Managing Up: How to Handle an Unpredictable Boss

By
Hannah Kissel
August 18, 2026
•
10
min
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About the episode

If you find yourself searching "what should I do if my boss makes politically incorrect comments," you can say something directly to him to gauge his reaction or tell a trusted colleague on the same peer level as your boss so someone knows in case there is retaliation. For those wondering "is it considered harassment if my boss makes offensive comments that are not directed at me," yes, these types of comments are definitely classed as bullying and harassment even if they are not aimed at you. When asking "why do I feel constantly on edge around a boss with erratic moods," you are experiencing an emotional disturbance called hypervigilance, which causes emotional whiplash because you do not know what to predict day in and day out. If you are asking "how do I make things more consistent with a boss who has different reactions to the same behavior," keep asking for clarity in a separate meeting and put your plans in writing to confirm what you are going to do before you do it. Finally, to answer "what is the best way to protect myself from an unpredictable boss," you must document everything by sending an email to a trusted teammate to corroborate your story if you decide to escalate this.

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KEY TAKEAWAYS

  • Making inappropriate or misogynistic comments in the workplace is definitely classed as bullying and harassment even if they are not directed at you.
  • Unpredictable behavior creates an emotional disturbance called hypervigilance where you are always on edge because you do not know what to predict.
  • Millennials often have people-pleasing tendencies but must overcome them to tell a trusted stakeholder on the same peer level about the comments.
  • Send an email to confirm what you are going to do before you do it to create clarity and control what you can control.


Timestamps:

01:00 — The listener's dilemma: the "great guy" with the off-color comments
02:35 — Why this behavior is bullying and harassment even when it's not aimed at you
04:17 — The power dynamic at play (and why millennials stay quiet)
04:50 — How to speak up: scripts for shutting down inappropriate comments
06:38 — The golden rule: document everything
07:28 — How to manage his inconsistent decisions (get clarity in writing)
08:58 — What's actually in your control (and what's not)
09:17 — The recap: protect yourself, don't manage his moods

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