What I learned About Pitching from my Caribbean Vacation

What I learned About Pitching from my Caribbean Vacation

Over the holidays I was lucky to go on a once in a lifetime trip to the Caribbean. My family and I took a ​Windstar cruise​. The ship was beautiful, the service stellar, and the food delectable. Surprisingly, the Windstar crew taught me four key things about pitching.

It’s Easy to Pitch When You Have a Great Product

The Windstar crew focuses on extraordinary service with a smile. You feel spoiled the moment you step on the ship. The cabin stewards leave flyers to sign up for another cruise and there is a cruise consultant on board. They offer a discount if you book a cruise while cruising. None of these approaches felt sleazy or salesy because I was having such a good time. And the crew members’ enthusiasm is genuine.

Use the Cruise Way: Make your story shine and it will be fun for you to pitch and fun to listen to.

Connect with Your Audience

Even though we were only on board a week, the crew from the the captain and general manager to the servers and stewards, learned our names and were always excited to see us. They made the passengers feel special.

Use the Cruise Way: Whether you are pitching in person, with a pitch deck, or on a sales page, how can you make your audience feel valued? What can you do to turn them into fans? Tell a gripping story that they connect with emotionally. It may be your idea, but the audience is your boss. Always over deliver.

Make Your Pitch Feel Like a Party

The Windstar people loved what they did and made pitching fun. They threw two parties where they pitched other cruises and asked for good reviews. One was a Tahitian cocktail party where they talked up their signature cruise to Tahiti. The other was the captain’s farewell dinner where the passengers got to applaud everyone that had been taking such great care of us. Both were lots of fun.

Use the Cruise Way: Make your pitch feel like a party! Be entertaining and fun. Think outside the box. Can you bring a snack that fits in with your project? Or ask to have your meeting outside? Be fun and memorable.

Take Every Opportunity to Pitch

And finally, always be pitching! Yes, they pitched us every day, but it was not overkill. Every pitch felt authentic. The climax was one of Windstar’s other ships sailing by us with her sails full on our last night. Talk about a movie moment!

Use the Cruise Way: ​Be ready to pitch anywhere, anytime.​ Don’t miss your movie moment.


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Be Ready to Pitch Anytime, Anywhere

Be Ready to Pitch Anytime, Anywhere

September is marketing month! One of the most important pieces of your marketing is being able to talk about all of your projects. My challenge for you this month is to craft killer project cocktail pitches for every single one of your projects.

While this challenge seems squarely aimed at the at writers, it is also important for executives to be prepared. One time my boss turned to me in a meeting and spontaneously asked me to pitch our entire slate to investors. Even if you are in something very traditional, like finance, you still need to talk in a compelling and memorable way about what you’re working on. And that is where the project cocktail pitch comes in!

I know a lot of you are on strike and this homework assignment may feel needless. But what better time to work on getting all of your project pitches in fighting shape than when you have this extended downtime with no pitch meetings? Also, I’ve heard from a lot of you about the great networking you’ve been doing on the picket lines. As you guys know, one of the first things people ask you is what are you working on or what have you done. So I bet even though you’re not having formal meetings, you are pitching daily. And if you’re not, you should be!

You can read the blow by blow article ​here​ about how to craft your cocktail pitch. I’m going to do a quick refresher below.

First, the Boy Scouts have it right; be prepared. Be prepared to pitch any project anytime. Because when opportunity knocks, you want to be ready.

What is a cocktail pitch? A six sentence description of your project that connects with the audience and gets them to say, tell me more.

Format and genre

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Your Pitching Secret Weapon – the Project Cocktail Pitch

Your Pitching Secret Weapon – the Project Cocktail Pitch

The project cocktail pitch is a short powerful way to pitch in any situation from cocktail parties to business meetings.   How do you talk about your projects in a compelling and entertaining way?  First, remember that pitching is selling, not telling.  Your goal is to sell your project, not to tell all the details of your story.  How do you sell? By getting your listeners to connect with your story and say “tell me more.”  Instead of just telling your story, ideally  you grab their attention so they want to hear more.  Think of your cocktail pitch as an audio version of your movie trailer.  The best trailers don’t show the whole movie.  They show just enough so that you know the concept and the characters and want to go to the movie to see what happens. 

Tell me more can mean a bunch of things that get you one step closer to a sale.  It can mean:

  • Send me the material.
  • Come in for a meeting.
  • Keep talking and tell me more of the story.
  • And the holy grail, I’ll buy it!

How to Craft Your Project Cocktail Pitch

1. Start with your genre & format.  By labeling your project, you let your audience know exactly what kind of story they are listening to.  Examples: Single camera sitcom, supernatural TV drama, spy thriller feature.

2. Use touchstones.  Mention successful projects that have a connection to your story.  The tried and true blank meets blank (Frozen meets the Avengers) is the most common way to bring in touchstones.  The meets technique may feel cliched, but it is a cliché for a reason; it works!  If executives hear Frozen meets the Avengers, they immediately know a lot about your movie.  It is princess superheroes in a fairy tale world.  Sold!   Another way to use touchstones is to put them in a different setting like Frozen in high school.   A third way is to mention projects that share the same audience as yours.  This movie is for fans of Frozen & The Princess Bride.  In this example, we know that this pitch is about a comedy fairy tale romance.  HINT: Be sure to use commercially successful touchstones.  It doesn’t help you make the sale, if you’re comparing your project to a box office bomb or a show that didn’t make it through the first season. 

3. Hook your audience with the emotional hook. Emotion sells.  Make your characters’ struggle relatable.  You can use a metaphor (office politics is high school with suits.)  An archetype (the high school mean girl is now ruling the PTA.)  Or ask a question.  Have you ever wondered what happened to the high school mean girl?

4. Next, introduce your main character and their emotional drive.  Katniss is an ordinary 16 year-old girl whose selfless sacrifice to save her sister’s life starts a revolution. HINT:  If you have an ensemble, start with the group leader and then make everyone archetypes.  (The Con Man, the Optimist, The Brains.)

5. Then onto the Story Appetizer, which is 3 to 5 sentences about your story.  Here is where you can share a bit more about the main character, what they are trying to accomplish and how they do it.  If you need to, here is where you can talk about the world of the story and the bad guy.

6. Finally, end on a Cliffhanger.  Emphasize the emotional stakes.  Can your characters do it?  Will she get a date to the wedding or be at the singles table with the great aunts? Will they rob the bank so Joe can get his kidney transplant?  With the cliffhanger, you leave your listener on the edge of their seat so they say, tell me more.

Cocktail Pitch example

This animated movie is The Dirty Dozen meets the Big Bang Theory.  This is that age old struggle of the  geeks vs. the jocks and how it feels when you know you can be the hero, but you’re always overlooked. Our story takes place in the world of holiday icons where Santa and the Easter Bunny are the cool kids.  But when they’re kidnapped, the unsung holiday icons lead by Earl the Groundhog from Groundhog Day, must rescue Santa and save Christmas. Will our group of ragtag heroes be able to work together and get Santa back to the North Pole in time?

When do you use a cocktail pitch?

  • Networking
  • In meetings
  • In emails
  • As the introduction to your longer formal pitch

Now you have the project cocktail pitch formula, and with little practice you should feel ready to pitch to anybody, anywhere, anytime. 


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What the heck is a cocktail pitch? And why do I need one?

What the heck is a cocktail pitch? And why do I need one?

You are at a cocktail party and someone asks you the dreaded question – what do you do? As you mumble something, his eyes glaze over and he starts looking over your shoulder for someone else to talk to. He wanders off and you wish you were home watching Netflix with your cat.

Ugh networking is the worst! But it doesn’t have to be. What if you had a short and simple way to introduce yourself and what you do that was memorable and dynamic? A way to connect with people that made them say “Sounds cool. Tell me more.” Wouldn’t parties, networking events, and business meetings be easier? This is a cocktail pitch. And once you know how to do it, talking about yourself becomes a breeze and meeting new people fun!

This short and sweet pitch is also called an elevator pitch. The idea is when you are alone in the elevator with your boss, you have the couple of minutes between floors to introduce yourself and your latest project. I prefer the term cocktail pitch because I think it sounds more fun and less like homework. And that is one of my goals for you – to make talking about yourself empowering, instead of cringe worthy.

Cocktail Pitching 101

There are two kinds of cocktail pitches, the personal – who you are and what you do. And the project – what you are working on. Today we are going to focus on the personal. If you are like most people, you hate talking about yourself. It feels braggy and smarmy. You don’t want to be one of those people that talks about themselves incessantly, who nobody wants to talk to, to let alone work with. Unfortunately, talking about yourself, your accomplishments, and your current projects is an important skill to build careers and relationships. If people don’t know what you do they can’t hire you, recommend you, or remember you.

Be authentic. Be interesting. Be interested.

When talking about yourself in any situation, there are three key things to remember to avoid sounding like a slickster. 

First be authentic.  While the advice to be yourself may sound corny, it really works.  If you are excited about what you are doing, that passion will shine through when you talk and make people want to hear more.  You may be tempted to embellish or even make up stuff to sound important.  Don’t.   You will probably seem desperate.  And if people do believe you, you won’t feel great about yourself and it will drain your confidence.  Instead focus on what you’re doing.  You can talk about what you’re working on, who you’re working with, or what your company does.  If you don’t like your job, you can still have a great cocktail pitch.  Mention your job in passing and focus on your favorite aspect of your life instead.  Whether it is coaching your son’s soccer team or spending your weekends as a Civil War reenactor, talk about your current passion.  You never know where it will lead.  Maybe your college buddy at the reunion is a Civil War buff too but is looking for an accountant and you get a new job out of one conversation. 

Second, be interesting.  Don’t just rattle off a couple of sentences when you introduce yourself.  Slow down, look who you are talking to in the eye, and vary your tone of voice.  To hear what you sound like, try videoing yourself and practicing in the mirror.  Let your personality shine when you’re talking.  So many people turn into stiff robots when they introduce themselves.  Be your awesome self!  Remember there is no one else like you and that is a good thing.  You may be the answer to this guy’s prayers.  He may be looking for someone with your exact skill set or point of view.  To stay engaged, sprinkle your cocktail pitch with a couple of interesting fun facts.  Is there a funny way you can describe what you do?   Is your latest project something everybody knows about like a bestselling app?  Have you been interviewed on a podcast lately?  Everybody has something interesting about themselves!  If you are having trouble coming up with something, ask your family and friends to help you brainstorm.   Sometimes things that seem ordinary to us are fascinating to others. 

Finally, be interested in the person you are talking to.  The best way to be authentic when talking about yourself is not to do it for too long.  After you have introduced yourself with your cocktail pitch and chatted for a couple of minutes, put the focus on the other person.  Ask them about themselves, listen, and ask questions.  Is there any way you can be helpful to them?  Simple things like recommending a restaurant or a book help build connection.  Before you know it, you will be in a conversational flow. 

Your Cocktail Pitch is your foundation

At first using your cocktail pitch to introduce yourself will feel uncomfortable, but the more you do it the more natural it will seem.  Practice a lot!  Ask for feedback from your friends and practice again.  Once you have mastered your cocktail pitch, you will be armed with a great tool that you can use in any situation from a real cocktail party, to a business meeting, to a job interview.  Your cocktail pitch will be a springboard to write your bio.   You can use it in emails and sales material.  Think of your personal cocktail pitch as the foundation of your career networking toolkit that you can change depending on the situation.  For instance, in your annual review you will talk about yourself differently than at your kid’s birthday party.  With your cocktail pitch as a touchstone, you will be ready to network in any situation. 

How to write your personal cocktail pitch

Step 1:  Your logline

A logline is a one sentence description of a movie or TV show like the descriptions on Netflix. You also have a logline about who you are and what you do. It is a great way to start when you are introducing yourself. A personal logline has more pizazz than just saying your profession. Think about it. If you meet someone and she says “I’m a lawyer.” Don’t you immediately tune out? That sentence doesn’t tell you anything about what she actually does and it’s so boring. Think about the kinds of people that are your clients or customers. How do you help make their lives easier? This approach to talking about what you do is emotional. And emotional is memorable and interesting.

There is a simple formula to help you figure out your logline.

I help (kind of people) do _________ which helps them do ____________.

Hint: Use juicy adjectives!

Mine is: “I help creative people sell their stories and pitch like a boss.”

For instance, If you are a lawyer, what kind of lawyer are you? Who do you help? Even if your clients are giant corporations, there is a way to talk about what you do that is relatable and interesting. “I am a lawyer who represents big companies. I help them become better corporate citizens and improve their customer service.” Boom! I hear that and I have a million questions. Like who are your clients? What are you working on now? This personal logline will naturally start the conversational flow. Much better than the standard intro “I am a corporate lawyer.”

If you are an artist, what kinds of things do you write, paint, or create? Be specific and again include the emotion in your work. Some examples: “I write half hour television about quirky characters in extreme situations.” Or “I am a fine artist who specializes in desert landscapes. I love to capture the changing light as it dances off the rocks.”

Your logline is a natural transition to part two of your cocktail pitch – why you do what you do.

Step 2: Your Origin Story

Every superhero has an origin story. Peter Parker was bit by a radioactive spider. Superman escaped Krypton in a rocket and was found in a Kansas cornfield by John and Martha Kent. You have an origin story too. That moment when you discovered what you love to do. What was it for you? Did you try out for the school play to impress a girl and get the acting bug? Make a stop motion movie in your basement when you were 12? Successfully argue your way out of eating your vegetables and learn the power of debate? To discover your origin story I like to use a technique called It All Started With that I learned from the wonderful writing teacher Alexandra Franzen.

You literally say “It all started with” and then tell the story that launched your passion in a few sentences. The next step is to explain how your origin story helped you realize what you wanted to do. Then round it out with what you are doing now.

So the formula is: it all started with ____________and that’s when I realized _________ and now I __________ .

To show you what I mean here’s mine:

It all started with Three Days of the Condor. I was three years old and my dad had taken me to see the spy classic. It was the climax of the film and the tension was palpable in the audience. Robert Redford was trapped at gun point by the villain. In a clear voice I called out “don’t worry, he used to be a bad guy, but now he’s good.” And that of course was exactly what happened next. In that moment my love of movies and knack for storytelling was born.
I love this technique because it makes you memorable and interesting. Believe me; people will want to hear more about you! It is also empowering to have something fun to say about yourself.

Step 3: What you’re doing now

Round out your cocktail pitch with a bit more information about what you are doing now.  Use specifics.  You can mention a current or favorite project.  Talk about a recent big win at work.  Or expand on how you or your product help people.  Hint:  If you are looking for a job, mention it here.  Again, be specific about exactly what kind of job you want and where you want to work. 

Congratulations!

Now you have a memorable way to introduce yourself. You are a cocktail pitch pro! The cocktail pitch formula is:

  1. Begin with your personal logline.
  2. It all started when…
  3. What you are doing now

Coming next: The project cocktail pitch!


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