Fear of selling and self-promotion can hold soloists back, and be the difference between sinking or swimming. 

Here’s how I got good at sales without breaking into a cold sweat.

Does the idea of trying to ‘close a sale’ fill you with dread? Would you rather stick toothpicks in your eyes than follow up with a potential client?

Six months ago, I felt the same way. Leaping into freelancing as a copywriter and communications consultant, I assumed the confidence I’d had in the corporate world would follow me into my new business.

It didn’t.

Going solo was different. I was the face of the business; I couldn’t just focus on the creative work, I had to sell. In the world of Mad Men, I had to be Roger Stirling and Don Draper.

“I couldn’t start winning jobs until I believed I could deliver them.”

If sales and pitching give you the heebie-jeebies, you’re not alone. You can overcome that anxiety and sell with confidence. Here’s how I did it.

1. I realised ‘natural’ meant nothing

No one is born a salesperson, ready to ‘sell this pen’ to the doctor in the delivery room.

You don’t need to mould yourself into the stereotype of a sleazy, smooth talker, who bullies a customer into a decision. It won’t build repeat clients, and Lady Karma is likely to come at you with swift roundhouse kick.

How to find your own version of natural selling

  • Know your audience. Understand them and why they might need your product or service. (Otherwise, it’s easy to make it about you.)
  • Be confident in what you’re offering. I couldn’t start winning jobs until I believed I could deliver them. Kick that imposter syndrome to the curb.
  • Find what works for you. For me, it’s making a connection with the client and not being afraid to show them I’m passionate about what I do. I’ve won a lot of jobs because I get genuinely excited about their project, and that’s infectious.
  • Remember each potential customer is an individual, with their own anxieties, wants and needs. I adapt my style of communication to what they need and focus on the problem they need to solved.

2. I lost the stench of desperation

If you’re starting out or in lean times, it’s tough not to let desperation take the wheel.

When I went solo, free from the corporate shackles and that cursed regular paycheck, I was surfing a wave of pure adrenaline. For about three hours. Then panic set in. I signed up for every crap freelancer bidding site, checking them in the still of the night when I couldn’t sleep. I resigned myself to a life of writing product descriptions for 3 cents an hour. I would have killed for that job.

I no longer reek of desperation. Now I just smell like coffee, yoga pants and ugg boots, like any work at home freelancer.

How to get over the desperation factor

  • Don’t feel like every potential job or sale is a test of the decision to go solo. It isn’t. That’s a short path to despair, and you’ll be too focussed on your angst to be yourself.
  • Accept you’ll be rejected. I was, and I still am. Know that before you begin, then any success is gravy.
  • Don’t pin all your hopes and dreams on each individual sale or pitch. There’ll be another chance.
  • A little self-pity wallow is OK if you miss out on a sale. But wallow for minutes, not hours.

3. I stopped fearing the phone

In my early solo days, I would verge on hyperventilating before a client call. Not even cold calls. Just calling someone back could send me into a spin. I didn’t have that problem in the corporate world, but now it was all about me. Despite our brave new tech world, the phone is still key to sales. Most people still want the comfort of talking to a real person.

How to get phone confident

  • Be prepared. Schedule some prep time before the call to check you have everything you need.
  • Make notes, even for small talk, you might need at the start. The simple act of writing them down can help you gain confidence.
  • Schedule calls just like you would a meeting – most people prefer it these days anyway – so you don’t jump every time the phone rings or get anxious waiting for a call.
  • Over-introduce. Call and remind them of your full name and what you’ve been chatting or emailing about. They might cut you off and know exactly who you are, but better that than an awkward pause as they try and place you.
  • Take the pressure off that the call must close the deal. Invest some time and energy in a real conversation.

4. I got over the ick factor

Sales have always made me feel… icky. It’s common for creative types and soloists.

I had to lose the idea that sales are about tricking someone into something. If you’re targeting the right audience, and you’ve got great services or products, you’re not tricking anyone. Be confident in what you offer, and people will make their own choices.

How to lose the ick

  • Accept you’re good at what you’re doing, that you’ve made the right decision to be a soloist, and you have something to offer. I’d started my own business, but I’d been doing the work for years and years. I knew my stuff.
  • A little self pep-talk can go a long way. Or turn to a trusted friend or community and get them to do it for you!
  • Some advice I will never forget. You can do anything. Because when it’s over, you can hide your face in a pillow for a few minutes and everything will feel better.

5. I got better at listening

Don’t fall into the trap of the stereotypical sleazy salesperson, gabbing on talking someone into something they don’t want, not letting them get a word in edgewise. That’s not being good at sales.

Make your customer feel important – they are. Without them, you don’t have a business.

How to listen and connect through conversation

  • Flip the old school sales tactic on its head. When I call a potential client or email them, my first questions are about them. I’ll ask about their business, talk about their project and help them feel more comfortable with the process.
  • Boundaries are important, but attention and empathy cost you nothing. Find out their story, what they need, and you’ll have a natural way in to discuss why you’re the right person for the job. Everybody wins.
  • My philosophy for customers and copywriting is the same: make a connection. Mention something you have in common or a mutual friend (thanks LinkedIn). It helps you both relax and talk like humans instead of business robots.

6. I remembered I was good at my job

You’ve started your business and gone solo for a reason. Remind yourself why you’re here, and what you have delivered for clients in the past. It seems silly, but looking at my portfolio of past work and at my CV reminded me I’d earnt the right to be confident. I’d earnt the right to tell people I was the best person for their job.

How to get your confidence firing

  • Trust your experience and remind yourself of it however you can. Look at your portfolio, read some glowing references. Be your own cheerleader (or I just call my mum and get her to do it).
  • A great suggestion from a writing community I’m part of was to stick a post-it note with my hourly rate to my computer. Be clear on your worth!
  • Get passionate. Your potential customer wants to know that copywriting or widgets or spreadsheets rock your world. Tell them!
  • Don’t hide your light under a bushel. If you’re the best choice, tell them why. Worst case scenario? You don’t get the job, but its good practice.

A thriving business and less sales angst

My solo business is thriving, and I’ve gotten back the confidence I had in the corporate world.

The pressure’s on when it’s your name on the door. But I’m proof you don’t need to be a pushy sales stereotype.

Find what works for you, remember you’ve earnt the right to confidence, and go get ‘em.

Do you have any little tricks that help you be better at sales?

This article originally appeared on Flying Solo, a website brimming with small business advice. Read my articles here.