Difficult Conversations made easier

Difficult Conversations Made Easier

Juliette Smith Advice, Communication, Conflict, Couples Leave a Comment

A behaviour I frequently observe in my clients’ is a tendency to go down metaphorical rabbit holes when they talk, resulting in difficult conversations.

When they begin talking they don’t know where they’re heading, often just wanting to make a point.  Thoughts and emotions triggered during the ensuing exchange then side-track the conversation into countless tunnels, with different themes.  Ultimately they feel lost and unsatisfied.

For example, Jenna* might say to her partner Rob*, “I want to discuss X”.  All she’s aware of is her anger with Rob about X and she wants to tell him about it.  Whilst talking, she feels the need to prove a point by mentioning Y and unwittingly moves the conversation into tunnel Y.  Here, Rob feels defensive and so reminds Jenna of Z. Before they know it, they are arguing about Z – miles away from X – and now frustrated and confused.

So, what’s the alternative?

Start difficult conversations by preparing – then they won’t be so difficult 

Noticing our own internal dialogue before difficult conversations and regulating our emotions are the first steps towards preparation.  My article “Improve communication, before you speak” will guide you in the specifics.

Your next steps are:


This has three parts:

  1. Ask yourself what you would like the outcome to be

In response to the answer you give, ask yourself, “Then what?”

For instance

“I want him to stop walking out on our conversations”, then what?

“We’d talk more often”, then what?

“I’d feel more connected to him”

So perhaps your intention is actually to feel more connected as a result of the conversation. Asking yourself more questions helps you uncover your real intention.

Generally, what we really want is something akin to feeling

  • connected
  • heard or understood
  • valued or loved

Think deeply about what you REALLY want from your conversations.  Focussing on the deeper desire is likely to put you into a more positive state before you start and give you both a clearer and more compelling destination.

  1. Consider what kind of conversation you want

What do you want it to look, feel and sound like?  Imagine the conversation going as you would like:

  • Do you want it to be calm and respectful? If so, what can YOU do to make sure that happens?
  • Do you want to be heard? If so, are you going to listen?
  • How would you like feelings to be expressed. Will you express them in that way?

Starting a conversation clear about how you would like it to be and how you will contribute to that experience is like deciding the route you’re going to take to the destination you want to reach.  Rarely would you start a journey without considering the route.

  1. Think about what the relationship needs from the conversation

It’s likely the issue you want to discuss is not the biggest thing at stake.  Any conversation is likely to have an impact on the relationship which should be taken into consideration, especially if it needs nurturing or even saving.

Imagine the relationship is a third person in the conversation.  The two of you will have opinions but what would the relationship say, if it could ask for what it wanted from the conversation?

For instance, you might want the outcome to be your partner coming home earlier from the gym to help with the children.  Your partner may want you to stop nagging and give him some space.

The relationship, however, may well need you both to listen to each other, acknowledge each other’s preferences and find a way they can be respected.

Looking at the conversation from this third perspective helps you step back from anything that might feel like a power struggle and see there is something bigger at stake.

It’s like ensuring your transportation is checked and cared for before you start your journey.


Letting the other person know your thoughts about the conversation in the context of the questions above is likely to increase their desire to participate.

If they have some time to consider the conversation (in the same way you have) they too can feel prepared (rather than forced or ambushed) which will add to the foundations of a successful interaction.

Ask if they have an intention too.  Preparing doesn’t mean unilaterally deciding on how the conversation will go!


Don’t assume because you want to talk at a particular moment, the other person does (or should) too.

Once you have taken the above steps, agreeing a convenient time and place should feel easier.

It’s not wise to start a conversation when you are tired or need to be somewhere so, arrange it for when it can have the time and space it needs.


I’m not advocating the end of spontaneous interactions, but when emotions are present or the stakes are high, thinking about a conversation ahead of time is invaluable.

Few of us start a journey without some idea of the destination, the route we will take or ensuring the mode of transport is safe and well looked after.  A conversation is no different.

Following the above steps will give you a far greater chance of cultivating a positive dialogue, not just for your own benefit but for the benefit of both of you and the relationship itself and thus increase the likelihood of a win/win/win outcome and reduce the number of your difficult conversations.

*Jenna and Rob are the fictitious names I use to represent a composite of my clients. Their challenges are typical of those my clients present

Coming soon…The conversation itself – How to give it the best chance of being successful and enjoyable.


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