How To Handle Difficult Conversations At Work

Pro tips for courageous conversations

Difficult conversations
How to handle difficult conversations at work

As a small business owner or boss, you’re going to be faced with difficult situations that require a difficult conversation. That’s why you’ll probably be keen for some pro tips for courageous conversations.

The hard truth is that if we avoid or delay when we need to have a courageous conversation, we get stuck with problems and challenges we don’t want. The kinds of problems, challenges and frustrations that are emotionally, physically and psychologically draining.

You know what I mean, right? – energy vampires.

How to handle difficult conversations at work so they don't become an energy vampire.
Avoiding difficult conversations will suck the energy right out of you.

There are many examples of courageous conversations. You may have to discuss poor performance, or spending too much time around the water cooler. You may have to discipline someone you like for using the photocopier to take pictures of a body part and sending the picture to their mate 😳.

The reality is, having a difficult conversation can be tough on you, and them – but it is necessary.

So, here are some essential steps of courageous conversations that will allow you to handle difficult conversations at work.

Ask for Permission

Create a safe environment for you and your employee by asking them for permission.

Mention “I have some questions and concerns I’d like to discuss with you. When would be the best time to talk?”.

This question demonstrates that the conversation is a two way street. Your team member will feel more valued, and it’ll make you seem less like the bad guy. It can get that difficult conversation off to a positive start.

Ask permission for a difficult conversation.
Ask permission to get a difficult conversation off to a great start,

Be Clear About Your Objective

Be clear on what you’re wanting to achieve with this conversation. What is the change that you want to see? What is the desired outcome?

Here’s an example – Steve photocopied his body parts and sent them to one of his mates at another branch. You want Steve to think before he acts in the future. He does stupid stuff like this all the time without considering how his actions affect others, and what the potential impact or consequences of his actions might be.

Clear direction for difficult conversation
Make sure you have a clear intent and direction for your difficult conversation.

Step Into Their Shoes

Part of being courageous when you’re faced with a tough conversation is accepting that there is almost always two sides to any story. Do your best to step into their shoes. If you behaved in the same way, would you think your actions were appropriate?

Seek their perspective. Once you’ve introduced what the issue or situation is that you’re wanting to talk about – ASK for their point of view. If your employee knows you’ve looked at the situation from their point of view, they may not automatically see you as the enemy.

Understanding their perspective may help you to deliver your conversation calmly, and may affect the direction you want to take the conversation.

You may discover that the person lacks a skill that they need, and requires training. Or maybe they’re having a particularly tough time at home, and aren’t themselves at the moment. Is there something you can offer or do that might help?

Or maybe, they’re just behaving like a moron, and there is no excuse.

Stepping into their shoes for difficult conversation
Do what you can to step into their shoes before and during a difficult conversation.

Keep It Factual And Calm

Make a list of what happened (Steve photocopied his…hand… and sent the picture to his mate).

Keep it factual and take some responsibility for the part you played in the situation. For example, if you’ve done something similar – your actions will have sent a message that this kind of behaviour is OK.

Sticking to the facts will help you to stay calm. Shouting is rarely effective. It makes the walls go up; and results in an argument, defiance, or a “talk to the hand” kind of moment.

Difficult conversation
How to have a difficult conversation without being ignored

Show That You Care

Showing that you care will mean that you’re more likely to be heard, and you’re less likely to need to have these difficult conversations in the first place.

It can be tough to show that you care when you feel like you’re dealing with the same old BS, and that you have another 100 things that you need to be doing.

Caution… don’t mistake showing that you care, with weakness. If you need something to change… it must change. Be firm and follow up.

Show that you care when having a difficult conversation.
Show that you care when having a difficult conversation.


So, there you have it. Some essential steps of courageous conversation that will help you handle difficult conversations at work.

  1. Ask for permission
  2. Be clear about your objective
  3. Step into their shoes
  4. Keep it factual and calm
  5. Show that you care

In the long run, avoiding or delaying difficult conversations will cost you more pain and suffering than the conversation will – so go ahead – have that conversation. If you don’t, you are denying both you and the team member the opportunity for improvement.

What courageous conversation do you need to have?


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