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The Street-Tested Secrets to Selling Anything to Anyone

July 17th, 2014 | 1 comment



london street


Remember that job you had in your teens or early twenties that kinda made no sense at the time, but proved good experience later in life?


 I had one of those.


When I was 22 I had a job that was not on my career trajectory (a trajectory that would catapult me from English major to being Carrie Bradshaw to then being Oprah Winfrey).  Instead I landed a job that taught me more about the art of selling than any job since.


So instead of taking a sensible job that was somewhat connected to my oh-so-ambitious career trajectory, I went for a random “fun” job instead and became a charity street fundraiser. “Chuggers” they called us (those sensible people with real jobs + real suits). I was a wide-eyed antipodean who had just arrived in London after spending all of her travel money in Asia, so if the Gap Year was to continue money needed to be made. But, truth be told — I took this particular job because the male “chuggers” were like, totally hot. Did I mention I was 22 and single?


Even though the job was taken for the wrong reasons, turns out I could not have had a better education in the art of selling. I quickly rose to leadership within the company because I consistently smashed sales targets. I mastered the art of small talk in a way that yielded big results. For a natural introvert, the personal growth was exciting, yet excruciating.


Now I’m not going to give all my secrets away (not for free…+ in the one post, anyway!). But I’m happy to share the fundamental secrets to selling anything to anyone, which I discovered + honed across virtually every demographic in Great Britain.


Secret # 1: Know Exactly Who You’re Talking To.


While most of my fellow street fundraisers were delivering their pre-prepared spiels I was mastering the art of small talk that gained big insights, quickly.


Until you know something meaningful about the person you’re selling to, there’s no point in outlining the features or benefits of your product or service.


On many occasions, my fellow street fundraisers would beg me to share the exact words I “was saying to these people.” They wanted to know my superior spiel so they could replicate it.  But most of the time I didn’t know what I was saying, because I changed my spiel, which means I changed the conversation to suit the particular individual I spoke to.


Now, (not to blow my own horn) let it be said that charity is not an easy sell… especially when you’re appealing to sympathy. I, like most of the general public, get what’s called “charity fatigue”… where people get tired of caring.  So I quit appealing to sympathy. Instead I quickly figured out someone’s “selfish” desires and aligned the features + benefits of that particular charitable organization to help fulfil those personal desires. And yes, the desire to feel like you’ve made an actual, measurable difference is very real. The desire to see ourselves a certain way is powerful.


Short answer: The question “What’s in it for them?” has to be front and centre when you’re selling anything to anybody.



Secret # 2: What You Believe Will Happen, Usually Does.


This part freaked me out the most. On those streets, I wasn’t just relying on 22 yr old looks, my natural charm and my mouthful of persuasive language techniques. There was something deeper and more powerful at play.


You don’t have to believe me, but I know I reached a point of sales mastery where I was literally drawing people to me. With. My. Mind. (Spooky.)


Each morning before my day’s work I was so focused on “my magic number” – the number of people I wanted to sign-up to the charity I was given. At first it started as a game. I promised my boss I’d get 8 for him. Then I stretched a little further. And further still. Bigger numbers. Bigger numbers consistently. It was exhilarating.


Until I got scared.


It makes me laugh now to think of how scared I felt. It was the first time in my life where everything I’d read about manifesting your reality was actually coming true, with astonishing accuracy. I didn’t want to confront that I had that kind of power. At the time it felt much safer to consider things like luck or things happening to me, rather than me being the driver of my reality. (Confession: I’m still not entirely at ease with this revelation.)


You are that powerful. We all are. But here’s the thing… Most of us are too hesitant to fully admit it. It’s easier to give up the intensity of focus required and not take full responsibility for our results.


Because as the sage Spider-man wisdom goes… “With great power comes great responsibility.


Which brings me to the final secret I’m sharing with you today.


Secret # 3: Perhaps, don’t do it.


Don’t sell anything to anybody even if you can. In the long run it’s probably not an ethical, enjoyable or sustainable practice (unless it’s for charity, right?)


The art of selling requires you also learn the art of discernment. I moved from embracing the “I can sell anything to anyone” mantra to eventually embrace the mantra I still hold today: Sell only to those who will truly benefit.


Because, sometimes to stand back and have the courage to say “actually, I don’t believe this particular service/product/event is the right fit for you” is a much better strategy in the long run. It establishes you as a trustworthy person.


My advice: Don’t go for any ol’ sale… even if you can get it. Aim for quality relationships I say. And keep making services + products that actually make a difference.


(If you’re reading this right now, I know you will.)


Your Turn: I’d love for you to share (in the comments below) your number 1 insight or aha moment from reading this post.


Kate XO

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One person has commented
  1. Margaret Monro says:

    Thanks for the chance to reminisce. I enjoyed reading this post. Always wondered why you took that job, Kate. My main memories of that time revolve around how tiring the work was and how dirty the streets of London were and no doubt, still are. Good to see you making use of the experience in such a positive way.

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