During my last session with my business coach and mentor, Wes, he gave me the assignment to list ten leadership mistakes I’ve made during the previous ten years and the lessons learned from each. Of course, my first thought was that my biggest mistake was hiring a business coach who would give me such a painful assignment!!

All jokes aside, it was an incredibly valuable exercise. And, it didn’t take long for four to jump to the surface. A few more came to mind over the next day, and before I knew it, the list was complete in plenty of time for our next meeting. Not sure whether it’s good or bad that it came together that quickly!

After writing, categorizing, and going through the list with Wes, there were a few insights that rose to the surface:

1. Almost all of the mistakes were in the PEOPLE realm. Whether it be a hire, shift in responsibilities, premature promotion to a leadership role, waiting too long to hire for a key role, or wishing we’d fought harder to keep someone, seven out of the ten were in the realm of people or staffing. Such a poignant reminder of Jim Collins’ concept, “First Who, Then What—get the right people on the bus.”

2. About 3/4 of the list was something I did, and the 1/4 was something I didn’t do and wished I’d done (or done sooner.) In other words, some of the mistakes resulted from an action, and some were because of inaction.

3. Of the overlap of #1 (people realm) and #2 (active decisions), two of the mistakes were HOW I carried out the decisions. Looking back at the decision, it may have been the right one, but I didn’t carry it out in a way that was most honoring to the person on the other side of the decision. It may have been the right WHAT, but it wasn’t the right HOW.

Though momentarily painful, this exercise was immensely impactful. To look back and remember as a means of sharpening present and future decisions. It’s a great reminder that the PEOPLE decisions matter, that we as leaders are responsible for decisions we MAKE and DON’T MAKE, and that HOW we carry out decisions is as important as the decisions in and of themselves.

How about you? What’s one mistake you’ve made as a leader that is helpful to capture and consider as you make decisions today and tomorrow?

Cheers to acknowledging our imperfection and growing into the future!

Josh Block

Josh Block

Josh Block is a Michigan native, husband, father of two, speaker, company president, and leadership advocate. He believes that healthy leaders, thriving teams and fulfilling work carry remarkable power to transform people and families.

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