When Technology Becomes the Story

When social media first became a thing companies felt compelled to “do,” it was usually handed to the most junior person on the team.

They understood the platforms. They knew how they worked. That part made sense.

It also revealed a pattern that has repeated itself across every major technology wave since: the dot-com era, SaaS, and now artificial intelligence. Each time, a new system enters the organization and begins reshaping how people are evaluated — before anyone explicitly agrees that it should.

Fluency with the tool begins to carry more weight than familiarity with the business.

Not because leaders decide experience no longer matters, but because facility with the technology looks like adaptation at a moment when uncertainty is high. And in uncertain moments, organizations reach for signals that feel legible and immediate.

When Fluency Becomes a Proxy for Judgement

Those early social media assignments rested on an implicit assumption: that proximity to the medium translated into the ability to use it effectively on behalf of the business.

In practice, many of the people doing the work lacked context – revenue models, customer economics, product positioning, or a clear definition of success. Activity increased. Metrics proliferated. But they weren’t tightly connected to outcomes the business actually cared about.

The issue wasn’t age or seniority. 

It was alignment.

Facility with the medium became a stand-in signal for the ability to apply it in service of business objectives. Fluency was mistaken for understanding.

How This Shows Up In Careers

I’ve written about this at the company level before; what’s changed is how clearly it now shows up in how people are evaluated.

This dynamic doesn’t stop at the organizational level. It shapes how individuals learn to present themselves.

When tool fluency becomes a dominant signal, people adapt to what gets recognized. Resumes fill up with platforms, certifications, and technologies. Conversations drift toward how work gets done rather than what problems are being solved.

Over time, this changes incentives: 

• Being current feels safer than being right.

• Listing tools gets more traction than explaining tradeoffs.

• Fluency is simpler to demonstrate than judgment.

Business understanding - how decisions compound, where constraints sit, what second-order effects matter, product intuition, and role mastery don’t compress neatly into bullet points.

Tools do.

This creates a quiet tension for individuals who have depth, whose value lies in context and judgment but don’t lead with novelty. Their value doesn’t vanish, but it becomes less visible — not because it’s lower, but because it’s harder to surface.

Over time, people adjust. Some chase every new platform. Others lean harder on titles or tenure. Both are attempts to remain legible in a system that rewards immediacy and recognizability, in an environment that confuses signals with substance.

This is how a business-level bias turns into a personal one.

How Business Reality Gets Crowded Out

This same dynamic appears in nearly every technology wave. Comfort with the new system begins to shape hiring decisions, performance evaluation, and trust. Experience with the underlying business, product, or role carries less visible weight.

Over time, the story about what matters starts to drift.

Not because experience becomes irrelevant, but because experience tends to surface constraints, tradeoffs, and context that don’t compress easily into signals. Technology narratives do. They promise leverage, speed, and clarity.

• Organizational attention shifts.

• Job descriptions emphasize tools. 

• Evaluation tilts toward fluency. 

Signals of being “current” become easier to recognize than evidence of sound judgment.

The shift is subtle. Its consequences are not.

When  Business Reality Pushes Back

For a time, this works well enough. Tools get adopted. Teams move faster. Output increases.

Then limits emerge. 

Strategy weakens. Second-order effects are missed. Execution outpaces understanding. The business reasserts itself, often through missed expectations or brittle decisions, or outcomes that fail to justify the activity that produced them.

At that point, experience becomes valuable again — usually after it has been discounted.

AI didn’t create this pattern. Social media didn’t either. They are simply the latest contexts in which it’s visible.

Berkson's Bits

Creative pursuits -- the process of building something genuinely new -- requires you to be comfortable with uncertainty.  

That uncertainty is what forces the mind to form unexpected connections.  It allows ideas to emerge not merely because they are novel, but because they feel purposeful — important, interesting, elegant, clever, or even playful. 

Creation is not just about originality; it is about intention.

Generative technology can be simplified as being based on statistical probabilities: predicting what is most likely to come next based on what has come before.

This makes it powerful. It also makes it different.

What it does not supply is purpose. It does not decide what is worth making, or why something should exist at all.

That judgment — about meaning, relevance, and consequence — remains human.

Perhaps that sense of purpose is not a limitation of technology, but a reminder of what creativity, and leadership, ultimately depend on.

What I'm Listening To...

Nearly half of this year’s Grammy nominations for Song of the Year went to covers or samples. If you want to discuss what that means for music, hit me up. 

My favorite cover earned a nomination for Best Jazz Performance. Here's a beautiful cover of the Miles Davis classic"Four" by Michael Mayo.

This is not an argument for resisting new tools. I’ve never believed that was the right move.

It is an observation about how easily fluency gets mistaken for understanding when things feel uncertain. And how often the business has to remind everyone — later — that those aren’t the same thing.

I don’t have a clean solution for this, and I’m not sure there should be one. 

It always does. 

And usually later than we’d like.

Looking forward to continuing the conversation…
Alan