Tips For Tackling Difficult Conversations

Lily Low
Published in
4 min readFeb 26, 2022


Photo by Priscilla Du Preez on Unsplash

Difficult conversations are often something we dread, yet these are the conversations that we need to have.

What makes it difficult? It can be conversations about reinstating your personal boundaries, surrounding financial struggles, expressing discomfort over something another person may have done, accepting that you could have done something wrong as well.

How do we mentally prepare ourselves to engage in these difficult conversations? These are some tips on how we can navigate through them:

It may not always go according to plan

We can plan as much as we want on the ideal way our upcoming conversation should go. However, we do have to keep in mind that there are things that are out of our control and circumstances can change. The person on the receiving end of the conversation may have different emotions about the situation/topic at hand, they may not be in the mood or mindset to be having this conversation.

Do not beat yourself up over it if a conversation does not go exactly the way you planned. It is important to keep this in mind to avoid blaming ourselves for things that are out of our control. Remember that the direction the conversation ends up going towards is not a sole reflection of your ability or worth.

Be ready to deal with the emotions coming your way (as well as your own)

As mentioned earlier, the person we are having this conversation with may have different feelings about the topic/situation. If a person is having a bad day or has a lot of stress on their shoulders, they may be unwilling to talk or they may be lashing out at those around them.

Do not take their lashing out to heart. At the same time, discern the root of their behavior. Is this common behavior whenever a difficult/unpleasant situation arises, or is this a one-off occurrence? We have to be mentally prepared to meet the onslaught of different emotions that can arise from having the conversation.

Additionally, we also have to be mindful of our own emotions. We have to be cautious about the way we react to the person we are speaking to, otherwise, the conversation can end up going in circles or nowhere. Acknowledging your own emotions beforehand — separate from the other person — can help you to be firm in your stance and in bringing the conversation back to the main point.

Be ready to listen!

Having a conversation involves give-and-take. You are both talking it out as much as you are hearing each other out. For the conversation to be productive, it has to involve effort from both sides — this should not be a one-sided conversation.

Have a contingency/backup plan

Remember what I said about things not going the way we want them to? Hence, having a contingency plan is important.

How do we go about this?

For example, Plan A could involve us cutting to the chase and getting straight into addressing the conflict. Through this method, we will not be delaying or avoiding something that could be making both parties uncomfortable.

However, Plan A might fall through if the other person is unwilling to open up so quickly. Plan B could be us taking charge of the conversation and steering it to a different light-hearted topic first. It could be discussing a new movie, catching up with each other on how work has been, sharing opinions on a series both parties are a fan of. It can also be doing an activity together (e.g. painting, rock climbing, pottery) before finding a quiet place to have the conversation over a cup of coffee. Plan B allows for a little interlude and relief before the big conversation.

Plan C would come in if the other person is completely avoiding you and/or the conversation. This decision would boil down to your discernment if this is still something you would want to pursue. Will the other person be open to hearing your side of the conversation? Will things change for the both of you if you were to have this conversation? Has this person been respecting you and your boundaries, or have they been walking all over you? If your answers to these questions are negative, you may have to mentally prepare yourself for the possibility of not carrying out this conversation. Just like how our plans may change, we cannot always expect to get closure. Sometimes, it may be better to move forward without them.

Remember to breathe

This may sound silly because this reminder does not help in the content of the difficult conversation. However, this reminder helps in holding the conversation.

The possibility of facing something we are dreading may cause us to feel nervous or anxious. To keep ourselves calm and level-headed, there is a 4–7–8 breathing technique that we can try out! It involves inhaling for 4 seconds, holding your breath for 7 seconds, and exhaling for 8 seconds. This technique not only helps us in feeling calm before our conversation but can also keep us grounded in stressful situations.

I hope that these tips and reminders can help you in having these difficult conversations. Remember that self-blame is a disservice to you, keeping in mind that many factors can disrupt the conversation. Be ready to face both the other party’s emotions as well as your own. Take a deep breath, express your heart out, and be ready to listen — it will be okay!



Lily Low

“No darkness, no season is eternal.” | Writes about mental health, music, current issues, life, poetry, and faith.