Don't shoot your audience with bullet points

Years ago in Dallas, I decided to do a startup. Coincidentally, it was on cloud computing (it didn't have the buzz it does today). I quit my stable job, and with my co-founder, started knocking on doors to raise money for our fledging venture. We were directed to "go west", so we cashed in our frequent flier miles to meet with an Angel Investor in the Bay Area. It was like getting an audience with the Pope. We met for breakfast.

After the polite hellos, he got straight to the point: "What's your story?" I started babbling about a "Services Gateway" and other esoteric terms related to cloud computing. He stopped me and said, "What's your insight?" Take 2. I then got into how much experience I had, my co-founder's background, our professional accomplishments  (we were proud of our patents, books authored, and so on.). He stopped us again and said something like "my admin has more experience than you guys. So what?  What's your insight?"

It was a rude shock. Things went rapidly downhill in  just five minutes after our initial hello. At this point, I was planning my exit  strategy – how to walk out gracefully. But I must have evoked some empathy because he knew we were struggling and had taken a flight from DFW just to see him. So he offered for us a chance to meet with his brother down in LA. He said, "You guys have something, but I don't understand it. Maybe he can help". We changed our travel plans to meet his brother near Long Beach.

The story with his brother was disastrously similar; except, the brother was willing to spend more time with us. Midway through our spiel, he said words that I'll never forget. "You are describing a four legged animal in a forest. Until you describe the trunk, I don't know that you are talking about an elephant. I'll then decide if I am interested in the elephant or if I should run away".

So what did I learnt from that? 

• Plan - Anticipate the Audience. Give Insights, and avoid "History Lessons". No one cares about your background, your team, what you do unless it relates to the specific topic. Even so, that comes later. 
• Prepare – To Tell your Story. I would add, prepare to do it anytime, anywhere. NO SLIDES! This is your elevator pitch; at the end of the day, it's the essence of your message. 
• Present – "the Trunk" up front. Get the essence out quickly so that the audience can give you permission to
  proceed (meaning they are tuned in. Not tuned out, even if they are politely nodding).

Plan
Most presentations (and projects!) fail because of failure to plan. Have you experienced the following five “cardinal sins of presenting”?  Source: Presenting to Win by Jerry Weissman. I have committed all of them – now
I know better.

• No clear point 
• No audience benefit 
• No clear flow 
• Too detailed 
• Too long

How do you avoid these pitfalls? Here are some tips from Jerry’ book.

• Get the audience from Point A to Point B. Point A is the general state of the audience. Most likely, people are indifferent but willing to give you a chance. If you are lucky, they are interested and will stay that way. If you are unlucky, they are indignant (hostile). Anticipating the state of the audience allows you to mentally plan for what you want to say. What are the (rude) questions likely to come up? What are the obvious questions for which you need to have answers (even if it is "I don't know, haven't figured that out yet". I use this exercise to generate a list – let's call it List A. Point B is where you want the audience to go. Where do you want to take them and what should they do when they get there? Again, I use this exercise to generate a second list - List B. I keep these lists in mind when planning my presentations; and later on, to checkpoint when I am done. 

• What's in it for you (aka WIFFY… pronounced "whiffy"). This is the audience benefit taken from their point of view; their motivation to get to point B.
• Plan Analog. I find that many people start off trying to write out their presentations in PowerPoint. Much as I love PowerPoint, it's the wrong thing to do at this stage. This is the time to let your creative juices flowing; to think about your Lists A and B, and start writing down all the ideas you can as fast as they pop into your head. You can use a whiteboard, notepad, sticky notes or whatever works. Sometimes the topic is
  important enough that you want to get collective ideas with your team. 
• Structure ideas. It is said that orators like Cicero used to speak for hours on end with great lucidity. Cicero used Roman Columns in the buildings to associate with his key points. Each column was a mental trigger and represented an important idea he wanted to communicate. Reviewing your lists A  and B, now is the time to get key ideas together into "Roman Columns". It is like creating affinity diagrams. 
• Organize ideas into common flows. From childhood, we tend to associate with common patterns – linear, cyclical etc. Use these to your advantage to your organize your ideas; your audience will be able to follow along. Some helpful patterns - composite (parts of whole, e.g. when presenting elements of a strategy), funnel (boiling ideas down to insights and recommendations) and extensions (building on an existing idea to a new opportunity).

Next, I'll cover Preparation and Presentation.

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