An Introvert’s Guide to Sales (& Overcoming Imposter Syndrome)

2021-09-29 | BY Anne Burke | IN Free Resources, Work Life

An Introvert’s Guide to Sales (& Overcoming Imposter Syndrome)

I didn’t think I could cold call people.

I was working as an Office Coordinator when Covid hit and, since there was no longer an office to coordinate, I was offered the chance to transition to a sales role. A generous offer, but also one that terrified me. I was sure I’d never be able to cold call anyone, to lead a natural conversation, to hold my own without outside support. I appreciated having work at such an unstable time, but I felt the transition was destined to fail. I was destined to fail, all because I’m not an outgoing, assertive, traditional salesperson.

As the months passed and my commissions rose, I still couldn’t shake the feeling that my good fortune was just that; luck. Even now, a year later and with consistently high rankings in my division, I sometimes struggle with imposter syndrome.

It took a long time for me to realize that being introverted doesn’t have to be a weakness. Given the right mindset and tools, an introverted personality can actually help you connect with people on a deeper level and, ultimately, close more deals.

A different set of tools

As established, I don’t love making cold calls. No matter how much I try, I seem incapable of making the number of calls expected of me – something that causes me endless anxiety. Yet somehow, my numbers don’t seem to significantly suffer.

Here’s why – the people I talk with don’t feel like I’m a sales person trying to squeeze them into a mismatched role…because I’m not. Instead, they (hopefully) think I’m a painfully human person who just wants to help them with their lives and careers. Apparently, this makes them more likely to share with me, connect with me, and trust me.

These four tools helped me make fewer cold calls, while connecting with more people:

1. The sniper approach

If you can nail down – as much as possible – the precise background and skills of your target, you’re more likely to find a willing audience. By spending time on the front-end learning about people, I can make each call more impactful and more likely to lead to a “sale,” while avoiding wasting my limited introverted energy on people who are unlikely to engage with me.

On the opposite end of the spectrum, extroverted people often focus less on finding the ‘perfect target,’ because they can compensate with sheer numbers. Both methods work – you just have to find which one works for you.

2. Hyper-personalization

I always try to be super personal – especially at the beginning of the call. Since I’m a recruiter, I spend time looking up a person’s resume and unearthing some unique characteristics – like whether or not they’ve ever moved cities, or if they attended a certain school. This way I can catch their eye, indicate that I’ve done my research, and show that I’m not just here to close a deal – I actually want to know about their life.

3. Anything but sales

Strangely, most of my conversations revolve around peoples’ interests, their aspirations, even their weekend plans – but not sales. I ask about their friends and kids and families. The conversation revolves around life, not work. The opportunity I’m selling is almost an after-thought. And people seem to appreciate that.

One strategy I use to inspire more ‘natural’ conversations is offering a tidbit about myself. The other day I watched the Lord of the Rings trilogy – so I mentioned that in my sales calls while discussing weekend plans. This led to either bonding with people over a mutual interest, or at least discussing why they have/have not seen the movies. I’ll also bring up big life events – my recent marriage, moving to a new apartment – to try to connect with people through universal experiences.

4. Over-prepare

In the past I would compare myself to natural extroverts; the kinds of people who could steer a conversation without any forethought – and it filled me with self-doubt. A lot of insecurities came from thinking I didn’t know enough and comparing myself to people with natural proficiencies, something I thought I lacked.

Eventually I learned that preparation can compensate for inborn skill. I could train myself to ask the right questions, to not fear awkward silences. I could do advance research and arm myself with scripts so that I wouldn’t flounder for the next topic. Doing this made it so much easier for me to trust the process and trust myself.

With these four tools, I am better able to overcome my insecurities and connect with people in a way that is uniquely mine. I may not sound or act like other sales people, but that can actually be a strength – because many people don’t want to talk to a salesperson. They just want help from a real human being, something we can all understand.

My #1 takeaway: the ‘aha’ moment doesn’t exist

Even months into finding success, I still doubted my abilities. Imposter syndrome ran so deep that I failed to acknowledge that I was actually good at this job. It felt like my luck could run out at any moment. I saw my numbers going up, but I genuinely didn’t understand how that was the case. Replicating my success seemed impossible.

There was no one time when I thought “yes, I’ve got this.” I still don’t feel that way. But one thing that helped me realize that I was no longer the struggling newbie was training new members of my team.

We recently hired a new recruit and I was part of the group helping to catch her up on the job. She was me, just twelve months earlier; no idea how to talk to candidates, how to sell a role, how to pick up the phone and have a conversation with a random stranger. I could see myself in her, except now I did know how to do these things. It helped me understand that I knew a lot more than I thought I did – which in turn made me more confident that I was doing something right.

Still, I didn’t understand the gravity of my accomplishments. So it was helpful that my team and managers regularly recognized how far I’d come – even if I tended to shrink from the spotlight. Having this culture of celebrating success was hugely impactful in easing my imposter syndrome.

If you’re also struggling to picture yourself as a salesperson, know that there’s no one definition of what a salesperson has to be. The idea of speaking with so many people, keeping track of all those conversations, connecting with them all – it was all so incredibly daunting when I started out. And it still is now! But I’ve learned that there are many ways to connect, even if you’re a quiet but friendly introvert. Anyone can be a sales person with the right tools, mindset, and drive.

I’d love to email – or call, if you’re feeling brave! – about your experience. Reach out!

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