Having Hard Conversations

Hard conversations are an inherent part of school leadership. More often than not, as a principal or an assistant principal, you will engage in hard conversations, and you will need to do so in productive ways. Speaking with clarity and courage and addressing difficult situations both humanely and directly is a part of your day-to-day work.
Five questions to ask yourself before having hard conversations with faculty and staff can help you have useful and productive hard conversations with greater chances of success. These questions cannot be asked and answered within a short period of time, and some of the answers need collective action at your school. Yet, if you move toward making these questions more common and more considered, the chances of having hard conversations with positive results will increase.
These hard conversations go beyond speaking up when truly unsafe actions are taking place, such as drug or alcohol abuse, mental health issues, or anything that creates unsafe working conditions. These hard conversations focus on implementing strategic goals, curricular initiatives, teaching standards, job descriptions, and living out the norms of collaboration to foster a positive culture of learning and ensure the well-being of all who work at your school.
Question 1: Does your school have a culture of feedback, not only for the students, but also for the adults?
This type of culture creation isn’t a small ask. For a culture of feedback to take root, a strong foundation of psychological safety for all working in a school—a culture of belonging and inclusion for all—must be in place. With that culture as a strong base, your school can move to a culture of feedback that is positive, constructive, and possibly directive. As a result, teachers and staff can listen to feedback that may be difficult to hear with less defensiveness.
Ask yourself:
- Is there a culture of learning and unlearning for the adults in our school?
- Is there an emphasis on creating a culture of safety, belonging, and inclusion in our school for the adults as well as the students?
- Are we working on our collaborative skills and adult-to-adult communication in our school?
Question 2: Do you understand what it means to be a professional, and does that understanding include the capacity to both give and receive challenging feedback?
Our ability to communicate effectively and our willingness to engage respectfully with one another matter for the health of the school and the collective well-being of those within it. Yet educators mostly have credentials in how to teach specific grade levels and subject areas, and not how to communicate with each other effectively. Communicating effectively also includes the skill of giving and receiving feedback in healthy ways.
Speaking thoughtfully and listening without defensiveness is inextricably linked to the question below. School leaders must work on speaking up with respect, tact, and consideration, and listen to another’s perspective without experiencing emotional dysregulation.
Ask yourself:
- Do we have expectations about professionalism in our school?
- Do we have professional learning around how to give and receive feedback respectfully?
- Do we consider one another’s input to be welcome and helpful?
Question 3: Are you a model for receiving challenging feedback in a productive way?
In school, everyone is watching you, the school leader, to learn how to act, especially in challenging moments. Being the recipient of difficult feedback allows you to model a level of stress tolerance and an openness to another person’s point of view. In my book, Stretching Your Learning Edges: Growing (Up) at Work, I mention two skills that are essential for leaders: suspending certainty that your way isn’t always “the” way and building resiliency so that when moments of discomfort arise you manage them with professionalism and grace. Modeling these two skills for others when they offer you feedback is critical as you show that you too can be open to receiving input.
Ask yourself:
- What surprises me most when others have a different perspective on something and what is my response (both internally and externally) at those moments?
- How do I cope with unexpected chaos and high-anxiety situations?
- In moments of discomfort, can I continue to let in information? Can I make informed, nonreactive choices and keep myself centered?
- How do I soothe myself when I am dismissed, diminished, or challenged?
Questions 1–3, addressed earlier in this article, focus on creating a culture of continuous learning and modeling how to receive difficult feedback. The next two questions dig into the nuances of a hard conversation now at hand.

Question 4: Have you had a clarifying conversation before a hard conversation?
It is much better to have clarity before you have accountability. As author Blaine Lee writes, “Almost all conflict is a result of violated expectations.” Remember to be clear with your message. What do you expect from others? How do you know that those with whom you want to have a hard conversation have clarity about what to do and to say? If you know for a fact that the expectations are clear, that the individuals implementing the actions understand what to do and the supports to do it, then it is much easier to have an accountability conversation. You are standing on more solid ground.
Ask yourself:
- Have the expectations been made clear—verbally and in writing?
- How actionable are those expectations? Are they written in vague ways that could be easily misunderstood? (For example, “timely” or “respectful” can be interpreted in a variety of ways.)
- Have those implementing the expectations been given the skills and supports to do the work?
That last question is truly about the conversation itself and is a critical one that some forget to ask or are frustrated by having to ask.
Question 5: Do you have an action plan thought out? Do you know what you want to see instead of what you are seeing now?
Many administrators find the question above quite irritating. “Didn’t we hire an adult with a credential who should just know how to do it or get on with it?” they might say. My question at this stage is, “Do you want to be right or effective?” What are the “look fors” and “sounds likes” for the actions you want the person to take? Getting some specifics will get you much closer to the outcome you are hoping for than if you stay vague and unclear.
Ask yourself:
- Do you have a plan for the individual you want to talk to that includes actions and behaviors they could take to be successful?
- Do you know what supports or assistance you could provide that will help the person take those actions?
- Is the action you are proposing doable for this individual? If not, what would be doable?
I am often asked the following questions in my workshops: Do I send an email about meeting me in my office or should I meet them in their classroom? What time of day or what day of the week should I do this? How do I start the conversation, so I am sincere but do so with authority? These aren’t bad questions to ask. They are just not the first questions to ask. Ask them but ask them after the five questions above.
Hard conversations are never not hard. They will, for the most part, be awkward and uncomfortable, and will require participation in experiences you would rather avoid. And if what you are seeing is educationally unsound, physically unsafe, or emotionally damaging for those in your school, you must speak up. The questions above can help you do so with a greater chance of success. Your students
are watching.
References
Abrams, J. (2021). Stretching your learning edges: Growing (up) at work. MiraVia.
Lee, B. (1998). The power principle: Influence with honor. Free Press.
Jennifer Abrams is a communications consultant who works with adults in K–12 schools worldwide. She is the author of Having Hard Conversations, among many other publications. She will speak at UNITED in July.