What does it mean to lead through uncertainty when the technology underneath you is moving faster than your governance, your metrics, and your comfort level? Mike Schubert digs into four things: Harvard research on why sharing uncertainty builds trust; Microsoft Agent 365 and the shadow agent problem; IBM Bob 1.0 for the COBOL/RPG world; and Jensen Huang's token consumption metric. Three stories, one thread: agents proliferating faster than governance, faster than measurement, and faster than most leaders' comfort level.

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Timestamps

• 0:00 - Intro & episode overview
• 1:30 - Segment 1: When to Open Up at Work (Leslie John / HBR)
• 7:07 - Segment 2: Microsoft Agent 365 & agent sprawl
• 14:17 - Segment 3: IBM Bob & the ghost of Microsoft Bob
• 16:28 - Segment 4: AI ROI - are we measuring the right thing?
• 21:56 - Outro

Sources & LinksSegment 1 - When to Open Up at Work

• HBR: When to Open Up at Work (Leslie John, Feb 2026)
• Book: Revealing by Leslie John - Riverhead Books, Feb 26 2026

Segment 2 - Microsoft Agent 365

• Microsoft 365 Blog - Powering Frontier Transformation (Mar 9 2026)
• Copilot Studio - 6 Core Capabilities to Scale Agent Adoption
• Microsoft Agent 365 (GA May 1 2026)

Segment 3 - IBM Bob

• IT Jungle: IBM Gets Bob 1.0 Off The Ground (Mar 2 2026)
• IBM Bob
• Microsoft Bob (1995) - Wikipedia

Segment 4 - AI ROI

• All-In Podcast: Jensen Huang at GTC 2026