Preparing for Difficult Conversations

Have you ever known that you needed to have a difficult or uncomfortable conversation with someone you had conflict with, but you felt too overwhelmed or confused to be able to start it? Has someone wanted to have a conversation with you and all you wanted to do was run away and hide?

In my work as a coach, I often help people prepare for conversations that they are dreading, that they would rather avoid, and that they are concerned will only make the situation worse. We often go into these kinds of difficult conversations feeling frantic and unprepared, hoping it will go well, and dreading that it probably won’t. Through my coaching work, I’ve developed a list of guiding questions that might be helpful if you are feeling unprepared for any of the following situations:

  • You have an upcoming mediation in which you know that difficult issues will come up;

  • You have been avoiding someone who is upset with you and you are aware it is only making things worse;

  • You really need to give someone some difficult feedback, and are concerned they won’t take it well;

  • You have been sitting on long standing negative feelings about someone that are getting in the way of your relationship with them.

The first step is to take the time to prepare.

We usually don’t take the time to prepare for difficult conversations, for a whole host of reasons. Sometimes, the situation feels too urgent to take time to think. If the feeling of urgency is coming from you, it can be helpful to get an outside perspective to determine if it is really as urgent as it feels. If the urgency is coming from the other person, it may be necessary to very clearly and concretely say that you need some time, and give them a timeline for when you will be ready. As hard as it can be to take the time to prepare, the rewards of doing so, in terms of the quality of the conversation, are well worth the challenge. It can go a long way toward changing the conversation in a way that will make it more likely to resolve and less likely to escalate.

And then for some of us, taking time away is not the problem. Sometimes we end up avoiding a conversation for so long that it feels even harder and more loaded to have it. In these situations as well, using the time specifically to prepare can provide the motivation and confidence that has been missing. This is not just more time to avoid, but is about going though a process of really thinking about how to approach the situation.

Some guiding questions to effectively use that time:

What am I trying to get out of this conversation?

What is the purpose of this conversation? What outcome would be satisfying? These questions are essential. If you don’t know what you are trying to get out of the conversation, it is very hard to make decisions and to assess if it is going well. Some possible answers to these questions might be improved relationships, deeper understanding or clarity, or relief of negative feelings. Sometimes there might be a tangible (substantive) objective you are trying to achieve, for example a parenting plan that everyone can live with, a new policy for dealing with workplace conflict, or an agreement with a neighbor about how loud it’s OK to play music.

Is there a possibility that something amazing could develop out of this conversation?

We usually feel very pessimistic about conflict. When preparing for a difficult conversation, we tend to focus on all of the things that could go wrong, and all of the ways that raising an issue can make an interpersonal conflict worse. While it is true that sometimes a conflict escalates after airing the issues, it is also true that conflict is often the catalyst for amazing new possibilities, deeper connection, and new ideas. It can be very motivating to be open to the possibility that something exciting, creative, or healing might come out of a difficult conversation.

Am I ready?

There are a number of elements to being ready to have a difficult conversation. The first is emotional readiness. Are you grounded enough to be able to be open-minded, flexible, and ready to listen to different perspectives? Are you ready to hear things that don’t feel good? Are you prepared to raise your concerns, even if they are not well received? Do you have strategies to ground yourself if you start feeling escalated in the moment?

The second is safety. Are there any safety concerns you have about this conversation? Those could be internal safety concerns, for example, knowing that you are likely to get emotionally triggered, or that you might give in too quickly to avoid difficult feelings. They might also be external safety concerns, for example, the potential for violence, reprisal, or other forms of conflict escalation. If you feel that the conversation might be unsafe, it is very important to get some support to develop a process that supports you and helps to balance power differences.

And finally, the third element of readiness is about information. Do you have enough knowledge of the situation, external or structural factors affecting it, and possible routes to resolution to be able to have a constructive and knowledgeable discussion? For example, when I work with parents who disagree about where to send their child to school, it is very important that they come in having done some research about the different options. The more research they have done, the more they are able to use objective criteria to determine what the best choice would be.

What do I know about the people involved in this conversation?

It can be so helpful to spend some time reflecting on what is going on beneath the surface for the person or people with whom you want to have the conversation. What do you think the other person might need from you to be able to give you what you need from this conversation? Are there different values or assumptions, or difficult feelings that may be getting in the way of resolution? Are there any particular behaviors or actions you might be taking that might be contributing to the tension between you?

What do I need to communicate?

Go in with a clear understanding of the main issues or concerns you need to get across. What is your main concern? Generally, people are more able to hear feedback when it comes in ways that still respect them as a human being. Can you find a way to express how their actions have negatively impacted you, without blaming or judging them as a person?

What process would help me to make sure that this conversation can be as constructive as possible?

After considering all of the above questions, you should be able to have a clearer idea of what kind of process would be the most helpful. If the conversation needs to have some formality to it, you might want to write out a tentative agenda, or pick a particular location that will make it feel more official. If you feel like you need some support to have the conversation, involving a mediator or other third party might help it to go more smoothly. If there is a big power dynamic between you and the other person, or you feel unsafe to have the conversation, it might help to have a support person present, and to have a clear plan as to how to end the conversation if it goes badly.

Is it worth it?

The final question to ask yourself – after all of this reflection – is “Is it worth having this discussion?” Think about what the most likely outcome of the conversation would be, as well as what is likely to happen if you don’t have it. What other alternatives do you have? Which ones feel like they would be the best options for what you are trying to achieve?

If you need some support to go through this process …

I’m hoping that for lots of people, this guide will help you to think through the conversation you need to have, so that it can be as successful as possible. If you are feeling lost in this process, or you want a bit of extra support while you go through the questions, feel free to reach out for some one-on-one coaching. I generally meet with people to help them prepare for a difficult conversation anywhere from two to six sessions, depending on the complexity of their situation and the extent of support they need. Alternately, if you are in the Toronto area, I also offer a public workshop called “Preparing for Difficult Conversations.” The next one will be in the fall of 2017. To stay updated on upcoming dates, or to find out about the coaching process, send me an email at, or sign up for my mailing list (sign up to the right of this post).

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Brook Thorndycraft Conflict Resolution Services
Brook Thorndycraft
Mediation, coaching, and training for families, workplaces, and individuals.

65 Wellesley St East, Suite 402

Toronto, Ontario, M4Y 1G7




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