Q: After our Welcome Back Orientation, we had an employee indicate she wished to drop our health coverage effective January 1, 2015, and purchase an individual policy on the exchange. Is this allowed, as our insurance renews October 1?

Policing students on technology and social media can feel like a Sisyphean effort at times. Students always seem to discover workarounds for security obstacles set before them, whether it’s an expensive firewall or the latest generation of record encryption software. Enter Exhibit A: The Yik Yak app.

When is a disaster an unavoidable strike of fate versus a foreseeable misfortune? That question encapsulates the potential risk your school evaluates every time a tragedy like the Sandy Hook shooting or the Ebola outbreak appears on national media. But no one could have foreseen the consequences a tick bite would have on a young private school student returning from a school-hosted trip to China—consequences that would have one school sued for millions of dollars.

A new school year means new students, new teachers, and—yes—new problems for you, the School Head, to resolve. No matter your experience level, you’ll make a decision this year that will be unpopular with someone. You’ll receive private and public criticism for those decisions, however necessary or difficult they were to make, and be left questioning yourself. What is the most graceful way to respond to such censure? Oddly enough, we can look to HBO’s new satirical news segment “Last Week Tonight with John Oliver” for two great examples of how leaders and organizations should (and should not) respond to candid criticism. The first, commercial fruit juice company POM Wonderful, responded well; the second—which we’ll cover next month—responded poorly.

While the “normal” hiring season has long since closed, School Heads are not strangers to the last-minute change of faculty or staff. Despite the urgency of these eleventh hour hiring decisions, you can’t afford to skip comprehensive interviews. Phone interviews in particular can play a vital role in the interviewing process, as they allow you to determine early on who might do well and who is not suited to the role before you and your search committee invest time and personnel into the in-person interview. With that in mind, we’ve assembled some quick tips on phone interviews to help them proceed as smoothly as possible during this “off season” recruitment.

A typical Board meeting at many schools is based on a standard format primarily structured around reports from the School Head and various committees. This type of meeting often fosters results that call for little or no action. When trapped in such routine agendas with no true focal points, many Board meetings simply “go through the motions.”

Effective Board committee work can be torpedoed by a Board that listens to a committee’s proposal—and then proceeds to alter or redo the work. As the Chair of a committee, you can envision the damage that results. Your committee members are frustrated—as are the other Trustees who feel that your group did not do its work well enough.

California is about to make history by passing the strictest rules governing students’ online data in the country. Once the governor signs the legislation, Senate Bill 1177 will ban targeted Web advertisements based on educational data and unnecessary “student” profiles in the Golden State. The bill makes student information such as personal demographics, sports participation, grades, and health files off-limits for advertisers' use. Schools across the country—both public and private—struggle to stem the leak of student information to data-mining companies, as well as stop students from exposing themselves to inappropriate sites. One solution has been firewalls and filters that block sites deemed dangerous to either the network or the student-user. There are several types of website filters available for school use, and as the first of a two-part series on Internet security, we’ll talk about the common firewalls and filters used by schools and how they work.

With generally more involved parents and dedicated teachers, students in private schools often deftly complete work that would challenge their public school peers a year or two their senior, according to the National Center for Education Statistics. But what do you do when you have a student who’s exceptional even in this elite environment, and his or her parents request that you bump their child to the next grade level?

It’s another school year at your private-independent school, which means it’s time to introduce a new set of families to your annual fund campaign—to start educating them on how important their gifts are to the school at large. Many schools have adopted short, easily digestible videos as their primary explanatory platform. Posted on the school’s social media accounts and shown during parent gatherings, these videos can quickly explain both the existence and importance of community participation in the annual fund. Not feeling especially tech-savvy or inspired for your own video? Let’s look through five annual fund videos produced by private schools of all shapes and sizes to get ideas for your school’s annual fund introduction.