5 Types of Bosses and How to Deal with Them

work appropriate outfit for a casual office

Military Jacket | Striped Peplum Top (only $35, also loving this one for $30!) | White Skinny Jeans | Similar Brown Mules here and here | Fringe Tote | White Beaded Earrings | Tortoise Sunglasses

If we’re being honest, no job is cupcakes and rainbows every day. Not even blogging. Although I like to stay grounded with my day job. There are always uncomfortable situations and difficult people. One of the most challenging parts of having a career can be your boss. So let’s talk about 5 different types of Bosses and how to deal with them.

1. My Way or the Highway

Have a process at work that is inefficient or prone to errors but your boss isn’t open to alternatives? Have you ever tried to suggest an improvement but somehow, its discarded? Maybe you AND your peers have banded together to do that only to find out your boss took that advice and just tossed it in the trash.

How to deal: It’s frustrating. Sometimes you just want to scream. Gather your facts and craft your explanations well. Know what you’re talking about and remove emotion from all conversations. Build the relationship (this is a common theme in this post and careers in general). If the current process fails, don’t call it out publicly. Respect your boss enough to discuss one on one or as a smaller group. Gently suggest your proposed change slowly becoming a trusted resource. By doing this over and over (mega patience needed) eventually, your boss will come to you for advice before he/she puts something into practice. It may take 6 months or even a year but, you’ll see some movement.

Another tactic is to utilize mirroring to help him/her figure out a different approach on his own, making him think it’s his own idea (I also do this with Matt). If he asks you to do some task that isn’t the best way, mirror him. For example, if he asks you to print 10 copies of a presentation that’s being distributed digitally, ask “10 copies”? You’re giving him time to rethink his ask. He won’t respond with the same thing he initially asked. Continue this tactic until you get to a reasonable compromise or the response you want.

2. Insecure

The insecure boss manifests in tons of different ways. It depends on the person and also whether they’re male or female. Remember when you worked 80 hour weeks to pull together that huge project and your boss took credit for it? What about when your boss didn’t invite you to a meeting with the CEO even though you were the expert on the meeting topic? Or the boss that is quick to say “no that won’t work” when you have a new idea? Your boss may feel insecure in his or her position. Or worse, unqualified or not in control. There may be backlash for you as the employee that may be unbearable even.

How to deal: Patience and compassion. Understand that not everyone has the confidence of a Corrine from The Bachelor. Be supportive of your superior while helping him/her be more comfortable in his/her role. Teach them what they might not know. Walk them through your thought process. Gently remind them of things they may have forgotten. Teach them to stand on their own, so to speak.

Approach errors or difficult situations with caution as they can overreact easily because of their insecurities. When you’ve built up the relationship, have a conversation to help them see how the things they do, affect you.

Having been in a role where the people on my team knew more about the details, I always kept an open mind. I asked a million questions to show how much I wanted to learn, listened to existing problems, and gave credit where credit was due. That was what worked for me instead of being insecure.

3. The Yes Man or Woman

This boss just wants to be liked by everyone. He or she is a classic people pleaser. A “yes man” or a “yes woman”. Sometimes, those yeses get you into trouble. Whether you have to do more work or your boss seemingly doesn’t have your back because he/she’s just being nice, it can be frustrating. This is the type of boss you want to grab a drink with but may also resent when he doesn’t stand up for you.

How to deal: While you’re great 95% of the time, there may be some days where you find yourself searching LinkedIn’s job board. Especially when there is a difficult situation that arises where you need him/her to take a stand. When that happens, be honest with yourself. Ask yourself how your boss’ people pleasing is affecting your work (not just on a personal level). Have a conversation with your boss and be honest. Explain how you feel in a calm and logical way. While you may not see results overnight, he/she will respect you more and eventually you’ll see some movement.

4. Micro-Manager

If you’ve ever been hovered over while you’re trying to work, had to create a status tracker for all your work, or have weekly one on ones where you go over everything you’re working on, you’ve got a micro manager on your hands. This type of boss might hold a Monday morning meeting where you have to run through each and every member of your team’s to do list. Your boss is digging into the details and asking for specifics during what results in one of the most useless and painful ways to start the week. It’s neither effective, efficient, nor relevant. Maybe the boss that casually swings by your desk 15 minutes before it’s time to leave to make sure you haven’t ducked out early?

How to deal: Any way you look at it, this behavior is just plain annoying. It makes you feel like you’re in grade school even though you’re an adult. Sometimes this behavior is the result of a boss’ personality, other times just their newness to a management role. It’s a long process but what I’ve found to be most effective is to be patient and prove yourself. Demonstrate that you are dependable and have your stuff together. Start building a relationship and testing your boss’ trust level. Ask if you can take on a project he or she would normally have done. It might feel like you have to pry something out of his or her hands but push through. Communicate up: provide updates status/deadlines without being asked. Once your boss trusts you, the micro managing will decrease. When you’re comfortable enough with him/her, you might even try bringing it up in one of those one on ones. Tactfully, of course.

5. Pervert

Rather than ignore the issue, let’s just acknowledge that inappropriate things do happen in the workplace. As a female in male dominated fields, this has happened more than college grad version of me would have expected. Unfortunately. We all know when something crosses the line. It’s like a sixth sense. That ultra creepy comment or an unwelcome touch on the arm that just sends shivers down your spine. Such as, “hey why don’t you take off your coat before our [one on one] meeting?” Or the blatant up and down stare when you walk in the door. Gross.

How to deal: Shut it down. Keep it professional (that includes what you’re wearing too). Talk business and business only. What you did this weekend is off limits. Save it for your office besties. Keep track of all inappropriate comments and document them to your HR department. As uncomfortable as it may be to have the initial conversation, HR is there to help. If you’re worried about the backlash, it can happen. Retaliation is also grounds for being fired. Document that too. At the end of the day, if he treats you differently, he knows he did something wrong and is just upset he got caught. Just make sure to document everything you think is relevant with Human Resources. It’s a very grey area but eventually, he’ll get his.

Hopefully these tips were helpful! Having a career isn’t easy. There will always be people that are difficult to deal with. Be patient, keep calm, and use your head. Vent to your work besties or your real life besties (just try not to bring that energy into your marriage or relationship). And remember, worst case, you get a new job.

PS. This outfit is definitely something you could wear in a casual workplace! The top is high cut and can be pared with so many things. I also wear this military jacket ALL the time. I know you guys have seen it on Instagram stories! Out of all the military jackets I own, this one is my favorite. The fit and the structure are hard to beat. It’s really fun to create some preppy looks with too! It must also be the week for these white skinny jeans because I wore them in both Monday’s and Tuesday’s post!

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16 thoughts on “5 Types of Bosses and How to Deal with Them

  1. I’m so glad you mentioned the Pervert boss type because it happens too often than most people would think but no one talks about it!

  2. I love this post! So important to think through how you can slowly make changes even with super frustrating bosses. Thanks for sharing stuff like this!

  3. I’m loving this outfit! and I’m thankful to have a really great boss at this point in my career

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