OhHello with Jeremy Bloom OhHello Ep. 120 Brad Jaehn on Mentorship, Leadership, and the Future of Work
Mar 31, 2026
Brad Jaehn, a 30-year digital and tech leader (Orbitz, GoGo, McDonald’s), reflects on being fired over mentoring and why human connection matters in leadership. He discusses organizational investment in people, the role of AI alongside human guidance, and the challenges and skills needed to lead distributed teams. Short, candid, and thought-provoking.
AI Snips
Chapters
Transcript
Episode notes
Termination Over Two Hours Of Mentoring
- Brad Jaehn was terminated after being accused of holding a second job for spending two hours a month mentoring people outside work.
- The mentoring was unpaid, the money was donated, and Brad says he simply forgot to send an email notifying HR before being fired.
People Development Is Often Lip Service
- Many companies put 'people development' on slides but rarely invest in real leadership development or create learning organizations.
- Brad argues real investment means external help, accountability, and programs focused on leaders, not compliance training or self-directed tuition.
Mentorship Looks Costly But Creates Intangible ROI
- Leaders often view mentorship time as lost productive hours because ROI is hard to quantify on a balance sheet.
- Brad counters that intangible intrinsic ROI — lower turnover and employee happiness — is measurable and critical long-term value.