The Creative’s Guide to Selling Without Feeling Weird
Lessons from real conversations, client wins, and learning to guide (not just pitch).
Sales as a Creative: What I’ve Learned About Leading with Value
Hey everyone,
Hope the week’s treating you well. Especially for my fellow designers and creatives—whether you’re freelancing, running a studio, or just figuring it all out, I’ve got some thoughts to share today on something we all wrestle with: sales.
I had a convo with a team member recently after we wrapped a successful call with a new client. They said something a lot of creatives feel deep down:
“I don’t think I’m good at sales. Maybe I’m overthinking it.”
I’ve been there too. I wasn’t the loudest person in the room. I wasn’t naturally the one starting conversations. But over time, I’ve figured out a few fundamentals—not to sell better, but to connect better. Because when you do that, sales becomes a byproduct.
Let’s talk about what helped me shift my mindset and close better deals.
1. Start With the Real Value You Provide
The first major mindset shift for me was this:
I stopped selling “web design” and started positioning us as a marketing company that just so happens to build great websites.
That small shift changed how we approach projects—from strategy, to research, to delivery. Our process now starts with uncovering business problems. Whether that’s design, SEO, or communication. The website? That’s the vehicle, not the solution.
So ask yourself:
What’s the bigger problem you solve?
And are you communicating that in your proposals or on your calls?
2. Get Context Before the Conversation
One of the best things I did to improve sales convos? I stopped walking in blind.
We added an intake form that gets us the info we need before the call even starts. Not just name, email, and message. I’m talking:
Budget
Why do you want to work with us?
Where did you hear about us?
What are you looking for? (dropdown with service options)
What’s the goal of the project?
When someone fills that out, we already have a sense of who they are, what they need, and whether we’re a good fit. That allows us to lead the conversation and steer toward results, not just deliverables.
3. Just Be Helpful—No Pressure
This is simple but powerful: just be helpful.
Don’t assume the client knows how things work. Don’t expect them to speak your language. Educate them, empower them, and guide them when needed.
One of the best things a client ever told me was:
“We don’t mind being challenged—we want to be led.”
That shifted how I showed up. It reminded me that people want a guide. They want you to ask the questions, push back when necessary, and help them avoid mistakes they can’t see yet.
4. You Can’t Force It
Not every deal is going to close—and that’s okay.
There was a time we did everything right: great call, solid proposal, strong follow-up. And still… nothing. Not because we messed up, but because they just weren’t ready to invest or we didn’t have a good first impression.
That used to bother me. Now? I chalk it up to timing. You can’t trick someone into saying yes, and honestly, you shouldn’t want to. What’s meant for you will align with you. And if it doesn’t, there’s always something better ahead.
Final Thoughts
If you’re trying to get better at sales, start by getting better at listening, leading, and clarifying the value of what you do. That’s where the real wins happen.
Your voice, your process, your perspective—they’re all valuable. Package them with intention, and you’ll start attracting the kind of clients who see it too.
Talk soon,
–Dexter