The empathy to challenge at the right time
October 28, 2026
Supporting someone and challenging them take different kinds of empathy, and the timing of the challenge matters.
In Part 4 of 5 of our AI Readiness conversation, I said I haven't experienced AI challenge consistently at the right time:
"The empathy required to be supportive and the empathy required to challenge at the right time [are] completely different."
And on why AI is different here:
"If there's any inconsistencies and it's allowed to survive, which AI will just lean in and let you be as inconsistent as you want as often as you want, because it's all these separate conversations."
Ask who in your work is positioned to challenge you at the right time.
Where this came from
Why a Bad Process Becomes Bad Automation — AI Readiness, Part 4Watch the full conversation this clip was pulled from.
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