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A Guide to Difficult Feedback Conversations


We all have experienced those difficult “we-need-to-talk” conversations in the workplace. Conversations about underperformance or sensitive matter are never easy (for both the manager and employee). Below we list some tips on how to approach these difficult conversations.

Before the feedback conversation

1) Prepare for the conversation

First and foremost, managers will need to prepare for the conversation with their direct report. It can be helpful to go through the following questions before the meeting.

  • What is purpose of the conversation?
  • What do you hope to accomplish?
  • What is the ideal outcome?
  • What might the other person be thinking about this situation?
  • Is the other person aware of the problem/issue?
  • Have you contributed to this problem/issue in any way (ex. could you have addressed this issue previously but didn’t? Did you provide sufficient training to avoid this type of issue before)?

2) Bring supporting documents if needed

In general, past feedback should be made available to employees during their tenure at an organization – past feedback acts as a good reminder of their performance, but it also helps show progress. If you are referencing past performance/projects, it can be helpful to review these documents before any feedback conversation. It can also be helpful to have these documents handy in case you need to reference them during the conversation.

During the feedback conversation

1) Ask open ended questions

Open-ended questions are a perfect way to gain insight into an employee’s performance, work habits, and skill set. Moreover, these types of questions help you build a relationship with your employee and understand their perspective and help build a culture of feedback in your organization.

Some ways to begin the conversation include:

  • I’d like to talk about ____________ with you, but first I’d like to get your perspective.
  • I’d like to talk about ___________________. I think we may have different opinions/perceptions about ____________________.

Other questions to ask during the conversation:

  • What is in your way? What is stopping you?
  • How do you feel?
  • What is something I can do to support you? What do you expect of me (as your manager)? What should I do differently?
  • Are expectations and goals clear?
  • Do you have any questions for me? How can I help?

For more questions, check out our guidebook with 100+ review questions.

2) Be transparent

Direct and kind is the best way to give feedback. If you think an employee has been underperforming, do not sugarcoat the feedback. Take the time to explain the situation, your perception & your expectations, and give the employee a chance to ask questions & reply. Acknowledge them and actively listen to your employees’ concerns.

Pro tip: 65% of communication is conveyed via non-verbal cues. Be aware of your tone of voice, body language, and gestures when you have tough conversations.

3) Keep an open mind

We know a fraction of what employees may be experiencing. Managers need to remember that empathy is key during feedback conversations. Actively listening to concerns and kindly responding to questions and comments can help managers show they care about their team.

After the feedback conversation

1) Document the conversation

From a risk mitigation angle, documenting feedback conversations provides evidence that issues were addressed. It also offers a history of the performance of the employee. There should be a standard way to document both praise and constructive feedback in every organization. These tools can include pen-and-paper, Google sheets, or simple feedback softwares (check out Pavestep’s continuous feedback software).

As mentioned earlier, it is helpful that the employee has access to the feedback – often when difficult or bad news is given, important details of a conversation can be missed and forgotten. Employees may want to reread or reference the feedback after they have had a chance to digest it. Past feedback also acts as a benchmark that employees can use to improve their performance, so having it visible to them is important.

2) Follow-up

Whether it is in the form of a performance check-in or a casual coffee outing, make sure to follow-up with the employee to support, encourage, and build a relationship with them. If the conversation involves a lay-off, remember that you can still keep in contact with the employee. There is value in keeping in contact with previous employees, particularly if they are hard working. If you want to know more about why you should keep in contact with them, check out our previous article on the importance of alumni groups.


There is a value in maintaining a relationship with your [ex-employees]. Leaving is inevitable and these people should remain as part of the community.” – James Sinclair, WWP podcast


Have any thoughts on this topic? Feel free to reach out!

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