Elusive Mentoring in the Superintendency

A veteran school system leader shares her experience as mentee and mentor on being supported and supporting others

I am a classic Type A, Enneagram 3, kind of person. Preparation is my superpower. I walked into my superintendent interviews fully equipped, knowing every school board member by name and occupation, having read the last 18 months of board minutes and school district newsletters in their entirety, with my 90-day entry plan in hand.

So you can imagine my surprise when four weeks later, sitting at my first board meeting as superintendent, I realized I had no idea what to do. Do I introduce the item? Do I give background information at the start or wait to be cued from my board president? For the love of all things, do I even vote?

I learned that night the need for mentorship doesn’t stop once you land the superintendency. But what is unique about the superintendency is that the onus for seeking growth is entirely on you. In every other role, people supervised your work and gave feedback. As superintendent, you may hear feedback from your staff, board or community, but it is easy to get caught in a feedback void.

This can be extremely problematic given how we evaluate our work. Leadership author John Maxwell says this: “[M]ost people use two totally different sets of criteria for judging themselves versus others. We tend to judge others according to their actions. It’s very cut and dried. However, we judge ourselves by our intentions. Even if we do the wrong thing, if we believe our motives were good, we let ourselves off the hook. And we are often unwilling to do that over and over before requiring ourselves to change.”

Perhaps for that very reason, we need mentorship the most when we become superintendents.

Obstacles to Seeking Mentorship

By good fortune, I met Jenny Preston, a successful superintendent in Texas, at an Aspiring Superintendent Academy when I was contemplating a move into the superintendency. I quickly decided I wanted to “be like Jenny,” and the next month I drove 420 miles roundtrip to have a cup of coffee, listen and learn from her. I share that story because we can’t ask someone to mentor us and then hope it will happen. We must create opportunities and put in the effort to make it happen. With today’s technology, you don’t even have to get in the car. The opportunities for mentorship are ubiquitous.

Many of us could name multiple people, like Jenny Preston, who have impacted our path to the superintendency. So if we know we need mentorship at this level and that access to wise counsel is merely a cup of coffee or Zoom call away — and we’ve spent much of our careers accessing such counsel — why is mentorship more precarious at the superintendent level?

Three factors seem to apply.

Trust. When I came into my superintendency, the district was in the midst of a financial crisis where we lost nearly 20 percent of our staff. These extremely difficult challenges came in my first year before I had a group of trusted peers. I finally opened up to a neighboring superintendent. When I casually mentioned it to my administrative assistant, she shared that that superintendent was the college roommate of the former superintendent in my district. It stopped me dead in my tracks. I’m fortunate there was no malicious intent and we all became good friends, but that day I learned that the world is small.

I also struggled to share my challenges because I didn’t want anyone to think I didn’t know exactly what I was doing. Earlier this year, Brené Brown, author of Daring to Lead, shared during our Texas Association of School Administrators conference that the past few years have been unbelievably challenging and that we were not OK. She went on to say, “Our tendency when we’re not OK is to armor up to get through the day. But learning cannot happen in the presence of armor.”

The same is true for us. We will never be our very best until we lower our armor and take the risk necessary to learn and grow. To overcome these issues, I learned to go slow, ask questions and allow trust to be earned. I also kept my analysis honest but above reproach in case something was inadvertently (or advertently) shared.

Alignment of Values. One of my first mentors as a superintendent had a healthy separation between the district/community and the leader. I had this belief of being “all-in,” so it was difficult to accept the mentor’s counsel. I understand sentiments like “it’s their kids, their schools, their money,” or “you’ve got to keep your job to do your job” now, but they fell on deaf ears then because of a misalignment in our values.

I’ve learned we can choose whose advice to accept. But I also learned that what you think may not be helpful counsel at first may actually be wise. You just don’t know it yet because you haven’t been in the seat long enough to see and understand it.

Complexity and Time. One of the most challenging parts of being a superintendent is that there are an infinite number of moving parts to every decision — the history, the people, the capacity of the leadership, the climate and culture of the district. So when an issue comes up, the amount of time it takes to situate someone else in the complexity to solicit sound counsel is not even available.

I learned to take note of how others approach decisions, how others lead through decisions, as opposed to trying to figure out what another leader would do in the situation. Organizational psychologist Adam Grant says it like this: “The best way to learn from mentors is not to absorb what they know, but to internalize how they think. Collecting their knowledge helps you address the challenges of the day. Understanding their thought process helps you navigate the challenges of a lifetime.”

Mentoring Others

I’ve always believed you can’t lead someone to where you yourself have not been. However, a great fallacy about mentorship is that there is a divergence in the road where you go from being mentored to mentoring others. I now believe it is a gift to have others pour into you while you’re developing as a leader. And it is a privilege to pour into others who are growing in their own leadership. But the magic happens when both occur simultaneously.

Gandhi noted “a sign of a good leader is not how many followers you have but how many leaders you create.” Each of my relationships with mentees was special, and developing leaders did deepen my understanding of the responsibility and role I had as a mentor.

A few considerations on furthering the relationship:

Don’t recreate your strengths. Build up theirs.

Early in my leadership I created this picture in my mind of what good leadership looked like: strong, charismatic, bold, decisive. This impacted me in two ways. First, it made me feel “less than” as I measured myself against this self-created image. It also tainted my mentor relationships. When someone sought my counsel, I coached them to do things as I would do them.

As my mentoring skill set grew, I focused instead on finding their strengths and helping them capitalize on them. As Simon Sinek notes, “A mentor is not someone who walks ahead of you to show you how they did it. A mentor walks alongside you to show you what you can do.”

Remember the weight.

It is easy to play Monday morning quarterback when looking at a situation involving someone else. In truth, there is a benefit to being removed from a situation and seeing it with clear eyes, coupled with a few years of experience. But it is all too easy to flippantly spout out counsel and later find out the situation imploded.

Joe Sanfelippo, superintendent in Fall Creek, Wis., shared this personal discovery while mentoring: “I don’t know everything about their school district, and when I try to compare it to my situation or provide advice on how to handle it, I am coming at it with a different environment and specifically, a different board.”

In many cases, we need to serve as the listener, the questioner, the critical voice and the crafter of the how — as opposed to the director of what to do. And in all situations, we must recognize that our words and counsel have an enormous impact.

Choose wisely.

Mentorships are intimate relationships that often span years. I have loved sharing my knowledge and experiences as a mentee and as a mentor. But I am acutely aware that not every request for mentorship requires a yes. Vineet Chopra and Sanjay Saint shared in a Harvard Business Review article “6 Things Every Mentor Should Do” to “beware the diffident candidate who expects the mentor to keep the relationship going, or the candidate who insists on doing things their way. A mentee should be curious, organized, efficient, responsible and engaged.”

Don’t be afraid to limit mentoring relationships when learning isn’t being sought in earnest or there is a significant misalignment in values.

Create a thought partnership.

One hesitation I have had in serving as a mentor is whether I would know enough to help others in their unique circumstances. I was serving in a rural school district and mentoring superintendents of large, urban, fast-growth districts. But I realized my job was not to have all the answers but rather to partner with mentees to help them find theirs.

Marlon Styles, former superintendent of Middletown City School District in Ohio, shared this: “Be aware of how much advice you provide versus the number of growth-provoking deposits you provide the mentee. An impactful experience will result in leaders discovering leadership behaviors that strengthen their ability to lead, serve and inspire.”

Two-Way Gains

It is easy to think that once you’ve landed in the superintendency that mentorship is not necessary or that your sole role in mentorship is to mentor others. LaTonya Goffney, superintendent in Aldine, Texas, recently reminded me though that “iron sharpens iron” — meaning we will never be our best if we are not committed to our growth and the growth of others.

So, lower your armor enough to seek wise counsel. And while recognizing the weight of your words, offer mentorship to other leaders along the way. Because when we do that, all our students, staff and communities will benefit. And so will we. n

Jill Siler, a former superintendent, is the deputy executive director for professional learning with the Texas Association of School Administrators in Austin, Texas. She is the author of Thrive Through the Five: Practical Truths to Powerfully Lead through Challenging Times. Twitter: @jillmsiler