Handling Difficult Conversations: 11 Questions to Ask Yourself

Erika Petrelli
Erika Petrelli

A decade or so ago, while managing a team of individuals who were each responsible for managing teams of their own, I noticed that many of them (myself included, on occasion) struggled with when and how to have difficult conversations with their staff. Three scenarios kept showing up: 1. people avoided difficult conversations altogether; 2. they “ambushed” their staff member with a difficult conversation out of the blue; 3. they entered a difficult conversation without any clear forethought about what their intended outcome was. Since I suffered from all of these as well, I tried to think of a way to help us all get better at having respectful, healthy, and productive conversations—even, and especially, when they were difficult. 

After tinkering around with a few ideas, I came up with the “Difficult Conversations Wheel.”

The wheel is designed to be prepare for the difficult conversation, and should be done prior. The hope is that by thinking through these questions in advance, you’re setting yourself up for a more productive and successful conversation, and we found that those that embraced the wheel and thought through its questions before entering into a difficult conversation reported that the conversations were usually so much better than they originally thought they would be AND that they walked away with solid action steps for moving forward.

These are the questions:

  1. What is the difficult conversation?
  2. Why do I need to have this conversation? What are the facts?
  3. What assumptions do I have?
  4. How have I contributed to the situation?
  5. What outcome am I hoping for? What is the goal?
  6. When and where will I have this conversation?
  7. How might the person react? And how will I respond?
  8. What blocks me? What do I need to watch out for in myself?
  9. What else do I need to prepare for this conversation? Whose input do I need? Who do I need to alert?
  10. How would I want to be treated, if someone were having this conversation with me?
  11. If it doesn’t work, what next?

So, why is it important to take the time to ask yourself questions like these before you have a difficult conversation? For me, the main reason is it forces you to both find your own accountability in whatever the situation is and consider the other person’s needs and feelings. This automatically makes you more inclined to enter the conversation with compassion and consideration. Similarly, it asks you to be considerate about how, where, and when you will have the conversation. Finally, once you’ve walked yourself through these questions, it’s pretty difficult to continue avoiding the conversation: as we know, the longer you avoid a conversation, the bigger the issue becomes. 

Does using the Difficult Conversations Wheel automatically make all difficult conversations easy? Does it always guarantee a positive outcome? Certainly not. Sometimes difficult conversations go even worse than you expected, and sometimes things don’t go your way. Sometimes you stumble. But at least with the wheel you will be more prepared for whatever might come your way.

So grab the wheel, take a deep breath, and get into conversation.  

Good luck!

Share your experiences with the wheel below, we’d love to hear about them. Have your own take on difficult conversations? We’d love to hear those too! Use the comments section below to shout those best practices to the world—in this realm, the more we all know, the better.



"Managing Up, Down, and Sideways", The Leadership Program, Inc. 2016


Erika Petrelli

By Erika Petrelli

Erika Petrelli is the Senior Vice President of Leadership Development (and self-declared Minister of Mischief) for The Leadership Program, a New York City-based organization. With a Masters degree in Secondary Education, Erika has been in the field of teaching and training for decades, and has been with The Leadership Program since 1999. There she has the opportunity to nurture the individual leadership spirit in both students and adults across the country, through training, coaching, keynotes, and writing. The legacy Erika strives daily to create is to be the runway upon which others take flight. If you enjoy these blogs, you should check out her interactive journal, On Wings & Whimsy: Finding the Extraordinary Within the Ordinary, now available for sale on Amazon. While her work takes her all around the country, Erika calls Indiana home.