The biggest hiring mistake I made early in my career was assuming years of experience meant someone was a good designer.

I recorded a short 3-minute video walking through this moment here →

Back then it made sense to me.

More years should mean more practice, more projects, more clients, more learning.

So when I interviewed people, I gave them the benefit of the doubt.

I assumed senior meant talented.

I assumed senior meant clarity in their thinking.

I assumed senior meant they could communicate decisions, deal with tough clients, handle deadlines, and talk about design beyond visuals.

But when I started asking deeper questions about philosophy, decisions, challenges, data, or impact, some senior designers couldn’t answer.

They got stuck.

They focused only on the visuals.

They couldn’t see why those questions even mattered.

And it became obvious when they applied for roles far below their level.

I couldn’t hire them because the way they thought about design just didn’t match what the work required.

One interview at DBS made this crystal clear.

A senior designer, even my senior from the same university, came in.

On paper he looked great.

But when I reviewed his portfolio and asked basic questions, he hit a wall.

He couldn’t explain his thinking.

He couldn’t see past the surface.

That moment changed the way I hire forever.

I stopped looking at years of experience.

I started looking at how designers think.

Some juniors think better than seniors.

Some communicate impact clearly.

Some are coachable and growth minded.

Those are the people I can groom.

I’ve seen that play out personally with a junior I supported from day one who grew into a senior product designer in two years.

The shift for me was simple:

Years of experience don’t matter if you can’t communicate decisions, influence the roadmap, persuade stakeholders, or show how your work changes the product.

The takeaway:

If you can’t articulate your thinking, your level gets downgraded instantly, no matter how many years you have.