Self Development: How to have Difficult Conversations

Feb 24, 2023 | By Saranne Durham

Difficult conversations are a part of life. Many people try and avoid them. However, the reality is that, sooner or later, continuing to brush things under the carpet creates additional problems. In most cases, embracing a difficult conversation is a good idea. It often decreases anxiety levels and allows for a way forward. 

For most people, having a high-stakes conversation is challenging. And very few people are trained to have them effectively. Being able to have a difficult conversation starts with being grounded and having the ability to express yourself. Through a good personal development course, it is possible to acquire and improve practical skills. Developing this essential life skill is a great way of investing in yourself. And at the same time working at creating better connections with people in your personal and professional areas of life.

Why are Some Conversations Difficult?

Some conversations are easier than others. The most challenging conversations to have, are those where there are strong feelings involved. Specifically, where there is a disjunction between how we feel and the action we need to take. Often these conversations have two additional aspects to them. A “what happened?” question and an identity component. Let’s look at each of these aspects. 


The reason feelings conversations can be difficult is that they are emotive by nature. Thus, they provoke intense and sometimes conflicting feelings which we then grapple with. Adding into the mix is that often we tend towards hiding these feelings. This might be because they make us feel vulnerable or we worry that the other person will see us as weak. In both instances, it can disadvantage us and thwart the purpose of the conversation. Alternatively, strong emotions may cause an emotional outburst whereby people involved in a conversation are hurt or insulted. Both scenarios have the same end result. They are counter-productive to resolution and make what was a difficult conversation, very much trickier. 

What Happened?

“What Happened?” conversations involve trying to find out who is right or wrong. Almost immediately this brings a level of tension into things. Because, in determining whose story is correct, one is essentially saying the other party is wrong to allocate blame. It’s also the type of conversation where pre-assumptions are made. Despite that up front, we have a limited amount of information or even incorrect information. These types of conversations can descend quickly into a blame game, which further escalates emotions. One of the emotions that escalate when this happens, is anger. And anger is particularly harmful to good communication and finding a resolution. 


Identity conversations are tough because they can often be a reality check. They force us to see how others see us, which sometimes isn’t how we see ourselves. This means that during an identity conversation, it can feel like our sense of self is being questioned or attacked. Often this results in us getting defensive. Which is counter-productive during a conversation, but particularly so during a tough conversation. This is because it shifts the focus from the issue at hand, onto the people involved. Thereby, instantly personalising things when the best way forward is to keep things objective.  

How to have Difficult Conversations

Problems are more easily resolved when, instead of focusing on right or wrong, we try and understand someone else’s perspective. This changes a difficult conversation into a learning conversation. One of the ways to do this is to use a reflective listening approach. After establishing that you have understood the other person correctly, you can then move on. The next step is to see how each of you has contributed to the challenge at hand. 

If we try and be empathetic in a conversation that’s emotionally charged, we can often de-escalate things. However, to be truly empathetic you need to know yourself, be quite grounded and also be aware of how you express yourself. Acknowledging emotions should help decrease tension, thereby enabling resolution. This acknowledgement is of both your and the other person’s feelings. Thus, shouldn’t result in side-lining one person’s feelings.  

A big part of having a critical conversation is therefore self-awareness, feeling grounded and humility. The ability to self-reflect and willingness to consider how you might need to change are important to finding a resolution fairly. Tough conversations also get easier to have when we are more confident about our skills. And a big part of that is being willing to constantly improve them. 

How to Navigate a Critical Conversation

We aren’t always able to choose the conversation at hand nor when a conversation will take place. And even when you’ve thought things through, they don’t always play out how you envisioned them to. But we can always choose how we conduct ourselves and our responses to the other person. This makes upskilling yourself, ahead of difficult conversations, a great idea. 

SACAP Global’s short course on How to have Critical Conversations develops practical skills to help you manage tricky conversations. It teaches you how to navigate conversations towards better outcomes and resolution, thereby preventing further division and escalation of tension. This specialised short course is open to anyone who would like to develop their skill set. 

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