When making business proposals, it’s common practice to explain the purpose — the “why” — of doing something.  Makes sense that there should be a clear rationale for doing something different than what’s been done.

As a rational person, I tend to ask “why?” whenever one of my team members proposes an idea.  “What will it solve?  What will it get us?”  That can lead to subsequent questions like, “Are there other ways to get the same result?  Why this option versus others?”

It’s very easy to get really comfortable with asking “why?” because the burden of proof is on the other person.  And you don’t need to actually do anything if you remain unconvinced.  Pretty cushy.

I recently learned about the power of asking “why not?” from an ex-manager of mine.  Whenever we would be pitched the same proposal, my instinct would be to ask, “why?” and his would default to, “why not?”  This caused a decent amount of frustration, because — although these questions are two sides of the same coin — they imply deep philosophical differences.

• “Why?” makes the status quo the ‘bar’ that must be cleared (usually by a significant margin) in order for the proposal to be worth doing.
• “Why not?” makes the proposal the ‘bar’ that the status quo needs to clear.  It assumes that the status quo is one of several compelling options.

Here is a simple, classic proposal:  “Let’s get married.”

• Why?  “There are cost savings through combining our resources.  And you can get a green card.  And people will stop pestering us about when we’re getting married.” → These are pretty compelling reasons to get married — clear benefits, not much risk.
• Why not?  “Because I like our life now.  There isn’t any financial or legal burden.  It’s simpler than it would be if we were married.” → These are generally not very convincing reasons to remain single!  

Here’s another, more contentious suggestion:  “Let’s kill performance reviews.”

• Why?  “Because we will save time and unnecessary angst among our employees.” → I’m biased, but this is not a compelling reason to make a change.
• Why not?  “Because at least a few people are getting something out of them.  They make it easier to tie performance to compensation.” → Again, I’m biased, but this description of the status quo is more compelling than the proposal.

While the decision may ultimately be the same, asking “why?” is a more conservative, risk-averse approach, whereas “why not?” takes more chances with different possible outcomes.  

My gut is still wired to ask, “why”, but I now make it a practice to shift my mindset to follow up with, “why not?” to make sure I’m not presupposing that what we have today is the best alternative.  It’s a useful trick to make sure you don’t overweight standing still.