How I got over my fear of cold calling and trained myself to sell

Early in my twenties I had a complete career meltdown. At the time I was working in a job I’d come to resent with managers who didn’t support me and team members who were equally as fed up. I knew I wanted to leave but had no clue what to do next. So one day I started scrolling through the listings on seek.com and started applying for anything that looked vaguely relevant to my limited real-world experience, which at the time was operations and a bit of HR. 

A few months later I landed a job in agency recruitment; an industry that (as a total surprise to me) had a heavy focus on cold hard sales. I’d never worked in corporate before let alone in a sales environment, and on that first day dressed in black leather pumps and a tailored suit, I nervously made my way into the city. When I arrived at the wide-open plan office located on the 39th floor of a tall mirrored skyscraper, the intensity of my new workplace smacked me in the face. Despite it being just 8am, the office sounded like the floor of the New York Stock Exchange, with men and women charismatically doing deals over the phone. A giant bell sat pride of place at the front of the room right next to the top-seller leaderboard. I felt like I’d walked straight into the Wolf of Wall Street. 

It soon became clear that my new job would involve getting on the phone and cold calling businesses to generate new leads. Despite my age, I’d always been a confident person who could hold my own — one of the reasons I was hired in the first place — but I was intimidated. During those first few months I dreaded heading into the office. I’d wake up with a deep knot in my stomach, my mind racing with anticipation for the day ahead. I wondered how many people would hang up on me, or worse, yell expletives down the phone for bothering them. I was scared of being pushy, but I was also nervous about not being assertive enough and missing my long list of KPIs. 

Whenever I made a cold call, I hoped that no one would pick up

More times than I care to admit, if I heard a “hello?” I’d freak out and cut the call. I tried lots of things to stop this self-sabotaging behaviour in its tracks (I’m pretty sure none of my KPIs were tied to how many times I hung up). I tried psyching myself out before punching in a number. I tried using a script. I tried having conversations off the cuff. I tried picturing the person on the other end of the line naked (try this, sometimes it works). But the more I built up cold calling in my mind the stronger my fear became. It was a vicious, self-perpetuating cycle and one that I couldn’t break. 

When someone told me that selling is problem-solving in disguise, everything changed

I realised that just as a consultant goes into a business and identifies opportunities or shines a light on blind spots, salespeople help prospects identify and solve problems. When you’re selling, you make things easier, more efficient, quicker, cheaper and safer for the person on the other side of the value exchange. You free up their time for more important things and help put an end to their worry (or even misery). Contrary to the stereotype of the sweaty car salesman trying to flog a lemon, you’re offering something tangible of value. At that moment, my mental construct shifted and I finally saw sales for what it is. 

I adopted a curiosity-led mindset and started uncovering opportunities where I could genuinely help

Changing my mental starting point from “is this person going to be annoyed that I’m reaching out?” to “let’s discover if this person on the other end of the line needs me” changed the game. My paralysing anxiety subsided and I started actually having fun in each conversation. I pictured myself as every client’s go-to, and in the instances I genuinely couldn’t help (like that time I was asked to find a ‘Corporate Ninja’ — yes this job truly exists), I’d simply tell the client I wasn’t the right person and direct them to someone who was. 

While my recruitment days are long gone, I’m so grateful for the time I spent there. To this day I bring a curiosity-led problem-solving mindset into every business conversation I have. Instead of selling, I’m consulting. Instead of being pushy, I’m helpful. Instead of being sleazy, I’m genuinely trying my best to understand and assist.

You’re solving, not selling

If you’re dreading the long list of cold calls you need to make, are stressed about pissing someone off, interrupting their day, or making a fool of yourself… remember this: someone, somewhere needs what you have to offer. You’re the person they’ve been looking for. You have what they need. You hold the answers to their biggest questions. 

And… if the worst-case scenario happens and the other person isn’t interested in what you have to share? Picture them naked, say “thanks for your time”, and continue on with your day unfazed. 

Anna Mackenzie is the co-founder of lady-brains.