The Business of Likability

It was back when I was just a few years into freelancing copywriting and was starting to raise my prices. Instead of working for everybody and their uncle and writing everything from ad copy to website landing pages, my pipeline for work got slimmer. I was having fewer sales conversations. Then in the midst of all that, I lost a client.

If you’ve ever worked for yourself, you’ll understand this flavor of confidence crisis:

Your world shatters in three dimensions when you convince yourself that you’re not only the most mediocre employee, and the most clueless entrepreneur on the planet…but also that you have become the worst amalgamation of all the terrible bosses you’ve ever had. 

My moxie and I started hurtling, spiraling down deeper and deeper into the bottom of the mineshaft without a shred of light, and I began questioning why any of my clients were working with me. 

To be honest, it wasn’t my first time. And because we all learn our own ways of hauling ourselves back into the light, I knew what to do.

My resurrection of choice is learning the heck out of whatever topic I’m having intense anxiety about. In this case, I had decided that I needed to get a handle on my sales calls.

No one had ever taught me to sell, I strongly disliked most salespeople I had met, and I was super wimpy when I talked about money. 

To start, I purchased an online course from a Canadian copywriting magnate (yes, there are a few, and they are queens to be respected) and started to follow her sales call template. In the instructional videos, she strongly advised not deviating from her structure and that for maximum efficiency, the call should only take 15 mins, from start to finish. I now realize that, given the +10 points to be discussed, had I stuck to the ticking timer, I would have been cutting my prospects off mid-sentence to move on to the next question. 

It sounded good in theory, but once I started testing the template on my leads, it felt uncomfortable. I wound up asking stuff that didn’t connect to the natural flow of the conversation. To boot, I missed opportunities to use my intuition and interview skills to get the answers I needed to suss out if we were a good fit.

Still, I gave a few more honest tries on new prospects before I realized that this approach was turning people away.

It should be noted that at this point, I was still saddled with my original anxiety that I didn’t know how to run, perform or manage a business. I had new frustration because I had failed to implement ‘sales call best practices properly’. And now I was confused because before the crisis of confidence, I had been attracting clients through my network. What had I screwed up?

So, along came Samantha. 

She was the sleek, fierce nineties businesswoman long before oversized blazers became cool again.

By the time she became my client, had run her own six-figure marketing business for several years, had two kids, wrote a book on balancing career and family (and did a full book tour), and was working as the CMO of a professional services organization in a fancy office building downtown Toronto. 

She wore her strawberry blond hair close-cropped and I still can’t figure out if it has a color code. She looked like she worked out daily and made very deliberate decisions from very balanced blood sugar levels. She owned a gorgeous seaside cottage in my home province for chilling out…but also ate chauvinistic CEOs for lunch.

I’ve never been intent on climbing any corporate ladders. Rather, I have always maintained a delicate and admittedly unusual balance between mermaid and capitalist. So finding suitable mentors has always been a challenge.

When I started working with Samantha, I realized I had met one of those rare types who have figured out how to have it all and with panache—clearly, a woman to be respected, trusted, and feared (just a bit).

We had been working well together for a few years when I shared with her that I was mid-crisis of confidence with my business and didn’t know what to do.

She announced that she was transitioning from CMO to career coach and asked if I would like a free coaching session. I was pleased as punch and we got on the phone.

First, I shared all (but ALL) my professional anxieties. Once the floodgates were open, she heard it all “I don’t have a professional brand! It feels like maintaining a mask that isn’t me. I’m running my sales calls from behind this mask and it isn’t working because it feels like I’m not allowed to be myself. I’m trying to squeeze all these canned questions into a really short call because otherwise I’m apparently not building a scalable process for my own sales pipeline. I don’t know how to sell” And yadda yadda yadda.

Then, she shared some advice that has transformed how I run my sales calls, how I do my marketing and tbh—my entire identity as a solopreneur.

She said: “You know what you’re doing. That’s why I’m working with you. But beyond that, you are likable and trustworthy.

The point of these sales calls is that your prospects need to start LIKING and TRUSTING you and wanting to work with you.

So forget this 15-mins time limit—you need to spend however much time in this initial call to build trust and show that you are the expert.

JUST LET THEM LIKE YOU.

You know you are good at asking questions. You know are good at quickly getting a grasp on their business model–just play to your strengths and BE YOURSELF. ”

Well, this hit me like a freight train. Here I was, thinking that my sales calls were missing the grey-tufted tactics of an IBM-era VP of sales that I could never be…when actually, I just needed to believe in myself. 

Never the answer you want to hear, right? But little by little, I began to observe that one of the little-known reasons we choose to work with external partners is because they are likable and we feel we can trust them. This is true for all B2B purchases—whether we are buying a SaaS product or choosing to work with a new professional services team.

I began to see that if I played to my own strengths within a sales call–this would help potential prospects figure out if they wanted to work with me.

This business of being likable and building trust throughout the marketing and sales process has been a lesson that I’ve carried with me as I’ve transformed my business. Now, I work on larger research contracts, have more intense sales conversations, and discuss big sums of money. 

The fact that I am a competent interviewer and a great analyst are paramount to the success of my contracts.

But more than that, I’ve come to believe that you can’t put a number on the value that likability and trust confers on the success or failure of a new deal. So I’m learning to allow more of myself into my sales and marketing, and so far, it has helped bring more of the right prospects and clients into my life.

The Questions You Should Ask…

• Have you made it a priority in your sales cycles to build trust and likability on discovery calls with new leads?

• How can you authentically work more of these qualities into your marketing?