In coaching session after coaching session, I listen to my clients limit their potential, see only a few alternatives (if any) and project their fears into future events. They “know” what is going to happen. They tell me, “You don’t understand…he will never go for that…it won’t go well…” We role play the conversation and we switch roles. We then look at the situation/issue from all sides and prepare for the different ways that the conversation might go.

In virtually every case, the conversation goes” better than expected.” “You can’t believe what happened!” There is renewed energy, greater optimism, new possibilities. “I at least know where I stand now!”

So, why do we avoid the “difficult” conversations? Why do we accept the status quo when it is in fact unacceptable? Sure, there will be some inherent risks if the other party to the conversation is not willing to engage. It may take a few smaller conversations to lead up to the main event. I wanted to share a few tips from my experience that might help you confront that missing conversation.

1) Set context at the start of the conversation. State why this conversation is important to you and why is it important to have it now.

2) Make sure the setting is suitable for the importance of the conversation. Do everything you can to limit distractions, choose a closed conference room or an off-site location over a cup of coffee.

3) Share not only your thoughts, but also express how you are feeling. How has it been impacting you and your work?

4) Let the other party know that you value the relationship with them. That no matter how difficult the discussion might be, you trust that a fair resolution can be reached, together.

5) Share that it is your intention to give them their fair share of time to be heard. You want to understand their perspective.

6) Be prepared to breathe, especially when you feel that you are about to be triggered by their initial reaction. You want to avoid the “spiral of reactivity.” It won’t help keep the conversation going.

7) Remember to thank them for their openness and for making you feel heard.


My colleague, Michael, always reminds me that FEAR translates into False Expectations Appearing Real. Can you remember a time when the difficult conversation that you finally confronted was worse than what you had anticipated it to be?

Go ahead and have that conversation. The other side will bring you to places that you never imagined.