Think managing people is hard? Welcome to the brave new world of leading humans and machines in co-existence.

Last year, Clara Shih, the founder of Hearsay Systems, was taking part in a routine visit with one of her insurance industry clients in San Francisco. Hearsay works with more than 150,000 financial and insurance advisers, providing them with artificial intelligence–driven tools to improve client relationships and workflow processes. This particular visit was to a small firm with four employees—two of whom did nothing but follow up on delinquent payments and policy renewals. The approach, involving numerous phone calls that were never returned, was not only unproductive, but also laborious and tedious.

During the visit, Shih and her team demonstrated a new A.I.-driven tool that digitizes manual customer-outreach processes by sending a text to dozens of customers reminding them of overdue bills, instead of calling each one. As they explained the tool’s uses, one of the advisers, a middle-aged man, started to cry. For a moment, Shih and her colleagues feared the adviser thought their

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