Initiative and Introspection- Worst Leader Essays

We’ll be featuring essays from our community members here weekly. These essays are part of a series that explore the lessons learned from the “worst leaders.”

“You Should Have Shown Initiative!”

By Philip B. 

The idea that subordinates should simply know information, such as the Commander’s intent, is common and detrimental to the command climate.  When I was a cadet at West Point, I first noticed this issue when the New Cadets were told to go their rooms and get dressed.  As I walked the halls I noticed all the doors were open exposing half clad people to the hallway.  I struggled to understand how such smart people would change with the door open!  I realized that I, and the other leaders, had not told them to close the doors, so why would they “just know” to do that? 

When I deployed to Iraq a few years later as an O2, a Police station near, but outside my area, was attacked, no one was hurt, but it was a big deal none the less.  I heard the report from two higher ranking officers, and as they discussed the matter I didn’t call my Command team and let them know.  My immediate superiors already knew so it was their job to call higher.  Later that night I was called by my Operations Officer, a Major, and chastised me for not telling him.  I told him that I was under the impression that the Captains had alerted him (my fault for assuming they would do this).  He told me that I should have “just known” to call him and the Commander even though the station wasn’t in our area.

More recently I had a discussion with my Command Sergeant Major about securing a training area for a Battalion event.  However, the name and location of the desired area was for a digital training and simulation area, not a physical training area.  I didn’t secure the building as it was unfit for our needs.  He didn’t understand how I had been unable to find or acquire the training area. Ignoring that the directions had been vague, I pointed out that the training area was not suitable for the goals the Commander wished to accomplish.  The Sergeant Major expressed that I have “just known” that the area the Commander wanted was behind the location I was sent to.

In all of these situation I received the second most common and wasteful response in the Army (the first being “We have always done it that way!”): “You should have used some initiative…!”

That’s right, I, as the subordinate, should have known that the training area was actually behind the location I directed to and that you actually wanted something that you didn’t ask for.  Or I should have known the other Officers wouldn’t do their jobs and that you wouldn’t know something.

As a leader I have been struck by how often military leaders use lack of initiative or a random reference to “Message to Garcia” to make lack of success the fault of subordinates rather than their crappy guidance or intent. 

Nothing will erode your status as a leader faster than giving vague guidance and then accusing the failure on a lack of understanding, or initiative, on the subordinates.  Leaders have a duty to give clear and concise guidance with a clear end state to subordinates to ensure mission success.  By providing a clear end state leaders allow subordinates to be creative in the process of mission completion while ensuring that outcomes are met the first time.



Worst Leader…­ Me

By Ryan P. 

As I think back on a bad leadership experience, I am reminded of one of my early failures as a leader.

In the summer of 2002, myself and two other friends went on a backcountry mountain bike ride through Mark Twain National Forest. The scheduled route for the day was a 40 mile loop on terrain that was completely unknown to us and we were limited to a small black and white printout for a map.

We set out on the trip with a morning start time of 9 AM however in retrospect, it probably should have been earlier given the summer heat and humidity that is common in our region. Early on, we encountered a substantial amount of technical terrain that was not rideable and was barely hike­able. The week prior we received torrential downpours and at some point between the rains and the day of our ride, the trail had been ridden over by what appeared to be a large number of horses. The ruts and boulders that had been kicked loose by horses combined with the deep holes of standing water, kept the trail rough, wet and unrideable.

As our movement on the trail was slowed by the rough terrain, we also experienced increased exposure to the elements on an extremely hot summer day that easily reached 100+ degrees.

By 2PM, the three of us had not even covered half of the planned distance for the day and we came to an opening on top of a ridge. As I was looking to see where the trail led ahead of us, my friend Sean came up to me and said “hey, I really need to get out of this, like right now.”

Sean went on to say that he was really feeling fatigued and dehydrated and that he wasn’t going to make it through the second half of this journey. At this point he drove home the urgency for us to find a route back to the trailhead ASAP.

Up until that moment, I realized I had not been paying attention to the well ­being of either of my friends or myself, as I had been so focused on the ride and getting the planned distance covered. After we talked it over and Sean reinforced the need for us to drop the original plan, we looked over the map and found a way to bushwhack down a sizable hill and pick up on an old country gravel road. Eventually that road led us out to a blacktop and we made it back to our car in about 2 hours rather than the 8+ hours it would have been.

In the end, the three of us got out of the trip relatively unscathed but in retrospect, had Sean not spoken up, I am confident that I would have continued to lead all three of us down a very miserable path.

The trip ended up being a major learning lesson for me, as it was a breakthrough moment in becoming aware of my failures as the group leader.

Since that time, I developed a mindset that no matter the type of group I am with, to approach each trip as if I were a​professional guide. ​This mindset has lead to the following:

1. Consider fitness levels of each individual in relation to the type of terrain you plan to cover

2. Research the planned route and expected rate of travel

3. Observe the physical well­being of your team and look for early indicators of


4. Pack extra food/water/emergency kit to ensure you are prepared

5. If possible, have a backup plan for emergencies or unexpected events


Worst Leader – Sergeant Major Dick

By James E.

I deployed to Afghanistan as 2IC of a team of 22 and directly below me was a Sergeant Major who we will call Dick (pun intended). As a young officer I struggled with reining Dick in and he knew how to play the game so making anything stick to him was like trying to see the back of your head with a single mirror, it just wasn’t going to happen. To summarise Dick’s leadership style is to say he led by instilling fear in subordinates who he treated as lesser humans and used to fulfil his own agenda. There are numerous examples of Dick’s appalling leadership but for the sake of this article I will identify just one. Dick wanted to RTU early and knew that one of the soldiers was expecting a child. He threatened the soldier, eventually to the point of breakdown and attempted suicide, into attempting to convince the OC and I that there were complications with his wife and child in order to persuade us to RTU a detachment (as this was a potential course of action we had been considering due to the operating environment) and Dick along with them. Dick taught me a great deal about leadership:

  1. Treating subordinates as lesser beings will destroy your team. If you fail to respect the humanity of those under your leadership you will undermine your position and close off your team members to receiving your information and providing you with theirs.
  2. Fear based leadership is not enduring. Eventually we were able to stick something to Dick but only because those who feared him had enough and gave evidence to allow us to dishonourably RTU him. Followers will quickly tire of being afraid and search for options to remove the cause.
  3. Pursuit of self over team will always fail. If you use the team to pursue your own agenda they will not follow you for long. Pete Blaber’s ‘The Mission, the Men and Me’ is undoubtedly the priority of your concern as a leader, this applies beyond the military context.

A current OC at my unit, let’s call him Carl, exemplifies poor leadership. Carl’s concept revolves around self-preservation and absence in order to avoid his duties. He makes no effort to associate with his company and, unless he must to avoid punishment, shows no care for understanding their employment. Carl is reliant on others around him to work for him and provides little to no direction. I have learnt a great deal from Carl:

  1. Incompetence among leadership is the fast road to a failing team. The soldiers under Carl’s leadership know that he is incompetent and resultantly make no effort to strive for excellence. Incompetence among leadership will breed incompetence among the followership.
  2. Self-preservation will destroy your credibility. Deciding to only care for items that threaten his personal image has resulted in his guidance being disregarded by subordinates. His credibility as a leader is destroyed through his overt display of self-preservation.
  3. Absence of leadership dismantles a team. For the first eight months of command, Carl’s company did not know that he was their leader. During this time there was no cohesion and to argue that a team existed was a long bow to draw. To lead means to be present and exploit your duties for opportunities to lead further.

I have been exposed to horrific leadership as well as good leadership. Unfortunately, the former is more often remembered.

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