What I Wish I Knew: The Real Cost of Avoiding Difficult Conversations

From a former superintendent, stepping back (not stepping out), offering a view from just beyond the desk.

Let me start with a little honesty, when I first stepped into district leadership, I thought the hard conversations were now someone else’s problem. I figured I had left that behind, it was for supervisors and site administrators to handle, right? My job was to focus on the big picture: strategic planning, board member relationships, district-wide systems, and community partnerships. Meanwhile, the heavy lifting with difficult employees? That was for everyone else.

Well… that thinking didn’t last long.

The truth is, the higher up you go, the harder the conversations become, and the more crucial it is that you model how to do them well. What surprised me even more? I wasn’t just responsible for continuing to have the tough conversations; I had to develop those skills in my leaders as well. If your leaders aren’t equipped to hold staff accountable with clarity and compassion, the school culture suffers, and ultimately, so do the kids.

Silence Isn’t Neutral, It’s Expensive

Avoiding tough conversations might feel like you’re keeping the peace, but what you’re really doing is promoting dysfunction. When leaders don’t address performance concerns or unprofessional behavior, the rest of the team takes notice. Your high-performers, who are already stretched thin, start asking why they’re working so hard in a culture where mediocrity goes unchecked. And in today’s climate, that risk is amplified.

We are in the middle of a national teacher shortage. According to the U.S. Department of Education’s 2025 interactive Teacher Shortage Areas report, nearly every state continues to face critical teaching gaps, with rural and high-needs schools hit hardest. Attracting and retaining strong educators isn’t just a strategic priority, it’s a survival skill.

When we allow poor performance to persist because we’re uncomfortable having hard conversations, we create a workplace where top talent doesn’t feel valued or protected. And those educators likely won’t stick around. They shouldn’t stick around. There are too many other options for them that offer more supportive environments, growth opportunities, and less stress.

The financial and human cost of turnover is staggering: recruitment expenses, onboarding, lost instructional time, and the erosion of community trust. According to Learning Policy Institute estimates, the cost to replace a single teacher ranges from $11,000 to $25,000, yikes!

“Culture is not built by what you preach. It’s built by what you tolerate.”

Every time we avoid a conversation we know we should have, we silently endorse the behavior. In a staffing crisis, we can’t afford that kind of ambiguity. We need every employee, every educator, para, specialist, and administrator, moving in the same direction, held to the same standard.

So yes, silence may feel like the safe route. But in reality, it’s the most costly of all.

You Can’t Lead What You Don’t Practice

Let’s talk about the conversations we all dread, the ones that keep you pacing in your office, rehearsing your lines like it’s opening night on Broadway.

They’re uncomfortable. They’re high-stakes. And yes, they might not go the way you hope.

But here’s the bottom line: you can’t build a culture of accountability if you’re unwilling to model it. You can’t coach others through hard conversations if you haven’t done the hard work yourself. Staff are watching, not just what you say, but what you do when something isn’t working.

Do you lean in? Or do you let it slide?

Here are some things that I found most helpful:

• Start with clarity. Don’t dance around it. People deserve to know where they stand.

• Be human, but be direct. Kindness and honesty aren’t opposites.

• Use a framework. A clear structure helps you stay focused when emotions run high.

• Reflect and adjust. No two conversations are the same. Learn from each one.

If you’re waiting to get more comfortable with difficult conversations before you start having them, let me save you some time: that day never comes. You don’t become a stronger leader by avoiding friction, you become one by moving through it. And the more you practice, the less paralyzing it becomes.

Because at the end of the day, the question isn’t whether your team will face tough moments. They will. The real question is, will your team have leaders who know how to walk through those moments with courage, clarity, and care?

When it Really Clicked

One of my administrators walked into my office one day looking like a dog who had just chased a squirrel through rush hour traffic. He sat down, let out a long sigh, and said, “I think one of my teachers is testing how far they can push before I quit to drive the local ice cream truck.”

I chuckled, until I realized he wasn’t joking.

This was a strong leader, thoughtful, steady, not easily rattled. But he was stuck. He had a veteran teacher on his team who had checked out, was resisting feedback, undermining staff norms, and quietly dragging down the culture. He’d tried every supportive measure we preached short of an interpretive dance and a bullhorn: coaching, modeling, mentoring. Nothing stuck. His staff saw it. And so did I, it was time for the tough conversation.

That moment stuck with me, not just because of the situation, but because of what it revealed: I hadn’t done enough to build his confidence or skill in tackling this head-on. He didn’t need me to fix it. He needed me to back him up, coach him through it, and make it crystal clear that courageous conversations weren’t optional, they were an essential part of the job.

We didn’t fix the problem that day, but we did start shaping what accountability needed to look like, not just in his building, but across the system.

Final Word (for Now)

Taking a step back from the K-12 day-to-day has given me perspective I didn’t always have when I was running at full speed. Difficult conversations, clear expectations, and consistent follow-through aren’t “extra” duties; they are core components of strong leadership.

Whether you’re brand new to district/school leadership or just recognizing there’s room to grow, be intentional. Start building your capacity now. Lead with clarity, practice with consistency, and design systems where accountability and trust are the norm, not the exception.

The culture you want tomorrow starts with the conversations you’re willing to have today.

Related Readings and Resources

U.S. Department of Education (2025). Teacher Shortage Areas, https://www.ed.gov/teaching-and-administration/professional-development/teacher-shortage-areas 

— Details state-designated shortage zones across the country, underscoring the ongoing national teacher crisis.   

Learning Policy Institute (September 2024). 2024 Update: What’s the Cost of Teacher Turnover? (Interactive Tool & Technical Supplement), https://learningpolicyinstitute.org/product/2024-whats-cost-teacher-turnover 

— Offers updated per-teacher turnover cost estimates ($11,860–$24,930) and outlines the fiscal impact of teacher attrition.  

New York State School Boards Association (2025). Exploring the Financial Impact of Teacher Turnover, https://www.nyssba.org/news/2025/01/10/on-board-online-january-13-2025/exploring-the-financial-impact-of-teacher-turnover 

— Summarizes costs and identifies turnover as a central driver of the teacher shortage.  

National Center for Education Statistics (2023). Report on the Condition of Education, https://nces.ed.gov/pubs2024/2024144.pdf 

— Confirms that 86% of U.S. public schools faced hiring challenges in 2023–24, especially for special education, science, and support roles.   

Tracey Salamondra (2021). Effective Communication in Schools. BU Journal of Graduate Studies in Education, 13(1)., https://files.eric.ed.gov/fulltext/EJ1303981.pdf 

— Emphasizes trust, transparency, and active listening—fundamental to successful difficult conversations.  

Elevate Educator, Managing Conflict: A Guide to Difficult Conversations, Journal of Educational Administration (2024), https://www.elevateeducator.com/post/managing-conflict-a-guide-to-difficult-conversations 

— Demonstrates that proactive conflict resolution by school leaders enhances cohesion, while avoidance erodes morale.