Dealing with a Difficult Boss: Strategies for Senior-Level Professionals

Career Corner: Do you have a challenging boss? Take a strategic approach to maintain professionalism, preserve morale, and ensure well-being.

By: Liz Colodny
Illustration of an angry man in a suit, tie loosened, standing on top of a table and raging while men and women in business attire scramble, confer with each other, and scurry to pick up papers flying everywhere.

Over the course of our careers, most of us will have had at least one boss we consider “difficult.” Since business school, I’ve had three of those myself, and all for unique reasons.

Surveys consistently find that a good percentage of people will quit their job due to poor management or a bad boss. Some other top reasons for turnover, such as pay, could reflect lack of support from your boss. Factors that unhappy employees might cite for poor management include:

  • Lack of recognition and appreciation
  • Micromanagement
  • Poor communication
  • Inconsistent or unfair treatment
  • Lack of support and development opportunities
  • Overwork and burnout

If you find yourself in a situation you’d characterize as having a difficult boss, what can you do about it?  For senior-level professionals who are expected to exhibit a high level of competence and leadership, navigating the complexities of a challenging boss can be a daunting task. The situation demands a strategic approach to maintain professionalism, preserve morale, and ensure personal well-being. Here are some strategies that can help you effectively manage this difficult dynamic:

1. Assess the situation objectively.

Evaluate the nature and extent of the issues as objectively as possible. Avoid jumping to conclusions based on emotions; instead, gather concrete examples of problematic behavior and look for patterns. Is the problem rooted in communication style, personality clashes, or conflicting work ethics? Could your boss be responding to excessive pressures in their own role?

2. Reflect on your own behavior.

Consider how your actions and responses may influence your boss’s behavior. Are there ways you could improve communication or adjust your approach to reduce friction? Displaying adaptability and a willingness to find common ground can sometimes alleviate tension.

3. Foster open communication.

Initiate a candid conversation with the boss about your concerns. Choose an appropriate setting and time and frame your feedback constructively. Use “I” statements to express how specific behaviors affect your work, rather than making accusatory statements. For example: “I find it challenging to meet deadlines when priorities are frequently shifted without notice.” This approach reduces defensiveness and opens the door to collaborative problem-solving.

4. Seek clarification and feedback.

Request clear expectations and regular feedback. Regular check-ins can help ensure you are aligned with your boss’s and organization’s goals and can provide opportunities to address any concerns early on.

5. Build alliances and support networks.

Cultivate strong relationships with colleagues and other senior leaders within the organization. Allies can offer support, perspective, potential strategies, and sometimes intervene on your behalf.

6. Document everything.

Keep detailed records of interactions with your boss, especially instances of problematic behavior. Document dates, times, and the nature of incidents. This documentation can be invaluable if the situation escalates to a point where an investigation or HR intervention is required.

7. Manage stress and maintain balance.

Dealing with a difficult boss can be stressful. Prioritize your well-being by engaging in stress-reducing activities such as exercise, hobbies, and spending time with friends and loved ones. Maintaining a healthy work-life balance can help you to remain resilient and effective in your role.

8. Know when to escalate.

If your efforts to resolve the situation are unsuccessful, and your boss’s behavior is detrimental to your work or well-being, consider escalating the issue. Approach HR or more senior level management with your documented concerns. Be prepared to present your concerns professionally, focusing on how the situation impacts your performance and the organization.

9. Have an exit strategy.

If, despite your best efforts, the situation becomes untenable, it’s wise to have an exit strategy. Leaving a toxic work environment may be necessary for your mental health and career progression. Movement could be to another internal role or exiting to another organization. Keep your resume and LinkedIn profile updated and discreetly explore other opportunities.


Dealing with a difficult boss requires a blend of diplomacy, resilience, and strategic action. By staying professional, seeking constructive solutions, and prioritizing your well-being, you can navigate this challenge effectively. While nobody would wish for a challenging boss, navigating the situation provides an opportunity to develop critical interpersonal and leadership skills that will serve you well. Keep in mind the things that made you uncomfortable and less effective; you can summon those reflections to improve upon your own leadership competency.


About the Author

Liz Colodny is senior associate director, Executive MBA and Alumni Career Development, at the Samuel Curtis Johnson Graduate School of Management in the Cornell SC Johnson College of Business.