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How to prepare for a difficult conversation at work

You need to raise something with a colleague, a manager or someone you lead. Perhaps an agreement fell through, or working together has become strained. Before you meet, you can explore what happened, how you reacted and what you want to achieve.

A woman in a striped shirt speaks with a colleague in an office.
Illustration photo: zamrznutitonovi / Envato

This preparation draws on Jan Petrus Hagberg’s SGL method and its advice on separating messages, speaking from your own experience and asking open questions. Write a few notes as you read.

Decide what you want to achieve

Choose one situation to focus on. What do you need to understand or clarify so that you can keep working together?

Here is an illustrative example: you and a colleague agreed on a handover at 10 am on Friday. You received the material at 2 pm and had to change your plan. You want a more predictable way to handle handovers.

Set your aim before planning your arguments. In this example, it could be: “We need to agree what to do when a deadline is likely to slip.” That gives the conversation a clear direction and room for both people’s experiences.

Separate facts, feelings and interpretations

SGL’s advice on active listening emphasises separating different kinds of messages. Use three headings in your notes:

  • Facts: What did you see or hear? In the example: “We agreed on 10 am. The material arrived at 2 pm.” Include specific events you can explore together.
  • Feelings: What did you feel? “I felt anxious as time passed, and frustrated when I had to change the plan.” Put your own reaction into words.
  • Interpretations: What meaning did you give the event? “I thought my part of the work had been given a lower priority.” That thought tells you something about how you experienced the situation. You still need to hear the other person’s perspective.

This helps you express yourself clearly while keeping your questions open. You can also explore your own contribution: was the deadline clear? Did your colleague have the information they needed? What had you explained about the effect of a delay?

Prepare an opening in your own voice

Write a few sentences describing the event, your experience and what you want to clarify. One possible opening for the example is:

“We agreed on a handover at 10 am on Friday, and I received the material at 2 pm. I felt anxious because I needed it to move forward. I’d like us to find a way to let each other know when plans change. How did you experience the handover?”

Use words that feel natural to you. Arrange a time when you can talk without interruptions, and explain the topic beforehand. That gives the other person a chance to prepare too.

Make room for the answer

Open questions beginning with “what” and “how” are central to SGL’s communication advice. Choose a couple of questions you really want answered:

  • How did the situation look from your side?
  • What was unclear in our agreement?
  • What do we need from each other next time?

Listen to the answer before moving to the next question. You can check your understanding by saying: “Have I understood you correctly when …?” The answer may give you a reason to revise your interpretation. You can also be clear about what you need to do your work.

Plan the agreement and follow up

Think about a specific next step you would like to suggest. In the example, you could agree to flag an uncertain deadline as soon as possible and work out a revised plan together.

Before you finish, summarise who will do what and when you will follow up. After the next handover, you can discuss whether the agreement worked and what needs adjusting.

Take your preparation into the conversation

Read through your notes once more. Is the event specific? Have you put your own reaction into words? Is there something in your interpretation you want to explore? Do you know what you want to suggest?

In SGL Coach, you can bring the situation to the AI agent and explore it before you meet. Afterwards, you can reflect on what happened and choose what to do next. You learn the other person’s perspective through the conversation with them.

Explore how SGL Coach Personal can support you.