Show Notes
Coding Chats episode 48 - John Crickett and Gilad Naor explore the differences between working at startups and big tech companies, discussing the pros and cons of each environment. They delve into career growth, the importance of mentorship, and the balance between specialization and generalization in tech careers. The discussion also covers the management track versus individual contributor roles, the role of managers in creating positive change, and the significance of interview preparation. Additionally, they highlight the value of side projects and the necessity for managers to build empathy through understanding various roles within their organizations. The conversation concludes with advice on taking ownership of one's career and the importance of continuous personal development.
Chapters 00:00 Startups vs. Big Tech: A Comparative Overview 03:19 Navigating Career Growth in Tech 06:08 The Reality of Big Tech Work 09:06 Specialization vs. Generalization in Tech Careers 11:39 The Management Track: Leadership vs. Management 14:28 Creating Positive Change as a Manager 17:14 Interview Preparation for Managers 20:33 Choosing the Right Stories for Interviews 26:59 Navigating Conflict in Technical Leadership 29:12 Addressing Gaps in Management Experience 32:15 Interview Strategies for Senior Roles 35:17 Demonstrating Depth of Experience in Interviews 38:52 The Role of Side Projects in Personal Development 42:02 The Importance of Technical Empathy in Management 47:32 Taking Ownership of Your Career
Gilad's Links: Gilad's LinkedIn: https://www.linkedin.com/in/giladnaor Gilad's Website: https://managementdeltas.com/
John's Links: John's LinkedIn: https://www.linkedin.com/in/johncrickett/ John’s YouTube: https://www.youtube.com/@johncrickett John's Twitter: https://x.com/johncrickett John's Bluesky: https://bsky.app/profile/johncrickett.bsky.social
Check out John's software engineering related newsletters: Coding Challenges: https://codingchallenges.substack.com/ which shares real-world project ideas that you can use to level up your coding skills.
Developing Skills: https://read.developingskills.fyi/ covering everything from system design to soft skills, helping them progress their career from junior to staff+ or for those that want onto a management track.
Takeaways Working at startups allows for a broader range of experiences. Big tech offers more mentorship opportunities for career growth. The term 'startup' can encompass a wide range of company sizes and structures. Career growth in tech often requires navigating internal mobility. Specialization can provide a competitive advantage in tech careers. Management and leadership are distinct roles that require different skill sets. Interview preparation is crucial for both managers and individual contributors. Building empathy as a manager involves understanding various roles in the organization. Side projects can help maintain technical skills and foster personal development. Taking ownership of your career is essential for success.
More from Coding Chats
Coding Chats Episode 83 - In this episode, VB from OpenAI’s developer experience team explains why he thinks plan mode is obsolete and how coding agents have shifted from step-by-step instructions to outcome-driven, long-running work. We cover how to write a good agents.md, why tests still matter when agents write the code, spec-driven development, and why cloud agents may be the future of dev tooling.
Coding Chats Episode 82 - John talks with Dave Westgarth, head of delivery at a Databricks consultancy. Dave shares his path from a psychology degree and McDonald's into tech, and they discuss why the Scrum Master role is so misunderstood, how it differs from a delivery manager, and whether either needs to be technical.They also look at how AI is changing delivery work. Faster code just moves the bottleneck upstream, John argues there's no AI-specific skill you can't learn in a day, and engineering fundamentals are what make AI useful.
Coding Chats Episode 81 - Ben Howdle talks to John Crickett about being a first time CTO in a start-up. Ben, author of The First CTO, shares what changes when you move from building technology to leading a technical team: the pressure, the trade-offs, and the realization that writing code is only part of the job.Drawing on startup experience and lessons learned the hard way, Ben discusses how to balance quality against runway, manage people, and communicate technical decisions in terms that founders and other non-technical stakeholders can understand. He also explores why resourcefulness, resilience, and comfort with ambiguity matter so much—and why CTOs often spend more time selling ideas than they expect.Whether you’re stepping into your first CTO role or leading a technical team at an early-stage company, this conversation offers candid insights into the realities of technical leadership.
Coding Chats Episode 80 - start-up advisor Alexander Berkovich shares his expertise on building successful start-ups, hiring strategies, CTO roles, and the importance of communication between technical and business teams. Discover practical tips for navigating the challenges of early-stage companies and how to align technical excellence with business goals.
Coding Chats Episode 79 - Richmond Alake, Director of AI Developer Experience at Oracle, joins John to discuss agent memory — how AI agents store, retrieve, and adapt to information. He argues that developers building memory on flat files are naively reinventing the database, and that once you factor in concurrency, security, and scalability, a proper database is inevitable. The conversation covers the full memory stack and how Oracle's AI database keeps embeddings and data together without shipping sensitive information to external providers.