How to Have a Conversation with Your Critical Boss

An overly critical boss can turn your dream job into your worst nightmare. But whatever your career path, you deserve to feel safe, respected, and valued at work. Learn what you can do to turn a bad boss situation around.

Rachel Cooke
6-minute read
Episode #613
The Quick And Dirty

Having an overly critical boss can put a damper on your career. But use these strategies to turn things around:

  • Use empathy to assess why your boss might be behaving in this way
  • Reflect on what your boss might be trying to communicate
  • Acknowledge and feel your emotions, but leave them out of the conversation you'll have with your boss
  • Arrange a one-on-one to thoughtfully share your concerns and propose a path forward
  • Know and honor your boundaries to decide whether it's time to consider a job change

Over the years I’ve had bosses who inspired me, pushed me, challenged me, scared me, bored me, made me laugh, and made me cry. Now I’m my own boss and frankly, the jury’s still out.

Bosses come in all shapes, styles, and fashions. And some are just better than others.

I recently received a question from a listener named Lisa who’s struggling with an overly critical boss. She said:

[My boss feels the need to] 'take the whip to the horses' so we can get things done. That might work for some people … but it does not work for me. I’m sensitive to criticism. I'm afraid that if I say anything about it, I'll just look like I'm whining and asking for special treatment. Or, worse, my boss will start thinking I can't handle the pressure of my job and decide to fire me. Should I talk to my boss? Just suck it up and deal with the criticism?

Lisa, I feel your pain. Anyone who listens to Modern Mentor knows I define workplace success not just by how far you climb, but how much you enjoy the journey. So let’s talk about some ways to handle the situation.

I define workplace success not just by how far you climb, but how much you enjoy the journey.

Critical boss? First, assess the situation

Your boss doesn't have the right to behave badly. But you do have some degree of control over your response to their behavior. Start by trying to get a better understanding of our boss's behavior, and then seek clarity.

Empathize with your critical boss

A few weeks ago, a colleague was short with me on a call. I was left wondering if I’d done something to offend her. She called later that day to apologize, telling me she had just missed a deadline and was frustrated with herself. She had taken it out on me.

Sometimes just imagining what the other person might be experiencing allows you to replace anger and defensiveness with empathy and recognition.

Her explanation neither excused her behavior nor changed my experience. But it did allow me to see where she was coming from. I’ve been in her position before, and I know I’m not always my best self under pressure.

Sometimes just understanding or imagining what the other person might be experiencing allows you to replace some of your anger and defensiveness with empathy and recognition. What might your boss be dealing with? Could they be feeling intense pressure from their own boss? Has your company recently lost a big account that’s leaving your boss anxious? Has your team been struggling to deliver what’s expected of them lately?

Your boss's criticism might not be about you. So, begin by understanding what might be triggering this behavior and see if you’re able to take some of your own reactivity off the table. Easier said than done, I admit, but it's always worth a shot.

Figure out what your boss is trying to communicate

When your boss delivers a message in an overly-critical way, part of your job is to separate the “what” of the message from the “how.”

On my good days, I remind my daughters that the privilege of having things comes the responsibility of caring for them, which means it’s time to clean up their rooms. On my not-as-much good days, I scream that I’m sick of tripping over their clutter (I may occasionally use a stronger word) and if they don’t clean up immediately it’s all going in the trash.

What is your boss trying to communicate? Find a way to extract that message.

This example might be an overshare, but I'm making a point. Regardless of whether the message is delivered in a thoughtful, deliberate way or an angry, critical, and potentially sweary way, the message is the same—clean your room.

Without excusing the critical delivery mechanism, I’m wondering, Lisa, if you’re able to see past the criticism to the content of the message.

What is your boss trying to communicate? Does your boss need you to hear some feedback, insight, or direction? Find a way to extract that message. Seeking clarity demonstrates a particular professional maturity that your boss won’t be able to deny when you sit down to have a conversation about your concerns.

Voice your concerns like a pro

At this point, you’re armed with a combination of empathy and clarity—an excellent foundation for a good conversation with your boss. Now it’s time to plan and prepare.

Let your boss know you’d like to have a check-in. Use language that’s typical for your company’s culture. You might say you’d like to discuss your development, have a career conversation, or just sit down for a good old-fashioned one-on-one. All of these are legitimate reasons for a meeting, so choose what feels most authentic to you.

Feel that emotion, but remember that your goal is to focus on the professional impacts of what you’ve been experiencing.

When the time comes, recognize that you might be feeling emotional about the experience you’ve been having. Who wouldn’t? Feeling judged and criticized all the time would weigh on anyone.

And while I give you full permission to feel that emotion, your goal with this conversation is to focus on the professional impacts of what you’ve been experiencing. Lean into the opportunity and not the complaint.

As you prepare to state your case, here are the key messages I urge you to transmit:

  • I’ve heard what you’ve told me (even if I don’t like how you said it)
  • I don’t like the way you’re communicating with me (but I’m an adult and will behave like one)
  • I’m not just here to complain; I have some specific changes to suggest that may enhance our relationship and the work product
  • I recognize that this isn’t all about me—you may be dealing with something as well
  • Your communication style is impacting my ability to do great work
  • I’m not asking for special treatment, just basic human respect
  • This is what calm, constructive, professional adult conversation looks like

When you’re able to deliver a message that includes (and even role models) these elements, there’s a good chance that your boss will see you not as a whiner or complainer, but rather as someone with self-respect who is boldly making suggestions to enhance culture and business outcomes.

So, what might your actual message sound like? Give something like this a try:

In our last few conversations, I’ve heard some of your concerns about [insert critical messages received, focusing on facts, not emotion] and I’ve taken that feedback. Here’s something I’ll do differently as a result. I also wondered if there are pieces of the work you feel are going well. I find my productivity tends to increase when I feel motivated and proud in addition to knowing where I need to improve. I want to be sure our I'm striving toward the best possible outcomes.

Could we start having a 15-minute weekly check-in on this project? We can plan our discussion and focus on risks, opportunities, and successes to build on. I’m happy to take the lead on scheduling and collecting any necessary data ahead of time. Would that work for you?

Of course, the language should be your own. But I’m hoping this is a helpful template.

Set and honor your boundaries

If a couple of frank conversations with your boss don’t move the needle, then you may have a hard choice to make. This is particularly true of your boss's behavior seems to be part of a longstanding pattern.

Ask yourself, and maybe a few trusted colleagues, some questions:

  • Am I the only one having this experience with my boss, or are my colleagues feeling the same pain?
  • Is there an escalation process available to me via HR, an office of the ombudsman, or even another senior leader who might advise me?
  • Is it time to start looking for another role, either internally or with a new organization?

Some of these reflection questions will help you decide what to do next. But whatever you choose, know you have the right to feel safe and respected at work. If a boundary has been pierced, don't ignore it.

These are complicated times. The job market may feel intimidating. If your relationship with your boss isn’t improving and you’ve deemed it intolerable, you don’t need to make a rash decision. But do know when it’s time to start planning your next move.

I hope this has been helpful. And I wish you the best of luck in navigating this complicated situation!

About the Author

Rachel Cooke

Rachel Cooke is a leadership and workplace expert who holds her M.A. in Organizational Psychology from Columbia University. Founder of Lead Above Noise, she has been named a top 100 Leadership Speaker by Inc. Magazine and has been featured in Fast Company, The Huffington Post, and many more.