18 Questions to selling naturally as a freelancer

Questions are powerful.

Most of us introverts find a special kind of stimulation within questions.

We ponder. We think. We figure stuff out.

What can I say? It’s just in our introverted inquisitive nature ?

It’s because of questions that people adore and look up to great philosophers.

The world has a different kind of respect for those who dare to ask and answer the tough questions.

Think about a life-changing decision you’ve made–I’d bet money you made that decision after asking and answering a real tough, maybe even intimidating question.

I often tell those dear to me:

Don’t be scared to ask the tough questions. It’s what separates the extraordinary from the ordinary. Click To Tweet

Those who dig deep are typically the ones we remember most. They make a real impact when taking action.

Have I convinced you about how powerful questions can be?

If you’re not convinced, then maybe I haven’t asked a tough enough question yet.

I’ll ask a more relevant question.

What do questions have to do with freelancing, introversion, and selling?

Here’s my assertion:

There are 18 questions that can guide you into mastering selling as an introverted freelancer.

That’s why these 18 questions also happen to be the outline for Bona Fide Selling–an online workshop for introverted freelancers who want to sell better without sacrificing their introversion.

Is your curiosity going through the roof yet? I’d expect nothing less from a fellow introvert.

But before I list out the 18 questions, let’s briefly talk about selling.

There are plenty of books, articles, and resources that can teach you how to sell.

And it’s easy to get caught up with all the how-to’s, tactics, and tricks. The problem is that most of that content is written by/for an extrovert or someone totally unrelatable.

That’s why you feel 80% (okay, maybe more like 110%) uncomfortable when you hear the word “selling”. You might even consider it a dirty word–and I don’t blame you!

But selling isn’t dirty. And it shouldn’t make you cringe. Click To Tweet

Selling is necessary. Selling is the backbone of your business. You signed up to sell the moment you decided to freelance.

The reality is that selling as an introvert looks very different. It looks nothing like what you read or see on the internet!

Another reality is that the sales process for freelancers is different from traditional businesses (more on this later).

If you’re an introverted freelancer, guess what?

You’re a one-person show who needs to learn how to sell. No one will do it for you.

No sales = No project = No money = No fun.

You should also learn to sell in the least draining way. The last thing you want is to sacrifice quality of project work because you’re soooo drained by selling.

Once upon a time, I barely had any energy to do project work because I spent all my energy selling.

The worst thing about it? I sold nothing worth the drain! ?

The key is to sell in your most natural way and to develop a sales process that fits you and your business.

(Reread that last sentence if it didn’t stick. It’s really that simple.)

The 4-Step Sales Process For Freelancers

Every sales process is different. There is no one size fits all. However, for certain types of businesses such as freelancing and consulting businesses, there are natural sales phases.

For us freelancers, consultants, and creatives, we all have 4 natural phases in our sales process:

  1. Position – Attracting ideal clients
  2. Prospect – Connecting with ideal clients
  3. Convert – Turning ideal clients into real clients
  4. Improve – Repeating the process more efficiently

Here’s a free course outlining the sales process from an introvert’s perspective.

The real challenge is executing the 4 steps in an effective way that feels completely natural to you and your clients.

This is where the 18 questions come into play.

The 18 Questions To Selling Better

Okay, here’s the moment you’ve been waiting for… The 18 questions.

I’ll list the questions in order and categorized according to the step they belong to.


  1. Am I confident in my decisions?
  2. Do I have a clear understanding of my introversion?
  3. What’s the best mindset for selling?
  4. Do I really have a solid niche?
  5. Who is my ideal client?


  1. Do I have enough leads?
  2. How can I effectively ask for referrals?
  3. How do I make the most of conversations with new acquaintances?
  4. What are effective ways to build rapport and value?
  5. Do I waste my time with fake prospects?
  6. Is there a right way to scheduling a sales meeting?


  1. How can I be more confident in sales meetings?
  2. How can I frame better questions that help me sell?
  3. What is the best way to present my pricing?
  4. How do I get contracts signed as soon as possible?


  1. Am I missing out on repeat business and referrals?
  2. Is my sales process improving with every sale?
  3. Are there useful tools that can help my sales process?

If you can find the answers to these 18 questions and take action accordingly, I promise you’re bound to sell better.

You’ll discover how to sell in your most natural and authentic way, which means you’ll be way more confident, which means you’ll sell more and higher quality projects, which means you’ll make more money, which means you’ll have more time, which means…

You get the point, right?

Knowing the 18 questions alone should be enough to point you in the right the direction. They’ll prompt you to start thinking about the right things when you sell.

Alright, one last thing about these 18 questions…


Go and research as many of them as you can. Start finding answers and take some real action.

And by all means, if you want to save time and some effort, sign up for Bona Fide Selling.

I’ve done lots of the hard work for you.

The online workshop has been structured to walk you through a natural process of discovery.

Of course, you’ll have thinking to do, decisions to make, and actions to take. Bona Fide Selling guides you through the process. Another awesome thing is that you’ll get real feedback to make sure you’re as effective as you can be.

After taking the online workshop, this is what you’ll have:

  • A strategy to sell your projects for 35% more in price
  • A real understanding of your natural selling style
  • A sales process tailored to fit you and your business
  • Lifetime access to the workshop’s content

What else could an introverted freelancer who wants to improve their selling ask for?

Anyways, I’ll leave you with a challenge.

Try asking a question about selling in your freelance business that’s not covered by one of the 18 questions.

Let me know if you come up with anything in the comments below or send me an email.

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