Why Wouldn’t Cha?

Why Wouldn’t Cha? I love the phrase “why wouldn’t cha.”  My brother introduced me to it while we were on a Daddy-Daughter weekend at Camp U-Nah-Li-Ya, a YMCA facility in the Green Bay area. ???? I have 3 daughters and missed out on too much time with my two eldest daughters during the time I was founding a technology company.  My brother took my niece and I took my youngest daughter Emily.  We had a blast.  One of the nights was skit night, where the cabin residents had to work together and perform a skit with everyone in the cabin performing.  We sat around the campfire discussing possible skits and we landed on a great idea for a skit.  My wise brother, whom I love, said, “Why wouldn’t cha?”  This was his way of saying, “Why not? Let’s go for it.” I immediately fell in love with the phrase, which I took to be a Wisconsin thing.

Anyway, we landed on a cool echo skit.  There were 4 dads and 4 young ladies in the cabin.  We had the ladies sit in chairs in the middle of the platform/stage while we dads hid behind the trees that surrounded the audience.  The girls would say something, and we’d echo what they said.  Until the last thing they said, which was something about the camp director being the smartest guy in the world and instead we echoed something that poked good-natured fun at him.  It was quite funny and everybody had a great time.

I started using the why-wouldn’t-cha phrase after doing strategic planning sessions with clients.  Sounds basic, but once you’ve gathered the facts, analyzed them, and the team has poked holes in the plan to make sure it is solid, the next statement is “why wouldn’t cha do this?”

Over the years this phrase reminded me the Tyranny of the Or, or the Genius of the AND, from Jim Collins’ perennial bestselling business book “Good to Great.”  Much like “why wouldn’t cha”, I love the genius of the AND, and I apply it all over in my life.  Few things in life are actually either/or, one or the other but not both.  There are always more options, more choices and more possibilities than we think. We just need to look for the AND.  So, I ask myself, why does it have to be an OR, when in many cases it can be an AND?

As a business leader, you have the option to:????

  • Build people AND discipline them
  • Love them AND pay them
  • Care about them AND demand better from them
  • Be a Level 5 leader AND build leaders
  • Be strong AND insecure
  • Create a strong trust culture AND fire people

Real leaders know how to grow others, to build trust, and to communicate vision.  There is so much wasted energy in creating false or negative beliefs when team members do not understand the vision of leadership.  Just be a leader that leads AND shares vision even though things can — and will — change.  You will find that your team will rally around the company when they know what you are thinking, where you taking the company, and what you expect their contribution to be.

Don’t be afraid to over share. Dave Ramsey talks about this in his book “Entreleadership,” which I highly recommend. If you over share, tell them you are doing so intentionally and move on.  Try to cut down the internal friction by letting the team know as much as you possibly can.  People do much better with facts than they do with uncertainty and doubt.

So, if you can create a strong team based on shared vision, built on trust and solid communication — and one that looks for the AND rather the Tyranny of Or — my question to you is, “why wouldn’t cha?”


  • Read “Good to Great” by Jim Collins
  • Read Dave Ramsey’s book “Entreleadership
  • Think about the AND when making decisions.  Sometimes it is an Or, but with your mind open it can be an AND
  • Remember your mind is like a parachute – it only works when it is open 🙂
  • Strive to become a Level 5 Leader

Tell me what you think. I’d love to hear from you!

Please note: I reserve the right to delete comments that are offensive or off-topic.

4 thoughts on “Why Wouldn’t Cha?

  1. Craig, great blog, and a great message for today’s business leaders. One of our biggest battles as leaders is fear. Fear of failure, fear of not measuring up. “Either-Or” options feed into this because when the going gets tough or things don’t work out like we thought, we assume we should have followed the “other” option. “And” opens up your field of vision, gives you permission to take risks, and helps you to build for the future and weather the storms that will certainly come your way.

    Good job!

    • Thanks Chris, your comments on opening up your field of vision is well stated as we have to continue to push our comfort zones to grow. Thanks again.

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