How To Deal With a Difficult Boss

How To Deal With a Difficult Boss

One of the biggest challenges we can face at work is how to handle a difficult manager or leader. Whether the issue is micro-management, a boss who is overly demanding or overly critical, a leader who doesn’t listen, has a nasty temper, enjoys disrespecting colleagues, or harassing them, having to work with a difficult personality can upset the ecosystem and culture of a business as well as cause valuable talent to leave or quietly quit. Sometimes the situation can’t be fixed but there are strategies to employ that can alleviate the issues.  So what are the best ways to deal with a tricky boss?

  • Try To Understand Them Sometimes taking a step back and employing empathy and understanding of the executive’s perspective, personality, culture, experience and communication style, means we can begin to recognise the reasons behind their behaviour.  From a place of understanding, you might be able to negotiate a mutually beneficial solution and communicate effectively to ensure you are both more aligned.
  • Identify Their (And Your Own) Triggers Knowing what their triggers are may help you anticipate their actions and adjust your approach accordingly. Equally recognising your own trigger points might be as important.  Both will enable you to develop a more effective strategy for handling difficult situations and hopefully to build a productive working relationship with the executive. Difficult behaviour often originates from inherent personality traits that become amplified with pressure and stress. If an executive is under immense pressure, helping them to delegate so they can focus their time and responsibilities better may well relieve some pressure and ease the effects of their behaviour.
  • Identify The Root Cause Of The Problem And Create A Strategy Often what seems like the issue is actually an unconscious cover for what really is going on. Gather relevant information if you can, and determine the impact of the problem.  Consider the executive’s perspective and concerns and different options for addressing the problem and identify potential risks and benefits of each option. By taking both an emotionally intelligent and structured approach to problem-solving and being proactive in addressing issues, you can minimise the impact of difficult situations and maintain productive working relationships. Develop a strategy and take action to resolve the issue. Work towards a mutually beneficial solution and communicate effectively to ensure that everyone is aligned. Be proactive in addressing issues before they escalate.
  • Stay Calm and Professional Maintaining a high level of professionalism, even in really challenging situations, is essential. This means being prepared, punctual, and reliable so the tables can’t be turned, and blame placed at your door. It is also critical to maintain confidentiality and have respect for privacy. Remaining calm shows that you are capable of handling challenging situations and maintaining a level of composure.
  • Manage Expectations This means setting realistic goals and a timeline and negotiating priorities. Ensure the executive has a realistic understanding of the time and effort required to achieve their goals, outlining the necessary steps and communicating any potential roadblocks. Clarify roles and responsibilities and avoid overlaps or gaps in responsibilities. Be flexible and adaptable in responding to changing priorities.
  • Encourage Effective Communication Be clear, concise and listen to concerns. Use positive language and focus on finding a solution rather than placing blame.  Remember that you are in control of your own emotions and reactions.  It is often possible to build trust and credibility with the difficult executive and work towards resolving issues in a productive manner. If things get bad, keep factual notes of incidents and their repercussions – these can be very important later on.
  • Handle Difficult Situations with Purpose and Poise. Avoid getting into a pointless argument. Having understanding and insight makes it much easier to respond rather than react. Remaining calm in difficult situations means you are more able to think effectively on your feet otherwise you may trigger your “freeze, fight, flight or fawn” response. When this happens, you may become very sensitive and reactive with your emotions heightened; you may not regulate yourself very well, and may perceive judgment or a negative response in an exaggerated way. Instead, be prepared and show a willingness to move forwards by offering up solutions that work for both sides.
  • Build a Positive Relationship Establishing trust and rapport and being proactive in identifying potential issues and addressing them before they become bigger problems helps to reduce tension and conflict. Perhaps you can find common ground and shared goals and look for opportunities to collaborate.  Show empathy and understanding. This also helps create an environment of mutual respect and trust for a more positive and productive working relationship, even in challenging situations.
  • Adopt Self Care Taking care of your physical, emotional, and mental health helps to ensure that you are able to perform your job effectively and manage stress which is an essential aspect of handling conflict and difficult colleagues. Take regular breaks to relax and sleep and exercise regularly. Call upon your support system outside of work, for instance from friends or family. Avoid overworking or pushing yourself too hard in an attempt to resolve the situation at work. Develop a positive mindset and attitude. By taking care of yourself, you can be more effective in your job, reduce stress, maintain a balanced sense of reality, and improve your quality of life. Know your worth and remember that it’s not your job to ‘fix’ the other person.
  • Seek Support From Colleagues Or A Mentor If Needed. If the situation feels too toxic, don’t feel you have to deal with it alone. Consult with other team members or a mentor for advice. You may need to communicate what is going on with other executives and stakeholders, and if the issue hasn’t been resolved, ask for a review of the situation. Ultimately you may have to withdraw entirely. We all spend a great deal of our time at work; if it’s miserable then we have to ask ourselves if it’s worth it or whether there is a better place where our worth is valued and nurtured.


Thom Dennis, CEO  Serenity in Leadership


About The Author


WORKSMARTPA – NEW IDEAS, NEW FRONTIERS The year 2021 sees our business celebrate 21 years of - a community supporting office professionals since our very first newsletter way back in May 2000. As we look forward to greet a new world of change beyond the pandemic, we are extremely excited to announce a new brand; a new look; and some new directions for our much loved, long-standing web site and communities to explore. It is time for change. To better reflect now what we do best for you, we have a new brand, web site and activities – a new name and web site that will be full of new ideas for a new business age and new working trends as we all seek to grow, expand and explore new frontiers.

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