Leadership Tips from a Ten-Year Military Career

Dan Singer
9 min readOct 7, 2019

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I recently found, hidden among one of the myriad of boxes still unpacked within my home, some older military-related items; Most notably my extensive collection of notebooks. As an officer, one should never be without pen and paper and as such, many a dog-eared notebook serves as a written testament of my military career. Among the hastily taken notes, diagrams, and idle doodles, I stumbled upon the running list of leadership tips I maintained throughout my career. While I would like to say that I captured these tips from exemplars among my fellow leaders, more often then not I cited examples of what I did NOT wish to repeat as a leader…I will, however, admit that upon reviewing this list of tips for a leader, a good portion of them actually originated from colleagues in some manner as sage advice or wisdom.

With 75 items listed over the course of the years, it would be impractical to showcase them all. I have, however, curated eleven of the most relevant, simple, and least cynical of leadership tips I have acquired over a ten-year career.

#2. Adhere to integrity at all times

This tip really should go without saying, and truth be told it is not unique to me or any particular leader, it is simply a best practice for any organization to prize integrity among its members across all levels of leadership. It is, after all, a core element to the Army Values.

#6. Self-expression is a critical element of your job. Do it well.

This has been, and remains, a particular pet peeve of mine. With my final years in service being an exception, the majority of leaders within the Army lack a talent for self-expression (and yes, I realize I am painting my fellow officers with considerably broad brushstrokes). While the very nature of our job as military officers requires clear and concise communication, I find it to be of great annoyance that most college-educated officers have a rather tenuous grasp of the English language and would prefer to sound “Hoo-ah” (or Gung-Ho to put it in other words) over sounding intelligent. It has always been my opinion that if one is to lead by example and lift our subordinates up, we need not “talk down” to their level. You don’t necessarily want to sound like a passage from a Dickensian novel when speaking to your team or your peers, but I feel very strongly that you are doing nobody any favors by devolving to overly simplistic oral and written communications. Raise the bar for meaningful discourse and most will make efforts to rise to the challenge.

#10. Don’t forget to laugh.

Our jobs can be stressful. It doesn’t matter if you are in the military or not. Jobs of all kinds impose pressures on us in some way. I have always been a firm proponent of laughter. Have fun when you can. For many of us, life is often tough enough. Granted, be smart. There are times when levity is not appropriate; but I’ve always enjoyed highlighting that, as a leader, it doesn’t diminish your authority or position to smile once in a while. Such an approachable and legitimately affable manner is not only contagious, but motivating in many circumstances.

#13. Training events should have meaningful objectives.

We’ve all been in training sessions where we pondered the much more useful activities we could be doing in place of the PowerPoint slides bombarding our retinas ad nauseam. If this is a feeling your trainees are experiencing, there are likely two things going wrong with the session: Your instructors are not engaging the audience, or your training lacks meaningful objectives. Training for the sake of logging “hours trained” for your organization is a waste of valuable resources and even worse: a waste of time. Conducting an adequate needs assessment of your organization’s training requirements can help determine what you will be covering in training as well as clearly outline the desired end-state of the training. When communicated in an engaging manner will create “buy-in” for your audiences rather then generate cynicism and boredom.

#22. Hunt for the “Good Stuff” every day.

Essentially, find ways to be positive and realize that even during the darkest of days, there is something good in your life. Okay. So this one actually isn’t one of mine. I have still made note of it in my rather lengthy list of tips. It actually is a core element to the Army’s Resiliency Program, which contains a number of great lessons for managing stress and finding positive value in any number of factors in your life. While not seemingly compatible with the outdated philosophy of “suck it up, and drive on” for which the Army is known, it does actually contain some truly valuable advice on managing stress to make you more resilient in the face of adversity (most especially for those of us occupying roles with a great deal of pressure).

#26. Don’t Sugar coat results and expectations. If failure is present, fix it!

When we have an aversion to presenting our mistakes or risks to stakeholders, I refer to this as “tap dancing” around PowerPoint. If we can talk around the facts and avoid presenting bad news, we dance around the actual issues…as such, we have created opacity within our organization. If our results are not ideal or expectations are unrealistic, we must possess the moral fortitude to say that things went wrong. Identifying ‘failure’ (a bit of a strong word, I’ll admit) is the first step in making corrections and finding solutions. Hiding our failure (or selling our mistakes as a success) is not only dishonest, but prevents us from fixing issues in our organizations and projects. Worse yet, this lack of transparent communication can lead us to continue to pursue failing programs and initiatives (a continued expenditure of resources and time) without at least revisiting them and determining the root cause of the issues.

#28. Don’t tell me what you can’t do. Provide a solution: “The Road to Yes”

Often times I use the term “The Road to Yes,” and sometimes it isn’t fully comprehended. Taken, out of context, the term really can be quite ambiguous. I took this particular term from a conference on disaster response and relief, and stands in direct opposition to to the statement: “I can’t do that.” True, many times we are asked to accomplish tasks that may be too monumental for our organization to undertake or outside the scope of our charter. Rather then tell our stakeholders that we cannot do it…why not present alternatives or an MVP (Minimum Viable Product). In some way we can at least find a way to manage our stakeholders’ expectations and deliver something that can work. When we say, “Sir, we can’t do that.” and don’t explain further or provide options or solutions, we are being intellectually lazy and accepting defeat before we even begin. The Road to Yes refers to the mental processes of finding a way to say “yes” to our stakeholders. So, when confronted with this situation the more preferred answer would be: “Sir, regulations and other constraints will not allow us to accomplish what you ask, but I think I have an alternative that can at least meet you half-way or still meet your desired end-state.” At the barest of minimum we can at least vocally illustrate that we can seek alternatives and be prepared to present these options at a later date.

Note: There are cases you can (and should) say “no. “This exception is if you’re being asked to do something morally, ethically, and legally wrong. In these cases, it is best to illustrate how legal and ethical frameworks makes the idea a bad one for the organization and the brand.

#40. If you don’t give guidance; don’t have expectations.

Yet another tip that I have taken from a fellow leader. An old Sergeant Major had quietly provided this advice to a cadre of young officers. As leaders we understand that expectation management is key in engaging our stakeholders…yet, one key person we neglect in this process is ourselves. The most valuable piece of advice I have in avoiding this situation to begin with is ensuring that you provide transparent and clear communication with your teams early; not only to set the tone for your work going forward, but also to set well-defined expectations and guidance to limit the amount of guesswork your teams will have to employ to see your goals come to fruition. The vast majority of us are, in fact, not mind-readers.

#56. When everything is a priority, nothing is.

In a high-stakes environment we want to ensure that all critical tasks are completed. Yet, in circumstances where execution on a tight schedule is key, some leaders make the mistake of assigning equal importance to all tasks encompassed in the particular mission or objective at hand. There are definitely tasks that are absolutely required for the bare minimum of success. As pro-active leaders we do not wish to acknowledge the minimum requirements…we always want to excel and surpass expectations. Yet, teams and individuals need to be able to effectively prioritize their work. When you assign equal importance to everything, lesser tasks receive the same amount of attention as the critical ones. You must put forth the intellectual work into assessing your goals and determining what tasks constitute a point of failure for your mission/project/program. Prioritize those tasks so that they can receive the most attention and allow your teams to effectively work down from your prioritized backlog of tasks (as the Agilists would say).

#57. They won’t care how much you know until they know how much you care.

This is one I took from my training prior to taking on an advisor stint with the Afghan Security Forces. The phrase has a great palindromic ring to its cadence (one of the reasons I quickly jotted it into my notebook). While one of the tenets of my own leadership philosophy is knowledgeably, your sincerity is of equal (if not more) importance. You can possess all the subject matter expertise and authority in the world, but if you visibly have a lack of interest (either in the people you are leading/instructing, the subject matter itself, or the mission) then those you seek to coach, mentor, or drive a project will assign that same level of interest in their minds. Your apathy and lack of passion serves as a detriment to not only you but also to those you lead. The bottom line being: be passionate about what you do and communicate that passion to make your own expertise that much more relevant to those around you.

#61. Always recognize superior work of your subordinates.

I personally welcome constructive feedback. I also believe that we do not improve ourselves by patting ourselves on the back. Having said that, it can be a great feeling to have your accomplishments applauded and recognized. While praise delivered in public is great, even a private moment telling your team member that they delivered some great work will be appreciated. I would only add, that doing this in public (if done properly) can lend further sincerity to your praise, as you are not afraid to loudly proclaim that “this person on my team did amazing work and that our team’s success could not have been realized without their efforts.” All too often I’ve seen some leaders implicitly take credit for a team’s success by virtue of their “management” by not recognizing the efforts of those members of the team actually executing the tasks of the particular objective.

One of my many dog-eared notebooks from a decade as an Army Officer

Note: Be wise when you praise. To be truly appreciative and impacting, your praise not only needs to be genuine, but also highlight truly stellar performance. It may seem silly, but I’ve been to award ceremonies where soldiers were praised for their ability to show up to work on time every day for a month or for successfully passing their physical fitness test. Simply accomplishing the baseline tasks expected of you as part of your job and as a professional are not necessarily laudable activities.

Great leadership advice is not limited to these eleven selections. These do, however, serve as the foundation of my own leadership philosophy. Sharing and being honest about our leadership experiences helps us to grow and improve over time, and it has the added benefit of helping us realize that we are not crazy; that often times, those of us in a leadership positions, have experienced similar challenges and problems. By sharing our experiences we can benefit from our collective wisdom and perhaps identify new approaches or techniques that we would otherwise not have discovered on our own.

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Dan Singer

Army Veteran, Project Manager, Content Monger, and a bit of a Nerd.