6 Steps to Deal with a Challenging Boss

By Jaime Lisk

We’ve all experienced tough work environments. Whether it’s a crushing workload, impossible deadlines, conflicts with coworkers, or a manager who isn’t making anything easy, there are plenty of solutions through it. But if you’re dealing with the latter, which, let’s face it, is often the cause of many of the former, take heart: there are simple actions you can take to regain your control and “manage up.”

Here are a few tips to help if you’re experiencing a difficult work environment caused by a manager:

Remember, your identity is not defined by your job.
Realize at the end of the day that you are more than your job and your identity is not solely defined by your job or position. Stop, take a breath, and look at the bigger picture. Taking a step back to gain perspective on your work situation allows you time to realize that your boss being a jerk is not the end of the world. You are more than who you are at work and your life is more than what happens to you at work.

Have the confidence to be curious.
It’s great to ask questions to gain clarification and to challenge your manager (respectfully). If you feel like you need to “manage up,” you are likely not getting clear deadlines or expectations on your work or project. By speaking up and asking detailed questions, you will gain clarity on what is expected of you and increase your chances of being able to deliver. It takes confidence in your abilities to do this. I challenge you, the next time you’re with your boss talking about a project or assignment, force yourself to ask three more questions before the meeting ends.

Focus on what you have control over.
Taking time to re-frame the situation and defining what you have control over as an individual contributor helps relieve stress and focus on what you need to do next. This doesn’t give you an excuse to be lazy and say “that’s not my job,“ but the reality is that in work situations we are not 100% in control. Instead, you can focus on those items or spheres of influence that you do have to create results and do the best job you can based on your position.

Exhaust your resources and do your research.
If you have been given a decent amount of responsibility and people are counting on you to get things done, make sure you’ve done your due diligence. Your boss won’t be impressed if you come to her with a question that she’s already answered via email or one you could have found in documents, training, or by asking another team member. If you take the initiative to answer your own questions when you can, then when a big scenario comes up where you actually need advice, guidance or answers, your boss will be more likely to listen to you because she knows you genuinely need assistance. This builds trust and shows initiative, plus it will save you time and make you feel empowered!

Come prepared.
For those with a busy or results-oriented boss, always be ready to present solutions and options for the problem you are trying to solve. This type of boss does not want to hear all the details or the background information; he or she usually just wants the resolution. (Although you should be prepared to provide additional facts and data when necessary, so it’s important to have that ready.) Coming to your boss with solutions, requesting only feedback and direction, or a stamp of approval will go a lot further in terms of showing your initiative and the effort that you’ve put in prior to coming to your boss with a problem.

Ask when you need it.
When you need your manager’s help, such as an email or an action to get the ball rolling on something that’s very important, be open and vulnerable when you approach them. Let your boss know that their authority and the respect that people in the organization have for them will go a long way in getting the project moved along. Don’t forget to reassure your manager that although they are starting the conversation or putting in a good word, you will be the one to carry the load and take responsibility going forward.

Remember, difficult work situations are not forever. We experience many types of management styles and work cultures throughout our careers. The more you build your skills to navigate these situations, the easier they will become.

Jaime Lisk is a certified leadership trainer, coach and HR advisor. Through her leadership training program, RealTime Coaching™, she teaches managers how to be effective coaches, navigate difficult situations, and inspire the best in their teams. Email her at jaime@price-associates.com.