Lesson 8: Creating a Winning Pitch

What You’ll Learn: Making a successful pitch requires you to get into your client’s mind and solve their problems with what you are offering. As a creative, sales can be one of the most challenging things you can do, in part because you are selling yourself as much as what you are promising to deliver.

Creating A Winning Pitch

“The worst enemy to creativity is self-doubt.”

~ Sylvia Plath                      


One of the hardest things for a creative to do is reduce everything they do down to a 10-, 20- or 30-second elevator pitch that leads to a sale.

Whether we like it or not, people buy from you because they believe in you. If the client or customer can’t connect with you on a personal level, it doesn’t matter what you’re trying to offer them. A pitch is designed to start a conversation, which, if everything goes right, turns into a negotiation. This requires you to do your homework, understand a bit of psychology, develop interpersonal skills that capture someone’s attention and engage in a bit of showmanship, especially if this is a first impression.

These days, the pitch may not even be in person. Because of the pandemic, people have become comfortable with Zoom and Teams meetings, emails and other digital interactions. Who knows when people will become comfortable with face-to-face meetings and the oldest dealmaker in history – the handshake.

Even though sales norms have changed, the pitch remains the same no matter how it is delivered. It is your chance to rise above everyone else in the marketplace, grab the attention of a prospect, prove that what you are offering is what they are looking for, and remove any doubt in their minds that you are the answer to their prayers or at least, the solution to their problem. When a pitch is well-executed, the prospect doesn’t even know they were being sold to.

Easier said than done, you say. Creatives are famous for being able to sell everything but themselves. Perhaps because it’s all so personal. What you create is a part of you. It’s not a thing, like a house or a car. If it is rejected for price or any other reason, it can be devastating on so many levels. Just ask any Broadway actor who’s been turned down for a part they thought they were a shoo-in for.

A pitch should capture the attention of your audience at the very start. It should pique their curiosity and draw them in. It’s like telling a very short story. It captures their imagination, draws them in, and they can’t wait to see how it ends. In this extremely short window of time, they are on the edge of their seat, intrigued by what you have to say and are ready to know more because you sold them on the idea of working with you.

You haven’t made the actual sale, but you’ve moved to the next step. It’s like hooking a sailfish out on the open sea. He’s not in the boat yet, but you have the chance to land him. By the time you are done with the pitch, you have set the hook, and the prospect is on the line. From there, it’s a matter of demonstrating why you are the first and only choice. Every objection is met with a proof point and a benefit or feature. All that’s left is to close the deal and work out the details.

There is no single formula for a winning pitch. But that doesn’t mean you have to start from scratch. You can copy, borrow, edit and customize a basic pitch to make it your own. Each time you deliver it, it gets a little more natural, and you don’t even have to think about it. It’s like knowing the chords or lines to a song; it becomes rote but not mechanical.

Pitch Basics

Every pitch has the same characteristics:

  • An effective pitch balances business and personal needs. A pitch that is all about you and your creative ideas won’t make a connection with the person you’re pitching to, and neither will one that is based purely on emotional desires.
  • A pitch needs to be succinct. It’s like meeting someone at a party you might like to date. You have a few moments to catch their attention and give them a reason to continue the conversation and eventually get to ‘yes.’
  • Pitches are devoid of flowery speech, superlatives and braggadocio. These don’t make an impact and, worse, may close a door before it opens.
  • The foundation of a pitch is a compelling story. Data isn’t story. No one cares how many theatrical productions you’ve been in or that you know so-and-so. People want to know why they should give you a few more minutes of their time, why you may be just what they’re looking for, and why they should care about you as a creative and a potential supplier of a service or product.
  • The focus needs to be continually on your customer or client and their problems and needs. You need to hone in on this and then become the solution. Ultimately, people want solutions, whether it’s a new piece of art for their home to fill a void on a wall or someone to star in their next play who can sing and be a romantic lead.

That’s a lot to pack into a pitch, there are ways to refine your message and make it more concise, so it grabs your audience. Remember, you’re approaching this as a business that has something of value to offer, not as a creative who may need to pay rent next week. There’s nothing wrong with focusing on the near term – creatives do it all the time – but operating as a business requires you to think long term, creating a pool of regular customers who come back to you again and again rather than a one-time sale to fill a specific need.


    1. Know your audience. Every prospect is different. The more you know about them and what they need, the more effective your pitch will be. Resist the temptation to deliver a generic pitch. It will sound mechanical and rehearsed, which of course, it is.
    2. Focus on the results, not the features. Prospects won’t appreciate the features as much as you do. They want to hear how your product or service will solve a problem they are facing. Don’t bore them with the details. There’s plenty of time to do that later. Focus on the job it does and how it solves the customer’s specific problem.
    3. Think of your pitch as a job interview. In some ways, that’s what a pitch is. It’s your chance to demonstrate that you can deliver what the prospect needs. As a potential customer, they are looking to “hire” someone to solve their problem. Show them how you fill that role and meet their need. You need to make yourself relevant, if not indispensable.
    4. Go deep into your customer’s needs. To be truly effective in a pitch, you want to show that you understand their problem or problems from all angles. The apparent problem isn’t necessarily their most costly or vexing one. Demonstrating that you clearly understand the issue at hand will help you connect with your prospect on an emotional level.