Things I Used to Believe: Executives Generally Have the Same Experiences as Line Level Team Members

Several years ago, I worked at a company with several thousand employees.
Over a few weeks, I started hearing repeated complaints about company laptops — slow performance, frequent servicing, difficulty running the systems people needed to do their jobs.

This surprised me.

As an executive, my laptop was rotated out roughly every 18 months. It always worked flawlessly. I assumed everyone else had a similar experience.

When I asked IT about the complaints, the answer was simple:

“Replacing laptops for junior employees is too expensive, so we keep older equipment running as long as possible.”

The people on my team were doing the heavy lifting — building proposals, running calculations, producing client-facing work — and their laptops weren’t keeping up. Meanwhile, most executives, myself included, primarily used our machines for email.

Here’s the real learning for me:
Because my experience was so different from theirs, I assumed we shared the same experience. I didn’t. That assumption made it harder to understand and address the real issues facing my team.

So I made a choice: I wanted to always have the oldest laptop on my team, and anyone with equipment older than mine should be upgraded.

Not surprisingly, some peers didn’t like it. They liked getting new equipment.

Looking back, this story isn’t about laptops. It’s about leadership and awareness:

• When leaders allow their experience to be different from their teams — and lose awareness of it — it’s extremely hard to respond to the real needs of the people who rely on them.

• Productivity is an investment, not a perk. The cost of friction is invisible if you don’t experience it.

• Leadership privilege can quietly distort priorities, even when intentions are good.

Curious how others think about this:
How do you make sure your experience as a leader aligns closely enough with your team’s to really advocate for them?