We’ve all heard the expression “If you fail to prepare, prepare to fail”. I often think about this expression through the lens of a former professional hockey player turned startup founder. In either profession, those words always ring true to me and were/are words I continue to live by, but is it possible to be over-prepared and what are some of the disadvantages to being so? In this column I chose to write about the two sides of the coin and my own experience with this topic.
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On April 9th, I had the pleasure of speaking at the Cornwall & SDG Counties Tourism Summit hosted in Cornwall, Ontario, where I had the opportunity to share our FanSaves partnership with Explore Cornwall and the SDG Counties with attendees. I had a twenty-minute speaking slot with an additional ten minutes allocated for audience questions.
I had a couple weeks’ notice that I would be speaking, so I had plenty of time to prepare my slide deck and the message I had planned to convey. In the two days leading up to the event, I spent probably a couple of hours making some minor edits to the deck and formulating some main points that I wanted to drive home to the audience.
On the morning of the event, I woke up a little early and spent about another 20 minutes flipping through the slides and another 5 minutes or so once I got to the event. Before my name was called to the stage, I was cool, calm, and collected and ended up delivering a great presentation that I really felt captured my personality, humor, and credibility on the subject.
I received great feedback from attendees and organizers throughout the rest of the event and afterwards and left feeling like I had accomplished the goal I set out to. But this result wasn’t always the case for me, and thinking back on my early days of public speaking and pitching was the inspiration for this column.
Back in 2017, my Co-Founder Shannon and I had just recently launched our new tech startup, and one of the ways we had learned that we could promote our business and potentially win cash prizes to fund our development was through pitching. If you’re not familiar with pitching or pitch competitions, they are events often hosted by a startup organization or community with the goal of giving founders and entrepreneurs an opportunity to pitch their business or ideas against other businesses, with the winners or most viable ideas receiving prizes that vary from event to event.
In 2019, we heard about this pitch competition in Ottawa being hosted by Startup Ottawa in affiliation with Startup Canada. We applied, and to our delight, were one of twenty businesses selected to pitch. At this competition, we had five minutes to pitch our business, and because it was our first one, we decided to do it together. Being a sports tech company, we had these giant blowup soccer, basketball, and baseball balloon-type props we had purchased at Walmart that we incorporated into our pitch and wore matching branded hoodies.
We spent days practicing and refining our pitch, our lines, and our delivery. On the way to the event, we practiced our lines the whole way there as well as beforehand when we got to the venue. We were informed that we would be the nineteenth company to pitch, which meant we had a little over an hour and a half, whereby I continued to practice my lines in my head while listening to all the other pitches before it was our turn.
When it was our turn to pitch, we got up on stage only to find that one of the microphones wasn’t working, which caused a couple-minute delay before we started. Shannon started with her opening few lines, and when it came to my part, I completely froze. I had spent all that time, energy, and effort practicing, and suddenly, I had forgotten it all. I mean a real deer in the headlights kind of moment, which felt like an eternity, as I looked out upon the couple hundred people in the audience, including my parents.
After what was probably about ten seconds, I heard Shannon whisper my line beside me, and it all instantly came flooding back to me, and I was able to recover and finish the pitch. I remember feeling so embarrassed as we left the stage and so disappointed in myself, but also that I had let my Co-Founder down. We ended up placing fifth, which for our first pitch wasn’t too bad.
A few weeks later, we pitched at a similar type of event, and the same kind of thing happened. At the time, I had chalked it up to getting hit in the head one too many times playing hockey, but no matter the excuse, I completely lost my confidence pitching, and from that moment forward, Shannon took over pitching solo at future events.
Over time, after watching Shannon compete at nearly two dozen events and the preparation she put into beforehand, I came to realize that my problem was that I was overpreparing and focusing on getting every word perfect rather than commanding the audience and having fun with it. No matter how many times I practiced, the words were always going to come out a little different than what I had practiced, and that was okay. No one other than myself was going to know when I mixed up a word or left out a point I had intended to make. While preparation is important, overpreparing can psych you out.
During my hockey career, no matter how physically or mentally prepared I was, I still made mistakes. The perfect hockey game has yet to be played, and it took me years to figure that out as a startup founder.
Fast forward to the present day, I’ve given dozens of major presentations and speeches to audiences from twenty people to over two thousand people. I have refined my preparation process and genuinely enjoy public speaking once again. I still believe in the old expression “If you fail to prepare, prepare to fail,” but I now have a new outlook on it, and hopefully, my experience can serve as an example of the detriment of overpreparing.
by Kris McCarthy