I had $2,000 burning a hole in my pocket, and no one seemed to want it.

Back in the spring of 1999, I set out to buy a decent triathlon bike. I was committed to training for Olympic distance events, and I knew I needed a good bike to be competitive.

I went to the three best bike shops in Madison, Wisconsin, with a mental list of questions. Simple questions that if answered, would earn my business.

The first shop had such a low-key, no-pressure sales environment that I couldn’t even get someone to come over and talk to me.

It was like shopping at a big box retailer, with a bunch of low-paid employees but no one eager to make a sale.

The second store wasn’t much better.

“Can I help you with anything?”

“I’m looking for a triathlon bike,” I said.

“Well, feel free to look around and let us know if you have any questions,” said unambitious sales guy #2.

The guy at bike shop #3 at least answered my questions. When I started showing obvious buying signs, though, he backed off.

“Is the upgrade to carbon forks a good idea?” I asked.

“It’s really your call,” he said.

“How quickly could you get this fitted for me?”

“It’s pretty quick, no problem,” he said. (Umm…the reason I asked is because I want you to size me and get it set up. I want to buy a bike today!)

I was seriously frustrated. I couldn’t give these guys my money!

On the verge of giving up, I made a pit stop at Mission Bay Bike Shop in Elgin, Illinois, on my way to O’Hare.

As soon as I entered, Bill, the owner, asked where I was from. When I told him “Madison,” he said, “So you’ve been to Yellow Jersey, Willie Bikes, and Budget Bicycles, and now you’ve come to buy a bike?”

He said it in a fun way, yet I also knew he meant business.

Instead of waiting for me to take the lead, he quickly started asking me all the right questions.

He understood my situation and led me through the process. An hour later, I gave him my credit card for a bike, shoes, a pump, and a wet suit. Total outlay: $2,115.

I was happy, and I never once had to say, “Okay, let’s do this.” He made it easy for me to buy.

Why am I telling you this story? What does this have to do with you and me?

Our website is our storefront, of course. And if we’re selling a service, the only way to land new clients is to engage in a conversation.

Unfortunately, we often make it too hard for prospects to buy.

Like Bill, the owner at Mission Bay Bike Shop, we need to:

1. Ask the right questions

We can start by asking the right questions on our website, and we certainly need to when we talk to somebody live.

Do you have a list of questions you ask every time? Do you know your audience well enough to know exactly what to ask?

2. Take the lead

Don’t sit back and wait for their questions. Every conversation should be a well-choreographed presentation.

Do you have a step-by-step process you take every prospect through?

3. Make it easy for them to buy

Landing a new client should be a seamless, natural progression of our engagement with them. Act confident enough and lead them where you want them to go. Don’t ever make them say,”Yes, let’s do this.”

Are you giving people an easy opportunity to do business with you? Are you creating what I call a “buying atmosphere” versus a selling one?

These three simple points seem lost on most retail establishments, a lot of website owners, and from what I’ve observed, many copywriters.

All it takes is doing things slightly different than most of your competitors to succeed.

I call it the New Way of Selling for Independent Creatives, and it will be a big part of the new Café Writer membership site coming here soon.

I’d love your input. What is one question or challenge you have about selling? Let me know here.

Steve Roller

Author Steve Roller

I'm a business coach, author, copywriter, world traveler (33 countries on five continents so far), and professional speaker. In addition to helping companies get more customers and make more money, I help other writers create profitable businesses. I offer one-on-one coaching, professional copy critiques, and live, in-person business-building workshops. When I'm not writing, coaching, or speaking, I enjoy nothing more than hanging out with my wife and four kids and planning my next adventure.

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Join the discussion 6 Comments

  • Shelly says:

    Well Steve, you know when you go into a store and you’re just browsing, to see if the retailer has what you’re looking for? And maybe you’re not really sure sometimes what exactly what you’re looking for. And as soon as a salesperson appraoches, you’re like a deer in the headlights. You don’t really want their help right away…you just want to look. A salesperson hovering, asking you questions perhaps seems pushy. How do we avoid this perception on our websites too? Thank.

    • Steve Roller says:

      Great question, Shelly! Part of it is by asking lots of questions on your website. So even when you’re making a point, you’re doing it by asking them things, not telling them. (Remember, “telling is not selling.”)

      Part of it is bringing things up, potential objections, before they do. E.g., “You might be thinking it costs a lot to hire a top-notch copywriter, right? Well, you might be pleasantly surprised…”

      Or how about, “The fact is, you might not even need my help. One of my goals with this site is to give you some do-it-yourself answers, so feel free to check things out…”

      Do some things that most copywriters don’t do on their websites. Stand out. Be you. Be likable. Have a little bit of fun (most copywriters are way too serious). When I can find someone who makes me laugh even a little from their website, they’re hired.

      Those are just a few things. I’ll think about it and get back to you with more soon.

  • Cheryl Ewing says:

    Hi, Steve. How does one get over “writer’s block” when facing the prospect who just walked into his store? In other words, how does an inexperienced copywriter learn to confidently and easily take the lead in a conversation when a prospect phones in response to your website or other marketing piece?

    • Steve Roller says:


      Thanks for your comment. One word: practice. We practice writing good sales letters by hand. We practice our copywriting skills in classes and programs. We practice writing and re-writing our Home and About pages.

      So why in the world don’t we write out and practice some phone scripts? Because no one wants to talk about it. Is it taught in any of the popular copywriting courses? Not that I’ve seen, maybe because if they told people that it included sales conversations on the phone, they wouldn’t sell as many programs. I don’t know.

      I’m working to change this, and you’ll a lot of helpful material on the Copywriter Cafe membership site which will be unveiled in February. Stay tuned, and let me know if there’s anything specific I can help you with in the meantime.

  • William says:

    Hi Steve,

    Great post!

    You are so right. I have experienced similar situations in my neck of the woods. There are plenty of times in fact where I have gone to a store looking to buy but found no one to take my money.

    It just baffles me how companies can even be in operation when their sales clerks aren’t doing anything to make a sale.

    Selling needs to be a priority in any business.

    • Steve Roller says:

      Most definitely, William. I’m doing my part to let copywriters become better at selling, and my clients as well. I have a top-secret service I offer that no one else seems to be.

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