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Becoming a School Leader During COVID-19

Starting out as a school leader in the current crisis is daunting, but an intentional and equity-based leadership entry plan can help

October 14, 2020
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It is hard to imagine starting a new job as a school or district leader right now, but many are. Some of these leaders are stepping into roles never having met their colleagues or staff in person, serving families and students whom they can only connect with through devices, all of whom have experienced some kind of trauma, stress, or uncertainty related to the challenges of the pandemic. Leadership entry is always daunting, but leadership entry now is especially precarious.

This spring and summer, I worked with a group of education leaders planning transitions into new roles in schools, districts, and education nonprofits. The experience reminded me how important it is to create an intentional leadership-entry plan, but it also elevated the importance of making sure that plan is equity-focused and human-centered.

For new leaders stepping up to serve our young people and their families at a critical time, here are a few takeaways that arose from my discussions.

Embrace the dual-track agenda

A new leader today needs to be doing the day-to-day work of continuing to lead through the crisis, while simultaneously grabbing onto the opportunities the crisis affords.

In other words, in a typical leadership entry process, the leader is looking for strengths to build on, challenges to address, and opportunities to pursue. Leadership entry today will require seeking out opportunities to heal, repair, and transform. Let your community know that this is your approach. This will give them confidence that you are taking action now while leading your community towards a better future.

Ask yourself: How might I design my entry activities so as to listen for feedback that can help us now and aid in our recovery, while also capturing ideas for the future? Where are the opportunities that would not otherwise exist? How might we capitalize on those opportunities?

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"Leadership entry is always daunting, but leadership entry now is especially precarious."

Understand your context

A typical planned entry emphasizes talking with key players early on, like supervisors, board members, and colleagues to get insight and feedback on the current context. But what is often missing is intentional effort to understand the community’s history — its history of oppression, opportunity, and leadership for racial and social justice — and the connection to present-day challenges and opportunities.

In this current time, it seems especially important to locate the leaders and connectors, the formal and informal leaders that are trusted sources of information and influence. If you can, consider creating a “virtual” kitchen cabinet, an informal group of thought partners, and check in with them for advice and guidance along the way. Their insights about past and present challenges are critical.

Ask yourself: What do you know about the organization and the community in which it is situated? What is the historical context? What are the present-day challenges and the connection between the two? Who can you talk to early on to gain this insight?

Understand yourself

Just as important is understanding yourself. Again, a typical planned entry emphasizes introducing yourself, your why, and your core values. But absent an examination of your multiple identities, including your racial identity — what brings you strength and perhaps hesitation, how you think you may be perceived, and what biases you may hold — you will enter into your role and your early interactions with blind spots. The conversations you’ll have during entry are inherently difficult, and no matter your racial identity or other identity markers, you may be emotionally triggered. You need to understand why, so that you can find your center, stay present for the people you lead, and remain compassionate to the people you serve. This “mindful listening” exercise, from Shane Safir’s The Listening Leader, may be especially important now.

Ask yourself: Who are you? How does your lived and professional experience inform your leadership? How does your race and other identities inform how you view this role and your relationship to the community it serves?

Be transparent and build trust

Critical to leadership entry is transparency and relational trust building. The creation of an intentional entry plan helps with transparency, for sure — people should know what you are doing and why — but focusing on activities that build trust is key, especially as trust is understandably low in communities where the institution has done them wrong. It is critical to seek out multiple perspectives, to “see” people, to show competence early on by getting after some quick wins, and to follow through on your plan. Use social media, for example, for regular reporting of your actions and insights, and be open to the feedback you hear.

Ask yourself: What can people expect of you? How will you model your core values? How will you follow through? How will you share your moves and your learning every step of the way?

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"Nothing is more important than listening to students, especially students of color and other students who are marginalized. How can you center the stories of individual students to help guide you during this difficult time?"

Listen with empathy

As we design an engagement plan to seek out multiple voices so as to identify the strengths, challenges, and opportunities of the organization, the voices of students, families, and staff of color are often missing. We also sometimes forget what we ought to be listening for, which is insight into how the organization is working — its technical ways of working and its relational ways of working.

If you lead an education organization, nothing is more important than listening to students, especially students of color and other students who are marginalized. How can you center the stories of individual students to help guide you during this difficult time? Social distanced or virtual home visitation, like the “trust visits” held this year for vulnerable students in Chelsea MA, or community walks and visits, like we’ve seen Jason Kamras do in Richmond, Virginia, are great examples of ways to safely get the insight you need to lead, listen and build relationships.

Ask yourself: How can you gain multiple perspectives? How will you gain access to and center the voices of those most marginalized?

Hold steady

Crises are inevitable in these roles — but we are now facing a crisis unlike anything we’ve ever seen brought on the dual challenge of COVID-19 and the racial injustices that have plagued this nation.

Remember: new leaders need to “hold” the people they serve. Leaders can put their communities at ease through information flow and transparency, but they can also provide a place for voice and influence. Interpersonal “holding” provides space to check in on one another other and model care for oneself.

Leadership entry is often exhilarating because of its freshness, but today’s leadership entry is daunting because of its many hazards. It’s so easy to get it wrong, but leading with equity, transparency, and humanity will help you get it closer to right.

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About the Author

Photo of Jennifer Perry Cheatham
Jennifer Perry Cheatham
Jennifer Cheatham is a senior lecturer on education at HGSE and the co-director of the Public Education Leadership Project (PELP). She has served as the superintendent of the Madison (Wisconsin) Metropolitan School District, chief of instruction for Chicago Public Schools, executive director of curriculum and instruction for San Diego City Schools, and coach and professional developer for the Bay Area School Reform Collaborative (BASRC) in San Francisco. She previously led a multiyear initiative aimed at improving academic literacy for middle school students in Newark, California, where she began her career as an eighth-grade English teacher.
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