By: Lt Col Jason A. Castleberry
Race horses with jockeys on the home straight. Image courtesy of Shutterstock. (Photo contributor Lukas Gojda)
“Why bet on a losing horse?” my supervisor told me as he described why he would not support my bid for promotion. When I requested feedback on what I was doing right and what I was doing wrong, he simply stated, “You’re doing great work. There’s nothing really that you could do differently. You just don’t stand a chance at promotion.” At what point as a leader, supervisor, and mentor do you tell someone to just quit, there’s no hope for you, just give up? Mentorship, good mentorship, is a cornerstone to success. Yet despite how crucial it actually is, the Air Force does not teach leaders how to properly mentor. It is high time for the Air Force to start.
In the Air Force, we use the term “fast burners” to describe those on the “golden path.” We often look at those fast burners as having the “right stuff,” however, recent research shows that success takes more than motivation. Gorick NG recently published a book titled The Unspoken Rules, where he explains that hard work is not sufficient, “It’s a baseline.”[i] In his study, he conducted hundreds of interviews with professionals across different industries to find out being great at what you do and producing results is not enough. He notes “For every front door there’s a side door. For every spoken rule there is an unspoken rule. The key to success is learning about those side doors, those unadvertised opportunities, and those unspoken rules.”[ii] Just as these unwritten rules exist in the civilian industry, they also apply in the military.
Side Doors
Image courtesy of Shutterstock. (Photo contributor Elnur)
How many people enjoyed getting a graded paper back that you had written just to find out there is no feedback on it . . . just a grade. Or you were getting a graded exam back to see what questions you got wrong but with no indication as to the correct answer. So, what is the right answer and how do you find it? This is how many of us traverse our careers, following the known path and eventually hitting a plateau and not understanding why. Side doors are really those opportunities, jobs, projects, or specific bosses, that will get you noticed. The directions to these side doors to success are not taught in tech school or professional military education. Side doors are a targeted focus and development of people rather than the mission. It is about developing people so they can better execute the mission and eventually grow to take care of others. Without that boss, you are left at the front door looking in wondering how everyone else got there; the haves and the have-nots. This unlevel playing field enables some to advance while others just tread water. I was blessed throughout my career to have bosses who taught me how to mentor, coach, and develop those around me to build a better team. They focused on “the art” of leadership highlighting the need for emotional intelligence rather than the sole focus of metrics and numbers. This art was not taught in a classroom but through experience and the important lessons learned by taking care of people.
Feedback
Success and good mentorship all start with good quality feedback, but arguably it starts even before that with simple empathy and caring to notice how someone is individually performing and what areas they can improve on. A large part of mentorship is proper feedback that really focuses on creating positive change in your employees. However, most supervisors—in the Air Force and elsewhere—do not. We give feedback as if it were binary (good versus bad) rather than focusing feedback on how to incite a positive reaction to improve one’s performance. It is human nature to avoid conflict or topics that we find uncomfortable. While this makes us feel better in the moment, it hinders the individual development of the person in the long run and eventually improvement in the unit.
This behavior leads some supervisors to resort to poor leadership techniques to “soften the blow.” The most well-known of these techniques is the “positive, negative, positive” model, where feedback focusing on the areas needing improvement is sandwiched between 2 positive things you are doing right. This makes the ratee feel good they are doing something right and makes the supervisor feel as though they are being considerate of the ratee’s feelings. However, in the end, feedback received this way is often fruitless. The constructive comments focusing on matters that need improvement, that could lead to positive change if delivered effectively, are watered down. Start with genuine affirmations, but don’t linger and say general statements like “You’re doing great. No real complaints.” Feedback should be actionable and framed with a growth mindset to prompt positive change.
These same supervisors may also hide behind callus statements like “Feedback isn’t personal, it’s professional.” While this statement is true to a certain extent, it lacks empathy and awareness that being a good leader is very personal. Good leaders know their people, but great leaders know their stories, their families, what they are passionate about, and what motivates them. When you know your people, you know what drives them and you can use that knowledge to focus your feedback on improvement areas so they will want to improve themselves. This level of care as a supervisor focuses more on the goals of the individual with the end state being all members of the team are better individuals than when they joined the organization.
Mentorship
The Air Force and Space Force observe January as National Mentoring Month. The theme for 2025 was “Mentoring tomorrow’s leaders today” highlighting the crucial role mentorship plays in preparing and strengthening our Total Force for potential challenges in an era of Great Power Competition. (U.S. Department of Labor graphic)
Over the years, we’ve all had both good and bad bosses. In the Air Force we have even been given “official mentors” at times; often, however, these relationships bare little similarity to those mentors that we have on speed dial who we continue to go to over the years for unrelenting support. What do these sage leaders have that the others seem to lack? What makes them our “go to” people when we seek counsel?
Well, first, the best mentors do not hold back encouragement. They do not call people a “losing horse” and tell them to give up and quit, leaving their employees feeling disheartened about their abilities, past accomplishments, and potential to progress. Good leaders help others identify areas that require improvement and then support them to better themselves. In a 2014 study published in Harvard Business Review, the attitudes of employees towards feedback (positive and corrective) were measured. The authors note that 57% of respondents preferred receiving corrective feedback rather than just positive feedback. “When given properly, 92% believed “negative” feedback was effective in improving performance.”[iii] This method of mentorship lifts people up rather than puts them down, and when individuals in your organization improve themselves, your organization improves. As a leader, you must ask yourself, will my words erode trust or improve performance?
“A rising tide lifts all boats” – President John F. Kennedy
Every Airman Has a Story
Former Air Force Chief of Staff General Mark A. Welsh, III was known for his mantra, “Every Airman has a story.” Great leaders are reliable and continuously take the time to learn their Airman’s story. As a commander, I often worked late nights to make up for the time I’d spent throughout the day being with my Airmen, learning their story, mentoring, and helping them work through issues. That time with my Airmen is my most valued time as a commander. While rescheduling on occasion is understandable, you must make a conscious effort to make time for your people. No one wants their meeting bumped because “something came up.” When it becomes habitual, you become toxic to your organization and the progression of your people. When I was a 1st Lt, I had a boss who would stop me to ask a question and then almost every time, he would pull out his Blackberry in the middle of our conversation and start answering emails like he could not be bothered with our discussion. It was clear he did not care and that I was at the bottom of his priority list. Ten years later, I was geographically separated from my boss, and our only interaction was email, teleconferencing, and phone calls. We did not have that daily interaction in the office that most people have in a traditional work setting, so these interactions had to be meaningful and targeted. Yet, every time we spoke on the phone, he allowed everyone who walked into his office to interrupt our conversation and cut it short. My midterm feedback session could not even go without multiple interruptions. It was in these moments that it became clear to me that he did not value his role as a mentor nor did he value me and my professional development. Good mentors make time to intentionally develop those in their organization to build trust between them, but when this trust is broken, it is impossible to get back. Being able to give feedback (either positive or negative) is solely dependent on a relationship built on trust. Without it, the feedback will be impossible to receive.
Air Force Col. Greg Young hugs a fellow airman after returning from a deployment to the Horn of Africa at Dyess Air Force Base, Texas, Sept. 26, 2021. (USAF photo by SrA Reilly McGuire)
Active Listening
This one is tough for many leaders who get caught up in the solution before they have really taken the time to hear and understand the problem. Also, it is quite common with more senior leaders who have not perfected this skill to interrupt the conversation to quickly provide a solution so that they can move on to the next problem. Most of the time, this is not for a lack of empathy but a lack of time. Good mentors should listen more than they speak. Now, you may be thinking that this sounds counterintuitive. How can a supervisee learn anything if he or she is doing all the talking? Your mentor can only provide advice based on their experience and where they have been, and if they do not listen fully to you they will not be able to tailor that advice to your individual situation. To become a better mentor, you should try not to dominate the conversation. Fully listen to what your Airmen is working through and then ask questions that will encourage them to think about their decision and how they came to that conclusion. Providing a solution to every problem might save time, but it may not be the answer. By encouraging them to reflect and collaboratively explore solutions you move from solving their problems to teaching a developing problem-solving skill. Those you lead will be able to understand what went well, what did not, and how they might do things differently the next time.
Gen. Mark A. Welsh III, U.S. Air Forces in Europe commander, listens to Airman 1st Class Patrick Lura, 100th Operations Support Squadron air traffic controller, during his visit to the aircraft control tower here Jan. 19, 2012. Welsh was at the base to meet Airmen and brief base leadership on upcoming changes and challenges in the command. (U.S. Air Force photo by Tech. Sgt. Neal X. Joiner)
Regular and On Time
Your main goal in mentorship should be to help people progress toward their goals, to help them be better, and then find opportunities for them to thrive. This path requires you set expectations and provide regular feedback throughout the process to construct positive change. Feedback must be regular and timely. Waiting on annual performance reports, midterm feedback, or even just event-based counseling slows down individual development and the team’s professional development. Great bosses rely on more informal face-to-face meetings throughout the rating period to provide that regular feedback. Not only do these meetings show you truly care about the individual, but they enable both parties to confirm you are on the same page and course correct during the process. Couple informal feedback with scheduled, prepared sessions that allow you uninterrupted time to dedicate to those you lead. Once you schedule the meeting, dedicate additional time to prepare before the meeting to ensure your feedback is focused and you can help your people get from where they currently are to where they want to be. In doing so, you will cultivate a workforce capable of great things, one where “losing horses” win.
Summary
Innovation and a forward-looking mindset have long been key aspects of Air
Force culture. Today, Airmen worldwide continue to exemplify these traits as they find innovative ways to implement new programs and processes to accelerate change in support of Air Force Chief of Staff Gen. Charles Q. Brown, Jr. ‘s “Accelerate Change or Lose” strategic approach and accompanying Action Orders. (U.S. Air Force graphic)
Former Air Force Chief of Staff General Charles Q. Brown, Jr. has challenged all Airmen to “Accelerate change or lose,” but how do we know what to change without the proper feedback? For the last few years, the Air Force has been hemorrhaging talent to the civilian work force. While benefits, paychecks, and housing allowance may play into that decision, we have to consider how we value our people and how we demonstrate that through development and career progression. I’ve heard from multiple officers from 2nd Lt to Majors say the same thing, “I don’t feel valued” or “I’m just a number that my leadership will replace.” We must do a better job of managing talent by mentoring intentionally, developing personnel, and then placing them in opportunities to shine. In 1913 the winner of the Kentucky Derby entered the Derby at 91-1 odds. “Why bet on a losing horse?” my supervisor asked rhetorically. Because every horse pays off at some point or another, if given the opportunity to run its race. But if we do not accelerate change on how we mentor our Airmen, we will lose the race where it counts.
The views expressed in this article are those of the author(s) and do not necessarily reflect the official policy or position of the Air Force, the Department of Defense, or the US Government.
About the author
Lt Col Jason A. Castleberry is a career USAF logistician assigned to the Logistics Plans Division, United States Central Command as the Iran Plans Deputy Branch Chief. In addition to his current assignment, he has held a diverse range of assignments to include United States Air Force Academy Assistant Professor, as well as positions at the Flight, Squadron, Wing, and Staff levels in CONUS, OCONUS, and Expeditionary environments. He can be contacted at jason.a.castleberry.mil@mail.mil.
Works cited
[i] Forbes article https://www.forbes.com/sites/marvinkrislov/2022/06/30/side-doors-and-unspoken-rules-are-key-to-success-and-mentors-can-help-first-gen-students-find-them/?sh=5b07fe4076f8
[ii] Forbes article https://www.forbes.com/sites/marvinkrislov/2022/06/30/side-doors-and-unspoken-rules-are-key-to-success-and-mentors-can-help-first-gen-students-find-them/?sh=5b07fe4076f8
[iii] https://hbr.org/2014/01/your-employees-want-the-negative-feedback-you-hate-to-give