Roadside Assistance from the District Office

As school leaders navigate challenging times, roadside assistance can be invaluable.

By Jessica Cabeen

You have a plan, you’ve done your research, you’ve created leadership teams to pilot the project.

Students have buy-in, families are excited, but you forgot to loop in the leaders around and above you. And shortly you find out that your project has stalled or stopped altogether.

It’s easy for school leaders to get so caught up in the day-to-day operations of our school that we forget about maintaining connections with those whose view is a few thousand feet higher than ours.

Effective leadership includes making sure that we integrate that higher level perspective in the decisions we are making for our school. Finding intentional ways to establish and maintain these connections with the “leaders of leaders” in our system needs to be part of our routine checklist (and check-in) so we can continue to move forward successfully, with strong support.

Here are five strategies I use:

1. Set up monthly meetings.

Find a time to connect with your supervisor on a monthly basis and create an agenda to go through. Sharing grows and glows, personal goals, site-based goals and data to support where you are in the process of continuous improvement is incredibly important.

Ask your supervisor what information you are missing or what implication this work will have on the schools above and below you. The more front loading you do with your work, the more support you’ll receive and the better the end result will be.

2. Stay focused.

Be careful not to make this a competition. Just because the other middle school in town is moving to a block schedule, doesn’t mean you should as well. Pick one thing and do it well before you move onto the next. If you are focused on reviewing your Grading Practices, it is okay to say “Not right now” to a district initiative to implement healthy snacks during the school day.

If something off-task comes across your desk as an ask, not a mandate, find a way to communicate that you see value in this idea, but that right now your team is moving in a direction in which this doesn’t seem to fit.

3. Don’t multitask in meetings.

In administrative meetings does your device light up when an agenda item doesn’t pertain to you and your school? Challenge yourself to stay engaged – even if a topic way outside your own context.

By leaning in and listening to other agenda items with intent, you might discover an unconventional way to fund your new outdoor classroom, update the cameras in your school, or find a place that will provide you materials and set up your Holiday Hot Chocolate Bar for staff without your having to go out and do it yourself.

4. Ask for help.

This winter my former direct supervisor was stuck outside, in the cold, with me for an hour guiding traffic at our high school. I took this opportunity as a way to ask a question about my own leadership and a recent plan that went off course.

Because of his higher view of the organization and his knowledge of my leadership style (10 years and counting of working together), he was able to identify the missteps and suggested ways to move forward that I couldn’t see for myself.

5. “Poke holes in my idea.”

Have an idea for a new master schedule, implementing PLCs, changing the elective offerings, or integrating 1:1 in a more student-driven way? A strategy I use is to ask supervisors and other stakeholders to come in and “poke holes in my ideas.” While this is a way to see from other viewpoints, as the initiator of the ideas it is essential that you walk into this think-tank with an open mind and leave your defensive responses at the door.

Unconventional leadership means taking a look at what other leaders are doing, no matter what the context and setting, and learn from them. And with detours, speed bumps and other roadblocks always in the offing, don’t forget to lead like a learner, take risks, fall forward and have fun in the process. It makes the journey so much more enjoyable.

Jessica Cabeen is the principal of Ellis Middle School in Austin, MN. She was the 2017 Minnesota Nationally Distinguished Principal and a Future Ready Principal™ Advisor. She is the coauthor of Balance Like a Pirate (2018) and author of Hacking Early Learning (2018), Lead with Grace (2019), and Unconventional Leadership (2020). She loves to connect with other educators on Instagram, Facebook, Voxer, and Twitter @JessicaCabeen and her website,

Read a MiddleWeb review of Unconventional Leadership.


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