Azure & DevOps Podcast

Jim Leonardo: Leading Software Teams - Episode 300

Jun 3, 2024

Jim Leonardo, Head of information technology at biBerk Insurance, discusses leadership in software development. Topics include the shortage of software leaders, career progression, T-shaped development, importance of testing, understanding customers, the Innovator’s Dilemma, learning from diverse experiences, and the value of minimum viable products (MVPs) in software development.

37:00

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Episode guests

Jim Leonardo

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Quick takeaways

Embrace T- or V-shaped development for efficient team dynamics.

Prioritize understanding customer needs and continuous learning in product management.

Deep dives

Embracing Leadership Challenges and Development

Jim Leonardo shares his journey of transitioning into leadership roles, reflecting on the benefits of delaying full-time managerial positions early in his career to further develop technical skills. He emphasizes the importance of understanding various roles within a team and being open to learning from individuals with diverse levels of experience. Jim discusses the significance of maintaining humility and continuous learning, highlighting the value of embracing different perspectives and skill sets to enhance personal and professional growth.

Prioritizing Testing in Software Development

01:20

Intro

2min

Transitioning from Developer to Software Leader

13min

Understanding Customers, Products, and Buyers in the Business World

5min

The Evolution of a List of Rules for Software Development

2min

Navigating the World of Content Creation, Programming Languages, and Microservices

13min

Exploring the Value of Sales Skills and Mentoring in Professional Success

2min

Jim has been building solutions for clients in the cloud on Microsoft Azure since 2012 and building solutions in general for 20 years or more. Now, he heads up information technology for biBerk Insurance, overseeing both software development and IT operations. Most of Jim’s experience is in consulting or enterprise with a few forays into product development.

Following the path of least resistance, Jim ended up working primarily with Microsoft tools. The tool you know is the usually best tool to use, so the Microsoft path offers less and less resistance for Jim as time goes on.

On the side, Jim is working on jimsrules.com to share experience and shaky opinions about teamwork and leadership in software development.

Topics of Discussion:

[3:33] There is a shortage of software leaders out there.

[4:22] Jim’s career progression.

[5:26] Pulling back from leadership roles.

[6:54] Recognizing the need to be hands-on and fill vacuums in leadership roles.

[8:35] Embracing T- or V-shaped development.

[11:34] If it isn’t tested, it is broken.

[16:47] Know who your customer is and what your product is.

[18:10] The Innovator’s Dilemma and the importance of asking why things are the way they are.

[21:21] No matter how much experience you have, there is something you can learn from someone with less experience.

[23:29] What we can learn from teen YouTubers.

[24:25] The 10 specific rules; Rule 77 — Minimum Viable Products (MVP) are the start, not the end of a program.

[26:26] Rule #7 about microservices.

[27:52] Applying Conway’s Law.

[33:18] Rule 37 — Automated tests are my pillow.

Rule 59 — A leader’s job is to support the team. Most org charts are upside-down.

Rule 68 — No one is a zero. They either add to the team or take away from it. The question is whether those who are taking away are growing towards a positive contribution.

Rule 74 — Keeping standards high ultimately creates a better work environment.

Rule 75 — When you prepare to teach something, you usually learn more than your potential students.

Mentioned in this Episode:

Clear Measure Way

Architect Forum

Software Engineer Forum

Programming with Palermo — New Video Podcast! Email us at programming@palermo.net.

Clear Measure, Inc. (Sponsor)

.NET DevOps for Azure: A Developer’s Guide to DevOps Architecture the Right Way, by Jeffrey Palermo — Available on Amazon!

Jeffrey Palermo’s Twitter — Follow to stay informed about future events!

Jim Leonardo LinkedIn

Jim’s Rules