Flip the Script on Tough Conversations

Turning Difficult Conversations Into Possibilities

Every team has moments when tough conversations feel like the last thing anyone wants to have. Maybe it’s about giving feedback, tackling a disagreement, or talking through a mistake. But what if we flipped the script? Instead of seeing these moments as “difficult,” we could see them as opportunities to connect, understand, and grow together. After we've flipped our mindset to the positive opposite, we can start creating a positive frame around that preferred scenario and asking generative questions, turning challenge into possibilities and helping to create a culture and environment where everyone can truly flourish.

Challenge #1 - Flipping the Script at Work

This week’s Kickstarters Group tackled a common challenge in work teams, and after we flipped it to the positive opposite, we applied positive framing to flip the script.

Positive Framing for Team Conversations

Name it: People in my work unit don’t embrace difficult conversations.

Flip it: People do embrace difficult conversations.

Frame it: Everyone flourishes in this culture and the team is very strong. 

To imagine what a flourishing team looks and feels like the group generated questions designed to spark stories, ideas, and possibilities that could move a team toward its best self.
 

Generative Questions to Envision a Flourishing Team

• When was a time that the team was flourishing and what made it so great?
• What are three things that happened that made this day go so very well?
• What are three practices this team does that we want to keep? What practices would help our team be even stronger?
• What are the markers that would demonstrate we are flourishing? How would we be feeling?
• How do you understand flourishing?
• How can we be bold in our flourishing together?
• Where do we see flourishing teams in other organizations?
• Imagine an article is being written about our flourishing team a year from now. What would it say?
  
  

Challenge #2 - When Communication Gets Complicated

The Kickstarters group then explored a second challenge in which an adult child made some investment decisions for Mom…without telling her or the other siblings. Yikes!

Positive Framing for Family Decision-Making

Name it: The goal for investment decisions for Mom is not clear to all of us.

Flip it: The goal is clear to all of us.

Frame it: Mom has peace of mind and trusts us to handle her finances wisely.

Generative Questions That Bring Clarity and Trust

• What do you think is Mom’s goal for investments?
• Which of our characteristics enabled Mom to entrust us with managing her money?
• How can we team up to help Mom regain confidence?
• What has helped Mom be confident in the past?
• What does Mom really need to be able to relax? When did we see Mom most relaxed – what was happening?

Conversations Worth Having Cool Tip

The next time a hard conversation comes your way, take a breath and ask yourself: “How can this conversation help us grow stronger?” That small shift in thinking opens the door to empathy, courage, and collaboration—and reminds everyone that flourishing starts with how we choose to show up for each other. Learn more about why this work and other practical conversation tools you can learn in less than 30 minutes and use right away.