TLP467: Navigate Uncertainty with Kevin Eikenberry

Kevin Eikenberry is a leadership expert with decades of experience and author of “Flexible Leadership: Navigate Uncertainty and Lead with Confidence”. 

Kevin explores what it takes to lead effectively in a constantly changing environment. He shares why being a “remarkable” leader isn’t about charisma or titles. It’s about intentional actions, self-awareness, and the ability to influence in complex and fast-changing environments. 

He challenges a common leadership trap: mistaking consistency for rigidity and explains how great leaders remain anchored in values while staying flexible in approach.

He explores why so many leaders fail to delegate, how trust and influence suffer in remote settings, and the frequent mistake of promoting technical experts into people leadership roles without preparing them for the shift. 

He also explains that leadership hasn’t changed at its core, but the growing diversity of values has shifted the context dramatically. 

Kevin explains the confidence-competence loop and why the right leadership response often lies in managing tensions, not finding balance. He encourages leaders to slow down, reflect with purpose, and make conscious choices that align with the moment’s needs  and not just their preferences.

If you’ve ever wondered how to lead when the ground keeps shifting beneath you, this episode is one to listen to more than once.

You can find episode 467 wherever you get your podcasts!

Watch this Episode on YouTube | Kevin Eikenberry on Navigate Uncertainty

https://bit.ly/TLP-467

 

Key Takeaways

[02:39] Kevin shared that he collects antique tractors and matching toy replicas. Growing up on a farm and being involved in his family’s agriculture business gave him real responsibility at a young age. That early exposure shaped how he sees leadership today: through the lens of contribution, accountability, and impact.

[05:33] Kevin believes being remarkable starts with recognizing each person's ability to make a difference. It’s about instilling confidence without arrogance and acting intentionally. Great leaders help others believe they are capable and valuable, especially in environments filled with change.

[09:40] Kevin challenges the false choice between being consistent or being flexible. He uses the image of a mature tree—rooted but able to bend—as a model for leadership today. Flexibility means changing your approach without compromising core values, especially as the context around you evolves.

[13:39] Jim asked how the growing diversity of values affects leadership today. Kevin explained that while human behavior and leadership fundamentals haven’t changed, the context around them has shifted dramatically. 

[17:35] Many leaders want to delegate but get caught in the mindset that it’s quicker to do things themselves. Kevin frames delegation as an investment, not a transaction. Building trust and capability in others takes time up front, but it's essential—especially in distributed and hybrid work settings.

[21:02] Kevin points out that organizations often promote top performers in technical roles without preparing them for leadership. He draws a parallel to sports that great players rarely make great coaches. 

[23:33] Kevin shares that to be intentional, leaders must slow down and reflect. Whether it’s quiet time during a commute or a simple end-of-day check-in, asking what went well and what could improve helps leaders stay grounded. Kevin stresses that reflection isn’t about ruminating, it’s about learning and adjusting.<