Why Working “Sales” Jobs Made Me Bad At Selling Myself

Before and during college I worked my fair share of menial jobs. I’ve worked in fast food restaurants and as a server in a steakhouse; I’ve done retail and telemarketing. I even worked summers growing up at my grandmother’s dog kennel, cleaning up dog poop—certainly nothing elegant there.

But all of these jobs had one thing in common: at each, I was interacting with the company’s customers, trying to guarantee they left satisfied and often trying to get them to buy a little more than they’d intended.

Many people would think that’d be a great way to learn about the sales process and to gain a general understanding of how to make a sale happen.

In fact, I’ve heard more times than I can count how other freelancers used the skills they learned in retail jobs or restaurant jobs to help themselves be successful in their own businesses. And, perhaps predictably, most often those “skills” boil down to knowing how to make a sale.

While I’m glad to hear that’s how it worked for them—I’ve got to say that it didn’t work out so great for me. In fact, I’d say those jobs did me a huge disservice.

What I Learned Then

Sure, while working at Taco Bell (my first job ever), I learned all about add-on sales and how to suggestively sell a customer something they may have forgotten they needed—the classic “do you want fries with that?” (although at Taco Bell we offered a drink or a dessert instead).

Then I graduated to working at a women’s clothing store as a sales associate. I learned two important lessons there—the importance of consistent customer service and how to ask for a sale.

And while waiting tables at an Outback Steakhouse I learned the value of the simple things: a big smile and a friendly word. Further, I learned that different people like different levels of services and began to figure out how to tell how to figure out how much attention various customers warranted (as well as how to juggle several needy customers at once).

Even working at the kennel I knew to ask customers if they wanted us to bathe and groom their dog before they came back to pick them up.

What I Missed

Even though these things were all valuable, I still think all they are completely overshadowed by the one thing I learned to overlook in each of these positions—prospecting.

In each of those jobs the customers were provided for me. They come into the store or restaurant of their own accord. I wasn’t out there approaching strangers, trying to convince them to choose us over the competition.

They came in and then I sold them something.

I see that reflected in my sales funnel today—once a client and I are talking, I’m relatively good at landing the sale (especially if we talk on the phone). But when it comes to calling or emailing new clients, when it comes to actively pitching myself in the search for new work? Forget about it.

I freeze. I procrastinate. I employ every possible excuse I can think of and then some to avoid pitching myself, even though when I do I achieve fairly positive results.

I know it’s a numbers game—the more you pitch the more you make. But this is definitely still something I’m working to overcome. I’ve had to set aside a dedicated chunk of time each day or week to focus on sales—contacting new leads, following up on warm ones and reaching out to existing clients to see if there’s additional work there—or it just never happens.

But I can’t help but think if I hadn’t been conditioned to wait for the customer to come to me, I wouldn’t be so terrible at this. After all, everything else I’ve had to learn I’ve approached systematically—read all I can, create a game plan, tackle and conquer it.

I guess the real lesson here is that the same methods don’t work for everyone. Even though other freelancers may have found their sales skills working for others, for me, I’m finding those skills only by working for myself.

Is there someone everyone else says you should try that just won’t work for you? Or do you have a favorite sales tip for me? Share it in the comments!

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Melissa Breau spent the last three years as an editor at a magazine but in 2011 decided to launch full speed ahead into the freelance life. She currently offers copywriting for small businesses and professional editing for authors, as well as blog posts on each of the above, over at melissabreau.com.

2 Comments

  1. Yep prospecting comes with its own world of issues as you found out. I’ve done tons of phone sales and you’re right its a completely different dynamic when the customer is presented to you. However once you have to go and proposition that customer you find out just how much guts you really have :)
    Marianne recently posted..certified nursing assistant jobs

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  2. I agree- it’s HARD to be proactive when it comes to finding new clients. I’ve found a bit of research really helps me. If I’m going to a networking event, and can find the names of some of the attending companies, I take a quick look at their websites. If I have an opportunity to speak with them, and give them a simple tip or two on updating their copy on their website, it sometimes turns in to a job. If not, I gave them an actionable tip to take away and make their website or blog better.

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