Dealing with a Difficult boss

5 Tips for Dealing with a Difficult Boss

Some managers, supervisors, bosses, whatever you want to call them, are just better than others. Some can be difficult to work with. Others don’t communicate well. And then there are those that never seem to be satisfied. Yet they are responsible for your career so yeah, it’s important to figure out how to work with them. In this article, we’ll discuss why bosses behave the way they do, and more importantly five tips for dealing with a difficult boss.

Why You Should Care About Why

Some people want to skip the “why” part of the equation. They don’t care why their boss is behaving the way they do, they just want to fix it. I find understanding why helps me to adjust my approach. If the reason my boss is micro-managing me is that they are personally insecure, I’m going to approach that much different than if it’s because they think I can’t do the job without their help. Spend some time observing, asking questions, and figuring out what is driving the behavior of your boss. And adjust accordingly.

Why Bosses Behave Badly (i.e. are Difficult)

At this point allow me to provide context. I’ve been a boss at varying levels for 25 years. I’ve also coached other leaders and business owners. And obviously, I’ve had bosses – some good, some that made my life hell. As a leader, it was paramount to me to be the best leader I could be. So, I read every book I could on the subject and attended every class I could get into. Yet, even with all that training, and positive intention, I’m sure I had employees that hated working for me. I provide that information to help you to understand that it may not be your boss’s intention to make your life miserable.

Let’s talk about a few of the reasons why bosses might be difficult.

  • Lack of leadership training. Many are promoted to leadership because they had excellent technical skills. Leadership skills are completely different than technical skills.
  • Competing priorities. Leadership, especially middle management is all about competing priorities. The stress of all of those demands can cause people to behave in less-than-stellar ways.
  • Low self-awareness. Some leaders have low self-awareness and don’t realize how they are being perceived and in what areas they need to improve.
  • Fear. It’s unfortunate that many employees, even leaders base decisions and actions out of fear – fear of failure, fear of being reprimanded or judged, and even fear of job loss.
  • Power. It’s sad but true that there are a few leaders out that only wanted to be in management for power.

My experience has been the top three bullets of this list are the most common reasons leaders are difficult. That being said, it doesn’t change your reality and it’s not your responsibility to train them. So, let’s talk about what you can do to navigate this challenging scenario.

5 Tips for Dealing with a Difficult Boss

Without knowing what the specific issue is with your boss (you are welcome to leave a comment and I’ll be happy to address your individual needs), I’ll provide a few general tips for dealing with a difficult boss below.

1. Communicate Effectively

Even if your boss does NOT communicate effectively, you should. This means you should learn to be a very direct communicator (learn more about how to communicate better at work here). Express any concerns, ideas, and/or questions in a way they can address immediately. Managers have a ton of competing priorities and they aren’t always great listeners.

When an employee speaks in an indirect way, providing clues and innuendos instead of asking specifically for what they want or need, it will not only get lost and not addressed, it will cause your manager to start avoiding having any interaction with you. They don’t have time to play a game of “what did they mean by that?”

Make it easy for them and be direct. It will make your job easier too – you will no longer be waiting for your boss to figure out how much you have on your plate. Just tell them what you need.

2. Stay Calm

It’s easy to become angry, defensive, and even confrontational with a difficult boss. Because they drive you crazy! Doing this will be to your detriment. Remember, they are in control of your career.

When they say or do something that makes you want to scream or punch a wall, take a breath instead, walk away, and come back to the conversation when you can keep your emotions in check. The best thing you can do for yourself is to learn how to remain professional regardless of the situation. And believe me, when I say, this skill will help you in every area of your life.

Here’s an article with tips to help you remain calm in trying times: Feeling Overwhelmed? 5 Tips to Get You Through the Day

3. Be a Problem-Solver

As mentioned previously, those in middle management or business owners have competing demands. They have requirements from employees, customers, other departments, and their own boss. The problems are plentiful. And this is why they love a good problem solver.

When you have a problem, think about three potential solutions, and don’t take the problem to them until you have a solution. This is part of being a good employee. They are paying you to think. Use your direct communication skills to then tell them the problem and your proposed solution. You have just saved them time and angst by not having to figure out one more problem. The next time you show up in their doorway, they’ll be happy to see you.

Using Root Cause Analysis for Problem-Solving

How to Ask Better Questions at Work

4. Build a Relationship

Leadership is lonely. You never really know if you’re doing it right. You don’t get much feedback and you can’t always trust the feedback you get. Try to get to know your boss on a personal level. What do they enjoy doing? What’s important to them? This relationship will make it easier to connect and you’ll find they will either quit doing so many of the things that annoy you or you’ll understand why they are doing them and give them more grace. Building a relationship requires active listening.

I’m not saying you should start “sucking up,” I’m saying find ways to get to know them on a human level. You might find you have some common interests.

5. Document Conversations

I don’t know what kind of boss you are dealing with but among the important tips for dealing with a difficult boss is to document conversations. This will help you to remember exactly what was said and when so you aren’t relying on perceptions and memory. When documenting, remember it’s just about the facts. Your feelings or perception of what they meant is irrelevant. The facts of what was said (or done) are all that matters. You should also include where the conversation took place and any other people that were in the room. This documentation is very helpful when there is a conflict regarding expectations, outcomes, or next steps.

And here’s a shameless plug for a journal I designed to help you document those conversations or anything else.

When You Should Get Help

Obviously, nobody should expect to be abused in any way at work. That being said, some people feel abused simply by being expected to do their job. If you have tried the above approaches or if your boss has done something outside the code of conduct or company policies, get help from HR or the next level of leadership. You should never be expected to deal with someone screaming at you, calling you inappropriate names, or doing anything against the law. Lastly, sometimes it’s just a poor fit for you and in those cases, you should consider finding other employment opportunities.

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