How to have difficult conversations at work? 8 crucial rules

Difficult conversations are an inevitable part of work as a manager. You might need to address a team member’s bad performance, tell a customer that the delivery will be delayed, or give a colleague feedback on how their project is progressing. These discussions are not enjoyable and there might be a temptation to delay them or skip them altogether. But as always in life, it’s necessary to address issues and solve problems before they become too big to solve. How then to prepare for difficult discussions and how to manage them for the best possible outcome?

How to handle difficult conversations at work?

  1. Don’t postpone it for too long. Initiating a conversation doesn’t make sense if you are angry or otherwise very emotional. It is rational to wait for a short while until emotions have calmed down and you are able to discuss the issue constructively. But do not wait for too long. Feedback always works best when it’s topical and everyone remembers the facts. Postponing can also build up anxiety in you and make the issue even bigger in your mind.

  2. When preparing for the discussion, focus on clarifying your goals. The purpose of the discussion should be clear so you can stay focused during the — potentially emotional — conversation. Think about what you want to achieve. You can even write it down. When listing your messages down in advance, try to limit them to three things at most. No one can take in a laundry list of issues. And do not try to script the discussion in advance because you have to have some flexibility and openness to listen to the other person instead of sticking to your well-rehearsed talking points.

  3. Always provide criticism privately. A difficult conversation requires a private space and a peaceful moment when both parties can focus on the discussion. Start by simply asking for permission to talk about something privately: “Hey John, I would like to discuss something about the project. Do you have 15 minutes now?” If John says yes, sit down and have the conversation. If he says no, agree on a better time. It doesn’t make sense to forcefully start the discussion if the colleague is focusing on something else.

  4. Be direct, clear, and confident. It doesn’t help to sugarcoat the problem or hide it among some good feedback. The famous hamburger model, where you place criticism between two compliments, can leave the recipient confused. Tell openly why you want to discuss, what you have observed, and how you believe their behavior impacts you, your team, and the rest of the organization.

  5. Use “I”-statements. As in any conflict resolution, try to start the sentences with “I” to describe how you see, feel and interpret the situation. Don’t start with “you” to avoid making them defensive. Talk about facts: what really happened. Don’t second guess why they did what they did or what that tells about their character. Instead, tell what you have seen and ask why. Don’t say “You don’t seem to care about the project outcome and what we have agreed with the customer.” Instead, say “The customer called me and said they are not happy with the progress. Can you tell me what is going on with the project?”

  6. Ask for their perspective. Listen. Never enter the discussion with the Take it or leave it — attitude. You might hear something that changes your perspective. An open and mutually respectful discussion will help you in solving the problem together and improve your relationship in the long term.

  7. Be empathetic. Don’t play the victim. Don’t say: “It’s very difficult for me to talk about this.” This is not about you. You are not a victim. Acknowledge that you might not understand how the other person feels about the problem or what their perspective is. Ask. Listen. And acknowledge their feelings. Reassure that you care. “John, I can see that hearing this feedback is painful. I understand and I’m sure we can work together to solve the issues.”

  8. Brainstorm together to solve the problem. Suggest solutions. Listen to their suggestions. If you need to take something away from them (a promotion they have requested or even their job), give something back. Depending on the situation this can be e.g. a promise to plan together how they can progress towards the promotion or a recommendation that can help them in landing a new job. When you propose options, you show them alternative ways out and also show that you respect and care for them. After mutually agreeing on an action plan, agree on the next steps and follow up.

Tough conversations are and will be awkward. But when you approach them with fairness and empathy, they can get you what you need instead of ruining your relationships.

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