Personalities and Systems Revisited: Leading for Long-Term Success vs Short Term Wins
In my June 2021 article entitled “Systems and Personalities: Achieving a Balance Built to Last”, I shared my experience of being a Troop Commander and how I learned, through some reflection, that I had done a disservice to the Troop by failing to build systems that would outlast my tenure and relying too heavily on personality-driven leadership. I summarized the lesson I learned by stating that “the balance between personality-based and systems-based leadership is a tough tightrope to walk. You must have a system for everything that your organization is required to do, yet maintain the personality to reach in and fix it when your system isn’t working”. [1]
A year after I wrote that article, I graduated from the Command and General Staff Officer’s Course at Fort Leavenworth and began my job as a Squadron Executive Officer determined to employ those lessons learned with my staff. Shortly after my arrival to Fort Campbell, we deployed to Poland. Now, reflecting on the past year, I’ve found that even when conscious about the need to build and enforce systems, it is easy to revert to doing things yourself if you don’t use proper management practices, understand your team’s personalities, and adapt your leadership style accordingly. Below, I share the three most poignant lessons in organizational leadership I have learned over the past year.
Only Do what Only You Can Do
Somewhat of a cliché phrase, but nonetheless I have found it to be an essential mantra of self-discipline when it comes to remaining focused on organizational rather than direct leadership. There is often the urge to jump on new tasks oneself rather than delegate them if they seem super urgent or important, or if failure at the task will bring discredit upon the organization. However, it is important to take the time to assess each new task and determine if you are the one who should be doing it. More times than not, if it is a routine task or one that you have a system for, the answer should be no. A task may seem super important and urgent, but with proper assessment may fall into another category. To better categorize incoming tasks, I have found Stephen Covey’s Time Management Matrix as described in the “The 7 Habits of Highly Effective People” to be useful. Essentially, in order to better manage our time, or as Covey describes the habit of “Put Things First”, we need to focus on minimizing the time we spend on things that are urgent but not important, or not urgent and not important. [2] Things that are urgent and important may require that we do them ourselves, but after each instance of one of these tasks arising, we should assess where a system might be put in place to reduce the urgency of the task in the future. For some of these tasks, they are important enough to require only your experience and expertise, but these should be few and far between. As a manager, your time is better served “seeing the forest from the trees” and assessing the entire workload of your staff, rather than being absorbed by a singular task. We must be extremely judicious in what tasks we keep for ourselves.
For those tasks that are important, but not urgent, we should avoid doing them ourselves and delegate them to a trusted agent, with routine follow ups as we will discuss later. For those tasks that are urgent, but not important, we should first determine if that task has to be done at all (they might be a case of stray voltage as we say, a task imposed by someone without the authority to do so with a deadline that is unrealistic), and if it must be done should be delegated and checked on. Lastly for those tasks that are not urgent and not important, we should evaluate to see if they truly must be done, and if so, they should be delegated as a long term project with infrequent touchpoints.
Rubber vs. Glass Balls and Choosing your Battles
For those important but not urgent tasks as well as those that are urgent but not important, we want to maximize the times that we delegate them to our staff. However, it may be the case that you delegate the task and it is not completed to standard or not in a way that we would like. With a deadline approaching, the urge is strong for the manager to just do the task themselves, but as I discussed in my previous article, this deprives the subordinate of a learning opportunity. It is then important to determine whether the task is a rubber ball, one that will bounce if dropped or not completed on time, or a glass one that will shatter (i.e. that will result in actual physical or severe reputational harm to the organization or its members). For those tasks that are rubber balls, it may be worth missing a suspense to focus on making the subordinate correct the product based on your feedback. In that way, the subordinate should internalize the correction and not make the same mistakes again. This saves time in the future, and develops the subordinate into a better staff member. For those tasks that are glass balls, it may require that you as the manager step in to finish the task to standard to prevent harm to the organization, but it is important to take time before moving on to the next task to address the corrections that needed to be made after the fact with your subordinates so as to not have the lesson go unlearned.
An important step that is critical to employing the above approach is to communicate risk to your commander or higher management. It is one thing to miss a suspense or fail a task because you lost track of it, it is another to make a conscious choice to do so because you want it to serve as a learning opportunity. As an Executive Officer or a Chief of Staff, it is important to remember that you don’t own the risk associated with failure, your commander does, and it is their choice what risk they are willing to accept. They might see the importance of development in a particular situation and choose to honor your recommendation to eat some risk on an unimportant task for the sake of a better developed staff. Someone who is a “Failure Tolerant Leader” as described by Farson and Keyes may have a bigger appetite for this than others, as they see the value in some risk to increase innovation and development. [3] However, adherence to this next lesson will minimize the risk we assume by teaching.
Set and Enforce Deadlines
A way to keep the tasks, rubber or glass, from dropping at all is to set and enforce deadlines. When receiving a new task and delegating it to a subordinate, part of the delegation must include when the subordinate’s suspense for completing the task is. That suspense should be backed off the final suspense with enough time to allow correction and feedback. The amount of time between the subordinate’s suspense and the final suspense should be tailored based on trust in the subordinate’s work quality and reliability. If the product will require relatively little feedback based on previously demonstrated work quality, then give the subordinate the maximum available time to work on it. If the subordinate has demonstrated that their products require serious revision and editing, then give much shorter suspenses to afford you as the manager more time to give feedback.
In the book The One Minute Manager Meets the Monkey, Ken Blanchard et al. describe the “Rules of Monkey Management” where the “monkeys” are tasks that managers delegate. One of these rules is that “All monkeys have feeding and check-up appointments scheduled”, which means that every task delegated to a subordinate requires a dedicated and prescribed follow up. [4] One of the challenges I have found is making enough time based on the litany of tasks to adhere to this principle, but the use of a simple Microsoft Outlook calendar to schedule appointments with your subordinate staff members is one tool to ensure that every task delegated receives its due follow up.
While the above rules may seem common sense or obvious in nature, it is one thing to know they must be done and quite another to actually do them. We all get caught up in the rush of work and deviate from what we know to be good practices when stress or workload put us into a sort of “survival” mode. It requires discipline and the desire to improve the organization in the long term rather than achieving short term victories, and often the conscious decision to become more failure tolerant in our approaches to task management. In this way we can buy more time for ourselves to truly see the forest from the trees, and spend more time as managers where it is better suited.
Brian Fiallo is an active-duty Army Major currently serving with the 101st Airborne Division (Air Assault). As an Armor Officer, he has served as a Scout Platoon Leader in 3rd Brigade (Rakkasans), 101st Airborne Division, as a Cavalry Troop Commander in the 1st Stryker Brigade Combat Team, Fort Wainwright, Alaska, and most recently as a Squadron Executive Officer in 2nd Brigade (Strike), 101st Airborne Division. He graduated from the United States Military Academy at West Point in 2011, earning a B.S. in Military History. He earned his M.A. in Archaeological Studies from Yale University in May 2021. His interests include forensic and conflict archaeology, blacksmithing and metallurgy projects, and exploring the outdoors with his wife, four children, and two dogs.
Opinions expressed here are those of the author and do not represent those of the United States Army, the Department of Defense, or the United States Government.
[1] Brian Fiallo. “Systems and Personalities: Achieving a Balance Built to Last”, Thought to Action Blog, thought2action.org, 2021.
[2] “How Prioritising Using the Time Management Matrix Can Improve Productivity.” Lingford Consulting, October 31, 2022. https://www.lingfordconsulting.com.au/productivity/how-prioritising-using-the-time-management-matrix-can-improve-productivity.
[3] Farson, Richard, and Ralph Keyes. “The Failure-Tolerant Leader.” Harvard Business Review, August 1, 2014. https://hbr.org/2002/08/the-failure-tolerant-leader.
[4] Blanchard, Kenneth H., William Oncken, and Hal Burrows. The one minute manager® meets the monkey: Free up your time and deal with priorities. London: HarperCollins Publishers, 2011.