I walked straight into a guy wearing an official-looking lanyard in a coworking office I was visiting. He appeared to be touring another woman around the place. Maybe I assumed I needed to speak with him, or maybe he caught my eye with a ‘come hither’ look, I don’t know.

We had an awkward chat. He asked for my name; I told him I was a business coach; he told me he was one, too.

Within an hour of our meeting, he’d linked up with me on LinkedIn, followed me on Instagram, sent me a Facebook friend request and an audio message. I felt overwhelmed and put off. He made his politics and affiliations clear on his LinkedIn profile headline, so I could easily see that he “wasn’t my person.”

A bad pitch feels a bit like this. Too much, too soon, too intimate – a total mismatch, which the other person seems oblivious of. The majority of pitches? Deleted, sight unseen, like the five emails I deleted this morning, and every other morning.

Too many bad experiences of pitching and it’s no wonder that most owners would rather poke a fork in their eyes than consider sending a pitch.

This is a crying shame, because one short, sharp pitch can change your business overnight. The reason my challenge is called Life’s a Pitch! is because pitching should be normalised: we pitch our children on one more episode only, before bed. We pitch our spouse on a new dining table, or a holiday. We pitch our friends on what restaurant to eat at.

My very first client, fourteen years ago, before I had an ABN, website, or any idea what I was doing came through me confidently introducing myself. Within four months of starting, thanks to his business and a few others, I was earning my old PR salary, except this time as a digital marketer.

How I began training business owners? I introduced myself to another owner (with the formula that I’ll be sharing in the Life’s a Pitch! Challenge) who immediately asked me if I’d train his group in how to start a business.

Selling courses around Australia? I used to send cold emails to people who didn’t know me, telling them I was coming to their hometown (Adelaide, Byron Bay, Melbourne, Brisbane, Newcastle) and inviting them to check out my course.

Landing new custom training in the middle of 2020, which was a $10,000 job? I sent an email to an info@ email address.

And then there are the countless business friends I’ve made because I finally got over myself and plucked up the courage to say ‘hi’.

Why we find pitching hard

If you’re not someone who struggles to introduce yourself to strangers or pitch for opportunities, then great! This article is not for you.

But if you find yourself constantly putting the kibosh on your dreams, then guess what? Your doubts aren’t the truth; your doubts were planted by others.

I don’t know about your upbringing or education, but nowhere did I learn how to ask directly for what I wanted and single-mindedly pursue my dreams.

Like many, I was told to be patient. To wait to be chosen. To seek external validation (through education, awards, etc.). To not be ‘full of myself’. To not be ‘too much’.

I’m not alone here. I see my clients pursue every certification and qualification around, and still deny themselves the courage to charge the value they offer. Something’s got to give.

Pitching DOS and DON’TS

First, what NOT to do:

  • Sir/Madam’ earns you an automatic delete
  • If it’s easy to find, use the person’s name and double-check the spelling
  • Don’t insult the person you’re pitching
  • Don’t shame the person you’re pitching
  • Don’t quickly demonstrate that you have no idea what the person you’re pitching does for a living
  • Don’t demand the person get back to you
  • Don’t suggest you want to pick the person’s brain
  • Don’t waffle on about yourself or your company.

Pretty easy, right?

Effective pitching:

  • Addresses the person by their name and always double check the spelling
  • If you’re sending an email to a generic address such as info@, ask politely for the recipient to put you in touch with the best person for your specific request
  • Is brief – brevity is courtesy
  • Demonstrates some detail that shows you know something about the person or business
  • Is specific in what you’re asking – don’t put the onus on them to try to figure out what you want
  • Makes a small ask (don’t ask something you can easily Google)
  • Doesn’t assume how people prefer to communicate – instead it gives them choices on how you could communicate in future, such as via phone, coffee, email, lunch, etc.
  • Gives some value, even if it’s just a sincere compliment
  • Always ends with a question, to keep the conversation going.

Backing yourself

Whether you want to join our Life’s a Pitch! Challenge to get better at following up, making new online business friends, pitching strangers, or asking existing or old clients for more work, at the heart of pitching is having the audacity to ask.

And to ask, you need to back yourself.

Nobody is going to back you in your business if you don’t first back yourself. Few people will try out a fledgling business owner who sounds unsure of themselves. Nobody is going to give you what you want unless you stand up tall and ask.

While participating in our Life’s a Pitch challenge may land you new clients, opportunities, business alliances, friends, publicity and money, there’s something even more valuable within reach.

Pitching invites you to advocate for your needs. To be clear. To be articulate. To take the time to get to know the other person, through the process. To demonstrate confidence. To be willing to outrun your fears. To back yourself. And to get what you want, without waiting (and waiting, and waiting).

Everything you want is on the other side of asking. Won’t you join us?