Sweating over a Difficult Conversation?

Published on 22 April 2026 at 21:32

Does the thought of having  a “difficult” conversation scare you? Do you have sleepless nights over it?  If so, you are not alone.  Nearly all of the clients I have ever worked with dislike this part of their job more than any other.  The unknown as to how the other person will react (or knowing how they will react) results in a lot of procrastination and in many cases, refusal to act. It doesn’t have to be that way.  Here are some of the key points to get you started.

Have confidence in yourself.  You got the role because you had the skills they were looking for, and one of those, presumably, is that you are relational.  If your subject already has a positive opinion of you, you are halfway there.  Having built up positive interactions in the past is important. They will definitely be on the defensive if they think you are on a witch hunt and have ‘got it in’ for them. This makes it difficult to have constructive conversations.  Consider what outcome you want for yourself, for the other person, and for the relationship – always think win/win, not win/lose.  You have to believe that they are capable of changing.  For sure, some behavioural traits seem baked in, but discussing them in the right way can break down barriers and lead to change.

Ultimately the key to a successful meeting is in your preparation.  Preparation involves a number of things.  Firstly, make sure you plan ahead and find a time when you are likely to be calm and will not be interrupted.  Secondly, you need to compile the facts that support your point of view. Not opinions, facts. Start with the least controversial.  Explain what you are beginning to conclude.  Then ask for their perspective.  Agree when you share similar views and compare your two views where you differ.  Where they agree, find out why they are behaving/performing that way.  Always try to find areas of commonality.  Plan a way forward where performance is likely to improve, and keep their mana, and your relationship, in tact.  Monitor for changes and plan for a follow up conversation to discuss progress.

If you want help working through an issue, contact me, it won’t be a difficult conversation :).

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