Transforming tough conversations with empathy

Jane came to see me about having tough conversations at work. She was avoiding them with one of her team and she knew that she could no longer stick her head in the sand. She needed help. We talked about transforming tough conversations with empathy. Let me start with this: there are three things I know about tough conversations: 

  1. They are where the magical transformation happens
  2. They can feel hard and it’s easy to worry about tone and emotion (on both sides), especially as they are best done in person
  3. Many people have a limiting belief about them, which is, they hate having hard conversations and will bury their head in the sand instead! Jane was not alone. 

What do we find hard about tough conversations?

To start with, it probably doesn’t help to call them tough conversations, talk about setting ourselves up! And maybe there’s a question before which is, what makes a tough conversation? I think both of those questions are two sides of the same coin. In Jane’s mind a tough conversation is one where she felt like she was going to offend the other person and upset them. (This has been true for me in the past as well!)

I have also heard many people over the years telling me how terrible a situation they are now in because their manager avoided the difficult conversation. And yet, as I pointed out above, most of us know that it is in these conversations where the magic happens. The good news is that we don’t have to avoid these conversations or hide our own needs and wants.

Communicating effectively, and empathetically can be learned. As we learn more about ourselves, we become more aware and willing to accept the fact that we’re not perfect. We understand that there are things we can change about ourselves, like how we respond to conflict. 

On my walk this morning I was thinking about Jane and how we challenged this limiting belief that tough conversations = conflict. We considered how she already had these transformational conversations and how she could use the gifts she had to have them more often. The word empathy popped up. 

Transforming tough conversations with empathy

I don’t know about you but when I think about the transformational conversations I have experienced as the coachee/friend who is avoiding/not seeing clearly/is wanting to make a change they have all involved empathy. 

When Jane and I discussed this she realised that she was already having these transformational conversations in all areas of her life. As a parent and partner she was already gently calling people out on their behaviour but doing it from a place of empathy and compassion - the way she would want to be treated herself. 

When she had to have these so called tough conversations in the moment, she had the other person’s best interests at heart. In those moments we can all see the benefits.  I have seen it in my own life and whilst I can’t say that I enjoy being called out myself, I do appreciate it because we can’t all see clearly all the time. Sometimes we need a different perspective. 

Turning tough conversations into transformational conversations 

Everyone can be defensive, emotional, argumentative if they are accused or feel judged. But when the conversation is handled with kindness we are more likely to reflect,  apologise (if required) and feel grateful. The issue is not with the words but how they are delivered, and, sometimes by whom and when and where. My partner giving me ‘friendly advice’ in the middle of our kitchen when we are surrounded by hangry kids shouting “mummy” is not the best timefor us to have a difficult conversation! 

So what can we do to have transformational conversations that benefit the recipient? In my opinion, there are three things to do:

  1. Choose your time and place carefully. If you are in an office, go somewhere private where you won’t be distrubed.
  2. Ask permission - it could be as simple as, “could I offer you an observation?”. If it is appropriate you might ask something like “how much challenge would you like during this conversation?”
  3. Use your empathy skills and keep the other person’s feelings in mind. They need to feel safe and not judged/accused. 

How to use empathy in your conversations

Did you know that there are three types of empathy? Cognitive, emotional and compassionate. As a leader yuo might use cognitive empathy to figure out which tools will build the most trust and rapport within your team. You will rely on emotional empathy when you hear that your friend is experiencing a loss and compassionate empathy is what drives you to help a stranger in need. In your leadership practice there are practical ways to use empathy in your conversations: 

Assume the intentions of the other person are good

Go into a transformational conversation with an open and curious mind. If both parties expect the other to have their best interest at heart, they are less likely to be defensive and more likely to be able to really hear what needs to be said. 


I don’t mean to just listen but instead to really focus in order to hear and comprehend what the other person is trying to say. Listen with your ears and your eyes - looking for the nonverbal clues too. Listening like this allows the other person time and space to speak without the fear of being interrupted. If you want to, you can occasionally repeat back or paraphrase to ensure that you are understanding them e.g. can I just check that I am understanding what you mean…

Reflect rather than react

In transformational conversations take the time not to jump to conclusions or get defensive. Aim to put yourself in the other person’s shoes e.g. how much courage it may have taken for them to open up and to understand their perspective and opinion. 

Embrace the discomfort and vulnerability

We grow through difficult moments. As a leader part of our role is helping others develop and we know that staying the same is less comfortable than the discomfort of growth, so ultimately, the only choice is to change. In order to have happy and healthy working relationships we need to find common ground and learn to look at a situation through the lens, beliefs, experiences, values and expectations of others. This is how we create deeper connection. 

Happy endings

So what about Jane? At the end of the session Jane’s action was to have one transformational conversation and to explore how it felt for her and to get some feedback from the other person too. As she realised that these conversations were actually beneficial -not just to the other person but to the health of the whole team too, she actually started looking forward to them. 

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