A team member has missed another deadline.
You know you need to speak with them, but the conversation keeps getting pushed to tomorrow.
Perhaps you are worried they will become defensive. Maybe the employee is normally a strong performer and you do not want to damage the relationship. In some cases, managers simply have no idea how to begin the conversation.
So, nothing is said.
This is where a small workplace problem can slowly become a much bigger one.
Knowing how to have difficult conversations with employees is part of being a manager. These discussions may involve poor performance, repeated lateness, inappropriate behaviour, conflict between colleagues, or an employee who is not meeting expectations.
The aim is not to make every difficult conversation comfortable. That may not be possible. The aim is to address the problem clearly, hear the employee's side, and decide what should happen next.
Why Do Managers Avoid Difficult Conversations?
Most managers know when something is wrong. Addressing it is the harder part.
A manager may worry about upsetting the employee or damaging team morale. New managers, in particular, can find these situations uncomfortable when they have recently moved from being a colleague to managing the same team.
There is also the fear of a bad reaction.
What if the employee becomes angry? What if they deny everything? What if the conversation becomes emotional?
Avoiding the issue may feel easier at the moment, but the problem usually remains.
Imagine one employee regularly arriving 20 minutes late. The manager notices but says nothing. Other employees begin to notice too. Eventually, someone asks why they are expected to arrive on time when the same rule apparently does not apply to everyone.
The manager is no longer dealing with one employee's lateness. The issue has started affecting the wider team.
Difficult conversations are often easier when they happen before frustration has had time to build. Making this possible shows the difference between a manager and a leader.
How to Have Difficult Conversations With Employees
1. Know Exactly What You Need to Discuss
Do not begin a difficult conversation with a vague feeling that an employee is “not doing well.”
What is the actual problem?
Perhaps three deadlines were missed in the last month. Maybe a client complained about an interaction. An employee may have repeatedly interrupted colleagues during team meetings.
Identify the issue before arranging the conversation.
For example:
Vague concern: “His attitude has changed.”
Specific concern: “During the last three team meetings, he dismissed two colleagues' suggestions and left one meeting before it ended.”
The second version gives the manager something real to discuss.
This preparation is particularly important when emotions are involved. A manager who enters a meeting already frustrated can easily move from discussing one problem to listing every mistake an employee has made over the past year.
Stay with the issue that needs attention.
2. Do Not Start With a Threat
The opening few sentences can shape the entire conversation.
Consider this opening:
“We need to talk. I've had enough of what has been happening.”
The employee is likely to become defensive before the manager has even explained the problem.
A calmer opening can be direct without immediately turning the discussion into a confrontation.
For example:
“I want to discuss the last three project deadlines. They were all missed, and I need to understand what is causing the delays.”
The problem is clear.
The manager has not hidden the issue, but the employee has also been given an opportunity to explain.
A real example comes from Kim Scott and Sheryl Sandberg. After Scott gave a presentation at Google, Sandberg pointed out that she was repeatedly saying “um” while speaking. Scott initially dismissed the issue. Sandberg became more direct and explained that the habit was affecting how intelligent Scott sounded to her audience. Scott later described this experience as an important example of caring personally while challenging someone directly.
Managers sometimes believe they need to sound angry to show that a matter is serious. They do not.
Clear words can communicate seriousness without raised voices.
3. Use Facts Before Assumptions
An employee has stopped contributing during meetings.
The manager thinks, She no longer cares about the team.
That is an assumption.
What the manager actually knows is that the employee has spoken less during the last four meetings.
There could be several reasons for the change. The employee may disagree with the direction of a project. They may feel that their suggestions are regularly ignored. There may also be an issue the manager has not noticed.
Start with what you can observe.
You could say:
“I've noticed you've been much quieter in our recent team meetings. You used to contribute regularly, so I wanted to check if something has changed.”
Compare this with:
“You don't seem interested in the team anymore.”
One starts a discussion. The other tells the employee what the manager has already decided about them.
Facts give difficult workplace conversations a better starting point.
4. Ask the Employee to Explain Their Side
Managers do not always have the complete picture.
Suppose an employee has missed two deadlines. The manager assumes the person is disorganised.
During the conversation, the employee explains that another team has been sending essential data several days late.
The missed deadlines still need to be addressed. However, the problem may be different from what the manager first believed.
Ask questions such as:
“Can you talk me through what happened?”
“Is there something affecting your ability to complete this on time?”
“How do you see the situation?”
Then give the employee time to answer.
Listening does not mean automatically accepting every explanation. An employee may make excuses or disagree with the manager's concerns.
The purpose is to make a decision after hearing the relevant information rather than before.
5. Do Not Turn the Conversation Into a List of Past Mistakes
Once a difficult conversation begins, it can be tempting to bring up everything.
The missed deadline from last month.
The email that annoyed a client six months ago.
That disagreement during a meeting last year.
Soon, the employee has no idea which problem the conversation is actually about.
If previous issues are directly connected to a repeated pattern, they may be relevant. But managers should be careful about using a current concern as an opportunity to unload months of frustration.
Imagine telling an employee:
“This is just like the problem we had in January, and you were difficult during the Anderson project, and I still remember what happened at last year's meeting.”
At that point, the conversation has lost focus.
Address problems when they happen.
If the current discussion is about missed deadlines, discuss the deadlines, the reason for them, and what needs to change.
6. Be Clear About What Happens Next
A difficult conversation should not end with:
“Anyway, just try to do better.”
What does “better” mean?
An employee needs to understand the next step.
If the problem is lateness, clarify the expected arrival time. If project updates are not being communicated, explain when updates should be provided. If there is a performance concern, identify what improvement should look like.
For example:
“From this week, I need the project status report by 3 p.m. every Friday. If you expect a delay, tell me before Friday rather than after the deadline.”
That is measurable.
Both the manager and employee know what has been agreed.
If the conversation specifically involves work performance, our guide on how to give constructive feedback to employees explains how to keep feedback focused on actions and improvement.
7. Follow Up Instead of Pretending the Conversation Never Happened
Difficult conversations can feel awkward for managers too.
After the meeting, there may be a temptation to avoid the subject and return to normal.
But follow-up matters.
Suppose a manager speaks to an employee about poor communication with clients. Three weeks later, the employee has made a noticeable improvement.
Say something.
“I've noticed the client updates have been much clearer this month. The change is helping the project.”
A difficult conversation should not follow an employee forever when they have addressed the problem.
On the other hand, if nothing changes, the manager also needs to follow up.
Ignoring the continued problem sends a confusing message. The employee may assume the original conversation was not particularly important.
You can also read our article on how to give constructive feedback to have a better understanding of presenting feedback to employees to make them more efficient.
Frequently Asked Questions
How do you give negative feedback without demotivating someone?
Focus on specific behaviour rather than the person's character. Explain the problem clearly and discuss what the employee can do next.
What is an example of negative feedback to an employee?
Instead of saying, “You are careless,” say, “There were three errors in the report that need to be checked before the next submission.”
How do you politely give negative feedback?
Be direct, calm, and specific. Discuss the issue privately and avoid insulting or labelling the employee.
What should a manager avoid when giving feedback?
Managers should avoid public criticism, vague comments, personal attacks, and waiting too long before addressing a problem.
Is the feedback sandwich effective?
It can be useful in some situations, but overusing it may make feedback unclear and cause employees to become suspicious of positive comments.
