Am I Overthinking This?

Apr 01, 2022
Am I Overthinking This? Conversations Worth Having Blog

In today’s Kickstarter session, a participant shared that engagement numbers in her organization had decreased significantly following recent changes and the hiring of a number of new staff. Charged with investigating the situation and generating ideas to help increase engagement, she was not sure how to proceed.

Clarify the Issue

While responding to some initial generative questions from the Kickstarter group, the participant wondered if the real problem was that she might be overthinking the situation, which lead to the following:

  • Name it: I am overthinking the situation.
  • Flip it: I am open to the possibilities; holding the outcomes loosely. [The exact positive opposite would be: I’m clear about what to do.]

This lead one of the participants to ask: What is the outcome you are hoping for? This resulted in:

  • Frame it: We have a shared understanding of factors influencing engagement and we know what changes might increase engagement for everyone.

Generative questions:

With the positive frame in place, group members posted a fabulous selection of generative questions on the whiteboard:

  • Think of a time when you felt high engagement with our organization, our colleagues, your work…
  • When have you felt most engaged at work? What were you doing?
  • What do you think needs to happen for us to move forward?
  • Where do we have opportunities to support excellence and a great place to work?
  • Are there things to learn from mentorship that might help facilitate these conversations?
  • What brought you to this organization? What are our shared goals?
  • Either here, or in a previous job, talk about a time you felt most connected to the organization and your coworkers.
  • If we were working collaboratively and cohesively, how would that impact our end user?
  • What can we innovate or create to make this a best place to work?
  • What first brought you here and why do you stay?
  • What is your favorite part about working here?
  • What are your key strengths and how might we use them in more effective ways?
  • What would look different in our organization/with your colleagues/your work if it contributed to your high engagement?
  • What elephants do we need to address? What might we do with them?
  • Tell me about a time you felt engaged in this organization. What influenced hat?
  • What would you notice if changes were happening you would welcome?
  • Who are we when we are at our best?
  • When you have done great work here, what contributed to that?

The ones that resonated most with the person with the challenge included:

  • When have you been most engaged and alive in the organization? What conditions made that possible? What did you value about yourself and others?
  • If a specific action/change could increase your engagement, what do you imagine that might be?
  • What does it look like to have everyone engaged – both new and older members?
  • Who are we when we are at our best?
  • Imagine this works for everyone, what would that look like?

 Cool Tip:

There are three great opportunities to ask generative questions. The first: during the name it step. Make sure you’re focused on the real issue. Ask generative questions to help gain clarity. The second: after the flip to help you identify the positive frame. What outcome are you hoping for? If the flip is true, what’s possible? The third: after you have a positive frame.


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