#59 Blog. POV: What Employees Really Want to Ask Their Managers.

Hana Chen Zacay
6 days ago
7 min read

August: kids at home, traveling, hanging out at home, and, let’s be honest, a little more social media scrolling.

Some of the viral Instagram trends where people mimic how they would act or talk as kids got me thinking about this month’s blog:

What do employees really want to ask their managers?

Because sometimes… we are all still five years old at work. 😂

Managing up, or just maintaining a healthy relationship with your manager, is not easy, right?

You are not friends and even if your relationship is cool and breezy, there are still some lines you don’t cross and some questions you don’t exactly feel comfortable asking.

So how do we get answers to the REAL questions we have?

Can we ask them as they are? How do I ask them “gently”? When is it too direct? And, knowing that directness is super cultural, what feels perfectly normal to one person might feel incredibly uncomfortable to someone else. From experience 😉

But there is another question I find even more interesting:

How do we transform emotional questions into productive leadership conversations?

And perhaps even more importantly:

Which question will support me best in achieving the result I’m actually looking for?

I hope this one will be as funny to read as it was for me to write.

Let's ask the questions we would ask as kids 😂

I had tons of questions in mind that my kids keep asking me, and I really wanted to try them at work.

So… how do you think your manager would react if you walked into their office and asked:

Am I your favorite?

Did I do something bad?

Is this good enough?

But why?

That’s not fair! (not a qustion, but I had to)

Promise you won’t be mad?

Obviously, you probably wouldn't actually say these things at work.

But here's the thing:

How many times have you thought them?

Maybe you just translated them into more professional language. The words are different.

The emotion underneath them may not be.

The question underneath the question

Sometimes we ask a professional question when what we really have is an emotional question. And there is nothing wrong with that.

We want to know that we're doing a good job and where we stand. We want to feel trusted and valued. We want to understand why decisions were made. We want to know that we still belong.

The challenge is learning how to turn that emotional need into a question that can actually move the conversation forward. Because asking a better question can change the outcome.

1. “Do you like me?”

Let's be honest. Most of us don't actually need our manager to like us.

But we do want to know: Do they value me? Do they trust me? Do they see my contribution?

You could try: “What do you value most about working with me, and where could I improve?”

It won't fit every conversation, but it moves you from looking for reassurance to getting useful information about your strengths and development opportunities.

2. “Are you mad at me?”

This can happen after a small or big interaction.

A short Slack message. A canceled 1:1. A different tone in a meeting. Your manager suddenly seems quieter.

And your brain starts filling in the blanks. Our brains don't particularly like missing information or uncertainty. When we don't have enough information to understand what's happening, we naturally try to make sense of it based on what we do know, what we have experienced before, and what we are worried might be true. Research on perception shows that our existing beliefs, expectations, goals, and fears can influence how we interpret incomplete information.

And when uncertainty feels threatening, our brains can be especially good at creating the story for us.

How about trying: “I noticed our last conversation felt a little different. Did something I did create a concern for you?”

You're not accusing your manager of being angry. You're checking your assumption.

And that's important because our brains are very good at creating stories when we don't have enough information. Sometimes our gut feeling will reflect reality, but sometimes it won’t.

3. “Did I do good?”

This might be one of the most common questions employees have.

But simply asking “Did I do a good job?” usually gives you a very limited answer: “Yes, you did great!”. And then… what?

You feel good for five minutes, but you haven't necessarily learned anything. It’s not black or white; there is so much grey.

Try: “What did I do well that I should repeat?”

And then: “What would you have done differently?”

Now you're not asking for reassurance from your manager, you're asking for development.

And feedback matters. Gallup research has found that employees who receive meaningful feedback from their manager at least weekly are significantly more likely to be engaged.

So maybe the better question isn't: “Did I do good?”

It's: “What can I learn from what I just did?”

4. “Why her and not me?”

Ouch.

This one can bring out the five-year-old in all of us. “But WHY HER?!”

Maybe she got the promotion. Maybe he got the project. Maybe someone else got the opportunity you wanted.

And underneath the frustration is often a very legitimate question- “What am I missing?”

How about trying: “I’d like to understand what you were looking for when you made that decision. What would I need to demonstrate to be considered for a similar opportunity in the future?”

Now you've moved from comparison to clarity and from resentment to development.

You may not love the answer. But at least you have something you can work with.

5. “Am I in trouble?”

This one is probably my favorite.

Because employees don't always know where they stand. And when managers don't provide enough feedback, employees often fill the gap themselves.

Again- our brains don't particularly like missing information or uncertainty. When we don't have enough information, we naturally try to make sense of it based on what we know, what we have experienced before, and what we are worried might be true.

So imagine this:

Your manager sends you a short Slack message: “Can you stop by my office tomorrow?”

That's it.

No context.

Your manager may simply want to discuss a project.

But your brain might immediately go:

“What did I do?” “Are they upset with me?” “Did I miss something?” “Am I in trouble?” “Am I getting fired?”

The manager sent seven words.

Your brain wrote the rest of the story.

So next time, try: “How am I tracking against your expectations right now? Is there anything you think I need to address?”

You're asking for clarity while there is still time to do something about it.

Managers- It's easy to read this blog and think: “Great. Employees just need to learn how to communicate better.”

Not so fast.

If your employees constantly need to ask, “Am I doing okay?” maybe you're not giving them enough feedback.

If they keep asking, “Why her and not me?” maybe they don't understand how opportunities and decisions are made.

If they ask, “Are you mad at me?” maybe there is a trust or communication gap worth paying attention to.

Sometimes the question isn't the problem.

The fact that they don't feel comfortable asking the real question is.

And the data supports just how important this relationship is. Gallup's research finds that managers account for about 70% of the variance in team-level employee engagement. And there is an interesting perception gap, too: Gallup research found that 50% of managers say they provide feedback weekly, while only 20% of employees say they receive it weekly.

Think about that.

The manager may be thinking:

“I give my team plenty of feedback.”

The employee may be thinking:

“Does my manager even know how I'm doing?”

Both people can genuinely believe they're right.

That's a leadership problem- not simply a communication problem.

So what should we actually ask?

Before you ask your manager a question, try pausing for a second.

1. What am I actually trying to find out?

Feedback? Reassurance? Clarity? Recognition? Trust? Career growth?

2. What outcome do I want from this conversation? What’s my intention?

Do I want information? To improve? To repair the relationship? To change something?

These are not always the same thing.

3. What is the most direct but constructive way to ask?

You don't need to turn every question into corporate language. You don't need to sound robotic. And you definitely don't need to pretend you don't have emotions.

You just need to ask a question that gives the other person a chance to actually help you.

Managing up isn't about saying the “right” thing.

I think we sometimes make managing up way too complicated.

It isn't about perfectly navigating office politics. It isn't about making your manager happy. And it isn't about hiding what you're really thinking behind polished language.

It's about learning how to have the conversation you actually need to have.

Sometimes that conversation starts with:

“I noticed something and I want to check my assumption.”

Sometimes it's: “I don't understand the decision. Can you help me understand it?”

Sometimes it's: “I'd like to know what I need to do to get to the next level.”

And sometimes…it's simply: “But why?”

Because underneath the professional question, there is often a very human one.

And great managers don't just answer the question employees ask.

They learn to listen for the question underneath it.

One last thought

The next time you catch yourself thinking:

“I can't ask that.”