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Josh Bowen

Mentorship and My Leader Development: A Dilemma

Updated: Oct 9, 2023

Josh Bowen is an engineer officer in the U.S. Army and is currently serving at the United States Military Academy as a Tactical Officer (click here to find out more about USMA’s TAC Program and it’s associative masters program at Columbia University). He also supports USMA’s Department of Behavioral Sciences & Leadership through teaching PL300 Military Leadership, which is the Academy’s capstone leadership course required for all cadets in their 3rd year. He is passionate about leader development; he writes and edits his own blog, 3×5 Leadership, which covers a variety of leadership and leader development topics. You can connect with Josh on Twitter and Facebook. His views are fully his own and do not reflect that of the U.S. Army or the United States Military Academy.


Mentorship as Leader Development No holistic approach to leader development is complete without mentorship, both at work and in our lives. It’s vital in providing the perspective, challenge, and support necessary in enabling young leaders to learn, stretch, and grow their abilities and understanding. Yet, just because it is important obviously doesn’t mean it is easy. I enjoy writing about leadership and I even write about how important mentorship is, but the bottom line is, despite recognizing the immense value of mentorship in my life, I’m tend to be pretty terrible at it.


My Struggles with Mentorship

Yes, I’ll admit that I struggle with being a mentor – I sometimes fail to take the initiative and regularly check-in with old subordinate leaders from years past. I also struggle with being a mentee – I’m fearful of asking senior-ranking leaders for their added time; I wonder ‘who am I to demand additional time from this already-busy influencer?’ I’ve found my personal leader development lacking in a few ways due to my struggles with mentorship.

I imagine there are others that feel the same, whether not being as active as mentors as they should be, or not seeking out quality mentors themselves as a mentee. There are several challenges associated with mentorship that we all feel at times. It is challenging for many of us because time spent toward mentorship does not often result in direct, tangible impacts on our organization’s task or mission.


Recommendations for Mentors & Mentees Since my recent great fortune of building a friendship with Chevy Cook, Military Mentors’ executive director, I find myself thinking about mentorship much more…especially how I need to mature my mentorship habits. So, I want to offer a few recommendations I’ve been thinking about for both mentors and mentees as we all strive toward growing ourselves and developing the 2nd and 3rd generations of leaders to follow behind us.


For Mentors

  1. Start with your current leaders: If you are looking to initiate your role as a mentor, start with the leaders within your current organization. I encourage you to regularly include deliberately developmental conversations with your subordinate leaders (not directly tied to your unit’s current mission or training) to help provide perspective to their struggles at hand. My favorite, and incredibly simple, mentorship model is: 1) listen, 2) share what you know, and 3) repeat.

  2. Keep your group small: It is unrealistic to expect to keep in touch with everyone, let alone mentor every subordinate leader you have ever worked with. Consider a sustainable and feasible span of mentees you can handle; I’d recommend one to six. Your relationships may have differing seasons over time and look different, but keeping your mentorship pool small ensures quality over quantity.

  3. Formal vs. informal: Some mentorship relationships may be formal, with an agreed-on “contract” (when, where, how often you meet; topics; etc.). But mentorship doesn’t have to look like that; it can be just checking-in monthly or quarterly or working with your mentee when they have an issue or decision to work through. Agree on and engage in a meaningful relationship that works for you and meets your mentee’s needs. There’s no “right” way.

  4. Scroll your phone contacts: Chevy taught me the habit of simply scrolling through my phone contacts on a semi-regular basis and sending a quick text or making a quick call to subordinate leaders of years past. You could also improve your use of your contacts list in a few different ways. Even a simple text message communicating that ‘I’m thinking of you, hope you’re doing well, and let me know if you need anything’ can make your mentees comfortable in seeking your counsel in the future. It keeps you available.

For Mentees

  1. Know that mentorship can happen within the chain-of-command: Mentorship is a leader development method; your current boss can serve as a mentor in certain capacities, just know how to best utilize the relationship. Don’t shy away from viewing your boss or other senior-ranking leaders in your current chain-of-command from filling mentorship needs in your development. I, personally, have received a lot of mentorship from my commanders for seasons over my career at certain times.

  2. Formal vs. informal: You can establish a formal relationship where you schedule to talk with your mentor every week, month, etc. But if you don’t have that, don’t consider yourself lacking a mentor. Mentorship can also be reaching out to a trusted senior leader to help you work through a specific issue or decision you’re currently working through.

  3. Have a coalition of mentors: It’s unrealistic to consider a single mentor meeting all your developmental needs. I encourage you to build a coalition, or a mentoring board of directors, of mentors that you turn to. They each may support a specific developmental need. For example, I look to one leader to help with my engineer officer career management decisions, another one that I turn to for my continued exploration in better understanding leadership, and finally, still a different leader that helps me in my blogging efforts.

  4. Send an annual email: If you’re like me and struggle with the confidence to reach out to respected mentors to maintain the relationship, I encourage you to send them an annual email. Your email should be concise but provide a brief professional update over the last year and what is coming next for you. A simple email helps maintain open lines of communication and keeps them current with your life events. Plus, I highly doubt any caring leader that you respect would not enjoy hearing from you every now and then.

Thanks for your time and your leadership, especially investing it into our future generations of exceptional military leaders. Lead well, friends.

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