For as long as people have had jobs, there have likely been supervisors driving them nuts—maybe just a little, but possibly a lot. Actors Jamie Foxx, Jennifer Aniston, and Jason Bateman even headlined an all-star cast in the now-iconic 2011 movie “Horrible Bosses” that took the concept to the extreme. Rather than go there, we asked Westchester-based human resources Kerry Flynn Barrett for her best how-to-deal advice.
Let’s say you find yourself frequently butting heads with your boss. What’s a constructive approach?
To find a path forward, try to identify the core disconnect. For instance, are deadlines being missed? Has the job description changed? Are expectations unclear or shifting? In other words, start with clarity; don’t immediately label your boss a micromanager or assume she has it out for you. Send a detailed email or request a meeting to focus on specific issues or behaviors and any recent changes, such as changes in work hours or deadlines. Afterwards, send a follow-up note outlining agreements, so a record exists of what was discussed and decided.
Any communication tips to avoid confusion?
Keep writing clear and emotion free. Confirm deadlines and checkpoints, both during and after meetings. Document everything. This advice doesn’t just apply to dealing with a tough boss—it’s a great across-the-board work habit. If you sense specific patterns, consider seeking feedback from colleagues, provided you can keep it professional without veering into venting. Sometimes, others have found solutions that you can learn from.
How should employees approach situations where they’re expected to be available outside of office hours?
Politely and professionally, set boundaries. If a boss expects you to reply to emails late into the night, respond by focusing on the work rather than the timing. For example: “Was there anything incomplete that you needed?” Instead of arguing about hours, highlight your reliability and completion of tasks within appropriate timeframes. Always keep language non-confrontational.
At what point should someone escalate an issue to HR?
If the situation involves harassment or illegal behavior, go to HR immediately. Otherwise, first try to resolve the issue yourself, by collecting information, documenting your efforts, and considering input from trusted colleagues. Ideally, at that point, you can approach someone in HR to act as a coach and ally, offering confidentiality (unless a law is broken) and guiding you in next steps.
How would you suggest an employee broach the subject of an overall difficult relationship with their boss?
Use ‘I’ statements rather than ‘you’ statements to avoid sounding accusatory. Think along the lines of, ‘I’ve noticed deadline changes and would like to know how I can help us meet goals.’ Keep the conversation positive and collaborative.
What about cases where nothing seems to work and the relationship with a boss is irreparably damaged?
Sometimes, despite your best efforts, personalities simply don’t mesh. In those cases, it’s worth considering a lateral move to another department if that’s an option, or searching for a new job. For your own mental health, update your resume, network through LinkedIn, and remind yourself that the best time to job-hunt is while you’re still employed.
Human resources pro Kerry Flynn Barrett—owner of Flynn Barrett Consulting in Pound Ridge—tackles questions about workplace procedures, policies, and potential issues.
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