Painter and Model (c1910) by Ernst Ludwig Kirchner. Courtesy Kunsthalle Hamburg/Wikipedia



How to have a difficult conversation

Avoidance will only foster more conflict. Aim for a shared understanding with these techniques from an expert mediator

Painter and Model (c1910) by Ernst Ludwig Kirchner. Courtesy Kunsthalle Hamburg/Wikipedia





Adar Cohen

helps families, businesses and communities have big conversations. He holds a PhD in conflict resolution from Trinity College Dublin and has lectured at Harvard University, the University of Chicago and, at the invitation of the King of Bhutan, at Sherubtse College. He lives in New Hampshire.

Edited by Lucy Foulkes





Need to know

I’m in a Zoom meeting, speaking to a screen full of black squares, trying to coax voices out of the void. The other callers are all members of an executive board, and they’re in turmoil over the strategic direction of their company. Several of them are no longer on speaking terms, and employees and shareholders have not been shielded from the drama. On a good day, these calls are tense, but more often than not they’re explosive. Only my camera is turned on, and I watch myself try to look optimistic.

I’m a mediator. I have helped people have difficult conversations for more than 20 years: in conflict zones and in living rooms, with leaders of corporations and foundations, and people in my own community. If you’ve ever avoided or postponed a difficult conversation, you’re not alone. Conflict avoidance is everywhere. At home and at work, we steer around conflict as prodigiously as we create it.

And yet conflict isn’t inherently bad. It offers us information about how we could work with others more effectively, improve our relationships, and grow as individuals. It’s far worse to try to avoid it, because you just end up creating new conflict – which ends up being more insidious and costly than the original issue.

When I help people have difficult conversations, we’re always aiming for one of three outcomes: a solution, a plan or an understanding. A solution is a grand bargain, a resounding win, a comprehensive resolution expected to withstand the pressures of all unknown future challenges. With a mediator this can happen, but it’s ambitious. We all have a tendency to hope for a dramatic and permanent solution, but this usually causes new problems by overburdening an already stressed relationship. A plan is more realistic, and is like a map for finding a solution. It leaves the precise terms of the resolution open-ended but provides a path forward. A plan reorganises the relationship with new boundaries, revised norms, and sets up shared expectations for how the trickiest parts will be navigated.

But the most realistic outcome, especially at the beginning, is to focus on reaching an understanding. An understanding is a new awareness of what the other person has experienced in the conflict; it’s a mutual appreciation for one another’s needs, fears and hopes. Reaching an understanding is feasible, provides great relief, and can lay a foundation for a plan, a solution and a new relationship.

For example, I recently helped a family to reach an understanding when the COVID-19 pandemic forced a college student to move back in with his parents. They were having difficulties renegotiating their relationships once they were suddenly living together again. Their renewed understanding led to a plan for new expectations and boundaries, which they’re currently using to navigate the uncertainties and discomfort of this period. I expect they’ll find their solution soon.

In my work as a mediator, I’ve learnt that successful conversations always involve what I call a ‘gem statement’. When two parties have listened long and hard to each other – have made the heroic effort to listen curiously and empathically even when they disagree strenuously – someone eventually unearths a glowing, priceless gem. It usually takes the form of a short, powerful statement, such as these two I’ve heard recently:

We’ve kept on fighting in part because neither of us is willing to walk away from this friendship. That’s something.
Even when we can’t agree on Dad’s medical care, I’ve never doubted your good intentions. I know you want the best for him.

It happens almost every time. From the muck of blame and anger, someone lifts out a beacon. I then seize the opportunity and hold up the gleaming gem for all parties to see. It lights the way toward a new conversation revolving around compromise, solutions and goodwill.

In addition to gratitude for the person who dug out the gem, I have also felt impatience. I’ve wondered, Why can’t they say something like this earlier in the process? Or better yet, at the beginning? Does the conversation need to naturally find its way to such a moment, or could we engineer it to happen much sooner? It seemed worthwhile to find out, so I developed a process to reduce the amount of time people spend digging in the muck. And I’ve found it works: when people find a gem earlier on, they experience less pain and more benefit from having their difficult conversation.

This Guide is to help you do this – without a mediator. Mediators can be helpful during challenging times, but we don’t actually resolve peoples’ conflicts. We create the conditions in which people feel heard and acknowledged, increasing the quality of their communication and problem-solving. When you’re facing a tough conversation, it’s not really the mediator you need – it’s the conditions we’re good at creating and maintaining.

If you don’t feel safe or if your situation involves illegal activity or any type of abuse, this Guide isn’t right for you. In those instances, get help from a professional right away. There are also some situations that don’t call for further conversation – some relationships or difficulties are better left in the past, and you should trust your instinct about whether a conversation is the right step for you. But if you think talking could do some good, then this resource can help get you started.

Maybe you feel misunderstood or unappreciated at work. Or maybe you’re caught in a recurring family pattern that causes pain and drives you away from the people you love. If you feel hurt or angry when thinking of a difficult conversation you need to have, there is a good chance that the relationship is important to you. Whether it’s a relationship within your family, at work or in your community, it’s become this challenging because you have a vested interest, you care deeply or your future is somehow intertwined with the person you need to talk with.

If you feel the situation could improve if someone really heard what you have to say, there’s hope. If you feel ready to make an earnest effort to really hear someone in return, there’s even more than hope. Remember that your goal here is not to find a quick solution or plan straight away – that’s tempting but unrealistic, and might backfire. Your goal is to understand each other.

What to do

1. Prepare for the conversation

The first step is a thought experiment: think about the person with whom you need to talk, and allow yourself to imagine that you just finished having the best possible conversation with them. You were heard fully. Each of your concerns was addressed to your satisfaction. If an apology was appropriate, you received an excellent one. Stay with this – just imagine it! You’ve reached an understanding that gives you confidence in the future of the relationship. This is a challenging thought experiment, but you’re almost there… You are relieved, you feel lighter, and even grateful to the person you’ve been in conflict with.

2. Dig out a gem

What would you say to them in this moment? (Remember, in this exercise you’ve been heard, you’ve received an apology, and it went exceedingly well.) What would you say to your counterpart if all of that happened? What’s ‘underneath’ the conflict? What’s true when you’re not consumed with negative feelings? Write down the first gem statement you think of. You can write others too, but usually the first one is the real deal.

Your statement should be an authentic expression of how you’re feeling, but should also have significant meaning and positive impact for the other person. For example, two more gem statements I heard recently were: ‘I can tell you care a lot about reaching our team’s goals, and I have a lot of respect for you.’ You can tell it’s a gem when you’re terribly tempted to tack on a grievance to the end of it. Like this: I can tell you care a lot about reaching our team’s goals, but the way you go about it is causing great difficulty to everyone around you. If you find yourself doing this, leave out the second part. You’ll get to say it, just not here.

3. Ask yourself if you’re ready

Are you willing to say the statement to them? We recoil from being generous and kind when we feel our counterpart doesn’t deserve it. Moreover, making such statements can put us in an even more vulnerable position. If that’s the case, it might help to think of this another way. Uttering your gem statement is a temporary discomfort; the benefits you’ll experience will be lasting and profound.

At this point, you should share this Guide with the other person. Even if you don’t follow these steps closely or have the conversation right away, it will be helpful simply to both read the Guide and give thought to it. If you do proceed with a conversation, having this Guide in advance means that they will have undertaken this same process and unearthed a gem statement for you, which will likely mitigate your vulnerability and discomfort.

4. Phone a friend

Tell a friend who isn’t involved in the conversation what you’re going to do. The purpose is not to craft the gem statement together, and it isn’t even to get their advice. Instead, say the four sentences below to your friend:

  • The biggest emotion that I’m feeling toward the person I need to have a difficult conversation with is…
  • The biggest emotion that I expect the person is feeling toward me is…
  • The gem statement I will make to them is…
  • My hope for the conversation is…

The fourth sentence – identifying your hope for the conversation – is a critical piece of your planning. Remember that the best initial outcome is achieving a new, shared understanding, rather than a comprehensive solution or a detailed plan. New understanding can bring you relief and allow space for forward movement, without expecting a miraculous resolution of all tension and conflict in the relationship.

Chatting with your friend can modestly decrease your pre-conversation jitters. You’ll likely get some friendly support and sympathy, and you might discover a revision or adjustment you’d like to make to your gem statement.

5. Start the conversation

This could be done in person, if you feel comfortable, or by phone or video. Most importantly, exchange gems first thing. For many this is the hardest part, but it will be over before you know it! Say your statement, immediately followed by: ‘I say this because I think if we both really try, we can work this out.’ It will be awkward. Do it anyway. Time and time again, the people I’ve mediated for point back to this moment as one they dreaded, but that turned out to bring them great relief. One likened it to jumping into the water for a rejuvenating swim: ‘When I finally did it, I wished I’d done it sooner.’

Once you’ve both made your statements, ask your counterpart four questions:

  • How are you feeling now?
  • We’re both here because we think we can work this out. What’s still in the way for you?
  • What can I do to help?
  • Is there anything else you want to say to me?

6. Listen and talk

Listening to someone you’ve been in conflict with – or with whom you’ve been avoiding conflict – is uncomfortable, frustrating and painful. When it gets difficult, remember your purpose. Why are you having this conversation? What’s the hope you wrote down and told your friend about? Holding that in mind will help you to keep listening.

I recently helped a group of siblings struggling to care for their ailing father. They were proficient in navigating his complex medical issues, they each cared deeply for him, and they were all willing to dedicate the time needed to coordinate his care. But animosity and mistrust forged by decades of conflict made even the most basic communication and coordination impossible for them. As they listened to one another, I saw agony in their faces. Despite sharing the same goals (giving their dad the best care they could, and sparing him from the emotional angst of seeing them fight), they could scarcely tolerate listening to one another at all.

Over our sessions, that started to change. They didn’t reach a comprehensive solution, and they certainly hadn’t warmed to each other. But they achieved a powerful understanding – one with the potential to support and inform the way forward. They all agreed they’d no longer involve their father in their conflict, and that they would approach their disagreements more directly. This meant that their father would suffer less, and not be caught up in their fraught bickering – a key goal for them all.

Mediators are able to trust the conversation process because they’ve seen the powerful effect of listening again and again. Listening when it’s hard – especially when it’s hard – puts people on the fastest track there is to resolution. There is no more productive and efficient activity in a difficult conversation than listening. Just as you need to be heard, your counterpart needs to be heard too.

Whether you agree or not actually doesn’t matter much. Whether their points are with or without merit isn’t as important as you think it is. In fact, a viable external solution to your conflict might not exist, but just listening can vastly improve the situation. Being fully listened to causes people to release long-held demands and grievances. In other words, there isn’t a problem to resolve if the problem dissolves.

When it’s your time to talk, there are a few guidelines you should follow. You might need to express frustration, pain and anger. Here are the ways to help your conversation partner to hear you:

  • Describe your experiences and emotions rather than listing your counterpart’s mistakes and faults. This minimises counterproductive argument and can unlock empathy.
  • Filter your grievances. If something wouldn’t make your Top Three Grievances list, leave it out of the conversation. People in conflict are at their worst in terms of being able to hear, absorb and respond productively to critique. Use your partner’s limited bandwidth efficiently.
  • Look back at the fill-in-the-blank sentences you read to your friend and see if there’s anything you’d like to share. Has something shifted since you filled in these sentences? Have you been surprised by something? Can you point to something happening in the conversation that reinforces your biggest hope?

7. Close the conversation

As the conversation draws to a close, ask one another: ‘What has changed for you as a result of this conversation?’ Maybe you felt heard in a new way, or you understood the other’s experience more fully, or you’re not feeling quite as much of a difficult emotion. Try to also make an expression of gratitude towards the other person – no matter how small. It needn’t be a full-fledged compliment. What’s one thing you appreciated about your partner or how they showed up in the conversation? Lastly, share one commitment you’re willing to make as you conclude this conversation. Reach, but be realistic – remember the siblings who made progress, but didn’t resolve their conflict completely.

Key points – How to have a difficult conversation

  • It’s common for people to avoid conflict, but avoiding it tends to create more of it. Approaching an awkward, upsetting or long-avoided conversation isn’t easy, but it can be done effectively. Whether it’s a relationship within your family, at work or in your community, you can have a difficult conversation successfully without the help of a third party.
  • There are three potential outcomes of a difficult conversation: a full-blown solution (tempting, but unrealistic), a plan (a map for finding a solution) or an understanding (which establishes a new awareness of how the other has experienced the conflict, and lays a reliable foundation upon which a plan and solution can be sought). In attempting a difficult conversation without a mediator, I recommend first seeking an understanding.
  • In my work as a mediator, I’ve found that a single statement has the potential to transform the conflict. I call this a gem statement, and it captures what’s ‘underneath’ the conflict. Sometimes it’s an expression of acknowledgment or empathy, and sometimes it’s merely an observation, but it has great meaning and impact for the listener.
  • The gem statement is usually unearthed toward the end of a stressful, exhausting mediation. By preparing for your difficult conversation in advance – writing your gem statement, talking to an uninvolved friend for support – you can save yourself hours of agony or discomfort. If you can share this Guide with the person you need to talk to, they can dig out a gem for you too.
  • In the conversation, listening is everything. It’s the most productive and efficient activity you can do in a difficult conversation. A simple solution to your conflict might not exist, but listening can enable people to release long-held grudges. In other words, through structured and focused listening, instead of resolving the conflict, you are dissolving the conflict.
  • When it’s your turn to talk, you might need to express frustration, pain and anger. You can increase the likelihood you’ll be heard by describing your experiences and emotions (rather than listing your counterpart’s mistakes and faults), filtering your grievances (so what’s most important to you gets heard), and returning to your hoped-for outcome.

Learn more

A common mistake made by well-intentioned people trying to have difficult conversations is to pass over the critical work of understanding one another. In rushing to find the grand resolution to their conflict, people forge ahead with conversations that backfire because the emotions driving the conflict are not being considered, voiced or validated. This causes new damage to weakened relationships, and the conflict deepens.

If you feel like this is happening, try to remember that your goal is to achieve an understanding – rather than a plan or a solution. When people seek plans and solutions too quickly, they focus on the terms and conditions of an agreement. This inevitably orients them in a bargaining mode, which means their primary focus is on advocating for themselves. Try instead to listen to one another’s emotions, which can open up new space for empathy, connection and trust.

You might also need more than one conversation – it’s important to be realistic about how much can be accomplished in a single session. The careful process and intentional listening you undertook can achieve a ‘breakthrough’, so that future interactions will gradually repair the relationship without needing a formal process. But often you need to return to the topic more than once.

A marathon hash-out is rarely helpful: this is exhausting stuff. Before one of you burns out (and potentially moves the process backwards), pause the conversation to protect the progress you’ve made. Use one or more of the ‘Close the conversation’ steps above to mark a conclusion of that instalment of the conversation. This type of forward-looking pause has an important benefit. Time away from the conversation enables you and your partner to absorb and reflect on what has been said, and where you want to go next. A well-timed pause could leave you both wondering more positively about the status of your relationship, priming you both for greater progress in the next encounter.

Many of us avoid conflict as much as possible, and there are many discomforts involved in facing a conflict head-on. But you can succeed in having a difficult conversation, and you can do it without hiring a mediator. Seek an understanding rather than a solution, and spend as much energy as you can muster on listening. These conversations are heavy, yes, but that’s not a good reason not to have them. If they’re heavy, then why carry them with us for weeks, months or even years?

Links & books

If Israelis and Palestinians who’ve lost loved ones in the conflict can sit down with one another for difficult conversations, maybe there’s hope for all of us? The documentary film Encounter Point (2006), directed by Ronit Avni and Julia Bacha, tells their story. It’s inspiring and instructive.

The illuminating TED talk 10 Ways to Have a Better Conversation (2015) by the American radio journalist Celeste Headlee offers tips on having better conversations, and they’re relevant to conversations of the more difficult variety too.

My TED talk How to Lead Tough Conversations (2019) further explores the ideas in this Guide. It can help you before your own tough conversation, or afterwards – when you’re ready to help others have theirs.

Take heart and be encouraged by that timeless beacon of empathy, the American television host Mister Rogers. In the clip ‘What Do You Do With the Mad That You Feel? (1997), he gives his advice about dealing with anger. It’s for kids, of course – but his message is powerful and relevant for us all. The full episode is also available online.

The poem ‘Gate A-4’ (2008) by the Arab American poet Naomi Shihab Nye is a wonderful piece about encounter and connection across difference.

The book The Third Side: Why We Fight and How We Can Stop (2000) by William Ury, a negotiation specialist at Harvard, is a seminal work on conflict resolution.

Another book by an expert on mediation and peacebuilding, The Little Book of Conflict Transformation (2003) by John Paul Lederach, provides helpful advice for using conflict to fundamentally reshape relationships.