School and District Leader Guide to Having Stay Conversations

It’s often said that it takes more time and energy to hire and recruit an excellent employee than it does to retain one, and this is especially true of teachers and principals.

When talented educators leave their schools, there’s a staggering cost. There’s a noticeable loss of knowledge, expertise, experiences, and ideas—all elements that are key to high-performing schools and ultimately, student achievement.

When talented educators leave their schools, there’s a staggering cost. There’s a noticeable loss of knowledge, expertise, experiences, and ideas—all elements that are key to high-performing schools and ultimately, student achievement.

As school and district leaders, you’re acutely aware of the ongoing teacher and staff retention challenges, whether it’s through your own experiences or the many data points that indicate retention continuing to be a concern in the future. Last year, the NEA reported that 55 percent of educators were thinking about leaving the profession earlier than planned—a number that increased to 59 percent for Latino educators and 62 percent for Black educators. And the concerns about the shortages aren’t subsiding, as teacher retention was front and center at last month’s SXSWEdu conference. 

When expert teachers and leaders depart for other opportunities, you might wonder, “what should/could have been done to get them to stay?” The answer is an action that’s low on effort, but with a big impact: having stay conversations early and often with teachers and staff members you don’t want to lose. These proactive conversations can help you understand what motivates them, what they’d like to see changed, and whether they’re considering moving on—and what might be done to reverse that decision. 

When done correctly, stay conversations can hold the key to high retention rates. Here’s more about what they are, what they aren’t, and why it’s not too late to have them. 

What stay conversations are

In stay conversations, the key word is intentionality. This applies to the timing of the discussions, who you choose to have the conversations with, and what’s said in those conversations. A typical stay interview takes place during the school year—not at year’s end. In fact, it’s good to think about them as a consistent practice, where you plan several “stay touchpoints” throughout the school year. 

Stay conversations aren’t conducted with all of your teachers. They’re specifically for the teachers and staff you deem irreplaceable.  

It might be tempting to say, “I don’t want to lose any of my teachers, so I’ll have conversations with all of them.” While this is an admirable goal, it’s not realistic. Stay conversations aren’t conducted with all of your teachers. They’re specifically for the teachers and staff you deem irreplaceable. 

While it might seem counterintuitive to only have these conversations with 20-30 percent of your teaching staff, there’s a reason. You want these conversations to feel special. As this Maricopa County School District HR leader says, it’s about “listening, responding, and elevating the voices of our best people.”

What stay conversations aren’t

It’s important to note that stay conversations aren’t meant to be punitive or negative in any way. Similarly, they’re also not tied to any conversations about performance or annual reviews. The goal is to build relationships with your teachers and staff, make sure they know their value to the school, and establish trust.

It’s important to note that stay conversations aren’t meant to be punitive or negative in any way. They’re also not tied to any conversations about performance or annual reviews. 

The intentionality around these discussions also means they shouldn’t be seen as a quick check-in, or the kind of informal chats you might have in the hallway. They require deliberate scheduling and planning. They're also different from exit interviews, with benefits and challenges alike.

Whether you’re looking to embark on a series of stay conversations for the first time, or want to improve your approach, here are a few insights that can help: 

Plan your conversations

First, consider where the conversations will take place. Opt for a convenient location that’s a neutral, private office or area—something other than your office, or the teacher’s classrooms. This ensures the teacher feels more at ease immediately. 

Second, do your research. Take the time to assemble informal or anecdotal notes about the teacher you’ll be meeting with—positive comments from other teachers, parents, or community members as well as your own experiences. 

The day of the meeting, frame the conversation in an informal way—that it’s a discussion about the reasons they stay at your school and that you want to understand how things are going for them and how you can best support them. If it’s appropriate, consider reinforcing the goal of the conversation through the context of your school’s shared vision and values. For example, if your school values center on topics of engagement, transparency, leadership development, and aspiration, bringing those into your stay conversations can make the discussions feel more in alignment.

Remember, stay conversations are always confidential. You’re looking for truthful and critical feedback, which means it’s crucial to create psychologically safe spaces—for both you and your teachers. 

Keep the focus on learning and information sharing

If intentionality is key in these discussions, so is learning. These conversations are an opportunity for you to invite an open dialogue, get feedback on what’s working and what’s not for the teacher, and understand if there’s a way to course correct or solve some of the challenges they’re sharing with you.

Here are a few questions to ensure you keep teacher and staff insights at the center of your conversations:

• What do you look forward to when you come to work every day?
• What do you feel would best enhance your school experience?
• What are some aspects of your role you’d like to see change?
• If you could change one thing about this school with the snap of your fingers, what would it be?
• What are some ways that I can support you better? 

Of course, all of these questions are a lead-in to the most important one: Do you plan to stay for next year? 

Ask what would make them stay—and follow-up with solutions

For your teachers who say they’re actively considering other options, ask outright what would convince them to stay. This might be a scary question, but it’s in these direct questions that you’ll garner the most valuable feedback.

With a few months left in the school year, it’s not too late to have stay discussions. They are low on effort but with a big impact.

As you’re collecting these answers, be truthful with yourself about what you can realistically change within your school or district. Keep in mind that asking for suggestions doesn’t mean you’re obligated to make any promises. If you’re not able to make the changes the teacher would like to see, be sure to remain transparent and in communication with them about what else might be possible. 

Either way, an essential part of the stay conversation is the follow-up. Consider if the script was flipped. How would it feel to be vulnerable with your leader about the changes you’d like to see, and never revisit the conversation again? It would most likely feel worse than not sharing the issues in the first place. You don’t want that for your best teachers. 

It’s never too late for a stay conversation

With a few months left in the school year, it’s not too late to have stay discussions. Your irreplaceable teachers and staff members might still be weighing their options—and it might surprise you to know that the most valuable action you can take to get them to stay is to have the conversation in the first place.