Questions to Ask Your Principal
For teachers who want a clearer read on how their principal makes decisions. Twenty questions about observations, backing with parents, budgets, workload, promotion routes and why staff leave, useful in a check in or a start of year meeting.
The questions
Open any question for the note
What are you being measured on this year, and where does my subject fit into it?
Why ask it
Principals answer to a district or a board with its own targets, and most staff never find out what those are. Once you know, half of the decisions that seemed arbitrary make sense, and you can frame your requests in terms they can defend upward.
When you walk into my room, what are you looking for?
Why ask it
Asks for the actual criteria rather than the rubric. A specific answer, student talk, evidence of what they did yesterday, who is not participating, gives you something to work on, while a general answer about good teaching gives you nothing.
What does a strong observation look like to you, and what would worry you?
Why ask it
The second half is where you learn the real threshold. Knowing what reads as a red flag to your evaluator is more useful than knowing what earns a top mark, because that is what gets followed up.
How do you prefer to hear about a problem: email, dropping in, or a scheduled time?
Why ask it
Getting this wrong is why teachers feel unheard. Some principals lose anything said in a hallway, others treat email as a paper trail and go cold on it, and either way it is worth knowing before you have something serious to raise.
If I disagree with a decision you have made, how do you want me to bring it?
Why ask it
Asking during calm weather sets the terms for a future disagreement, and the answer tells you plenty. Watch whether they describe a route for dissent or simply say their door is always open.
What is decided in this building, and what comes down from the district?
Why ask it
Saves you campaigning for something your principal cannot grant, and shows where they have discretion. It also reveals which unpopular policies they are enforcing rather than choosing.
What is in the budget for my department this year, and who decides it?
Why ask it
Ask for the number and the timing of the decision. Most requests fail because they arrive after the money is committed, not because they were unreasonable.
When a parent comes to you about me before speaking to me, what happens?
Why ask it
This is the moment teachers most want to know their principal's instinct. Listen for whether the answer includes redirecting the parent back to you and telling you promptly, or whether you would find out later.
If I hold a line on behavior and a family pushes back hard, what backing can I expect?
Why ask it
Ask for a recent example rather than a principle. How they describe handling the last case predicts your own far better than any statement about consistent expectations.
Which of my current duties could I hand over if I took something else on?
Why ask it
Reframes a workload conversation as a trade instead of a complaint, which makes it much harder to wave away. It also shows you which of your duties they consider low value.
What roles are likely to open here in the next two years, and how are they filled?
Why ask it
The process matters as much as the vacancy. Whether posts are advertised, filled internally or quietly offered tells you what you should be doing now to be considered.
What professional learning will you fund, and what would be on my own time and money?
Why ask it
You want the boundary in advance: cover for the day, the course fee, travel, or nothing. Vague encouragement to pursue growth is how teachers end up paying for their own development twice.
Who in this building is worth learning from, and would you help set that up?
Why ask it
Asking to observe a colleague is a low cost request that principals rarely refuse, and the names they give you show whose practice they actually rate rather than who is most visible.
What do you see as my strongest quality in the classroom, and my weakest?
Why ask it
Ask for both in one breath so the answer cannot stop at the compliment. If the weakness is a surprise, you have found the gap between how you think you are seen and how you are.
Is there anything in my class data you read differently than I do?
Why ask it
Administrators see your numbers next to everyone else's and in a longer time frame. Their reading is not always right, but hearing it prevents a conversation in an evaluation where you are hearing it for the first time.
How are class lists and schedules put together?
Why ask it
The most consequential decision for a teacher's year, and usually the least explained. Knowing the sequence and who has input tells you when a request can still be accommodated.
What do you do when two staff members cannot work together?
Why ask it
You are asking about their appetite for conflict. Someone who describes separating people and waiting it out will handle a future problem in your hallway very differently from someone who names a conversation they had.
Why have teachers left this school, and what changed as a result?
Why ask it
The second half separates a principal who tracks retention from one who treats departures as personal choices. Compare the answer against what leaving colleagues actually told you.
At the end of the year, what would you want to be able to say about my work?
Why ask it
Turns a vague evaluation into an agreed target while there is still time to hit it. Write down whatever they say and bring it back in the spring.
What do you need from me that you have not asked for?
Why ask it
Principals often want something specific, coverage of a committee, help with a new colleague, support for a change they are trying to land, and hesitate to ask an already busy teacher. The answer is usually the cheapest goodwill available to you.
Working With Your Principal
Practical guidance for the conversation itself
Timing and Setting
Ask for the meeting, do not ambush
Request fifteen minutes and say what it is about. Principals spend their day being intercepted, and a corridor conversation about your schedule is likely to be half heard and then forgotten by the next interruption.
Match the question to the calendar
Budget and staffing questions are worth asking in the semester before decisions are made, usually the winter or early spring. Asking in August tells you what was decided without you.
One topic per conversation
Bundling workload, resources and a promotion question into a single meeting means the easiest one gets answered and the rest get postponed. Choose the one that matters most this month.
Raising Something Difficult
- Bring the problem and one option you would accept. It changes the meeting from a complaint into a decision they can make.
- Describe what happened rather than what someone is like. Dates, times and quotes travel much further than characterizations.
- Say plainly what you want as an outcome. Many teachers leave that unstated and then feel dismissed.
- Send a short summary afterwards, thanking them and restating what was agreed. It is courteous and it creates a record.
- Try to resolve it in the building before going to the district or your union, and say that you intend to if it is not resolved.
Mistakes Worth Avoiding
- Only ever appearing at the office door with problems, so your name is associated with difficulty.
- Treating a positive observation as final. Ask what would have made it stronger.
- Assuming silence means approval. Principals prioritize noise, and a quiet, capable teacher can go years without support.
- Asking for something that costs money without knowing when the budget closes.
- Reading a decision as personal before checking whether it came from above them.