The Conviction Gap

Before there were seasons, there was one room

On June 11, 2015, I brought C-suite and senior executives from more than 20 Fortune 500 companies to the Marriott in Irvine, California, for an invitation-only summit called Preparing U.S. Leadership for the Seismic Cultural Demographic Shift. CVS Health hosted and sponsored it, with Aramark and The Axis Agency as supporting sponsors. Magic Johnson and Mike Fernandez led the featured roundtable.

The day was framed around markets and demographic groups. Yet listen to what the speakers actually said. Magic Johnson: “You can’t have a cookie-cutter mentality, you have to tailor your approach.” CVS Health said its pharmacies “should not be one size fits all for the diverse communities we serve.” Dr. Joseph Alvarnas of City of Hope described two paths for healthcare: one “intensely personal,” the other “highly regimented,” a path that “disenfranchises the very people we are seeking to serve.”

To me, Magic Johnson’s business was the first proven commercial example of what happens when you practice personalization in the workplace and the marketplace at the same time. His theaters hired from the communities they served and adapted what they sold to local tastes. He didn’t create demand. He recognized the demand that was already there because he took the time to know the people.

Four years before the first season, the first room was already describing the choice between serving the average and serving the person. The gap was there too. In my Forbes interview with CVS Health that spring, the verdict was blunt: “the vast majority of organizations are still slow to act.”

The 2015 room talked about groups. Every room after it kept arriving at individuals. City of Hope, represented that day by Dr. Alvarnas, went on to host the first season in 2019 and to serve as premier sponsor through 2023.

My own thinking shifted too. In 2015, I framed the Cultural Demographic Shift through diversity and inclusion. Then I watched organizations turn that conversation into categories, labels and silos. They treated each person’s differences as a threat to standardization rather than an opportunity, and reached for control instead of giving people the freedom to share their own point of view. Instead of harmony, standardization and personalization drifted to the extremes, and the extremes divided us. That is when my focus moved from the group to the individual.

“It’s no longer about the institution defining the individual. It’s about the individual defining the institution in search of a shared mission.”

That room inspired my next book, The Innovation Mentality (2017), and that line, one of my most quoted. By 2018, the second part of my Forbes series on inclusion carried a new title: Leadership in the Age of Personalization.

I wrote it down, then I tested it in nine rooms

The books came first. Each summit was designed around the book I was writing, and each room became a place to test what I had put on the page. My team at Glenn Llopis Group designed and produced every season. I built the content strategy, prepared every speaker, and facilitated and moderated the conversations.

After the 2015 prologue, nine seasons followed. Six brought together leaders across sectors. Three focused on healthcare, where the cost of treating people as averages is measured at the bedside.

The timeline below shows how the four layers of the record line up: the books, the Forbes columns, the rooms and the essays that followed. Every item is dated, so the sequence can be checked rather than taken on faith.

The Forbes column on the Cultural Demographic Shift came a year before the prologue and five years before Season 1, and the books I was writing framed every season that followed.

The status quo fights back: why I stopped the summits

I stopped the summits because agreement had become the outcome. Leaders came, nodded, shared their stories with real honesty and went back to institutions that rewarded the old way. They agreed with the idea. They were afraid of what acting on it would cost them.

The clearest moment came in Puerto Rico in January 2025. After the forum, an executive told me starting the transformation felt complicated and overwhelming. I asked him whether it was complicated or simply uncomfortable. He went quiet. That silence told me more than anything said on stage.

“Complicated” is often the word we use for “uncomfortable.”

I had written about this resistance before the first room ever met. In 2019, I warned that the status quo fights back when you threaten it, and that senior leaders resist change out of fear of being vulnerable. The rooms proved it, season after season. It isn’t that leaders don’t see the problem. It’s that seeing it puts them in a position they would rather not occupy.

The resistance wasn’t limited to the rooms. In January 2025, I wrote a Forbes column about where diversity, equity and inclusion had lost its way in many workplaces. Forbes pulled it. I won’t speculate about why. I rebuilt it for my own platform as Inclusion Can’t Be Enforced. It Has to Be Fostered. Its central line still holds: “When people feel sorted rather than seen, they pull back.”

Another season of agreement wouldn’t close the gap. Leaders didn’t need more convincing that individuals matter. They needed the conviction to act on what they already believed, and conviction has to be earned one person at a time. That is where my work went next.

Standardization on steroids: why AI widens the gap

AI is standardization on steroids. It learns the average of everything we have done before and hands it back at a speed and scale no institution could ever reach. For people who know who they are, that is a gift. For people who don’t, it quietly decides for them.

Standardization was never the enemy. It made organizations efficient and gave work its consistency. The problem began when we came to believe that conformity is synonymous with efficiency, and rewarded people for fitting the mold instead of contributing what only they could. The nine rooms showed what that belief cost. AI now turns it into infrastructure.

I have been writing about this throughout 2025 and 2026, in Forbes and in my Conviction Chronicles essays:

• In April 2025, I wrote about the AI trap and what it takes to stay unique and irreplaceable.
• In May 2026, I wrote about keeping your authentic identity in the age of AI.
• In healthcare, I warned that AI “can just as easily become the most powerful standardization engine healthcare has ever built” (AI Is Handing Patients Back Control of Their Care).
• In the workplace, I wrote that “the economic value of standardized human capability declines” as AI absorbs it (In the AI Economy, the Floor Is Falling and the Ceiling Is Rising).
• And I wrote that AI “could erase what makes you valuable if what makes you valuable is the standardized version of your work” (You Are What the AI Efficiency Calculation Leaves Out).

Here is why this widens the conviction gap. AI amplifies whoever is doing the asking. A person with conviction brings judgment to the machine: what matters, what to question, what to keep. A person who has spent a career editing themselves to fit brings the edit. The machine returns the average, and they accept it because they have nothing of their own to hold it against.

That is the situation many institutions are in today. They are betting on AI with people who were never given the chance to know who they really are. Without that, those people lack the judgment to use the machine with conviction. The 87 percent of managers who say their individuality is suppressed at work are now being asked to direct a technology that rewards exactly what they were taught to hide.

In my essay on hollow confidence, I described what this looks like from the outside: “a conviction gap, dressed up as confidence.” AI will make that costume easier to wear and harder to see through.