Creating the Win-Win

Mar 24, 2024
A diverse group of seated professionals smiling and enjoying a corporate event.

It's incredibly uplifting when colleagues eagerly volunteer to plan and deliver an event at work. Their enthusiasm sparks a contagious energy that fuels collaboration and innovation. Everyone’s unique perspective and expertise contributes to a tapestry of creativity and excellence.

And we've likely all heard the sound of crickets when we ask for volunteers. 

Born from our Monday Kickstarters session, the challenge we address in this blog is: How do you ignite the desire to volunteer to co-create, come together with a shared sense of purpose, and have conversations where great ideas emerge?

Read on to discover how our Monday Kickstarters' participants helped to flip this challenge and create a frame that invites people in to meaningful interactions and collective efforts to achieve goals and strengthen bonds that enrich the workplace community. You'll see the power of asking generative questions and shifting the frame to inspire conversations worth having plus one Cool Tip you can use during any conversation!

Positive Frame

Name it:
 I’m hosting an event for our leaders and am struggling to get internal help and positive support.

Flip it: I have the help and positive support I need for this event from my colleagues.

Frame it: A wildly successful event that uplifts leadership and builds internals relationships.

Other Suggested Frames

  • A well regarded and engaging event with risks mitigated, something we are collectively proud of.
  • I'm energized by the help and support my colleagues are contributing, and we are building relationships together.
  • There would be so many people (colleagues) volunteering for the event, there would be a waiting list.
  • Colleagues can't wait to roll up their sleeves and help and also participate in the event


Generative Questions

Once the frame was in place, the group crafted generative questions that could create a conversation worth having, one that works for everyone involved.

Generative Questions for Yourself

  • How can I think differently?
  • How am I getting in my own way?
  • What can I do differently?
  • Who can help me get the support I need?
  • What are the helpful contributions people are making already?


Generative Questions for Others

  • What difference will a wildly successful event make to our organization?
  • Looking back a year from now, what impact will this event have?
  • What motivates you to volunteer at work?
  • How would you like to be recognized for your contributions to this event?
  • When you have contributed to a large event like this before, what did you do? What conditions made that happen?
  • Describe a time when you were energized and excited volunteering for an event. How might we re-create that for you now?
  • When was the last time you attended an event like this that exceeded your expectations?
  • Describe the most wildly successful event you have ever attended. How might you want to bring elements of that into the event by volunteering?
  • Tell me about a time when a colleague helped you and the outcomes were fantastic – what made it possible? How did you ask for help?


Cool Tip!

In Conversations Worth Having, taking a pause isn't just a moment of silence – it's the way to access your brain's superhero abilities! Picture this: by hitting the pause button, you're giving your mind the chance to juggle thoughts, shuffle memories, and even tame unruly emotions. It's like pressing 'refresh' on your mental browser! With this essential break, you're not just catching your breath, you're gearing up to tap into your curiosity and ask generative questions that enrich the conversation. So, the next time you're engaging in Conversations Worth Having, remember to sprinkle a few pauses into the mix – you'll be amazed at the outcomes!

About Monday Kickstarters

This topic came from our Spring 2024 Monday Kickstarters series, working sessions to figure out how to have a conversation worth having when faced with a tough situation, challenge, or problem with leadership or performance. Learn more about Monday Kickstarters and other ways continue your CWH practice here

Shared by: Kelly Stewart, a certified Conversations Worth Having Trainer, Strategic Conversation Facilitator, Appreciative Inquiry Facilitator, and co-founder of the CWH Institute, Inc. Where a vacuum exists, Kelly has an innate tendency to rush in, even when it’s not asked of her. She delights in experiencing the positive outcomes that come from the act of simply pausing and encourages others to make pausing part of their response mechanism. 

Photo by wes lewis on Unsplash



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