Your Principal Vs. Your Principles: How to Speak Up to Administrators. And When to Shut Up.

Your administration is like a bra: 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.

Pick 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 to follow up on a discipline referral.

Pick 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. Focus on your highest priority and leave other topics for another day.

Offer a solution.

Administrators have the same problem with overwhelming to–do lists that 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 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 often hear that students need to save face and will react badly if confronted in public. 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.

Maintain a “professional responsibilities” file with copies of paperwork you’ve turned in to the main office. Make notes on any discussion that could relate to your future employment. If you believe you’ll want proof of a conversation with an administrator, try to have that conversation by email. Just remember that email is a record for both parties. Proofread carefully before you hit “send,” and never write work–related emails when you are mad.

Be professional.

If talking to your boss makes you feel like you’re stuck in a Dilbert cartoon, try not to let it show. Trying to change a supervisor’s management style or IQ won’t help anyway, and losing your cool could hurt your career.

Be realistic.

It’s usually not worth heading to the main office with matters outside your administration’s control. School–level administrators 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.

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