39. From Medieval History to the C-Suite with Debbie Plager

from Scrappy but Successful [Consultant's Personalities When No One's Watching]

Debbie Plager, Founder and CEO of The Plager Group, joins the show to talk about how a medieval history degree turned into a 25-year career in corporate talent leadership and now a coaching and organizational strategy firm. Debbie shares the story of temping for Anderson Consulting, discovering change management, and eventually helping HUB International win a Stevie's Gold Award for Best Employer. She and Jack dig into why teams (not individuals) are where real business transformation happens, her sweet spot serving $100M-$700M middle market companies, and how she is scaling from 1:1 coaching into a vetted team coaching model. Then it's a scrappy vs sophisticated lightning round covering everything from lap desks to asking for referrals. Chapters: Chicago Roots and the Scrappy Intro (00:00) Bootleggers, Mathematicians, and Zero Entrepreneurs (01:51) Medieval History to Anderson Consulting (04:21) Serf to Yeoman: Finding Change Management (05:36) The Best Employer Award and Summer Camp During COVID (12:59) Why Teams Are Where Work Happens (32:24) Lightning Round Begins: Scrappy vs Sophisticated (32:57) Scrappy Early Days and Saving the Marriage with a Cleaner (35:04) LinkedIn Only: Scrappy Marketing That Worked (36:04) Finding the $100M-$700M Sweet Spot (38:41) Final Verdict and Where to Find Debbie (44:36) Guest Links: Website: https://www.theplagergroup.com/ LinkedIn: https://www.linkedin.com/in/dsplager/ Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Episode metadata supplied by the publisher feed · Published Jul 12, 2026

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39. From Medieval History to the C-Suite with Debbie Plager

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This episode was published on July 12, 2026.

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