Career Success

How to Deal with a Difficult Boss

By EverwiseFebruary 18, 2015

On the Everwise Answers forum, our community of experienced mentors give advice on the sorts of business cases, dilemmas and questions that our high-potential protégés frequently encounter. These are expert opinions. For more business best practices delivered right to your inbox, sign up here.


Question: Your new coworkers just informed you that it can be difficult to work with your soon-to-be boss. How can you form a good relationship with your new supervisor? Everwise mentors share their advice on the situation.

Max has recently started at a new position in his company. His new coworkers have warned him that his boss can be difficult and he wants to start off on the right foot and establish a good rapport. What can Max do to develop a good relationship with his boss?

Here’s a summary of our mentors’ best advice from the discussion on the Everwise Answers forum.

1. Take a Step Back

During the interview process, Max should have understood a bit about his boss and decided if he could work with him or her. At the same time, his boss determined that Max was a good fit, an assurance that Max should remember.  “Max was hired by this person because he or she saw above average qualifications in Max, so that is a common ground and starting point,” points out medical marketing expert Myron Troschuk.

His new manager is also human and can’t please everyone. Marketing manager Amy Little reminds Max to “remember that managing people and expectations is extremely challenging, and the stress that comes with a top-of-the-food-chain role will undoubtedly have a negative impact on someone’s character.” People are flawed and no manager will be perfect. Employees must adjust to the unique working style and personality of every new boss.

2. Form Your Own Opinion

Although it’s important for Max to listen to his coworkers and consider their input, he can’t base his opinion solely on what others think. “It’s fine to get the feedback from your coworkers about your manager, but you need to establish your own unbiased opinion of your manager,” emphasizes manufacturing engineer Ernie Rodriquez.

Max should realize that “difficult” means different things for different people. “For some employees, a ‘difficult’ manager is simply someone that holds them accountable for doing their jobs, which means having to put more effort into something than they wish to do,” counsels HR expert Sharon Stover. Technology consultant Jay Annadath adds on that “‘difficult to work with’ could be a high expectation factor which is not bad at all.”

It would be better for Max to remain unbiased and form his own opinions based on time and personal experience.

3. Consider the Source

Why are Max’s coworkers telling him that his new boss is difficult? “This can be a very political group where his coworkers are trying to get him on their side,” advises entrepreneur Kenneth Ng. Max should consider the coworkers input not only as information about his boss, but as information about his colleagues. He needs to evaluate his coworkers’ motives because his relationship with them is just as important as his relationship with his new manager.

“High-performing professionals typically don’t engage in managing down the boss, so I would be cautious about trusting information from these coworkers,” warns healthcare coach KrisAnn Piazza.

4. Focus on Performance

The best way for Max to establish a good relationship with his boss is to be a good employee.  “If your boss did not already tell you, ask him or her to share with you their expectations, values, vision, goals, and even their hot buttons to avoid. Ask how you can help him or her meet their goals,” recommends Shannon Pickering Brown, founder of her own coaching company. By having a clear understanding of what his new manger is looking for, Max can take the right steps to meet those needs. This should start the relationship off on the right foot and help build a good rapport.

Max’s positive performance will also reflect well on his manager. “The best advice I ever got about this situation was to do my job and think about how I could make my boss’s job easier. If you’re one of the guys making your team look good, your manager’s going to know,” proposes restructuring expert Larry McKinley.

Max could also see this as an opportunity to grow. “I personally like to work for people who set the bar very high,” says banking strategist Ali Soheil. “This way I am always challenged and learning. Sometimes our coaches or boss may have unrealistic expectations. That is also okay. That is not uncommon. That is why we ask questions, share our thoughts in a constructive way and table the facts.”


There is plenty of great guidance available about these sorts of challenges, here are a few suggestions:

The Mentors

Thanks to the Everwise mentors for their ideas, and to all the others who shared their recommendations on the forum.

  • Myron Troschuk (Illinois) Nation account manager at Bowman Mfg Co Inc, expert in medical sales and marketing
  • Amy Little (California) Field marking manger at Infoblox, expert in marketing, lead generation and sales management
  • Ernie Rodriquez (Wisconsin) Senior manufacturing engineer at InSinkErator, expert in high volume automated manufacturing experience and project management
  • Sharon Stover (Maryland) CEO of LifeLogics, Inc., expert in human resources and coaching and development to improve team performance
  • Jay Annadath (Pennsylvania) Found and CEO of Better Minds Consulting, LLC, expert in technology consulting, requirement analysis and predictive analytics
  • Kenneth Ng (California) Founder of Sticktuitive, Inc., expert at agile methodologies for software development
  • KrisAnn Piazza (New York) Executive healthcare coach at Studer Group, expert in healthcare communications and leadership coaching experience
  • Shannon Pickeing Brown (Texas) Founder of Boss Lady Coach, LLC, expert at factoring career, personal and relationship goal achievement
  • Larry McKinley (Texas), former executive at Toppan Photomasks, expert on turning troubled organizations towards excellence
  • Ali Soheil (Canada) Managing Director of Global Delivery & Strategy at the Bank of Montreal, expert in talent development




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