The Art Of The Pitch

I’m fortunate in my day-to-day. I have the privilege of hearing new and exciting ideas, both by seasoned and budding entrepreneurs. I remind myself that not too many moons ago, I was in their shoes pitching for money, product and development support and, at times, attention.

Being that much of my job is hearing, seeing and experiencing pitches, it seems appropriate that I share tactics I’ve employed, as well as advice that will help in future pitches.

The context and formality of pitching is the backbone to success. It’s important to have a fresh and creative approach to meetings in order to get your audience’s attention. With money coming cheap these days, everyone and (literally) their mother is building an app. While there’s a huge amount of opportunity, it’s a busy space, so differentiation is critical.

I’m not proposing showing up dressed as a computer or doing something that’s immediately going to create an uncomfortable situation. I am proposing being yourself and adding subtle flare.

Some of the best examples of this are using ice breakers to lighten the mood, such as, “What’s shaking” versus “Hi, I’m Ben.” Create small talk that’s relevant to your audience. For example, Google the person/people you’re meeting with and talk about something you have in common outside of work, like roller coasters. Suggest meeting for frozen yogurt instead of drinks. And my favorite: Do a walking meeting instead of sitting in a board room or coffee shop. These little tweaks will vastly impact your audience’s perception of you.

Most importantly, show some vulnerability. It’s okay to be nervous. Vulnerability is actually something that everyone can relate to. It’s easier to make a deeper connection with the your audience when you aren’t sure of a specific technical, business or marketing question. The best way to break down egos is to accept the fact that you don’t have all the answers.

Tactical ways to address questions you aren’t comfortable answering are, “That’s a great question, give me a day or so to do some research and I’ll report back,” or, “I haven’t approached my research from that perspective, I’ll be sure to it — great suggestion.” Staying positive and not getting on the defensive will always lead to a more natural and approachable cadence to your pitch.

Pitching is like dating…if you try too hard, you’re going home empty-handed.

People you are pitching will generally be tight on time. It’s important that you’re prepared to hit the ground running. If you’re comfortable having the pitch be more conversational, do that, but know the context of the situation. Don’t assume you have more than 30 minutes. If the pitch is going well and your audience is engaged, there will be a natural ebb and flow and the meeting will wrap organically. Be sure to look for cues. If your audience is drifting, not making eye contact or looking at their watch, consider wrapping the pitch and send a thank you email with suggested next steps.

Material is where pitching gets interesting. Decks with lots of words are about as fun and interesting as watching paint dry — I’m serious. If you must use a deck, the best decks are ones that are single-pictured with no more than one word on them, a springboard to get the conversation going. You must know your material. Rehearsal is a large part of the magic of a great pitch. Nothing comes easy, and practice really does help.

While knowing your material is critical, it’s also important that you understand your audience. Are you pitching an associate who will have to summarize your pitch to a potential partner? Are you pitching to a product or engineer hire who needs the larger vision? Are you pitching to a potential journalist who needs the absolute nuggets to write a great article? While the foundation of the pitch is the same, the storyline changes drastically based on the who and the situation.

Pitching is like dating. Being confident is key, but it also is your Achilles’ heel. You have to differentiate, but if you try too hard, you’re going home empty-handed. Know your dance, practice. Like most things in life, good things come with persistence. Never give up.