Confidence Is Contagious, and So Is the Lack of It - #143 - Carly Greenwald

Episode Summary

Carly Greenwald has spent more than 20 years in IT leadership and change management, leading global transformation work that connects new technology with the people who actually use it. In this episode she and host Justin Lake dig into why frontline adoption succeeds or fails, and they keep landing on one word: confidence. The conversation moves from the frontline worker handed a change they never asked for, to the customer across the counter, to the project team that has lived inside the implementation for months. Carly argues for honesty over polish. Do not sugarcoat the change, do not oversell benefits that are not there, and do not save feedback for a big reveal that rarely goes as planned. Her sharpest point reframes who needs confidence: it is not only the frontline. Project teams often delay user feedback because they are not yet confident in what they are building, and bringing users in early, in small increments, raises everyone's confidence at once.

Key Topics

• The underrepresented frontline voice
• Unwinding old habits, not just teaching the new way
• Honesty over sugarcoating the change
• How frontline confidence transfers to customers
• The project team's own confidence
• Early, incremental feedback instead of the big reveal
• Being realistic about what change asks of people

Episode Chapters

00:00 Introduction to Change Management in Technology
01:12 Consequences of Poor Technology Adoption
04:28 Engaging Frontline Workers in Change
07:34 Overcoming Resistance to Change
10:09 The Impact of Change on Customer Experience
11:38 The Role of Change Managers
14:22 Building Trust and Relationships
17:20 The Isolation of Frontline Workers
20:14 The Importance of Confidence in Frontline Teams
23:05 The Ripple Effect of Technology Changes
26:06 Connecting Confidence and Customer Trust
37:51 Understanding Change from the Frontline Perspective
44:01 Building Confidence in Change Management
51:43 The Importance of User Feedback in Implementations
01:01:19 Realistic Expectations for Digital Transformation

About Carly Greenwald

Carly Greenwald is an IT change management and user engagement leader with more than 20 years of experience in IT leadership and change management. She specializes in global transformation initiatives that bridge technology and people, helping organizations move past implementation into genuine adoption with a practical, people-centered approach.

Resources

• Carly Greenwald on LinkedIn: https://www.linkedin.com/in/carly-greenwald-7b74b813/
• Skyllful: https://skyllful.com
• Frontline Innovators Podcast: https://skyllful.com/podcast