3 Lessons I Learned Leading Startups That I Wish I Knew as a Principal

This post is written by my former co-worker and current husband, Keith Westman.  Follow him on Twitter at @keithwestman.

Having worked in leadership roles in both public education and in the edtech industry, there are three organizational behaviors that, should I go back to school or district leadership, I would implement on Day 1.  

#1:  Daily or Weekly Standups

What’s the best way to have a well-run organization (whether a school or an edtech company)?  Communicate!  Take ten minutes every morning and assemble your office staff.  Go through the day, discuss what is expected to happen that day, and give every person a chance to ask questions.  Not only will doing so ensure everyone is on the same page, everyone’s day will run smoother.  

Oh, and what’s with the “standup”?  Everyone stands up for the meeting.  There isn’t a more effective way to keep a meeting short and on-task than by making people stand up while it’s happening.

#2:  Chat

I am against intercoms in schools.  In my opinion, they are the most intrusive and abused devices in existence – completely disruptive to teaching and learning (or general sanity). Download Slack (or embrace the use of any messaging tool that your teachers already like) and let every teacher and staff member in your building use it to communicate. These tools are efficient and allow for regular communication.

I like Slack because users can create “channels” that your staff can follow (i.e. lunch duty, after school clubs, 5th-grade team, etc.).  Of course, your staff may think big brother is watching their conversations.  But, as long as conversations on your messaging system put students first, what’s the worry?  

#3:  Ring the Bell!

Make no mistake, right behind the intercom, bells are the most obnoxious systems in schools.  But, in the workplace, ringing a bell is not the way employees know when to stop doing “this” and start doing “that” like the way many schools use bells to determine when Math is over and PE begins.

Bells are a way to let people know something positive has happened somewhere in the organization.  Full disclosure, this is stolen from car dealerships who ring bells with every car sale.  But, at Otus, big or small, we ring the bell.  A code bug is squashed…ring!  A sale is made…ring!  And, more of a full disclosure, we literally ring the bell emoji in Slack (you already know how I feel about distractions).

Bottom line, find your bell.  Don’t literally ring a bell in your school, but do make a point to publicly celebrate successful moments with your staff.  Maybe send an email blast or a group chat message containing small victories from the day (a great PD session, a positive call from a parent, etc.). Everyone has bad days and by “ringing the bell” you are showing that despite your bad day, good moments are always happening at school.


About Keith: Dr. Keith Westman taught third grade, served as a K-8 technology coordinator and was a middle school principal during his ten years working in school districts.  He left public education to work with his childhood friend who had started an edtech company.  That company, Aspex Solutions (now part of Frontline Education), grew up to provide AppliTrack and K12JobSpot.com to thousands of school districts and millions of job seekers throughout the country. Keith is the COO of Otus, the makers of the Otus Student Performance Platform, based in Chicago’s popular Fulton Market neighborhood, and moonlights as an Adjunct Professor at DePaul University.

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