How to Turn Prospecting Into a Game You Can Win

I loved to play games when I was a kid … in fact, I still do!

For me, the best games have some structure and are not completely won by pure luck or chance. I love games like Scrabble, Monopoly, and chess — games where you can affect your own outcome if you’re creative or risky enough.

I’ve always shared my love of games with my son, and I tried to get him interested in chess at a young age. I was persuasive and clever. I showed him how great it was.

He wanted nothing to do with it.

That all changed, however, when his second-grade teacher formed a chess club at school.

Suddenly, it was all he wanted to do. He studied strategies, challenged me to games constantly, became fascinated with custom chess sets … Chess became COOL!

All it took was the right introduction, at the right time, with the right person.

It’s the same for us freelancers when it comes to prospecting!

I’m not going to pretend that prospecting will ever be as fun as sitting down and playing a game — at least not for me. I’m a writer, not a sales rep (been there, done that, moved on)! But it’s a necessary task if you want to get new clients and succeed as a freelancer.

You can affect your own outcome if you’re creative or risky enough. And if you approach prospecting like a game, maybe the process will become less intimidating.

So let’s look at four common prospecting challenges and how you can overcome them …

The Right Introduction

Have you ever experienced the frustration of not even being able to get your foot in the door with a prospect? When you know you’re a match made in heaven, but you can’t get anyone to take your calls or respond to your emails?

Instead of continuing to do the same things hoping for different results (the definition of insanity, by the way), try looking for a mutual friend or acquaintance who can connect you.

Social media is a natural choice for this, but email introductions work great, too!

For example, I met a fellow copywriter at the 2012 Web Copy Intensive who happens to know the owner of a winery in North Carolina (this was a wonderful introduction opportunity for me because I specialize in wineries and the wine industry). So she wrote an email introducing me to this man, and she cc’d me.

I was then able to follow up by replying to the original email — automatically reminding him that I was referred to him by someone who he trusts, and elevating me a couple of notches simply by my acquaintance with her.

He liked my proposal and asked that I get back to him after harvest and crush (the busy times of year for a winery).

Which brings me to my second common prospecting challenge …

The Right Time

Second grade happened to be the right time for my son to fall in love with chess. Had I known this when he was in kindergarten, maybe I could have saved the effort of trying to get him to like it then … and in first grade …

But MAYBE my earlier efforts had “primed the pump,” so to speak. Maybe my prior attempts made it easier for him to say “Yes” when the time was right.

It’s the same with prospecting … if a prospect likes what you’re offering, but the time just isn’t right, then keep following up until it is! Don’t look at it as wasted time or useless effort — consider that your previous efforts and good follow up might just make it easier for your prospect to say, “Yes!” and become your client when the time is right.

The Right Person

Of course, pitching your services to the right person is crucial to success!

You can’t play chess with checkers pieces, and you can’t convert a prospect into a client if he (or she) isn’t the decision-maker.

This seems like such a basic thing, but I’ve certainly made this mistake before … haven’t you?

I once sent a proposal for a comprehensive web-marketing campaign (website content, social media, blog, e-letter, autoresponders … the works!) to a company’s sales manager. He had contacted me, and we had discussed his product at length.

My proposal totally matched his vision for achieving success for the company … he was enthusiastic and ready to move forward, BUT then he said those dreaded words …

“I’ll show it to the owner, and see what she says.”

Really?!? It’s a good thing we were having a phone conversation so he couldn’t see me slap my forehead!

Once I calmed down, I consoled myself with knowing that at least I have an ally who will be in my corner as I follow up!

The Right Price

Sometimes everything can be right — the right introduction at the right time to the right person — but in the end, it all comes down to price. And if it’s just not in the budget, well …

There are two options when your prospect tells you it’s not in the budget: revise the project to a lower price point or move on.

My son became an expert negotiator that year of second grade. If I didn’t have the time (the budget) for a complete game of chess, he would suggest, “Let’s just start a game now, and then we can finish it later.”

Great idea!

If your prospect doesn’t have the budget for you to completely rewrite his website, for example, you could offer to just start with the About page … and then finish the rest of the project later when funds become available.

This approach gives your prospect a custom sample of your work and keeps the door open for the project to expand at that later date. HOWEVER, I suggest that you only do this if you REALLY want this particular client.

Otherwise, choose option 2 — move on!


So there you have it — my strategy to win the prospecting game, get new clients, and succeed as a freelance copywriter.

I encourage you to give it a try! At the end of the day, you might even be able to say, “Check!” … as you deposit one in the bank.

I’d love to hear how you’ve overcome challenges and won your own prospecting games! Please leave me a comment and share some strategies!

And by the way, if you’re looking for prospects who are hiring right now (The right time? … Check!), sift through the job opportunities posted on the Wealthy Web Writer and AWAI sites as well as at

Game on!


Michele Peterson

Michele Peterson is a direct response web copywriter, online marketing strategist, speaker, and coach. She draws on 20+ years of sales and marketing experience to help her clients tell their stories, engage their audience, and make more money. On a personal note, she’s the wife of a winemaker, baseball mom, back pain survivor, SF Giants fan, former cheerleader, gardener, master networker, tech geek, avid reader, and fan of all things Disney.

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