Pushing Boundaries in Product Design: When Bold Wins Big

There’s a moment in every product manager’s career when you have to decide—play it safe or take the leap. For me, one of the biggest design wins I’ve ever been part of almost never saw the light of day.

The Backup Plan That Became the Game Changer

We had a design that was bold—too bold, we thought. We lacked confidence in it. So much so that when we went to present to the C-suite, we prepared a safe, polished alternative. The “normal” option. The one that wouldn’t ruffle feathers.

We showed the safe design first. And the CEO? Not impressed.

I felt it. The energy wasn’t there. So, in a split-second decision, we pulled out the bold design—the one we had almost buried.

The reaction? Instant shift. The CEO loved it. Not only did he approve it, but he was so inspired that he pushed other teams to align their assets with this new look. The site went on to win awards. And to think—we almost didn’t show it.

As I turned to the designer who had first pitched the bold idea, they simply mouthed, "I knew it."

That moment changed how I approach product design forever.

Why Playing It Safe Can Kill Great Design

The Trap of ‘Just Getting It Done’

Many design teams operate under an unspoken rule: Don’t upset the balance. The goal is to get the job done, create something functional, and avoid making stakeholders uncomfortable. The reality? Playing it safe is the fastest way to make something forgettable.

The best designers aren’t just good executors; they are risk-takers. And the best PMs? They create the space for designers to take those risks. Because if you don’t actively encourage boldness, what you get is a string of “good enough” designs—none of which will ever transform a product, let alone a company.

I’ve worked with safe CEOs before. And I’ve regretted it. Safe leaders don’t push. They don’t challenge. And they certainly don’t encourage risk-taking. That’s not me. I want to make things better—much better. Playing it too safe never allows for the kind of big, upward changes that truly set products apart.

How I Push My Design Teams to Go Bigger

As a PM, I can't push design on my own—I'm not a true designer, I can design but it's not a Product Designer is always going to be quicker. However what I can do is challenge designers to push past their comfort zones and bring great ideas back to something deliverable.

I tell my teams this:

"If you don’t go bold, no one else is going to. You need to scare me with your design. If I think it’s safe, then you haven’t pushed hard enough."

About 75% of the time, I do have to push them further. That’s not a knock on them—it’s just human nature.

Here’s how I do it:

1. Give Stakeholders Time to Sit With a Big Idea

I never ask leadership to decide on a bold design in the moment. Instead, I say:

"Sleep on it. Show your kids. Show your husband. Hell, even show the dog—not that he'll help, but just explaining it out loud might make you think about it differently."

This helps people process and detach from their initial gut reaction, which is often fear of change.

2. Steal From The Best (Even If That Means Yourself)

When a team is divided between two designs, I ask:

"What don’t you like about each?"

"What can we take from one to make the other better?"

Essentially, we steal from both to create one that is truly great. No compromises—just a remix of the best ideas.

3. Sometimes, Forget Scope

If you always optimize for scope, you’ll never take the big swings. Yes, there’s a time and place for MVPs and iteration, but sometimes you need to go big and take a risk.

Not every CEO or product leader agrees with this philosophy. That’s fine. But in my experience, the difference between a really successful launch and a “we did something” launch comes down to the willingness to push beyond safe constraints.

4. Make Experimentation The Norm

If an idea is too bold, that’s exactly why we should test it. I’m constantly shocked at how wrong my instincts can be. The experiments I think will win don’t always land, and the ideas I think will flop sometimes take off.

If there’s uncertainty, that’s a reason to try, not a reason to kill an idea.

What Success Looks Like

1. When Bold Becomes the New Standard

The bold design we almost didn’t show? It didn’t just change the site—it changed how we approached design moving forward.

The team stopped thinking small.

I stopped playing it safe.

We shifted from avoiding risk to embracing it.

2. When It Spreads Across the Company

Success isn’t just when a design goes live. It’s when the design influences other parts of the business—when marketing, sales, and leadership start adopting the same boldness.

Take another project I worked on: a company sitting on thousands of user-generated images they had the rights to use. We categorized them, integrated them into the site, and suddenly—

We weren’t just selling more.

Marketing was using them everywhere.

Sales wanted them.

Post-sales teams found value in them.

Even outside companies wanted to license them. (No chance!)

That’s what success looks like—when a single design choice transforms a company’s identity.

3. When You Win the Awards You Almost Didn’t Enter

I won’t lie—seeing that site design win awards was incredibly validating. But what stuck with me most was the realization that we almost buried it.

That’s what haunts me the most—not the risks that didn’t pay off, but the ones that never even got a chance.

Final Thought: The Ideas You’re Scared to Show Might Be the Best Ones

If there’s one lesson I’ve learned, it’s this:

What scares you might be exactly what your company needs.

That’s why I push my teams. That’s why I refuse to settle for “safe” designs. And that’s why, the next time you’re debating whether to present a bold idea or play it safe, you already know the right answer.

What’s a bold design decision you’ve made (or almost buried)? Let’s talk in the comments.