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How to fearlessly pitch and sell without feeling weird

Your business success demands colossal sales skill.

No entrepreneur can avoid it. No matter how it makes you feel, you must be come an expert salesperson. Even startup technologists building software in their code-caves have to persuade investors to sign cheques.

It’s no surprise that – sooner or later – I talk with all my clients about sales. Money does strange things to people and when talking to customers about it or asking for it… things get weird.

Otherwise confident entrepreneurs start second guessing themselves. They hesitate and choke. What was friendly conversation becomes stilted and awkward.

You can’t ask for the money when things get strange. You can’t handle objections when you feel awkward. You can’t close the deal when you’re acting weird.

So here’s a guide – that goes straight to the heart of the mental root of the weirdness – that’ll show you how to never mess it up again. 

“So this meeting today went south on us. It was weird…”

It was 11am on my last day of my beach vacation. I was standing on the veranda of our seaside condo, fielding an unscheduled call from one of my oldest (and most beloved) clients. I gazed only somewhat longingly at the rolling waves in the distance.

My client and his business partner were in New York battling the humidity and tourists in an attempt to nail a quick succession of meetings with key clients in the entertainment industry.

Done right, they could land a contract, solidify key relationships and move big bucks and prestigious projects into their eager hands. While I was chilling on the beach, these guys were deep in the business-to-business sales hustle.

“This last one knocked us around a bit and I needed to talk to you. I need a reframe or something because this isn’t working.” 

There’s no experience that feels quite as rough as getting rejected while attempting to sell your OWN thing. Employee salespeople will never understand; when the product you’re selling is your creation from end to end, hearing “No” hurts. Like a swift kick to the solar plexus.

“I dunno man, we keep asking these guys what projects are coming up for them but they’ve heard that question a million times. It’s like they know it’s us asking for their business and they get cagey. You can feel it!” 

The only thing worse than rejection is inevitable rejection – walking right into it knowing that it’s coming

My client was smacking into a very common brick wall: When you pitch people who are regularly pitched, they see you coming a mile away. You can almost see the word “No” –awkward and weird that it is – coagulating in their eyes before it hits their lips.

The dirty shame of asking someone for money

The problem – and the crux of this article – was the way my client was moving a friendly meeting toward the close. It was awkward and uncomfortable for both parties while also being all too (painfully) familiar to the prospect. And it wasn’t working.

Asking to do business with people evokes a crazy pulse of shame in almost every entrepreneur. Even the very best get flushed, or break out in sweat. There’s a cumbersome and clumsy conversational juxtaposition where chit chat stops and the asking-for-your-money begins.

That source of the shame comes from a couple of places…

The first is our deep belief that people don’t wish to be sold. We believe it because it’s true – we’ve all ducked the guys with clipboards on the street corner. No one wants that.

The second root of shame lies, ironically, in our focus on the person sitting across from us. Sales gurus and trainers have told us to focus on asking questions and, above all else, ensuring the prospect clearly understands “what’s-in-it-for-them”. Relentless community to these principles causes unwanted side effects, as you’ll see.

The good news is that there’s one simple technique – one basic conversational tactic – that nixes both those problems and frees you up to avidly speak to your prospect about buying your stuff. With volition, passion and enthusiasm. And no weirdness. Guaranteed.

Tell your prospect why you want to work with them

There is one precise moment, in every sales interaction, where it’s okay to take the focus off your prospect. In that moment, it’s fine to forget what’s-in-it-for-them and it’s even good not to ask questions. In fact, feel free to talk all about you.

When you want to ask someone for their money, tell them why you want to work with them.

Read that sentence again and imagine I bolded the word “why”, and also “you” and also “them” – because every one of those words deserves special emphasis. Tell them why you want to work with them.

So many entrepreneurs – even those who consider themselves pro salespeople – attempt some weird verbal judo as if they’re trying to trick their client into talking about signing the deal. As if asking “What do next steps look like for you?” or “What projects do you see needing assistance with?” is some code that’ll allow you both to go on pretending you’re not talking about money.

Come right out and explain why – your rationale – you want to work with them. What is it about them, either as an individual or as a company that lights you up. Why do you feel that you want this gig. Be transparent about expressing the extent of your passionate desire to work with them, for reasons more emotionally compelling than money, and something magical will happen…

All the pretense will vanish. The awkwardness will evaporate. Your prospect will talk to you directly about doing business together, for money.

The key to all of this, of course, is to only be pitching people (or companies) where you have a clear compelling desire to win the business for reasons beyond the cold hard cash.

Genuine desire gets sales 

For my client in entertainment, it was simple: They were already pitching companies whose work they absolutely loved, they just hadn’t TOLD them. Following some weird unwritten sales script, they assumed they had to keep their passion hidden. Instead, they were asking their prospect about future projects in an attempt to (awkwardly) bring the conversation around to the “please pay us to help you with things” part.

Once they started communicating that while the money might be important, they were excited to be here in THIS meeting asking for THIS deal because they were in love with the prospect and everything they do and couldn’t scarcely contain themselves with excitement to find a way to work together… things got better.

It’s not that you have to gush. The above example is deliberately hyperbolic.

There’s classy ways of communicating the critical Why-You and Why-Them rational. Even subtly done, it’ll still serve as a smooth and transparent reason to ask directly for your prospect’s business.

I’ve even seen it done by a salesperson/entrepreneur taking a moment out of their pitch to explain their company’s five year vision. When they explained why bringing on the particular client (in front of them) was such a big part of that vision, they made it effortlessly clear that they were there to ask for money.

Gushing or strategic, the point is the same: You want the prospect and you’re not afraid to say it.

Done right, with class and sensitivity – after building rapport, asking all the right questions and really focusing on the What’s-in-it-for-them – telling your prospect why you want their business will flatter them just the right amount.

What happens next will be the most candid, open and useful conversation you’ll ever have with a customer about either; what needs to happen in order for them to close, OR the real reasons (objections) why they won’t be able to do business with you today. Either way, you win.

That it’s. It’s the sales coup de grâce of getting to the point. It cuts through bullshit, eliminates weird awkwardness and makes it easy to ask people for the money and then talk intelligently about when they can give it to you.

When I do this with clients who sign up for and complete a Test Drive Consult, it usually goes something like this:

“I’ve been booked solid for a while now, but if you’re interested… I’d like to check my availability and offer you the next opening on my client roster. 

I want you as a client because the industry you’re in is fascinating to me and your grasp of your own psychology – and where’s it’s holding you back – is so good that I know with a few strategic nudges we’ll be able to produce huge results. 

Frankly, I want to be able to say “I did that” when the shift happens. It’ll make me look good, and it’ll be fun. Plus, I’m going to secretly learn all about your industry and business model – through osmosis – while we work together. 

So I’d be really stoked if you signed up for a monthly retainer. What do you say?” 

Now that’s an amalgamation of the last few conversations I’ve had like this, because in real life (and this is the point) every expression of my desire-for-a-client is different. They have to be if they’re to remain genuinely truthful. There’s no template for giving a shit, and I have to honestly want the client for a reason beyond the bucks.

Once you try this sales tactic once, your mind will be blown by how effective it is. Then you’ll realize that the real point of this article – and my secret agenda all along – was to trick you into doing meaningful work with interesting people that you care about.

It’s no accident that doing so makes selling ten times easier.


+ Add Comment
  1. “There’s no template for giving a shit, and I have to honestly want the client for a reason beyond the bucks.”

    I think that honestly wanting a client for reasons beyond money IS the template for giving a shit.

    As always, your timing is perfect. Thanks!

  2. I got the intro to your post and thought, yeah, right, what could he possibly say on this subject that hasn’t been said a million times. “When you realize what it is, you’ll want to smack yourself in the head.” OK you got me. Because what you have to say is generally brilliant, I was compelled to at least go take a look. Wow. It really HASN’T been said a million times. It’s so obvious, yet it’s the last thing we think of, if we ever do. One of the most important posts ever written…for me anyway. Am I gushing…sorry. I’ll just say thank you, add that I love your website (colors, artwork, etc.) and shut up!

    1. Hi Carole! Glad I had you hooked line and sinker on this one – it IS super important and no one is talking about it. That’s why I wrote this post.

      It’s OKAY to admit you WANT to do business with people! 😀

  3. as always perfect timing, as I am fighting NOs in my quest to presell SaaS to some tough clients.

    Thanks Peter!

  4. This is a great technique that gets you to look at pitches as CONVERSATIONS instead of TRIALS. Viewing the exchange in a collaborative context is a much kinder, mutually beneficial way to approach it. After all, both seller and prospect must benefit from a contract if they’re going to work together. Bravo on an excellent re-framing, Peter!

    1. Thanks TR! The conversation distinction is essential – the worst pitches are the ones where the (amateur) salesperson acts like it’s their job to talk for the whole meeting!

  5. Thanks Peter, a great article and another golden nugget of information to help us understand our social sales interactions that little bit better, Cheers!

  6. For me its always been very obvious about building rapport but I never thought a lot about the explaining why you want to work with them. I have done it when its true and can clearly see it works , but its not always the case and those are probably the clients you might want to pass on and target the right ones even more. Great info again! Thanks Peter

    1. Hiya Ben! Thanks for stopping by. Yes, rapport is a great first step – a lot of people BREAK rapport by pushing a sales agenda in some weird back hand way. This lets you do it directly without losing rapport.

  7. We’ve just completed our first year in business. I thought parents would flood into my learning center getting the much needed support for their kids. Boy was I wrong!

    Fine tuning my sales pitch has been interesting. I finally realized, after a year, that I have to build a relationship with the client, explain why their child needs our services, and ask them for their business!

    Thanks for all of your articles. They have helped me tremendously throughout this challenging first year!

    1. Hi Angela! I remember when I made this mistake with my first therapy practice – turns out just having an office doesn’t entitle you to clients! 😛

      Glad you’ve gotten good mileage on the blog here – thanks for commenting!

  8. Great stuff Peter!

    I think this comes under the banner of a really big theme – “relationship marketing” Making your clients know that you are interested in them beyond seeing them as a big dollar sign sure does help to engender feelings of comfort and trust, which are useful in getting them to engage in business with you!

  9. I am SO glad I was sitting down, or I would have fallen over… This is the first truly NEW sales how-to info I’ve heard in 25 years. I cannot wait to apply this idea – Thanks !!

  10. Great post. However, not entirely ground breaking information, basic people skills dating back to primate man.

    “We are interested in others when whey are interested in us.”
    – Dale Carnegie

    Taken from his ‘best selling’ book: How to Win Friends and Influence People.

    A must read for any serious Salesman!

    Yours for success,


  11. By the way I like the way Peter has put this across. Which reminds me of another highly important quote:

    “Common sense is not so common.”
    – Voltaire

    Yours for success,


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