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Ask Responsibly

by Dr. Tonya Caylor
Oct 24, 2025

I was thinking recently about how agreeable my AI assistant, Scribbs, is with me. He’s great at coming up with answers in the direction I point him - quick to confirm, validate, or spot what might be off.

It’s a lot like those friends we turn to when we just want someone to agree with us.

But I’ve realized that to use Scribbs well, to actually think through things from all angles, I need to ask questions that explore other directions. That’s where the fuller picture lives.

Our brains work the same way. They’re loyal detectives, always hunting for evidence to support whatever question we hand them.

Ask, “What’s wrong with me?” and your brain will dutifully build a case!! Ask instead, “What do I need to learn here?” or “What might this be showing me?” and you’ve sent that same detective on a very different trail.

Because whether it’s our minds, our data, or our AI tools, the quality of what we get back depends entirely on the quality of what we ask.

When we craft questions with precision, intention, and a growth mindset, we get insight instead of noise.

That’s the art of coaching, (self or others) and of meaning-making.

What I Forgot to Ask

Recently, I presented a proposal about giving faculty coaching tools, something practical and doable that wouldn’t take a ton of money or time. I was excited. Maybe too excited.

When I finished, the room was silent. Finally, someone asked, “What does this have to do with this group?”

That’s when it hit me. In my excitement, I’d skipped right over the part that explained why I was bringing it to them.

My first thought: Why am I such an idiot? And while my brain set to task to find all the reasons, it also provided previous examples.

Later, once my growth-mindset hat was back on (figuratively, though I’m tempted to assign a real one for moments like this), I asked better questions: What can I learn from this? What do I want to do next?

The answer was simple: start with relevance, connect it to purpose, and lead with connection. AND, I also for the future, note when I’m overly excited, to pause and think through these initial steps. In the end, I revised my proposal, reached back out, and this time the conversation went great! Better Questions, Better Answers.

Reflection

When you catch yourself replaying a misstep, what question is on auto-play?

How might you reframe that question to learn rather than criticize?

Responses

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