Earlier this month, we celebrated National Assistant Principals Week, recognizing these essential school leaders at the Portland Public Schools. Many of us think of assistant principals as in charge of a school’s day-to-day operations, including being the “disciplinarian.” But today’s assistant principals are much more.


Working in tandem with principals, they’re an integral part of a school’s leadership team and play a key role in building the school’s culture and tone. They work closely with students and support and supervise school activities. They also look out for safety and wellness, and the traditional discipline of the past has evolved to a focus on positive behavioral support. They work with students and families to understand the circumstances behind student behaviors and develop plans to help students achieve their potential.

As a former assistant principal, I deeply appreciate all our assistant principals do. This month, as part of an ongoing series about our outstanding PPS staff, I’m featuring one of these vital school leaders who exemplifies the modern assistant principal: Robyn Bailey at Lincoln Middle School.

Robyn joined PPS in 1998 as an educational technician at Lincoln and has been there ever since, becoming a teacher and then assistant principal. She does amazing work at the school, including leading an effective intervention strategy to reduce student chronic absences. Here’s more about Robyn:

How did you get into this field?

Growing up in Portland, many people in my family were in education, but I always said I wasn’t going to be an educator. I went to school initially to be a nurse, but discovered that was not what I wanted. I graduated from college with a degree in linguistics and worked at a bank in their education department before deciding I wanted to be an educator. I was an ed tech, then realized I wanted to get my teaching degree. I taught math, English and science and then became an English Language Learner teacher. I took on leadership roles while teaching, in the union and at the building level, and that influenced my decision to become an administrator.


How has your varied experience impacted your job now?

The most important thing you can do is make connections with students and families. Once kids trust you, they’ll work closely with you. Because I was in the classroom so long, I know that if a kid is doing something wrong there are underlying reasons. Once you figure out what they are, you can usually make that connection with students. Very rarely do I have to discipline a student because they know me, they trust me and when I ask them to address a behavior, they do it. With families, they have to trust you, they have to understand that you are there for all of our students to be safe and secure. I’m fortunate to have an amazing team supporting this philosophy.

How has COVID impacted your work around chronic absence?

I have a great team that supports the idea that we have to go to people’s homes to make connections. But now we do many porch visits, because we can’t go into homes. We really try to target why a student is having difficulty in coming to school and we make whatever adjustments we need to.

What drives you in your job?

I want to do better every day. I want to find solutions to things that aren’t working well. I want things to be systematized and predictable so that people here, whether adults or students, can anticipate what’s happening and know that they are going to be appreciated and have the opportunity to do well.

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