The Leadership Conundrum – Dealing with People

The Leadership Conundrum

A conundrum is described as a problem that is difficult to deal with.

The Navy spends a lot of time in the education and development of its leadership. The organization has evolved over the centuries from a very autocratic structure that involved corporal punishment to a more nuanced organization that recognizes the need for individual team member performance. Even as a young civilian entering Boot Camp, I was given an immediate taste of the style of leadership most associated with a military organization. You quickly learned the terms you should use and avoid and behavior was clearly outlined. The reinforcement of push-ups and leg lifts interrupted by long runs around the grinder made sure that you had a very clear understanding of leadership’s expectations.


I enjoyed each level of growth I personally went through as a leader. I worked very hard to earn each level from non-commissioned Petty Officer to Chief to Chief Warrant Officer. The Navy made sure I had the regulations and schools that would shape me as a leader. Life was actually pretty simple once I figured out how to fit into that mold.

Then came the Post-Navy world.

Dealing with people can be the most rewarding and frustrating experience in any leader’s life. In a highly effective organization, leadership can be focused on continuously improving the skills and knowledge of the team members while driving for higher levels of excellence. But organizations that are not as highly effective often waste inordinate amount of time on routine behavior and discipline issues.

This phenomenon can be complicated when the mix between managers and workers is separated by background, level of education and age. Even when the managers and workers are in the same age group, leadership skills that were learned from a previous generation can cause problems and create inefficiency.

One way that can help to overcome conflict is to set clear and structured expectations from the outset. Whether the generation is the Boomer Generation, Gen X, Millennial or the Z group, setting clear expectations that are unmistakably understood is a tool that crosses all generations.

This is particularly true of the millennial generation. As a whole, they achieve much more when they have been provided the needed tools and guidelines to complete the projects they have been tasked with. While Generation X may display a fierce independence and love freedom in tackling those projects, Millennials will more than likely require more structure.

There is a fine line between micro-managing and setting clear expectations, As long as you choose to be in a leadership role, you will probably struggle with this simple axiom. Each individual will eventually help you understand when you have crossed that line but as a leader, you will also have to determine as quickly as possible what their needs are in setting those expectations.

Here are some suggested questions that you should ask yourself;

  • How much are they going to be working independently versus directly with you?
  • How frequent and what is the method of communication points where you need to check in?
  • Will the check ins have structure and how much structure is needed?
  • When is the deadline? What is the tracking methodology or tool?
  • Are there clear guidelines on responsibilities and expectations?
  • What does the final outcome look like? Can you define the deliverable in a way that is clear and without any ambiguity?
  • Finally, what are you going to do to proactively give them direction without micromanaging?

Some projects will have clear expectations. Deadlines should be firm, fair, and fixed when possible and an agreement must be reached at the onset. Some projects will also have variable formats which allow for innovation and changes in the environmental climate. Typically, this may involve some flexibility in the methods of gathering information, internal project methodology and non-critical decisions that can add weight to a process. But there should be a very clear understanding of which fall into either category. This may require an explanation into which are non-negotiable but can be balanced with which areas are going to have more freedom.

As the organization or team grows, the need for this level of management will lessen. The teams will ultimately be able to understand your expectations and you will be able to understand their capabilities. Adjustments will need to be made continually on this journey. But high performing teams eventually reach the point where project launches become much smoother, check in’s become less complicated and time consuming, and the end product of the work is very closely aligned with the original goal.

One word of caution. All of these suggestion assume that the leader and the people being led establish a relationship based on open and honest communications. Time must be spent in understanding the strengths and weaknesses of the people involved in this leadership transaction. Just as there are no perfect solutions for every case, there are also no perfect people. If shared goals and shared vision cannot be achieved, the journey will be a rough and bumpy road no matter what expectations are set and clearly identified.

The leader must remember that they have been placed in a leadership role for a reason. If the majority of their time is spent dealing with one or a few individuals that still struggle with comprehending the expectations, the organization will be less effective. Sometimes, despite coaching and counseling, you will find that individuals may just not be the right fit for the position they hold. Hiding their inefficiency for expediencies sake is not only unfair to the rest of the organization, it is poor leadership. In many cases, it is also unfair to the individual to allow them to continue in that role. Freeing them to pursue their dreams may be the best thing you ever do for them.

Mister Mac


Leave a Reply

Please log in using one of these methods to post your comment: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s