What CTOs and Software Engineers Should Ask During the Interview Process

A Nod to Kevin Goldsmith's "IT Depends 📚" Book

These questions are inspired by the incredible insights shared in Kevin Goldsmith's book IT Depends: Writing on Technology and Leadership (2012–2022). It’s a must-read for CTOs and Software Engineers looking to elevate their understanding of leadership, team dynamics, and building resilient engineering cultures.

For those eager to explore more, grab your copy here: 👉 IT Depends on Amazon

This book is packed with practical advice that every tech leader and engineer can apply today. A total game-changer for anyone looking to navigate the ever-evolving tech landscape! 🚀

High-level view

The interview process isn’t just about answering questions – it’s your chance to ask the right ones. Whether you’re a CTO building a high-performance software team or a software engineer evaluating a new opportunity, knowing what to ask during the interview ensures a strong fit between you, the role, and the company.

At TeamSation, we align top nearshore IT talent with business objectives by going beyond resumes and focusing on values, culture, and long-term goals. We started asking our CTO partners these questions when building software teams. But the question is: How do you identify these factors during an interview?

Here’s our guide, which coincides with Kevin Goldsmith's incredible insights on the must-ask questions for CTOs and software engineers.

Questions for CTOs to Ask During the Interview

1. Company Values and Mission

As a CTO, understanding how the company’s values align with your leadership style is essential.

• “What are the company’s core values, and how are they reflected in the team’s work?”
• “How does the leadership team support innovation and continuous learning?”

2. Tech Stack and Challenges

Evaluating the tech stack and upcoming challenges will help you gauge whether the team can support your goals for scalability and technical excellence.

• “What technologies are we using, and how often do we review or modernize our stack?”
• “What are the biggest technical challenges currently facing the team?”

3. Team Growth and Development

Top-performing teams thrive when there’s a clear path for growth and development.

• “How do you measure team success and individual progress?”
• “What opportunities exist for team members to grow into leadership roles?”

4. Remote Work and Collaboration

If the team operates remotely or in hybrid mode, collaboration tools and processes matter.

• “What systems are in place to ensure smooth collaboration across remote teams?”
• “How does the company foster a culture of inclusivity and accountability for distributed teams?”

5. Autonomy and Decision-Making

You want to ensure you’ll have the ability to make decisions and steer the team effectively.

• “What level of autonomy does the engineering leadership possess regarding technical decisions?”
• "How is the approval process for introducing new tools or workflows structured?”

Questions for Software Engineers to Ask During the Interview

1. Team Culture and Collaboration

Team dynamics can make or break your experience. Dig deep to learn about team culture.

• "What approach does the team take to share knowledge, particularly in resolving technical issues?"
• "Can you describe the onboarding process and let me know how soon I can begin working on actual projects?”

2. Tech Stack and Technical Debt

Understanding the tech stack helps you assess whether it matches your skills and interests.

• “What is the current technology stack, and what led to the selection of these tools?"
• “How does the team address technical debt, and is there dedicated time for cleanup?”

3. Growth Opportunities

A strong role is one that enables growth, both technically and professionally.

• “What opportunities for career advancement exist, including mentorship, training, or conferences?”
• “How do you measure success in this role during the first 6 to 12 months?”

4. Work-Life Balance

Work-life balance often reveals how much the company values its employees.

• “How does the team manage work-life balance, particularly when facing critical deadlines?
• "Do you offer flexible work hours or remote work options?"

5. Current Development Process

Processes determine how you’ll contribute and collaborate daily.

• "Could you guide me through the development cycle, starting with ideation and ending with deployment?”
• "What is your approach to code reviews, testing, and CI/CD (continuous integration/continuous deployment)?"

Why These Questions Matter

For CTOs

You’re not just hiring individuals – you’re building high-performing software engineering teams that drive business success. The answers to these questions help identify whether a company or candidate will align with your leadership style, technical vision, and long-term strategy.

For Software Engineers

The interview process isn’t about impressing the employer but ensuring they impress you. You can decide if the company aligns with your values, skills, and aspirations by asking questions about the tech stack, culture, and career development.

How TeamStation AI Aligns Talent and Business Objectives

At TeamStation AI, we take these insights a step further by ensuring that top Latin American developers and engineers are aligned with your business needs. We focus on:

• Culture Matching: Going beyond technical skills to ensure candidates align with team dynamics.
• Pre-Vetted Talent: Top-tier nearshore software engineers are pre-vetted for both technical and cultural fit.
• Growth-Focused Teams: Engineers ready to solve critical challenges and evolve with your team.

Through our AI-powered platform, we’ve built teams for global leaders like Parsable and Xivic, proving that aligning talent to priorities leads to long-term success.

Final Thoughts

Whether you’re a CTO hiring a new team or a software engineer stepping into a new role, the interview process should always be a two-way street. Asking the right questions ensures clarity, alignment, and a future-proof fit for both parties.

Ready to build the best software engineering teams in Latin America? With TeamStation AI, you can access pre-vetted, growth-focused talent that aligns with your business objectives and engineering challenges.

Want to explore how TeamStation AI can build your next tech dream team? Learn More Today 🚀

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