A Halloween Leadership Challenge

Photo courtesy of Danny Chapman via

Happy Halloween! I’m not going to lie. Halloween is my absolute favorite holiday of the year. It even beats Christmas which is too busy, too hyped, and it drags on for months and months. Here in the Midwest the weather this time of year is relatively palatable and trick or treating is a great excuse to take a nice long night stroll.

I have fond memories of trick or treating from when I was young. I’m particularly proud of how cool I thought I was when I scored a huge bag of candy and ran home to change into another costume so that I could go for a second round. It was always enchanting to mingle with the neighbors and see the neighborhood light up into a fantasy world for one magical night. I loved being someone else for a few hours!

As an adult I love watching my kids enjoying the same adventures that I did. I enjoy combing through their candy and picking out my favorite chocolates. I always tell them to bring me back all the chocolate and Twizzlers that they can. Please don’t give them apples or healthy stuff in the pumpkin bag. I don’t like to eat those on Halloween! I will also admit what so many of you are thinking – it’s fun to look into people’s homes on Halloween when they answer the door to ghouls and princesses. Come on…..

My kids have always dreamed far in advance about what they want to be on October 31st. With 4 boys the planning certainly saved last minute panic and money. Thinking ahead about who they want to be has always been an interesting experience to watch as they toss out ideas, sketch pictures accenting details, and spending countless hours researching on the internet. I’ve relished hearing why they want to be a particular character and watching them act the part. For our family, Halloween has been about using our imaginations and putting ourselves into the shoes of someone else for one magical night.

This Halloween season I have a challenge for you. Consider it a leadership growth opportunity. One day a week for the next month pretend that it is Halloween. That’s right. Now, you don’t need to dress up unless you really want to but prepared for strange looks. For just one day place yourself into the shoes of someone else that you lead or work with. Become this person as they go about their day, manage teams, fight fires, and handle difficult clients. Learn what your people really do and how they feel as they go about their day. What challenges do they face? What frustrates them? What obstacles are in their way? How is the culture that they work in? What works for them and do they seem to enjoy their role? The questions are endless as you “trick or treat” in the shoes of another for a day.

Are you ready to up your leadership for the next month by pretending to be one of your staff for a day and utilize a “trick or treat” form of leadership? I would love to hear the results.