AI, Identity & Empathy
Human-Centered Intelligence for a Fragmented Age
Essays that examine how AI interprets identity, where it fails, and what it takes to build systems that understand people with accuracy, dignity, and emotional truth.
There are moments when your voice becomes impossible to ignore. This is the story of how pressure clarified my purpose, sharpened my leadership, and revealed the future I am built to lead in.
When Amazon bought Whole Foods, everyone predicted Instacart’s collapse. Instead, the grocery industry spent years chasing the wrong infrastructure—and is now retreating from automation, robotics, and self-distribution. Instacart’s flexible, store-proximate model didn’t just survive; it became the design pattern grocers are returning to.
AI doesn’t fail queer and BIPOC people because of “bias.” It fails because it cannot interpret our identities with accuracy, context, or cultural truth. This essay reveals the mechanisms behind that harm and introduces a new architecture to prevent identity collapse in the age of autonomous AI.
Amazon doesn’t have a convenience problem.
it doesn’t have a speed problem.
It doesn’t have an assortment problem.
Amazon has a discernment problem.
People don’t remember flawless. They remember feeling seen.
They remember the human who made the stress smaller, the journey lighter, the moment calmer. They remember the person who didn’t just process them, but acknowledged them.
Travel, at its core, is a human ritual. It is migration, reunion, escape, reinvention, obligation, hope. And any airline that forgets that truth — even unintentionally — begins to lose the one thing technology can’t replicate: emotional resonance.
This one was hard to write. Not because I’m mad. Because I still want the blanket.
For years, Target was the rare brand that made belonging feel casual. You’d walk in for toothpaste and walk out with a little affirmation tucked into your bag. Pride wasn’t seasonal — it was spatial. It lived in the aisles, woven into the colors, the tone, the quiet promise that this place sees you.
And then, 2023 happened. The backlash. The retreat. The silence.
When Target pulled its Pride collection, it didn’t just move product — it moved meaning. It told queer people what we’ve always half-suspected: our safety here was situational.
This isn’t about outrage. It’s about empathy debt — the emotional residue that builds when remorse never matures into reflection. You can’t pay it off with apologies. You pay it off with change.
For years, Nintendo has been the moral compass of interactive entertainment.
A company that taught the world that joy could be engineered, and that simplicity could feel transcendent.
They’ve spent decades proving that technology doesn’t have to exploit emotion to move people. It can honor it.
That’s why their recent stance on AI — a public commitment not to use it in game design — is so fascinating. Because in one sense, they’re right.
And in another, they’re missing their greatest opportunity yet.
I wrote AI, Craft & the Human Future of Retail because I’ve come to believe the real disruption of AI isn’t technical — it’s human. After years leading transformation work with Tredence and SymphonyAI, I watched automation accelerate faster than reflection, and intelligence scale faster than intention.
This paper is my attempt to restore that balance. It introduces The Knox AI Empathy System — a model and a mindset for designing organizations that think with care. It’s not about faster machines; it’s about wiser leaders.
Because in an age where intelligence is abundant, discernment has become the rarest skill of all.
A few weeks ago, OpenAI announced that users could now buy directly inside ChatGPT. No checkout page, no app handoff, no cart abandonment halfway through a funnel. Just a conversation, a suggestion, and a sale.
At first, it sounded like novelty — a new way to shop without leaving the chat. But beneath the surface, it marks something far deeper: the beginning of agentic commerce.
As I prepare to leave SymphonyAI and step into a new chapter, I’ve been reflecting on these quiet moments and the lessons they hold. This past week, I’ve been deeply moved by the kind words of colleagues and clients who’ve shared how my work impacted their own. These conversations reminded me of something we often forget: we are far more exceptional than we give ourselves credit for.
The best leaders aren’t the ones with the fanciest titles or the slickest presentations. They’re the ones who show up for their people—consistently, authentically, and with purpose. Next time you notice something isn’t quite right on your team, skip the analysis and just talk to the person. Be curious. Be honest. Be human. Great leadership isn’t about strategies or optics. It’s about showing up for the people who make it all happen.
AI has become a household name in the world of creativity. It’s helping artists design stunning visuals, musicians compose new melodies, and writers craft stories. But let’s be honest—many of us still feel a little uneasy about it. Can a machine really understand creativity? And even if it can help, what does that mean for the uniquely human magic we bring to the process?
The AIM Loyalty Framework (AI-Integrated Maturity) draws on the strengths of industry-leading models while addressing the unique needs of loyalty programs in retail, hospitality, finance, and beyond. It’s a tool designed to help businesses move beyond generic AI strategies and build programs that foster meaningful customer relationships, deliver measurable ROI, and set new standards for innovation.
Imagine planning a dream vacation where every recommendation feels custom-made for you, yet you never have to give up your personal data. Sounds too good to be true, doesn’t it? It’s not—thanks to the rise of Customer-Centric AI, a new approach to artificial intelligence that promises to deliver exceptional, tailored experiences while respecting privacy.
AI is reshaping CSR initiatives in ways that benefit both business outcomes and society at large. This blog post explores why retailers must embrace AI-driven social responsibility and dives into five innovative AI applications that can drive impactful change.
As the grocery industry faces increasing pressure to address sustainability concerns, Artificial Intelligence (AI) offers transformative potential. By leveraging AI to optimize operations, reduce spoilage, and make data-driven decisions, grocery retailers can substantially reduce food waste while improving profitability.
While traditional Point-of-Sale (POS) data has been useful for tracking transactions, customer data holds far greater potential for driving business growth and building long-term loyalty. The retail giants—Kroger, Amazon, and Walmart—have demonstrated the transformative power of leveraging customer data, not just to enhance the shopping experience but also to drive new revenue streams.
Retail is no longer just about selling products—it's about creating experiences, building connections, and staying ahead in a constantly evolving digital landscape. To thrive in this environment, retailers need more than just good products—they need a strategic framework to guide them through the complexities of digital transformation.
The Supermarket News article dismissing grocery price controls lacks a valid path forward, relying on theoretical arguments without concrete industry data. While free markets have driven economic growth, they rarely reverse inflation in healthy markets. Hyland's reliance on general economic principles and historical examples, like the 1970s gas crisis, weakens his argument against price controls, leaving it speculative and unsupported by current evidence.
In the mid-20th century, BIC was widely recognized as a leading manufacturer of pens. However, a transformative shift occurred when BIC began to see itself not just as a pen maker, but as a manufacturer of plastic goods. This strategic pivot was a game-changer for BIC, illustrating the power of reimagining a company’s identity to unlock new opportunities.
Today, OpenAI stands at a similar crossroads. OpenAI has the potential to redefine its role in the tech landscape in a way that mirrors BIC's transformation. The question is not if, but when, OpenAI will evolve from being an AI innovator to becoming a leading provider of data and insights across industries.
In a recent article, Kinjil Mathur, the Chief Marketing Officer (CMO) of Squarespace, shared her unconventional journey to success, which began with cold-calling companies listed in the Yellow Pages to land unpaid internships (Royle). While her story is inspiring, it raises important concerns about the implications of promoting unpaid work and the hustle mentality. This blog post explores the potential negative aspects of Mathur's advice and offers solutions to mitigate these risks.
In response to the Harvard Business Review article, "Why Great Employees Leave Great Cultures," this post explores the crucial role of organizational and leadership credibility in employee retention. In today's competitive job market, retaining top talent goes beyond offering attractive perks or competitive salaries. The core of employee retention lies in organizational and leadership credibility. When words align with actions, it builds a foundation of trust and respect, essential for a thriving workplace culture.
When Stop & Shop’s leaders list these stores as “underperforming” - what does that mean? I think it is safe to say competitive pressures would contribute to a stores closure, and a merger of their two biggest grocery rivals would certainly not benefit them.