Pitch right down the middle

8 min read

Ideas are only as good as their pitches, and pros are the masters of pitch selection to improve business proposals.

Three of the best in the business — Evan Wyk, Brant Pinvidic and Brian Cristiano — joined financial expert Winnie Sun to explain why best pitches should never feel forced.

Wyk is an entrepreneur specializing in brand development, online identity, brand partnerships and personal development.

Author of “The 3-Minute Rule,” Pinvidic is a speaker, producer, director, top-rated podcaster and Forbes contributor.

Christiano is a self-made entrepreneur, growth strategist, marketing expert, keynote speaker, modern-day storyteller plus the founder and CEO of BOLD Worldwide, which specializes in strategy, marketing and analytics.

A self-styled “wealth whisperer,” Sun is a financial advice entrepreneur, speaker and media personality. She has been featured on CNBC, Fox Business, Cheddar and appeared in 100 other interviews for various outlets.

Typically, a first impression is formed in less than 30 seconds. From the second they walk into the room, expert pitchers curate the first impression they present in a positive, winning manner.

“One of my earlier managers said it’s best to be standing when waiting for someone to greet you in the lobby of an office,” Sun said. “I don’t know if this is true, but it’s become my habit. That and standing straight with a welcoming smile seem to help with that initial hello.”

Wyk warned against opportunities lost.

“You never get a second chance to make a first impression — quote, unquote,” he said. “Put your best foot forward. Your attire, body language and facial expression should ‘shout’ confidence. Show how pleased you are to be there.

“Don’t forget to be yourself,” Wyk said. “There’s no point in ‘being’ someone other than yourself. I am convinced it will hinder rather than help you.”

Pinvidic places value on silence.

“Wait before talking,” he said. “Too often people want to be the first one speaking. It’s more important to say less and say the right thing.”

Intelligence collection

Advance scouting lays the groundwork for pitches.

“Know your audience,” Cristiano said. “Who are you meeting with? What do they value? How do they want to be pitched? What pain point are they looking to solve?

“Dress and speak the part,” he said. “If you’re presenting to executives in suits, wear a suit. If you’re presenting to Burton Snowboards, ditch the suit. And always know your content. Be the expert.”

Sometimes less is more. Those in a complicated industry might want to pitch a piece with a lot of details. It’s better to simplify messages to include just core concepts.

“Generally I’d agree that less is more,” Sun said. “However, it’s important to understand who it is that you’re pitching to.

“For example, if you’re pitching to engineers or physicians, they might want more data to be comfortable with your information,” she said. “If you’re pitching creatives, the pitch may need to be more aesthetically pleasing.”

This circles back to learning about audiences beforehand.

“Less is best,” Wyk said. “When pitching, focus on your reason for pitching — your goal. Add some stats — data — with which you set up your moment to ‘draw them in’ — not sell them something. Then tie the knot.”

He emphasized pitches are conversations. Pitchers should not be robots.

“You must approach it from the buyer’s perspective,” Cristiano said. “What problem do they have? Then focus only on the areas of your pitch that solve that problem. The rest is unnecessary. Ask yourself, ‘What problem do they have that I solve?’”

Practice makes perfect. Run through pitches in front of the mirror or friends. This helps pitchers explain their business or proposal in a quick, clear, concise, comfortable manner.

“If you’re not used to pitching yourself or your business, practice over and over again until you’re happy with your presentation,” Sun said. “I find videotaping myself most effective, especially since I can’t stand looking at or listening to myself.

“Practice forces me to fix or correct quicker,” she said. “It’s a great teaching tool.”

Few words speak volumes

It also shows that less is more.

“The most important thing is the focus on what needs to be said, not just what you want to say,” Pinvidic said. “When you say less, you’ll be more confident. Your audience will sense that.”

Cristiano gave what he called the most powerful process to create pitches:

  • Step 1: Film it.
  • Step 2: Watch it back.
  • Step 3: Critique it as if you’re watching a third party.
  • Step 4: Be honest. Fix what could be better.
  • Step 5: Repeat Step 1.

“Definitely rehearse — first to get your ‘script’ word perfect, thereafter to others to get a reaction,” Wyk said. “Then do a ‘script edit’ and repeat it to like-minded people. The most important part is to stay focussed on your message. Nail it all in around 60 to 120 seconds.

“Record yourself — especially if you’re a bit negative about watching or hearing yourself,” he said.

When pitching, presenters should highlight what makes them different, what problems they solve for clients and what makes them or their business unique.

“What makes me different is that I take a lot of time to prepare for each client, and then spend even more time getting to know the client,” Sun said. “Then I can truly understand what the needs are.

“Nothing is rushed,” she said. “Everyone is comfortable and heard. It sounds simple, but the true art of listening is something I’ve been practicing and improving for many years.”

Honest presentation

Be sure that storytelling is truth telling.

“Always be honest,” Wyk said. “Nothing ‘kills’ your opportunity like pretending. People in business will see right through you. Stay true to your experiences and highlight your positive outlook. Be upfront about what you will bring to their table — your value.”

Look through the eyes that matter most.

“Unlike most big consulting firms or ad agencies, we solve holistic business challenges from the perspective of an entrepreneur,” Cristiano said. “We’re like injecting rocket fuel into a company. And quickly. For everyone. Find the unique experience you deliver and highlight it.”

Stories need to capture the audience’s attention and maintain it.

“Start and end with the truth,” Sun said. “This is what I’ve always found to be most effective and relatable.

“People expect you to try to sell them something,” she said. “Of course, I could, but they would head home and have buyer’s remorse. I want them to feel this is the right decision for them. Therefore, less selling, more explaining and sharing using relatable scenarios.”

Sincerity and pride underline value.

“Speak from your heart,” Wyk said. “Show you care about your product or service. Always be proud of your brand. Showing sincerity will strike a cord on many occasions. Ultimately, ask yourself if you are being yourself in this conversation? The truth will always prevail.”

The emphasis is on the pitch, not the pitcher.

“Tell the story of the outcome you create, but from the perspective of either a similar customer or client or the customer you are pitching,” Cristiano said. “Remember, while it’s your story, it’s actually all about them — not you.”

Value grows from insight versus repetition.

“Always make sure you’re not telling the audience something they should already know,” Pinvidic said. “If your value is very obvious, you don’t need to restate it. Look for something that is actually valuable information, not just something cool to say.

“A story is told piece by piece,” he said. “You want to lead your information to your eventual conclusion. Don’t state and prove. You always want to inform and lead.”

Knowledge builds confidence

Even facing a friendly crowd, stage fright is real but can be avoided.

“My long-time business partner always says that being nervous before going onstage is good,” Sun said. “It means you still care.

“The best way to counteract fear is practice, practice, practice,” she said. “You won’t be perfect, but you’ll feel more comfortable knowing that you’re prepared. Then smile, and simply go for it.”

Wyk follows these go-to tips:

  • Smile, breathe, and speak slowly.
  • Stand tall with both feet solidly on the floor.
  • If your hands tend to flap, keep them clasped when not using to enhance a point you’re making.
  • Don’t be casual and laid-back.

“Confidence comes from the value you believe you bring your audience,” Pinvidic said. “Your stage fright will go down the more confident you are in your information. It’s not about believing in yourself. It’s about believing in the value you bring.”

Product knowledge is a great remedy for stage fright.

“Know your subject matter,” Cristiano said. “When you know your stuff, it’s easy to speak, easy to answer, and you exude confidence. Practice. Remember, it’s just a pitch. Seventy-five percent of the population is afraid to do what you’re already doing. So kudos.”

Knowing the audience includes research into particular attendees.

“I try as much as I can to do research on who I’ll potentially pitch to,” Sun said. “There is so much information online. Understanding someone’s opinion on different subject matters helps to better personalize a presentation.”

This is when to put research to best use.

“Hit the internet to find background information,” Wyk said. “You will then have a good indication of whom you’re up against and talking to. Mentioning a fact or two that you found out could quite easily count in your favor. Impress them.”

Ease off the gas

Although pitchers know their tactics, they should be subtle.

“It’s always a good idea to incorporate research, but be very careful to not be obvious about it,” Pinvidic said. “Your audience will be sensitive to trying tactics to make it more personal to them. Let your information lead.”

In a sense, successful pitchers are stalkers.

“I hunted down a prospect on social media — who was private — to find out they liked white wine,” Cristiano said. “Guess what I brought to the pitch? I found a picture of them on a friend of a friend of a friend’s Instagram. Creepy? Maybe. Effective? You betcha. Deal closed.”

Self-critiquing pitches can be done with “push-back” questions. Trying to poke holes in your pitch can improve it.

“My favorite question is, Does this really bring value to the other person?” Sun said.

“Too often, we’re pitched things that only bring value to the person who’s pitching us,” she said. “It should be less about us and more about the value we would bring to our next potential client. Always question your pitch until it speaks this language.”

Head off bad news before it pops up.

“The first question you should ask yourself is, ‘What do I hope my audience doesn’t find out?’” Pinvidic said. “You gotta deal with that before they do. They will always find out. They are looking for strings and holes. Be proactive.”

Using push-back questions also gauges audience attention.

“Push-backs are a good way to find out if your listener was indeed listening to you,” Wyk said. “Keep questions relevant to the subject: Done it like this before? Any issues caused headaches? Outcome satisfaction? Suggest solutions via key performance indicators.”

Helpful supplements

Best pitches can be accompanied by an assortment of accessories.

“A pitchbook helps keep the presentation moving along, and helps you remember the things you need to cover in greater detail,” Sun said. “Although even a carefully thought-out outline can do the same.

“Nowadays, we often just start with a blank paper and get to know the client before making any sort of presentation,” she said.

Good pitchers also leave remembrances.

“A leave-behind depends on the environment you’re pitching in,” Wyk said. “At events, a USB stick will suffice. For an office meeting, a slideshow plus a walk-and-talk, a business card or services postcard will do the trick.

“A presentation is a fairly detailed document,” he said. “A pitch deck is usually the shortened, less complicated version of your presentation. Needless to say, both need to ‘speak’ the same language and provide the same information.”

Beware of death by PowerPoint.

“If you present and you use a PowerPoint, don’t use your handouts as your slides,” Pinvidic said. “Don’t make people read while you talk. I use simple bullet points — only a few words at most.”

A neglected yet essential part of the pitch is following up.

“The follow-up to any meeting is the most important aspect of the interaction,” Sun said. “Everyone wants to feel heard, in demand and important.

“Follow up promptly to those who have opened the door to further communication,” she said. “Don’t let a warm lead turn cold. Follow up and over deliver quickly.”

Sense of urgency

Wyk emphasized rapid response.

“Throughout your meeting you should’ve picked up on the urgency of the project and your potential client’s workload,” he said. “That will give a good indication what route you should take following up after the meeting.

“In general, a 48-hour pause before an email is sent works for me,” Wyk said. “After another 24 to 48 hours of a ‘no reply,’ a quick reminder email will go off with the promise of a telephone call the next day. Be sure to keep to that promise.”

At the same time, he cautioned not to be over anxious.

“My best advice is to neither bombard the client’s inbox nor clog their voicemail service with messages,” Wyk said. “Nothing is more off putting than to come across as too eager or very desperate. Let’s face it, being annoying is not a good attribute. Avoid it.”

Information collection post-presentation is critical.

“Get cell phone numbers,” Cristiano said. “Text potential clients immediately after the presentation. Stay on top of them daily until the deal is done.”

The bottom line is not to be forgotten.

“It’s a busy world,” Pinvidic said. “Follow up helps keep you top of mind, but you can’t push for a decision. You have to let that come on it’s own.”

Jim Katzaman Jim Katzaman is a manager at Largo Financial Services. A writer by trade, he graduated from Lebanon Valley College, Pennsylvania, with a Bachelor of Arts in English. He enlisted in the Air Force and served for 25 years in public affairs – better known in the civilian world as public relations. He also earned an Associate’s Degree in Applied Science in Public Affairs. Since retiring, he has been a consultant and in the federal General Service as a public affairs specialist. He also acquired life and health insurance licenses, which resulted in his present affiliation with Largo Financial Services. In addition to expertise in financial affairs, he gathers the majority of his story content from Twitter chats. This has led him to publish about a wide range of topics such as social media, marketing, sexual harassment, workplace trends, productivity and financial management. Medium has named him a top writer in social media.

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