Remote Work Didn't Create a Training Problem. It Exposed One.

Every few weeks, I hear another version of the same conversation.

Companies can't find entry-level employees who can "hit the ground running." Recent graduates can't find entry-level jobs because every posting seems to require experience. Somewhere in the discussion, someone inevitably blames remote work.

On the surface, it makes sense.

A recent Wall Street Journal podcast explored exactly this question. The hosts described managers who miss the spontaneous conversations that happen in the office, young employees who want more opportunities to observe experienced colleagues, and companies struggling to train people who are working remotely.

As I listened, I kept waiting for someone to ask the question I was asking.

Not, "How do we get people back into the office?" Instead: "How does expertise actually get transferred from one person to another?"

What if remote work didn't create a training problem? What if it simply exposed one?

For decades, organizations relied on thousands of tiny learning moments they never had to design. A new employee overheard a difficult client call. They asked a quick question over the cubicle wall. They watched someone handle an unexpected problem. One moment by itself wasn't transformative. Together, they became apprenticeship.

Not the formal apprenticeship of a trade, but the ordinary, everyday process of learning by watching, trying, asking, and gradually taking on more responsibility. Much of that learning happened naturally because people shared the same physical space.

Then remote work arrived.

When those informal moments disappeared, many organizations concluded that the office itself had been the solution.

I'm not convinced.

The office wasn't the teacher.

The people inside it were.

Spending most of my career in education has made it hard for me not to see the world through the lens of learning.

In education, we don't expect students to become independent because they watched a teacher solve one problem. We model. We practice together. Only then do students work independently. Teachers know this as "I do. We do. You do."

Most of the learning happens in the middle.

It's where misconceptions surface. It's where judgment develops. It's where learners begin explaining their own thinking instead of simply copying someone else's.

I wonder how many workplaces accidentally skip that step.

A new employee shadows someone for a day. They're handed documentation. They're told to ask questions if they get stuck. Then they're expected to do the job.

That's observation followed by independence. It isn't guided practice.

One of my favorite instructional strategies is something called a think-aloud. Instead of silently completing a task, an experienced person narrates what they're noticing. It's a simple way to make thinking visible.

"I'm checking this first because..."

"I considered doing it this way, but here's why I didn't."

"This email looks routine, but this sentence tells me it's actually urgent."

It sounds almost too simple to matter, but those tiny comments make invisible expertise visible. They reveal the judgment behind the work—the part that's almost impossible to document or add to standard operating procedures.

They're also the first thing to disappear unless we intentionally make room for that kind of thinking out loud.

The more I think about it, the less interested I become in debating whether everyone should return to the office.

That's the wrong question.

The more interesting question is this:

How do organizations intentionally transfer expertise?

Because if remote work exposed a weakness in how we develop new employees, returning everyone to the office won't solve it by itself.

But if the real problem is learning design, that's good news. Those learning experiences can be designed. We don't have to rely on accidental apprenticeship anymore, whether people work five days a week in the office, fully remote, or somewhere in between.