“We have time for one more question before we wrap up today’s event.”
Sometimes one hour isn’t enough time to cover everything during a webinar, especially when there’s so much to unpack about district leadership.
That was the case for our popular webinar, The First 90 Days: Leadership Strategies That Define the School Year where Dr. L. Oliver Robinson, Former Shenendehowa School District Superintendent, and Kristin Dudek, Chief of Student Supports and Information at Salamanca CCSD, shared insights on the leadership decisions that matter most at the start of the school year.
By the end of the event, our audience had submitted a record number of questions for the Q&A. Hearing advice from fellow district leaders was an opportunity attendees didn’t want to pass up.
We didn’t want to pass up the opportunity to get those questions answered either.
So, we sent six of the most-requested questions back to our speakers and asked them to weigh in. Read their responses below for timely insights on district leadership.
Q1: How do you hold the line on district priorities when the school board or community is pushing hard for something that isn’t aligned?
Answered by Dr. L. Oliver Robinson, Former Shenendehowa School District Superintendent
The answer is embedded in the question. District priorities. It is never about an individual or a particular group. It is about the mission, subsequent goals, and essential objectives.
People should not have to guess what the district is focused on. Absent such clarity is when other propositions surface and take root. Most importantly, district priorities should be in tune with the community and take the climate, capacity, and structure into account. In other words, priorities should not be binary. Priorities should take into consideration both the facts of the matter and factors of the circumstances.
Lastly, be reminded that board members, community members, and the media will always have a narrative about the superintendent and the organization. The question is whether that narrative is shaped by the leader or by default. Every public appearance, community presentation, and budget roadshow is an opportunity to control the narrative. Leaders who abdicate this responsibility do not remain in control of their own reputation and are much less able to sustain consistent community support and backing. Make deposits in good times, so you have something to withdraw in times of challenge.
Q2: How do you know when it’s time to walk away from an initiative that isn’t working? Especially once you are already a few months in and have told staff it is a priority?
Answered by Kristin Dudek, Chief of Student Supports and Information at Salamanca CCSD
There is an important distinction between abandoning an initiative and adjusting course. Strategic priorities should not be so rigid that they ignore evidence. Before launching any initiative, I try to establish what success will look like and what indicators we’ll use to measure progress. If, after a reasonable implementation period, the data, feedback, and operational realities tell us that the initiative is not producing the intended outcomes, then leaders have a responsibility to reassess.
What builds trust is not sticking with something that isn’t working. It explains why a change is needed. I would rather tell staff, “We learned something, and the evidence suggests we need a different approach,” than continue investing time and resources in a strategy that isn’t benefiting students or staff. In fact, modeling responsiveness to evidence can strengthen credibility because it demonstrates that priorities are student-centered, not ego centered.
Q3: What is the best way to bring non-instructional staff (HR, finance, facilities, transportation) into the conversation about priorities and when should it happen?
Answered by Kristin Dudek, Chief of Student Supports and Information at Salamanca CCSD
As early as possible and with continued invitations to the table.
One of the biggest mistakes organizations make is treating strategic priorities as instructional initiatives and then asking operational departments to support them after decisions have already been made. In reality, every district priority has resource, staffing, facilities, technology, transportation, communication, and compliance implications.
I’ve found that the strongest plans are built when non-instructional leaders are involved during the planning phase, not the implementation phase. They often identify barriers, opportunities, costs, and unintended consequences that instructional leaders may not see.
Just as importantly, bringing those departments into the conversation early communicates that they are not support functions on the sidelines. They are essential partners in achieving outcomes for students. When everyone understands how their work connects to the district’s priorities, it creates greater ownership, alignment, and sustainability.
Q4: How can I give support to a principal who is falling short of expectations, without taking away their autonomy?
Answered by Dr. L. Oliver Robinson, Former Shenendehowa School District Superintendent
The superintendent’s job is not to deliver bad news. It is to help people discover what they have to contribute. It is to make clear what the organization needs, so that any gap between the two becomes self-evident.
When expectations are clear and honestly communicated, people either rise to meet them or self-select out. Either outcome serves the organization.
The developmental question becomes, “How do I help this person see what they can contribute?”, rather than, “How do I compensate for what this person cannot do?”.
Personnel challenges essentially reduce to one of two root causes. Either a person lacks the skill to do what is being asked, in which case the leader’s obligation is to develop them. Or a person lacks the will to do the task or to develop the skill, in which case no amount of development will close the gap.
The leader must distinguish between the two before determining the response. Addressing a will problem with a skill solution is expensive and futile. Hence, for every good hiring process, there must be a good firing process. Some people must find their magic elsewhere.
Q5: Beyond general ethics and PII, what would an actual AI guardrail policy look like in practice? Do you have a template or set of guidelines you’d recommend?
Answered by Dr. L. Oliver Robinson, Former Shenendehowa School District Superintendent
Personal bias aside, being one of the initial architects of the process to develop a comprehensive policy, I would point to the Shenendehowa CSD comprehensive AI protocols at this link.
As the opening paragraph of that document states, “At Shenendehowa, we have embraced the challenge of maximizing the opportunity that AI provides while also looking to minimize the associated risks. Our goal is to empower our students, faculty, and families to engage with AI properly. We believe, when properly guided by an experienced and professional staff, AI can enhance teaching practices, support personalized learning experiences for students, streamline administrative tasks, and improve overall educational outcomes. In the landscape of constantly evolving AI capability, we are constantly evaluating our work with AI to promote Safe, Ethical, and Effective practice.”
Q6: You’ve had a long tenure and have been able to build trust and show consistency. What would you tell a leader who’s starting fresh this year and doesn’t have that history to lean on?
Answered by Kristin Dudek, Chief of Student Supports and Information at Salamanca CCSD
Trust is built through small, consistent actions over time, not through a title or a strategic plan. I would tell them not to try to borrow credibility they haven’t earned yet.
When you’re new, focus less on proving you have the answers and more on demonstrating that you are listening, learning, and following through. Staff are often watching for consistency before they are looking for vision. If you say you’ll get back to someone, get back to them. If you make a commitment, honor it. If you make a mistake, own it quickly.
In my tenure, I have found that people will forgive a new leader for not knowing everything. It’s ok to say, “That is a terrific question, let me look into it and get back to you.” What they struggle with is unpredictability. Early on, leaders build trust by being transparent about decisions, communicating frequently, and creating a reliable experience for staff. Over time, those repeated interactions become your reputation.
Continue the conversation
These six questions only scratch the surface of the district leadership conversation. Hear more from Dr. Robinson and Kristin Dudek in the full on-demand webinar, The First 90 Days: Leadership Strategies That Define the School Year. They explore topics including setting district priorities, supporting principals, building alignment, and making decisions that set the tone for the entire school year. Watch the on-demand webinar now.
