There’s someone on my staff I find difficult to deal with, and I feel awful admitting that.
She doesn’t even have to do anything sometimes. I see her name in my inbox and I’m already bracing myself.
I know that isn’t fair. Whatever she’s bringing to me deserves to be heard. But lately, I’ve been wondering how much my feelings about her are getting in the way.
Call me Monica. I’d rather keep my real name out of this.
There is a teacher on my staff I genuinely like.
Not “professionally appreciate.”
I mean I like her.
She is funny.
Warm.
Good with students.
The kind of person who can walk into the staff room on a terrible day and somehow make everybody laugh.
She remembers birthdays.
She brings food.
She notices when someone is having a bad week.
She has been at the school longer than I have.
And before I became principal, we were friendly.
Not best friends.
But close enough.
Coffee sometimes.
Lunch.
Messages outside work.
The kind of relationship where you can complain about a meeting afterward and know the other person gets it.
Then I became principal.
And for a while, nothing really changed.
At least I thought nothing changed.
She still joked with me.
Still stopped by.
Still told me things.
I was relieved.
I remember thinking:
Maybe this is going to be easier than everyone says.
Very cute.
Then I had to correct her.
That is when I understood.
The problem wasn’t that she was difficult.
The problem was that I liked her.
And I didn’t want the relationship to change.
It started with something small.
Late reports.
Not once.
A pattern.
Nothing catastrophic.
But enough that other people were waiting on her work.
The first time, I reminded her casually.
“Hey, can you send that through today?”
She smiled.
“Absolutely, Ma’am. Sorry.”
Done.
Then it happened again.
Another deadline.
Another delay.
I sent a message.
She replied immediately.
“Working on it.”
Fine.
Then again.
And again.
Each time I found a way to make it sound smaller than it was.
Just checking.
Quick reminder.
When you get a chance.
No rush, but…
Actually, there was a rush.
That was the point.
I just didn’t want to sound like her principal.
Which is ridiculous.
I was her principal.
But every time I needed to address it properly, something in me resisted.
Because I knew what the proper conversation would do.
Not necessarily destroy the relationship.
But change it.
Make the roles visible.
She would sit on one side of the desk.
I would sit on the other.
And suddenly we would not be Monica and Sarah anymore.
We would be principal and teacher.
I hated that.
So I waited.
That was my first mistake.
The second mistake was pretending waiting was kindness.
I told myself:
She has a lot going on.
She is usually good.
She has been under pressure.
Everyone slips sometimes.
All true.
But also convenient.
Because if I treated it as a temporary problem, I did not have to have the uncomfortable conversation.
Then someone else complained.
Not formally.
Just:
“Are we still waiting for Sarah’s part?”
I said:
“Yes. I’ll follow up.”
There was a tone.
Not rude.
But enough.
And I knew immediately what they were thinking.
If this were someone else, would you have allowed it this long?
That question landed hard.
Because I didn’t know.
Maybe not.
Actually…
probably not.
That was the moment I realized I had turned liking someone into a leadership problem.
I went back to my office and sat there for a while.
I could feel myself becoming defensive even though nobody had actually accused me of anything.
She has earned some flexibility.
She contributes a lot.
She is reliable in other ways.
People do not see everything.
Again, all true.
But underneath all of it was something much less professional:
I did not want her to be upset with me.
That was the truth.
I wanted to keep being the principal she liked.
The easy principal.
The reasonable one.
The one who “understood.”
And apparently I was willing to let other people absorb some inconvenience to keep that version of myself intact.
That was not a pleasant realization.
So I scheduled a conversation.
Not immediately.
Of course not.
I waited until the next day.
Then almost moved it again because I told myself she seemed stressed.
Amazing how creative you become when you do not want to do something.
Eventually she came in.
Closed the door.
Sat down.
And smiled.
“What’s up?”
That made it worse.
I almost softened the whole thing before I even started.
I said:
“I wanted to talk about the reports.”
Her face changed slightly.
Not angry.
Just more careful.
She said:
“Okay.”
And there it was.
The shift.
I hated it.
I explained the pattern.
The missed deadlines.
The impact on other people.
I tried to keep my tone normal.
Probably too normal.
At one point I actually heard myself say:
“I know you’ve had a lot going on.”
Why did I say that so early?
Because I wanted her to know I was still on her side.
Before I had even finished explaining the concern.
She nodded.
Then said:
“I didn’t realize it was that big of a deal.”
That sentence bothered me.
Because part of me wanted to say:
It became a bigger deal because I didn’t address it properly the first three times.
Instead I said:
“I should have been clearer earlier.”
Which was true.
She looked surprised.
Then said:
“I thought you understood.”
There it was.
That one hurt.
Not because it was disrespectful.
Because I knew what she meant.
I thought you understood me.
I thought our relationship meant you knew why.
I thought you would give me room.
And I had.
Too much room, maybe.
I said:
“I do understand. But I also have to be fair to everyone who is waiting on the work.”
She went quiet.
Then:
“Right.”
I hated that “right.”
Everything about her changed.
The way she sat.
The way she answered.
More formal.
Shorter.
I wanted to fix it immediately.
Explain more.
Tell her this didn’t change how I saw her.
Tell her I appreciated her.
Tell her I wasn’t angry.
Tell her we were okay.
I could feel myself wanting reassurance from the person I was supposed to be giving feedback to.
That was uncomfortable.
So I stopped talking.
Probably the best thing I did in that conversation.
She eventually said:
“I’ll make sure it’s done.”
I said:
“Thank you.”
Then she left.
No argument.
No tears.
Nothing dramatic.
And I sat there feeling like I had broken something.
Not badly.
Just enough.
For the rest of the day, she was different with me.
Or maybe I imagined it.
Probably both.
She passed me in the hallway.
“Hi, Ma’am.”
Not:
“Hey, Monica.”
Ma’am.
She had always called me Ma’am around students.
But this was just us.
That stayed with me.
The next morning she came into the office with the reports.
All done.
She put them down.
“There you go.”
I thanked her.
She smiled.
Professional.
Perfectly fine.
I missed the old smile.
That sounds ridiculous even writing it.
She had done exactly what I needed.
The issue was corrected.
Everything worked.
And I was sitting there mourning a tone of voice.
This is why people are the hardest part.
Policies do not look disappointed.
Schedules do not become distant.
Spreadsheets do not remember when you used to have coffee together.
People do.
And so do you.
For the next week, I overanalyzed everything.
She didn’t stop by as much.
Was she avoiding me?
She ate lunch with different people one day.
Was that because of me?
She laughed with another teacher in the hallway and I had this stupid moment where I thought:
She used to come tell me things like that.
What was wrong with me?
I had corrected a performance issue.
I had not ended a friendship.
But apparently my brain did not know the difference.
Then I started doing something worse.
I became extra nice.
Not obviously.
But I noticed.
I asked how she was doing more often.
I commented on something good she had done.
I found reasons to stop near her classroom.
It took me a few days to realize what I was doing.
I was trying to repair a relationship she had not actually told me was broken.
And I was doing it because I could not tolerate feeling disliked.
That was embarrassing.
Then one afternoon she came into my office.
Door open.
No appointment.
Like before.
She said:
“Do you have a minute?”
I said:
“Of course.”
She sat down.
For a second I thought she was going to talk about the reports.
She didn’t.
She told me about a student.
Normal work conversation.
We talked for ten minutes.
Then as she was leaving, she stopped.
She said:
“By the way, I was annoyed with you.”
There it was.
I laughed because I didn’t know what else to do.
“I figured.”
She said:
“I know you were right. I just didn’t like hearing it from you.”
That sentence was almost a relief.
Because finally we were talking about the actual thing.
I asked:
“Because we knew each other before?”
She nodded.
“Probably.”
Then she said:
“It felt weird.”
I said:
“It felt weird for me too.”
She smiled.
A real smile this time.
And said:
“I noticed.”
Great.
Apparently my professional discomfort was very subtle.
We both laughed.
Then she said something I have thought about a lot since.
“You can’t give me a pass just because we get along.”
I said:
“I know.”
Then she said:
“And I probably shouldn’t expect one.”
That was probably the most honest moment either of us had had about it.
Because that was the real issue.
Neither of us had said it out loud.
But the relationship had created an expectation.
Maybe not intentionally.
Maybe not even consciously.
But it was there.
I would understand more.
She could be more relaxed.
I would give her the benefit of the doubt.
And to be fair, sometimes that is okay.
Relationships should have trust.
Context matters.
History matters.
But there is a point where understanding becomes avoidance.
And I crossed it.
I think what bothers me most is not that I was too soft with her.
It is why.
I was afraid of losing something.
That made me less fair.
Not only to everyone else.
To her too.
Because while I was being “nice,” I was not actually being clear.
I gave reminders instead of expectations.
Hints instead of feedback.
Then when it finally became a formal conversation, she was surprised.
I had created part of that surprise.
If I had addressed it earlier, maybe it would have been smaller.
Less loaded.
More normal.
I think sometimes leaders tell themselves they are protecting relationships when they are really protecting themselves from discomfort.
That is what I was doing.
I did not want to be the bad guy.
I did not want her to leave my office thinking:
She’s changed.
I did not want to become one of those principals we used to complain about when I was still teaching.
That thought comes up more often than I like.
Before leadership, it was easy to have opinions about leaders.
Too strict.
Too soft.
Too distant.
Too controlling.
Too friendly.
Then you get the office and realize every option irritates someone.
Very educational.
There is also something else I have noticed since becoming principal.
I am sometimes harder on people I do not know well.
Not intentionally.
But it is easier.
If there is no relationship, there is less to lose.
You can say:
“This needs to improve.”
And go home.
When you genuinely care about the person, every boundary feels personal even when it is not.
That is dangerous.
Because fairness cannot depend on how emotionally easy the conversation is for me.
I have been thinking about that a lot.
Would I have addressed the same issue sooner with someone I found difficult?
Yes.
Probably.
There is the answer.
That means I need to be careful.
Liking someone cannot buy them a different standard.
At the same time, I do not want to become cold just to prove I am fair.
That seems wrong too.
I still like her.
We still talk.
Sometimes we still have coffee.
The relationship did change.
Of course it did.
I am her principal now.
Pretending that did not matter was part of the problem.
But changed does not automatically mean ruined.
That is something I am learning.
There is a different kind of honesty available now.
I can say:
“I care about you, and I still need to address this.”
Both can be true.
I wish I had understood that sooner.
I think I was operating as if I had two choices.
Protect the relationship.
Or do my job.
Maybe that was false.
Maybe the healthier version is:
Do the job in a way that respects the relationship.
Not avoids the responsibility because of it.
There is a difference.
A month later, something smaller happened.
She missed another deadline.
Not by much.
Old me probably would have sent a light message:
Hey, just checking…
This time I went to her classroom after students had left.
I said:
“Sarah, I need that by tomorrow morning.”
She looked at me.
Then smiled.
“Got it, Ma’am.”
I pointed at her.
“Don’t Ma’am me.”
She laughed.
There she was.
The world did not end.
The friendship did not collapse.
She completed the work.
I went home.
No emotional crisis.
Progress.
I know there will be harder situations than this.
Much harder.
Performance issues.
Conflict.
Formal discipline.
Times when liking someone will not make the responsibility smaller.
And I am not completely confident I will handle those perfectly.
Probably not.
But now I know something I did not understand when I first became principal.
Sometimes the hardest person to lead is not the person you dislike.
Sometimes it is the person you really like.
Because with them, the stakes feel different.
You are not only worried about the decision.
You are worried about the relationship surviving the decision.
And maybe that is where leaders can get into trouble.
We start managing the relationship instead of managing the issue.
We postpone.
Soften.
Hint.
Excuse.
Give one more chance.
Then another.
Not because the person earned all of them.
Because we are afraid to become someone they no longer like.
That is hard to admit.
But I think it is true for me.
So this is what I would like to ask The Good Principal.
How do you stay human with people you supervise without letting closeness change the standard?
How do you correct someone you genuinely like without turning cold just to prove you are being professional?
And maybe the question I am still learning to ask myself:
Am I giving grace because grace is appropriate…
or because I am afraid of what happens to the relationship if I do not?
I would really like to hear from other school leaders too.
Have you ever delayed a conversation because you liked the person too much?
Did the relationship change afterward?
And if it did…
was that necessarily a bad thing?
Thank you for giving us a place to admit that sometimes leadership is hardest precisely because the people involved matter to us.
— Monica
FROM THE GOOD PRINCIPAL’S OFFICE
Monica, there is a sentence in your confession that gets very close to the heart of this:
“I was trying to protect the relationship.”
That sounds generous.
Sometimes it is.
But as you discovered, there is an important question underneath it:
Protect the relationship from what?
From unnecessary harm?
Good.
From humiliation?
Absolutely.
From careless communication?
Yes.
But if what you are protecting the relationship from is an honest conversation that your role requires, then protection can quietly become avoidance.
And avoidance has consequences.
You experienced one of them.
By the time you finally had the conversation, Sarah was surprised.
Not necessarily because the expectation was unreasonable.
Because your earlier communication had taught her the issue was still relatively small.
Quick reminder.
Just checking.
When you get a chance.
Those phrases did not match what you were actually thinking.
You were already concerned.
Other people were being affected.
But because you did not want the relationship to feel different, you made the concern sound lighter than it was.
That can feel kind in the moment.
It often creates confusion later.
This is one reason difficult conversations are frequently easier when they happen earlier.
At the beginning, you may only need to say:
“I’ve noticed this has happened twice. I need us to fix it before it becomes a pattern.”
Small issue.
Clear expectation.
No accumulated resentment.
No formal tone required.
But when leaders wait because they hope something will resolve itself, the eventual conversation has to carry all the history the earlier conversations avoided.
That is harder for everyone.
There is another distinction worth making:
Grace is not the same as vagueness.
You can understand someone’s circumstances and still be clear.
You can say:
“I know you have a lot going on, and I still need this by Friday.”
Both parts can be true.
The understanding does not have to erase the expectation.
Similarly:
“You are someone I value, and this part of the work needs to improve.”
Again, both.
That may be the skill you are learning.
Not how to become detached enough to correct people.
How to hold warmth and accountability in the same conversation.
There is a myth in leadership that professionalism requires emotional distance.
Sometimes distance helps.
But people are not interchangeable units.
You will naturally connect more easily with some people than others.
You will like some staff members.
Others will test your patience.
Some will remind you of yourself.
Some will become friends or former friends.
Pretending those differences do not exist does not automatically make leadership fair.
Fairness comes from noticing when those differences begin affecting decisions that should be based on something else.
You asked a powerful question:
Would I have addressed this sooner if it were someone I found difficult?
Your answer was yes.
That is useful information.
Not evidence that you are a bad leader.
Evidence that liking someone was influencing your threshold.
Once you can see that, you can compensate for it.
You can ask:
What would I do if this were another staff member?
Am I changing the standard because of the facts, or because this conversation is emotionally harder for me?
Have I given this person a chance I would not give someone else?
Those questions help separate legitimate context from favoritism.
There is another side to this.
Leaders sometimes discover they overcorrect.
They become harsher with people they like because they are afraid others will think they are showing favoritism.
That is not fairness either.
If you would normally handle a first missed deadline with a conversation, do not suddenly issue a formal warning because the teacher happens to be your friend.
The goal is not:
Treat people you like worse.
The goal is:
Do not let liking or disliking someone become the hidden standard.
The work should determine the response.
History and context can inform how you communicate it.
That is different.
You also noticed something very human after the conversation:
you became extra nice.
That is worth watching.
Leaders sometimes feel guilty after giving difficult feedback and then begin compensating.
More compliments.
More attention.
More reassurance.
More friendliness.
It can unintentionally blur the boundary again.
You do not need to punish someone after a difficult conversation.
But you also do not need to prove immediately that the relationship survived.
Give it some room.
People are allowed to be annoyed with you.
That sentence may be important here.
People are allowed to be annoyed with you.
Even people you like.
Even good people.
Even people whose friendship or respect matters to you.
Disappointment is not always damage.
Awkwardness is not always rupture.
A colder greeting for a few days does not necessarily mean the relationship is destroyed.
Sometimes it means someone is processing being corrected by a person they care about.
They are allowed that space too.
And Sarah eventually gave you something valuable when she said:
“You can’t give me a pass just because we get along.”
That was not rejection.
That was an invitation to a more honest relationship.
She recognized the same tension you did.
And perhaps the relationship became less easy afterward…
but more real.
There is something else in your confession that many school leaders experience, especially when they begin supervising former peers.
Before leadership, relationships can be relatively uncomplicated.
You complain together.
You joke about decisions.
You have shared frustrations.
Then one person gets the position.
Now there are things you cannot say.
Information you cannot share.
Decisions you may have to make about someone you used to sit beside.
The relationship changes.
It has to.
That does not automatically mean closeness disappears.
But pretending the position has not altered the relationship usually creates problems.
This is exactly the kind of situation explored in Managing Schools for the Terrified, Vol. 1 & 2.
Not because there is a magic script for managing someone you like.
There isn’t.
But because a large part of school leadership is learning how to manage the human complications nobody warned you about:
leading people who used to be peers,
handling difficult employees,
dealing with adult behavior,
saying no without becoming the villain,
holding boundaries,
and discovering that people problems are rarely clean.
Sometimes the difficult employee is not someone hostile.
Sometimes it is the person you genuinely enjoy.
Sometimes the hardest conversation is difficult precisely because you already know the person behind the performance issue.
Managing Schools for the Terrified is built around those moments.
The situations where knowing the management principle is not the problem.
You already know you should address the issue.
The hard part is figuring out how to actually do it when a real relationship is sitting across the desk.
One idea from this kind of situation is particularly useful:
Do not wait for the relationship to make the conversation easier.
It probably will not.
Instead, make the conversation smaller by having it earlier.
Name the behavior.
Explain the impact.
State the expectation.
Give the person room to respond.
Then stop.
You do not need to wrap every correction in ten minutes of reassurance.
Sometimes leaders do that because they are trying to manage the other person’s feelings before those feelings even exist.
That can make the message harder to understand.
Clarity can actually be kinder.
Something like:
“I value what you contribute here. I also need to address something specific.”
Then address it.
Not:
“I really like you, and I hope you don’t think I’m being unfair, and I know you’re under pressure, and I don’t want this to come between us, but…”
By the time you reach the actual issue, both people are exhausted.
You are allowed to be warm and direct at the same time.
That balance may be one of the most important skills in people leadership.
And maybe the biggest shift for you is this:
You do not need every relationship to remain exactly as it was before you became principal.
That may not be possible.
Some relationships will become more formal.
Some people will pull back.
Some friendships may survive in a different form.
Some may not.
That can hurt.
But your job is not to preserve every relationship unchanged.
Your job is to lead people fairly and respectfully.
If a relationship can survive honesty, good.
It may even become stronger.
If it can survive only because you avoid necessary conversations, then the relationship is already influencing the leadership more than it should.
You asked how to stay human without letting closeness change the standard.
Perhaps it begins here:
Care about the person.
Be clear about the work.
Do not confuse one with the other.
You can like Sarah.
You can care about Sarah.
You can value the history.
And still say:
“This needs to change.”
That does not make the relationship fake.
It may be what allows it to become honest enough to survive the position.
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