I was queuing to pay for a yoga class when I recognised the teacher from his missing eye. I knew – from articles he’d featured in – that he’d lost his eye in a surfing accident. A keen surfer and international yoga teacher, Mark Breadner was someone I admired and wanted to get to know.

When I got to the front of the queue, I introduced myself (full name, thankyouverymuch) and told him what I did. I gave him my ‘elevator pitch’. Mark immediately asked whether I would train his upcoming yoga teacher trainees. I’d never done group training before, though I’d been teaching yoga for years and had trained one-to-one with new tour leaders when working as a tour leader in South-East Asia.

I said yes. This was my entry into training – which I’m gainfully employed and still loving, eight years later.

Introducing yourself to strangers is difficult (yes, even for me). Pitching yourself to strangers is up there with doing your back taxes. And asking favours of strangers? Shoot me now.

There’s a lot that could go wrong (in real life, not just in your imagination) so let’s start with what not to do.

What *not* to do

I used to sit next to a woman at my children’s swimming lessons several years ago who owned a Pilates network. She was overly-familiar due to having seen me on the internet.

Skipping the getting-to-know-you questions, she went straight for the ask – could I write for her, for free? In exchange, I’d have my writing in front of her list of 200 people. I started to dread seeing her.

It was an unfair exchange which also lacked social graces. If the woman had taken time to get to know me and what I needed and was interested in, she could have made me a better offer.

When you’re approaching someone, don’t:

  • Suggest you meet someone so that you can pick their brain. Our brains are expensive (and tired).
  • Talk about yourself and what you’re doing and fail to ask them any questions.
  • Ask to meet face-to-face when a phone call or an email exchange might be better and easier.
  • Ask general, open-ended questions such as “how do I do what you do?” that are too hard to answer.
  • Ask questions that could easily be answered by Google.

Look around to see if you can be introduced

A warm lead is always better than a stone-cold one. LinkedIn is a great place to see who you’re connected to and to use this to connect with other people. Think of LinkedIn as a search engine disguised as social media – see who you can find at an organisation that you want to pitch to, or companies or job titles that are relevant to your pitch.

Most people passively scrolling through LinkedIn overlook one of its key benefits: one-to-one messaging. It’s perfectly appropriate to talk to strangers on the internet, whether via LinkedIn, Twitter, email or elsewhere, so long as you use etiquette.

Online etiquette when meeting new people

Typically, etiquette which applies offline also applies to online etiquette. Use people’s names (and don’t misspell them), ask people intelligent questions, look for commonality between you, be gracious and generous, and seek to be memorable by sharing something quirky, different or valuable.

It’s really easy to be generous – you simply need to be interested in others and learning what they want or need, rather than assuming. Then it’s as straightforward as forwarding them a link to a relevant thing you’ve stumbled across on the internet, a person, an event, or anything else.

Make your ask

Ideally, you’ve had some interaction, no matter how brief, before you make your ask, put forth your pitch or plead a favour.

First: make it short. Brevity is courtesy.

Second, remind them briefly of your credentials relevant to your ask.

Third, make it specific. If you ask someone to meet you to talk through “possible collaborations” that spells time and busy people have this in short supply. Don’t outsource your creative thinking to the person you’re asking the favour of.

Do people a favour: follow up


Fourth, follow up – this is hugely important. Following up isn’t pestering people; it’s being helpful. People are busy. They’re distracted. You aren’t their first priority (you’ve unlikely made their top 10). So make it easy for people by following up in a timely manner.

How often do you follow up? Until they tell you no.

Getting over yourself

The magic of asking, eh? It’s amazing how good we are at avoiding it and how incredibly things turn out once we get over ourselves and ask.

Your socialisation may well have taught you the opposite: don’t ask, don’t assume, don’t put yourself first, don’t pester. Be likable, be agreeable, be patient, wait to be asked. Ha! Patience is not a virtue in business, in fact, it’s our impatience with the status quo that may save the world. Patience keeps the status quo in power.

The biggest challenge with sales, pitching, and big, fabulous opportunities is having the ovaries to get over your inhibitions and ask. Your desire needs to be bigger than your fear; your drive must overcome your pride. You never know what wondrous things await otherwise.

Ready to amp up your courage and create your own opportunities? Join our Life’s a Pitch! challenge.