5 Questions to Ask When You Just Can't Let It Go

“John,” the CEO of a fast-growing start-up, was visibly frustrated when I asked him what he needed me to work on with his team. “I love my team. And they care so much! They’re full of great ideas….”

I waited for the BUT.

“BUT,” Sometimes they get stuck on an idea and can’t move on. We’re moving fast and sometimes that means failing fast and letting go of ideas that didn’t work. Can you put some of that into your Winning Well bootcamp for them?”

I love it when curriculum design becomes blog post fodder.

Now the truth is, there was more to this story as I unraveled the layers… a solid dance of knowing when to hold-em, fold-em, walk away and run. We worked on both letting go AND how to P.E.R.S.U.A.D.E. your boss.

5 Questions to Ask When You Can’t Let It Go

If you’re in a position where others are encouraging you to “let it go” when your heart says “hold on,” here are few questions to help you decide.

Why am I so passionate about my idea or way of doing things?
Are you coming from a place of true confident humility, or is fear or ego getting in the way?

In one or two sentences, why am I so committed to my position?
We must do _______ because __________ and if we don’t _________, the consequences will be __________.

Who is encouraging me to let it go and why?
It’s highly likely they have additional perspective. Be sure you understand it.

What are the potential consequences to the big picture if I don’t let it go?
Take time to really understand the pros and cons.

If you were to let it go, where else could you focus your time?
Sometimes you have to lose a battle to win the war. Fighting and holding on takes time and energy. What else can you accomplish?

The truth is, sometimes the answer is to let it go–holding on too tightly to your position, can slow down results and damage your career. AND sometimes the answer is to fight for what you know is right for the business and the people within it.