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This $1500 Sales Training Helped Me Win More Business (Learn it Free in 10 Mins)

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Here’s the story of how I paid $1500 to learn how to be good at sales calls, despite being an awkward English nerd. And here’s what I learned, for free, in 10 minutes.

I remember hearing the phrase, “Stephen King didn’t sell more books because he’s a better writer, he’s a better salesman,” and feeling discouraged. My dad is a history professor. My mom worked in the medical field.

And all the “sales” bros I knew? (They were always bros, it seemed.)

I didn’t want to be anything like them.

They seemed overly focused on shiny cars (leased, of course), tacky/expensive clothes, and could only ever have conversations about money.

People in “sales” just felt gross to be around.

This felt depressing. Did I really have to choose between starving with integrity, or thriving as a sellout?

Look, you’re on an article titled “the 10 minute, $1500 lesson to sell your creative work.” Obviously there’s going to be a twist to this story where I learn how to balance sales with creative work.

And there is! After struggling as a freelancer for years, I finally learned how to easily “sell” my work in a way that felt:

  • Authentic to my true self (no fake “sales talk”)
  • Ethical and honest (no manipulation or sleaze)
  • Effective and fun (no exhausting self-hatred afterward)

It cost me $1500 to be taught this method. But I could have learned it for way less. And today, I’m sharing it with you at no cost whatsoever.

(One more note – this method works for both winning freelance clients and full-time gigs!)

Why am I sharing this for free? Because I want as many ethical, honest creative folks (like you) to learn how to win the gig. Because if YOU are doing the work, we cna be sure it’s going to be done in a way that champions inclusivity, empathy, and integrity.

(Can’t say the same for sales bros.)

You can watch the 10 minute video just above to learn the process, or you can read below.

Why I Paid $1500 for Sales Coaching

Have you ever been in a situation where you know you’re being sold, but you buy in anyway?

Maybe you’re shopping for a car, or maybe a gym.

That feeling where you know you’re being manipulated into making a decision you don’t really want, but you feel helpless to stop, is what I call “bro sales”.

It’s how so many big name coaching and event packages sell out.

Back in 2014, I found myself on the receiving end of one of these bro sales calls. I’d responded to a Facebook ad for a webinar teaching you how to start a social media marketing agency that earned $6000/month.

(And supposedly, this agency would run “on autopilot.”)

After the webinar, I somehow ended up on the phone to discuss a mentoring program. And I could feel I was being sold to. Yet I still bought in!

So when the person on the phone asked, “What are your goals in your business?”, I told him, “I want to learn how to be better at sales.”

“Listen,” I said, “you’re clearly good at sales calls. I know I’m being sold right now, and I’m still going along with it. I want to learn how to sell with the same confidence and power so I can work with clients who are a perfect fit.”

And that’s what he taught me.

Over 6 weeks, I was taught the sales process that closed me and hundreds of other students at $1500/pop.

Once I learned the steps, I realized that I didn’t need to spend 6 weeks learning it. I could have learned it all in a single session.

It gets even better. A couple of years later, while reading the “free” (plus $9 shipping and handling) book DotCom Secrets, I saw the exact same sales call process that had been used on me.

Turns out this guy wasn’t amazing at sales. He’d just practiced a simple formula that was commonplace in this industry.

I’ve seen this formula pop up in many, many other places as well. There’s nothing proprietary about it. And since information wants to be free, I want to share this info with you… free.

My steps for painless, casual sales calls (that win more business!)

In order to understand how to succeed at sales, you have to make a mindset shift.

Many people think of sales as “manipulating others out of their money”. And it’s true – many sales bros do this. That’s unethical and not something I’m interested in.

But ethical sales – the kind I do – is based on “showing how you can solve a problem.”

This requires:

  • Empathy to truly connect and understand your prospective client
  • Patience to truly serve and focus on what your prospect needs
  • Confidence to know that if this isn’t the right fit, you can walk away and find something better

When done well, it helps you close more work at higher rates for clients who are ethically aligned with you.

But it only works if you’re focused on how you can solve the “real” problem.

If you’re coming from a place of service, then the next steps will come easily.

Step 1: Set Expectations to Ease Tension

Why do clients hire you? To lead them in solving a problem!

When they hire a freelancer or full-time employee, they need to justify to their boss why they picked the right person. So they feel just as nervous about hiring the right person as YOU feel about getting the gig.

If you help the prospective client feel at ease, they’ll remember that feeling and be more open to hiring you.

You do this in a sales call by telling them what to expect. Share your process up front so there aren’t any surprises. Not only will you reduce the collective nervousness around this call, you’ll show that you’re a professional who can be trusted.

Here’s a script I often use to set expectations:

“So what we’re going to do today is discuss your project, your goals, and how I can possibly help. We’ll also talk about other details so I can better understand if I’m the right fit to make this a success. And assuming everything goes well, we’ll talk about next steps. If I’m NOT the right fit, I’ll be able to know which other creative I can connect you with.”

The actual wording is less important than making sure I achieve the following:

  • Showing that I’m interested in solving THEIR problem, not mine (being focused on them)
  • Preparing them for the kinds of questions I’m going to ask (reduces mental task switching)
  • Letting them know that I’m open to this not being a perfect fit (removing tension by providing an out)
  • Future pacing next steps (so they’re thinking about how I fit into their overall project)

Once I’ve done this, I move onto the next step.

Step 2: Ask Questions About the Project

By understanding what your prospective client is trying to achieve, you can discuss how you might be a possible solution. You can also know if you’re not the solution they need.

Remember: you’re on this call because they are actively considering hiring you. It’s okay to show why you are the solution if you can deliver (or believe you can). It’s not manipulative or  gross if you can actually do the work they need done.

When asking questions, it’s important to be curious and understand what’s really important to your client. Your goal is to understand how this project affects their business or organization, including the monetary value to them of your work. (This will ideally be much more than they’re paying you.)

Some of the questions I ask about the project include:

  • How do you measure if your blog/site/thing is successful?
  • How well is your current site/blog/etc. performing?
  • What’s the average value of one of your customers?
  • How many new customers are you currently bringing in per month through this channel?
  • Are there target benchmarks for knowing if this project will be successful?
  • If we were to be successful with this project, how much more company revenue would this help bring in?
  • So if we were to increase current performance by, say, 10%, that would be worth (Average Customer Value times # New Customers/Month times 0.1), is that right?

Note on that last question: your objective is to establish a measurable performance benchmark.  This does several things.

  1. It establishes a credible budget range for this project (your client should be able to pay for your work with only a few additional clients)
  2. It shows you’re interested in making data-driven decisions, even in creative work, which feels less risky than solely gut-based decisions
  3. It shows you’re focused on OUTCOMES, not deliverables (newbies focus on deliverables, professionals focus on outcomes/transformation)
  4. It helps you understand how well this client fits with your own criteria for good clients

In my experience, clients who are hoping your work will “save” their business are often a headache. One piece of copy or graphic design or deliverable simply can’t overcome other parts of a business that aren’t working. Don’t put yourself in a position where the client can blame you for their own mismanagement (which happens all the time).

But if the client’s goals ARE a good fit, then it’s on to budget.

Step 3: Establish the Budget

This part of the conversation can often feel awkward for both you and clients. The client ALWAYS has a budget range they’re comfortable with, even if they don’t know that about themselves.

I’m serious. Sometimes clients will start a conversation thinking they’re find with any budget. But when the creative actually says a number, suddenly subconscious preferences show up.

“Oh, I just kind of wanted any number… but that one’s a bit higher than I thought…”

This is where you get to show real leadership and professionalism. You get to uncover your client’s real budget in a way that helps them feel comfortable.

I like to take the “All force, no grace” approach here and just embrace the awkwardness.

“Well, that brings us to everyone’s favorite part of these calls: budget!”

Or maybe something a little less forward:

“Okay, that brings us to budget.”

It’s important to be CALM and CONFIDENT – practice on your own until it feels natural. (Yes, the most effective sales professionals spend time every day practicing “scripts” like this. And if you’re a freelancer, you’re also a professional in the business of selling your own work.)

Pro Tip: when asking for a budget, provide anchors to reduce decision paralysis.

If you ask for a budget range and get, “Well you tell me” in return, you can ask it again with anchors:

“Is your budget closer to $500, $5000, $50,000…?”

The wildly high number at the top will give your prospect an easy out. OBVIOUSLY your client isn’t going to pay $50,000 for a one-page website design, for example (although I’ve seen this during my agency days). So they can laugh and go, “Oh, no, it’s actually more like [real budget].”

The goal here is to help your client feel confident and in control. And they are! It’s their journey, you’re just the guide along the way.

If their budget is a good fit for you, then awesome! It’s time to close.

And if their budget isn’t the right fit, you can gracefully say, “Unfortunately, that’s a bit beneath my normal fee for work like this. But I’ve got a few people in my network who might be a better fit. Can I pass your name along to them?”

Step 4: Close the Deal

At this point, if everything is a good fit, your job is now to keep the momentum going and close the deal.

Your priorities are to get a signature and get paid. So your closing script should reflect that.

Many newbies accidentally kill all momentum by asking the wrong question. Instead of keeping the conversation going in a positive direction, they grind everything to a halt by asking,

“So, do you want to work together?”

NO. NO. NO.

Don’t do this. It makes clients reconsider everything they’ve experienced so far. It introduces so much doubt into what’s been a positive experience. And it completely ruins your sales conversation.

Instead, use something like this:

“Based on our conversation today, it sounds like we’d be a great fit to solve your problem. Assuming you feel the same way, my next steps are typically to send over a statement of work and invoice for a deposit, which would be [50%/100%] for a project of this scope. Any other questions before I send that over?”

If that feels a little too forward, you can add some cushion by asking, “Does that sound good?”

The goal is to ask a question where the answer is “yes”. And again, I can’t stress this enough: only close deals that are actually a good fit for your business AND the client’s.

It doesn’t help you nor the client if you close work that sucks.

That’s the key difference between manipulative “bro” sales and what I’m sharing with you today. Bro sales is selfish and all about how much money the sales person is making.

But what I’ve shared with you is about serving the client and solving their problems.

Take Your Training to the Next Level

As I’ve mentioned, every creative freelancer is a sales professional. It’s part of your job to sell your creative work to prospective clients.

The truth is, sales is easy and kind of dumb when you figure it out. But it’s clearly very important because businesses spend billions of dollars every year on sales training.

Well, I just saved you $1500. Follow the tips in the video. Write down the outline and put it near your computer. Practice going through the scripts on your own until it feels second nature (this makes a huge difference).

And pretty soon, you’ll realize that sales is neither hard nor sleazy.

If you’d like to do an even deeper dive on mastering sales calls, I’ve got a resources that could be a great fit. , Check out my buddy Joel Klettke’s training, “Mastering Sales Calls From a Guy Who F&#!ing Hates the Phone.” It’s a brilliant training that goes into even more detail about the psychology behind ethical sales calls for creative freelancers – people like copywriters, designers, etc. I’ve seen it, and it’s worth 100x what he charges for it. (Seriously – even if you pay $200 or whatever he’s charging nowadays, it’ll help you earn at least $200k over the course of your career.)

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