Preparing for a Pitching Event

I’m not talking about a stand-up presentation in front of an individual investor or VC firm but rather some form of on-stage pitching event. It might be called a “demo day” or “shark tank” and might also come with awards (including cash). Too often, I see entrepreneurs make basic mistakes that could have easily been avoided if they had prepared, even just a little.

I actually think it’s a common personality trait of many entrepreneurs. They take pride in being able to “wing it”. But if the stakes are high, why impose the extra risk? In this article I cover a checklist of simple preparation tasks and best practices for pitching events.

Introduction

This article assumes you’ve already decided to participate in a pitching event (aka – “demo day”). If you are still undergoing that consideration, read my article titled “Why Participate in a Pitching Event?” and then come back.

If you’re the type that prefers to watch a video rather than read an article, I have all of the information below, and even more, in the free streaming video shown below.

To Memorize or Not?

That’s actually a personal decision. I always recommend that, at a minimum, the opening statement, closing statement and select key message points in between are memorized. And if the pitching event has a strict time limit, I push even further for memorization.

Actually, it is fairly easy to stay within the allotted time for a 90 second and somewhat easy for a 3 minute pitch. But anything longer is really hard to get right without memorization. Finish 30 seconds early and you missed a valuable opportunity. Go over the time limit and you might get the buzzer at an awkward time and before being able to recite your important and hopefully memorable closing statement.

Regardless of how much of your pitch you decide to memorize, I recommend a technique I refer to as “trigger words”. The images and text on your slides can obviously help you but you don’t want to always have to turn your head and look at the slides just to remember what you want to say. Instead, think of a key word that is in the first sentence of your narrative for that slide. It is usually a verb or strong noun that somehow stands out as key.

Type out any memorized sections of your pitch and highlight these trigger words in some color so that as you are practicing and needing to look at the piece of paper, the trigger words easily jump off the page and eventually sink into your brain. You’ll be amazed at how often you’ll try to recite the narrative without looking at the paper and the image you see is the trigger word with the colored highlight. You might have done something similar when studying for a college exam using your written lecture notes.

Supported Presentation Formats

This information is probably in the information package provided by the event organizer. If not, ask as early as possible. Here are a few things to look for and incorporate into your plans:

File format – Which are allowed? (PowerPoint, Keynote, PDF, etc)
- If PowerPoint or Keynote is allowed, don’t use a non-standard font but rather go with one of the very common ones that are natively supported by these programs. Your presentation is going to get loaded onto someone else’s machine and if they don’t have the font you used, crazy things can happen on-screen and you won’t catch it until you’re on stage and staring at an audience of 100 people.
Animation – If only PDF is allowed, any animation you configured into your PowerPoint or Keynote presentation will be lost. Instead, create successive slides, each with an incremental change. That way, as you advance through the slides it gives the appearance of the most basic forms of animation. Of course, motion can’t be recreated but appear/disappear/move/accentuate forms of animation are easy to replicate with this trick.
Audio/Video – If you want to incorporate these forms of media into your presentation, you should first understand that you are taking on additional risk. So it needs to be worth the risk to include. What I mean by “risk” is that, from my experience, 40% of the time some glitch happens while on stage. Second, you’ll need to make sure the A/V setup for the pitch event will support the audio stream. And finally, if only PDF file formats are allowed, this won’t work.
Font Size – This has less to do with supported formats and more to do with readability from the middle and back of the conference room. When in doubt, go larger and leave plenty of white space on the slides. Test it yourself by standing 8 feet away from your laptop while navigating through your presentation. Can you easily read everything? Try again while standing 20+ feet away from a 42″ monitor.

Practice, Practice, Practice

I know, you hated it when your parents said “practice makes perfect” but you’re going to hear it again from me. Whether you choose to memorize your pitch or not, you want to practice numerous times before the actual event. And if you decide to memorize, you should practice 50+ times (literally) – basically until you’re automatically reciting your pitch in your dreams, then practice a dozen more times. The other reason to practice is to get the timing down to fit within the allotted slot (3 min, 5 min, etc).

One important thing about practice is not to just barely go through the motions but rather to practice as often as possible as if you are actually on stage (pace, excitement, hand gestures, etc). “Muscle memory” suggests that if you practice casually, that’s what will inherently occur for the real pitch.

You can’t do this while walking through the grocery story or filling your car with gas but you definitely can at home, in a conference room and in front of your teammates. In fact, make sure to practice in front of an audience (even small ones) as often as possible because 1) that’s closer to what you’ll experience during the real event 2) they can give you feedback about content, delivery and style.

Prepare for Questions

If your pitching event calls for a Q&A session immediately after your pitch, prepare for the questions you might get. If you’ve been in fundraising mode and have been meeting with investors, you are likely to have heard 95% of all possible questions and the most common ones over and over. But for investor meetings, you have plenty of time to answer questions and that’s not the case while on stage when only 2-3 minutes are often allocated for this.

Your answers should be both compelling, clear and concise (10-20 seconds is ideal and definitely not longer than 30 seconds). Write down a list of the 10-20 common questions you could expect and make notes on a compelling, clear and concise answer for each. Below are some puff-ball questions you definitely should be prepared for (if not sufficiently covered in your pitch deck). They’re written for a pre-launch startup, so you’ll want to adjust here and there if you’re already generating revenue.

Why did you decide to do this? (solve this particular problem)
How many prospective users/customers did you talk to and what did your learn?
What evidence do you have that people will pay money for your solution over other alternatives?
How will you acquire customers?
How will you make money?
What level of sales success will be needed to reach $10M in annual revenue? How about $100M?
Does your solution, or approach, have something that can be patented? (especially for deep tech startups)
How does your solution work?
What is your initial target market and why?

Judging & Judges

If your event calls for judges or panelists that will ask questions, there are three key things to research ahead of time:

What criteria will the judges use to decide on the award(s)? Use this to influence the content, flow and delivery of your pitch.
What is the background of the judges/panelists? Find their biography (their LinkedIn profile is usually fine) to determine how much they might know about your product or business model and to predict what questions they might ask.
You don’t have to have a great or complete answer for every question. I would rather hear “We haven’t gotten far enough to spend much time on that but my gut feeling is _____” than some made up, on-the-fly answer that has no basis and comes across disingenuous.

The Day of the Event

By this time you’re well rehearsed and ready for any curve ball questions the judges can possibly throw at you but there’s still more you can do to have the best pitch possible:

Get into the conference room or ballroom as early as allowed to see the size, shape and audience layout.
Stand on stage as early as allowed to determine exactly where you will stand and what the atmosphere looks like from there.
- Where is the presentation screen(s) the audience will look at?
- Is there a smaller monitor in front of the stage that you will be able to look at as a reference during your presentation? (instead of having to turn your head/body to look at the big screen)
- Where will the judges/panelists be sitting and how should you be oriented when taking their questions?
- If possible, go ahead and practice some/all of your pitch during this exercise because it will cause the real pitch to seem “familiar” rather than “virgin”.
Ask the coordinator of the event to show you the remote clicker you will use to advance the slides. Hold it in your hand and click the forward and backward buttons. Notice if there are any other buttons on the clicker, especially ones you do not want to hit (for example, some clickers have a button that escapes out of the slide show).
Find out if you’ll be using a wireless mic attached to your shirt or using a handheld one. If a handheld, hold the microphone in your hand to see how it feels.
If you have embedded audio or video in your presentation, beg the organizer to give it a test using the actual A/V setup that is being used. You don’t want on-stage surprises.
Transfer a copy of your presentation to a memory stick and take it with you as an emergency backup. Have it in multiple formats (ie – PowerPoint and PDF or Keynote and PDF).

Bringing It All Together (example)

Here’s a good example of what it looks like when everything comes together nicely. The video below is of Loop & Tie founder Sara Rodell, as she gives an award-winning pitch at the 2017 Salesforce Dreampitch event. Notice her focus on the problem, the value her solution delivers, and a couple of real-life customer stories. Also notice how her use of imagery and limited text on the slides causes you to listen to her. Notice how her smile, body movement and general demeanor conveys confidence.

If you’re about to be the host of a pitching event, check out this article explaining how to run a demo day pitch event.

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