AI Can Make You Sound Like An Expert. What Shows You Actually Are?

Hi everyone,

How’s your week going?

I still find it a little amusing that after more than 40 years in publishing and content, I’m spending so much time thinking about tools that can produce in minutes what used to take us days.

I use them. I’m curious about them. And yes, I like saving time as much as the next person.

But I’ve spent enough years getting things wrong, fixing them, and occasionally wishing I’d listened to somebody sooner to wonder how much of that experience shows up in the finished work.

People see what you put in front of them. They don’t necessarily see why you changed your mind three times before you got there. Sometimes those three changes are the most valuable part.

Then I came across this: A new literary prize in France is recognizing fiction written in collaboration with AI. It’s called the Prix Pascal, and entrants are asked to disclose the AI tools and prompts they used.

Well, that got my attention.

Having spent much of my life around books, I wanted to know what the writer brought to the work. What did they want to say? What did they push back on? What sounded perfectly fine to the machine but felt wrong to someone who had actually lived through it?

Those are the questions that interest me. And I’d ask much the same of a consultant, a coach, or anyone whose advice I was considering taking.

You sound like you know what you’re talking about. Help me understand how you came to know it.

That’s where I think the interesting conversation begins.

Tell Me About The Time It Didn’t Work

Imagine you’re considering two consultants. Both have impressive websites, well-written articles, and a framework with a name that sounds like it ought to be trademarked.

Both seem to understand your problem. On paper, there isn’t much between them.

Then you ask: “Tell me about a time this approach didn’t work. What did you miss, and what did you change?”

Now we have something to talk about.

I want to hear what they expected, what surprised them, and which assumption turned out to be wrong. I want to know why something that helped one client would have been the wrong advice for another.

After all these years, I’m much more interested in that conversation than in a flawless presentation. I’ve made enough decisions I’d like another shot at to be suspicious of anyone whose career seems to have gone perfectly.

Experience should give you a better understanding of the circumstances in which your advice applies. It should also help you recognize when you need to ask another question before offering it.

An honest explanation of a difficult decision tells me something a polished answer often leaves out.

Sometimes We Edit Out The Expertise

Here’s where I think experienced professionals make life harder for themselves.

We clean everything up before we show it.

We share the finished project, the successful outcome, the nice testimonial. We leave out the uncertainty, the false starts, and the decision that took three conversations to get right.

Of course, nobody wants to sit through every meeting you’ve ever had. Most of us didn’t want to sit through them the first time.

But in making the story shorter, we sometimes remove the part that would help someone understand our value.

A finished course doesn’t explain why the lessons needed to be reordered. A good video doesn’t show the decision to drop the polished script and ask a better question. A clear article doesn’t reveal that the strongest idea was originally buried in the last paragraph.

Those decisions matter. They’re often where the experience shows up.

The finished work lets people judge the result. Explaining a few of the important choices helps them judge whether they would trust you with their own problem.

Make The Important Decisions Visible

I’m not suggesting everyone needs to start documenting their entire working day. We have enough content already.

I’m suggesting we explain a little more about the work we choose to share.

If you helped a client clarify their message, what was confusing about it? Were they talking to three different audiences at once? Were they describing what they did without explaining why anyone should care?

What did you change? Why did you start there?

If you’re sharing a result, give people enough context to understand it. Where did things begin? What was your contribution? What else might have affected the outcome?

And if you recommend a particular approach, tell us when you wouldn’t recommend it.

That last part matters to me. I’m more inclined to trust someone who can explain the limits of their advice than someone who somehow has the same answer for everybody.

You don’t have to disclose confidential information or give away every detail of your process. One well-chosen example can help someone understand how you work.

The point is to make your judgment easier to examine.

A Strong Opinion Needs Something Underneath It

I like a strong opinion. At my age, I’ve accumulated a few. Some have even survived contact with reality.

But I should be able to explain where an opinion came from and what might make me reconsider it.

For example, I believe experienced professionals often overlook the value of material they’ve already created. There can be years of useful thinking sitting in presentations, workshop notes, interviews, articles, and client conversations.

That doesn’t mean all of it needs to become a book. Or a course. Or another fifty posts.

Some ideas need room for a deeper argument. Some need demonstration. Others become useful when people can practice them, ask questions, and apply them to their own circumstances.

The judgment is in deciding what deserves to be developed, who needs it, and which form will help them use it.

When those choices are clear, the different pieces can support one another. An article introduces an idea. A video shows it in practice. A course helps someone apply it. A case study gives them something concrete to examine.

Together, they give people more ways to understand your thinking. Someone can encounter your work in different places and begin to recognize how you approach a problem.

But each piece needs a reason to exist beyond filling a slot on the calendar.

A Good Story Still Needs Backing

There’s a catch here, of course.

Someone can invent a detailed story about a difficult decision. Adding a few mistakes and a lesson learned doesn’t automatically make it true.

So wherever possible, give people something they can check: work they can examine, a documented change, an example shared with permission, or a client who can speak to what happened.

And be honest about what the evidence actually shows. If several things contributed to a result, don’t take credit for all of it.

I think we sometimes underestimate how reassuring that honesty can be. It tells people you understand the difference between making a claim and supporting one.

The same applies to AI. Disclosing its use is useful, but disclosure alone doesn’t establish the quality of the thinking. You still need to stand behind the facts, the recommendations, and the choices in the work that carries your name.

Over time, your work should help someone see whether your explanations hold up, whether your advice changes with the circumstances, and whether you’re willing to acknowledge exceptions.

People shouldn’t have to take your entire professional reputation on faith.

Experience Doesn’t Always Speak For Itself

This is the part I have to remind myself of, too.

After decades in publishing and content, there are things I notice almost automatically. A question I know to ask. A problem I recognize before it becomes expensive. A reason to pause when everyone else wants to move ahead.

Because those things feel familiar to me, I can forget they may be useful to someone else.

A person encountering my work for the first time doesn’t know what I’ve learned or what I’ve gotten wrong. They don’t know why I would recommend one direction and question another.

I have to explain enough for them to decide whether my judgment is worth trusting. My years in the business don’t relieve me of that responsibility.

So here’s the question I’m asking myself:

If someone removed my name, title, and years of experience from my work, what would still demonstrate my judgment?

It’s a harder question than it first appears.

Before you rush to create something new, take another look at something you’ve already shared. Is there a decision behind it you never explained? A tradeoff you worked through? Something you learned the expensive way that might save someone else some trouble?

That may be more useful than another polished opinion.

I’d love to hear what earns your trust. When you’re deciding whether to work with someone, what makes you think, “Yes, this person understands what I’m dealing with”?

For me, it’s often the moment they ask a question I hadn’t thought to ask. It tells me they’re paying attention to something I may have missed.

Enjoy your weekend. And if you have a story about a lesson you had to learn the hard way, I’m always interested. I probably have one to trade.

More soon.

Warmly,

Jan

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