Work With a Difficult Boss? Use These Four Key Strategies to Grow and Succeed

Work With a Difficult Boss? Use These Four Key Strategies to Grow and Succeed

Having a difficult boss can make you ask yourself questions like: “Why is my hard work not good enough?”; “I’ve done so much, how can I finally get that promotion?”; or “I did exactly what my boss said and I still don’t understand how it’s not up to par.”

Difficult bosses shouldn’t bring you down. See the situation as an opportunity to try different strategies to handle your boss’s challenging personality yet still achieve your own goals.





Think like Your Boss


Take a minute to stop and think about his or her motivations, concerns, priorities, etc. Your job is to make their lives easier, so think hard about what they might like to see from you and how you can show them you’re doing quality work.

For example, make a list of items you think they might appreciate seeing on your next report. Give information your boss can share with their managers to make him or her look good. Give them project updates on a weekly basis instead of waiting for them to ask you. Showing such drive gives you higher chances of praise, appreciation, and even promotions.

Get Ahead of the Game


At this point in your career, you already know how to do your job and what your manager expects. You likely have the capability of anticipating the different types of tasks, questions, and objections your boss may surprise you with. Practicing this strategy will make you look polished and prepared, not to mention responsible for working so methodically.




Learn from Mentors and Co-Workers


Hearing what your boss is like with other people may help you get a better idea on how to work with him or her. Listening to other people’s advice and perspectives will help you understand what to do and what not to do when working with your boss. It’s essential to learn how he or she prefers to communicate (phone, email, in-person, etc.), what they like or don’t like to hear, and so on. This can help you learn from other people’s mistakes and understand how you can win your boss’s trust.





Speak Up


If you’ve tried everything and still feel puzzled about how to give your boss what he or she is looking for, voice your thoughts and concerns with them privately. Start by setting up a meeting with your boss and prepare a list of questions ahead of time. By scheduling a meeting, you show that you’re respecting their time and giving them a chance to discuss things that may help make both of your lives easier. Questions you can bring to this meeting may include:

  • What are you expecting to see in these types of projects?
  • What can I do to give you exactly what you’re looking for?
  • How do you measure success?
  • What keeps you up at night and what can I do to make your life easier?

The key is to be polite and show that you care. Your boss has a heart and hopefully they will be grateful to you for coming to them with these questions. This strategy can make you stand out from the crowd and show your boss your incredible determination to succeed.

Using these strategies may make a world of difference for you. By doing some deep thinking, planning, and communicating, you’ll feel a lot smarter and better prepared on how to work with your boss. If after applying these tips you still feel stuck and no progress has been made, consider getting help or advice from HR. The goal is to do everything in your power to get a better handle of your boss’s difficult personality. Try not to lose focus and do your best to prove yourself in this job and all other jobs moving forward.