IT MATTERS Podcast

Oct 9, 2026

Ep. 42- Why Curiosity Still Matters in IT Leadership, with Neil Stein

This episode of the IT Matters Podcast features a conversation between host Keith Hawkey and guest Neil Stein, seasoned IT leader and Senior Vice President of Technology Services at OrthoCarolina. Neil shares insights on the evolution of technology, problem-solving skills, and the importance of curiosity in IT. Together, they explore how a solid foundation of knowledge, paired with the habit of asking the right questions, can shape the next generation of tech leaders.

Conversation Highlights:

0:00 Introducing Neil Stein and his IT journey

[5:39] From chemistry to a career in technology

[12:43] GUIs and the art of troubleshooting

[16:28] Advice for new IT professionals

[20:44] Why the best leaders keep asking questions

[29:04] Connect with Neil

Notable Quotes:

"Talk to your peers. Question things. Be curious. Those are the fundamental pieces as you're a leader." - Neil Stein [18:20]

"From day one, as soon as you graduate high school, be the person asking the questions and never stop." - Neil Stein [21:28]

Connect with Neil Stein on LinkedIn.

Read the transcript: Episode 42

The IT Matters Podcast is about IT matters and matters pertaining to IT. It is produced by Opkalla, a technology advisory firm that helps their clients navigate the confusion in the technology marketplace and choose the solution that is right for their business.

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