How I respond when people say “Shouldn’t it just work that way?”

What are you actually trying to achieve here?

It’s the magical phrase to disarm, align, and course correct a wayward customer.

As a business owner, someone eventually will come at you with comments like “Shouldn’t it just work that way?

Or

“Why doesn’t it just do this?”

When I was earlier in my career, those two phrases felt so rude. But now, I have the experience (and deep breathing skills) to see them differently.

Here’s my product: mostly for DIY creators (my people!) who are trying to monetize content, launch courses, build communities.

At the core, they have the same three simple needs:

[x] Register users
[x] Set up recurring subscriptions
[x] Unlock content

But meeting someone’s three simple needs isn’t enough. The devil is in the details of “shouldn’t it just work that way?”

What way? Their way.

What they’re really doing is projecting a single past experience with an online or even offline business onto mine.

One time they subscribed somewhere and that’s how it worked.

One time they created a user account and something else happened.

Their perception of what software “should do” vs. the reality of what it does do is the gap we’re managing.

So what should a product owner do, besides want to flip a table?

First, do NOT jump to building every “obvious” request.

Instead, pause and ask the user: “What are you actually trying to achieve here?”

That conversation usually reveals a middle ground. A way to help them reach their goal without undoing your product or business.

Polite. Firm. Curious. Creative.