the other’s style is and boundaries are, and that often that makes it really easy for me to navigate this, particularly because the topics I speak to people about are deeply personal. But even generally, being gentle enough for people to draw and define their boundaries, and allowing them the time and space to build the trust to open us is in my opinion, non-negotiable.

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Jayati Doshi

Jayati Doshi

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Story-curator. Facilitator. Wondering about collective sensemaking, stories, love, belonging & questions that have no complete answers. https://jayatidoshi.com/