A little while ago I found myself on a conference panel with David Barett, founder of Expensify. There is a lot to be said and learned from David and his uber-successful company — anything from his leadership philosophy (parts of which we have discussed here already). But the thing which stuck with me was his story about Expensify’s Super Bowl ad.
If you know anything about the Super Bowl, you know it is one of the most watched sporting events in the world and one of the most expensive and prestigious advertising venues. Spots during the Super Bowl TV broadcast are sold long before the game starts, at a staggering $175,000 per second of airtime. Typically these spots are booked by fast moving consumer goods, food and car companies — who are in the business of selling products largely to average consumers in average households. 2019 was the year David decided to add his expense-reporting software to this illustrious list of companies.
As much fun it would be to talk about the TV spot and its impact on Expensify’s business — this post is about the question how David got this all started in the first place.
See — David had this crazy idea (seriously, it is a crazy idea for a company as his to have a Super Bowl ad). He brought it to his team and he did something magical: Instead of having people, such as his marketing team, debate the merits of a Super Bowl ad, weigh all the pros and cons and essentially discuss “should or should we not”, David framed the question differently:
“How are we going to make a Super Bowl ad and make it work for us?”
By simply framing the question as a “how” question, he challenged his team to come up with their best and most creative thinking (and not engage in a “if/should we” debate). Question centered around finding the money to pay for it, to the ad itself, to the way you leverage the ad in ways which make sure, that the endeavor makes financial sense.
The next time you want to challenge your team, colleagues or even your family to do something outrageously ambitious — instead of asking if/should we, go straight to the how. It still might turn out that there is no conceivable way to get it done; but at least your discussion centers around creative solutions to the problem and not a debate which ends up being a simple yes/no.