The difficult conversation: 9 tips for managers

Part of the role of a manager is being able to have the difficult conversation with an employee. This can happen either on the manager's own initiative if there is a need to address the employee's performance, behavior or if there are conflicts that need to be dealt with. The conversation can also take place on the employee's initiative if they need to discuss personal problems or challenges, either at work or in their private life.

It can be challenging, but the difficult conversation is a necessary part of leadership and can be crucial to creating a healthy work environment and achieving positive change. It's about navigating sensitive topics, dealing with resistance and creating a constructive dialog that leads to solutions, happier employees and/or growth.

In this article, we give you practical advice and inspiration on how to prepare and handle the difficult conversation in an effective and respectful way, so you can achieve positive results and maintain good relationships with your employees and colleagues.

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How to handle the difficult conversation before, during and after

Whether you're new to management or an experienced manager with a history of difficult conversations, having a difficult conversation with an employee can be a challenge. Every person and issue is different, and setting yourself up for a difficult conversation requires preparation.

Read our articles on leadership skills and people management.

It can be rewarding for you as a manager to see this type of conversation as redemptive rather than difficult, as it allows you to develop the employee, increase mutual understanding and thereby create better results and well-being in the workplace.

In order to handle the difficult conversation in a respectful and constructive way, it's crucial for a manager to be well prepared. Here are some tips to help you navigate the process and increase the likelihood of a positive outcome:

Below are 9 tips you can use before, during and after a difficult conversation with an employee.

Before the difficult conversation

1. Define your purpose

Before you start the conversation, it's important to clarify the purpose of the meeting. Is it about the employee's performance, behavior, values, bullying or something else? What do you want to achieve with the conversation? Do you want to solve a problem, provide feedback or clarity? Be clear about your purpose so you can steer the conversation in that direction.

2. Prepare thoroughly

Before the interview, it's important to prepare thoroughly. Gather all relevant information and be clear on the factual details. Also think about what questions you want to ask and how best to communicate your observations and concerns.

Remember that:

  • Check if your company has guidelines or policies for difficult conversations that you can lean on.
  • Book a room where you won't be disturbed and set aside time to have a conversation.
  • Invite the employee in question as far in advance as possible and be sure to include information about what the meeting will be about in the meeting invitation.
  • If you work with open calendars, remember the confidentiality of the meeting notice.

During the difficult conversation

3. Create a safe environment

Create a safe and confidential atmosphere where the other party feels respected and heard. Pay attention to your own non-verbal cues and be open. Listen actively, be present in the conversation and make sure you have a physically undisturbed space to conduct the conversation.

4. Be clear and concrete

During the interview, it's important to be clear and specific in your messages. Use specific examples and avoid generalizations. Be mindful of your tone and stick to the facts to avoid misunderstandings.

5. Listen and empathize

An important part of the difficult conversation is the ability to actively listen and empathize. Allow the other party to express their feelings and concerns without interrupting. Show understanding and appreciation for the other person's perspective.

6. Create clear agreements

When the conversation reaches a conclusion, it's crucial to create clear agreements and expectations for the future course of action. Be clear about what steps to take going forward, what the expectations are for both parties and when to follow up. 

During the difficult conversation

7. Take minutes if necessary

If you find it relevant, it can be rewarding for both parties to take minutes to ensure a shared understanding of the conversation and the agreements you've made. 

8. Follow up

Follow up on the agreements and expectations made during the interview and make sure to support the employee along the way if necessary.

9. Evaluate with yourself

It can be a worthwhile exercise to evaluate the conversation with yourself, so you can reflect on what learnings you can take with you for future difficult conversations with employees.

For example, ask yourself the following: 

  • Am I satisfied with the conversation?
  • How did the employee experience the conversation and how did it go?
  • Did I achieve my goal with the conversation?
  • Did I agree something concrete with the employee?
  • Was I told about the consequences if the agreements we made are not fulfilled?
  • Did we have a clear agreement on who does what, when and how?
  • What can I learn from the preparations I made before the interview?
  • What did I do well in the conversation?
  • What can I learn from the conversation?
  • What do I need to work on going forward and how do I do it?

Handling the difficult conversation requires both courage and skill as a leader. By preparing well, creating a safe environment, showing empathy and remembering to follow up, you can strengthen your own leadership skills, create better conditions for your employees' well-being and development and contribute to positive change in your organization.

When your employee comes to you with a sensitive topic

If you have an employee who has come to you with a sensitive topic or issue, either work-related or personal, it's obviously more difficult to prepare for, as you don't necessarily know what to talk about. Here you can keep the above tips in mind and use what makes sense in the situation. 

It's important to meet the employee with understanding and empathy and actively listen to the challenge or issue that's brought up - even if you can't do anything concrete to help. Part of the role of a manager is to meet your employees where they are, and if an employee shows you trust by coming to you with a personal issue, it's your job to take it seriously. 

However, make sure to distinguish between personal and professional content in the conversation. Consider where your own boundaries are, how you as a manager can be supportive or help the employee, and when you should refer them to an HR employee, professional help or something else that can help your employee move forward.

Do you need concrete advice on how to initiate and ask questions during the conversation when an employee comes to you and wants to talk about a sensitive or difficult topic? Below we list some concrete examples of how you can ask appreciative and curious questions without seeming judgmental:

  • You've asked for a conversation, what is it you'd like to discuss with me?
  • I can see that you're getting upset. Can you tell me what's going on with you right now? 
  • How do you experience that...? 
  • Can you help me understand why...?
  • Can I tell you what I'm thinking? I'm thinking that it could also be about... what do you think about that?
  • What do you think would help you? / What has helped in the past?
  • Are there any small steps you can take to move in that direction?
  • Is there anything you think I can do to help you? 
  • I think someone else will be better able to help you because...

Make room for breaks if the employee gets upset. Highlight if you feel the conversation is getting stuck or going in circles and ask the employee to suggest how you can move forward in a way that works for them. 

As a manager, it's not your job to act as a psychologist, therapist or personal counselor - it's a matter of staying in your own lane and knowing your limitations. You can always refer the employee to speak to, for example, the company's HR department, their doctor or health insurance. At the same time, however, it's also necessary to be prepared for these types of difficult conversations so you can handle them as well and professionally as possible, as this also contributes to increased well-being and a good working environment for your employees. 

You can also read more about how to manage the transition from colleague to manager here

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