Waiting for Inspiration to hit…and 5 Tips for a successful pitch


Has this ever happened to you when you had a, let’s just say, creative, assignment to fulfill with a tight deadline and you draw blanks for days leading up to the final day or so? I had a presentation to make on Wednesday before my group of 45+ people – probably half of whom I had never met before – where I was to create a CEO pitch about material that is, well, pretty boring on the surface. I struggled with this and it tortured me for days. Basically, the assignment was handed down from upstairs last Wednesday evening but I was 100% on other projects Thurs and Fri and was busy with kids over the weekend – yet another one of those birthday parties that freed up two hours for me to run about 6 errands – so no progress. Monday, I flew to Boston and Tuesday was in meetings from 7am to 10pm more or less. So there, I am late Tuesday PM with this deadline looming for Wed 10am…I worked until about 3h30 on a skeleton but never quite had an idea that really inspired me. The next morning, I was up at about 6am still hoping that the inspiration would just fall on me but honestly it was during one of the other presentations I was competing against (basically there were four teams with the same assignment fighting for a iPad 2 – thus my strong desire to win) that it hit me. I found a great analogy between my stuff which is basically a collaboration platform and the family duties of the CEO I was pitching to and how with a Wii he could fulfill everyone’s needs and so by analogy so could we. It was pretty incredible as I was applauded by the audience for that one. And yes, I did win the iPad 2.

What I found interesting about this experience is that the inspiration finally came literally minutes before I hit the stage. Is this my mind just psyching me up or do I require some overwhelming stress for the left-brain to kick into action with some creative solutions? It remains a bit mysterious. Perhaps, I should go Google about it on the new iPad 2…

But before I do, let me share a few things I learned about pitching to a CEO and that were other keys to this little success:

  • Keep it short. Guy Kawasaki recommended over on Forbes.com the 10/20/30 rule: 10 slides, 20 minutes, 30 point fonts. I think that is a brilliant summary and works wonders
  • Analogies speak louder than slides. The killer Wii analogy was what really clinched this effort. I was able to take something very complicated and hard to explain and render it simple and attractive by making the value immediate and obvious.
  • Needs before solutions. I started the presentation with the probable needs of the CEO in question and then backed up that assessment with an extract from analyst’s report – full-screen – demonstrating those same points followed by yet another (although not impartial because we paid for the study) analyst showing how my solution uniquely solved those needs. The feedback I got was very positive from the crowd.
  • Get their attention and keep it. I showed a photo from the US Women’s Beach Volleyball team when they won gold in Beijing back in 2008. Now, there was a subliminal message intended here (appealing to the unexpressed prurient interests of the male CEO) but it also did actually grab attention and get some momentum rolling as I was building out my message.
  • Know when to fold ’em. If I were to change one thing about this performance, I would have just ended on the applause after my Wii analogy. Instead, I plodded on through a few slides and my fatigue-addled brain screwed up on slide changing and I had to fiddle with PowerPoint to get some (in retrospect) lame videos to play. I think that if you hit a vein, probably best to stop there and assess whether you are done or if further explanation or details are necessary before blindly moving forward. Luckily, the impression of the Wii thing was so strong that the majority of my audience just forgot about the rest when they voted.

About mfinocchiaro

IT Architecture Guru for large PLM software company but dabbling in Web 2.0 and other stuff.
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