Before a Difficult Conversation, Ask Whether You Need to Have It at All

Most people have a conversation they keep putting off. It might be with a coworker or a client, or with a relative who is about to hear something they won’t love.

Penn State Extension has a practical guide for the part that happens before anyone says a word: the preparing. The article was last updated March 9, 2023. It is general best-practice advice, not a study, so it promises no particular result. It does offer a sensible order of operations for a talk you are dreading.¹

The guide starts by explaining why these talks are hard. The main reason, it says, is that people bring different backgrounds, experiences, values and concerns to the table.¹ It borrows a definition from Stone, Patton and Heen’s 2010 book on the subject: a difficult conversation is “anything you find it hard to talk about.”¹ That definition is broad enough to cover a contract dispute and the question of who keeps eating your yogurt in the office fridge.

The advice leans toward work situations, with its talk of clients, coworkers and organizational policies, but most of the steps carry over to home. Here is the prep list, with matching advice from two other universities.

The prep list

1. Notice how you usually talk. Ask yourself whether you tend to speak more positively or negatively about your work, and ask people you trust for honest feedback. If you lean negative, the guide suggests going into hard conversations with a deliberately optimistic attitude. This step is written mostly with work talk in mind.¹

2. Decide whether the conversation needs to happen. Is the conflict internal (something you are wrestling with yourself) or external (something between you and someone else)? Can you actually change anything by talking? Would the talk damage a relationship for no good reason?¹

3. Gather what you need to know. If you decide to go ahead, the guide says to collect all the information you need first.¹

4. Know what you are hoping for. Decide what results you expect from the conversation.¹ University of Utah training guidance makes the same point: understand your own thoughts and the outcome you want, and also think about how the other person sees things.²

5. Tell the other person what it is about. Penn State’s guide advises letting them know the purpose of the conversation.¹ University of Colorado Boulder health guidance agrees and suggests explaining why you want to talk and what you hope will come of it.³ Nobody does their best listening while wondering why they were summoned.

6. Pick the place and time carefully. Penn State recommends a neutral location, plus a facilitator if the situation calls for one.¹ Utah’s guidance suggests a private, quiet spot without interruptions,² and Colorado’s advises a private area at a time that works for both people.³

7. At work, check the rules. If the conversation involves your job, review any organizational policies that apply before you sit down.¹

Keeping expectations realistic

The guide is candid about one thing: it is unrealistic to expect every conversation with clients, coworkers, family and friends to go well.¹ Preparing won’t make a hard talk easy. It can give you a clearer idea of why you are having it and what you hope will happen, and that is a reasonable place to start this week.