Have you ever known that you needed to have a difficult conversation with someone, but you felt too overwhelmed or confused to know where to start? 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.  Anticipating an emotionally charged conversation can leave us feeling frantic and unprepared. Through my coaching work, I’ve developed a list of guiding questions that you might find helpful for any of the following situations:

• There is an upcoming mediation in which you know that difficult issues will be brought up 
• You are avoiding someone who is upset with you and you’re aware that it is only making things worse 
• It’s time to give someone constructive feedback and are concerned they won’t take it well
• You have been sitting on long-standing negative feelings that are harming the relationship

Take the space and time to prepare.

There are a whole host of reasons why we don’t take the time to prepare for courageous conversations.

Sometimes, the situation feels too urgent to take time to think. Is 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, ask for time. Try to be specific about when you think you will be ready.

As hard as it can be to take the time, the rewards of preparing are well worth the challenge. It can go a long way toward shifting the conversation in a way that will make it more likely to go well.

For some of us, taking time away is not the problem. Sometimes, when we have been avoiding a conversation for so long, it feels even harder to have it. In these situations, taking the time specifically to prepare can provide the motivation and confidence that has been missing.

Keep in mind that this is not intended to give you more time to avoid the conversation. It is meant to allow you space to really think about how to approach the situation.

Questions to effectively use your preparation time:

What am I trying to get out of this conversation?

Ask yourself what your purpose is for having the conversation, and what outcome would feel satisfying. These questions are essential. If you don’t know what you are trying to get out of the conversation, it is hard to make decisions and assess whether or not it is going well. Some possible answers to these questions might be improved relationships, deeper understanding or clarity, or relief of negative feelings. 

There may be a tangible objective you are trying to achieve. Maybe you need a written agreement about how to work together moving forward, or a new policy for dealing with workplace conflict. Sometimes what would help most is a meaningful apology.

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

It’s hard to find optimism when we are dealing with the painful emotions of a conflict. We tend to focus on everything that could go wrong. We fear that speaking honestly about a problem can make an interpersonal conflict worse.

While it is true that sometimes a conflict escalates after airing the issues, bringing the problem to the surface can also be a catalyst for amazing new possibilities, deeper connection, and ideas inspired by a fresh perspective. What if you could stay open to the possibility that something exciting, creative, or healing might come out of a courageous conversation?

Am I ready?

There are a number of elements to consider when readying yourself for a courageous conversation.

The first is emotional readiness. Are you stuck in a fight/flight/freeze response, or are you able to access emotional grounding and fluidity? How emotionally prepared do you feel to be able to speak clearly about what you need? Are you able to listen to different perspectives? What if you hear things that don’t necessarily feel good? What do you need to feel prepared raise your concerns, even if they are not well received? Do you have strategies in place to support yourself if you start feeling really upset in the moment?

The second element of readiness is safety. Are there any safety concerns you have about this conversation? They could be internal safety concerns. Maybe you know that you are likely to get emotionally triggered, or that you might give in too quickly to avoid difficult feelings. They may 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, get some support to develop a process that supports you and helps to balance power differences.

Finally, the third element of readiness is 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? What do you need to know about your workplace policies? Do you have a sense of how organizational or systemic issues might be impacting the situation? For example, if you are angry at a coworker because they are dropping the ball on an important project, it could be helpful to consider how established workload or project management processes might be affecting their capacity to do the work. 

It can be helpful to think about whether there is any information you could gather prior that might help you and the other person come to an agreement more easily. For example, maybe you want to advocate for more democratic decision-making within your organization and you know that it won’t be a popular idea with leadership. You may want to research how other organizations or teams have made a similar shift, and find out what the benefits were for them.

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

It can be incredibly 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 a courageous 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 you behaving in ways that might be contributing to the tension between you?

What do I need to communicate?

Go in with a clear understanding of the issues or concerns you need to get across in your communication. What is your main concern?

Generally, people are more able to hear feedback when it is delivered in ways that respect them as human beings. 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 hopefully 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. Maybe you need some support to have the conversation. In this case, you might involve a mediator or other third party. 

When there is a considerable power dynamic between you and the other person, or if you feel unsafe to have the conversation, it might help to have a support person present and to have a clear backup 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. Also consider 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 hope that 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 want a bit of extra support while you go through the questions, feel free to reach out to me for some one-on-one coaching. When I coach someone to help them prepare for a courageous conversation, we generally meet for anywhere from one to six sessions. The number of sessions needed depends on the complexity of the situation and the extent of support they need. I also offer public online training on this topic.

For more information about coaching or to find out when the next workshop is being offered, sign up for my mailing list!