Teacher leadership: growing your impact in–or beyond–the classroom

Are you considering stepping into a leadership role in education but feeling unsure of where to start?

In this article + podcast episode, I sit down with Starr Sackstein, an experienced educator, consultant, and author, to talk about the journey from teacher to leader. Starr shares her personal story of leaving the classroom, the challenges she faced in leadership, and the lessons she’s learned along the way.

We dive into practical steps for preparing yourself for leadership, how to balance progressive ideas with system demands, and the importance of staying connected to the heart of teaching—your students. Starr offers honest advice on overcoming imposter syndrome, advocating for yourself, and navigating the unexpected responsibilities that often come with leadership roles.

Whether you’re aspiring to lead your department, take on an instructional coach role, or simply want to grow your influence within your school, this episode is packed with insights to empower you to take the next step with confidence. You’ll learn:

• How to know when you’re ready to leave the classroom for leadership.
• Strategies for building credibility and trust with your peers.
• Ways to stay connected to students and avoid “initiative fatigue.”
• Practical tips for advocating for your goals and protecting your time.

If you’ve ever wondered whether leadership is the right move for you, this conversation will leave you inspired and ready to take action.

Listen to episode 323 below,
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ANGELA: My guest today is Starr Sackstein, an accomplished educator and author who is dedicated to transforming education through innovative practices. With a background in secondary humanities education, she has championed learner-centered paradigms, assessment reform, and technology integration. As an author of many influential books, including Hacking Assessment, Starr empowers educators globally with practical strategies for creating learner-driven classrooms. 

Her experience related to this podcast episode is quite diverse, as she’s played many different leadership roles in schools, as well as online platforms. She currently works as the Massachusetts State Coordinator for Educators Rising, an organization centered around solving the teacher shortage and creating a more diverse educator workforce locally. And, Starr is the COO of Mastery Portfolio, a boutique edtech company supporting schools as they shift to competency-based or standard-based learning and assessment.

I wanted to talk with Starr for those of you who want to create change in your local schools, either in addition to a classroom teaching position or through a full-time leadership role. As Starr underscores, you don’t need to leave the classroom to be a leader, and there are lots of ways to build your capacity as a leader while you’re in the classroom. 

Transitioning out of the classroom

ANGELA: Starr, you have successfully transitioned from a classroom teacher to leadership and consulting roles and lots of other positions as well. Tell me, what inspired you to take that step out of the classroom, and how did you know you were ready?

STARR: It’s such a good question. And it’s kind of like what I addressed when I first started from teacher to leader. I think in the classroom, I had complete control over everything, but I was starting to get a little bored. I was kind of pushing the boundaries on how much I could put on students—like how I could teach them to have complete ownership of what was going on. And I think after I had gotten to a certain point, I was just like, I would really like to be able to help other folks do the things that I’m doing.

It was the perfect combination of personal stuff going on with my son and wanting to be closer to home with a more flexible schedule in case I had to visit school or help him during the day. So I was being nudged by necessity, but also boredom. I moved into an instructional coach role from a classroom teacher role. And I would say that it was the best of both worlds because I was still teaching one or two classes, like having a model classroom for people to come visit, but I was also coaching teachers. Of all the roles that I’ve done, instructional coach was definitely the one I liked the best because it kept me aware of what it was like to be in the classroom and therefore gave me credibility in terms of working with my peers.

The kids are the best part of what we do. Not to say that working with teachers isn’t awesome—and I’ve certainly fallen in love with teacher teams that I’ve worked with—but kids, I mean, they’re the best, right? When you move into leadership positions, I think as teachers, we don’t really know how much is being hidden behind the curtain. And I think there was a certain amount of ignorance I took into my first leadership position. When I saw how much I was trying to safeguard my teachers from some of the stuff coming down from the top, I realized there’s a lot we don’t see.

Sometimes decisions that look bad are actually the best of several bad options. When you’re on the receiving end of those messages, it’s not great, but even when you’re in leadership, it’s not great either. There was a lot of learning and definitely just readiness for a new challenge. I think I’m the kind of person who likes to keep it interesting.

Challenges of moving into teacher leadership

You definitely are a person who seeks out new challenges, and I’m the same way. That’s how I felt when I left the classroom. There was just a knowing that I was ready to try something new, that I had accomplished the work I needed to do in that setting. Of course, that doesn’t mean I felt 100% confident in it, but I knew that I wanted something different. I think a lot of teachers can relate to that experience.

What were some of the challenges that you faced when you moved out of the classroom and into leadership? You’ve talked a little bit about how there’s more going on behind the curtain than you know. It’s a very different skill set than what you needed as a teacher.

Yes. In the beginning, the transition—I expected myself to be an expert at things because I had been in the classroom for 16 years. You spend that much time in the classroom, and you really do become an expert at a lot of things. That isn’t to say there aren’t challenges even after that long, but you at least know how to approach a problem when you experience it. There are very few new problems that arise after that amount of time.

When you move into a new position with that history and experience, you expect yourself to excel immediately. I thought, “This is going to be easy. I know how I would do leadership.” But the first big shift was starting over as a beginner, even though I had all this knowledge. It was humbling and frustrating. I had forgotten what it was like to start something new, and that was very challenging.

Plus, I was in a completely different system, learning its ebbs and flows, the responsibilities I had, and the people I was working with. Many were lifers in the district, older than I was, and while I respected their experience, there was also skepticism toward me as a first-time leader with some pretty progressive ideas about classroom instruction. I think I terrified them a little bit.

Building relationships was a major challenge because I was no longer a known entity. In my previous school, everyone knew my name and what I could offer. Coming into this new experience, they knew my social presence and author persona but didn’t know me as a worker. There were a lot of unknowns. When you’re in a space where people don’t know your work ethic or expertise, it’s harder than you anticipate.

Advancing progressive ideas within existing systems

How did you balance wanting to bring in new progressive ideas and create change while also learning the new system and building credibility and buy-in from the people already working there?

I really tried to lead by example. In that first position, the only time I really had my department together, the first major change was that I was hired as a humanities director, not an English director. I oversaw six different content areas and was expected to bring them together as one department. That was a huge hurdle—getting them to see themselves as a unified humanities department rather than separate groups for English and social studies.

I modeled my expectations during monthly meetings. I avoided sit-and-get sessions. Instead, I used station rotations and encouraged cross-content collaboration by looking at standards and identifying how skills aligned across classrooms. I emphasized consistent language and expectations across content areas. After each meeting, I sent surveys to learn what was most useful and what goals they were working on.

Being in classrooms regularly helped a lot too. I wanted them to see me more than just during evaluations. I also offered to model new strategies in their classrooms or observe and provide feedback in a neutral way. The first teacher to take me up on that was a middle school Spanish teacher. After working together, she told others that I did what I said I would do. That went a long way in building trust and reducing skepticism.

Staying connected to the classroom

Moving into leadership can sometimes feel like stepping away from the heart of teaching and the best part—the kids. How did you stay connected to the classroom and students even in leadership roles? That’s a big fear for many teachers considering leadership roles.

Agreed. It’s not the same relationship, but it’s crucial to stay connected. At least 65% of my time was spent in classrooms, doing walkthroughs and observing learning. I wanted students to know who I was and not fear me when I walked in. I also wanted them to feel comfortable being themselves, even if they were antsy or rambunctious.

I co-taught one class with a teacher. It was a subject I had taught before, and I didn’t feel right about having my own class since I knew I’d be pulled away for meetings often. Other ways I stayed connected were by running or co-running clubs and involving students in decision-making processes. For example, having student focus groups or including students on committees made a big difference. Students know what they need and want, and giving them a seat at the table is powerful.

Overcoming self-doubt and imposter syndrome

A lot of educators struggle with imposter syndrome when stepping into leadership. It can be intimidating to start over as a beginner, especially after being an expert teacher. What advice do you have for overcoming self-doubt during this process?

First, accept that it’s going to be there. Give yourself grace and know you’re not alone. I struggled a lot with imposter syndrome and often wrote about it. Back when blogging was more common, I noticed many people only shared the good things happening in their spaces. But all of us know education has plenty of challenges, even for the best teachers. Normalizing that and focusing on how you recover from mistakes is crucial.

If your district doesn’t provide a mentor, find one yourself. I was lucky to have mentors both within and outside my district who offered different perspectives. They kept me grounded and reminded me that making mistakes is part of the process. The weight of leadership mistakes can feel heavier because they’re more visible, but grace and humility are essential.

Shifts needed in teacher leadership and education

You’re such a visionary and always have innovative ideas. What shifts do you hope to see in education leadership in the next five to ten years? How can teachers play a role in shaping that vision?

I hope to see a shift away from grades and standardized testing toward portfolio-based assessments. That would require significant changes in pedagogy and day-to-day instruction, but it’s necessary. Leaders must be visionary while also focusing on the small, incremental steps needed to achieve big goals. Initiative fatigue is real, so it’s important to prioritize and ensure decisions align with long-term objectives.

Teachers are the ones who make magic happen. They need the freedom to innovate and support for trying new approaches. Leaders should be clear about their goals and provide the necessary time and resources to achieve them.

They also need to avoid constantly shifting priorities or piling new initiatives on top of existing ones without removing anything. Explicitly communicating what’s no longer required helps teachers focus their time and energy.

To close out, what’s something you wish every teacher understood about leadership and the role they play in it?

One important takeaway is that leaders don’t have to be perfect, just like teachers don’t. Grace and humility are essential. When mistakes happen, it’s important to own them, repair any harm, and model what it looks like to recover from setbacks.

Build relationships before asking people to do things. Make sure everything you’re asking them to do is something you’d be willing to do yourself. Leadership is about collaboration, empathy, and staying grounded in your purpose.