The Golden Question No Other Freelancer Is Asking

During the early years of my freelancing, I didn’t ask my clients the most important question in any project. I still delivered high-quality designs, and those designs probably helped their businesses.

But that’s the problem.

I wasn’t designing with their business goals in mind. I wasn’t thinking about their conversion strategy. In fact, I wasn’t thinking about strategy at all.

And if you look back on your past work and think, “Well, it probably helped them somehow…” — that’s not a good sign.

In college, I learned how to be a digital designer. I was trained to focus on execution, not outcomes. The assumption was that I’d work at an agency where other people (account managers, strategists, marketers) would handle the business conversations. I’d just push pixels.

But freelancing is different.

As a freelancer, you are the business. You’re the designer and the strategist. And for a long time, no one told me that meant I needed to ask better questions.

That changed when I started reading materials from Brennan Dunn that shifted my mindset entirely.

Think about your clients. What do they actually want their users to do? What kind of result would create real business value for them?

Here’s the golden question I now ask on every project:

“Can you tell me more about your business goals?”

This single question unlocks everything. It reveals what the client is really after. It naturally leads to deeper conversations about their target audience, their pain points, and the outcomes they care about most.

It also educates the client. Most haven’t thought about how design can support their business—they just think they need a new website. Asking this question invites them to think bigger and align their goals with your expertise.

✨ Freelance Insight

When you ask strategic questions, clients see you as more than a designer — they see you as a partner.

And here’s the kicker: it helps you close the deal at a higher rate.

Take this example:

Back in 2014, I helped CompassCare launch a new website. They work with women facing unplanned pregnancies. Their conversion strategy starts with education by showing women they’re trustworthy and compassionate. The business goal? To encourage those women to book an appointment.

So instead of writing a proposal full of technical jargon or a breakdown of my hourly rate, I wrote a proposal focused on how I could help them get more leads and increase appointments through the website. That’s what they really needed. And that’s why they hired me.

I didn’t explain the ins and outs of “user experience design.” I didn’t justify my pricing by estimating hours. I pitched a result — and they said yes.

Today, the freelance market is more crowded than ever. It’s noisy. Clients have too many choices. But most freelancers are still just showing portfolios and listing services.

If you want to stand out, ask better questions. This one simple question tells the client that you care about their success and that you know what you’re doing.

Those are the two most important things any client is looking for. Make sure they see both in you.