Having That Tough Conversation

Have you ever had to terminate someone’s employment or end a business relationship with a partner or a supplier? If ‘Yes’ is your answer, then you will no doubt agree that it is not an easy thing to do. So much so in fact, that we often allow such situations to continue to fester for a long time because we are afraid to tackle them.

Why are these situations so difficult?

I think it can be for two reasons:

1. Unless you are completely devoid of humanity, you cannot help but be compassionate towards the person that you need to have the tough conversation with.

2. We make up stories about how ‘we think’ the other person is likely to react and what they will do. The resulting feeling of guilt, remorse or fear of consequences are what ultimately lead us to putting the issue ‘on the long finger’, in many cases with the hope that something happens to make them leave or take action of their own accord.

I am sure you have seen it yourself, a business being hamstrung by a staff member whose quality of work is poor, or a business partner who is not pulling their weight or even pulling in the opposite direction and the enterprise is suffering.

It is a very common problem. I have seen many situations limping on for years, slowly dragging the business down until either someone finally cracks and takes action or else something is discovered or an incident occurs which then blows up – the result is never pretty or cheap to resolve.

What is there to do?

If you are stuck in such a situation or indeed anything involving a difficult conversation, there are a few things to do:

1. Get it out of your head – Most stories get their energy from just swirling around in our heads unchallenged. Write down your reasons for not taking action and see if they are valid or rational.

2. Impact List – Write down all of the things which are negatively impacted by allowing the situation to continue. Can you afford to let it go on?

If the answers to 1 and 2 take you to a place when you need to have that tough conversation, then move to the next steps below:

3. Write down everything that you need to say to the person, from a place of compassion. It should explain that the relationship is not working for you and it might include an explanation of ‘why’, which might offer guidance to the other party for the future.


It is not necessary to have exit arrangements such as legal and/or financial matters resolved at that point (although you might have taken prior advice). The main purpose of the conversation is to communicate your decision – this converts inertia into action.

Dealing with the facts of a situation

The thing to keep in mind throughout the process is that whilst you might try to imagine how the other person will react, the reality is that you don’t know what will happen. Yes, they might be upset, but equally they might jump up and hug you because they might have been unhappy and afraid to ‘let you down’ by leaving!

You can only deal with the facts of the situation and what is actually in front of you. You cannot deal with made-up stories about impact and consequences because they are just a fabrication of your imagination. Being real, dealing with facts and acting compassionately is the very best that you can do every time!

Photo by Nik Shuliahin on Unsplash