When I became a principal, I remembered every complaint I’d ever made about the ones I’d worked under.
I was going to listen. Be approachable. Explain things properly. All the things we used to say we wanted while sitting around the staffroom.
I still want to be that person. But I’ve said yes to things I should have questioned, and kept quiet because I didn’t want to seem difficult.
I’m writing as Erin because a few people would probably recognize me in this.
Before I became principal, I had opinions.
Strong ones.
About principals who were too strict.
Too distant.
Too controlling.
Too serious.
Too quick to say no.
Too slow to listen.
You know how easy it is to judge the person in the office when you are not the person in the office.
Then I became the person in the office.
And I think somewhere along the way, I made a quiet promise to myself:
I would not become one of those principals.
I would be approachable.
Reasonable.
Flexible.
The principal people could talk to.
The one who understood.
The one staff liked.
That last part is the one I did not admit out loud.
I wanted to be liked.
Not respected.
Not trusted.
Liked.
And for a while, I think I confused all three.
That is what this confession is about.
It started with small things.
Requests.
Schedule changes.
Extra chances.
Deadlines.
Things I probably should have answered more clearly.
But instead I kept finding ways to soften them.
“Let me see what I can do.”
“I’ll think about it.”
“Maybe we can work something out.”
Even when I already knew the answer was probably no.
Why?
Because no feels different when you are the one saying it.
When I was a teacher, I used to think principals were too rigid.
Now I understood why they sometimes sounded final.
If you leave every decision half-open because you are afraid someone will be disappointed, eventually nothing is actually settled.
I learned that slowly.
Very slowly.
There was one teacher in particular who made me realize what I was doing.
You can call her Claire.
Again, not her real name.
Claire was not difficult.
That is important.
She was good at her job.
Students liked her.
Parents liked her.
Staff liked her.
I liked her too.
She was confident.
Direct.
The kind of person who would come into my office, sit down, and tell me exactly what she thought.
I actually appreciated that.
At first.
Then I noticed something.
I almost never said no to her the first time.
Even when I knew I should.
She would ask for a change.
I would say:
“Let me check.”
She would ask for an exception.
I would say:
“Maybe.”
She would push back on something.
I would explain.
Then explain again.
Then somehow I would end up adjusting something.
Not always.
But enough.
I told myself I was collaborative.
Flexible.
Open to feedback.
All nice words.
Then one day another teacher said something that made me uncomfortable.
She came into my office about a schedule issue.
I told her I could not change it.
She accepted it.
Then near the end she said:
“I figured. Claire already got the exception.”
She did not say it accusingly.
Almost casually.
That made it worse.
I felt heat go straight into my face.
I said:
“The circumstances were different.”
She nodded.
“Okay.”
That was it.
She left.
And I sat there thinking:
Were they different?
Yes.
Technically.
But were they different enough?
That question stayed with me.
So I pulled up the two situations.
Actually compared them.
I felt ridiculous doing it.
But I needed to know.
The reasons were not identical.
Claire had a little more justification.
A little.
But I also knew something else had influenced me.
Claire would push.
She would question.
She would want to talk it through.
The other teacher would probably accept the answer.
That realization made me feel awful.
Because I had not been rewarding the stronger case.
I had partly been rewarding persistence.
And maybe, if I am completely honest, I had been rewarding the people whose disappointment I did not want to deal with.
That is ugly to admit.
But there it is.
I think I had created a system where the staff member most willing to challenge me had a better chance of getting flexibility.
Not because I believed that was fair.
Because I wanted the conversation to end with both of us still feeling good about each other.
That is not leadership.
That is emotional negotiation.
Once I saw it, I started seeing it everywhere.
I was slow to correct people I liked.
Slow to say no to people whose approval mattered to me.
Too willing to explain myself when someone looked disappointed.
Too quick to reassure.
Too worried about how a decision would make me look.
I called it being relational.
Sometimes it was.
Sometimes I was just afraid of being disliked.
There is a difference.
I remember one staff meeting where I knew I needed to address something.
Nothing huge.
Just a pattern of people arriving late to a required meeting.
It had been happening for weeks.
I had made little comments.
Jokes.
“Nice of you to join us.”
Everyone laughed.
Nothing changed.
I knew I needed to stop joking and actually address it.
So I prepared what I was going to say.
Simple.
“This meeting begins at 3:15. I need everyone here on time unless there is a legitimate reason.”
That was it.
I had the sentence.
I even wrote it down.
Then the meeting started.
Two people came in late.
Everyone looked at them.
One laughed.
I laughed too.
Then I said nothing.
Nothing.
I hated myself for that.
Afterward, I sat in my office and thought:
Why didn’t you say it?
I knew why.
I did not want the room to change.
I did not want people to think I was becoming strict.
I did not want someone going home saying:
She’s getting power hungry.
That phrase lived in my head more than I want to admit.
Power hungry.
Controlling.
Changed.
Forgot where she came from.
Those were the labels I feared.
So instead of risking them, I let things slide.
Then I became resentful that people were taking advantage.
Very fair.
They were following the standard I had actually enforced.
Not the one I believed I had communicated.
That was on me.
Another time, a teacher came to me about something I had already decided.
She did not like the decision.
She had good reasons.
I listened.
Then she said:
“I just don’t think this is very supportive.”
There it was.
Supportive.
One of those words that can make a principal immediately question everything.
I said:
“What would feel supportive?”
Bad question.
Not always.
But bad in that moment.
Because I already knew the boundary.
And now I was inviting negotiation because I wanted her to walk out thinking I was kind.
She told me what she wanted.
I could not do it.
Then I spent fifteen minutes trying to make her understand why.
She still left unhappy.
So after all that, I had the same decision…
and I was exhausted.
I remember thinking:
What exactly were you trying to accomplish?
Not fairness.
Not clarity.
Approval.
I wanted her to leave thinking:
I may not like the answer, but Erin is still one of the good ones.
That is embarrassing to write.
But I think that was it.
I wanted to be one of the good ones.
I do not even know what that means anymore.
Nice?
Flexible?
Never disappointing anyone?
That principal does not exist.
If she does, she is probably not making many decisions.
At some point, I started noticing the emotional math in my head.
If I say yes, she’ll be happy.
If I say no, she might be upset.
If I correct him, things could become awkward.
If I let it go, we can keep things easy.
If I push this issue, staff might think I don’t trust them.
If I don’t push it, maybe it fixes itself.
I was constantly calculating reactions.
That is exhausting.
Because people are unpredictable.
And because once being liked becomes part of the decision, every face in the room becomes data.
Someone looks unhappy.
Maybe I should soften.
Someone sighs.
Maybe I pushed too hard.
Someone stops talking.
Maybe they are angry with me.
Someone is warm.
Good. I’m safe.
It sounds ridiculous when I write it like that.
But that is honestly how it felt sometimes.
I had given everyone else too much control over whether I thought I was doing a good job.
If people were happy with me, I felt like I was leading well.
If people were unhappy, I started questioning myself.
That is not a stable way to lead.
Because sometimes people are unhappy precisely because you are doing something necessary.
I knew this intellectually.
Of course.
Every leadership training says it.
You cannot make everyone happy.
Fine.
Very easy sentence.
Try living it when the person who is unhappy is standing in your office.
Different experience.
I think the turning point came during a conversation with my assistant principal.
We were talking about a staff issue.
I was going back and forth.
Maybe we should give it another week.
Maybe we should talk informally first.
Maybe I should send a general reminder to everyone.
Maybe…
She finally said:
“Do you actually think that is the right approach, or are you trying to avoid one person being upset with you?”
I stared at her.
Rude.
Accurate.
I said:
“I don’t know.”
She said:
“I think you do.”
I hated that.
Because I did.
I knew what needed to happen.
I just did not want to be the person who did it.
That distinction changed something for me.
Sometimes the problem is not:
I do not know what to do.
Sometimes the problem is:
I know exactly what to do and I do not like how someone might feel about me afterward.
That is a different kind of leadership problem.
We had the conversation.
The staff member was unhappy.
Of course.
I survived.
Also important.
She was distant for a few days.
I survived that too.
Then things mostly returned to normal.
The world did not end.
No one organized a rebellion.
Nobody stood outside my office with signs.
It was uncomfortable.
That’s all.
I think I had spent years treating discomfort like evidence of danger.
Someone is upset with me.
Something is wrong.
Sometimes something is wrong.
Sometimes someone is just upset.
Those are not always the same thing.
I started practicing something after that.
Before I make a difficult people decision, I ask myself:
If I knew this person would still like me afterward, what would I do?
That question is uncomfortable.
And useful.
Because it removes one variable.
Sometimes the answer stays the same.
Good.
Sometimes I realize I have been bending too far.
That is helpful too.
I also ask:
If this person already disliked me, would I handle this differently?
Another annoying question.
But it helps.
I do not want warmth to buy people exceptions.
And I do not want conflict to make me harsher.
The standard has to survive both.
I am still learning.
I am better than I was.
Not cured.
That sounds like I had a disease.
I still like being liked.
Who doesn’t?
It feels good when staff trust you.
When people laugh in your office.
When someone says you are easy to talk to.
I do not want to become proud of being disliked.
That seems unhealthy too.
There are leaders who wear unpopularity like proof they are strong.
I do not want that either.
I think the difference is:
I want people to like working with me.
I cannot need them to like every decision I make.
Those are different.
I wish I understood that earlier.
There is also a difference between being kind and being agreeable.
That took me a while.
Kindness can say no.
Kindness can correct.
Kindness can hold a boundary.
Kindness can disappoint someone.
Agreeableness is more about keeping the temperature comfortable.
I was doing too much of that.
Keeping the room comfortable.
Keeping relationships comfortable.
Keeping myself comfortable.
Leadership is not always comfortable.
People are involved.
And people remember things.
They have expectations.
They react.
They talk.
They interpret.
That is the hardest part.
You cannot make a decision in a vacuum.
But you also cannot let every possible reaction become part of the criteria.
I think about that a lot now.
A few months ago, Claire asked me for another exception.
Different situation.
She came in.
Explained.
I listened.
I understood why she wanted it.
Then I said:
“No, I can’t approve that.”
She looked surprised.
Then:
“Really?”
Old me would have started explaining immediately.
This time I said:
“Yes.”
Then I gave the reason.
Short.
Clear.
She pushed once.
I listened.
The facts had not changed.
I said:
“I understand why you’re asking. My answer is still no.”
She was annoyed.
I could tell.
She left.
And I sat there.
Uncomfortable.
Very uncomfortable.
I did not chase her.
Did not send a follow-up message.
Did not find a reason to compliment her later.
Did not reconsider just because she was cold.
That sounds like nothing.
For me, it was progress.
The next day she came in about something else.
Normal.
Life continued.
I remember thinking:
Oh.
Maybe people can be annoyed with you and still work with you.
Revolutionary.
Maybe they can even like you overall and dislike a decision.
Maybe respect can survive disappointment.
Maybe relationships are stronger than I was giving them credit for.
Or maybe some will not be.
That is the part I still do not love.
Some people will think differently of you after you lead them.
Some relationships will change.
Some people will call you unfair.
Strict.
Difficult.
Unsupportive.
Maybe sometimes they will be right.
You should listen for that.
But sometimes that is simply the price of not making every decision around approval.
I think I am finally accepting that.
I want staff to feel respected.
I want them to know they can speak honestly.
I want them to trust that I will listen.
I want to be approachable.
All of that still matters to me.
But I do not want “Do they like me?” sitting quietly beside every leadership decision anymore.
That question takes up too much space.
So that is my confession.
I wanted to be liked.
I probably still do.
I just do not want to need it as much.
Because needing it made me less clear.
Less consistent.
Sometimes less fair.
And weirdly, probably less trustworthy.
People should not have to guess whether the answer depends on how uncomfortable I am with disappointing them.
I would like to know what The Good Principal thinks.
How do you stay approachable without becoming approval-dependent?
How do you care what staff think of you without letting that control your decisions?
And how do you know whether you are being genuinely relational…
or simply afraid of being the bad guy?
I’d also like to hear from other school leaders.
Did you enter leadership determined to be the principal everybody liked?
What did that cost you?
Thank you for giving us a place where we can admit that sometimes the person we are most afraid to disappoint is ourselves.
— Erin
FROM THE GOOD PRINCIPAL’S OFFICE
Erin, there is a difference between wanting to be liked and building your leadership around being liked.
The first is human.
The second becomes expensive.
Most people prefer warmth over hostility.
Most school leaders would rather walk through a hallway where staff smile than one where people avoid eye contact.
Wanting good relationships is not weakness.
In fact, strong relationships are essential to leading schools well.
The problem begins when approval becomes evidence that your leadership is good and disapproval becomes evidence that your leadership is bad.
That is the trap you described.
Someone likes your decision.
Relief.
Someone looks disappointed.
Doubt.
Someone becomes distant.
Maybe I was wrong.
Someone praises you.
Maybe I handled it well.
Now the emotional reaction of the staff becomes your leadership evaluation system.
That system will make you unstable because people respond to decisions based on many things.
Their interests.
Their expectations.
Their stress.
Their previous experiences.
Their relationships with you.
Sometimes whether they had breakfast.
You cannot build fair leadership around keeping all of those reactions positive.
One of the most important realizations in your confession is this:
You often knew what you needed to do.
The uncertainty came after you imagined the reaction.
That means the leadership problem was sometimes not decision-making.
It was tolerance for disappointment.
Those are different skills.
A leader can know the right boundary and still struggle to hold it when a real person pushes against it.
That is why sayings like:
“You can’t make everyone happy.”
are true and almost useless by themselves.
The harder question is:
What do you do when the unhappy person is sitting three feet away from you?
Their face changes.
Their voice changes.
Maybe they say:
“I thought you were more supportive than this.”
Now the principle has a pulse.
That is where approval-seeking usually appears.
You explain more.
Soften.
Negotiate.
Offer a concession.
Maybe postpone.
Not always because the decision deserves adjustment.
Sometimes because you want the tension gone.
Your assistant principal gave you a valuable question:
“Do you think this is the right approach, or are you trying to avoid one person being upset with you?”
Keep that.
It cuts through a lot.
Another useful question is the one you developed:
“If I knew this person would still like me afterward, what would I do?”
That does not automatically produce the right answer.
But it reveals how much fear of rejection is affecting the judgment.
There is another distinction worth holding onto:
Being relational does not mean being endlessly agreeable.
Relational leadership means relationships matter.
It means you listen.
You understand context.
You communicate with dignity.
You notice impact.
You treat people like people.
It does not mean relationships always determine the outcome.
Sometimes the most relational thing you can do is be clear.
Vagueness can feel nicer initially.
But it often makes relationships less trustworthy.
Think about the examples you gave.
“Let me see.”
“Maybe.”
“I’ll think about it.”
Those can be perfectly legitimate responses when you genuinely need time.
But when you already know the answer and use them because you do not want to say no, you are not actually protecting the relationship.
You are delaying the discomfort.
And sometimes you are creating false hope.
Clear does not have to mean cold.
You can say:
“I understand why you’re asking. I can’t approve it.”
That can be kind.
You can say:
“I value you, and this still needs to improve.”
That can be kind.
You can say:
“I know you disagree. The decision still stands.”
Also kind.
Kindness is not the same as giving people the answer they wanted.
There is another important consequence of approval-seeking that you discovered:
it can become unfair.
If the person who pushes hardest gets more flexibility, then persistence becomes part of the selection criteria.
If the staff member you like gets extra chances, warmth becomes part of the performance standard.
If the person you fear upsetting receives the exception, emotional pressure becomes influence.
You probably never intended any of those things.
Most leaders do not.
They emerge gradually.
That is why consistency matters.
Not robotic sameness.
But enough structure that your comfort with the person is not deciding what happens.
A good test is:
Would I make the same decision for someone I liked less?
And the reverse:
Would I handle this person more harshly if we already had conflict?
Both matter.
People-pleasing can distort judgment in either direction.
You can be too soft with people you want approval from.
You can also become unusually rigid with difficult people because you have stopped caring about their approval entirely.
Neither is fair.
The issue should drive the response.
Not the relationship temperature.
There is also something very important in your line:
“I want people to like working with me. I cannot need them to like every decision I make.”
That is probably the healthier goal.
You should care about how people experience your leadership.
If many staff consistently experience you as dismissive, confusing, arbitrary, or disrespectful, listen to that.
Do not hide behind:
“Leadership isn’t a popularity contest.”
That phrase can become an excuse for poor leadership too.
But individual disappointment is not the same as a pattern of mistrust.
One person being upset because they did not get what they wanted tells you something.
It does not tell you everything.
Look for patterns.
Are you clear?
Do people understand how decisions are made?
Are standards reasonably consistent?
Can staff disagree with you safely?
Do you admit mistakes?
Do you explain important decisions without over-defending them?
Do people feel heard even when the answer is no?
Those are stronger measures than:
Did everyone leave happy?
Because sometimes good leadership ends with someone unhappy.
There is another skill here:
letting people have their feelings without immediately managing them.
That can be surprisingly difficult.
A person can leave your office annoyed.
You do not necessarily need to send them a reassuring email.
Someone can disagree with you.
You do not necessarily need another conversation until they finally understand.
Someone may think you are wrong.
You are not required to correct their opinion of you.
That is uncomfortable.
But it creates healthier relationships.
People are allowed to have an emotional response that you do not fix.
You are allowed to remain respectful without controlling what they feel.
That is where a great deal of leadership maturity lives.
And this is exactly why Managing Schools for the Terrified, Vol. 1 & 2 fits your confession so naturally.
One of the hardest parts of managing schools is not knowing the leadership principle.
Most principals already know:
be fair,
communicate clearly,
address problems early,
hold boundaries,
do not make everyone happy.
The difficulty begins when actual people react.
A staff member becomes cold.
A former peer says you changed.
Someone tells others you are unfair.
A good employee is disappointed.
A person you respect does not agree with you.
Now the clean principle becomes messy.
Managing Schools for the Terrified is built for that messy middle.
Especially the parts around:
You Are Now Leading People Who Used to Be Your Peers
You Can’t Make Everyone Happy
and
How to Say No Without Becoming the Villain.
The point is not to turn school leaders into people who stop caring what others think.
That would be terrible advice.
The goal is to care about relationships without handing those relationships control over every decision.
It is learning that you can be approachable without being endlessly negotiable.
Warm without being vague.
Understanding without automatically conceding.
And firm without performing toughness.
There is also a practical shift that may help.
Before a difficult conversation, decide what belongs to the conversation and what does not.
For example:
What is the issue?
What standard applies?
What flexibility genuinely exists?
What part is not negotiable?
Know those before the emotional reaction arrives.
Otherwise the reaction can start rewriting the boundaries in real time.
And if new information genuinely emerges?
Change your mind.
Good leaders do.
But know why you changed it.
Not:
They seemed upset.
Instead:
I learned something relevant that materially changed the decision.
That protects you from becoming rigid.
It also protects you from becoming endlessly movable.
There is another phrase I would keep near you:
Discomfort is not always a warning.
Sometimes discomfort means something genuinely wrong is happening.
Pay attention.
But sometimes discomfort simply means:
You disappointed someone.
You set a boundary.
You addressed an issue.
You stopped trying to be everybody’s favorite principal.
That feeling may pass without requiring correction.
You discovered that with Claire.
She was annoyed.
You did not chase.
Then she returned.
Life continued.
That experience matters because it taught your nervous system something your leadership training probably never could:
Someone can be upset with you and the relationship can survive.
That is powerful.
And sometimes the relationship will not survive unchanged.
That is harder.
But if a relationship depends entirely on you never saying no, never correcting, and never disappointing the other person, then it is already asking something leadership cannot sustainably provide.
So Erin, perhaps you do not need to stop wanting to be liked.
You just need to put that desire in the right place.
Let it influence how you treat people.
Not whether you enforce the standard.
Let it remind you to be respectful.
Not to avoid necessary conversations.
Let it encourage warmth.
Not vagueness.
Want to be liked if you want.
Most of us do.
Just do not ask approval to do the job of a compass.
It was never built for that.
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