This is the fifty-fourth session of Glasp Talk!
Glasp Talk delves into intimate interviews with luminaries from various fields, unraveling their genuine emotions, experiences, and the stories behind them.
Today’s guest is Gregor Ojstersek, a seasoned engineering leader and the Founder of the newsletter. In this conversation, Gregor explores what it means to be an engineer in the era of rapid AI advancement—not just building technology, but leading with thoughtfulness and intention.
From his early career experiences to growing his newsletter to over 150,000 subscribers and advising startups on how to build high-performing engineering organizations, Gregor shares rich insights grounded in experience.
Watch the full episode on YouTube
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Transcripts
Hi, everyone. Welcome back to another episode of Grasp Talk. Today, we are excited to have Gregor Oistasek with us. So Gregor is a seasoned engineer leader, an engineering leader, and the founder of the Engineering Leadership Newsletter, one of the fastest-growing newsletters for engineers and managers with over 150,000 subscribers. And he's currently a fractional CTO and… Read More
Highlights
The Evolving Role of Engineers:
Gregor challenges the traditional view of engineers as solely technical contributors. In the age of AI, he argues that engineers must not only write code but also lead with thoughtfulness and intention, communicate clearly, and think strategically.
The Cost of Convenience with AI:
As AI tools become more powerful, Gregor warns of a growing risk: losing the deep understanding that comes from grappling with complexity. True expertise, he notes, often emerges from the discomfort of solving difficult problems, rather than skipping them.
Why Startups Need Scrappy Builders:
In advising startups, Gregor emphasizes the value of "scrappy builders", individuals who thrive in ambiguity, adapt quickly, and solve problems resourcefully, stating they are more crucial for forming early-stage teams than candidates with polished resumes but little grit.
Key questions & insights
Q: What does it mean to be an engineer in the age of AI?
Gregor argues that being a great engineer today is not just about writing efficient code—it's about thinking long-term, communicating clearly, and leading with intentionality. Engineers must evolve into thoughtful leaders who understand both technology and people.
Q: What are the dangers of relying too heavily on AI tools?
While AI tools boost productivity, Gregor cautions that they can erode deep understanding if used uncritically. Mastery comes from wrestling with hard problems, not from bypassing them with automation.
Q: What should startups look for when hiring their first engineers?
Gregor emphasizes hiring “scrappy builders” over polished résumés. Early-stage startups need adaptable problem-solvers who thrive in ambiguity, not just pedigree or experience.
Q: What is the ideal role of a CTO in a startup?
The CTO should be a hands-on enabler who sets technical direction while remaining close to the ground. Gregor suggests that successful CTOs are not just technologists but also communicators and culture-builders.
Q: How can engineers grow into leadership roles?
Leadership in engineering, Gregor says, is built through self-awareness, effective communication, and the courage to step outside of one's technical comfort zone. Growth begins with embracing discomfort and thinking beyond code.
Course on Maven: “Senior Engineer to Lead: Grow and thrive in the role”
Learn skills and competencies to grow beyond Senior Engineer and thrive in a lead role (Team Lead, Tech Lead (Staff), Engineering Manager).
Growing from senior engineer to a lead role requires a mindset shift. You become a multiplier for the team, and helping others around you becomes one of the main priorities. You are not judged by your contribution anymore. The overall success of the team and projects is what becomes important.
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