When and how to jump into change or new skills

When is the right time for something bracing and uncomfortable, but something we want to accomplish or do?  Do you wade in, or run in with wild abandon, screaming all the way?

I’ve often felt like this as a leader- is there ever a right time to take on change?  We know it will be uncomfortable.  Most of the time, your team isn’t already joyfully frolicking in the new initiative and pulling you along with them. 

It’s often the leader who has to go first, or who has to lead the charge of the team running into the water together and coaxing the timid and the curmudgeonly into the water. And hopefully the discomfort will be worth it.

Here are some ways I use to assess if the time is right for taking the plunge on something new, scary, or leading your team through it. And if it isn’t the right time but I have to do it anyway, how can you make it more feasible?