Does your boss have unrealistic expectations?

Do they micromanage your work?

Your answer to these questions may tell you a lot about your relationship with your boss. The relationship that you develop with your boss is a crucial one and can manifest in various ways. Your boss could act like a friend, mentor and maybe even a dictator.

You might find yourself face-to-face with someone who demands a lot out of you. Demanding people are often driven and ambitious, but being this way can lead to toxic work environments.

A man standing over a cubical in an authoritative manner sipping coffee.

Dealing with a demanding boss is not easy, and I've had my fair share of them. Here are some strategies that I used as I navigated my relationships with demanding bosses.

Step 1: Determine Why They Are Like This

Determining the "why" might help you better understand how to address the issue with your boss. They might be extremely driven or they could be under a lot of pressure.

Jimmy Fallon appearing annoyed asking,

As I got to know my senior manager more, I learned that there was an underlying anxiety to their demands, preferences, and attitude. Learning more about my boss helped me understand how to have a conversation with them.

Try this:

  • Take notes of their behaviors and demands.

  • Reflect on whether or not this is an issue of external or internal pressures.

Step 2: Communicate Openly

Relationships require ongoing and open communication in order to last.

A person making a joke about communication being like a chick-fil-a drive thru, both lanes are open

Effective communication can be broken down into 3 parts:

  • Message — What are you trying to communicate?

  • Delivery — Does it make sense to deliver your message in person? Over the phone? Through text?

  • Audience — How will my boss react to my message?

True story:

During COVID, I was asked to do a number of tasks that were not part of my original job description and provide daily updates on my progress. I was visibly frustrated and decided to speak with my manager.

I created an outline of what I wanted to say, starting with what was bothering me and why it bothered me. I also wrote down why she should care that it bothered me and the impact it had on our team.

I decided that it was best to start the conversation by email and then arrange for an in-person discussion. Doing this helped me manage my frustrations and be clear with the issue.

Try this:

  • Talk to your boss.

  • When demands are made, make sure that you both discuss priorities, deadlines, and responsibilities openly so that you and your boss are clear on the expectations.

Step 3: Listen Actively

Active listening means that you're hearing and understanding what someone is trying to tell you, and that you are able to retain the information.

Person listen attentively

Use active listening to:

  • Gain clarity on the expectations your boss has of you.

  • Resolve conflicts that might occur between you and your boss.

  • Build trust.

Try this:

  • Make eye contact.

  • Pay attention to your body language.

  • Ask questions.

  • Paraphrase to show what you understand.


Your boss has provided you with some criticism during a meeting. What should you do next?

Step 4: Establish Boundaries

While work is important, your peace and happiness is important too. Protect your peace and happiness.

An employee sharing the ability to set boundaries with two other people.

Take these steps to establishing boundaries with your boss:

  1. Reflect on and understand your values.

  2. Communicate your values with your boss.

  3. Negotiate with your boss. Not all of your demands will be met, but building the framework of your boundaries is a great first step.

True story:

I used to work the night shift for a company that was open 24 hours a day. I used to receive calls in the morning from my boss to discuss events from the night before.

I quickly realized that their actions required me to sacrifice all of my downtime to accommodate their working hours. I confronted my boss and explained that my work-home life balance was suffering.

We discussed a few options such as remote meetings and daily summary emails. We eventually agreed to meet daily half an hour before my shift to talk as this worked best for both of our schedules.

Step 5: Don't Take it Personal

Having a demanding boss can make you feel extremely inadequate. For someone who is a people-pleaser, this dynamic can be difficult to deal with. This was the case when I first started reporting to my senior manager.

A woman in front of a bookshelf confidently stating,

Remember, your boss's demands and behaviors are not a reflection of you! Your performance may be negatively impacted if you start to take things personally. Be kind to yourself, and understanding of your boss.

Take Action

Dealing with demanding bosses can be extremely stressful and impact your sense of well-being. I have shared my experiences with the hopes that you'll be able to use them to improve your relationship with your boss.

Michael Bublé confidently pointing with text in the background stating

Check out the links below for more information on building and improving upon your relationship with your boss:


Your feedback matters to us.

This Byte helped me better understand the topic.

Get support to take action on this Byte