AI Then and Now: A Leadership Lens
Aug 31, 2025
Is Your Team Giving Real Insight—Or Just Fast, AI-Generated Answers?
❓ Ever get a reply that checks every box, but misses the point?
AI is built for efficiency.
But it's the human perspective that creates momentum.
A tech exec we work with forwarded a market report to their Marketing leader with a quick, "What do you think?" The response? Lightning-fast, well-organized, and…oddly generic. Turns out, it was crafted with a bit of help from AI.
Here's the thing:
AI has a place in our work. But when it's used just to check a box, giving a quick answer so we can move on, we lose what matters: insight, ownership, and connection.
The exec didn't want to accuse their leader of using ChatGPT for a shortcut (awkward, right?), but it sure felt like that's what happened.
Our conversation turned to this:
🚀 How do you ask better questions - questions that make it clear you want more than a "check the box" AI-generated response?
Maybe the Marketing leader was just trying to keep things moving. (Who isn't these days?) But this isn't about blaming AI or busy schedules. It's about how easily we all miss moments for authentic connection and real insight when we're moving too fast—or when our asks are too vague.
The disconnect didn't start with the response. It began with the ask.
So, what could've gone differently?
Here's what we shared with the exec (and what we try to practice too):
Instead of:
"Can you take a look and send me your thoughts?"
Try:
"After reviewing this data, what stands out to you? What's one thing leadership should know that isn't obvious from the numbers alone?"
or
"Are there any patterns or shifts that feel significant to you personally, or that you think we might be missing?"
Those kinds of questions invite reflection, ownership, and shared meaning. It is about Conversations Worth Having.
🔹AI? Brilliant for summaries. Lightning quick with the facts.
🔹But insight? That comes from perspective.
🔹And perspective? That only shows up when you do.
Maybe it's not just about getting an answer—it's about inviting real thought. Fast responses have their place, but leadership moments call for more than checking a box.
What would happen if, next time, you asked not just for thoughts, but for the story behind them?
You might discover insights and connections you didn't even know your team had.
❓To the leaders shaping the AI-future:
How do you make space for honest reflection in your leadership conversations? What's worked (or not) for you?
