20 Questions

Questions to Ask Director of Engineering

Strategic questions for engineering leaders that reveal technical vision, management philosophy, and insights into building high-performing engineering teams.

1

What's your vision for the engineering organization over the next 2-3 years?

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Why this works

Reveals their strategic thinking and long-term planning approach, showing how they align engineering with business goals.

2

How do you balance technical debt with feature development?

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Why this works

Shows their approach to technical decision-making and reveals their philosophy on code quality vs. delivery speed.

3

What's your approach to building and scaling engineering teams?

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Why this works

Reveals their management philosophy and strategies for team growth, which is crucial for understanding their leadership style.

4

How do you measure engineering productivity and success?

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Why this works

Shows their metrics-driven approach and reveals what they value most in engineering performance.

5

What's the biggest technical challenge your team is currently facing?

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Why this works

Gets current information about their technical landscape and reveals their problem-solving approach.

6

How do you approach technology stack decisions?

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Why this works

Reveals their decision-making process for technical choices and shows how they balance innovation with stability.

7

What's your philosophy on code reviews and quality assurance?

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Why this works

Shows their approach to maintaining code quality and reveals their standards for engineering excellence.

8

How do you handle technical disagreements within your team?

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Why this works

Reveals their conflict resolution skills and approach to managing different technical opinions.

9

What's your approach to mentoring and developing junior engineers?

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Why this works

Shows their investment in team growth and reveals their philosophy on knowledge transfer and career development.

10

How do you stay current with emerging technologies and industry trends?

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Why this works

Reveals their learning approach and shows how they balance staying current with practical application.

11

What's your experience with distributed systems and microservices?

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Why this works

Tests their technical depth in modern architecture patterns that are crucial for scalable systems.

12

How do you approach incident response and system reliability?

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Why this works

Shows their operational mindset and reveals their approach to maintaining system stability.

13

What's your philosophy on documentation and knowledge sharing?

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Why this works

Reveals their approach to maintaining institutional knowledge and shows how they value communication.

14

How do you handle competing priorities between different product teams?

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Why this works

Shows their project management skills and reveals how they balance stakeholder needs with technical constraints.

15

What's your approach to security in the development process?

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Why this works

Reveals their security mindset and shows how they integrate security considerations into development workflows.

16

How do you approach technical interviews and hiring decisions?

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Why this works

Shows their hiring philosophy and reveals what qualities they value most in engineering candidates.

17

What's your experience with agile methodologies and how do you adapt them?

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Why this works

Reveals their project management approach and shows how they balance process with flexibility.

18

How do you approach performance optimization and system scaling?

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Why this works

Shows their technical depth in system performance and reveals their approach to scalability challenges.

19

What's your philosophy on open source contributions and community engagement?

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Why this works

Reveals their approach to external engagement and shows how they value community involvement.

20

How do you balance innovation with maintaining existing systems?

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Why this works

Shows their approach to technical evolution and reveals how they balance new development with system maintenance.

Best Practices for Engaging Engineering Directors

Expert tips and techniques for getting the most out of these questions.

Best Practices

Focus on Strategic Thinking

Engineering directors think at a high level about systems, teams, and business impact. Ask questions that reveal their strategic approach to technical challenges.

Understand Their Technical Depth

Ask questions that test their understanding of modern engineering practices, architecture patterns, and scalability challenges.

Explore Their Leadership Philosophy

Understand how they approach team building, mentoring, and creating engineering culture. This reveals their management style and values.

Question Sequences

The Strategic Vision Sequence

1
What's your vision for the engineering organization over the next 2-3 years?
2
How do you balance technical debt with feature development?
3
What's the biggest technical challenge your team is currently facing?
4
How do you approach technology stack decisions?

The Team Building Sequence

1
What's your approach to building and scaling engineering teams?
2
How do you approach mentoring and developing junior engineers?
3
How do you handle technical disagreements within your team?
4
What's your philosophy on code reviews and quality assurance?

Common Pitfalls

Don't Ask About Specific Technologies Only

Focus on their approach to technology decisions rather than just their experience with particular tools or languages.

Avoid Overly Technical Implementation Details

At the director level, focus on strategy, architecture, and team management rather than specific coding implementations.

Don't Ignore Business Context

Engineering directors must balance technical excellence with business needs. Ask questions that reveal this balance.

Conversation Templates

The Strategic Explorer

1
Step 1: Start with: "What's your vision for the engineering organization over the next 2-3 years?"
2
Step 2: Follow with: "How do you balance technical debt with feature development?"
3
Step 3: Deepen with: "What's the biggest technical challenge your team is currently facing?"

The Leadership Assessor

1
Step 1: Begin with: "What's your approach to building and scaling engineering teams?"
2
Step 2: Explore with: "How do you approach mentoring and developing junior engineers?"
3
Step 3: Conclude with: "How do you handle technical disagreements within your team?"

Further Reading

"The Manager's Path" by Camille Fournier
"Team Topologies" by Matthew Skelton and Manuel Pais
"Accelerate" by Nicole Forsgren, Jez Humble, and Gene Kim

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