Seven Questions to Ask Yourself Before You have a Difficult Conversation

Tough conversations. You know, the ones we need to have, but are concerned about. The ones that remind us of the similar conversations that didn’t go so well in the past.

Popular books have been written about these types of conversations, and have changed what we call them. Now many call them crucial conversations or fierce conversations. Call them whatever you want, they are hard.

And, as a leader, they are often necessary.

Perhaps as a leader we find ourselves needing to have them more often due to the nature of our job. And perhaps, sometimes you put them off because they are hard; but you also likely know from experience that avoidance isn’t a good strategy either.

I have eight questions (yes, there are eight, not just seven as promised) for you to ask as a part of your preparation for these difficult conversations. These questions will challenge you to think in new ways about the situation and your preparation for it. They will point you to a mindset that might change your whole approach to difficult conversations too.

What is your goal? Determine the outcome that you hope for from this conversation.

Am I in the right frame of mind to discuss this now? If you know you aren’t, wait, but don’t wait forever. If you must discuss it now, change your mindset first!

What are some options to solve this problem? There is always more than one way. Make sure you have options in mind going into the conversation.

What information do I or we need? Sometimes the right information will make all the difference in the world in creating better outcomes.

What role did my behavior play in this situation? This is always an important question, but as a leader it is critical.

How do you think they view the problem? This question puts you in the mind of the other person. You may not know the answer, but thinking about it first will make you far better prepared for a successful conversation.

Am I ready to apologize or take responsibility? (and for what?) Well, are you? If not, the conversation may be harder than you are even speculating.

How can I contribute to a better outcome? If you have answered the first seven questions, you likely have some ideas here. Don’t go into a difficult conversation without an answer to this one.

Perhaps you hoped that these questions would magically make difficult conversations easier – they will not.

But they can be magical. If you take the time to ask yourself these questions, and answer them, you will be better prepared and it is very likely that while the conversations might not be easier, they will arrive at far better outcomes.