“What 3 things am I going to wish someone had told me?”

Guest Post by Gina Herald

I never thought about it at the time and it was very early in my career.  I had been promoted and I was on-boarding my replacement.  As I was showing her the ropes and giving her the tools and information that were essential to her success, I turned to her and said, “And here are 3 things I wish someone had told me when I was getting started in this role.”  They were things I had learned along the way that had I known them sooner would have shortened the learning curve for me. They also contributed to my success in the role and I love to help others succeed so why not share the “secret(s) to success” if I have that key information.

Since that time and throughout my traditional business career whenever I had taken on a new role, I have asked the person that held the role previously

“What 3 things am I going to wish someone had told me?”

It never fails that I get a “Wow! That’s a great question.” Usually unprepared for it they need some time to consider what those 3 things might be.  I have found that I can uncover some real informational gems by asking that question.

I think sometimes if we’ve done something for a long time or held a certain position for a while, we don’t think about some of the things we just do as a result of lessons learned along the way, so we don’t instinctively share that information. I love that it challenges people to consider thoughtfully before they answer.

When I became an entrepreneur, I found that question to be invaluable in uncovering critical information that would help me serve my consulting clients better and I continued to make it part of my initial questioning strategy.

I’ve also used it when I am taking on a role on a volunteer board or as a leader in a volunteer organization.

For me it’s been a great way to get started on any information gathering journey. And of course, I still share the 3 things I wish someone had told me when I find myself in situations where passing that along is a huge benefit to someone else.

I had the occasion to ask a version of my favorite question just yesterday. We are at the beginning of a potentially sticky project and some of my colleagues have had initial leadership meetings prior to our team having ours.  I took that opportunity to ask them “What 3 things might I be missing as I prepare us for our initial leadership meeting?” Of course, I have the benefit of their hindsight and I’m taking full advantage of it so I can improve the information at our leadership team meetings.

I had no idea at the time that I turned that statement into a question, how often I would use it moving forward. If you haven’t used this question before I invite you to give it a try and see what you get in terms of a response.