An Interview With Pirie Jones Grossman

This interview was originally published in Authority Magazine and can be found here:

More authentic relationships — By getting to know my team well, I’m able to show my care and compassion in ways that help my team develop and grow. Additionally, these relationships have bloomed beyond the work roles and into real friendships. I’m close with my business partner, the folks on our team and I take a genuine interest in the success and happiness of each of them without judgment. Additionally, I know that these relationships are reciprocated and I need anything in the future, these are all people I know I can rely on.

Starr Sackstein

Intoday’s dynamic world, the concept of leadership is continuously evolving. While traditional leadership models have often been male-dominated, there is a growing recognition of the unique strengths and perspectives that women bring to these roles. This series aims to explore how women can become more effective leaders by authentically embracing their femininity and innate strengths, rather than conforming to traditional male leadership styles. In this series, we are talking to successful women leaders, coaches, authors, and experts who can provide insights and personal stories on how embracing their inherent feminine qualities has enhanced their leadership abilities. As part of this series, we had the pleasure of interviewing Starr Sackstein.

Starr Sackstein is an accomplished educator, author, and advocate, dedicated to transforming education through innovative practices. With a background in secondary education, she has championed student-centered learning, assessment reform, and technology integration. As an author of several influential books, including “Hacking Assessment,” Starr empowers educators globally with practical strategies for creating learner-driven classrooms. Her insights, shared through speaking engagements, workshops, and online platforms, inspire educators to reimagine traditional teaching paradigms. Starr’s commitment to fostering critical thinking, growth, and equity underscores her role as a thought leader shaping the future of education.

Thank you so much for joining us in this interview series. Before we dive into our discussion about authentic, feminine leadership, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I was a high school English and journalism teacher in New York for 16 years. It was in the classroom that I started developing my leadership skills and innovating with my students which became the work I do now. Working with colleagues and students with empathy and curiosity, taught me that you get more from leading this way than with fear and tyranny. Teenagers are notoriously good at spotting inauthenticity and pointing it out. After working in the classroom for the majority of my career, I was a school district curriculum leader for a few years where I had a bigger, district-wide team before moving into a private consulting company and publishing company for a few years where I worked with a smaller team, helping produce books and learning experiences for our clients. It was this last opportunity that led me to Mastery Portfolio, where I am currently the COO, which leads the team that works directly with schools and districts. Honing my skills as an educator made me the leader I am now.

Can you share the most interesting story that happened to you since you started your career?

Being an educator and working with children inherently creates amazing stories. One interesting story is when I was honored by the Dow Jones for my work as a journalism advisor. My students were unable to attend the award ceremony with me, but they wanted me to know they were with me in spirit. They planned and organized and came to class the day before I was leaving for the conference dressed in tee shirts that said “Team Sackstein” (see below). I was so overwhelmed by their kindness, that it took everything I had not to cry. It is such a privilege to work with young people; in many ways, being a good teacher is just like being a leader. I always led with my heart; that’s what made me memorable.

What do you think makes your company stand out? Can you share a story?

As a company, Mastery Portfolio does a phenomenal job serving the schools we work with and the educators we support. We work diligently to ensure that every school’s needs are known and met in a timely and comprehensive way and our responsiveness to the challenges teachers face is always appreciated. Our team works closely with the schools and can make their lives easier. One school we work with has had much success and we were able to help them develop their mastery scale and their competencies and our tool made it easier for their students to take ownership of their learning. Additionally, the level of expertise in the area of instruction and assessment is second to none.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Being a good listener is essential to being a good leader. Sometimes you have to hear the things that aren’t being said and capitalize on the strengths that your team brings to the table. Being a good listener helps me build good relationships, making it easier for me to know the best people for different jobs. Another essential quality is self-awareness; knowing my strengths but being humble about them. For a team to be successful, you have to capitalize on each person’s contribution, and knowing when to share my own experience and expertise versus allowing someone else to shine helps my team thrive. People need to feel valued and validated for a team to be functional and successful. This is also helpful when mistakes are made and I own them honestly and apologize promptly. And lastly, my curiosity keeps me assuming positive intent while I continue to learn and grow as well. To be a good leader, you have to be a learner first, and being curious keeps me in that mindset.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Difficult decisions are a regular part of being a leader. Ensuring that our team doesn’t feel the weight of the challenges that don’t pertain to them, while at the same time being transparent when input is needed is important. As a small Edtech company, we’ve made a lot of hard decisions as we’ve grown over the years. Choosing the right path requires weighing as many foreseen outcomes as possible, anticipating as many challenges, and then seeing what serves the mission best and going with that. While I was in school leadership, this applied to how I ran my team. In my current position, we collaboratively make decisions. Over the years, we have had to decide to let go of good people whom we just couldn’t afford to keep or who weren’t a good fit. Deciding to let go of a person we care about is never easy, but it is necessary sometimes. Additionally, we’ve had to let go of clients because they weren’t a good fit. Since our mission is so important to us, we work with a set of nonnegotiables that keep us focused on what matters and also help us govern how best to run the company. If we work with a school that doesn’t understand or align with the mission, we’d rather let that client go than continue to counsel them against our better judgment.

I can provide a specific example of when I first decided to leave the classroom. This decision was very challenging for me as I loved teaching high school students and never thought I’d go into leadership. I had to make the hard decision because it was time to leave the school I had been at for almost a decade and my son was experiencing panic attacks which made it hard to get him out of the house. Since I worked so far from home, it was often left to my neighbor to get him off and when that became a burden I missed a lot of school. I knew I had to get a job closer to home and I saw the perfect opportunity. Although I wasn’t fully credentialed, I knew I would make an excellent curriculum director and applied on a whim. Needless to say, I got that job and was able to help my son and although I miss the classroom and formal instructional coaching, I made the right decision for my family and my career as this pushed me further along my path. Being a mom and a leader, I can empathize with my team.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a personal experience where embracing your unique leadership style, which might not align with traditional expectations, led to a significant positive impact in your organization or team?

I’m a lead-from-the-middle kind of woman — I like to get my hands dirty with my team and tend to be very informal. My informality has caused challenges in the past — for example, I don’t believe that I have to look a certain way to be effective at my work. I prefer to be comfortable and not dressed in business attire. Instead of trying to be who everyone else wants me to be, I lead authentically and transparently. My team and the folks I work with outside of my organization, see me as a member of the team, not the leader necessarily. And because of this stance, there is a level of trust that allows folks to take big risks that almost always pay off. The other side effect is that the team feels responsible for the win. This is important. Anytime something good happens, it is a win for the team and not for me. There is a lot of room in the world for all of us to be successful and I believe we need to lift each other — especially woman to woman. As a consultant, I work from behind the scenes with leadership, so their wins come from them and not an outsider. In our organization, a win for our team is a win for me. I work hard to leave my ego out of it.

In your journey as a leader, how have you balanced demonstrating resilience, often seen as a masculine trait, with showing vulnerability, which is equally powerful, but typically feminine? Can you give an example where this balance created a meaningful difference?

I don’t see being resilient as a masculine trait or vulnerability as feminine. Resilience is a necessary trait as a leader because it is inevitable that some choices won’t work out the way you plan. It is also inevitable that mistakes will be made and being able to move forward after they are is essential for the growth and success of a person and a team. Once while working with a rather large school network, I made a rather large blunder when all of the staff (much larger than my tech could allow) were invited to take a needs assessment which is something our company is known for. I went over my slide decks, planned with their leadership and on the day of, not only did I inadequately present some questions because I didn’t go over the language specifically with leadership, but many of the folks couldn’t log in because I didn’t realize that our zoom account couldn’t accommodate more than 500 people. There were many problems that precipitated because of this gaff and I knew I was in the wrong. There was a lot going on in my personal life at the time; my father was sick, my grandmother was in the hospital and I didn’t want to admit that I wasn’t in a good place. So rather than asking for help, I watched as my efforts went up in flames. To rectify the situation, I was in touch with the woman in charge of their team there and I first apologized for being ill prepared and vulnerably admitted what was going on. She was understanding, but I had one more important, humbling experience to endure. A call was planned with higher leadership and my partner had to get involved too. We made an action plan to ensure that this kind of mistake never happened again. They were gracious and I brought my A-game for the rest of the year. Fortunately, I was able to demonstrate my competence and expertise and we still have them as a client. It never feels good to admit publicly when you’ve made a significant mistake, but usually when you do, the likelihood for grace is better. I’m grateful that this client gave me grace in this situation and kept faith that I was capable of delivering what they paid for.

As a woman in leadership, how have you navigated and challenged gender stereotypes, especially in situations where traditional male-dominated approaches are the norm? What strategies have you employed to remain authentic to your style?

I am capable of hanging with the men and they don’t intimidate me. Although I have found that many men struggle with strong women. Because of who I am, I can’t help but live in my authentic self which means I need to speak up when I don’t agree and I won’t be silenced. In my leadership role in a school district, there were many who wanted to silence me and the men were dominant in that capacity. Rather than allowing them to bully me into submission, I spoke up repeatedly, got yelled at a few times publicly and also made the ethical decision to leave when I felt that I couldn’t be effective in the organization in the way they expected me to behave. Because I made the decision to stay within my authentic self, more opportunities came my way where my leadership style was not just appreciated, but respected. Although compromise is necessary in some instances, at the end of the day, having clear boundaries about what can be compromised and what cannot is so important. If I would have stayed in that position, rendered a puppet for initiatives and behaviors I couldn’t get behind, I would have had to live with myself which is something I couldn’t have abided. It was a bad fit — sometimes that happens. My big takeaways here are you have to know yourself — the good and the bad and find a space where all of those things are mutually beneficial. While all of this was going on, I was in therapy — I spoke about it with my therapist and she helped coach me to make the right choices.

How do you utilize emotional intelligence and active listening to create an inclusive environment in your team or organization? Could you share a specific instance where these qualities particularly enhanced team dynamics or performance?”

I won’t say it is my gender that makes me attuned to those around me, but I know as a person, I’m dialed in to people I take an interest in. By being observant of my surroundings and listening before I speak (a quality that didn’t develop in me until I was a bit more mature), I have been able to understand situations better and attend to them more effectively. My current company, Mastery Portfolio, has quarterly meetings with members of the team to check in and ensure that they are happy in the positions they are in. These innovation conversations allow us to unearth any possible personal or work related challenges and problem solve together. We don’t believe that only leadership has good ideas as we know that our folks are in the field and can articulate challenges we may not see, and therefore we want folks to tell us (without negative recourse) if there are things they’d like to change. Many of our employees have offered good suggestions and we have established an honest forum for sharing ideas and valuing each other’s experiences. Something I am quite proud of is that our people are happy working with us and when personal or professional struggles arise, we work together to figure them out. It has created a very cohesive and collaborative work environment.

What role has mentorship played in developing your authentic leadership style, and how do you communicate authentically to inspire and empower both your mentors and mentees?

One of the best parts of my job is having the opportunity to support my team when they are going after their own goals. For example, two of our team members recently wrote their first books and one of them is working on her second. As an author of many books, I have been able to mentor both of them in their writing and subsequent marketing and potential growth opportunities based on experiences I have had and learned from. I try not to be pushy with how I help, but rather let them know I’m here and give them opportunities to ask questions and/or work with me to continue to help them grow. Nothing makes me happier than to see members of my team successful and getting what they want. To me, this is a mark of good leadership — that folks want your help and they aren’t afraid to ask for it. It’s through these coaching conversations where I can humble myself about the mistakes I made and hopefully help them avoid the same pitfalls.

Ok super. Here is the main question of our interview. Based on your experience and research, can you please share “5 Ways Leading Authentically As A Woman Will Affect Your Leadership”? If you can, please share a story or an example for each.

1 . More authentic relationships — By getting to know my team well, I’m able to show my care and compassion in ways that help my team develop and grow. Additionally, these relationships have bloomed beyond the work roles and into real friendships. I’m close with my business partner, the folks on our team and I take a genuine interest in the success and happiness of each of them without judgment. Additionally, I know that these relationships are reciprocated and I need anything in the future, these are all people I know I can rely on.

2 . Being decisive about what is important and possible is also an important way I continue to lead authentically. Although I may not always have the right answer, I work hard to figure out my stance on something as quickly as possible, without shutting myself off to other people’s ideas and opinions. It’s essential that I weigh in where possible with my truth before it is influenced by others and then when I have to be flexible in my thinking when I have more information, I can humble myself to shift in my beliefs. Having that initial opinion, however, is a starting point and as a leader, you must be clear and decisive. In my school roles, deciding clearly what I expected, communicating that effectively and then supporting those around me to help them find success inside of my decision has been helpful. Being decisive has also informed my career path and has allowed me to trust my instincts when it comes to big life choices.

3 . Flexible thinking and perspective taking — Authenticity is necessary in leadership, but being flexible is equally as important. Knowing when to stand by your decisions and when to take the perspectives of others into consideration shows a great sign of humility. There have been several times I haven’t thought about something as clearly or thoroughly as I could have or I hadn’t considered the consequences of an original stance, and hearing my colleagues thoughts and experiences served to better inform the best pathway for the team while also increasing the trust between us. Valuing people is an important part of servant leadership and because I can be flexible in my thinking, unafraid to admit when I’m wrong, people inherently trust me and want to work with me.

4 . Humility — As mentioned before, humility is both a character trait and social skill that needs to be practiced in many situations. Humbling myself to those around me, showing my humanness and trying to lead with the needs and desires of others at the forefront of my decisions has helped me remain successful in every leadership role I’ve been in. Although I’m proud of my many accomplishments being humble about my success keeps me approachable and curious; this is why I always consider myself a learner first with the team. This was so in classroom with my students as well as with the adults I work with on each subsequent team.

5 . Self-aware and metacognitive — And none of this would be possible if I didn’t have a realistic idea of who I am as a person. Taking the time to really think about my choices and beliefs about important issues, gives me multiple opportunities to confirm the decisions and moves I’ve made. Because I know my shortcomings, I’m able to rally around the best folks to fill my gaps of knowledge and experience for the benefit of the mission. If I’m not the right person for something, I have an obligation to find the right person and let them lead and then learn from the situation.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

Sometimes I can be too emotional and leading this way isn’t always the most effective; for example, if I don’t see things clearly. I have found that when I’m following my heart I have to temper my feelings with whatever intelligence I can pull together to ensure that the decision isn’t only the right feeling, but also the best strategic move.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’ve been working to start a revolution to change the way we grade and assess students in school; all children deserve an education experience that both honors the dignity of students and provides an environment where they can thrive.

How can our readers further follow you online?

I’m on X @MsSackstein and @Masteryforall

I’m on LinkedIn — Starr Sackstein and so is our company Mastery Portfolio, LLC.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

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