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Over the past decade, I've started, been employed by, and advised a flock of startups. More recently, I've been an advisor at events like Startup Weekend, Lean Startup Machine, and the new Longhorn Startup Program at UT.
One of the big pushes in recent years - I suspect primarily due to Lean Startup - is customer interviews. At some point during these interviews, the "would" question comes up. Generally it's structured something like this:
"Would you like a product that makes X better?"
And every group celebrates that "95% of our customers said yes!"
That's great, right? Well.. let's break this down a bit.
First of all, until they give you money, they're not a customer. That's it plain and simple.. so therefore, these are potential customers or potential users but not customers.
Next, I'm surprised that anyone said No. If you asked any random person on the street if they'd like to be a) healthier, b) happier, c) better organized, or a flock of other things, they're going to say Yes. After all, who wants to be unhealthy or less organized? There's a reason these are New Year's resolutions every single year.
Finally, the word "would" taps into a special place in people's minds. At the end of the day people are optimistic. I'm sure of it! ;) Think of the most negative person you know and ask them "would you like to be healthier?" They will say "Yes" and then come up with a bunch of reasons they're not.
There's a more subtle thing happening in here. Netflix did a study years ago where people would add high minded movies to their queue.. and skip over them to watch Dumb & Dumber. People want to think they'll make better choices but in reality, rarely do. That's one of the reasons - that despite their own previous behavior to the contrary - people choose healthier, happier, or better organized as New Year's resolutions every single year.
And that's also why gym memberships are paid annually up front.. "because this year I'll use it!"
To get around "would," I try to get at the deeper "what did you do to solve X last time?" and follow it up with "what made you chose that approach instead of A or B?" That can help you find if the choice was driven by familiarity, cost, resistance to change, ignorance, time, or a variety of other things.
So be careful around "would" and try to figure out if you're tapping into reality or their optimism.