Epsiode 352

In this episode of UNSCRIPTED, host Sarah Nicastro sits down with Greg Crumpton, VP at ServiceLogic and founder of DeepKnowledge, to explore how curiosity and contrarian thinking drive innovation, why respecting local expertise beats corporate control, and how modern leaders can build cultures where people actually want to stay. Whether you're navigating acquisition-led growth, scaling teams across generations, or struggling with the shift from command-and-control management, this conversation is packed with hard-won wisdom on trust, mutual respect, and what it really takes to lead today.  

This is part two of a two-part episode; listen to part one here.  

What You'll Learn

This episode explores leadership through a practical, people-first lens. Key takeaways include:

• Why asking “why” is not a sign of disrespect, but a signal of curiosity and engagement
• How misinterpreting questions from younger generations creates unnecessary friction and talent loss
• Why apprenticeship, coaching, and long-term development matter more than short-term productivity
• How leaders can move from command-and-control to trust-based, human-centred management
• Why flexibility, listening, and personalised work arrangements are becoming competitive advantages
• How empathy, not authority, is emerging as a defining leadership trait in today’s workforce

About the Guest(s)

Greg Crumpton is Vice President at ServiceLogic and founder of DeepKnowledge. With a career spanning hands-on technical work, business ownership, acquisition-led growth, and executive leadership, Greg brings a rare blend of operational credibility and human insight.

He is also the author of two books focused on leadership, culture, and the lessons learned through real-world experience - what he calls “earned scar tissue” that he now shares to help others avoid learning the hard way.

Follow Along

1. Curiosity vs. Disrespect: Reframing “Why”
00:01:50 – 00:06:07
Greg explains why younger generations asking “why” isn’t contrarian behaviour - it’s how they’ve learned to navigate the world. Leaders who mistake curiosity for insubordination miss opportunities to teach, connect, and build trust.

2. Challenging the Status Quo Without Ego
00:07:25 – 00:11:10
Both Greg and Sarah unpack why industries that cling to “this is how we’ve always done it” struggle to evolve, and why good ideas can come from anywhere, regardless of age, title, or tenure.

3. People Matter More in a Digital World
00:11:10 – 00:14:04
As technology and AI accelerate, Greg argues that human connection becomes more, not less, important. Tools should elevate people, not replace them.

4. Building a Workplace People Choose, Not Tolerate
00:14:48 – 00:18:53
From flexible time off to personalised career paths, Greg challenges one-size-fits-all employment models and explains how companies can become magnets for talent instead of revolving doors.

5. Leadership Has No Shortcuts
00:19:57 – 00:24:39
Real leadership requires time, presence, and emotional investment. Greg and Sarah discuss why policies can’t replace human judgement and why leaders must understand the real lives behind job titles.

6. Empathy as a Learned Skill
00:32:56 – 00:38:03
Greg reflects on the life experiences that shaped his leadership philosophy, from loss and hardship to moments where small decisions profoundly changed others’ lives. Empathy, he explains, is built not assumed.

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