Engaging Empathy and Mindfulness in Difficult Conversations

Have you ever dreaded having a difficult conversation with someone before? Unless you live by yourself in a cave, the answer is almost definitely "yes."

We often procrastinate or even try to avoid needing to have difficult conversations altogether. A part of us thinks, maybe, just maybe, things will resolve on its own.

That we don't actually need to speak our truth - or that the other person should just know how we feel and what we want. Of course, this rarely happens - so we can feel anxious or maybe even start resenting the other person

Avoiding difficult conversations kills connection and intimacy because it doesn't allow for vulnerable and authentic relating.

Below, I share 4 tips that may help you in approaching having challenging conversations with others. I hope they will also help you access the courage that is often needed to have these difficult conversations in the first place.

Remember, the following are skills to develop. They won't happen overnight - so try not to get discouraged. Just like any skill - they will take practice and patience to build.

Tip #1: Try to take some time and space to process your own emotions before going into a difficult conversation. For example, if you go into a conversation while you're angry, it's more than likely the other person will just become defensive - and also get angry.

A conversation is relational in nature. It's not a one-sided affair. So the first step is always trying to create some space between your emotion and your response (which in this case is the conversation itself) - rather than just reacting.

From this space, you're much more likely to be able to approach the conversation from a heart-centered place, rather than a fear-based place. When we're coming from the heart, we're much more likely to remain open and curious. Whereas fear often makes us closed-minded and inflexible - making it hard for us to see the other person's point of view or the different possibilities of working through conflict or a difficult situation.

Tip #2: Try to have clarity around what you're hoping to achieve through this difficult conversation. Just the fact that it feels difficult means that you care - and that there's some stuck energy you're hoping to move.

So having some clarity about what you ultimately want, by having the end goal in mind, will always make the process go that much more smoothly. And by clarity, I don't necessarily mean actions - like how you want the other person to change or how you want them to act or behave. Remember, it's only a conversation if you remain open and curious.

It's more about knowing what YOU want. How do YOU want to feel? How DON'T you want to feel? Both during the conversation and afterwards. And then it's often helpful to know how you want the OTHER person to feel. And how you don't want THEM to feel - both during and after the conversation.

Having this awareness helps guide the conversation (whether consciously or not) - because you've set the intention around the outcome you desire.

Tip #3: Try to be fully present and actively listening while in the midst of the difficult conversation. I know this can be especially challenging for those of us who have trouble sitting with discomfort. It's easy for us to become easily distracted - because the discomfort just feels too unbearable.

But try your best to be fully present. To allow the other person feel like they have your undivided attention, love and presence. I feel this is the greatest gift you can give someone.

It is from this space where we can actually employ empathy. To truly have a conversation, we must be able to understand where the other person is coming from. This requires listening mindfully, without judgment. And not interrupting or trying to talk over the other person - even if your own thoughts are screaming for attention or just want to "fix" things.

What is often helpful is to reflect back what you're hearing from the other person. Try to affirm and validate what the other person is saying. This doesn't mean you have to agree with what they're saying - just that you hear what they are saying and that you acknowledge their right to experience whatever it is they are thinking or feeling.

Tip #4: Try to ask questions. As I mentioned earlier, besides openness - curiosity is a key ingredient in moving through a difficult conversation. Instead of just offering your opinions the whole time, try to ask questions to better understand the other person's perspective.


Cultivating these skills allow us to better be able to step into another person's shoes so that we can understand where they're coming from - as well as understand what fears they may be facing. It's only through mindful listening, empathy, curiosity and the common goal of wanting a good relationship - can we hope to genuinely connect with others and get through difficult conversations.