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How to Navigate Difficult Conversations: Tips for Effective Communication

  • Feb 9
  • 5 min read

Updated: Apr 29


Two men in a bright office discuss business at a flip chart. One holds a marker. Large window with a mountain scene in the background.

Life & difficult conversations

Life is a rollercoaster, as the metaphor goes, and our fleeting ride on the rollercoaster of life is full of a challenging exchanges with people that we love, people we are indifferent towards, and people we secretly don't get along with.


Telling your housemate that he should not leave dishes in the sink. Breaking up with your partner. Confronting someone who is behaving in a disrespectful manner. Asking your manager for a raise. These are just some of the elephant-in-the-room discussions that you will be confronted with throughout your life. Considering the frequency of which the situations listed above take place, you would think that we are all experts in dealing with challenging topics.


Think again.


One minute you’re arguing about who left the dirty dishes in the sink, the next minute, you're passionately debating whether pineapple belongs on pizza and somehow, that spirals into a heated discussion about why you always leave your slippers hanging around the house. Meanwhile, the dishes are still in the sink and no closer to getting the treatment that they deserve! Three hours later you are left wondering where the conversation took a turn towards emotional warfare and a Mexican standoff.


Does this sound relatable to you? If so, you are in luck, because this blog article will discuss exactly where things have been going wrong for you in these situations. You will go from sounding like a chaotic ranter like Kanye West to a quiet, measured conversation master such as Jay Gatsby (The Great Gatsby). Without further ado, let's get stuck into the nitty gritty.


To confront or not to confront: that is the question

In many difficult conversations we believe that if we try and steer clear of problems that we

Man in a blue shirt and tie is pointing and shouting, expressing anger. Gray background enhances dramatic mood.

will feel weak and that we are incapable of standing up for ourselves. However, the flipside of the coin could be that if we do confront someone things could escalate beyond repair. In his book, 'Difficult Conversations', Douglas Stone mentions that "delivering a difficult message is like throwing a hand grenade. Coated with sugar, thrown hard or soft, a hand grenade is still going to do damage. Choosing not to deliver a difficult message is like hanging on to a hand grenade once you've pulled the pin."


I know, neither of the two options sound particularly attractive. However, there are tactics that you can use to avoid turning challenging interactions into a War of the Wor(l)ds. Common mistakes and various methods will be outlined below and should provide you with the tools you need to change the way your conversations turn out.


Things left unsaid

Conversations are pretty simple right? One person says something and the other person provides a response to what was said.


If only it were that simple.


During an average interaction two conversation partners will be engaging in an exchange of spoken and unspoken words, aired and unaired thoughts, and emotions. Therefore, it is crucial that you find out what these various factors are. By entering conversations with curiosity you can turn the exchange from an accusation into a moment of learning. Ask your partner in crime why they feel a certain way and try and keep an open mind about their perspective. Too often we get caught in the blame game and searching for facts. In reality conflicts are just two people engaging with each other while having differing values, perceptions, and interpretations.


Impact ≠ Intention

One of the greatest mistakes most of us make while interacting with each other, is assuming what the intention is of our conversational partner. To add insult to injury, we also tend to assume (make an ass of you and me) that the other person's intentions are malicious. Douglas Stone has a great way of solving these types of scenarios. According to the author of 'Difficult Conversations' it is important for us to separate the impact of what people say from their intentions. After all, it is currently not possible to read people's minds 😉. This would mean that we should not jump to conclusions about certain comments about us and try and understand what the other person is trying to say. By separating the impact from the intention, we can take the emotional aspects out of the interaction.


The Blame Game

When you look at two children arguing, the conversations tend to go a predictable way. "Jimmy did it!" says one child called Kevin, upon which Jimmy declares "No I didn't, it was Kevin!". Not the most productive way of resolving an argument, I am sure you would agree. By engaging in 'the blame game' we stop ourselves from discovering what the underlying issue is that is causing the problem and it will prevent both parties from looking for a solution. After all, it takes two to tango!


A good way of planning for these types of interactions is to look at the situation from the viewpoint of a neutral person or a third party. A common mistake that we make is that we enter discussions solely from our perspective and this will inevitably lead to a situation of conflict. By analysing the state of affairs before starting the conversation you can admit to your contribution to the disagreement. This will help the other person feel more relaxed to discuss their role and things that they could have done better.


If you do decide you want to call someone out on something it is better to do it in the shape of your feelings. Don't use 'you did this...', but you could use 'I feel slightly frustrated about ...'. When you express your feelings, try not to blame or judge the other person. People can disagree with you on a lot of things, but they cannot disagree with how you feel.


Agree to disagree

In the previous chapters, I discussed the importance of understanding the thoughts, ideas, and perspectives of the other person. People like to feel listened to and by giving your conversational partner a platform you can make them more appreciative towards your side of the story. However, this does not mean you have to agree with the other person's opinions and views. You can understand the other person's outlook without sharing this person's views. Many people spend an excessive amount of time trying to convince the other person that they are right about certain things, but the irony is that by trying to change someone, you usually get the opposite results. To finalise this blog post I would like to share the following quote with you that perfectly summarise the content of this article:


"Seek first to understand, then to be understood." – Stephen Covey


Further reading

The topic discussed above is too broad to condense into a single blog post and therefore I would like to suggest the following book for the purposes of further reading:

  • Difficult Conversations: How to Discuss What Matters Most by Douglas Stone



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