It's Not You. It's the Software.

By Leah Clelland Jochim | Convergence Technology Solutions & L&T Ventures

I was in a room recently with a group of brilliant young women.

They were thoughtful, capable, and doing important work. And yet, one by one, they started apologizing — for not "getting" AI fast enough. For not using it well. For feeling behind.

I've heard this before.

Not just recently. Decades ago.

We've Been Here Before

I didn't set out to work in technology.

I was a history co-op student at the University of Ottawa, planning to become a diplomat or teacher so I could work overseas. But during two of my placements, I found myself helping research and write for the Canadian federal government's first electronic bulletin board system.

At the time, I found computers interesting. I knew a bit of BASIC and Pascal from high school. But I wasn't pursuing a career in tech.

And yet, there I was — learning what it meant to publish information digitally and communicate at scale.

A few months later, in 1993, Mosaic was released and the World Wide Web began its shift from a technical domain into something public. Our team moved from BBS to web, and soon we were helping federal agencies establish their first websites — including, in 1994, the first website for the Prime Minister of Canada.

It felt like standing at the edge of something big.

It also felt… uncomfortable for a lot of people.

Change Is Human Work

One of the biggest points of resistance came from the team responsible for managing the Prime Minister's correspondence.

They were adamant: he should not have an email address.

We held our ground that he must.

Not because the technology was exciting, but because the possibility was.

But I learned something important in that moment.

Change is rarely resisted because people aren't capable. It's resisted because it's unfamiliar, and because we don't yet trust what it will ask of us.

So we explained. Then explained again. Then again in a different way.

We built scripts and filters. We showed how messages could be routed. We made the invisible more understandable.

And slowly, adoption followed.

The Privilege of the Work

Looking back, one of the greatest privileges of my career has been helping people through moments like that.

Not by pushing technology on them, but by helping them find their footing with it.

Because when people feel confident, when they feel supported, when they understand why something matters — together, we accomplish great things.

We're Doing It Again with AI

That same dynamic is playing out again now with AI.

The tools are more powerful. The pace is faster. But the human response is remarkably similar.

People hesitate. They question themselves. They assume they're the problem.

But they're not.

"If there is an error, it is the fault of the design, not the user." — Don Norman

We've normalized something backward.

We've normalized blaming ourselves for bad technology.

When Did We Lower the Bar?

Early in the web days, we had a simple measure for success: if a user couldn't find what they needed quickly — if they abandoned navigation and went to search — we considered that a failure.

Today, I often see a lower bar.

If someone has to go to a help file to figure out how to use a product, we've already asked too much of them.

We've normalized adapting to tools that were never designed well enough to support us.

That's not progress.

"You've got to start with the customer experience and work backwards to the technology." — Steve Jobs

Somewhere along the way, many teams flipped that.

We start with what the technology can do — and then ask people to adjust.

The Order Still Matters

It has always mattered.

**It's people first.****Then process.**Then tools — fit for purpose.

Not the other way around.

The irony is that as technology becomes more advanced, expectations should go up — not down.

We shouldn't be asking people to work harder to use better tools.

We should be expecting better tools.

A Better Standard

So when I hear someone say, "I'm just not good at this," I pause.

Because I've seen this before.

I've seen what happens when we stay with it. When we take the time to explain, to design better, to support adoption properly.

And I've seen what's possible on the other side.

We're entering a phase where technology can meet us more naturally — through conversation, through context, through intent.

That should reduce friction.

But only if we hold the line on what good looks like.

The more advanced our tools become, the more we should expect from them — not less from ourselves.

Final Thought

Maybe the question isn't whether people are keeping up.

Maybe it's whether we're building technology that's truly ready to meet them where they are.

And whether we're willing to do the harder work — the human work — to help them get there.

What would change if we stopped asking people to adapt to technology… and started expecting technology to adapt to them?

I'd genuinely love to hear what you're seeing — especially if you're navigating this in an organization where the pressure to adopt AI is real but the support isn't keeping pace.

Leah Clelland Jochim is Co-Founder & Partner at Convergence Technology Solutions & L&T Ventures, an AI and technology transformation advisory firm. She advises C-suite executives on AI strategy, operating model design, and outcome-driven product leadership. Connect with her at [email protected].