How to Start a Conversation You’re Dreading

How to Start a Conversation You’re Dreading

 by Joel Garfinkle

When you manage people, sooner or later you are in a position where you need to have a conversation that you’d just rather not have.

We’ve all been there – something has gone awry, there’s an interpersonal conflict, someone isn’t performing well or an incident has occurred that can’t go undiscussed. It’s easy to make up excuses or reasons to avoid — it was an isolated incident, the person knows what the problem is, someone else is going to discuss it with them, the already feel bad enough, etc.

It might not be the most enjoyable aspect of leadership, but difficult conversations are part of the job, and possibly one of the areas where we learn the most — about building our team, about ourselves and about human nature in general. If you’re dreading a conversation, take these steps to get you started.

Step 1: Just do it, and do it now

It sounds a bit ridiculous, but it’s true — the best feedback is given as soon as possible after an incident has taken place. The longer you put it off, the more daunting the task will seem. Studies show that employees — especially millennials — actually crave frequent feedback. Even though the conversation you might be difficult, you can make the interaction a constructive experience. Most of us would rather have the opportunity to correct our behavior or make amends. So if you have conflict, confrontation, controversy, disagreement or tension, get yourself set up for success and start having difficult conversations now.

Step 2: Set a time, duration and clear agenda

Before you schedule a meeting, decide on a time limit and consider the location. Determine a reasonable but not onerous period of time to discuss, and decide whether you need to choose a more neutral or private location to talk. Using your office (or theirs) may only increase the tension, or you might have to worry about thin walls and other listening ears.

Ideally, in your meeting agenda, you can convey in your message that you are interested in not just discussing the issue, but hearing their thoughts on the topic and/or how to move forward. Try to set an agenda that clearly indicates their voice will be heard.

Here are some examples:

  • “Dan, I’d like to take 15 minutes to chat about this morning’s status meeting. That was really tense and I’d like to hear your thoughts on how we can have more harmonious meetings. Let’s meet in the cafeteria and discuss over coffee.”
  • “Emily, I’m uncomfortable with the way you spoke to the client on that call. I’ve booked 30 minutes to talk about how we can go about repairing the relationship with them.”

Step 3: Prepare to listen

Regardless of the issue, your first priority in the conversation has to be understanding where the other person is coming from, regardless of your perception or personal bias. Start your conversation with an open-ended question, and actively listen.

Try to continue the discussion with questions that keep the person talking, so you can learn as much as possible from their perspective. Try not to move to on from giving the other person the bulk of the conversation, except to acknowledge and mirror back to them what they’ve conveyed, until you can actively sense that they feel listened to and understood. This could mean that your part of the discussion is going to be relatively short, but that is OK.

Finally, when it is your turn to talk, try to stick to “I” statements — use your opportunity to talk to validate their point of view, and convey empathy. “You” statements will only put them back on the defensive.

Here are some examples:

  • “I know what it’s like to be totally frustrated by a rude client. It’s hard not to react when you’re being baited. I find that I have to really take my time between statements to avoid reacting.”
  • “I would have been happy to help you prepare for the meeting if I’d known you were overloaded.”

End your conversation with asking more questions, and coming to some agreements — what will the person do next? How can you support them and help them succeed? How and when will you follow up? And how will you both know when the issue is resolved? Just like this initial conversation, plan for that follow-up, and resist the urge to put it off; have it in a timely fashion.

By preparing and having difficult conversations, you also improve your communication skills.



Well-timed silence hath more eloquence than speech.

~ Martin Fraquhar Tupper


Published October 17, 2016 in SmartBrief.  Joel Garfinkle is the author of nine books, including “Difficult Conversations: Practical Tactics for Crucial Communication” and “Getting Ahead: Three Steps to Take Your Career to the Next Level.” 

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