What if one powerful question could shift a conversation from tension to trust?
What if curiosity—not judgment—was your most effective leadership tool?

In May’s Monday Kickstarters, we explored three real-world, admittedly frustrating and complex, scenarios. But instead of staying stuck in the problem, we tuned-in – pausing, breathing, and getting curious. In all cases, first we named the issue and then gained clarity by asking generative questions. Sample generative questions for gaining clarity include:

• How does this impact you/the team?
• Why is this a problem?
• What’s the frustration?
• What’s not happening that concerns you?
• What is the sticking point?”  

Three Challenging Scenarios

In two scenarios, we clarified the issue and then created a positive frame and generative questions the person could ask to move toward resolution. In one scenario, asking generative questions surfaced a lack of information. We could not clarify the real issue without engaging another person. This is an important distinction. If you can't gain real clarity in name it, avoid making up stories to explain or jumping to conclusions. Instead, take time to pause, breathe and get curious. What don't you know? What questions do you want to ask that will help clarify the real issue. Then engage the other(s) in a conversation worth having.

Scenario 1

I’m Not Invited to critical meetings.

We began with generative questions to gain clarity on the real issue:

• How does not being included in critical meetings impact you?
• What would be different if you were included in critical meetings?

The answer to these questions lead us to the real issue:

• Name it: I’m not informed sufficiently and I miss deadlines.
• Flip it: I am informed and meet all deadlines.
• Frame it: I have the full understanding and information I need to perform at my best and I contribute to planning and setting deadlines.
• Framing the conversation with the manager: When I’m not included in critical meetings, I don’t have the full picture of my role and those creating plans don’t have information critical for planning and setting attainable deadlines. In order to perform at my best, I need to understand the full picture and have all the information. And to meet deadlines, the planning team needs to understand what’s possible on my end. Then ask generative questions:
  • What are ways that we might ensure I have full understanding and information about my role so I can perform at my best?
  • How might I contribute to planning and setting deadlines?
  • Which of these possibilities would be the more efficient and effective for all of us?

Scenario 2

I am supporting a childcare provider who cares for a child with a disability. This child is a full-day Kindergarten student who is being removed mid-day and going to a childcare program. This is against public education laws.

Again we began by asking generative questions to clarify the issue. It quickly became clear that there was no way to create a positive frame for the conversation without more information. Any frame we created in isolation would be based upon assumptions, judgments, and made up stories. The issue needed to be clarified in partnership with the childcare provider. Here were the questions that could inform that conversation:

• What led to the decision to have the student transition to childcare mid-day? Was there a specific concern or behavior pattern?
• What’s been your experience with the child’s schedule and the type of support being received?
• What supports or accommodations have already been tried in the classroom setting? What’s worked, even a little?
• If resources weren’t a limitation, what kind of support would you ideally want to help keep the student in class full day?
• Are you aware of the legal requirements?
• To meet the law, what else would need to be in place?
• How can I support you to help this child?

 The tone and direction of their conversation

will now be one worth having!

Taking just a few minutes to generate these questions resulted in an internal shift for the person who is supporting the childcare provider. She realized she was making assumptions. It pays to pause, breathe, and get curious. What other stories could explain the childcare providers decision? What don’t I know?  She told us, “Now I’ll be able to stay curious and open about the why without assuming it is them not wanting to follow the law or not wanting the child in the classroom.”  

Scenario 3

A man being coached is not accepting the responsibility for developing a woman who is a direct report because he has a personal issue with her. 

As we dove in to ask questions to gain clarity on the issue, the issue seemed pretty straight forward.

Name it: Coachee has a personal issue with a direct report that interferes with his responsibilities.

Flip it: Coachee follows through on responsibilities even though he has a personal issue with direct report.

Frame it: Coachee gains clarity on his issues in ways that allow him to be responsible to his direct report.

Generative Questions:

• What assumptions are you holding about this person that might be influencing your approach to her growth?
• What's specifically getting in the way of your ability to support her professional development?
• What’s important to you about your relationship with the direct report? Or the type of support you provide for her?
• What do you enjoy and appreciate about working with this person? Even something small.
• What is your role in developing the direct report? How do you view your role in her development?
• From your perspective, what would have to happen for you to be capable of supporting her growth and development?
• From your perspective, what has to happen for you so that you can accept your responsibility to support her growth and development?
• What would an ideal relationship with your direct report look like?
• How do you want to be known as a leader when it comes to fairness and development?
• How might you use SOAR as the template for working with her? What are her strengths, aspirations, opportunities, and desired results, from your perspective and from hers?
• How do you think she views you?
• What kind of support do you need to feel better about coaching this person?
• If you were able to support her development, what would you do and how would you go about it? What has to happen for that to happen?

And then a few questions for the coach to ask about coaching this person:

• What would you like to accomplish in this coaching agreement?
• Looking at our goals for the coaching agreement, what are our goals for working together? (Seems like you might want to renegotiate the outcomes and deliverables to assure he takes ownership)

From Fixing the Problem to a Conversation Worth Having

These weren’t questions to fix a problem. They were invitations to widen the screen: make the invisible visible, create shared understanding, generate new knowledge, and create possibilities. Moving forward toward solution only happens when we involve others in creating a positive frame and generating opportunities for movement. That conversation sparks the journey forward.  

This is the heart of CWH: using intentional, generative conversations to move from reaction to possibility—and from disconnection to collaboration. 

Ultimately, when you lead with curiosity and clarity about the future you want to co-create, even the hardest moments can become powerful turning points.

Want to learn more? Our Monday Kickstarter sessions will start back up in the fall. If you're interested in joining to practice asking generative questions and creating positive framing, we welcome you. To make sure you are prepared and ready to participate, we now require participants to take the 30-minute CWH Foundations Course or the Conversation Bootcamp. The Foundations course is available at half price through May 30. You can use coupon code COMPASS at checkout!

Shared by Laura (Elle) Finnegan and Cheri Torres, hosts for May's Monday Kickstarter.

Photo credit: Praetorianphoto, istockphotos