5 Questions Nobody’s Asked You (That Can Change Your Business)

If you’ve talked with other website designers or branding professionals, you’ve probably gotten a fairly standard list of questions from them — asking what color schemes you like, if you have a Pinterest board, what’s your “style”?

But if you’ve read anything on this website, you know that’s not how I look at your project, and it’s certainly not where I start with it.

At least not at first.

When we meet, I’m going to ask you The Big Questions, the kinds of questions that run deeper than looks and deliver more than pretty.

Want to know what I ask that surprises most people?

Well here you go:

My 7 most surprising questions that you definitely want to answer.

1. What is your main moneymaker? And…

2. what do you *want* your main moneymaker to be?

Often the thing that brings you the most income isn’t the thing you want to be doing. Many of my clients come to me when they’re in transition, which often sounds like “I sell a lot of X, but I’d really like to move into selling Y. But X is my main moneymaker!”

In these cases, we want to keep your moneymaker making money while you grow your new “thing”, whether that’s a new product, a new service, a new course… whatever.

But we can also emphasize the thing you’re transitioning towards throughout the design, so you get a website (and a business) you can grow into and sets you up to achieve your future goals.

3. How many units of your products or services do you sell monthly/annually? Are there seasonal fluctuations?

This question is mostly to make sure you’re in a stage of your business where you will see real ROI from working with me.

It’s an ethics thing.

I don’t want to take your money if I can’t make you money. If you don’t have a tested, tried and true product or service yet, I’m not a good fit for you (yet!).

4. What is the goal of your website, or…

5. do I have the goal of your website right?)

Usually, this is where I reflect back the goal I think my client has for their website based on how they’ve described their audience, their primary moneymaker, their services, and where they’re transitioning into.

Like, “What I’m hearing is that we need to continue to have people contacting you for individual services, but also create a waitlist for this new course you’re launching, so when you’re ready to sell it, you already have a list of interested people to pitch to.”

See how strategy gets in there right away? Cool, right?

6. Tell me how you onboard your clients.

This question is really about systems and processes. What tools do you use (if any)? Are you running your whole business from your inbox? (That’s okay, but there are better ways). Maybe you sign up for every new shiny CRM and project-management system, and you’re overloaded.

I’ll ask you to tell me what you want, what you need to do, and then figure out how we can support you with systems you’re comfortable using. I don’t set my clients up with project management systems, but I can recommend some excellent ones depending on your needs.

7. What are some problems you have in your business (not just your website)?

This is THE MOST HELPFUL QUESTION I ASK! Because this is where it all comes out – what’s not working in your business. And the amazing thing is – your website can solve so many more problems than you’d think. Problems like…

  • You keep attracting the wrong clients and they’re driving you crazy. (Could be a copy problem.)
  • Your last launch didn’t go as planned. (Could be you’re missing some opportunities for list building and marketing.)
  • You have a big list, but they’re just lurkers and never engage? (Could be copy, or design, or your freebie…)
  • You want to figure out this “passive income” thing, but not sure how to sell products on your service-based site? (We can do so much with this.)
  • You feel like you should be making more money than you are, but aren’t sure how? (My process tends to unearth opportunities and find money that’s fallen through the cracks.)

These questions help lay the groundwork to ensure that everything we do together is easier — that’s where the “ease” comes from in “Design with strategic ease”!

If you’re not sure you can answer these questions right now, that’s okay. You don’t have to have all the answers. We’ll find them together (I’m here for ya). 

If you’d like me to ask you questions that may just blow your mind, book a call, and let’s talk about how we can make your business better.

Natalie McGuire

Hi, I'm Natalie McGuire!

I'm a website designer + digital strategist who believes in design with strategic ease. Meaning, gorgeous design is informed by customer insights that make your business a whole lot easier. If you want to stop losing customers by having "just another pretty website," work with me.

Stop losing customers by having
“just another pretty website.”

Natalie McGuire Designs: Design with strategic ease


Natalie McGuire Designs stands against inequality, injustice, hate, discrimination, and systemic racism, and is deeply committed to investing in diversity and inclusion, and standing up for what is just, inclusive, loving & equitable.