27 May 2026
How Leaders Increase Trust and Connection with Chad Littlefield
Boss Better Now with Joe Mull
About
When leading a team, the natural instinct is to rely on efficiency, quick answers, and speaking more than you listen. But doing so erodes trust and productivity over the long haul.
Joe Mull welcomes Chad Littlefield, co-founder and Chief Experience Officer of We and Me, to the Boss Better Now podcast for an insightful conversation about the transformational power of asking better questions. From his early days working with teenagers in a group home and counseling in adult solitary confinement, to leading global conversations in conflict zones, Chad draws on a unique background to help leaders how to build trust and access each other's humanity.
Throughout the discussion, Chad explains why leaders must shift their focus from presenting information to actively inviting employee engagement strategies. He shares practical leadership tips for navigating remote team management, avoiding the trap of efficiency over connection, and leveraging curiosity to build psychological safety at work. He also shares compelling insights on AI in the workplace and the future of work without replacing genuine human care.
In this episode, you'll learn:
🔹 Why phenomenal bosses design meetings for "contribution, not consumption".
🔹 The magic of the second question and how it instantly builds rapport with your team.
🔹 Why "efficiency is the enemy of connection" in remote team management and how to genetically modify your meetings to fix it.
🔹 The reason you should ban the phrase "don't bring me problems, bring me solutions" forever and replace it with facilitation skills.
🔹 How to use AI tools to augment your work without losing the vital human element of "care".
This episode is for managers and leaders pursuing leadership development who want to move beyond superficial interactions and build deeply connected, engaged teams with strong workplace culture and psychological safety at work.
Episode Resources:
Chad's YouTube Channel: https://www.youtube.com/@chad.littlefield
We and Me website: https://weand.me/
We Connect Cards: https://shop.weand.me/
To subscribe to Joe Mull’s BossBetter Email newsletter, visit https://BossBetterNow.com
For more info on working with Joe Mull, visit https://joemull.com
For more info on Boss Hero School, visit https://bossheroschool.com
To email the podcast, use bossbetternow@gmail.com
#leadership #management #toxicworkculture #teambuilding #workplaceculture #conflictmanagement #employeeengagement #motivation
Joe Mull is on a mission to help leaders and business owners create the conditions where commitment takes root—and the entire workplace thrives.
A dynamic and deeply relatable speaker, Joe combines compelling research, magnetic storytelling, and practical strategies to show exactly how to cultivate loyalty, ignite effort, and build people-first workplaces where both performance and morale flourish. His message is clear: when commitment is activated, engagement rises, teams gel, retention improves, and business outcomes soar.
Joe is the founder of Boss Hero School™ and the creator of the acclaimed Employalty™ framework, a roadmap for creating thriving workplaces in a new era of work. He’s the author of three books, including Employalty, named a top business book of the year by Publisher’s Weekly, and his popular podcast, Boss Better Now, ranks in the top 1% of management shows globally.
A former head of learning and development at one of the largest healthcare systems in the U.S., Joe has spent nearly two decades equipping leaders—from Fortune 500 companies like State Farm, Siemens, and Choice Hotels to hospitals, agencies, and small firms—with the tools to lead better, inspire commitment, and build more humane workplace cultures. His insights have been featured in The Wall Street Journal, Forbes, Harvard Business Review, and more.
In 2025, Joe was inducted into the Professional Speakers Hall of Fame (CPAE). This is the speaking profession’s highest honor, a distinction granted to less than 1% of professional speakers worldwide. It’s awarded to speakers who demonstrate exceptional talent, integrity, and influence in the speaking profession
For more information visit joemull.com.
Timestamps
0:00 Introducing Chad Litttlefield
2:21 Chad's First Work Experiences
7:02 Working In Group Homes And Juvenile Prisons
12:23 Discovering The Power Of Questions And Everyday Connection
15:01 Creating We Connect Cards
17:05 Designing Meetings For Contribution Not Consumption
20:18 Psychological Safety And How We Ask About Mistakes
21:51 Flipping PowerPoint to Real Engagement
24:12 The Magic Of Asking A Second Question
27:45 Building Connection In Remote And Hybrid Teams
32:44 Collaborative Journaling
34:21 AI Tools And Protecting Authentic Human Connection
38:10 Why Caring At Work Beats AI
39:00 How Adding "So That" Can Change Your Management Interactions
42:51 The Workplace Phrase Leaders Should Stop Saying
45:07 Career Advice About Following Your Curiosity
47:15 Closing Thoughts
Joe Mull welcomes Chad Littlefield, co-founder and Chief Experience Officer of We and Me, to the Boss Better Now podcast for an insightful conversation about the transformational power of asking better questions. From his early days working with teenagers in a group home and counseling in adult solitary confinement, to leading global conversations in conflict zones, Chad draws on a unique background to help leaders how to build trust and access each other's humanity.
Throughout the discussion, Chad explains why leaders must shift their focus from presenting information to actively inviting employee engagement strategies. He shares practical leadership tips for navigating remote team management, avoiding the trap of efficiency over connection, and leveraging curiosity to build psychological safety at work. He also shares compelling insights on AI in the workplace and the future of work without replacing genuine human care.
In this episode, you'll learn:
🔹 Why phenomenal bosses design meetings for "contribution, not consumption".
🔹 The magic of the second question and how it instantly builds rapport with your team.
🔹 Why "efficiency is the enemy of connection" in remote team management and how to genetically modify your meetings to fix it.
🔹 The reason you should ban the phrase "don't bring me problems, bring me solutions" forever and replace it with facilitation skills.
🔹 How to use AI tools to augment your work without losing the vital human element of "care".
This episode is for managers and leaders pursuing leadership development who want to move beyond superficial interactions and build deeply connected, engaged teams with strong workplace culture and psychological safety at work.
Episode Resources:
Chad's YouTube Channel: https://www.youtube.com/@chad.littlefield
We and Me website: https://weand.me/
We Connect Cards: https://shop.weand.me/
To subscribe to Joe Mull’s BossBetter Email newsletter, visit https://BossBetterNow.com
For more info on working with Joe Mull, visit https://joemull.com
For more info on Boss Hero School, visit https://bossheroschool.com
To email the podcast, use bossbetternow@gmail.com
#leadership #management #toxicworkculture #teambuilding #workplaceculture #conflictmanagement #employeeengagement #motivation
Joe Mull is on a mission to help leaders and business owners create the conditions where commitment takes root—and the entire workplace thrives.
A dynamic and deeply relatable speaker, Joe combines compelling research, magnetic storytelling, and practical strategies to show exactly how to cultivate loyalty, ignite effort, and build people-first workplaces where both performance and morale flourish. His message is clear: when commitment is activated, engagement rises, teams gel, retention improves, and business outcomes soar.
Joe is the founder of Boss Hero School™ and the creator of the acclaimed Employalty™ framework, a roadmap for creating thriving workplaces in a new era of work. He’s the author of three books, including Employalty, named a top business book of the year by Publisher’s Weekly, and his popular podcast, Boss Better Now, ranks in the top 1% of management shows globally.
A former head of learning and development at one of the largest healthcare systems in the U.S., Joe has spent nearly two decades equipping leaders—from Fortune 500 companies like State Farm, Siemens, and Choice Hotels to hospitals, agencies, and small firms—with the tools to lead better, inspire commitment, and build more humane workplace cultures. His insights have been featured in The Wall Street Journal, Forbes, Harvard Business Review, and more.
In 2025, Joe was inducted into the Professional Speakers Hall of Fame (CPAE). This is the speaking profession’s highest honor, a distinction granted to less than 1% of professional speakers worldwide. It’s awarded to speakers who demonstrate exceptional talent, integrity, and influence in the speaking profession
For more information visit joemull.com.
Timestamps
0:00 Introducing Chad Litttlefield
2:21 Chad's First Work Experiences
7:02 Working In Group Homes And Juvenile Prisons
12:23 Discovering The Power Of Questions And Everyday Connection
15:01 Creating We Connect Cards
17:05 Designing Meetings For Contribution Not Consumption
20:18 Psychological Safety And How We Ask About Mistakes
21:51 Flipping PowerPoint to Real Engagement
24:12 The Magic Of Asking A Second Question
27:45 Building Connection In Remote And Hybrid Teams
32:44 Collaborative Journaling
34:21 AI Tools And Protecting Authentic Human Connection
38:10 Why Caring At Work Beats AI
39:00 How Adding "So That" Can Change Your Management Interactions
42:51 The Workplace Phrase Leaders Should Stop Saying
45:07 Career Advice About Following Your Curiosity
47:15 Closing Thoughts