
A common behaviour I observe in my clients is the tendency to fall down metaphorical rabbit holes when they talk, which often leads to difficult conversations.
They start talking without a clear direction, simply wanting to make a point. As they speak, thoughts and emotions get triggered causing the conversation to divert into multiple tangents. These side-tracks create confusion and frustration, resulting in an unproductive and difficult conversation.
Take Jenna* and Rob* as an example. Jenna might say, “I want to discuss X” focusing on her frustration with Rob about this issue. But as she speaks, she mentions Y to prove her point, shifting the conversation off-course. Rob then feels defensive and so brings up Z to prove his point. Before they know it, they’re arguing about Z – far removed from the original topic, X. Both feel lost, frustrated and confused.
So, what’s the alternative to this kind of difficult conversation?
Prepare for Difficult Conversations to Make Them Easier
One of the keys to making difficult conversations easier lies in preparation.
The first step is to notice your internal dialogue and regulate your emotions before speaking.
Once you’ve regulated your emotions, follow these steps:
CLARIFY YOUR INTENTION
This step involves four key actions:
- Determine the outcome you desire
Ask yourself “What would I like to happen as a result of this conversation?” Then continue asking, “Then what?”
For example, you might think: “I want him to stop walking out during our conversations”
then ask “Then what?
Your answer might be, “We’d talk more often”
Then what?… and so on…
And finally, “I’d feel more connected to him”
So your true intention might be to feel more connected as a result of the conversation. Digging deeper like this can help you uncover your real needs and avoid getting stuck in difficult communication patterns.
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2. Focus on your deeper needs
Often, what we want from a conversation revolves around feeling:
- connected
- heard or understood
- valued or loved
Focusing on these underlying needs can shift your mindset into a more positive state, making the conversation feel less difficult and giving both of you a clearer, shared and more compelling goal.
- Imagine the kind of conversation you want
Consider what kind of conversation you want to have and imagine it unfolding the way you would like. What do you want it to look, feel and sound like?
- Do you want it to be calm and respectful? If so, how can YOU contribute to that?
- Do you want to feel heard? If so, are you ready to listen?
- How would you like feelings and emotions to be expressed. Will you express them that way?
Starting a difficult conversation with a clear sense of how you want it to go, makes it easier. Your intention acts as the route for the journey, helping you avoid the dead-ends that lead to difficult conversations.
- Consider the needs of the relationship
Often the topic at hand isn’t the most important thing in the conversation. What matters more is how the interaction will affect your relationship. Every conversation, especially a difficult one, has the potential to either nurture or harm the relationship.
Imagine the relationship is a third person in the conversation. What would it say if it could ask for what it needed from the conversation? This perspective can help you avoid power struggles and focus on the bigger picture – maintaining and strengthening the relationship rather than winning an argument.
For instance, you may want your partner to come home earlier from the gym to help with the children, while your partner may wish for more personal space.
However, the relationship might need both of you to listen to each other’s perspectives, respect each other’s preferences and find a compromise.
By considering the needs of the relationship, you create a foundation for a more constructive dialogue rather than a difficult conversation.
SHARE YOUR INTENTION BEFORE YOU BEGIN
Communicating your intention openly before you start the conversation can make a big difference. Let the other person know how you’ve prepared and what you hope to achieve. This will give them time to reflect and prepare as well, reducing the chances of them feeling ambushed or defensive.
Also, ask if they have an intention for the conversation. This prevents you from deciding unilaterally how the conversation will go and encourages a more collaborative approach.
AGREE A TIME AND A PLACE
Don’t assume that just because you’re ready to talk, the other person is too.
Agree on a convenient time and place when you can both focus on the conversation. Avoid initiating important discussions when either of you is tired, distracted or in a rush.
I’m not advocating the end of spontaneous conversations, but when difficult emotions are running high or the stakes are significant, planning ahead is invaluable.
Thoughtful preparation can significantly reduce the chances of another difficult conversation experience.
Few of us would start a journey without knowing our destination, planning the route or ensuring our vehicle is ready. Conversations, especially those that could become difficult, are no different.
By following these steps, you’ll improve your chances of having a constructive dialogue, not only for your own benefit but for the well-being of both of you and the relationship itself. Ultimately, this approach will lead to fewer difficult conversations and more win/win/win outcomes for both of you and the relationship.
*Jenna and Rob are the fictitious names used to represent typical client scenarios.
For more about this approach (especially if you prefer to listen rather than read) check out my video blog Improve Communication before you speak

