The art of choosing the right conversation

Often, we engage in conversations intuitively. But by reflecting on our approach and our intentions, we can take them much further.

Steffan Surdek
September 29, 2020
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In one-on-one sessions, I often coach clients around conversations they need to have. These may be conversations with employees or with colleagues but there is a common theme though. Our chats end up coming down to one essential question: What conversation do you want to have?

This article explores the notion of choosing the conversation you want to have. When does this apply and how can you apply this notion?

Why choose a conversation?

There are many different ways you can approach any given conversation. Making a choice allows you to get clarity on how you want to approach it and what you will talk about. It also allows you to get clarity on the outcome you are expecting from it. This clarity will guide your posture and how you show up in the conversation.

Here are some conversations for an employee who behaves unproductively in a meeting:

  • You are curious to know what happened because it is the first time you notice this behaviour.
  • You want to talk about it because it's a pattern that happens in every team meeting. You want to create awareness and come up with an action plan.
  • You want to follow up because you discussed this before and you are not seeing any change.
  • You want this behaviour to stop because it is unacceptable and does not reflect the team values.

I put them in a bit of an escalation here, but it is not always necessary to do that. These are possibilities for conversations but each may have a different desired outcome. The idea is to choose the conversation that matches your intention.

Different conversations create different results

The conversation you choose will have a direct impact on how you act during the exchange. Let's take a closer look at some of the examples from the last section.

Example 1: You are curious to know what happened because it is the first time you notice this behaviour.

In this conversation, you will probably be a bit more curious. You will set up the discussion in a different way as well. "John, I noticed you were not quite yourself today in the team meeting. Is anything going on for you right now? What happened today?"

It's hard to convey the tone but you can see this is more about curiosity. There is no need for change or action at this point. You may get there, but it is not the intention of the discussion. This will create a very open conversation. It may feel a bit odd or tense at the start if the other person is not quite ready to open up.

Example 2: You want to follow up because you discussed this before and you are not seeing any change.

In this conversation, you will probably be more forceful. Your tone, level of understanding and patience may be different too.

This conversation will create a bit more tension. You will want to walk out with a clear action plan, or clear consequences laid out on the table. If we compare both conversations though, each will create different behaviours and outcomes.

How to choose a conversation?

Now that you know you can choose, how can you identify which one you want to have? Part of it starts with what you want to achieve in the end. When you have a clearer idea of ​​the result you want, you can filter out the possibilities or create new ones.

The other way to find the right conversation is to identify your unmet needs. Why do you feel the need to have this discussion? Getting clarity on this can guide you to find the right conversation.

Getting clarity on the request you want to make to the other person can also help. The ultimate target is to get clarity on the unmet needs AND have a clear request for the other person.

There are times you may be clear on the unmet need and want to explore the possibilities with the other person. This is ok but be clear with the person you are talking to if you have preferences. If you do not, it can lead to a conclusion you will reluctantly accept that does not meet your initial need.

The best measure is the level of satisfaction you expect to get out of the conversation you choose. If you think you will come away from it with baggage or resentment, it is probably not the right one.


The notion of choosing a conversation is a powerful thing. Choosing the right one can create powerful change you may not have thought possible.

It requires you to see conversations in a more abstract way than we usually do. It is also a skill that you can develop with practice. To do this, take a moment a few times a day to look at conversations you had during the day. On a piece of paper, jot down the other conversations you could have had instead.

You can then look at these different conversations and practice what they could look like in your head. How would you bring it up? How would you act in this conversation? What would be the key things you want to bring up in this discussion?

Explore the possibilities and start practicing having these new conversations in your life!

Which conversations can you have differently in your life? What powerful results could you create by choosing different conversations with your employees and colleagues?