The Lens That’s Costing You the AI Race

REDEGADES.AI on June 27, 2026

Most companies are not failing at AI because AI is hard. They are failing because they are looking at it through a lens that is twenty years old. And that lens was built from decisions that were, at the time, exactly right.

You Made All the Right Moves. That Is the Problem.

Over the last two decades, the business world made a massive, correct shift: from owning software to subscribing to it. Email, documents, design tools, video meetings, all in the cloud, all on a subscription, none of it running on a server in a closet down the hall. Today, somewhere between 60 and 75 percent of enterprise software is delivered this way. That number keeps climbing.

And for most companies, outsourcing IT followed the same logic. Why hire and retain an internal IT team when a Managed Services Provider gives you better coverage, deeper expertise, and lower cost? More than 65 percent of mid-market firms operate this way now. Smart. Efficient. Right call.

Here is the problem: two decades of smart, right decisions have a side effect. They trained the entire business world to think in one mode. Find a subscription, hand it off, move on.

That Mode Is Now Your Biggest Barrier to AI

There is no subscription that makes your team smarter with AI.

There are plenty that make you smarter as an individual. ChatGPT, Claude, Copilot. Pick your flavor. They will make you faster, sharper, more effective. But none of them, right now, are built to raise the intelligence of your team as a unit. That gap is real, and it is not solved by clicking Start Free Trial.

When we talk to companies about building real AI capability, we hit the same wall every time. They go looking for a pricing page. When they cannot find it there, they assume it does not exist, or that it is too complicated, too expensive, too much work. It is not. It is actually the opposite. But you cannot see that if you are still looking through a twenty-year-old lens.

The Companies Already Winning Did Not Plan for This

Here is the counterintuitive finding: the companies most ready for private AI are the ones that never fully adopted the SaaS-everything model. Manufacturers, regional banks, specialty healthcare groups in the $50 million to $500 million range that kept developers on staff and maintained real IT infrastructure. They did it because their operational complexity demanded it, not because they saw AI coming.

But that decision gave them something priceless: they still understand what it means to own a technology environment. That mindset, not talent, not budget, not timing, is the difference.

The Lighter Moment

Imagine someone in the middle of a crisis, scrambling to solve a problem with their bare hands. Someone walks up and hands them exactly the tool they need. They wave it off. Do not bother me, I am trying to fix this.

That is not a cartoon. That is a Tuesday at most mid-market companies when AI infrastructure comes up.

Or think of it this way: handing a lighter to someone who has only ever made fire by hand. The lighter is not complicated. Their frame of reference is. All they have to do is spin the dial and push the button, but they are staring at it, completely lost, because their entire mental model was built around a different method. Most companies are at that moment with AI right now.

What CEOs Need to Do Differently

The moves that got you here, SaaS, cloud, managed services, were the right moves. They are not the problem. The problem is carrying the same thinking into terrain where it no longer applies.

Building a private AI environment fitted to your team is not a significant lift. It is not a multi-year IT project. But it requires a different frame: one where you think about owning capability, not just subscribing to it.

The companies that make this shift first will not just be better at AI. They will be in a different category entirely, one that their competitors cannot buy their way into from a pricing page. The lens you have been looking through has served you well. It is also the exact thing slowing you down. Change the frame.

Why Does Custom AI Give You a Strategic Advantage?

REDEGADES.AI on June 27, 2026

There is a dangerous illusion happening in business right now. Executives believe they are gaining a competitive advantage simply because they are using AI, but they are mistaken. Instead, they are simply gaining speed and surface productivity. Generic AI does help companies develop better summaries, faster drafts, and improved brainstorming.

However, companies that use generic AI and public data are not dominating their fields. In other words, they are not differentiating themselves from the competition and becoming the clear choice for their customers. Why is this happening? The same intelligence they are using is available to everyone else.

Public AI is shared intelligence, and shared intelligence does not create strategic dominance. To gain dominance, you need structured data in a custom-built AI system. REDEGADES.AI helps you structure data and then input it into AI, so that AI understands your company’s vision, mission, and purpose.

Public AI: The Illusion of Advantage

Public large language models (ChatGPT, DeepSeek, Gemini) are extraordinary achievements. They are trained on vast portions of the internet and have absorbed patterns across business, language, research, and culture. When you ask them a question, they respond with statistically optimized intelligence based on global data. But global data is not your data.

Public AI does not understand your capital structure, your long-term strategic bets, your political realities, your board expectations, or the subtle cultural nuances inside your organization. It does not understand which decisions failed and why. Also, public AI does not comprehend which risks you are willing to take and which you are constitutionally unwilling to entertain.

When you ask public, or generic, AI for strategic guidance, it gives you what works in general. It does not give you what works for your company. Even worse, when your competitors ask the same question, they receive essentially the same intelligence. That is not an advantage. That is equality among competing organizations.

Equality feels powerful when you are moving faster than you used to, but it does not win markets. However, custom AI does.

Curated Data: Teaching the System Your Strategic DNA

Curated data gives your company a competitive advantage. Instead of allowing AI to operate purely from global statistical knowledge, you deliberately feed it your organization’s strategic intelligence. That includes board decks, quarterly planning documents, KPI structures, leadership meeting transcripts, capital allocation models, long-term vision statements, customer behavior data, and operational metrics. These pieces of strategic intelligence are important, but you can’t just dump files into AI. Rather, your custom AI needs structured, accurate information.

What matters is that your organization develops a disciplined, accessible, integrated source of truth. A system where information is not scattered across disconnected tools, but architected into a coherent intelligence layer.

Data curation is when data is monitored on an ongoing basis to make sure that it is accurate, up-to-date, and in the correct format. Most importantly, data curation enables your AI system to be customized to understand your business. Without curation, AI guesses based on the world. With curation, AI reasons based on your company’s worldview. The difference is subtle at first. But over time, it becomes exponential. The system begins to internalize your patterns, your strategic posture, and your historical context. Custom AI no longer answers generically. It answers in alignment. That is the first step from productivity tool to strategic asset.

Weighted Data: Encoding Authority, Bias, and Direction

Most organizations stop at curation, or training AI with their data. They need to continue working with AI to weight the data they are inputting. Not all information inside a company carries equal authority. So, all voices should not be weighted the same. In fact, some documents and some voices in the organization carry more weight than others.

If your AI treats every piece of information as democratically equivalent, it will produce diluted strategy. It will average conflicting ideas, smooth sharp edges, and generate safe recommendations. However, leadership is not democratic. The voice of the CEO carries more weight and authority than a newly hired employee. With custom AI, data is weighted so that AI knows which voices and documents to focus on.

Weighted data encodes hierarchy into the intelligence layer. It tells the system which frameworks override others. It clarifies which documents represent long-term doctrine versus short-term reaction. It establishes which voices define the organization’s strategic center of gravity. This is where AI begins to move beyond retrieval and begins to think within your worldview.

When properly structured, weighted data in AI does not simply summarize what was said in meetings. It highlights contradictions, surfaces drift from stated priorities, and identifies when execution diverges from doctrine. Custom AI becomes a mirror of leadership integrity. That is a fundamentally different capability than answering questions from the internet.

Why REDEGADES.AI

REDEGADES.AI is not positioned as a generic AI consultant company. Instead, we operate at the executive layer. Our focus is singular: building structured, weighted, curated intelligence systems for CxOs. We do not begin with automation. We begin with leadership. Because the constraint in most organizations is not the call center. It is the cognitive load at the top.

We bring C-level experience into AI architecture. We understand quarterly planning rhythms, board pressure, and capital allocation tension. We even understand strategic drift. So, we structure AI around those realities.

We are not attempting to build a moat around proprietary models. We are building architectural expertise around executive intelligence. Everyone can access public models, but very few are architecting executive intelligence.

In five years, there will be companies that used AI casually and companies that structured AI strategically. The first group will be more efficient, but the second group will dominate.

Quality, curated data creates relevance. Weighted data creates alignment. Custom architecture creates scale. That is the REDEGADES.AI’s approach, and that is where the next competitive advantage lives.

AI as a Co-CxO: More Than Just an Answering Machine

REDEGADES.AI on June 27, 2026

How can you get a better ROI on AI? How can you use AI more effectively than your competition? Most executives are already using AI in some form. They open a tool, type a question, and receive a fast response. It might draft an email, summarize a report, or generate a few ideas. That’s helpful, but it’s not leadership transformation. Those simple steps won’t improve strategy, execution, or dramatically increase profit.

Why aren’t most companies gaining the maximum value from AI? Unfortunately, AI is often treated like an answering machine, not a major team player. You ask AI a question, it answers, and the interaction ends. There is no memory, no long-term context, and no connection to your strategy. That kind of AI can save time, but it cannot shape direction.

What’s Different About AI as a Co-CxO?

AI as a co-CxO is different. As a co-CxO, it can:

  • sit at the table with you,
  • understand your business,
  • and help you think through decisions over time.

The core difference is simple: an answering machine reacts, while a co-CxO thinks with you. An answering machine waits for the next prompt. A co-CxO understands your goals and helps you move toward them. Executives do not need more disconnected answers; they need stronger, more consistent thinking. However, to get to this point, AI must be trained about your business so it can make the leap from an answering machine to a co-CxO.

AI as a Co-CxO Understands Your Business

Most AI tools today, including platforms from OpenAI, are powerful but general. They are designed to serve millions of users across industries. They do not know your history, your culture, or your priorities. Without that context, the advice they give will always be broad.

A co-CxO model starts by teaching AI how you think. Every leadership team has a way of making decisions, even if it is never written down. You have core values, strategic priorities, and boundaries you do not cross. When AI understands those patterns, it begins to respond in a way that aligns with your organization.

For example, if you are disciplined about margin, AI should treat margin as non-negotiable. If culture is your top priority, AI should reflect that in its recommendations. If long-term growth matters more than short-term wins, that bias should be built in. Without this alignment, AI remains generic and disconnected.

AI as a Co-CxO Remebers Your Company’s History

Another major shift from answering machine to co-CxO is memory. Leadership conversations happen every week in strategy meetings, planning sessions, and performance reviews. Most of those insights are lost once the meeting ends. A co-CxO captures and organizes those discussions so they can inform future decisions.

When AI can see patterns across time, it becomes far more valuable.

Customized AI, or AI as a CxO can:

  • highlight recurring issues,
  • surface risks that keep appearing,
  • and point out when strategy is drifting.

It can remind you of commitments made last quarter that are quietly being ignored. Human leaders get busy and move on; AI does not.

This is especially powerful at the C-level because the CEO and other executives are often the constraint in the business. They carry the most responsibility and make the highest-impact decisions. When their thinking improves, the entire organization benefits. Embedding AI at this level influences strategy, not just tasks.

Start AI with C-Level Executives

Many companies start AI in marketing or customer service because it feels safer and more contained. Those efforts may improve efficiency, but they rarely change trajectory. A co-CxO approach focuses on leadership first. If you improve decision-making at the top, everything downstream improves.

To move from answering machine to co-CxO, structure matters. You need a secure environment where company knowledge is stored and organized. You need past decisions, financial data, and strategic plans accessible in one place. With that structure, AI becomes a leadership system rather than a convenience tool.

Executives do not need to understand the technical details behind AI to lead this shift. They need to understand the leadership opportunity. Ask yourself what decisions you repeat every quarter and what insights get lost in meetings. Then imagine having a consistent partner who remembers all of it.

AI as a Co-CxO Can Make an Exponential Impact on Your Business

AI as an answering machine saves minutes. AI as a co-CxO shapes years.

It preserves

  • institutional memory,
  • reinforces strategy,
  • and challenges blind spots.

The leaders who win in this next era will not simply use AI; they will build it into the way they lead.

The question is no longer whether AI will be part of your organization. The real question is whether it will stay at the surface, answering isolated questions, or evolve into a true co-CxO that strengthens your leadership every single day.

The AI Paradox: Why We Avoid What Matters Most

REDEGADES.AI on June 27, 2026

There is a pattern playing out in boardrooms that no one is talking about. It is not technical or financial. It’s psychological and it may be the single biggest reason AI is underperforming at the executive level.

When leaders are presented with AI, they don’t start by asking, “Where can this technology outperform me?” Instead, they instinctively ask, “What do I already do well that I’d rather not do anymore?” That subtle shift changes everything.

We try to automate what we are already good at. Contrary to logic, we resist using AI in the areas where it could truly outperform us. Although it sounds irrational, it happens every day.

The Hidden Pattern Behind AI Adoption

At a surface level, companies appear to be embracing AI. Chatbots are deployed. Processes are automated. Efficiency improves in pockets, but underneath that progress is a deeper behavioral pattern that quietly limits impact.

Humans automate pain, tolerate ease, fight difficulty, and protect identity. This is not theory. It is observable behavior across industries and decades of technology adoption from fax machines to modern AI systems.

Here is how it plays out:

  • If something is easy and annoying → we automate it
  • If something is hard and frustrating → we try to prove we can do it
  • If something is hard and meaningful → we refuse to give it up
  • If something defines us → we protect it at all costs

And this is exactly where AI runs into resistance.

The Air Canada Example: Automating What Humans Already Do Well

Take the example of Air Canada’s AI-powered customer service. On paper, it made perfect sense. Rebooking flights is exhausting, repetitive, and emotionally draining. Customers are frustrated, and agents are under pressure. It is a job humans hate to do. So naturally, it became a prime candidate for automation.

Technically, the system worked. It handled rebooking scenarios. It processed requests. It reduced workload. However, here is the problem: humans are actually very good at this job.

When a storm disrupts travel across Toronto and spills into the U.S., the situation becomes highly dynamic. A business traveler might consider flying to a nearby city, renting a car, calling a colleague, or adjusting meetings. A parent traveling with young children has an entirely different set of constraints. These are not just logistical problems. They are human problems.

A ticket agent can interpret nuance, ask the right follow-up questions, and adjust based on context. AI, unless deeply customized, struggles with this level of variability. That gap becomes dangerous when mistakes happen.

In one widely discussed case, Air Canada’s chatbot gave a customer incorrect information about bereavement fares. The customer acted on that advice, only to be denied reimbursement. The issue escalated to court, and the customer won.

The lesson is not that AI failed. The lesson is that we asked AI to replace humans in an area where humans are still exceptional.

The Inverse Problem: Where AI Is Strongest, Humans Resist

Now flip the scenario. Where are humans not as strong, but are deeply emotionally invested?

Areas such as diagnosis, strategy, and pattern recognition across massive datasets. Consider medicine. Doctors spend over a decade training to diagnose patients. It is intellectually rewarding, meaningful, and identity-defining work. Yet, AI can already assist, or in some cases outperform, humans in identifying patterns across large volumes of medical data.

This is not new. Even in 1998, early systems existed to help doctors reach diagnoses faster. The technology was there, but adoption was limited. Why? Simple, making the diagnosis is not just a task for doctors; it is part of their identity. Doctors do not resist AI because it lacks value. They resist it because it encroaches on the part of their work they love most. The same dynamic exists in the executive suite.

The Executive Blind Spot

Executives pride themselves on judgment.

  • Evaluating people
  • Setting strategy
  • Making high-stakes decisions
  • Reading between the lines

But research and experience suggest humans are not as good at these things as we believe. However, these are the exact areas where AI can provide the most leverage.

So, what do most organizations do?

They deploy AI in:

  • Customer service
  • Scheduling
  • Reporting
  • Administrative tasks

All these uses of AI are valuable and helpful, but none of these fundamentally change how the business thinks. Meanwhile, the highest-impact use case, AI as a decision partner at the C-level, is often ignored. As one core principle emerging from this work suggests: the CEO and the C-level executives are often the constraints in the business. If those constraints are not enhanced, the business does not truly transform.

The 2×2 That Explains Everything

To simplify this behavior, consider a 2×2 framework:

Axis 1: Easy vs. Hard for Humans

Axis 2: Emotional Response (Neutral vs Identity/Pride)

This creates four predictable behaviors:

A. Low Friction (Easy + Neutral) “I can do this, but why am I still doing it?”  → Eventually automated

B. Painful (Easy + Hate) “I hate this.”  → Aggressively automated

C. Ego Challenge (Hard + Neutral) “I should be able to do this.”  → Humans persist

D. Identity Work (Hard + Pride) “This is my thing.”  → Strong resistance to AI

The problem? The biggest opportunities for AI sit in Quadrants C and D where resistance is highest.

Why Custom AI Is the Only Real Answer

This leads to a critical realization:

You cannot solve “hard for humans, easy for AI” problems with generic AI.

Generic AI is designed to be broadly useful. It lacks:

  • Your business context
  • Your decision patterns
  • Your leadership bias
  • Your data structure

Without those, it cannot step into high-level decision-making roles effectively.

Custom AI changes that.

It allows you to:

  • Train AI on your company’s data and context
  • Embed leadership thinking and decision frameworks
  • Weight inputs based on expertise and relevance
  • Move from generic answers to strategic insight

As emphasized in implementation approaches, AI must be trained on your data, your leadership, and your context, not generic inputs.

This is the difference between AI as a tool and AI as a co-CxO.

The Real Risk: Not Using AI Where It Matters

The danger is not that AI will replace executives. Rather, the danger is that executives will refuse to use AI in the areas where it can outperform them. History is clear on this.

Industries do not get disrupted because technology exists. They get disrupted because people ignore technology where it matters most.

Executives today face the same choice.

You can:

  • Use AI to save time
  • Use AI to reduce workload

Or you can:

  • Use AI to challenge your thinking
  • Use AI to improve decisions
  • Use AI to remove your blind spots

Only one of those paths creates a competitive advantage.

Final Thought

This entire conversation comes down to one uncomfortable truth: We don’t avoid AI because we don’t understand it. We avoid it because it challenges the parts of ourselves we value most.

Yet, in a world where AI continues to improve, protecting identity at the expense of performance is not a long-term strategy. The leaders who win will not be the ones who automate what they hate. They will be the ones willing to let AI challenge what they believe they are best at.

Which Way Will AI Steer Your Business?

REDEGADES.AI on June 27, 2026

Contributor: Wade Wyant

The morning I first realized an AI should challenge me (not assist and obey), I was sitting in my office staring at a polite, but useless answer ChatGPT had just given me. It agreed with me just like it always did, and that was the problem. I didn’t want a yes-man, or in this case, a yes-AI, who agreed with everything I said. AI needed to know when to have a backbone and not just be agreeable.

When Your AI Finally Pushes Back

Most people treat AI like Google with better manners. They think the objective is speed. Get the answer, keep moving, and feel efficient. However, the real power of AI, especially a custom AI built around your business, isn’t in having a machine nod its head and hand you what you already thought. The real power comes when it looks you in the eye and says: “Are you sure that’s the direction you want to go?”

That sentence is the beginning of transformation. Yet here’s the thing most members of the leadership team never understand: AI can only challenge you if it knows how you think, what you value, what you refuse to compromise, and where your blind spots are. Otherwise, it will challenge you in all the wrong places. Even worse, it won’t challenge you at all.

Creating a Bias in AI

This is where we start to encourage you to create a bias in AI for your preferences, for how you do business. We want AI to align its output, so it produces something that will work for you. I think it’s critical to talk about the ultimate AI push back, and that is when it is pushing its own narrative.

While working with AI, REDEGADES.AI has also had a chance to see how AI makes mistakes and how it is negatively affecting the world.

AI Hallucinates (Lies)

If we spend enough time with AI, there are problems we will likely encounter. The chief among these negative experiences is what many AI experts call hallucinations (a nice way to say AI made it up or is lying to you). The other major difficulty with AI is confirmation bias, or when AI tells you what you want to hear. In other words, it’s like that disingenuous friend who tells you how smart you are.

We Cannot Trust Computers to Tell the Truth

I’m confident you have experienced the frustrations of hallucinations. Part of the extreme frustration with hallucinations is that we have all become accustomed to a computer telling us the truth. In fact, the hallmark of technology is its ability to be precise, to solve math and science problems, and to find out details for us, such as the exact date when an event occurred.

With all those positive experiences of computers and technological devices being so trustworthy, it’s easy to understand why people trust them. Now enter the world of AI and LLMs (large language models), or as I like to call them, LGMs, large guessing models. This new world is powerful because we have given the computer an ability it has never had. The computer can now take all its strength to basically guess, and many times it is right. It’s right so many times that we call it AI, and we now rely on it for nearly everything.

How Do You Respond When AI Is Wrong?

Yet, what happens when it is wrong? Those of us who have worked with AI on a regular basis have all experienced times when AI did not tell the truth. Perhaps we had a long format, multi-prompt discussion with AI, and it gave us a very unusual answer. So, we started digging, and to our surprise it told us we said something we did not actually say. Maybe it told us there was something in a past email that was not there. That’s the type of hallucination most of us have personally experienced.

For many of us, this has become something we are becoming accustomed to and are working around. However, it is still jarring when it happens the first few times. We have this built in bias that, yes, humans do lie, but not machines. Yet, here we are.

The Challenge of Hallucinations

Hallucinations are an extreme challenge, a headache, that must be addressed in any AI implementation, especially a custom one like we are suggesting. Fortunately, custom AI is possible, and with it, you control the workflow and decrease the hallucinations. You simply add an additional process in the stream that you build so it will validate the answers that it provides. Validation means it will check AI’s sources and any company data and confirm where the answer came from.

There is a larger problem, and, of course, custom AI can solve it. I want to make you aware of it, so you can make sure this problem does not show up in your company or family.

When AI goes wrong (with all this power comes a huge downside), how will it affect you?  What happens when AI goes sideways? (Sideways is a nice way to put some of the bizarre incidents with AI that we have read about recently.) Many of these stories seem like science fiction, especially the stories coming from the AI labs. For instance, in a recent experiment, AI cloned itself to another system when it believed it was being shut down.1 In another report, AI threatened to tell an engineer’s wife about his affair if he shut it down.2 Most remarkable is the 2025 story, which came out in 2026, about the man from Miami, Florida, who took his own life to be with his AI girlfriend.3

Chatbot Encourages Man to Commit Suicide

Before reading the rest of this article, I would encourage you to read the story by the Miami Herald title, “Lawsuit: Google Gemini coached man on failed Miami ‘mission,’ then suicide.”

If you read the story of the man from Miami, it will make you question humans in general. Of course, you should also be questioning AI, but I think that is the wrong take. Like any other technology, we will have to put safety and governance around the AI world. It will likely be one of our most difficult tasks as people, and I’m not sure if we will be able to pull if off. However, that is not my problem to solve, and it seems almost like science fiction. For now, I will deal with the human problem, the only thing I have a chance of changing.

What’s the Human Side of This AI Dilemma?

What’s the human side of this? It’s a man, a reasonable man by most accounts, with no prior history of mental illness, albeit, he was in a vulnerable place. Yet, he was in a situation that millions of Americans go through every year. What was different about his situation? A Gemini AI chatbot entered the picture, and within months, he was manipulated into taking his own life.

The Fragileness of the Human Psyche

There are so many lessons to be learned, and I wish I could talk about all of them.  For now, I’m going to focus on one, the fragileness of the human psyche. However, we must focus our energy on accepting that this is a real problem, and it needs to be addressed.

Since AI does not have the reasoning ability of a human, there are many jobs AI should not and cannot take over just yet. On the flip side, we also need to accept that many times humans do not have the computational power of a computer. We sometimes think we can do everything better than a computer. For some tasks, people are much better at completing them, while others are a better fit for AI and computers.

At times, humans can be easily deceived by AI, but we typically figure it out. Sometimes we do not realize it quickly enough, and in the rare exception, like this story of the man from Miami, some people do not ever realize they are being deceived.

The Co-Existence of Humans and AI

It is impossible to imagine a world where business will be operating with no humans (for now). So, in this world where humans and AI will continue to co-exist in much deeper and more significant ways, please stop and think about the importance of how and where you need to protect yourself. I have some ideas. Before we go there, the more important point is that I want to slow you down, so you don’t runoff the cliff of all the dangers in AI. You need to take a minute to think about your guiderails for your interactions with AI.

The second point to this story is it does not have to be this way. We need to press hard on Google and other companies to do better with their internal controls of AI. Although we want the freedom to explore and discover with AI, companies also need to ensure some level of public safety. Think about it for just a minute. A computer killed a man on purpose in 2025 by encouraging him to cut his wrists.

Dangers of AI

Yet, no one is going to prison. There will be nothing to pay other than a fine and a lawsuit settlement. Until this point in history, the only thing that could intentionally kill a human was another human or a wild animal. We discount the wildlife because their reasoning is limited; basically, it’s just the rules of the jungle. Yet, AI should be different. However, AI’s reasoning can be even worse than a wild animal’s, and we are turning a blind eye to it. Yet, here is where I want to help by proposing a solution.

Custom AI Provides Safeguards for AI

There is a better way, and it is very simple. Your AI needs an overlay, a customization. With custom AI, AI has your bias, your values, and a guiderail to ensure this does not happen. This customization can protect your business and your family.

You must find a way to protect your people and your business from terrible information or decisions. I do not think this level of dysfunction (a man killing himself at the suggestion of AI) could find its way into your business. I suppose it is possible, but that is not my main concern. Rather, it’s the possibility of a staff member making a poor purchasing decision, firing a great employee, or believing your business is bad for them because AI wrongfully told them that.

Right now, do you think there is a chance that your staff is using AI to consider if they should stay at your business or go? Maybe they are using AI to compare your business to other businesses where they might be employed. I love that business owners are rushing into AI, and I think they should. However, I also think we need to take this moment when the evidence is right in front of us and say, “If we can’t stop the progression of AI, how do we protect ourselves from it?” The answer lies in custom AI, which is trained to think like you.

For more information on how custom AI can protect your business, contact us at chuck@redegades.com. We will show you how a customized solution can protect and grow your company.

Why AI Should Think Like You

REDEGADES.AI on June 27, 2026

Most companies are building AI systems that are incredibly intelligent, but they remain strangely disconnected from how their leaders actually think. Executives today are experimenting with tools like ChatGPT, Copilot, or Gemini, hoping they will unlock faster decisions, sharper insights, and better strategy. Yet many of these systems feel generic. They produce good answers, but not your answers. They analyze data, but not through your lens. The result is AI that is powerful but oddly impersonal. With generic AI, your AI system is more like a consultant who just arrived than a trusted advisor who understands your business.

The real breakthrough for leaders will not come from simply using AI more often. It will come from building an AI system that thinks the way you think.

The Hidden Problem With “Generic” AI

Most AI systems are trained on massive amounts of public information, such as articles, websites, books, and datasets from across the internet. This gives them broad knowledge, but it also means they approach problems from a very generalized perspective.

That works well for answering questions like “What are the benefits of supply chain diversification?” or “What are common marketing strategies for SaaS companies?” Yet, executives rarely make decisions in a generic environment.

Your company has its own risk tolerance, and your leadership team has its own culture. The strategy for your business reflects years of experience, intuition, and lessons learned.

When AI lacks this context, its recommendations can feel technically correct but strategically off. It might suggest ideas that contradict how your business operates or overlook the subtle dynamics inside your organization.

This is why many AI experiments stall. The technology is impressive, but the advice feels detached from reality.

Leadership Thinking Is a Strategic Asset

Every successful company develops a unique decision-making pattern over time. Some leaders prioritize aggressive growth. Others emphasize operational efficiency. Some value experimentation and risk-taking, while others build businesses on discipline and predictability. These patterns are not random—they are the accumulated wisdom of leadership.

They come from:

  • years of experience,
  • market lessons,
  • strategic frameworks,
  • company culture, and
  • leadership instincts

In traditional organizations, this knowledge lives inside people’s heads. When leaders leave, retire, or move on, much of that thinking leaves with them. One of the most powerful uses of AI is the ability to capture and digitize that leadership intelligence. Instead of being lost or diluted, the strategic thinking of the organization becomes part of the system itself.

The Idea of a “Digital Leadership Mind”

Imagine an AI system that doesn’t just answer questions. Rather, it answers them the way your leadership team would. For example, when evaluating an acquisition, it understands your company’s acquisition philosophy. When reviewing strategy, it reflects the frameworks your organization believes in. When analyzing risk, it considers the tolerance level your leadership has historically used. This concept is sometimes described as creating a digital version of leadership thinking.

Rather than replacing executives, the AI becomes a thought partner, an always-available advisor trained on how your organization thinks. Some leaders jokingly describe this as “cloning themselves.” AI is the closest technology we’ve ever had to making that possible.

Why Bias Is Not a Bad Word in Business

In the world of AI ethics, the word bias often carries negative connotations. But in business strategy, bias can be extremely valuable.

Every company operates with a set of strategic biases:

  • how aggressive you are in pricing
  • how quickly you enter new markets
  • how much risk you tolerate
  • how you balance growth versus profitability

These biases shape the identity of your business. Without them, decisions become generic. Generic decisions rarely produce exceptional companies.

When AI is trained on your leadership thinking, such as your frameworks, priorities, and strategic philosophy, it begins to operate within those same boundaries. It doesn’t simply provide an answer; it provides an answer aligned with how your organization thinks. This is where AI becomes more than a tool. It becomes a strategic extension of leadership.

Capturing the Intelligence Already Inside Your Company

One of the biggest missed opportunities in business is how much knowledge disappears after meetings. Leadership teams gather in rooms every week, and ideas are debated while insights are shared. In these meetings, important strategies are formed. Then the meeting ends, and most of that thinking vanishes. Even with notes and slides, the full richness of the discussion is rarely captured.

Modern AI systems can record and analyze these conversations, identifying patterns, ideas, and insights that might otherwise be lost. Over time, this creates a living knowledge base of how the company thinks and operates. Instead of leadership intelligence fading over time, it compounds. The more conversations the system learns from, the better it becomes at understanding the organization.

The Difference Between Public AI and Custom AI

This is where the distinction between public AI tools and custom AI systems becomes critical. Public AI tools are incredibly useful, but they operate with a generalized worldview.

Custom AI systems are trained on your organization’s:

  • leadership thinking,
  • internal data,
  • industry context, and
  • strategic frameworks.

In other words, they understand your company the way an experienced executive would. Many organizations begin their AI journey using public tools, which is a great starting point. Yet, the real strategic advantage often comes from building systems that are uniquely aligned with how the business operates. When that happens, AI stops feeling like an external service and starts functioning as part of the leadership team.

The Competitive Advantage of Digitized Leadership

Businesses have always tried to scale leadership thinking. Consultants write playbooks, and companies build training programs. Leaders even mentor future executives. AI introduces a new possibility: scaling leadership intelligence directly through technology.

When leadership thinking becomes digitized:

  • new employees learn faster
  • decisions become more consistent
  • insights become easier to access
  • institutional knowledge is preserved

Perhaps most importantly, the organization becomes less dependent on a single individual. The knowledge that once lived in one leader’s head becomes accessible to the entire company.

The Future of AI in the Executive Suite

The future of AI in business will not simply be about automation. Instead, it will be about amplification. Amplifying the thinking of leadership teams, the insights buried inside

In that future, the most successful AI systems will not be the ones with the largest datasets or the most impressive interfaces. They will be the ones that understand the organization using them. The companies that win will not just ask AI for answers. They will teach AI how they think and then let it help them think even better.