Difficult Conversations: Before the Talk

Updated: May 10

Having difficult conversations is not easy but half of the work is preparing for the conversation. This post talks about tips and tricks on handling difficult conversations.




I have had to have so many of these conversations over the course of my career and each and every time, I still have a knot in my stomach. But I have the conversation anyway. My journey with difficult conversations took a structured turn a few years back when I was in a situation where someone in a professional setting said an inappropriate joke, yet the person was oblivious to the impact of what they had said. I had to decide; to let it go or to have the conversation.


In the moment I was flustered (although I don’t think I showed it), I had heat rising to my ears, and I was quite simply furious. I debated in my mind whether or not to have a conversation with the person about this situation and then decided I would.


Why do you want to have the conversation?


Before I decided to speak with the person, I tried to understand why I was so upset. After getting to my third “Why” (which is a technique that helps you find root cause), I realized his statement was simply rude and I didn’t appreciate being spoken to like that.


What will happen if you don’t have the conversation?


I asked myself if this conversation was necessary, will it solve for why i want to have the conversation above. I concluded it was absolutely important to have this discussion. I also imagined him, unaware of the impact of the way he spoke, doing it again. I couldn’t trust my reaction if it happened again and I didn’t want it to come to that. So I decided yes, I do need to have this conversation.


What is the message you want to send across?


I had to decide what message I wanted to send across ahead of the conversation. Was the conversation to vent? No. Was the conversation to communicate what I find acceptable and unacceptable, and how I considered his statements rude and offensive though he may not have meant it that way? Yes. Was the discussion to prevent another situation from happening without due warning? Yes.


How will this discussion impact my relationship with this person?


In this instance, he and I didn’t work too closely together so this was kind of easy. I merely asked to speak with him in private and told him how I didn’t appreciate his comments and how I found them offensive. He apologized profusely. At least, he never did it again, to our mutual benefit.


Down the line, I faced situations where I had to have difficult discussions with team leads and managers reporting to me, and in unique situations, my boss. Imagine giving your boss feedback?


Depending on the person, considering how hierarchical certain professional structures in certain organizations can be, each conversation was handled differently.


It is important to consider first if the conversation is worth having. When you do - you then decide exactly how you will handle the discussion.


Continue this post here During The Talk

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