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This article first appeared in Phi Delta Kappan, the professional magazine of PDK International. Republished with permission.


By: Maury Grebenau


When I was looking for my first senior administrative position, having difficult conversations was my biggest fear. I clearly remember when I recognized this as a growth area. When I was an associate principal, we had a student in our high school whose parents were going through a messy divorce. Arguments about custody and poor communication between the parents resulted in the boy waiting after school for hours to be picked up one day. When I reported the situation to the head of school, he told me to call the father and let him know we would not allow his son back into school without a monthlong schedule of who would be picking his son up every day.


I was so shocked at being asked to do this, given my minimal administrative responsibilities, that I just left his office without asking to be relieved of this duty. After finally mustering the courage to call, I stuttered out the news to the child’s father. I could hear the anger in his voice as he thundered, “Do you mean to tell me that you aren’t going to let my son back into school until we get you a schedule of who is picking him up for the next month?!” A number of answers flew through my head, including, “It’s not me, it’s the head of school!” I also considered just hanging up and blaming a bad connection. Instead, I just said “yes” and was shocked when he said “OK” and then hung up.


My journey from someone terrified to deliver any difficult news to a successful principal who was comfortable having hard conversations was punctuated by several key shifts in my thinking.




The initial shift in mindset was to recast tense situations as growth opportunities that would help me achieve my goals. Brene Brown’s writings were a significant force in helping me turn this corner. Brown’s research (2012, 2018) shows that the fear of vulnerability is a significant roadblock to more meaningful dialogue. I recognized this fear was one of the reasons I was so worried about having hard conversations. I had to take ownership over these situations and be more comfortable dealing with them. Rather than spending my time worried that people were upset with me or endlessly imagining how I would respond to all the emotion angry people would bring to the room, I needed to learn how to engage with upset people.


In my first year as a principal, I had a situation where I needed to say a kind but firm “no” to a very angry parent. She yelled and screamed, but I kept my calm and told her that I wasn’t going to tell her I would do something I wasn’t intending to do. She ended the conversation by apologizing for yelling, saying, “That’s just always how things got done here.” My willingness to engage and be honest with her, even though I knew it would upset her, gave everyone clarity about what would happen next. My direct engagement meant I was seen as responsive (although perhaps also unreasonable).


This lesson had external and internal aspects. Externally, I realized that embracing the conversation would be better for those involved, and also for my own position as a leader. Internally, I recognized that I needed to stop letting fear drive my leadership style. The only way to get better at having hard conversations was to have hard conversations.




My second significant shift occurred after having lots of hard conversations as a new leader. I was confronting issues head-on and no longer avoiding hard conversations. However, often I was seen as unreasonable or difficult. Some people felt frustrated because they believed I had already made my decision and that meeting with me was a “waste of time.” I needed to reassess my goal of these hard conversations. The goal of the conversation should not be to convince the other party of my own perspective but rather to make sure I understand their position.


The seeds of this realization were planted when I was starting a cohort program supporting early administrators. In the initial launch of the program, each of us sat with the presenter who acted out a hypothetical scenario that required a hard conversation with a teacher who had disrupted a meeting we were running. He recorded each of us having this conversation and then used clips from the videos to introduce his presentation. Only one of the 40 or so people in the program tried to find out why the teacher had disrupted the meeting. Everyone else spent the time giving clear explanations about what behavior they expected in the future and why. The presenter noted how much more successful the conversation was when the administrator learned what was motivating the teacher.


This powerful lesson is echoed in the work of Barry Jentz (2007), a Harvard professor who researched communication barriers. Drawing a distinction between reflexive and reflective conversations, Jentz encourages us to try to understand others’ positions (reflective), rather than trying to fix them (reflexive). When we can figure out where people are coming from, we have a much greater chance of moving forward even when things seem stuck.


In one of my first parent meetings as a principal, I met with a very upset parent who did not want to reenroll her children without a special contract with the school that dictated several obligations the school would commit to. All her requests had to do with things the school had failed to do before I got there. After she had laid out everything, I said, “it sounds like you really have lost trust in the school.” She became visibly excited and shouted, “yes, that’s it. I don’t trust the school!” After that moment, she became much more open, and we were able to discuss the issues at the root of her concerns and what we could do about them. She enrolled her children without a special contract. The power of feeling understood completely changed the dynamics of the conversation.


I put this learning into practice by opening conversations with an invitation to the other party to tell me more about the situation and what is upsetting them. I listen carefully, take notes, and rephrase what I believe I have heard. Only when it’s clear that I understand do I begin to explain my position. High emotion is often a sign that we need to listen more. If someone becomes agitated or upset, I need to go back to listening to understand what is happening before I try to help them understand anything else.




The final mindset shift for me was in how I approached these conversations in general. I had learned how to have productive conversations, but I still saw these conversations as necessary evils and sought to avoid them if possible. I recently had a coaching session with a newer administrator who described something that echoed this stage in my own journey. When this administrator received an angry email from a parent, he and his supervisor would spend time drafting and tweaking the right response. I used to do the same. But I believe this approach stemmed from my hoping that the right combination of words and phrases in an email would allow me to avoid the challenging conversation. I asked the administrator: “When you send off this email, does it ever work?” The sheepish grin in response was all the answer I needed.


I’ve learned that the best (and most efficient) way to deal with a situation is to pick up the phone and make a call or schedule an in-person meeting. Instead of viewing the challenging conversation as something that potentially would break connection and damage the relationship, I see it as an opportunity to deepen the relationship.


When the Harvard Negotiation Project (Stone, Patton & Heen, 1999) analyzed challenging conversations and why they rarely end in positive resolution, they found that two layers of conversation are happening below the surface: the feelings conversation and the identity conversation. Strong feelings and self-doubt frequently fuel angry words, and these feelings are more consequential than the particular discussion topic. Surface-level conversations rarely go anywhere because the emotions are rooted in the deepest level of how people see and define themselves. The conversation fails to address this. This revelation helped me to understand that most of the success I experienced in earlier conversations came from probing deeper into what was really upsetting people. When I was able to surface those issues, I could then help address them.


I had gotten to a point where I could have the tougher conversations with the parents who were “reasonable,” but I was avoiding the ones who were “on my list” of difficult and unreasonable people. I realized that the “difficult” parents were concerned about deeper issues that we had not successfully surfaced. I didn’t understand them at this deeper level, so I wasn’t hearing them, and we could not move past their anger. I started proactively contacting some of my tougher parents to check in regularly instead of waiting for an angry email or call from them. Moving into a proactive space before the inevitable rough patch would emerge opened a pathway to communicate before things set them off. Cultivating a deeper connection and understanding of what was important to them helped me to better navigate the harder conversations when they arose.




In my current role, I coach school leaders as they navigate their own road to having hard conversations. We unpack the many roadblocks that keep us from engaging in this hard, but critical, work. Every school leader needs to develop this skill, and pretty much everyone finds it challenging. My hope is that capturing my own path may help others who are stuck on the road to move forward as well.




Brown, B. (2012). Daring greatly. Avery.

Brown, B. (2018). Dare to lead. Random House.

Jentz, B. (2007). Talk sense: Communicating to lead and learn. Research for Better Teaching.

Stone, D., Patton, B., & Heen, S. (1999). Difficult conversations. Penguin.

This article appears in the May 2024 issue of Kappan, Vol. 105, No. 8, p. 58-59.

Judith Talesnick

Program Consultant

Lisa Peloquin

Senior Instructional Designer and Coach

Lisa Peloquin is a Senior Instructional Designer and Coach at JNTP, where she focuses on content development and materials preparation for JNTP’s Early Childhood and Administrator Support Programs.. Lisa holds a B.A. in Psychology, with a concentration in child development, from Penn State and a Masters in Education from the University of Illinois at Chicago. She is currently working on her Ph.D. in community psychology, with a research interest in understanding how school communities can impact educational equity. Lisa can be reached at

Tavi Koslowe

Program Consultant

Rabbi Tavi Koslowe is a Program Consultant at JNTP, where he provides coaching to early career administrators through the Administrator Support Program. Tavi has been a teacher and educational leader for the last twenty years in lower, middle, and high school settings. He is currently serving as the High School Dean at the Leffell School in Westchester, NY and the co-director of The Idea Institute, where he supports teachers, administrators, and school leaders in furthering educational practice in Project Based Learning. Most recently, Tavi served as the Judaic Studies Principal of The Idea School in Tenafly, NJ and has held other school leadership positions at the Ramaz School in Manhattan, NY and Yeshivat Noam in Paramus, NJ. Tavi participated in JNTP’s Teacher Induction and Administrator Support Programs. He can be reached at

Eva Broder

Program Consultant

Eva is a Program Consultant for JNTP, where she facilitates professional development training for early childhood mentors. Eva has served as a teacher in private schools throughout the NY area for over 15 years. During this time, she has provided support as a teacher mentor, working with individuals and groups to enhance their teaching practice, and has facilitated and trained teachers in the use of Professional Learning Communities. Eva currently works as a School Consultant for Professional Development at the Hebrew Academy of Long Beach (HALB). She holds a B.A. in Psychology from Yeshiva University and an M.S. in Special and General Education from Bank Street College. Eva trained as a mentor with JNTP in 2017-18. She can be reached at

Evan Weiner

Associate Program Consultant

Evan Weiner is an Associate Program Consultant at JNTP, where he facilitates mentor training. He has been involved with Jewish Education for over 20 years. Evan began his connection with JNTP as a new teacher and eventually became a mentor himself, mentoring teachers in both General and Judaic Studies departments. He has been an educational leader in both formal and informal educational settings, and has brought his JNTP training to elicit the best in his staff partners. Most recently, Evan served as Judaic Studies Principal, Curriculum Coordinator, and Instructional Coach at Ohr Chadash Academy in Baltimore before joining the JNTP staff. Evan participated in the YOU Lead Educational Leadership Program and JETSIsrael Edtech Incubator Program, and he holds an M.Ed. from Azrieli School of Education. Evan can be reached at

Rachel R. Harari

Associate Program Consultant

Rachel Harari is an Associate Program Consultant at JNTP, where she co-facilitates new teacher training. She is also an Associate Lecturer at Columbia University and a middle school English Language Arts teacher at Yeshivah of Flatbush. Rachel is currently working on her PhD at Teachers College, Columbia University, within their Educational Leadership program. Through her work as a Department Chair for six years at Magen David Yeshivah High School in Brooklyn, New York, Rachel was inspired to study the role of the high school department chair in Modern Orthodox schools in New York City. Rachel received her M.S. in Special Education from Brooklyn College, and her B.S. in English Education from New York University, where she published her research on mathematics anxiety in elementary school students: “Mathematics Anxiety in Young Children: An Exploratory Study.” Rachel is a 2016 recipient of The Covenant Foundation’s Pomegranate Prize, which recognizes emerging leaders in the field of Jewish Education.

Lauren Katz

Director of Development

Lauren Katz is JNTP’s Director of Development, where she oversees the organization’s fundraising efforts and marketing and communications initiatives in an effort to advance JNTP’s mission and strategic goals. Lauren’s portfolio includes strategic planning, donor cultivation, engagement, and gift acquisition. She has an extensive background in Jewish non-profit management with a specific focus on fundraising and development, most recently serving as the Director of Marketing & Communications and Alumni Relations at SAR High School for over four years and at the Ramaz School for seven years as the Director of Alumni Relations. In addition, Lauren worked at the Jewish Federation of Metropolitan Detroit and UJA-Federation of MetroWest, NJ in the campaign and planning and allocations departments. Lauren holds a B.A. in Political Science from the University of Michigan and attended the University of Michigan School of Social Work and Jewish Communal Leadership Program. Lauren can be reached at