January 13, 2026

Questions From the Field



You asked, I answered.



Last week, I shared my Substack article titled SWOT²: Four Questions That Open Possibility and Build Consensus.

Thanks to everyone who has already read and subscribed - and especially to those who responded with questions to which I’m delighted to share some thoughts.


From a city council member:

“Every meeting feels rushed. When I try to slow things down, I get eye rolls.

How do I pause the conversation without being ‘that person’?”


Asking for more time can sound like a delay, even when that’s not the intent. Instead of calling for a pause, try redirecting the conversation with a more basic question: “What are we most trying to protect as we talk about this?”


People are often more willing to talk about what they want to protect than what they’re ready to change. Only when core concerns feel heard does the door open to discussing future possibilities. Naming what’s “sacred” won’t decide the outcome, but it can create the time and space for better options to emerge.


From a school board chairperson:

“We say we want honest conversations, but people still hold back. The real talk happens after the meeting.

How do we change that?”


That hesitation is understandable. In many settings, even thinking out loud can feel risky. People worry that a half-formed idea will be remembered as a firm position or, worse, be used against them later.


One of the most effective ways to change that is for the chair to use their role intentionally. Build space into the agenda by clearly naming a time for ideas, questions, and possibilities before asking—or even allowing—anyone to declare a position or make a motion. Say out loud that this part of the conversation is for exploration, not commitment. When people know curiosity comes first, and that positions and decisions come later, they’re more willing to speak honestly. Candor grows when people trust that thinking out loud won’t be punished. 

From a senior staff leader:

“We keep doing things that don’t work anymore, but nobody wants to say it out loud.

How do we move on without blaming past decisions?”


One helpful move is to separate what is being said from who is saying it. In many settings, I use technology tools that let people share ideas at the same time and without names attached. (If you’ve experienced how the audience creates word clouds during one of my keynotes or workshops, I use Mentimeter technology, though others may work, too.)


When feedback comes in this way, the conversation shifts. People can name what isn’t working without worrying about being seen as critical or disloyal. It often opens the door to hearing, “This worked once, but it doesn’t anymore.” Letting go doesn’t mean anyone failed. It means the group is paying attention to what the moment calls for.


What Question Are You Carrying?


Effective leadership often turns on asking the right question at the right moment. If something has been sitting with you, I invite you to share it. We actively take on these questions—on the
podcast, on Substack, and in this newsletter—because chances are others are carrying something similar into their work as well.






Connect with Matt:


SWOT²: Four Questions That Open Possibility and Build Consensus
By Matt Lehrman January 9, 2026
SWOT² helps groups slow down, build shared understanding, and make better decisions by turning SWOT into four reflective, human questions.
A New Year, A New Conversation
By Matt Lehrman January 7, 2026
Subscribe to Democracy Runs on Dialogue™ on Substack for insights on the human side of civic leadership and the work of governing together.
A Year-End Message from Matt Lehrman
By Matt Lehrman December 8, 2025
Insights from the October Local Leadership Chat.
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