Why the Most Uncomfortable Swag Question Might Be Costing You Better Employee Merch
There’s one question that quietly makes its way into almost every company swag initiative—and yet, no one really enjoys asking it.
“Hey, what size are you?”
It looks simple on the surface. But in reality, it often feels awkward to send and just as awkward to receive. Messages get rewritten, delayed, or ignored altogether. What should be a smooth step in the process suddenly becomes a small but noticeable hurdle.
That uncomfortable moment is more than just a minor inconvenience. It’s a signal that the traditional way of handling company merch might be due for an upgrade.
The Everyday Awkwardness We All Pretend Is Fine
Every team planning branded merch eventually runs into the same situation.
Excitement builds around a new initiative—onboarding kits, holiday gifts, milestone rewards, or company events. Everything is lined up and ready to go.
Then comes the pause.
You need sizes.
What follows is a familiar pattern:
- Messages that feel a little too personal
- Spreadsheets that fill up slowly, if at all
- Gentle reminders that turn into multiple follow-ups
- And a few guesses that never quite work out
The momentum dips, and something that should feel exciting starts to feel like extra work.
Why This Small Problem Feels Bigger Than It Is
The discomfort isn’t just about logistics—it’s about people.
Clothing size is personal. Some employees hesitate to share it. Others aren’t sure what to say. Some ignore the request entirely and hope it resolves itself.
Even when responses come in, they’re not always reliable:
- Sizes vary from brand to brand
- Fit preferences differ from person to person
- And sizes can change over time
So even after collecting all that information, there’s still a good chance something won’t fit quite right.
The result is a mix of delays, extra coordination, and a less-than-perfect experience for employees.
Turning an Awkward Moment into a Smarter Strategy
This is where things shift from problem to opportunity.
Instead of trying to improve the process of asking for sizes, the smarter move is to remove the need for the question entirely.
That idea alone creates a strong and highly relatable message:
Asking for employee sizes is awkward. So skip it.
It works because it’s honest, recognizable, and immediately relevant. Anyone who has managed swag before understands the challenge right away.
And from a marketing perspective, it naturally leads to a better solution.
A Better Way That Feels Effortless
The alternative is simple—let employees choose for themselves.
With an on demand company store, employees can:
- Browse a selection of branded merch
- Choose the items they actually want
- Select their own size privately
- Have everything delivered directly to them
There’s no need to collect sizes, follow up, or make assumptions.
The entire process becomes smoother, faster, and far more comfortable for everyone involved.
Why This Approach Makes a Bigger Impact
Removing one awkward step creates a ripple effect of benefits.
Better Fit, Better Use
Employees receive items that fit properly, which means they’re more likely to wear and enjoy them.
Higher Engagement
Instead of being asked for information, employees get to interact with a curated store. It feels like a perk, not a task.
Less Administrative Work
No more tracking responses or organizing data. The process runs on its own.
Reduced Waste
Fewer incorrect sizes mean fewer unused items.
What starts as a simple improvement quickly turns into a more efficient and enjoyable system.
Building a Campaign Around the Idea
This concept also opens the door for creative and engaging campaigns.
Awkward workplace moments are easy to recognize and easy to relate to, which makes them perfect for storytelling.
A few examples:
The Overthinking Reply
An employee staring at a message, unsure whether to choose medium or large, and second-guessing every option.
The Unanswered Thread
A sizing request sent to a group chat with no responses in sight.
The Almost Right Fit
An employee receiving a shirt that technically fits, but not in a way they’d ever wear confidently.
Each scenario highlights the same issue while keeping the tone light and approachable.
More Than Convenience—It’s a Better Experience
This shift isn’t just about avoiding awkward conversations. It’s about improving how employees experience company merch.
When employees choose their own items:
- They feel more considered
- They receive something they actually like
- They associate the experience with ease and flexibility
These small improvements contribute to stronger engagement and a more positive perception of your brand.
The Takeaway
That simple question about size may seem minor, but it introduces friction that many teams overlook.
Removing it changes everything.
By giving employees control over their selections, companies create a smoother process, eliminate unnecessary discomfort, and deliver a better overall experience.
And as an ad idea, it works just as well.
Because the most effective messaging often starts with a simple truth everyone recognizes—and offers a solution they didn’t realize they needed until now.
