Executive Therapy

Difficult conversations are necessary in life, in love, and most certainly in business. 

  Whether it is your significant other that you need to talk to or perhaps a direct report there are a few things that you can do to take a difficult conversation that’s approaching and set it up for success. 

Strategy number 1: When possible, give the other party topic of the conversation and let them know, “hey tomorrow I’d like to talk to you about the_____.” Giving them the agenda or the topic at hand ahead of time allows them to possibly prepare some meaningful thoughts on that subject and more importantly, they are less likely to feel ambushed by the conversation. 

Now, when we feel ambushed and the conversation is difficult or emotionally intense we are likely to flood which means we go into a fight, flight, or freeze stage and we lose our ability to problem-solve effectively. This conversation is going to be a lot more effective if you’re able to prevent that from happening. 

On the day of the difficult conversation, strategy number 2 is to spend a few minutes and chit-chat, building some rapport and connecting with them first. Even if you don’t normally do this, insert just a few minutes before you dive into the topic at hand. 

Then, strategy number 3, predict the problem. If this individual has become defensive with you on multiple occasions in the past, you can begin the conversation with something like “I know that what I’m about to share may be difficult for you to hear but I’m going to ask that you refrain from becoming defensive.” When we predict the problem we insert the possibility that that person will curtail that unwanted reaction we’ve gotten from them before. 

Strategy number 4, let them know what your positive intention is. “My hope is that we can hash this through today and then put this topic to bed.” or “My hope is that we can find a common middle-ground.” Then, state your case.

Finally, strategy number 5, stay on topic. When a conversation is difficult and it’s emotionally beleaguering because of the taxing nature of it it’s important that you get in and get out and do not allow the conversation to stray off-topic or allow it to elongate for too long. It’s better to bring your best self to the conversation than to stay in it for too long.

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