Difficult workplace conversations
There Is a Conversation You Keep Putting Off
You know it needs to happen. You have rehearsed it in your head more than once. But you keep finding reasons to delay, and the situation is quietly getting worse in the meantime.
Why this keeps getting delayed
You do not want to damage the relationship. You are not sure how they will react. You are worried about saying the wrong thing and making it worse.
Or maybe you have already started the conversation once and it did not go well, so you are hesitant to try again.
In smaller businesses, these situations are particularly difficult because you see the person every day. The professional and the personal are harder to separate.
The longer the conversation is delayed, the more significant it becomes in your mind. And the more the situation has usually drifted in the meantime.
What keeping it on hold usually costs you
- The issue embeds itself and becomes harder to address fairly
- The employee continues the behaviour without understanding the impact
- Other employees wonder why nothing is being done
- You carry the emotional weight of an unresolved situation every working day
- When the conversation eventually happens, it is under worse circumstances with more at stake
- A delayed conversation about performance or conduct can weaken a formal process later
How to prepare properly and get it done
- 1
Be clear about what you are actually trying to achieve
Before the conversation, know what you want the outcome to be. Not just 'saying it', but whether you want a change in behaviour, a shared understanding, a formal record, or something else. The purpose shapes the approach.
- 2
Prepare what you are going to say
Not a script, but a clear set of points. What you have observed, why it matters, what you need to change, and what you want the employee to understand. Preparation is the single biggest factor in how well these conversations go.
- 3
Choose the right time and setting
Private, unrushed, not at the end of a difficult day. Give the employee enough notice that this is a planned conversation, but not so much lead time that they are anxious for days beforehand.
- 4
Allow them to respond
Give the employee the space to explain their perspective. Sometimes this changes the picture. Sometimes it does not. Either way, a conversation where only one party speaks is not a conversation, and it will not hold up if it is later challenged.
Common questions
Questions business owners ask about this
How do I have a difficult conversation with an employee without it going wrong?+
Prepare clearly before the conversation. Know what you need to say, why, and what outcome you want. Keep the conversation focused on observable behaviour or specific facts rather than personality or assumptions. Give the employee the chance to respond. Take notes. Most difficult conversations go wrong because of poor preparation, not the conversation itself.
What if the employee gets upset or emotional during the conversation?+
Pause if needed. Acknowledge that it is a difficult situation. Avoid trying to rush through it or getting defensive. If emotions are very high, it may be worth taking a short break and reconvening. The goal is a conversation that the employee feels was conducted fairly.
Does a difficult conversation have to be formal?+
Not always. Many difficult conversations are best handled informally, especially early in an issue. However, if the conversation relates to disciplinary matters, performance, or a formal grievance, the formality level matters and should be appropriate to the situation.
Should I put the conversation in writing afterwards?+
Yes, in most cases. A brief written summary of what was discussed, any agreements made, and any next steps protects both parties and avoids ambiguity later. Even a short email confirming what was said is better than no record at all.
What if I am worried about saying the wrong thing legally?+
This is a very common concern. Getting advice before the conversation, not just after, is the best way to manage this. Knowing what you can and cannot say in the specific context of the situation gives you confidence and significantly reduces the risk of saying something that creates a new problem.
You might also be dealing with
These situations often come up alongside each other.
Ready when you are
Not sure what to do next?
If this sounds like what you're dealing with, the fastest way to get clarity is the Employee Situation Check.
You deal directly with Samantha. FCIPD Chartered Fellow. 25 years handling situations like this. Reply within one working day.