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4 Mistakes Freelancers Make When Selling Themselves


You’ve probably heard that you should always be selling. It doesn’t matter if you’re sporting a suit and tie at a conference pre-party or chatting business with a fellow parent at a kid’s birthday party: if the person you’re talking with could end up either hiring you or referring you to others, you better sell yourself to them.

And this is good advice. You should be “selling” yourself. Human relationships are forged on people selling themselves to others. (I had to sell myself to my college’s admissions office. I had to sell myself to every boss, client, and customer I ever worked with. I had to sell myself as a potential boyfriend, and later husband, to my wife).

But I think this advice can often lead people to think that selling is a win-or-lose game. That your job is to create a positive impression as quickly as possible, make your pitch before whoever you’re talking to becomes disinterested, and go in for the kill — I mean, the sale.

I’m generally introverted, and have never been too comfortable using the same advice insurance and car salespeople use. Besides not being a huge fan of pushy sales tactics, I also tend to think my “product” — the business-changing stuff I do for my clients — is worth the price, and that no one’s being short changed and needs to be convinced using whatever it takes.

So today I want to extract a bit from my upcoming course, Double Your Freelancing Clients. It’s a handful of mistakes that new, and even experienced, freelancers make when talking with people about their businesses.

1. Not asking the right questions

Let’s say you’re talking with someone at a backyard BBQ. They bring up that they have a construction business. What happens next?

Well, you might be inclined to jump into trying to talk about your business and the sort of stuff you do. After all, there’s blood in the water now — you feed off people like them!

But hold up. Let’s let them talk. Let’s hear their story.

You: “So tell me about your business.”

Business Owner: “I’m in construction – I’m building that new Hilton down by the beach. My team and I handle organizing all the subcontractors – builders, architects, and so on…”

You: “Nice! How do you find organizing all that? It must be crazy. I do a lot of work with software, and it seems like you’d need some crazy huge project management tool to manage all of that – especially since you’re building a highrise!”

BO: “Yeah, it can get complicated. But Microsoft Excel keeps it all chuggin’ along.”

You: “So you’re coordinating building a tower with Excel? That must be quite the spreadsheet!”

BO: “Well, the office manager and my assistant do a great job managing the chaos.”

You: “Just out of curiosity… How much time do the two of them spend each week working in this spreadsheet?”

BO: “Lately, pretty much full time. It’s a lot of work.”

You: “Are there other things they could be doing?”

BO, with a blank stare: “Of course, but this is their job now.”

You: “I understand. I sometimes feel like I’m in the business of putting people like your office manager and assistant out of work.”

Another blank stare from the BO: “…What do you do?”

You: “I help businesses solve things that can be simplified with custom software. So let’s say I worked with a company like yours, I’d figure out what routine tasks were booking your team full time – and find ways to either eliminate those chores or make it take a lot less time. I know one problem with things like Excel are that it’s really hard to get multiple people working out of it at once. So when a company outgrows something like Excel or pen and paper, they come to me.”

Notice that the focus is all on them, and their business. You only come in with what it is you do when you discover a point of intersection — a place where the needs of their business overlaps with your business and what you provide.

Grab my Socratic Questioning Worksheet [free], which is from Double Your Freelancing Rate. It’s a great primer for helping you ask the right questions.

2. Not giving anything away for free

Many of us are reluctant to give away anything for free. We don’t want to be too eager to prescribe solutions…. because, for all we know, that prospective client we’re talking to might take your prescription and find someone else to do the work!

The other day, I was sitting down with a project lead, and we were talking a bit about his project.

I didn’t try to persuade him too much on hiring me, instead I tried to persuade him on the right course of action he should take. I told him exactly what I’d do if I was running his business, and what resources he should check out.

A lot of us fear giving away our “secret sauce,” especially when we’re still trying to court the client’s business. But it’s important to realize that the kind of clients we want to work with aren’t the type who will take our prescription and either try to do it themselves or price shop it around. Good clients know that 1) their time is too valuable to try to figure out how to do whatever it is you do and 2) it’s risky as hell to find good, solid talent.

I sell myself through teaching. I want clients to realize that I don’t just know what the buzz words are, but that I know how to use them and are capable of thoroughly diving into a problem and solving it. By diagnosing a problem on the spot and providing a solution, you’re showing a prospective client that you’re confident in your ability to turn problems into solutions.

And early on, this sends a strong signal. You’re in the business of architecting solutions. You don’t just respond to requests; you’re instrumental in fulfilling the requirements.

3. Not including a “call to action” in their conversations

The mistake a lot of people make when selling is to end a conversation without a call-to-action. If you’re chatting with somebody at a bar, and the conversation turns toward them and their business, and you drop hints that you run a business that could probably help them, don’t end by saying “I’ll give you a call.”

You’re not giving them anything. For all they know, you’re blowing them off. We’ve all probably been on the receiving end of an “I’ll call you” — knowing full well that we’ll never actually get a call — after meeting a cute prospective partner. Business isn’t really all that different.

Make sure that each interaction you have with a prospective client has a clear next step.

If you’re talking with me about business and I think I can help you, I’m going to leave you with an option to talk with me about working together in an environment that isn’t a bar.

“Jim,” I would say, pulling out my iPhone and opening my calendar app, “I have next Tuesday and Thursday available at 10am. Which day would be better for me to come by and talk to you more about whether we could work together?”

Jim’s only available response is either “Yes, Tuesday at 10 will work” or “No, I’m booked both of those days,” (which can lead into another volley of dates and times). Had I just said “we should talk”, neither of us are committing to anything. There’s no implicit expectation that something should actually happen next.

4. Thinking that people are more interested than they really are

People need to know enough to be able to make an informed decision — and nothing more.

It’s easy to get caught up in the minutiae of why test-driven development with rspec is better than the alternatives or why WordPress is the most feature and plug-in rich blogging platform available. But all too often, we let our passions overflow from their rightful place — user groups, tech conferences, industry blogs, and so on — and spill over into our interactions with clients.

A few months back, I sat in on a conversation with a very talented designer who was trying to convince a business owner that they needed to make their website responsive. The business owner was being taught the ins-and-outs of media queries and pixel density and on and on. The eyes on this poor business owner were visibly glazed — she had no idea what he was talking about, and I couldn’t figure out why she should care!

It’s like when I go in to get my car fixed. Admittedly, I know very little about cars outside of I like it when they work and are capable of bringing me from Point A to Point B. But I’ve talked to mechanics who try to tell me way too much about the inner workings of my engine. If I’m in a repair shop and my car needs some non-urgent service, I want to be told why I should consider the service being proposed to me. If I don’t get it, is it possible my car won’t start tomorrow morning? Next week? Next month?

Likewise, pixel density and media queries don’t tell Sally the Business Owner anything about why she needs a responsive site. They’re the features, but clients buy for benefits. Will a responsive site help her get more customers? Will it be easier for people on small screens to see what Sally offers, where she’s located, and when her business is open?

What are some mistakes that you’ve seen freelancers make (or maybe you’ve made yourself)? Let me know in the comments below!

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