Be Prepared

Why You Need To Be The Most Prepared Person In The Room

There is an old adage that goes, “If you’re the smartest person in the room then you’re in the wrong room.” I agree with that. You never want to be the smartest person in the room. But for a big customer meeting or investor pitch you better be the most prepared. In fact, that’s how I made my career.

My first sales job was with WhippleHill, which was acquired by Blackbaud. I sold educational software to private schools. It was the best first job you could ever have because just about everybody went to a private school or knows someone who did – it is a constant ice breaker for me. This job also taught me how to communicate with all walks of life on the buyer side, from teacher to board director to CIO.

But it was an even better training ground

Prior to a meeting with a new school, I’d learn everything I could about them. I’d print off all the pages from the school’s website, learn who their alumni were, check out how the sports teams were doing. Next I’d read articles on Yahoo News, check out the Wikipedia page for the school, read the National Association of Independent Schools (NAIS) directory page (on them and their comparators), see if I had any connections on LinkedIn. It was a lot of effort to look through so many different data sources but I always felt like it was worth it. Doing so gave me the edge and that confidence helped me as I went into the meeting. 

At the beginning of my meeting I would always share one of the factoids I’d learned, “Is Mitt Romney an active alumni?” “That was quite the gift from Bill Gates. Congrats!” “I am glad you won last week against the Kinkaid School.”

I never went over the top but just drop enough knowledge to ingratiate myself with the prospect. It also enabled me to participate in discussions in the sales process. In the end, did it make the difference between closing the deal or not? Who knows – I’d say yes – of course. But at the very least it showed the prospect that I respected them and their business enough to invest in doing my research. It gave me instant credibility and made sure they took me, who was in my mid-twenties at the time, seriously. 

I have carried this behavior with me throughout my career. It’s how I enter every business development opportunity. When I was pitching Dyn to Oracle I needed to know more about Oracle’s vision as a company than the executive at Oracle I was working with. Only by knowing where Oracle was headed could I sell them on the strategic value of how we could help get them there.

This is why I always tell entrepreneurs to be prepared. There is no clear path in entrepreneurship. Startup success is not paint by numbers. Things happen. You need to react. You need to always be in the game. The only way you can do that confidently is by being prepared. If you’ve put in the work, you’ll know how to act. People who don’t prepare will call you lucky because you’ll always seemingly come out ahead. But you’ll know the truth. 

You worked for it. You earned it. 

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