Sending Yourself to the Principal’s Office: How to Have Difficult Conversations with Administrators

Your administration is like a good pair of shoes: if it offers the support you need, you both look and feel better. If it fits poorly, it can get in your way and even become painful. This makes it understandably scary when you have to approach your principal directly, but a tough conversation doesn’t have to mean making enemies in the main office. Walk in with the following tips in mind, and you are more likely to walk out happy.

Choose the right moment.

Certain times of day or year are tense for administrators. If your boss is handling an emergency, district supervisors are in the building, or a high-stakes test is next week, it’s a bad time to knock on the door.

Choose one issue at a time.

Your principal is more likely to listen to your request to replace broken desks if it’s not combined with an unrelated complaint about the lunch schedule (or even a related complaint about a dripping faucet). Focus on your highest priority and leave other topics for another day.

Offer a solution.

Administrators have overwhelming to-do lists just like teachers do. Your principal will be more receptive if you approach with a plan of action you’d like her to sign off on rather than a problem you hope she will figure out how to solve.

Offer to do most of the work.

When someone is trying to sell you a car or a gym membership, they handle the paperwork themselves; all you have to do is say yes and sign. Keep this model in mind when you want your principal to approve your field trip request. If you get the answer you want, expect to make phone calls, fill out paperwork, and collect permission slips on your own.

Keep it to a minimum.

Before crossing an administrator’s radar, consider your own current scorecard: Did your principal have to calm down angry parents last week? Have you just requested a schedule change or ordered expensive supplies? Have you been writing lots of referrals? If so, give it some time. Requests and complaints can combine with other issues to make you seem like a high-maintenance employee.

Keep it private.

We’re often reminded that students need to save face and will react badly if confronted about problem behavior in front of peers. This advice applies to people of any age, and it definitely applies to your boss. Don’t embarrass your principal—or yourself—by airing private complaints in public.

Keep records.

Make notes on any discussion that could relate to your future employment, and keep a file containing copies of any related paperwork. If you believe you’ll want proof of a conversation with an administrator, try to have that conversation by email. (If it has to be a verbal conversation, sometimes a follow-up note—“Thanks for speaking with me today! Here’s my understanding of our conversation”—can serve the same purpose.) Just remember that email is a record for both parties. Proofread carefully before you hit “send,” and never write work-related emails when you’re mad.

Be professional.

Even if you and your boss rarely see eye to eye, try not to let it show. Trying to change a supervisor’s management style or long-held opinion won’t help anyway, and losing your cool could hurt your career. Focus on what you can control: bringing a positive attitude to the table, and (if possible) framing the conversation in a way that speaks to your boss’s stated priorities.

Be realistic.

It’s usually not worth heading to the main office with matters outside your administration’s control. School-level officials aren’t in charge of every decision, and there is a limit to the number of times your principal can approach higher ups with requests or grievances; principals need to stay on their boss’s good sides too.

Is there something we should talk about before you head to the main office or send that email?

If you’re about to have a high-stakes discussion with an administrator, this might be a good time to book a session of See Me After Class Office Hours. These are one-on-one Zoom or phone sessions tailored to any teaching-related topic you want to talk about. Best of all, I don’t work for your school district, answer to your principal, or eat lunch in your teachers’ lounge. And everything we discuss is completely confidential. To book a session choose one of the options below and click the “Book Me” button to select an available time from the calendar. If you experience any technical difficulties, you can also try this direct link to the booking page.