How to Make Difficult Conversations Easy

I have had several “difficult” conversations and I haven’t always got it right. One of those was a particularly tricky conversation with a previous manager. We were very different personalities. I needed freedom to work and grow and he needed to control and direct most of my tasks. It was a clash of needs that we didn’t identify, we didn’t talk about nor did we particularly care. Our relationship deteriorated to the point where neither of us could stand the sight of each other and one of us had to go.

This blog post is about how to navigate conversations that fit into those kinds of dynamics. If you want to make difficult conversations easy, you need to understand what makes them productive and most importantly, how you can prepare for them. If you follow this advice, you will be controlled less by your emotions and all of your relationships will improve with better communication.

The framework for all difficult conversations

Any productive conversation requires two things :

  • One person expresses themselves;
  • The other person listens.

Think of a time when you felt you didn’t have permission or space to express something important to you like a need, an emotion or a complaint. How did it make you feel? It has made me feel unimportant, disrespected and also angry. It’s similar when we feel unheard. We lose connection with the other person and make them feel like they do not matter. It can lead to a loss of motivation, a desire to leave the relationship and is unlikely to resolve conflict which is the aim of most difficult conversations.

An easy way to deal with this is to prepare yourself for that conversation.

Photo by Andrea Piacquadio on

Here’s how:

We never know  how the conversation will go or a person’s reaction to what we will say, however, we can use some simple techniques to counter-act the fear that we may have of the other person’s reaction. Ultimately, we may fear rejection, disapproval, aggression and the discomfort that we feel (such as anxiety or sadness ) when we confront those tough emotions. We can also plan before hand to make the best of any difficult conversation.

Firstly, work out what you want out of the conversation. Do you want to hand in your resignation or end the relationship? Express a need or emotion ? Seek redress for wrong-doing ? Apologise for your own wrong-doing? Agree a standard of behaviour and a way of communicating? These are all valid outcomes (and not the only ones!) and it’s a good idea to decide what you want to achieve before having the conversation.

Once you have decided,  have a conversation with somebody that you trust to discuss the facts of your conflict. This will help you to understand whether you have overreacted or have misinterpreted the other person and see it from another person’s perspective. 

It’s always advisable to get some distance emotionally between the offending behaviour or event and having the conversation. The reason is to calm down and distinguish the story from the facts. This will help you seek rational solutions that you will both benefit from.

Practice with somebody. This person needs to be honest with you about how you come across. Try role playing the scenario with yourself as the other person. It’s a powerful way to get into the other person’s shoes.

Photo by Christina Morillo on

How do I hear and be heard ? Key Tips !

  • Take control of the conversation by asking the other person to speak first. Reassure them that you will not interrupt them and that you are listening to them. It’s always good to be polite by thanking them for their time and for sharing their experience.
  • Be open to their emotions and perceptions and summarise them at a convenient point e.g. “ so you felt angry that I didn’t consult you before taking that action and you saw this as disrespectful on my part” . Notice the lack of  judgment in that statement.
  • Wait until the other person has finished and then express how you feel and what you want. Be direct but careful not to blame, criticize or insult. It’s ok to tell the other person that you feel angry, it’s not ok to shout and insult or physically intimidate.
  • Use phrases that express empathy to the other person’s perspective such as, “ I can understand why you felt that way” or “ ok , I hadn’t seen it from that point of view and understand why that made you angry.”
  • Remember your body language. You can give away what you really think and feel very subtly through the body , tone of voice or even your silence. Be aware of how this may be happening.
  • If it’s really becoming uncomfortable and nothing seems to work, tell the other person that your intention is to resolve conflict and that the relationship you have is important to them. If necessary, ask for a break. You might even consider involving a neutral third party to act as a mediator but be careful who you choose!

In my next blog post, I’ll be writing about how to handle volatile emotions in any type of conversations. But for now, do you have any tips of your own? If so, please feel free to leave a comment!

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