Freelance 101: The Fine Art of Cold Calling

by Leanne Rollins, Membership Manager

Warning: The following article deals with possible rejection, fear, and sheer guts. Reader discretion is advised.

Mastering the fine art of cold calling

The weather suited a Wednesday perfectly—dreary, cold, gunmetal grey skyline. I sat alone in my home office facing the telephone—oddly, the precise colour of the sky outside. I sat and contemplated the previously unthinkable—pick up the phone; call a complete stranger; try to sell my services…my writing services, that is. You see, just a few weeks earlier, I decided to throw myself into the challenging world of freelance writing. For better or worse, I put together a business plan; set up a Web presence; and purchased the necessary startup equipment. The only thing missing was, well, work.

There are many different ways to find clients: networking, responding to posted ads, begging, pleading, etc. My favourite method is networking—I've landed ALL of my contracts to date through networking. But when I was getting started the results of networking were slow to show themselves. At the time, I was working with a career transition counselor who sagely informed me that "80% of job placements result from direct contact by the job seeker." She went on to tell me that most jobs were created off the cuff—the company didn't even know they needed a service until it literally smacked them in the face.

In other words, she wanted me to start COLD CALLING!

What makes cold calling so scary?

Put simply, it's simple fear of rejection. Now, I'm not easily intimidated (those who know me might wonder if I've EVER been intimidated). And yet, the idea of picking up the phone and calling a total stranger made my palms sweaty and my heart rate speed up. Having suffered rejection from my job loss just a month before, did I really have the guts to pitch my services to a complete stranger? After a little reflection, I realized I wasn't afraid to make the pitch—I just didn't really know WHAT to pitch or WHO to pitch it to. 

So if 80% of jobs aren't even posted, how do you figure out who to target?

I needed a plan. I sat down and mapped out my objective, which turned out to be ridiculously easy. I had to find companies who needed documentation. With all the high- tech companies in Waterloo, this wasn't a big challenge. 

Here are a few things I did (and continue to do):

• I spent a lot of time browsing the Communitech Web site. This provided a pretty comprehensive list of high tech companies doing Research and Development (R&D) in the area. By searching each company's Web site, I could tell whether or not they even created documentation. I could also tell how many employees they had. Typically, if a company has less than 50 employees, they don't employ in-house writers, and likely haven't outsourced yet either.
• I browsed the newspapers for companies that had recently received grants or funding. With money in their pocket to develop new projects, opportunities for hiring writers (especially short-term) were possible.
• I kept a close eye on Gary Will's Tech Digest, and I watched the market to see whose stock was doing well, and whose was tanking. Sounds crazy, but opportunities for freelancers often exist in companies who just did a layoff. (Although you take a risk that they might not be able to pay you!).

From my search, I compiled a list of companies that had no documentation posted on their site, had poor quality docs posted, or had fewer than 50 employees. Rather than contacting the HR group for each company on my list, I used their Web site and easily got the name of the Chief Technical Officer (CTO) or Head of R&D. If a position doesn't exist, you can bet HR won't be able to help you. Instead, go as high up the food chain as you can. The CTO is a good bet.

But, what do you say?

So I had a contact list. Here's the best tip I can give you—hit up your network and find out if anyone knows somebody at ANY of the companies on your target list. When you call, the best thing you can start off with is a reference from a person they know. It creates an instant connection, and the person on the other end of the phone will be much more willing to hear you out.

Now, I needed to start placing the calls. To do that, I had to figure out what to say. That's where my company research came in handy. I realized I had to target my pitch specifically to each company's needs. A generic call wasn't going to cut it. I prioritized my company list, and then typed up a value proposition statement for the first few on my list. "Hello, my name is Leanne, and I am a freelance technical writer. Person x, who works at your company, recommended I contact you about the possibility of…" You get the idea. 

The people I called were really nice and accepting of what I had to say. I had to chase one guy down for about a week, but my persistence paid off with an interview. In the end, I placed only two cold calls, and I landed meetings for both!

How do you close the deal?

I had actual scheduled meetings! I dressed up and looked my professional best. I met the CTOs in question and was my usual enthusiastic self. However, I learned a harsh lesson at this point. I managed to sell my services so well to one CTO that he definitely wanted to hire me. FULL-TIME. He saw the value in what I proposed, and realized that he had the amount of work and the budget to support a full-time role. Someone out there should thank me because the company has since filled the role (I turned it down because I wanted to give freelancing a real go).

What lessons did I learn?

I learned a few lessons from my first cold-calling attempts.

First, people are really nice, and the worst they will do is say "no, thank you". 

Second, pitch only portions of your value-add and after you get one contract out of the deal, pitch other areas in which you can provide your services. For example, don't pitch both docs and training all at once, or even end-user and service docs all at once—instead, target your pitch on a specific area that won't require you to be onsite 24x7x52 or you will talk yourself into a full-time job. 

Third, there a lot of interesting and exciting opportunities out there just waiting to be revealed. You never know where you'll find them, or when they'll find you!

This is my summer cliff hanger. You'll have to wait until September to find out how to develop your own personal network, and how to lose the weight after you enjoy many networking lunches.

About Leanne Rollins

Leanne recently became a self-employed contractor, escaping management roles for the first time in years. This newfound freedom has allowed Leanne to take on extra-curricular activities such as a more active role in the STC. When not writing or playing with her kids, Leanne enjoys running and soccer.