Career
How to Prepare for a Difficult Conversation
The steps to take before engaging in a difficult talk.
Posted August 12, 2020 Reviewed by Ekua Hagan
In a previous post, 10 steps were outlined on how to have a difficult conversation. Before actually having the conversation, a lot of work needs to go into preparing for the conversation. Specifically, you need to determine the reason/purpose to have the conversation, your emotions about the conversation, invite/allow the other person to prepare for the conversation, adapt your style to best suit the conversation's need, and to come into the conversation with optimism. Below each of these steps is discussed in further detail.
What's the reason/purpose to have this conversation?
You need to be super clear on this conversation's purpose because you need to anchor the whole conversation around it. Some examples of purposes could be:
- I want to learn what happened from your perspective.
- I want to give you a chance to express your views/thoughts.
- I want to problem-solve together.
Upon reflection, you may realize that your purpose is to vent/get angry and, therefore, you probably don't actually need to have the conversation. You also don't need the conversation is if the conflict is actually within you (e.g., you recognize that you have control issues and the person went about a task in a different, but equally, valid way).
Once you recognize your purpose, also recognize if there may be a better way to approach it rather than a conversation. For example, maybe you realized it was your mistake and you just need to change your own behaviour going forward. Letting go doesn't mean you no longer care, but it means that a conversation isn't the best way to solve the problem.
Identify what emotions are connected to this conversation or could be triggered in you.

To help ensure you can actively listen during the conversation, you need to be open and vulnerable. And to be open, means you need to know in advance what this conversation truly means to you and what could potentially get triggered.
Understanding your emotions is also about understanding what you feel is at stake you and your self-identity. For instance, are you worried about the perceptions of you from others or are you upset? Or are you upset that outsiders may see your behaviour as potentially being against your values or self-image? For example, you and others perceive you as a "nice guy" but you said something mean. Recognize that any difficult conversation is complex, and your intentions behind it deserve the time to be explored.
Part of understanding your emotions will involve recognizing your contributions. Even if you feel you were "right" you have always contributed to the problem in some way. Some common contributions are ignoring it until it became a larger problem, being unapproachable, switch-tracking (i.e., making the issue about something bigger than what the situation actually was), and making assumptions.
Based on your emotions, begin to reframe them into a constructive conversation. Feelings can easily turn into judgments "you should have been there for me," blame "you were trying to hurt me," characterizations "you are always inconsiderate," and trying to over-control "the answer is for you to call me." Recognizing these emotions will help you avoid these pitfalls and potential triggers.
Invite the person to have a conversation based on that purpose.
Both you and the other person need to have a sense of what this whole conversation's purpose is and what it means to you. This is essential to have a constructive dialogue.
Inviting the person means you cannot do "hit and runs" where you get to state your feelings and the impact before they have a chance to collect their thoughts. "Hit and runs" will likely result in defensive or impulsive reactions and not meaningful conversation.
When you do invite the person, ask for a discussion based on your purpose but don't impose. They may not want to have a conversation. However, if you state, "Hey, I felt that the project didn't go as well as I wanted and I wanted to get your thoughts as well as discuss mine about what we could have done better" allows them to recognize that you genuinely want to hear their thoughts as well as prepare them to hear yours. You can be persistent and say, "Does later today work for you? Or perhaps next week?" This type of statement helps you establish the level of urgency while also giving the other person control in how much time they want to prepare.
When scheduling the conversation, allow yourselves to have way more time than you think you need to have this conversation. Allowing for time will demonstrate that you truly want to listen and solve the problem. Better to have extra time than feel rushed or have to restart the conversation later.
Determine the right way to have a conversation with this individual.
This may be the most tricky part of the conversation because it not only requires you to have good self-awareness but also requires that you have the level of emotional intelligence to really know the person you want to have a conversation with.
To consider your own style, how do you usually have conversations? Are you direct? Do you prefer to verbally process? Do you prefer to think before you speak? If you are struggling to understand your style, ask a partner, close colleague, and/or family member.
Then you need to determine what is the other person's preferred style? Is their style and yours compatible, or do you need to adjust to allow them to be more comfortable?
This step is difficult because the conversation is already hard enough, but to then also have to change your style can be daunting and exhausting. If in doubt, finding a balance to ensure you remain authentic is okay.
Assume positive intent.
The last step in preparing for the conversation (but also a step for during the conversation) is to assume you both didn't mean for things to go wrong and you both want to solve the issue.
We tend to assume that if we are hurt that the other person meant to hurt us. However, it's unlikely that a person was intentionally trying to hurt us. Remember it is important to recognize that even if you have the best of intentions, it doesn't mean that you, yourself, still didn't harm or have a bad impact. Accusations are likely to only cause defensiveness. Avoid accusations and if you feel accused of having bad intent, discuss what your true intention was. Really teasing apart impact and intent is a very important step.
Now that you (both) feel prepared to have the conversation, it's time to do it.
References
Stone, D., Patton, B., & Heen, S. (1999). Difficult Conversations: How to Discuss What Matters Most. NY: Penguin Group.