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Clayton Rose Group
Leadership 3 min read September 10, 2026

The Leadership Habits I Want to Keep Practicing

Kelly Rose Hall, Founder of Clayton Rose Group
Kelly Rose Hall, IOM, CCE, MBA
Founder, Clayton Rose Group
A young professional listens attentively among colleagues during a leadership session

I enjoy helping organizations succeed by working with their staff and boards. Through Clayton Rose Group, I help leaders develop disciplines they can use in everyday decisions. One of those disciplines is testing assumptions. A conversation at the chamber reminded me how easily I can skip that step myself.

When we were hosting AI courses at the chamber, I asked one of our employees to take a course. I also asked whether she already had an AI app on her phone. She told me she didn’t use AI.

I was shocked. She was a young professional, a top-notch employee, and someone I thought would already be using it. I had made an assumption based on her age without ever asking about her experience.

So I asked why.

Her response threw me for a loop. She explained that, because of her age, people assumed she didn’t know how to think critically. She worried that if they saw her using AI, they would think she was cheating or couldn’t do the work herself.

Wow. I didn’t see that coming.

Ask before you decide

I had been thinking about a tool and a training opportunity. Her concern was how others would judge her ability. That deserved a conversation I would never have known to have if I had stopped at my first assumption.

It was a reminder to practice what I ask other leaders to do. We can know our employees well and still misunderstand what is shaping their decisions. The same is true when we work with a board. Experience with someone does not tell us everything about how they see an issue.

Testing assumptions is part of foresight. We examine what we believe to be true, consider how conditions could change, and ask what that might mean for the decisions we are making now. Other people’s perspectives help us see what we may have missed.

Make room for foresight in the meeting

Imagine a staff meeting about introducing AI into an organization’s work. Before choosing a course or setting expectations, I would want us to explore a few questions.

  • What are we assuming about who uses AI and who feels comfortable using it?
  • What concerns might people have about how their work will be judged?
  • If AI becomes part of our everyday work, how will we recognize good judgment and help people feel comfortable asking for guidance?

Those questions could reveal very different needs. Someone may need instruction. Another person may need clearer expectations about appropriate use. Someone else may be worried about the same thing that employee described to me.

A board can apply that discipline when considering how technology may change the organization’s work. What skills might become more important? What are we assuming our staff already knows? How will we check those assumptions before making a commitment?

When I work with organizations, I want their meetings to make room for that kind of thinking. It gives people a chance to influence a decision while there is still time to consider what they know.

I am still practicing, too. That employee gave me a valuable reminder: ask why, listen carefully, and be willing to change my understanding.

Kelly Rose Hall, Founder of Clayton Rose Group
Kelly Rose Hall, IOM, CCE, MBA
Founder, Clayton Rose Group

Kelly Rose Hall is the founder of Clayton Rose Group, advising chambers, trade associations, and member-driven nonprofits across the United States from Longview, Texas.

Want help putting this into practice?

Schedule a 30-minute discovery call with Kelly. No deck, no pitch. Just a conversation about what your association is trying to become.