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Better Questions to Ask Instead of “Why?”

  • 5 min read

Remember how as a kid, people told you what you could or couldn’t do and you didn’t like it?

So everyone time someone told you to not do something, you asked them: “But why?’’

9 out of 10 times, you received a very unsatisfying answer like ‘’Because I say so.’  Later as an adult, this may have gotten replaced by the familiar, but cringe-worthy  ‘’It’s just how things are done around here.’’

So for that reason, most people have simply stopped using that question.  And accepted that sometimes you just have to obey people who don’t seem to know things any better than you.  That’s too bad, because that ‘’Why?’’ was in nature, a very good question to ask. There’s no point in following rules without first figuring out whether they’re senseless or sensible.  Your inner child was right, as it often is. Because skipping this process can easily turn you into a nazi or a robot.

The problem with asking ‘’Why?’’ is that while the question is justified, it doesn’t get you the results you need.


Bouncy Castles for Adults

Half a year ago, I was waiting to go sky diving. Next to the pick nick table we were sitting on, there was a bouncy castle.  So I did what every self-respecting adult would do.  I decide to go bounce on it.  I tried to but I got called off, and the following conversation ran on repeat for a couple of minutes:

Owner: ‘’You can’t do that. It’s not for adults.’’
Me: ‘’Why?’’
Owner: “Because it’s only for children.’’
Me: ‘’Why?’’
Owner: ‘’Because it’s not for adults.’’
Me: ‘’Why?’’
Owner: “Because it’s only for children.’’

After repeating that conversation about 5 times, I tried to argue with her that there were no children waiting to go sky diving (ever). And that 1 adult still weighed less than 10 children. But I could not break through this loop.  I figured I must’ve been talking to an android who could only follow her robotic programming without thinking or giving any real meaningful answers.  A bit like bureaucrats.

It was weird because if she had just explained why it’s not okay for an adult to bounce on a bouncy castle, I would’ve understood and stopped bothering her. Or perhaps my question could’ve made her realize that was perfectly okay as long as you’re not too wild.  And it would’ve made her life easier. Either outcome would’ve been better for the both of us

So why then, did our conversation lead to neither of those outcomes?


Why “Why” Doesn’t Work

Just like her answers had no substance, you could argue that my question had no substance either. And that’s the problem.  “Why” is not a very well-aimed question, it’s an open question that annoys the hell out of people.  It they haven’t questioned the rules themselves yet, it requires a lot of work from them to answer.  And on a subconscious level, people often take it personally.

When you reply to someone’s command or explanation with ’’Why?’’, it opens up a whole nasty can of ego-worms in the back of their head.

• Wait a minute? Are they questioning my authority? I need to stand firm and not let them undermine me.

• Are they saying my rules are stupid?  Don’t they trust my decision-making?  Are they calling me unreliable and untrustworthy?

• I don’t have time for this. Why can’t they just accept some things as true. God damn youngsters, always questioning everything. It’s those iPhones, and that Goth music, and those girls with the short skirts. Everything used to be better. They oughtta make gun laws less strict and all the other ones more strict. That’ll bring back peace and restore order around here.

They may not perceive these thoughts consciously in their own mind, but the thoughts are still happening. So unless your dealing with someone who is self-aware and patient, the why question will not get you any results.


Alternatives That Are More Effective

A way to get out of this conversational loop and get the answers you’re looking for is by asking more defined  questions. Questions that either probe for information, or lead the other person to a realization.


Example 1:  When someone tells you that something is:

• A necessity

• Required

• Something you must do, have to do or should do

You can reply with a direct question like:

“What would happen if you didn’t?”

This gets you both on the same team, figuring out the consequences together.  Perhaps the first few answers will still be avoiding real conversation. But you can solve this by continuing along that line with a similar question (”And then?”).  Until you get to the final consequence and can decide whether it’s really an important rule to follow or not.

What’s the end destination of not doing it?  Will you die?  Will someone else die?  Will little baby puppies get raped and impregnated by machines? Will their corpses be torn into pieces and eaten?  (Don’t worry, happens to cows all the time.)

Or is the worst thing that can happen simply that you have some fun on this bouncy castle and it doesn’t break because you took your shoes off 😉


Example 2:  Someone tells you that you can’t do something, or that it is impossible.

You can reply with things like:

• ”What’s stopping you or me from doing it?”

• ”What would happen if we did it anyway?”

• ”Are you sure?” (Are you… HIV positive?)

Then afterwards, when you’ve heard the whole reasoning behind it, you can ask them the most important question of all:

”How do you know? Have you actually tried it?”

These are all examples of probing questions that lead to more satisfying answers than a simple ”Why?’’ would.  You can use them to get answers from other people or to fight the mighty guards of the bouncy castle. But what’s even more awesome, is that you can use them on yourself to debunk all your own excuses and self-sabotage.

Just don’t use them on bureaucrats.  Their software can not handle it 😉

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