If you are worried about starting a difficult conversation, sit down and consider your goals in the conversation. Then write out an agenda for how you would like the conversation to go, and a script for how you can best start the conversation to achieve your goals and move into that agenda, recognizing that you might not be able to control how they respond.

When you keep your emotions out of a relationship, you keep a significant part of yourself out of the relationship. If you don’t tell someone when you have been hurt or upset by their behaviour, how can that person know to change their behaviour so as not to hurt your feelings or make you angry in the future? If you pretend that everything is fine, the other person is not getting accurate feedback about the impact of their behaviour on you.

We often think we are sharing our feelings when we are sharing judgments. Saying to someone that they are selfish is not a feeling, it is a judgment. The feeling is that you are being overlooked or under-appreciated, etc.

Too often we confuse being emotional with expressing emotions clearly. Acknowledge their emotions and yours. Seek to understand the emotions. Express the full spectrum of your feelings, not just the surface emotion (which might seem to be anger, for example). Sometimes it is also easier and more productive to have this discussion when you are not both in the grip of the emotions (i.e., the next morning, or an hour later).

It is important to become aware of your identity issues (related to your values or your self-image) so that you can be aware of how they might be triggered. If you find yourself reacting negatively in a conversation, ask yourself whether there are identity issues at play.

When giving feedback, particularly feedback that you think may upset the other person, it may be important to help the other person maintain a balanced sense of themselves. That is, you may want to make an effort to embed your immediate feedback in the larger context of who they are as a person.  For example: “I know you are a very conscientious person who pays a lot of attention to detail in your reports. With respect to this latest report, I would ask that you make the following changes…”

Determine whether your primary goal in exploring the past is to lay blame and prescribe a punishment or to develop understanding and improve the situation in the future. If your goal is to develop understanding, it is important to try to put aside the need to be right. Instead, focus your energies, and those of the other person, on identifying all of the factors that contributed to the present situation.

Build a shared pool of facts before leaping into the deep end of warring conclusions.

Separate the impact of a person’s actions from their intent. We often assume negative intent on their part if the impact is negative to us. If we clarify their intent, we may feel better about them and the situation if we conclude that their intentions were good. Similarly, where we have caused harm, clarifying our intentions to the other person may help them see us more positively than their initial reaction might have suggested.

If you are caught in a difficult conversation by surprise, remember that you may not control what the other person wants or needs to say, but you can control your own response. You can divide a challenging conversation into two parts. Listen and understand their views/issues. Respond later, after giving yourself time to digest and consider your response. If making it a two-part conversation, explain to the other party that you want to give them a full and proper response, and that it would be better for everyone if you took the time to consider it fully.

In any difficult conversation, your first question to yourself should be, “What is my purpose?” Everything you say and do in that conversation should be guided by and consistent with that purpose. If I want my boss to like me and to promote me, proving my boss wrong with spectacularly good facts may be impressive, but it is a poor way to achieve that goal.

If what you are trying when dealing with a challenging person is not working, try something else. Don’t keep beating your head against a wall. Reframe the conversation into a more productive direction. If discussing ideas is turning into an aggressive debate, focus back on the underlying goals of each party. You can more productively work back to ideas later. If having a discussion in public is getting tense, you might take it into a private one-on-one setting.

Before you respond to difficult behaviour by another person, try to understand why they are acting that way. With that analysis in mind, you will be much more effective in thinking about how to respond. If you think they are lying because they were caught unprepared by your questions and didn’t want to look stupid, you might be able to get the truth out by adjourning and giving them time to revisit their answers later.

To learn conflict resolution skills that you can use at work and in your personal life, please visit our Alternative Dispute Resolution Workshop page to learn more about upcoming in-person and instructor-led online sessions.

To improve your negotiation skills and get the results you want while negotiating, please visit our Become a Powerful Negotiator Workshop page to learn more about upcoming in-person and instructor-led online sessions.

To gain skills to handle difficult conversations and difficult people with confidence, please visit our Dealing With Difficult People Workshop page to learn more about upcoming in-person and instructor-led online sessions.