Why this Pitch Expert advocates you get a free coffee everyday, to skyrocket your professional development

Why this Pitch Expert advocates you get a free coffee everyday, to skyrocket your professional development
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“I just got a free prescription”, an email pops in.

I chuckle, but I’m not surprised.

My friend Andrew Tollinton is a seasoned entrepreneur and an expert in pitching. He’s pitched deals from £300 to £30,000,000, lectured in top London universities, and coached people to pitch everything from investment on Dragon’s Den to artificial intelligence to coffee plantations.

As someone who never knew how to ask for favours and who was frightened of speaking to strangers up until two years ago, I’m curious about pitching.

Whilst most— including my old self— see ‘pitching’ as a dirty word, it’s something we inherently do when we try to persuade someone to see our perspective, or want to be trusted. Pitching is commercial codeword for ‘persuasion’ or ‘negotiation’. And like it or not, persuasion is the process by which strangers become our closest friends.

Pitching is what we do more often than not.

So I asked Andrew about the simplest way anyone can practise pitching, and we concluded that it comes down to the everyday stuff. The stuff you hear everyone getting, but still feel like urban legends— aeroplane upgrades, free makeup at Harrods, and halving your broadband bill.

Andrew has a simpler suggestion. Learn how to get a free coffee everyday. In fact he gets free coffee at least one in four times, and he doesn’t even need to overtly ask. And, it’s something that he accidentally stumbled upon, before studying the patterns.

Consider this simplistic view— we have two selves. When we put on our professional selves, we can justify doing a lot of things, even if we’re fearful. Think about the last time you gritted your teeth and presented. But when it comes to our personal selves, we do not have the carapace of ‘in the name of work’ to crouch behind. So we’re less likely to speak to strangers and ask for personal favours.

But when you can tackle the simple everyday stuff, learning how to pitch yourself in business and career becomes second nature, and more importantly, feels real. As someone who’s scored aeroplane upgrades, free makeup and halved broadband bills, amongst others, I can attest to that wholeheartedly.

Here’s Andrew’s formula.

As someone who’s successfully negotiated her bank and utilities fees down, I learned from my mentor Ramit Sethi that you should always use the words “I’d like” instead of “Can you”. So I was pleasantly surprised when Andrew’s magic words are “Would you mind if I also had a latte”, when he orders at a café.

He explains that that when you suggest to your server rather than order them, it puts them in a position where they’ll feel at liberty to respond to that request.

In other words, they’d be happier to grant your wish, rather than accede to your order.

Andrew says that for maximum success in getting your first few free coffees— and in that upping your confidence— you should consider the following factors:—

  • Age: People in your age bracket are likelier to relate to you, so they’re likelier to respond positively. Teenagers are less outgoing and more concerned about themselves, so avoid them.
  • Disposition: Ask yourself, if they are in the right place to think about others. If they look despondent, then asking them to give is a stretch for them. In contrast, someone who is on their front foot, attentive and with good contact is likelier to give you a yes.

“Be high contrast, be of a different mould”, Andrew advocates.

He is likelier to get free coffees if he is dressed smartly, for instance in a suit and tie, especially if the café is not used to getting people dressed that way.

Also he recommends that servers who display a unique identity through their appearance are likelier to respond positively if you’re well-dressed.

“If I approach someone with bright hair and piercings and I show effort in how I dress, I am likely to get some appreciation, even if I am wearing a suit. People don't need to look the same, they need to share the same attitude”, Andrew comments.

You’re likelier to score your free coffee if you visit the café before or after their high-traffic times, Andrew says.

This is because they’re likelier to be in a relaxed mode.

According to Andrew, chains are likelier to have discretion to grant free coffees. In fact, they have a certain quota that they are allowed to give away, especially if the coffee is an add-on to your order.

In my experience— before I learned how to request for free coffees— independent coffeeshops and restaurants also give you free gifts in other ways.

A memorable recent experience was when an upmarket seafood restaurant gave me three ‘stamps’ on their rewards card, even though I hadn’t even spent enough to qualify for one stamp. Similarly, I’ve been gifted such treats at independent coffeeshops, and free cakes, which are in essence worth more than than coffee.

At the foundation of every interaction is to treat someone else as a fellow human being.

Consider how you’d like to be treated, rather than to see every exchange as a transaction, even if you’re in a rush.

Smile at your server, greet them by their name, and engage in a conversation with them.

It can be as simple as asking them how’s their day been, or what would they order if no one was looking? The latter question always makes people laugh, and you’ll be surprised at the wonderful rabbit hole of gustatory delights you’ll tumble down.

Put simply, Andrew explains that when you treat your server as a human, you get out of the frame of “How are you going to serve me?”.

And when you move them out of standard protocol, people are likelier to treat you better.

Besides, spreading a little warmth always makes the world a better place.

When we chatted about free coffees, Andrew repeatedly spoke about breaking patterns. From looking different to treating your servers differently, it seems that pattern breaking underpins his approach.

It is something he’s honed and learned from his friend, who’s a member of the Special Ops.

Using an extreme case, terrorists tend to perform roles. Nearly all mass shootings have been prepped for years in advance, where they have undergone numerous rounds of simulations. However, when a defendant responds unexpectedly, for instance appealing to the universal concept of ‘mother’, they are likelier to humanise the terrorist and obtain a dispensation.

Similarly, we are governed by patterns, even if we don’t recognise them overtly.

Citing Naturalistic Decision-Making Expert Gary Klein, Andrew explains that what we call intuition is predicated upon how we recognise key patterns. But because patterns can be subtle, they often difficult to verbalise or formulate.

What matters most is that when you break the patterns of people’s expectations, you turn something that is computational and logical, into an emotional state where people are open and less guarded.

When Andrew coaches people to pitch, he uses his lessons from scoring free coffee.

Even if an investor says that they only invest in certain types of businesses or those with certain value, they are merely acting based on their pre-established patterns.

If you take their words on face value, it’ll stop you from pitching. However, what people say they do and what they do are two vastly different things.

Therefore, Andrew will switch up what he does. Investors may expect you to be forceful, so act differently, down to your body language. In essence, recognise when you’re being caught in a pattern, and this will make the other party less guarded.

That’s a pretty amazing way to grow, all from scoring a cup of free coffee.


To learn more about Andrew, go here, or join his free Facebook group. Too nervous about pitching or speaking, and think you need to be Tony Robbin’s carbon copy before you can succeed? Go here to chat with Dr Perpetua Neo to create your own authentic, coherent voice.

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