Dear HBR: · Harvard Business Review

Challenging the Boss

May 14, 2020·35 min·3 clips

Liz Kislik reveals that challenging your boss is less about courage and more about a lack of empathy.

Authority changes the room. The opening question asks why challenging a boss feels so hard, and Liz Kislik connects that fear to dependence on authority and the strange feeling of shrinking around it. That keeps the advice grounded. This is not treated as a grand confrontation. The panel talks about challenge as a way to give a boss information they may be missing. The clearest example is downtime. A listener has helped a boss's boss with data requests before, but that availability has started to look like a standing after hours arrangement. The listener set a clear boundary and said email would wait until Monday. The boss's boss called instead, turning a reasonable weekend limit into something more stressful. Promotion raises the stakes. The listener is looking for roles that would report to that same boss's boss, so mental health and future standing are tangled together. Liz starts by reading the manager generously. Maybe this guy is exhausted or anxious, which leaves room to ask questions before accusing him of overreach. Alison adds friction to that advice. She points to an HBR article on high intensity work-life balance, where people who are open about resisting constant availability can get punished for it. That matters. Bravery alone is not the whole answer when a workplace rewards always-on behavior. The panel ends up separating two problems: a boss who truly expects constant access, and a boss who assumes everything is fine because nobody has named the cost. By the close, the pattern gets wider, including how an all-hands meeting can raise merger concerns without leaving one person to carry the challenge alone.

As heard by us

A practical guide to pushing back on authority without breaking trust.

Dear HBR listens in as Liz Kislik helps Dan McGinn and Alison Beard unpack why pushing back on a boss can feel loaded. The episode's cleanest point is simple: a boss can only decide well when they have the facts they need, so speaking up is part of making work function, not a…

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Why you'd press play

When availability gets mistaken for commitment, you get a script.

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