difficult conversations with direct reports

Difficult conversations are part of life (and work). When you are managing the work and careers of others, you will inevitably have to tackle a difficult conversation topic, like negative performance feedback or personality issues, with the people who work for you. If you are nervous when you have these kinds of conversations, your intention to help your direct reports grow and improve can help you maintain composure. Like any other skill, having difficult conversations becomes easier the more often you have to do it. But hopefully, you won’t have to have these conversations very often with the people who work for you.

The topic of having difficult conversations with direct reports pulls directly from previous posts about managing others and workplace courage. When we talk about “direct reports,” this refers to the people who work for you or report to you, whether formally or informally. Direct reports make up the team under your charge. You are managing and responsible for the work, the careers, and the success of your team.

Given enough time in a leadership position, you will have to eventually address a difficult topic with a direct report. The individuals who work for you will make mistakes and there will be personality issues. That is simply the reality of working with human beings. 

Examples of needing to confront someone who works for you could include: 

• They are not performing up to expectations on a consistent basis (tardiness to work or meetings, quality lacking on assignments, not completing assignments, etc.)
• They committed a one-time error that caused harm to the business 
• There is a personality issue or working style that has caused conflict with a third party

These are just a few examples and you can probably think of a few more that you have committed yourself.  Nobody is perfect. Your role as a leader is to help your team succeed and learn from their mistakes.

Radical Candor by Kim Scott is an excellent resource to supplement this subject. This book provides advice on how to be both empathetic and straightforward with others. Like all advice books or blogs (including this one) your personal experience and work situation is nuanced and how you apply the advice will be nuanced too. 

When you need to confront a direct report with a negative or difficult topic, there are a few things to keep in mind to help the encounter go smoothly for both you and the person you are addressing. What people fear most about confrontation like this is the reaction of the recipient of the information. It is true that they may have a negative reaction to what you are saying to them. However, if you fear this, you might only be worried about protecting yourself. As their manager, you need to acknowledge that addressing the topic with them will ultimately help them out. If you keep a problem-solving and performance development mindset, it will assist you through the conversation.

Choose your timing. Schedule the conversation and address the issue as soon as you can, do not put it off. The longer you wait, the less you are helping your direct report. Schedule time at the end of the day and at the beginning of the week with them. If it’s a virtual meeting, use video to gauge their reaction and allow them to see yours. If the meeting is in person, have it privately out of respect for the person you are addressing. (As a note, you can enlist the help of someone else to sit in on the meeting if you feel there needs to be a neutral third party present for any reason.)

Be clear and honest. The person you’re speaking to might already know about the situation you are talking to them about, or they might not. Regardless, there is no need to provide a “compliment sandwich” – address the topic you came here to address. It’s best to be clear and succinct about the situation you are describing – stick to facts. A good rule here is to explain your expectations about what should have happened, what actually happened, and the disconnect. 

You might receive pushback at any point in the conversation from the individual you are addressing. Allow them to vent if needed, and hear them out. But stick to your points and what you planned to say. If you start to get flustered, take a deep breath and remember you are providing help and support by having this conversation.

Recommend improvement. After explaining the situation, provide actions for improvement. This might include solving a one-time problem or providing a performance improvement plan for a longer-standing issue. Make sure the feedback is actionable and also includes a timeline. 

Follow up. Monitor and measure the outcome of the conversation. Provide email follow-up to the direct report documenting the actionable feedback you discussed, and check-in with them afterwards on their progress. Keep written record of every conversation like this one that you have with them. If there is no improvement on the matter, you may need to have additional conversations with them. Any documentation you have will help you if you need to eventually let them go. Letting someone go would be difficult but they will ultimately be pushed to find a better-fitting role for themselves.

Some additional thoughts: Consider building an “in-time” performance mindset into your management style. Giving feedback while an event is happening or immediately after will prevent performance issues from building up, or bad habits from impacting work. Sometimes this can prevent the need to have difficult conversations about performance because small issues aren’t given the opportunity to accumulate into bigger ones.

Having a tough conversation with a direct report is not easy. By being timely, honest, and clear, providing actionable feedback, and following up, the process can be easier for you and productive for them.