The Leadership Skill Schools Need Most: Timely, Courageous Conversations

Across K–12 systems, HR responsibilities have become inseparable from instructional leadership. Schools and districts are expected to raise achievement, retain talented staff, and make high-stakes personnel decisions on increasingly tight, uncertain timelines and budgets. In that environment, the most overlooked lever for improving instructional quality is not a new tool or initiative. It is a leader’s ability to have clear, timely, and honest conversations with employees—conversations that protect students, strengthen culture, and prevent minor issues from becoming system-wide problems.

That theme grounded a recent conversation with longtime educator and former Assistant Superintendent of HR at Milpitas Unified School District Jonathon Brunson, whose career spans roles as a teacher, principal, and district HR leader. Brunson argued that courageous conversations are not side tasks. They are the mechanism through which HR, principals, and school and district leaders ensure that the right adults are in front of students, expectations remain clear, and staff have a fair chance to improve. “These aren’t other people’s children,” he said. “These are my children, and I need to take care of them.”

The heart of his message was simple: schools flourish when leaders bring clarity to tough conversations and address issues before they grow.

Anchor Hard Conversations in a Student-First Mindset

Brunson’s starting point was always the same. Effective HR work begins and ends with the student experience. Leaders may hesitate to confront performance issues because the moment feels personal, but the consequences of inaction fall squarely on students. As he put it, “When you have to have that hard conversation, put in your mind that you’re doing this for kids and it’s going to make it that much easier.”

He urged leaders to consider a basic question whenever they evaluate practice:

Would you want this person educating your own child?

If the answer is uncertain, the conversation cannot be delayed. “If there’s any doubt, there’s no doubt,” he said—a statement that surfaced repeatedly throughout the session.

This framing gives leaders a way to navigate discomfort without losing compassion. The goal is not to punish adults. It is to ensure, as Brunson explained, that “you put the best adults in front of children” because doing so “creates a great school.”

Centering conversations on student impact transforms them from moments leaders dread into moments that safeguard instructional quality.

Early Feedback Protects Both Students and Staff

To Brunson, one of the most consistent pitfalls in K–12 HR is treating probationary status as a countdown instead of a continuation of the hiring process. He captured this plainly: “Probationary status is an extension of the interview process. They are still interviewing for the job.”

The transition into this point matters. Leaders cannot protect students if they wait until spring to name concerns. Strong evaluation practice requires early, repeated, and written communication—long before high-stakes deadlines like March 15. When feedback is delayed, new educators are blindsided, unions lose trust in the process, and leaders find themselves responsible for staff who may not be ready for permanent status.

Brunson described the avoidable harm that results from hesitation. He has seen employees learn they are being released only after six months of silence. “They say, ‘I don’t understand. Why am I being released? Nobody’s talked to me about anything.’” At that point, the system—not the employee—has failed.

Early clarity is not unkind. It is fair. It gives employees time to grow, and it prevents years of downstream challenges that occur when districts inadvertently grant permanent status to someone who wasn’t ready.

Brunson’s argument reinforces a foundational principle: timely, evidence-based feedback is both a protection for students and a professional courtesy to staff.

Use Evidence and Support to Drive Growth, Not Just Compliance

A major strength of Brunson’s approach is his insistence on specificity. “Do your homework,” he told participants. That means grounding feedback in what was seen, not what was assumed. 

During one classroom visit, he noticed “five students had their heads down and were not listening,” and the teacher did not check on any of them. Instead of turning this into a reprimand, he asked reflective questions. Had the teacher noticed? What strategies might re-engage students? How would they adjust the next lesson?

This evidence-based structure does three things at once:

• It gives the employee a clear picture of what happened
• It keeps the conversation rooted in practice rather than personality
• It opens space for genuine coaching rather than defensiveness

Brunson also stressed the importance of following each conversation with a written summary—not to build a case, but to ensure shared understanding. “You are creating a track record,” he explained, one that protects schools and districts from claims of bias while helping the employee track their own progress.

Accountability Builds Culture—and Staff Pay Attention

Accountability is often discussed privately among administrators, but its effects are deeply cultural. As Brunson explained, strong staff notice whether leaders uphold expectations. “Nothing can deflate a team more than when the head coach doesn’t hold people accountable,” he said. When leaders ignore persistent concerns, it unintentionally signals that excellence is optional.

Conversely, when school leaders address issues with clarity and respect, positive staff feel validated and protected. They see that the system honors their professionalism and refuses to lower the bar. This strengthens morale, reinforces trust, and aligns adults around a shared standard of quality.

Brunson’s advice was simple. Be compassionate, be consistent, and be honest. People may not enjoy the content of a tough message, but they will remember how they were treated. Respect and transparency matter as much as the decision itself.

Addressing performance issues openly and respectfully reinforces the norms that high-functioning teams rely on: consistency, trust, and a shared commitment to students.

Strong instructional systems depend on leaders who are willing to speak plainly, act early, and treat people with honesty and respect. Courageous conversations are part of how schools maintain high expectations, protect student experience, and support staff in refining their craft.

These conversations take practice, preparation, and willingness to choose clarity over comfort. But when leaders commit to this work, they create the conditions for better instruction, healthier cultures, and more stable teams.

For leaders navigating similar challenges, the insights shared in this conversation offer a reminder that courage is not a personality trait, but a habit that strengthens every part of the system.

As schools and districts continue navigating shifting expectations, strong people systems matter as much as strong operational systems. If you want to keep learning with peers who are tackling these same challenges, Helios regularly shares conversations and insights that support HR leaders across K to 12.

This content is derived from a December 2024 conversation hosted by Helios. Follow Helios on LinkedIn for more insights on leadership and systemwide improvement.