How to make difficult conversations a little less difficult

Difficult conversations exist everywhere; with people who jump the queue to breaking bad news to loved ones. It's something we're never taught so what can we do to make these conversations easier?

When I was in my early 20s, I became a project manager, my first role was for a tech agency and I remember being mentored on how to have a difficult conversation with a client when their website was down unexpectedly. Fast forward a few years, I approached an intimidating business owner with big questions about the standards and outputs of his work. Difficult conversations have punctuated my career and yet, they never seem to get any easier.

As a qualified Executive Coach, I initiate difficult conversations with my clients pretty on a regular basis to help their professional and personal growth, but there’s room for growth for me too. I decided I want to be better at having difficult conversations so I began to research and talk about it in the last few weeks. The other month, I hosted an Agile In The Ether community session on making difficult conversations less difficult and I was humbled to hear raw and honest accounts of difficult conversations. I researched books packed full of tips and put into practice a few ideas myself, so here we are, a summary of my reflections.

Unpacking the term

First, we need to focus on the definition of a ‘difficult conversation’, here’s a definition I particularly like:

“Anytime we feel vulnerable or our self-esteem is implicated, when the issues at stake are important and the outcome uncertain, when we care deeply about what is being discussed or about the people with whom we are discussing it, there is potential for us to experience the conversation as difficult” - from ‘Difficult Conversations: how to discuss what matters most

When the outcome is uncertain there is an aspect of this situation in which we can’t control, we can’t control how the other person reacts and therefore we have to park the ego at the door.

Difficult conversations require skill, to listen and communicate effectively but also to show courage and humility which is probably what makes them so damn difficult. Neils Pflaeging hit’s the nail on the head for me:

“When talking about organizational leadership, even the best example just doesn’t help! At least not as long as one, almost magic ingredient for change, or transformation, is missing. And that magic ingredient is our image of human nature, the way we think about people around us, and what drives them.”

The simplicity of this is beautiful, it’s not about complex organisational models or the latest project management software to improve team cohesion (or people cohesion in general).

Three ways to make difficult conversations, less difficult

Mindset shift

From deciding to have the conversation to initiating it with the other person, it all takes a shift in mindset, moving from a place of possible defensiveness to vulnerability and curiosity. This is one sentence, so quick and easy to write, but it’s a milestone moment in itself.

We know that difficult conversations take courage because making the decision to even have the conversation is hard. If I’m the initiator of a difficult conversation then it’s because I’ve recognised a boundary has been crossed or I have a need or an ask to make of someone else. Therefore, way before you’ve even instigated the conversation, it’s important to spend time reflecting on what action has happened, how it’s made you feel, and what you need from the other person in order for the conversation to be successful.

Photo by Oliver Cole on Unsplash

As the great Brené Brown says, there is no courage without vulnerability, so the best difficult conversations start from a place of curiosity, coming to the table acknowledging that there are questions and the difficult conversation is the opportunity to get answers from you or the person you’re speaking to. This means that you’ll need to think about:

  • What do you know to be true and what information is missing?
  • What contextual factors are going on for you and the person you’re speaking to?
  • Has this sort of situation happened before and how did you react? Did you accept it or did you call it out

Language shift

There are hundreds of thousands of words to choose from so choose yours carefully. In my research, I cam across Marshall Rosenburg’s guidelines on ‘Nonviolent communications: A Language for life’ - just the title alone is alluring, right?!

Marshall encourages us to make distinction between feelings and thoughts but the one that resonated with me the most was this:

“Distinguish what we feel and how we think others react or behave”

In other words, by saying, “I feel ignored” automatically suggests that the other person has deliberately intended to ignore you, but what if they didn’t? How can we backtrack just a couple of steps to both share our feelings and allow the other person to explain their version of events.

Brene Brown shares a great way to help with sharing feelings in a vulnerable way, “The narrative I’m telling myself is this…” it still allows you to share your feelings in a way that is true to you and your experiences, but it also invites the other person to share their narrative, which might be very different to how you’ve observed things.

The listening shift

I mentioned the ability to listen at the start of this post but it’s something I want to end on.

Reflect on the last conversation you had which was longer than 20 minutes, tell me how often you thought:

  • about what you were going to say before the other person had finished speaking
  • you’ve done what they’ve done a million times before and you know the best way to solve their problem
  • about something entirely unrelated, like what you’re going to have for dinner

The ability to listen is a completely over-looked skill but when our attention and time are two of our most limited and in-demand commodities, the best thing we can do for others is to stop and listen. Like truly actively listen. Listening like a detective looking to understand more about that person, how they found an experience, why did do they do something or on the flip side, why didn’t they do it.

The good news is that Michael Bungay Stanier has provided 7 really awesome questions we can start asking others, as a great opportunity to put your listening skills to the test. ‘The Advice Trap’ is firmly glued to my desk, it’s easy to read and I can pick out some really useful tips almost always.

My final thought

I’m still figuring out how to confront difficult conversations, some days I’m ready for it and other days I’m just not in the game. But the reality is that is it’s unavoidable, and if we dare navigate the world without the vulnerability and curiosity to stop and enquire about the people around us, then we feed our prejudices, our unconscious biases and we effectively become an island, isolated and insular.

It’s time to lean in to the challenge, what difficult conversation do you need to have? Tell me how it goes, I’d love to know what happened.

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