Mentoring Through Setbacks

By Michael Quigley

Mentorship is about empowering and building a future generation of leaders; to do that leaders should share the reality of their careers, including examples of personal setbacks. In a recent meeting with a mentor, we used the first 10 minutes of our conversation to discuss my mentor’s life story. He is clearly a top-tier officer with a phenomenal career, but he overcame many challenges. 

He enlisted in the Army because he didn’t think he could complete college. When he was enlisted, his platoon leader submitted an application to West Point by convincing him that he was filling out a request for information – not an application. He had many difficulties as a young officer and openly admitted he is far from perfect. Mentors saw his potential and developed him.

My mentor shared other leadership philosophies, career advice, and valuable perspectives. But the most important thing he shared that day was openness and honesty. He talked about his own failures and the importance of sharing mistakes. Finally, he encouraged me to always share my failures and to ensure my subordinates are never afraid to share their shortcomings.

A mentee only sees you as you are in the current moment: a leader in a position of authority. Without honesty and candor, it could be easy for your protege to view your position as the result of your possession of an intrinsic characteristic they lack.

If mentees only know of their mentor’s successes, the mentee may feel uncomfortable sharing their own failures. If a protege asks for a letter of recommendation and is not selected, you would not want them to be afraid to ask you for another letter down the line – you wrote them the letter due to their potential, after all. But without sharing failures, your mentee may be less likely to seek letters of recommendation in the future or not reach out for mentorship touchpoints due to a fear of having let you down.

Leaders must also weigh the importance of maintaining their professionalism and leadership presence. While discussing career setbacks or mistakes, a mentor cannot undermine their own standing. Choose carefully what to share and how, so as to not present as though you blindly fumbled into your current leadership position. It can be useful to focus on the lessons learned through setbacks to highlight the importance of personal growth as a leader. 

Applying for an opportunity in the military can be daunting. You must compile career documents, build an application, and almost always submit letters of recommendation. Throughout this process you will inevitably tell friends, peers, and mentors about your desire to serve the military in a new way.

But not enough leaders talk openly about what happens when you are not selected. There is an initial grieving for what could have been, the eventual acceptance, and reorganizing to plan your next career move. There is also the uncomfortable reality that those friends, peers, and mentors will ask about your application.

In my career thus far, I have applied for two separate and incredibly selective programs and was not selected for either. From personal experience, it can be difficult interacting with the mentors who provided letters of recommendation while also processing a non-selection. But with the mentor who shared his failures, it is now thankfully different. I would be comfortable calling him to tell him I was not selected, because I know he would know how I feel at that moment. More than someone who projects a perfect image, he could sympathize and provide both sound counsel and guidance for a way forward.

Mentorship is more than discussing career paths, reviewing Soldier Record Briefs, and writing letters of recommendation. Before writing a letter of recommendation for anyone, leaders should share a story of a time they failed or did not get the job they wanted. When you identify a Soldier worthy of investment, share some of the setbacks you experienced in your career so they will know success is still possible after disappointment. Through this one simple action, whether your mentee succeeds or fails, they will remain comfortable with you and you can continue to develop them to their full potential.

Michael Quigley is an active duty Army Military Intelligence officer stationed at Fort Belvoir, Virginia. He spent 5 years in the 1^st Cavalry Division at Fort Hood and is currently the HHC Commander of U.S. Army Intelligence and Security Command.