The Questions We Don’t Know to Ask
A participant in my AI Lab, Lissa, recently bought a new car. Before she paid, the salesman handed her an itemized bill, and instead of simply accepting it, she uploaded it to chatgpt and asked it to take a look. AI flagged a $550 anti theft add on and suggested it was something she should question. She went back to the salesman, challenged the charge, and he agreed to remove it.
I keep thinking about that story, not only because she saved $550, but because she probably would not have known to ask about that particular charge in the first place. She wasn’t an expert in car pricing or dealership fees. She was simply looking at a document created by someone who knew far more about that world than she did. AI didn’t make the decision for her. It helped her see that there was a question worth asking.
How often does that happen in our lives? There are documents I open and immediately know I’m outside my area of expertise. Accounting statements, insurance paperwork, complicated estimates, contracts. I can read every word and still have that uncomfortable feeling that I don’t quite know what I’m looking at.
I felt this very personally over the past year. For about six months, I was dealing with an insurance claim and constantly looking at estimates, invoices, insurance documents, contracts and other paperwork that was definitely outside my area of expertise. At the same time, I had everything else going on in my life, so the mental load of trying to understand every document, keep track of what had been submitted and figure out what needed my attention was a lot.
AI became incredibly useful in that process. I could upload an estimate or a document and ask it to explain what I was looking at, compare two versions, point out inconsistencies, or help me figure out what questions I needed to ask next. At one point, it caught that the dates on an estimate and the final paperwork didn’t line up. I could have easily missed it, and if it had gone through that way, it could have created even more delays and back and forth. Instead, I was able to flag it and get it corrected before it became another problem.
It didn’t make the decisions for me, and I still had to verify things and communicate with the people involved. But it helped me navigate a complicated process much more smoothly and reduced so much of the mental overload I was already carrying.
We tend to think that making a good decision requires having the answer. But the more I think about it, maybe good decision making often starts earlier than that. Maybe it starts with knowing there is something worth questioning.
Of course, sometimes the other person really does know more. I want accountants, doctors, contractors, attorneys and other professionals who know things I don’t know. Expertise matters. But there is a difference between respecting someone else’s expertise and removing ourselves from the conversation because we don’t know enough to participate.
This has changed the kinds of questions I ask AI. Instead of asking it to tell me what to do, I might upload something and ask, “Can you explain what I’m looking at? Is there anything here I should pay attention to? Does anything seem unusual? What might I be missing?” Then I can decide what deserves a follow up question, what needs verification and what I ultimately want to do.
Something else happened in my AI Lab this week that made me see another side of this.
One of the participants has been helping care for her father after he needed a heart stent and then suffered another medical emergency. She is already carrying a lot in her own life, and suddenly she was trying to understand imaging, bloodwork and unfamiliar medical procedures while also dealing with the emotional weight of having a parent in the hospital. She used AI to help her understand what the doctors were doing and to prepare better questions for them. She described it as helping close the gap in time and giving her a little more peace of mind.
That example made me stop and think because there was no $550 savings attached to it. The value was different. She had access to information she could understand at a moment when her mental and emotional bandwidth was already stretched.
And maybe that is part of what we overlook when we talk about the return we get from AI. Sometimes the return is money. Sometimes it is an hour we didn’t lose trying to understand something. Sometimes it is catching a mistake before it turns into weeks of emails. And sometimes it is simply being able to walk into a difficult conversation feeling a little less lost and knowing what you want to ask.
In this short episode of The Courage to Be, I share Lissa’s full story along with something similar that happened to me while reviewing the accounting for our home in Santa Fe. Between the two situations, more than $1,000 in charges were questioned simply because we stopped long enough to look more closely. I also share the questions I’ve started using when I want AI to help me understand something without handing over the decision itself.
🎙️ Watch the short episode on YouTube.
For me this isn’t whether AI can become the expert in every room. I don’t think I want that. What feels much more useful is having something that can help me move from “I have no idea what I’m looking at” to “I understand enough to ask a better question.”
There is still judgment involved. There is still verification. There are still moments when the answer from AI will be wrong, incomplete, or need a professional to weigh in. But maybe being informed doesn’t always mean knowing everything. Sometimes it means knowing enough to stay engaged.
I’m curious where this shows up for you. Is there an area of your life where you tend to accept what you’re given because you don’t feel knowledgeable enough to question it?
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