Rethinking What’s Ahead: How One Principal is Looking Back to Move Forward

Now more than ever, education leaders need time to pause, reflect, and rethink how they want to lead moving forward. One New Leaders alum and principal shows us how.
School leader smiling group of students hugging
5/26/20
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Crises can show us who we are and who our leaders are. Now more than ever, educators and leaders across the country need time to pause, to reflect and rethink how they want to lead moving forward. “We just thought this crisis was going to be over faster,” observes Maggy Olson, principal of Milwaukee College Prep 38th Street Campus (PreK-8) and a New Leaders alum.

“Being out of school for a month is very different from being out of school for three months,” she adds. “We need to get out of survival mode, like from surviving to thriving.” Olson and her team are reimagining how their school community will thrive in this moment and beyond.

Olson’s reflections come at a time when this school year is coming to a close and the next one remains unknown. Now is the time to look back and reflect on how the COVID-19 pandemic has impacted students, families, teachers, and principals, in order to rethink and plan for all that comes next.

Using New Leaders’ end of the year reflection tool, Olson identifies the early wins she celebrates with her leadership team and the inevitable setbacks that propel them forward:

Listen to gain insight into how Olson uses her reflections to prioritize and consider how she and her staff will pivot and move forward differently in the 2020-21 school year. Central to her vision is planning for students, families, and staff to excel in whatever form the next school year takes.

Looking ahead, Olson identifies three main areas of focus: social and emotional learning, standards-based instruction, and operations. For the first two, the critical need for human connectedness – once as simple as a hug or a high-five – is taking on new importance along with the need to provide consistent opportunities for students to engage in complex learning tasks. Limiting instruction to review skills or focusing on remediation is what Olson fears most moving into the new school year. “We have hard mountains to climb,” she reminds everyone. “But we can climb them.”

Exploring existing models of successful online schools is one of Olson’s goals as she and her team consider virtual and in-person options, or a combination of both this fall. Unlike the unexpected need for rapid response in March, Olson and her team will vet the new operations plan. They will study best practices. They will continue analyzing data on student engagement over the summer to inform and refine their fall rollout. With clear direction and expectation, along with empathy and accountability, Olson plans to set a course for children and adults to thrive.

“The only way out of darkness is light,” Olson reflects. “Think about how you are bringing light into your community and bringing light to your staff and love to your students. Although we are still virtual, love is the most important factor for educators. That love is not just hugs and kisses. That love is high expectations and knowing our kids deserve the best education.”


Maggy Olson is the founding principal at Milwaukee College Prep 38th Street Campus. Under her leadership, Milwaukee College Prep has earned the highest rating from the state for overall student achievement and growth. Olson began her career almost 20 years ago as a special education coach and teacher.

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Maggy Olson

Maggy Olson

Maggy Olson is the founding principal at Milwaukee College Prep 38th Street Campus. Under her leadership, Milwaukee College Prep has earned the highest rating from the state for overall student achievement and growth. Olson began her career almost 20 years ago as a special education coach and teacher.

Maggy Olson

Maggy Olson

Maggy Olson

Maggy Olson

From New Leaders, this is our Leadership Changes Everything series. We've been elevating leaders’ voices from across the country as they share how they've been leading through COVID-19. Today we hear from Maggy Olson. She's from our Milwaukee Cohort, cohort 8.

Maggy will walk us through her reflections on COVID-19 as she works to prepare her team for next school year, using our Reflections on COVID-19 Leadership tool.

So one of the early wins was making sure that we got in contact with every single family. I'm working with our team, with our teachers and our leadership team to ensure that every kid was contacted. We were able to find out what their needs were. We really celebrated that with small things like shout outs and emails and virtual staff meetings. Then we did a huge thing for teacher appreciation where we all wrote personal notes and mailed them to them. It's really important to celebrate. I think that also kind of speaks to New Leaders' priority of preserving community and ensuring that teachers are in community. Because if we're in community, then we can drop down to the kids in that community as well.

What about when you think about setbacks? Because with wins always come a set of setbacks. What were some of your setbacks that you had when you started navigating through these challenges?

Absolutely. I think one is we just thought it was going to be over faster. So we did not take the process, very slowly and meticulously which we normally do when we're rolling something out. We vet it. We look at best practices. And instead we were flying the plane while we were building it. So I think because of that we really have pockets of excellence going on instead of a codified expectation network-wide and also schoolwide. We really rock at connecting with our families, but really ensuring that we are stopping the summer slide is kind of something that was a setback. Because the goalpost kept getting moved. So, in that we had to stop and reflect like okay, we are not coming back after spring break. So this packet will not be enough. We're not grading right now. Should we start grading? Like all of that. If we're out a month that is very different than being out of school for three months. So that was kind of a lot of navigation that we had to do and we're still playing catch up on.

The tool for leaders asks you to think about looking back and really reflecting on what has taken place in this time. But another asks you to look ahead. So next I'm going to ask Maggy to walk us through what she's considering for her 2020-21 school year and how she’s preparing her team. What are your priorities and how are you trying to set your team up for success?

When we're thinking about next year and what we would want to do, we broke it into three different buckets at our school and our network. We've looked at operations. What is it going to look like to operate in this space? Is everything going to be virtual? Are we going to be in school? Are people going to opt out? What is the CDC saying? So that's a huge thing that we're thinking about. And it's hard because we don't know if that's the toughest thing. It's just a moving target at all times.

The second thing we're really focusing on is social and emotional learning and what that's going to look like for our kids. How are we preserving community and connectedness with each other and after summer and building relationships with new teachers? Teachers are coming out of a relationship, but what is that going to look like if you're my student and I'm the teacher and we've never been in a building together. How are we building those relationships and how are we doing that? Because now we have relationships with families. We can hold them accountable. We can have those conversations with them and they're more open to talk to us about what's going on in their life because we have those relationships.

And then lastly what are we going to be teaching and how are we going to address that? I want to know how are online schools doing that so well? Because this isn't brand new. What has been successful in online settings? And how are they moving the needle and ensuring that they're still offering rigorous grade level standards and complex texts? How are we ensuring that all kids have access to that? And then what are the different moves and structures we need to put in place for families so that they have access to that?

We are looking at some assessments to see how much backslide we're having, but we all know what the data says when we look at the opportunity myth. The best way to move forward for kids is to hold them accountable to their grade level standards and give them the complex tasks that are available. So that's a huge fear I have is that everyone's going to go down the rabbit hole of remediation and we're not going to be moving forward and the kids that are going to be hurt are our Black and brown students. I am very nervous about that.

For our final question on the reflection tool, I’d love to hear how you focus on your most urgent gaps. What are you recommitting to as a plan for your next school year? What are you considering to be what you need to stop doing to address these opportunities and what you must start in order to meet your desired state?

We are meeting and constantly looking at student data and looking at engagement. How are kids engaging and students doing from a teacher's opinion – like, this is how many kids I've connected with and this is how much work they're doing. We’re also looking at Google Classroom and looking at how many assignments are actually done. So we're looking at that data to kind of see what we need to start and what we need to stop.

I really think it kind of boils down to, when you're asking about a gap, I think we need to stop – like, this emergency is going to be normal for a while. So I think we need to get out of survival mode. Like from surviving to thriving. How are we going to thrive in this environment?

The only way out of darkness is light. Think about how you are bringing light in your community. And how you are bringing light to your staff and how you're bringing that love to your students. Although we are still virtual, it's the most important factor for educators. And that love is not just hugs and kisses. That love is high expectations and knowing that our kids deserve the best education.

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