Leaders live in the grey????

The title of this post is based on something a former boss of mine told me almost a decade ago. When he said it, he didn’t include the question marks. He said it with an exclamation point, but it has been something I have been wrestling with ever since.

Back then, I was serving as a new school principal. I had an amazing staff, an incredible community, and wonderful students, but every once in a while an issue would rise up among people that would require a difficult decision to be made.

As a school leader, I have a few grounding principles:

  1. I believe if we get people to weigh in we don’t have to work on buy-in.
  2. I believe in the power of triangles over circles. I think having an identified pattern of checks and balances works better than having an elite group of “chosen ones”
  3.  I believe, as Marcus Lemonis from the CNBC show The Profit proclaims, success comes from people, processes, and products.


I am currently in my twentieth year as a professional educator and have had the luxury to work in six different schools. I believe that each school I left is better off now than when I was there. Just as a parent, my legacy will be defined not by the kids I raise today, but by the future adults I help cultivate, a school should not be defined by the current status or the people within its walls today, but by the generations that are changed, and this is why I struggle with the leadership advice given to me seven years ago. Right and wrong should not be decided by the person who currently occupies the largest office. Norms, values, and cultures should not be easily upended with every new executive hired. Simply because I was given a desk and a placard did not make me the arbitrator on right and wrong.

Now let me be clear, I am not an expert on this. As a matter of fact, I would love to read your comments or hear your thoughts on this concept after you finish reading this. This is truly something that has been rattling around inside my head for almost ten years.  I just can’t quite fully grasp living or leading in the grey. This is a struggle for me, because, as many who have met me can attest, I have a very difficult time not trying to be the smartest person in the room. I struggle with not having to solve every issue and not fixing everything that I perceive as broken, but this is also why I think living in the grey is such a dangerous place to be. My ability to lead should not always be about the thoughts, beliefs, and opinions inside my head.

Leadership is not about relativism. Leadership is about vision casting. Leadership is about supporting and nurturing. Leadership is about culture building. Leadership is about integrity, truth, and transparency, and to be honest, I am not sure how these are fostered in the grey.

As a leader, I believe my job is to build processes and systems, built out of the people to help support the creation of a product. As a school leader, my teachers, parents, and principals are the best people there are. I am charged with engaging them in conversations that help us create processes to support the needs of our students, the products. We are entrusted to create plans to meet the needs of each student, not just every student. We create on-ramps and off-ramps. We create entry points and exit points. We create programs and procedures. We adjust. We adapt and we evolve. We work to support equity as well as equality. And we do it all in the open with a mindset focused on growth and improvement.

Here is my struggle. And I am going to be very open and honest about it. When I began that assignment as a school principal almost a decade ago I was charged with the task of ensuring my school had the best teachers available to work with our students each and every day. “The Best” is a subjective term that brings up a variety of value judgments depending on the assessor. “The Best” teacher to some may have the highest standardized test scores. “The Best” may have the biggest demand for classes during student scheduling. “The Best” may be the one who causes the least political disruptions or the one who is “The Best” friend with parents or community members. Subjectively determining “The Best” is leading in the grey.

Back then I was charged with developing an accelerated pathway for “The Best” students”. To some, “The Best” were the students with the highest grade point average. To others, “The Best” were those with the highest test scores. Others argued, “The Best” had the most assertive parents, while others believed “The Best” caused the least disruption, were the most extroverted, or the most socially engaged. This was leading in the grey.

Back then I was charged with creating a discipline plan that removed “The Worst” from being a part of daily instruction so they could not be a distraction to “The Best”. To some, “The Worst” were the defiant and disengaged. To others, “The Worst” carried a reputation. Some believed “The Worst” were defined by the legacy established by their parents. This was leading in the grey.

Please understand that I completely agree with the need to differentiate for each as well as for every. I completely agree with the need to fight for one as much as we fight for hundreds. But this is also my struggle. Often when we lead in the grey we lead for ease as opposed to success. When we lead in the grey, our exceptions to do not become rules, but remain as outliers. If it is good for one, should it be available for all?

As a relatively new leader, back then, I found myself in a position of often working to bring about unity, while at the same time causing division. Each time a process, procedure, or program was designed a squeaky wheel would be given a pass to do as she pleased. As opposed to creating a sense of differentiation, this caused a sense of favoritism and discouragement. When a process was developed to identify an established curriculum pathway, an aggrieved parent would be given an exception. When a vocal community member complained about a teacher, despite a process for growth and evaluation, the teacher was removed.

Again, don’t get me wrong. We must respond to the needs of individuals. We must meet each person where they are. But, we need to do so in a way that is black and white. We must have a moral compass that doesn’t sway. We must have a purpose and a framework that is steadfast. We must have standards, just as in the classroom, the standards define what we do for all, while allowing for freedom in how we do it, a leader must have standards, that are…standard. When we lead in the grey, we create ambiguity. When we lead in the grey we create uncertainty and doubt. When we lead in the grey we cause strife, competition, and division.

I know this because I lived it. I know this because as a new leader trying to find his way I made the decision to live and lead in my own grey. I professed to serve those who worked for me, while at the same time fighting for my own career advancement by looking for what I perceived to be the path of least resistance. Leading in the grey was an opportunity for me to blow wherever the winds were blowing in an attempt to protect myself politically while justifying decisions as best for individuals.

Today, I know that the best leaders live in a world of black and white. This doesn’t mean we are rigid and unbending. It means when we identify a new “right” it becomes right, not just for the loudest or the recent, but for all. When we identify a new level of acceptance, it is not just for the chosen few, but for the masses.

Again, this train of thought is something that is still evolving in my own mind. I would love to hear what you think, whether you agree or disagree. Let me know, be black and white, is living and leading in the grey, right or wrong?


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1 thought on “Leaders live in the grey????

  1. “When we lead in the grey, we create ambiguity. When we lead in the grey we create uncertainty and doubt. When we lead in the grey we cause strife, competition, and division.“

    I think there is something to what you are writing here, and I’m not sure how one makes “black and white” work in the long run. This blog got my wheels turning.

    The path of least resistance is too tempting if so many other important pieces are not in place or prioritized. A lot of times I fear that easy becomes tradition because … well, it’s easy. Easy is rarely easy for ALL and that’s when the questions are raised. There are few things more stifling to progress than a silent room full of dozens of unasked questions and surface level conversation in “the grey”.

    Asking questions as an educator or raising concerns in an environment that operates in “the grey” or doing so without support takes incredible skill to earn “staying” power among peers. Without a team and shared purpose (Sinek’s WHY) and high levels of trust, that grey comfort zone is where we ”operate” to survive.

    My read is that you’re thinking with an eye on progress for all. My experiences have reinforced for me that it takes a special leader and a dedicated team to support risk-taking and to positively shift momentum.

    My two cents. Felt good to write. Been too long. Thanks.

    “ We must have a moral compass that doesn’t sway.” Spot on.


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