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3 Steps to Start a Difficult Conversation


I used to think conflict meant ‘dead end’.


At school I was nervous about it meaning losing a friend. In my romantic relationships, it would quickly inflame my doubts about our compatibility and fore-spelled a breakup. In community initiatives I saw opinion wars break meetings apart and derail well-intentioned projects. At work I translated it into ‘be careful not to show up like that (again)’ – putting an end to an aspect of who I am – and I saw some colleagues leave because of unresolved disputes.


So I have a lot of understanding for people who would rather steer clear of addressing conflict for fear of creating further disconnect with people and places they value, and for those who just get fed up with things not getting resolved and decide to leave.


We each find ways to cope with conflict depending on how assertive we feel about getting our own needs met, or empathic to other people’s preferences. You can probably recall moments when you’ve chosen to avoid someone, accommodate their way of doing things and set your preferences aside, competed to have it your way, or chosen to settle for a compromise.


Approaches to conflict

None of these approaches are wrong – it’s important to know when to let it go, when to be more assertive (my friend Rich Bartlett has a great course on building that skill) and when 50-50 is good enough. It all depends on how important the relationship or the issue are to you. But if the relationship matters to you and the issue is of high concern, being able to collaborate through healthy dialogue quickly becomes an important skill to have.


A lot of my work is about helping people put ‘collaborating’ more firmly on their menu of options when tensions arise.


First we need to acknowledge that conflict is at some point inevitable whenever you have more than one person in a relationship. Conflict doesn’t mean there’s something wrong with you, the other, or the connection. It’s an invitation to learn about what each of you need to feel welcome, seen and respected in your relationship. If you approach it well, conflict is a doorway to deeper connection, a positive process of getting closer and stronger together.


So how do you increase the chances of a connecting outcome?


Ready, Set, Reconnect…


Here are a few tips that help me, and they have everything to do with how you set up the conversation.


1. Clarify what you want


What do you want to achieve from the conversation?

If you connect to your most hopeful outcome, how do you imagine it will support you, the other person and/or your team?


This can be very specific and practical, e.g. “I want to come to an agreement about how we will distribute the remaining funds from last quarter”, or more open, e.g. “I’d like to feel safe meeting in the same space as this person at the upcoming conference”


Remembering what you want to achieve can be a helpful compass for you to return to if you get stuck, lost or overwhelmed in the conversation.


It’s a good idea to share your intention directly with your conversation partner right at the start. They’ll probably be more receptive and open to what you have to say and working towards a positive outcome together, especially if they’re apprehensive that you just want to put blame on them. If they want to share what they hope for from the conversation too, that’s even better!


2. Identify what happened


Conflicts are often characterised by a sense of distance – “there’s no way I can work with him – it’s like he’s from another planet!”. It can feel like a chasm has grown between us when there’s misunderstanding or disagreement. Or you might feel completely lost in the woods.. “How are we ever going to get out of this?”


To prevent further misunderstandings and orient the process around a clear starting point it helps to start by clarifying what actually happened. If we can agree on that, it’s a first step towards coming closer together and aligning our efforts to reconnect.


Can you identify at least one thing the other person did or said that triggered the disconnect between you?

Try to identify clear, specific observations, without interpretation.


For example, “she’s passive aggressive” is an evaluation or interpretation of their behaviour, but “she said my idea sounded like a ‘good old rational approach'”, or “I saw her smile at me and then leave the room without saying anything” is something we can both more easily agree on. It either happened or it didn’t.(1)


3. Tend to your fears and concerns


What do you expect to find challenging in the conversation?

What could you, your conversation partner, or a mediator do to support you?


Going into a tension is a moment of stepping into the unknown – we don’t know how the other person will respond (or how we will respond to them!). I find it helpful to acknowledge what I’m afraid of, and to reflect beforehand on what I’d do or need in that scenario, even if it’s very unlikely to happen.


For example, say my worst fear is that they’ll storm out of the room. What would support me and our connection in that moment? I imagine I’d be best to stay seated, take 3 deep breaths, and then call my support friend to help me process the feelings that come up, remember my intention, and decide what to do next from a (hopefully) calmer state of mind.


Going through these ‘if-then’ scenarios before approaching a difficult conversation has a lot more power than I initially realised. Why? Because when I discover strategies to look after the more vulnerable, fearful parts of myself, it helps me feel safer and more resilient within myself. I know what to do if shit hits the fan. As a result, I’m less in need for the other person to ‘show up safely for me’. People feel that extra space and confidence. It allows us both to be bolder about what we really need to say, less afraid that our truth and our expression will break the connection.(2) And that’s what really transforms a relationship – knowing we don’t have to sacrifice our authenticity on behalf of the connection.


Try it out!


When we’re well prepared for a difficult conversation, it’s much more likely we can find a way to reconnect, collaborate, and come up with mutually satisfying outcomes. Conflict then becomes the start of a conversation, not the end.


To help you go through these steps I’ve created this Courageous Conversation preparation toolkit. It takes about 15 – 20 minutes to go through and includes the prompts above, as well as a couple more helpful reflections. You could go through it for yourself, or use it to help someone else prepare for a difficult conversation. You don’t have to wait for a big tension to occur to give it a go – in fact I recommend starting out with a lower stakes challenge if this is new to you. Let us know how it goes in the comments below!


Want to go deeper?


If you’d like to learn more about supporting yourself, your collaborators, teammates or friends through conflict, you’ll fit right in with my upcoming course ‘Mediation Skills for Collaborative Teams’. The next live cohort kicks of at the start of July! Click here for more information.


If you’d like some third party support for a conflict you’re part of, I’m very happy to be invited to support your conversation. As a mediator, I’m here to help you find your way through the woods, understand what’s going on between you, and clarify what you need. You can find more info here.



  1. People rarely have perfect recall of events (unless it’s something already written down or in a photo/video). If you both remember events happening slightly differently, it might be helpful to acknowledge the nuance, e.g: “We’re starting with the understanding that in my memory, I recall [my observation of what happened], and in your memory, you recall [your observations]”. What’s important is that you both understand what behaviours, action(s) or words (accurately remembered or not) are sticking in each other’s memories and triggering tension, distance or pain between you. ↩︎

  2. We talk about this parallel relationship between ourselves and others in our Microsolidarity community-building practice too. Rich writes more about it here: https://www.microsolidarity.cc/essays/five-scales-of-microsolidarity#id-1-the-self ↩︎



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