Managing Tough Conversations: How Improvisation Can Get You Through

The following is a guest post from ProjectHR guest Karen Hough. To learn more about the work she's doing as Founder and CEO of ImprovEdge, a company offering virtual and in-person business training, rooted in the practice of Improv, head here!

Managing Tough Conversations and Improv

Have you been in any of these situations?

  • Your colleague’s performance is slipping and it’s making the rest of the team frustrated.
  • Your direct report has not met the requirements for a raise.
  • You’ve been chosen to discuss an inappropriate attire issue with a new employee.

We’d all rather go to the dentist than have those conversations, right?! The idea of hurting someone’s feelings, delivering bad news, or dealing with a sad or angry colleague is scary. We do everything that we can to avoid these tough conversations, which is a disservice to ourselves and the other person. People are often not aware of an issue, concern, or behavior and need insight to improve and move forward.

A surprising analogy and antidote to this problem is improv. That’s right – improvisation! Improvisation is the art form where five to six actors go onstage without a script, costumes, or props, and create an entire show in the moment, without a safety net. It’s incredible, exhilarating, and based on behaviors that can help you with navigating difficult moments and managing tough conversations.

tough conversations

Seven Critical Behaviors from Improv for Managing Tough Conversations


At ImprovEdge, we define courage as a willingness to engage in a candid, collaborative conversation; acknowledging you don’t have the only perspective. In other words, the willingness to give and receive feedback – or as we say at ImprovEdge, feedforward. This is forward-facing because we can’t go back and change the past, we need to look at changes that we can achieve for the next time.  Each time that you engage in a conversation that makes you really nervous, you are showing courage! This is just like the moment when an improviser goes on stage with no idea of what is going to happen, they show courage!


Improvisation is based on positivity and agreement. “Yes, and” is the way improvisers make anything happen. Managing tough conversations with the improviser’s outlook is powerful.  Positivity means looking for the best in people and in situations – past, present and future. It means assuming positive intent and knowing that you may need to hear the other side. In preparing for your coaching and difficult conversations, discover the strengths and “best of” experiences for the other person.

Open-Ended Questions

The most powerful skill in effective and collaborative communication is – how do we question? Effective questioning and the ability to learn and understand the motivations of other people is often the most important, but unsung skills of successful professionals. In difficult conversations, this offers both parties the opportunity to uncover assumptions and preconceived ideas. For the coach, the best approach is to ask a great open-ended question and be prepared to listen.


As improvisers, we enter into every situation not knowing where it’s going to go. We trust our teammates (they want us all to do well), have a common goal (a great show) , let others lead, AND we are ready to step up when it is our turn. All of us have diverse styles of communicating, relating, and interacting. In order to collaborate and communicate effectively, you may need to listen, drop assumptions and adapt. Be flexible like an improviser and be prepared to listen and create a more collaborative and inclusive situation


Visioning allows us to consider  the best possible outcome for this conversation. By approaching a tough conversation with a positive outcome already in your head, you bring an attitude and energy that can affect the outcome. This is the same for improv – how you show up affects the show! Have a vision for success. What is the dream?


In the perfect brainstorming session, you would come up with many possibilities for action. What are the steps that it will take to get to your dream vision?  What do I need to do today? What behavioral changes do I need to make?  This process should involve both parties in the conversation and no idea should be discarded! This is the ultimate “Yes, and” from the world of improvisation. We combine and expand on each other’s ideas and discover innovations and solutions that we never even considered!


A reflection allows the listener the opportunity for clarification and understanding. Simply, after listening, you say, “What I hear you saying is…” or “Let me make sure I understand, you want…”There are two types of reflections that can be valued in difficult conversations – restated reflections (mirroring the information as stated) and empathetic reflections (mirroring the information and emotion). This is not about solutions – this is about staying in the improvisational “Yes Space” and hearing what is being said. “Yes Space” insists that the improviser agree with the situation and stay with scene as their partner sees it – not as they wish it to be. It’s the same for tough conversations; you have to listen to their side without assumption or interruption. This skill allows you to listen and clarify the facts of a situation and eliminate any assumptions that may be a part of the conversation.

Here is a great article on the importance of empathy-based management.

managing tough conversations

Three Steps for Great Outcomes

PREPARATION: Preparation is critical to improv and theater success; all the rehearsals that lead to the opening night performance. It’s all about warming up, feeling ready, and getting yourself in the right mindset – a positive space. Preparing like an improviser allows you to be ready for any of the unexpected moments that may come your way during a tough conversation. Some steps to preparation include examining your purpose for the conversation, uncovering your perceptions, and determining the best time to take action. ImprovEdge and the eLearning provide a Preparation worksheet so that you can feel confident and ready.

ENGAGE IN THE CONVERSATION: Conversation involves others – this is where conversations are improvisational. We don't know what the other person will say or how they will react; therefore, we need to be ready to be flexible, creative, and positive. ImprovEdge and the eLearning provide a conversation worksheet that serves as a blueprint for the conversation. It should be transparent so all parties can participate and feel included. Then during the conversation, you lean on the seven behaviors above, like Courage, for a great outcome!

ACT: Action requires participation and goal setting. This is the step that requires follow-up and outcomes for both parties. When performing in an improv show, both those onstage and those in the audience are actively participating in the performance!  In a collaborative conversation, each party agrees to the next steps, highlights the priority items and reasons to change behavior now, and commits to SMART goals to follow-up. Once you have prepared and then engaged with your colleague, you should be in a place of better understanding and agreement. It’s a critical moment to Act.

Wrapping Up

These behaviors and steps prepare you for managing difficult conversations with the mindset of an improviser. Improvisers are some of the most over-prepared people in the performance industry because they have to prepare for the unexpected. The next time you must have a difficult conversation, prepare like an improviser with courage and positivity, and utilize the improviser’s behaviors of open-ended questions, visioning, brainstorming, listening and reflections.

About the Authors

Karen Hough, Founder and CEO (Culture & Experience Officer) of ImprovEdge is an Amazon #1 bestselling author, Yale grad and winner of the WNBA Inspiring Woman Award and the WBENC Pitch Pivot Grand Prize. She has combined the art of improvisation with research in neuroscience and human behavior to transform adult learning for 20 years serving Fortune 100 companies on 4 continents, and ImprovEdge is in the top 4% of woman-owned businesses in the US.

April Olt is the Director of Design and a Senior Facilitator with ImprovEdge. She received her MFA from the Chicago College of Performing Arts at Roosevelt University. For the past 14 years, she has worked with global clients to create customized content using improvisation to transform individuals, teams, and organizations. April continues to teach, direct, and develop talent across the US and at home in Los Angeles, CA.

Alex Lefeld is a Senior Facilitator with ImprovEdge and brings over 10 years of experience in improvisation and teaching to the ImprovEdge Ensemble. He developed his passion for training in the hospitality industry and still supports his local theatre community in Columbus, Ohio. His students have gone on to perform on Broadway, the Second City Mainstage in Chicago IL, and even as researchers and engineers at NASA.

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