She was half a block ahead of me, walking along the winding stretch of Hobart Street to school. Should I continue at my normal pace? That would mean catching up to her, and I would feel awkward or rude just passing her by with a “Good morning.” If I walked alongside her, what would I chat about? The alternative, the safer route, would be slowing down and staying a safe distance behind.

This scenario played itself out on many mornings during the years I studied in Pittsburgh when Mrs. Keny Deren was my principal. When I did have the courage to talk to her, I was never disappointed. There was always something to share, to laugh at, to brighten the day. But even those times when I was too bashful, there was a certain poise and grace to learn from the dignified manner in which she carried herself. Mrs. Deren touched so many of us through her warm and personal interactions. She served as a true role model.

Before leaving home to study in Pittsburgh for seventh Should I continue at my normal pace?grade, I knew Mrs. Deren was my mother’s mashpia (mentor). That said a lot! My mother, of blessed memory, was also a principal, and sought Mrs. Deren’s advice for all types of complex situations that she dealt with. I knew if my mother thought highly of someone, she must be really special.

The Rebbe wanted all of us to seek mashpi’im, objective spiritual mentors, to consult with on all important matters, based on an imperative from Ethics of Our Fathers: “Acquire for yourself a rav (spiritual mentor).”1 The Rebbe asked, “How do you know how to choose a qualified mentor? The Talmud teaches us what to look for: the mentor must be ‘like an angel of G‑d.’”2 What a tall order, considering that we have never seen angels! Yet this is a very real and practical directive. Anticipating this obvious conundrum, the Rebbe cited Maimonides, a codifier of Jewish law who details exactly how to fulfill every aspect of Jewish practice.

Interestingly, Maimonides says that in the time of Moshiach, people will resemble angels, in that they will be free of envy, rivalry, hate, etc. He explains that a person who resembles an angel of G‑d naturally exhibits what our sages describe as the three primary identifying signs of a Jew: modesty, compassion and kindness.3 So, if a mentor is to be like an angel, he or she should demonstrate these three qualities.

Mrs. Deren certainly fit the bill; I know she had those traits, because I got to observe them firsthand.

One of the first things that struck me about Mrs. Deren was her warmth and disarming smile. She had this ability to instantly connect with you and make you feel comfortable. She was genuinely happy for your happiness, and pained sensing your hardships. She expressed her love with frequent, heartfelt complimentsShe expressed her love with frequent, heartfelt compliments, often lifting your chin or touching your cheek like a proud mother. Her praises were not preplanned and thought out; rather, she said them as if she couldn’t hold them back and she just had to share. She could make you feel like a million dollars, appreciating you for just being you. It was obvious that she had a special place in her heart for every student and appreciated each unique personality. She also had a fantastic rapport with our teachers; it was evident that they held her in high regard and valued her opinion.

She related to everyone as an individual, regardless of age, status or accomplishment. She showed respect to everyone, and expected the same of her students. If there was one thing that she abhorred, it was when people behaved disrespectfully. She expected us to feel proud to be Jews and chassidim, and to reflect that in our conduct. That included keeping our classrooms tidy and being mindful to pick up any stray candy wrapper or tissue left on the floor. She didn’t even need to verbally instruct us; her very presence conveyed these messages to us. As her students, we rose to her expectations because no one wanted to disappoint her.

When it came time to plan my birthday gathering, or farbrengen, I was very idealistic, and wanted someone very inspirational to speak at the gathering. I thought Mrs. Deren would be perfect, and knew she wouldn’t refuse me, especially after she mentioned that I shared the same birthday as her beloved father, Rabbi Sholom Posner, of blessed memory. I told her that what I really wanted was for her to tell us what our goals should be and how to get there. With a great smile, she immediately responded that she would be delighted to speak, but would need to have a face-to-face meeting to discuss the topic further. During the next few days she was very busy, and apologized that she had to keep pushing off “our discussion” because of unexpected meetings. I figured that it wasn’t a good time, and I didn’t want to bother her, so I let it go.

But she had not forgotten. She called me the day before my birthday and told me how awful she felt, and that she decided that she wanted to host the whole high school for a birthday supper at her home, if I was comfortable with that. I called my mother in a panic—no, I definitely would not feel comfortable with her going all out like that! So, in the end, we decided that

Mrs. Deren & her husband
Mrs. Deren & her husband
I would have the party in school, and afterward we would go to Mrs. Deren’s home for her words of inspiration.

I was very eager and anxious to hear what she would say. My mind spun with very idealistic thoughts and burning questions on how to achieve various religious aspirations. What happened really surprised me. Mrs. Deren’s speech turned out to be about my name. She expounded on the lessons we learn from each of the letters, their form, and the associations made with their numerical value. She then shared stories about her father, Rabbi Posner, and his unique relationship with the Rebbe. She wanted to give us a sense of how treasured chassidim are to the Rebbe. She not only opened her home and inspired us, but took the extra time to prepare something personalized for me.

A few days later, she took me aside and told me she remembered some powerful stories she should have mentioned at our gathering. She recounted them with such description, animated feeling and passion that her face lit up.I felt so honored to have been singled out for this private time I felt so honored to have been singled out for this private time with Mrs. Deren.

A short while later, a student approached Mrs. Deren with a concern. She had become very enthralled with materials produced by Breslov chassidim—specifically, their approach to prayer. She felt that we needed to reflect before prayer, rather than just launching into the prayers without setting the proper tone. Mrs. Deren agreed that the chassidic approach required some reflection, and she decided that each morning would commence with a dvar Torah, some inspirational teaching. Before long, Mrs. Deren gave me the assignment to stand up in front of the assembled high school every morning and share a Torah thought; then we would pray.

One morning, before leaving to school, I got a call on my private phone line and was shocked to hear it was Mrs. Deren. She was calling to tell me that she would be arriving late that morning and would miss my dvar Torah. Would I please write it down for her and bring it to the office so that she could read it later? I was very taken aback. I had never realized that Mrs. Deren was actually listening in to what I had to say. The fact that she enjoyed my little dvar Torahs meant so much to me, and spoke of her sincere openness to learn from anyone.

She would sometimes give us compliments that left such an impression on me that I recorded them in my diary. For example, I observed her telling a classmate, “Ali, you are such a pleasure! May you have students that give you as much pleasure as I have from you . . . but remember, that’s a double-edged sword.” She once told me, “Esther, I see a world in you.” She was such a natural educator, empowering and building people up, because that is what she saw: their traits, their talents, their potential, and where that could lead.

At the end of eighth grade, our class was informed that due to health issues, Mrs. Deren would not be able to attend our graduation ceremony. However, she arranged a meeting with our class to congratulate us and wish us well. Believe it or not, years later, when I was reminiscing with other classmates, I discovered that for the longest time many of them actually held on to a plastic l’chaim cup, candy wrapper, or even a napkin from that meeting! They cherished these items for the sentimental value they contained, a memory of the blessings and well-wishes of such a beloved principal at an important time in our lives.

She remains, in my mind, the example of an ideal principal and educator—a true leader who inspires and empowers others. I feel so privileged to have known her, to have been a recipient of her kindness and compassion, and a witness to her modesty and humility. She truly met the criteria for “resembling an angel of G‑d.”

When I think of her, I know she’s miles ahead of me in stature and refinement. I feel more comfortable thinking of her far beyond reach. But having known her, I feel challenged to walk alongside her, to emulate her in some small way, knowing those steps will only enrich my life.