Multi-modal and multi-generational
Issue 239: When generations shift and machines speak: a new era of leadership and intelligence
We are in a unique shift in tech right now. The world seems to be changing rapidly with AI advancements. Interactions are not a singular text conversation, but multi-modal inputs. We are amid a generational hand-off between Millennials who grew up with the internet, and Gen Z, the first digital native generation.
I’m one of the first-wave Millennials—essentially a prototype with Gen X attributes. I had a Walkman and a MySpace page. My cultural influences came not just from peers, but from older siblings and their VHS tapes, Napster accounts, and MTV. Many of us in this micro-cohort had the experience of being the youngest in the room, until one day, we weren’t. We are entering a truly multi-generational era of technology that mirrors the rise of multi-modal AI.
This isn’t a one-way transmission of wisdom from older to younger. The most impactful organizations will be the ones that facilitate learning in both directions. Knowledge must flow upstream and downstream. Gen Z and Alpha bring a native fluency in new interaction paradigms that older generations often struggle to understand. In turn, Millennials, Gen X, and Boomers bring historical context and hard-earned pattern recognition.
“We’re no longer building for a single generation. We’re no longer operating in a single mode.”
Key elements of the generational transition
First, there is a leadership succession at technology companies between Gen X and Y to Gen Z (then to Alpha). Each generation also has different ways of interacting with technology. For Gen Z, AI might be their iPhone moment. In addition to interactions, the capabilities shift with how they interact with multi-modal as a default. Finally, all these shifts need the documentation and distribution of knowledge.
Leadership succession
The majority of leaders in tech today are in their 40s, 50s, and 60s. Their wisdom is valuable, but their tenure is finite. Over the next decade, we’ll see thousands of executive roles become vacant as this group retires or transitions into advisory roles. The question isn’t just who will replace them—it’s how we prepare those who will.
Mentorship can’t be transactional. Speed-dating-style Zoom calls won’t cut it. We need deeper systems of apprenticeship. Structured pathways for knowledge transfer. And maybe most importantly, a culture that respects curiosity regardless of title or tenure.
New interaction paradigms
At Config 2024, Jiaona Zhang (JZ) gave a talk on how to build for, and with, Gen Z. Her insights revealed just how different the expectations and behaviors of this generation are. They’re less hierarchical, more socially conscious, and deeply fluent in short-form, visual, and reactive communication. They don’t want friction, but they crave authenticity. If you're designing products or teams, it's essential to understand what motivates this generation. Reports like the Deloitte Global Gen Z and Millennial Survey (2024) and McKinsey’s research on Gen Z show how values like mental health, purpose-driven work, and social awareness drive decision-making for younger professionals. If you’re building products and services today, you’re not just adapting to a new interface—you’re adapting to a new philosophy of interaction.
Multimodal AI is the new default
At the same time this generational change is underway, we’re also experiencing a shift in machine interaction. AI is no longer just text-based—it’s now visual, auditory, conversational, and contextual. What’s known as multimodal AI is becoming the new default.
The GPT-4 architecture introduced a model that can take both images and text as input. Tools like Runway, Midjourney, and Perplexity show how creativity and computation are converging. We are no longer asking machines for answers—we are co-creating with them. Multimodal AI is not just a new interface—it’s a new collaborator.
Understanding how different generations interact with these tools is vital. For Gen Z and Alpha, multimodal interaction isn’t new—it’s expected. For older generations, there's still a mental model shift to embrace: thinking beyond keyboard inputs and towards prompts, gestures, and hybrid modalities.
Sharing knowledge across generations
The Knowledge-Creating Company by Ikujiro Nonaka is one of my favorite all-time reads. It talks about how organizations don’t just store knowledge—they create it through continuous, shared dialogue. That’s the mindset we need now. The goal isn’t to preserve knowledge in amber—it’s to pass it along in a way that the next generation can remix. We need shared documentation, yes. But also shared memory. Retrospectives, storytelling, rituals. And perhaps most critically, openness to having our assumptions questioned by those just getting started.
Call to action
If you’re like me, and you are towards the end of your career, this is your moment to pass your knowledge.
Mentor deeply, not casually. Commit to long-term relationships with future leaders. Don’t just give advice—give context, give stories, give space.
Adapt your leadership. The way you led in 2010 won't work in 2025. Learn the languages of Gen Z and Alpha. Pay attention to how they work, communicate, and ideate. Help shape their future, not repeat ours.
Stay curious. Multi-modal AI isn’t just a new tool—it’s a new canvas. Play with it. Let younger teammates show you how they use it. We’re all beginners again, and that’s a good thing.
This is a rare moment of dual transformation: one in human leadership, and one in machine intelligence. Let’s not let it pass without intention.
As a proud GenXer, I appreciate the reminder that we need to step up and share our knowledge and skills...and continue to learn from all individuals, not just those who came before us.
I think you are one of the best futurists in forecasting the new interface.💯