How to Ask Questions Like Captain Kirk

I’ve always been a big fan of Captain Kirk.  One of the things that amazes me most is his brilliant questions.  He always seems to ask just the right thing at just the right time.

Why does God need a starship?

The right question at the right time is incredibly powerful.  It is like a superpower!  Imagine what it could do for you in sales with your customer, in management with your employees, in parenting with your kids, or in a relationship with your spouse. 

Long ago, I set out to learn to ask questions like Kirk.  I read books.  I watched him in Star Trek.  I studied Socrates.  I tried to focus.  Think, think.  What would Kirk ask?!  What do I say?  A critical moment would come up and I would just freeze like a deer in headlights.  Nothing. 

After years of trying?  Nothing at all.  No change in my behavior or skill level.  I finally just gave up.  I guess I’m just not brilliant like Captain Kirk.  Ha, if I only had a team of great Hollywood script writers working for me!  Maybe this isn’t something you can do in real life.


Last year we made and released a Pirate board game.  Fun!  After playing it for several months I started noticing some changes in my behavior.  Subtle at first, but then a massive shift.  Kirk like questions were effortlessly flowing out of me in rapid succession.  In just about all areas of my life: 

Our tire is looking a little low on the car.  Why?  Is it really low?  What is the pressure?  Is it safe to drive on?  How far to the nearest tire shop?  Can we make it?  How old is this tire?  How much tread is left?  How worn are the other tires?  Should we replace them all or just 2?  Can the others wait until fall? 

Wow.  I was finally doing it!  Asking questions like Kirk, but how?  Why?  I wasn’t even trying to.  I gave up years ago.  I had mostly forgotten about it.

Then it occurred to me.  It was the Pirate game.  What?  Really?  Yes!  The Pirate game turned me into Captain Kirk.  This is a profound lesson on learning and training.  I now realize that I had it all wrong.  I was doing it backwards.  This was my thinking:

Here I was at the bottom.  My goal?  To be like Kirk.  At least be more like him when it comes to asking questions.  Ok so how do I get there?  Well, I have to focus on and figure out how to ask questions better right?  Makes sense. 

WRONG!!!!   That doesn’t work.  I tried in vain for years with zero results.  That’s backwards.  To achieve this breakthrough, you have to do the opposite.  Here’s what the process actually looks like:

The goal isn’t to be like Kirk.  Asking great questions is the goal.  Actually it’s more like the natural result:  where you end up.  Ok, so how do you get there?  You BE Kirk.  Captain a ship for about 10 years. 

Kirk doesn’t ask great and timely questions because he is naturally brilliant at asking questions.  He didn’t learn it by going to school, reading books or practicing questions.  His questioning skills are what resulted from his career.  Serving as a Captain makes you that way.  It rewires your brain to think like that.  Captain a ship for 10 years.  Lead it through 10 battles at sea and you’ll start to think and behave like a Captain too.  Just like Kirk. 

Gee, that’s great but I don’t have 10 years to spend captaining ships in battles at sea.  How could anybody ever do that?  By playing Pirates! 

Yep, as silly as that sounds, it’s true.  That is one of the amazing powers of playing games.  They can give you real life experience;  but not just any game.  It has to be a good game that is designed and set up to teach you the right lessons. 

Most games are really just puzzles.  What exactly are they teaching you?  How to get through the next level faster? Most of them teach you how to be a good little worker bee.  Pirates! the Devil & the Deep, teaches you to be a leader.  It puts you in the role of captaining a ship.  You are responsible for that ship and all aboard.  You have to assess damage and assign your crew accordingly.  You have to get inside the head of the enemy.  Where will they go next?  How can you out maneuver them?  Learning to play this game, teaches you to analyze and think in terms of questions.  It teaches you to anticipate and plan for the future. It rewires your brain to think like a captain.

A good game can teach us in the natural way. The way our brains are designed to learn best:  through experience.  They can do it much quicker too!  It won’t take 10 years.  You can fight 10 Pirate battles in about 5-8 hours, if you wanted. 

I wouldn’t recommend doing it all at once like that.  I fought 1 battle per week.  Each game took 30-60 minutes.  In between battles, I spent lots of time in self reflection.  Why did the game end up like that?  Where did I go wrong?  What did I do right?  What should I try in the next game to be better?

After about 10 games, you’ll start to change too.  You’ll start to think like a real Captain.  Why?  Because you’ll have experience as a captain. 

Just like Kirk. 

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