In network security, the “Handshake” is the critical moment when two systems verify each other before exchanging a single byte of data. It’s a negotiation. Are you who you say you are? Do I trust you? What are the rules of engagement? If the handshake fails, the connection drops immediately.
For the Baby Boomer generation, the Handshake isn’t just a line of code or a TCP/IP concept; it’s the fundamental unit of trust.
We like to mock the Boomers in tech. We make jokes about them printing out emails, leaving voicemail messages, or typing with one finger. But in my years as an engineer, I’ve learned something important: They know who to trust. And in an era of deepfakes and AI hallucinations, that instinct is becoming valuable again.
The Rolodex vs. The Algorithm
Boomers built their careers in an era where “Network” meant people, not cables. They verified information by looking someone in the eye, by checking references personally, not by reading a generated summary.
This makes them the “Reluctant Adapters” of AI, and honestly? We need that resistance.
When a Gen Z kid sees a deepfake video of a CEO announcing a merger, they might laugh at the glitch or accept it as “content.” A Boomer executive asks a different question: “Who authorized this? Is this real? Get them on the phone.”
They value Provenance. In a world where generative AI can produce infinite variations of plausible-sounding nonsense, the Boomer instinct to “verify the source” is closer to a strict Zero Trust cybersecurity architecture than most of the software products sold today. Zero Trust means “Never Trust, Always Verify.” That is the Boomer motto.
Privacy is not a Setting; It’s a Right
There is also a profound difference in how they view privacy. Boomers grew up with the shadow of the Cold War. They understand the concept of surveillance states. They are deeply, instinctively suspicious of “free” tools that track their location or read their keystrokes.
While todays kids are happily trading their biometric data for a funny Snapchat filter, the Boomer executives are asking the hard questions during vendor risk assessments:
- “Where does this data sit geographically?”
- “Who owns the IP rights to my queries?”
- “Can I delete this permanently?”
They aren’t being difficult; they are being secure. They act as a breakwater against the erosion of privacy. They prefer “Invisible AI”—the kind that works in the background like fraud detection at the bank or automated spam filters—over the “Chatty AI” that asks for their life story.
If an AI assistant tries to be too friendly (“Hi! I noticed you bought a ticket to New York!”), a Boomer doesn’t feel delighted. They feel stalked.
The Voice on the Line
If you want to sell to this demographic—and you should, because they still control a massive amount of corporate budget—you have to change your protocol.
Pick up the phone.
It sounds archaic to a 25-year-old Sales Rep who lives on LinkedIn and Slack. But for a Boomer, a phone call is a signal of respect. It shows you represent a real entity. It shows you are willing to invest real-time, not just automated-sequence-time, in understanding their problem.
They don’t want a “Customer Portal.” They don’t want a Wiki. They want a “Guy.”
“I have a guy for IT.”
“I have a guy for plumbing.”
They want to be able to say, “I called Ed, and he fixed it.” That personal accountability is the only SLA (Service Level Agreement) they truly believe in.
The Future is Concierge
The irony of the AI age is that the Boomer preference for human connection is quickly becoming the ultimate luxury good.
As we automate everything for the mass market (chatbots, self-service kiosks, AI agents), the ability to sit down, shake hands (or bump fists), and listen without a screen in between is becoming a premium service. It’s also something the younger generations struggle to actually do well.
We are seeing a divergence. Low-cost services will be tech-first. High-value services will be human-first. Boomers have demanded “Human-First” their entire lives, and the market is circling back to them.
The Takeaway: Be Human
Don’t force them into the chatbot. That is a churn event. Invite them to the table.
If you effectively bridge the gap with a Boomer, you gain a loyalist for life. They don’t churn because a competitor offered a feature that was 10% cheaper. They stick with you because they trust you.
In a world of ephemeral clicks and one-time transactions, that loyalty is the most stable asset you can have. They are holding the line on humanity. Don’t fight them on it; join them. You might learn exactly how the system actually works when the power goes out and the cloud evaporates.