The People Playbook with Jason Taylor
Better People Decisions. Stronger Teams. Scalable Results.
The People Playbook is your weekly guide to building high-performing teams and cultures that scale. Hosted by leadership coach and executive advisor Jason Taylor, this podcast features raw, insightful conversations with CEOs, founders, and culture builders who know what it really takes to lead in today’s world.
From mindset to execution, every episode unpacks the strategies, missteps, and breakthroughs behind exceptional leadership - and how to align your people, purpose, and performance for lasting impact.
Whether you're a CEO scaling fast, a senior leader navigating change, or a builder at heart - this is your playbook for becoming the leader your team needs.
🎯 New episodes weekly
🔥 Real talk. No fluff.
🧠Actionable insights you can use today
Because growth doesn’t start with strategy - it starts with people.
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The People Playbook with Jason Taylor
Drew Gillett - VP of Retail Marketing, Guild Mortgage
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In this episode of The People Playbook Podcast, host Jason Taylor sits down with Drew Gillett, VP of Retail Marketing at Guild Mortgage. Drew leads a high-performance marketing team supporting thousands of loan officers in the highly regulated mortgage industry, where he focuses on building trust, driving culture, developing leaders at scale, and helping people show up with clarity and confidence.
Drew shares practical leadership insights drawn from years of scaling teams and influencing large organizations. Key topics include:
- Hiring for ownership mentality and emotional intelligence over pure results
- Balancing autonomy with accountability through clear ownership, dates, and communication
- Letting go of the "how" without lowering standards in fast-moving environments
- Diagnosing underperformance: clarity, capability, or care?
- The critical role of steady emotional mindset during high-tension moments
- Giving direct, timely feedback instead of delaying hard conversations
- Helping leaders build authentic personal brands with consistency (not constancy)
- Unlearning bottlenecks as you scale, coaching the next generation, and more
Whether you're leading teams, navigating rapid growth, or developing your own leadership style, Drew's emphasis on people-first decisions, curiosity, and high standards offers actionable plays to build stronger teams and better results.
0:06 - Welcome and guest introduction
Jason introduces Drew Gillett, VP of Marketing at Guild Mortgage.
0:39 - What is the first people decision you get right before you even start to worry about results?
Drew emphasizes hiring for ownership mentality and emotional intelligence (EQ).
1:26 - What do you mean by ownership mentality?
Ownership means understanding the "why," anticipating issues, and executing independently.
1:48 - How do you decide where freedom ends and accountability begins?
Accountability starts with clear ownership and dates; freedom is in the "how," supported by ongoing communication.
3:18 - Can you tell me about somebody that came into your organization really young and you kind of saw the development?
Drew discusses qualities like seeking the "why" behind requests and high execution standards.
5:13 - As a young leader, how did you deal with being younger than some clients' kids?
Over-emphasize execution, go above and beyond, and deliver your best work consistently.
6:16 - What have you learned about letting go without lowering your standards?
Define "good" clearly with examples, checklists, and review gates to reduce hovering and anxiety-driven control.
7:13 - How important are formal performance reviews?
They should summarize ongoing check-ins; no surprises—deliver hard feedback immediately.
9:04 - What skill matters most when tensions start to get high?
A steady emotional mindset—be the calm rock for your team to avoid spreading chaos.
10:41 - How do you diagnose underperformance: clarity, capability, or care?
Test for clarity first (can they repeat goals/priorities/metrics?); then assess care (burnout, life factors) before capability.
13:30 - How do you help leaders show up authentically with visibility and personal brand?
Be consistent (not constant), focus on 1-2 key messages, use multiple channels, and set boundaries/systems.
15:42 - What's one leadership habit you had to unlearn as your role expanded?
Stop being the go-to executor—delegate and avoid becoming the bottleneck.
16:49 - If you could give young Drew three pieces of advice, what would they be?
Write things down, seek new opportunities/say yes more, stay curious.
17:50 - Do you find leading the younger generation different?
They need foundational training on "unwritten rules" (e.g., email etiquette); Gen Z is risk-averse due to their upbringing.
21:30 - What is one people-related mistake leaders repeat as they scale?
Avoiding/delaying hard feedback to be "liked"—it erodes trust and culture.
24:56 - When somebody leaves your team, what do you hope they are more capable of?
Better communication/organization, sustained curiosity, confidence owning problems end-to-end, and personal growth.
26:17 - Closing thanks and wrap-up.
