Leading Through Change: The Path Forward is Through

In this engaging episode, Louie Celiberti, Managing Director and Head of Software Engineering at Guggenheim Partners, shares his insights on leadership through uncertainty, building cohesive teams, and navigating generational differences in the modern workplace. Through LEGO models, Louie demonstrates powerful concepts around servant leadership, embracing risk, and the cultural shifts happening in technology teams.

Show Notes with Timestamps

0:23 – First Build: Best Team Experience (1:35)

* Louie models effective team dynamics with emotional bridges and servant leadership

1:38 – Second Build: Worst Team Experience (1:19)

* Contrasting model showing disconnected perspectives and helicopter leadership

2:59 – Third Build: Leading Through Uncertainty (1:25)

* The change model featuring steps, landmines, and the power of optimism

4:21 – Deep Dive: Embracing Risk (1:49)

* Exploring what it means to lead teams through challenges and uncertainty

6:10 – Teaching Risk Navigation (2:30)

* How leaders can help individual contributors embrace challenges and learn from failure

8:40 – Generational Workplace Changes (3:10)

* Harnessing the strengths of different generations rather than focusing on conflicts

11:50 – Bringing Generations Together (1:33)

* The empathy and mutual mentorship required to blend diverse perspectives

14:02 – AI and Cultural Shifts (1:28)

* How AI is compressing perspectives and requiring broader collaboration across departments

15:54 – Cloud Lessons for AI (1:36)

* Learning from past technology adoptions to avoid similar pitfalls

17:56 – Understanding What Motivates Others (2:04)

* The importance of knowing what drives different team members and departments

19:12 – Final Build: Leadership Advice Model (3:09)

* Louie’s four-part model for new leaders: shared understanding, clear priorities, removing bottlenecks, and enabling focus

22:27 – Reflection on LEGO Building (1:15)

* Louie shares his experience using LEGO bricks to communicate leadership concepts

Key Quotes

On Leadership Philosophy: “The leader, whether it’s me or somebody else, should be below. Should be more, you know, the servant leadership. Should not be above. It should be supporting the entire team.”

On Navigating Challenges: “The path is always through not around and in order to do that you have to be optimistic you have to be supportive you have to embrace risk.”

On Learning from Difficulty: “It’s the challenge that’s going to make the fulfillment. It’s not going to be the easy path. Everyone can do that. And once you do it, take an easy path, what is there to look back on?”

On Generational Strengths: “The older generation, you need to harness the pain that they went through, harness their experience… And then the weight of the words of the younger generation in terms of energy, right? You want to tap into that energy.”

On Leadership Priorities: “You have to absorb the stuff coming down from above. Don’t react and let it through. Absorb it because nothing’s worse than talking to someone and changing their priority from yesterday or changing their focus from yesterday.”

On Mutual Learning: “Even as a leader, I always say I have 30 mentors and those 30 happen to report to me in the HR system.”

How to Find Louie

Connect with Louie Celiberti on LinkedIn where he’s happy to share perspectives and learn from others.

About Herding Squirrels

Herding Squirrels is your podcast about modern teams where we uncover the nuts and bolts of teams. Hosted by Brandon Wetzstein, each episode features leaders sharing their insights through both conversation and hands-on LEGO Serious Play methodology, creating unique perspectives on team dynamics, leadership challenges, and workplace collaboration.

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