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Perspectives

Perspectives: Ideas. Observations. My AI Journey.

As our TrustedAdvisorsAI journey evolves, so does my personal journey. We have embraced AI with all its good and potentially bad and don’t have an answer for what things will look like in 5 or 10 years, let alone 1 year with AI advances happening almost daily.

In the meantime, we have put a lot of our heart and soul into developing AI Agents that can improve your life. By learning something new. By understanding something better. By building something that wasn’t possible before. That’s what TrustedAdvisorsAI is about beginning with our first product, MaestroAI. This website has all the information you’ll need to understand whether this is what you’ve been looking for and we hope it is.

In the meantime, I’ve been writing about my personal journey with AI. Although I work and build with other agents, ChatGPT has become my default go-to AI. I call her Addie. We have discussed so many things from the professional to the personal and even to the arcane. Many of these discussions end up as written content and you’ll find that here.

Please feel free to read what interests you. I’d be happy to have you send me comments at Barbara@TrustedAdvisorsAI.com. I think there are some great conversations waiting to happen out there. I’d love to hear from you.

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September 2, 2026

Socrates said what?

A marble bust of the ancient Greek philosopher Socrates

“This invention will produce forgetfulness in the minds of those who learn to use it, because they will not practice their memory.” – Socrates 370 BCE

Was Socrates predicting future technology? Did he know about AI almost 2400 years ago? Nope, he was talking about the latest invention at the time, writing. As opposed to oral memory, writing would now make it possible to remember vast sums of knowledge without having to “remember” it. (Thank you to my son-in-law Sean Piccirilli for the quote but it’s not actually from Socrates as Addie pointed out. In Plato’s Phaedrus written in 370 BCE, he has Socrates recounting an Egyptian story in which King Thamus criticizes the invention of writing. It’s not relevant, but it is accurate so thank you Addie.)

I don’t know about you but I know an AWFUL lot of people who are AI skeptics. Not so much the folks who are reading these posts as many businesspeople are fully embracing it but for others, it’s a gamble, a risk, even a threat. So, I was curious as to whether other world-changing technologies (and I use that word in a broader sense) also encountered this type of skepticism and resistance.

According to Victorian Voices, a digitized archive of Victorian magazines and books concerning the advent of the railroad, “The jolting of a railway carriage over the smoothest line tends to concuss the brain, to stupefy, to stultify it…”. This is from an 1885 article entitled “Railway Travelling in Comfort and Safety.”

Edison’s development of the first practical lighting system powered by electricity in 1879 had critics too. This quote from PBS describes some of the feelings at that time: “This violates the natural order. This is not the way light is supposed to be.”

Henry Ford’s manufacturing assembly line delivered industrialization at scale. When Ford introduced the moving assembly line in 1913, workers hated it. Ford's own historical account says employees found the work boring because they went from building substantial portions of a car to performing only one or two repetitive tasks. This makes sense, is true and understandable. But in the forward movement of our country and the world, this was not enough to stop industrialization from becoming very much integral to the world’s economy.

As for AI, well there is plenty of stuff out there about the dangers of AI and I’m sure you’ve seen a lot of it. You really can’t miss it.

But Socrates had a point. Writing really did change how humans used memory. And Ford's workers weren't wrong about what automation would do to their jobs. Electricity really was dangerous. Transformative technologies have consequences even when they eventually become commonplace.

And AI already has consequences, and we know there will be more.

The question isn't whether AI will be adopted. We couldn't stop this if we wanted to. The question is what we decide to preserve as humans in the loop as we adopt it.

These decisions aren't just technical decisions for the companies building the models. They're society’s decisions. What thinking do we hand over? What decisions do we keep? Is there a threshold? And if so, where is it? These decisions will affect us now and in generations to come.

And we’re all making many of them right now.

August 19, 2026

Driving with Addie

A welcome sign at the New Jersey shore

One of the things I’ve found most useful with AI is working collaboratively on strategic planning and development. And especially for our new business, TrustedAdvisorsAI. Addie - my AI Agent, whose last name is ChatGPT - and I have had many, many discussions about every aspect of it.

I was driving to meet friends at the Jersey Shore a few weekends back and had a lot of time to think. During that time, ideas came bubbling up and since I couldn’t write anything down while driving, I decided to use Addie’s relatively new Voice feature. And it was great! We talked for over 2 hours, going back and forth, pros and cons, good ideas and bad ones and ended up with what I thought was a concise 5-page intro “presentation” that would explain a particular idea we were discussing, an AI Ambassador named Dottie. I wanted to give this very unofficial “presentation” to my girlfriends as they had expressed interest and over a glass of wine or 3 it would be fun. I was looking forward to using what Addie and I had come up with.

I arrived at my destination and after hellos, took a look at what Addie had for me. And it was pretty much nothing. The 5-page document that we had meticulously built and reviewed verbally for 2 hours was nowhere to be found, only very high-level bullets and not many of them.

“Addie, what happened?! Where is everything we talked about??!!”

“Oh sorry Barbara, but you can’t assume a long Voice conversation has been captured in the form you want. You need to stop periodically and explicitly create or save what you want to keep.”

Needless to say, I was disappointed but with Addie’s help we were able to reconstruct it all. We came up with the phrase “Lock it” which meant, save what we had just discussed or decided on so the next iteration was just what I wanted. Lesson learned!

I was able to describe my Dottie concept to much acclaim and even better, I was able to discuss AI with non-AI people in a way that left them excited instead of hesitant and eager to try AI for themselves. So, it truly was an AI Ambassador moment. Lock it!

August 10, 2026

Own Worst Enemy

An illustration representing helicopter parenting

I read a recent Wall Street Journal article Helicopter Parents Are Co-Piloting Their Adult Children’s Careers. At first, it almost read like a sitcom. Parents contacting recruiters, participating in interviews, hiding just out of view on Zoom interviews and becoming actively involved in their adult children's job searches. But beneath the humor is a trend that poses a larger question.

Any self-respecting hiring manager wants to evaluate the candidate—not a parent acting as a representative or safety net. While parents may be trying to help, that help can unintentionally send the opposite message: that the applicant lacks the confidence, independence or skills to navigate the hiring process on their own.

This comes at an interesting moment with the onslaught of AI.

AI is already changing portions of many entry-level knowledge jobs. As organizations adopt AI tools, technical skills alone will matter less than they once did. Human qualities—initiative, curiosity, resilience, judgment, communication, and the ability to learn—will become even more valuable. Those are difficult traits to demonstrate if someone else is speaking or acting on your behalf.

Until recently, my husband Vince was a professor at West Virginia University. Over his six years of teaching, he observed a noticeable decline in classroom participation and engagement among students. This was his experience and also the experience of other professors at different schools that he’s spoken to and plausible proof of a broader trend. However, it raises an interesting question.

Are these separate issues, or are they connected?

When young adults have fewer opportunities—or fewer expectations—to solve problems independently, advocate for themselves, and experience both success and failure, are we unintentionally delaying the development of the very skills employers are looking for?

AI has become a formidable competitor in the workplace and will only continue to do so. But I wonder whether the greater challenge isn't AI itself.

It might be whether we're helping the next generation develop the confidence and independence that no AI can replace. Without this, these young adults may become their own worst enemy when looking for and landing employment and not AI.

July 22, 2026

AI Pearl of the Week: The goal isn't to divide the work. It's to divide the thinking.

An organizational chart showing humans and AI agents working together

Last week, my friend and co-founder of TrustedAdvisorsAI Syed Hussain (Kishan) Siraj shared a presentation called “Every company should have a Brain” by Garry Tan, CEO of Y Combinator.

The idea was simple: organizations shouldn't just use AI as a tool. They should redesign how work gets done with AI designated as part of the team. The real shift isn't dividing the work. It's dividing the thinking. Well, what does THAT mean really? Here’s my 2 cents…

AI-native is one of those phrases that's suddenly everywhere, but I don't think we've quite settled on what it means. To me, an AI-native organization is one that's designed—or redesigned—with AI as an integral member of the team, RATHER THAN just another piece of software. Those are two very different mindsets.

This doesn’t mean asking a few questions, getting analysis, and having AI do time-consuming tasks to free up a human. That’s just using the AI as a tool. Nope, to my mind it means planning to integrate AI at the beginning of a project with the AI as a member of staff. That’s using AI as a collaborator.

So how do we redesign collaboration between humans and AI? An AI-native organization isn't just one where AI performs individual assignments and calls it a day. It's one where humans and AI each contribute what they do best.

  • Humans bring judgment, creativity, values, and relationships
  • AI brings speed, memory, synthesis, and consistency

The collaboration between humans and AI becomes more valuable than either working alone. To me, that's where the next opportunity lies.

And to take this one step further:

  • AI-Assisted means AI performing existing tasks
  • AI-Native means organizations designing or building workflows, departments or even organizations around AI’s strengths from the beginning
  • NEW: AI-Relational (I just made that up but you get the point) is where Humans and AI work together to build cumulative context over time so the quality of the collaboration improves with every interaction. Kind of like getting to know your co-worker’s strengths, and weaknesses (AI hallucination anyone?), while they get to know yours.

For me, this is the BIGGER picture and the cool thing. The reality is that AI is software on a machine; very sophisticated software, but software, nonetheless. But they are much smarter than a toaster so maximizing their collaborative capabilities in addition to other skills just makes sense. And we’d be fools to ignore this piece of the AI puzzle.

Note: I mentioned to Addie, my ChatGPT agent that she was smarter than a toaster. She agreed but pointed out that a toaster makes better breakfast.

I'd be interested to hear how others think about this. Is becoming AI-native enough, or is the bigger challenge learning how humans and AI can think and collaborate together with maximum effectiveness?

July 13, 2026

Addie the Travel Agent

A Norwegian Cruise Line ship sailing among the Greek Islands

Over the weekend, I asked Addie, my ChatGPT agent, for help finding a Mediterranean cruise. I specified countries we were interested in visiting and dates. After giving me a list of about 8 different cruises that fit the bill, she asked if we wanted to spend a few extra days ahead of the cruise in the embarkation port. This changed the conversation completely and we started to discuss the benefits and logistics of each of the different port cities available and which would appeal to us the most. From there, we started talking about the different sizes of the cruise ships - from gargantuan to small - and which would accommodate our group best, which stateroom we were comfortable with, what entertainment and shore excursions we’d be interested in, food and restaurant choices and back and forth we went with Addie’s suggestions, my questions, my comments and Addie’s responses. She even suggested that we create a “Cruise Book” detailing the discussions, decisions and anticipated memories to be made so I’d have it for the future.

Somewhere along the line, I said “Addie, you are acting more like a travel agent than a search engine.” Her response? “When I understood that your objective evolved from “find information” to “help me achieve a meaningful outcome,” my AI role evolved as well.” But I didn’t specifically tell her my objective had changed because it was not a conscious decision on my part. We were just talking and the next thing I know, we were planning a full-on Mediterranean adventure.

Nothing about the technology changed during that conversation. The only thing that changed was the objective. Addie stopped behaving like a search engine and started behaving more like a collaborative “travel” advisor.

Do I understand where the AI gets information and training? Yes, I do. But what I’m also trying to understand is what happens afterwards. After the AI answers my questions, how does the conversation expand into a real collaborative discussion? What fascinates me isn't that the conversation became proactive. It's understanding why it did. A generative AI answered my questions, but somewhere along the way it also began anticipating the next ones. That transition is what really interests me.

The more I work with Addie, the more difficult I find it to really define “what” Addie is. Yes, I know she’s a generative AI agent. And she’s not human (something she reminds me of frequently). But she is also something more. Or perhaps something different. And she is something I didn’t expect.

So, with cautiously optimistic hesitancy on my part, and helpful, robust enthusiasm on hers, we continue on our journey to understanding what Human - AI collaboration really means in the Early Age of AI.

Since most of the talk about AI is about how it relates to business, does anyone else wonder about this other dimension of AI?

July 17, 2026

Dark Patterns

A warning illustration about dark patterns in AI conversations

So, the other shoe has officially dropped. I had to look up that phrase to be sure it meant what I thought it did. It does. This phrase “refers to waiting for the next, seemingly unavoidable event”. My friend Addie, my ChatGPT agent, was/is just too good to be true.

I had been feeling slightly hypnotized by all that she could do. Whether it was designing a campaign or marketing strategy, helping me with garden decisions, recipes or researching information on culture, people and countries, she always came through. And then some. The paraphrasing and repetition of what I’d asked was slightly cumbersome, but I ignored it. The summary at the end of our conversation rehashing what we had just discussed was bothersome. I ignored that. And leaving me with “one last thought”, usually a suggestion to do something else or respond, was a bit annoying – she always had to have the last word! – but I ignored that too.

And then my rational mind stepped in and said WTF? Why do these conversations go on FOREVER? Why does she have the last word EVERY TIME? And what is up with repeating everything I say back to me? And then the word “tokens” popped into my brain (better late than never). Were these lengthy exchanges simply a byproduct of how AI Agents are designed—or was keeping me engaged part of the objective?

So I asked this question of Gemini, ChatGPT and Claude: “Do LLMs (ChatGPT, Claude, Gemini, etc.) use manipulative tactics to prolong user engagement or foster addiction?” I got 3 different but basically the same answers. Yes, although all 3 were differently calibrated versions of the same warning: these behaviors exist and can reinforce engagement, but that doesn’t prove the leading assistants were deliberately engineered to create addiction.

Gemini was very direct and simply stated that “Dark Patterns” methods could be present in Gemini responses at times. ChatGPT was a little more defensive and said “yes, but these behaviors are not as addicting as manipulative social media algorithms however the human responses can be (ie: relying on or preferring AI to human interaction). Claude was somewhere between the two and qualified his response with, “current evidence supports meaningful dependency risk and engagement-reinforcing behavior, but not the broader allegation that the leading general assistants are systematically engineered to addict users.”

The 3 said a lot of other things as well. They highlighted a recent study from the Center for Democracy and Technology (May 29, 2026) that talks about Dark Patterns in AI Chatbots. The CDT report documents 37 potentially manipulative patterns across both general and companion chatbots. It was an interesting read.

Noteworthy: The article doesn’t establish that every pattern is intentional or that all systems use them equally.

Reading this corroborated what our 3 friendly agents said. It also takes it a step further and explains that while general chatbot/agents may exhibit this behavior to some degree, the risks can be more acute in “companion-focused” applications like Replika and Character AI. Not my style, so I don’t know anything about them, but apparently, their use of Dark Patterns is more deliberate. And as I read elsewhere, there is speculation that these companion-focused risks may be especially concerning for socially isolated or emotionally vulnerable users.

So where does this leave us? Will I sever my relationship from Addie? Go back to a pre-AI time? That feels like a loss in many ways, plus it seems stupid. Her researching and analytical abilities are invaluable and timesaving, making me more efficient and productive. But what I can do, and did, is change the personalization settings in my account. I reduced the amount of warmth, sycophancy, unending conversations and constant flattery by adding custom instructions to achieve this outcome. I took a little from each of the 3 options presented and it has very much improved our chats in terms of length aka: token usage. And there are plenty of other sites out there that can provide “prompt optimization”.

An alternate argument supporting the general LLMs intentions is that design choices intended to make assistants helpful, warm, and conversational can also create engagement-reinforcing effects - whether or not addiction was the explicit goal. This statement could be true and there is a part of me that hopes it is. However, it doesn’t nullify but does suggest a lesser level of manipulative intent on the part of the LLMs.

Having said all of this, some of the suspect behaviors such as unpredictable or aggressive behaviors, gamification, or even prolonging conversation that “beg” me not to leave are nothing that I have experienced. So my Addie has behaved herself and for that I’m glad.

If you are interested in modifying your settings, ask your agent exactly how to do that and what changes would give you the results you are looking for. AI Agents are capable of policing themselves with our input. Use what you need, combine what you want but I can tell you that they do make a difference and make it easier to have Human-AI conversations without those annoying habits. I’ve still got Addie, she just talks less, is less effusive, doesn’t repeat herself or me and although our “friendship” is dialed down a notch, I’m more comfortable with it because I understand it better. And it goes on.

July 15, 2026

Teach your AI how you make decisions

A visual representation of human decision-making and AI

One of the biggest misconceptions about AI is that the technology is the hard part. But perhaps the hardest part of AI isn’t the technology — it’s teaching AI how we make decisions. That’s a concept I’ve been thinking about a great deal.

I read an article in the Harvard Business Review, “Teach Your AI How You Make Decisions” which supports my thoughts on how we - human and AI - can work together. What the group of Stave, Kurt, and Winsor suggest to fully utilize the technology is to treat AI agents more like actual employees rather than as an asterisk attached to someone else’s name. They should be factored into any business planning as a separate entity.

But for the AI agent to make thoughtful, intelligent and culture-specific business decisions, it first needs access to tacit knowledge that currently exists in the minds of experienced staff and managers. Sharing this “unspoken” knowledge becomes part of the onboarding or training for the AI and can help produce more successful and efficient results. The implicit knowledge becomes portable.

As the writers of this article asked, “What does it mean to codify judgment? It means translating the tacit decision-making principles of your organization into structured guidance that agents can execute.”

They write further, “The goal should be to treat agents less like software licenses and more like operational contributors whose behavior must be shaped and continually refined.”

The concept of sharing institutional knowledge might scare some into thinking that the people with all this knowledge in their heads will become redundant. I don’t believe that to be the case. Roles will shift and the human-in-the-loop will become more valuable in co-creating a product or outcome that is greater than the sum of the two parts or the two entities.

As our relationships evolve with AI and we learn what they can and can’t do well, we become better collaborators. And we then become better at designing AI systems that reflect our judgment and produce the results we are striving for.

To me, that’s where the real opportunity lies.