Inside the Mind of the World’s Most Optimistic CEO
Sep 01, 2025•1 hr 10 min•Ep. 258
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Episode description
For Bill McDermott, work has never been just a job.
On this Labor Day rerun of Grit, first published Jan 9, 2023, the ServiceNow CEO reflects on what he learned from his earliest jobs and how he carried those lessons from a deli counter in Long Island to the boardroom of an $80B software company.
We cover:
- Why Bill bought a deli when he was in high school — and how he competed against 7-Eleven (04:00)
- Interviewing at Xerox and wanting it more than anyone else (08:17)
- Unwavering optimism and being a source of strength for others (12:34)
- How a love of work has shaped Bill as a person (16:44)
- Facing challenges and keeping a promise to his father (22:00)
- Enjoying the present and keeping an eye on the future (30:01)
- Leaving Xerox for Gartner and learning from a tough experience (33:29)
- Sloan Kettering and Father Michael Judge (39:22)
- Following the “original dream” vs. building something new at ServiceNow (44:59)
- Losing an eye and getting a pep talk from two Medal of Honor winners (51:15)
- Why Bill started and ended his book with quotes from two Kennedys (01:01:21)
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