The key responsibilities of a VP Engineering are:

• Development, delivery, and ongoing improvement of the product
• Collaborate with the Product leader and CTO to define and execute against the technical vision of the company
• Hire, lead, organize, and motivate the engineering team to accomplish objectives
• Foster a world-class engineering culture and equip team with resources to succeed
• Contribute to strategic business planning and communicate capabilities and trade-offs

Hiring

How do you create a strong pipeline of candidates and maximize close rates?

• Ownership of the hiring pipeline from end to end, especially closing the candidate
• Good communication skills 
• Some articulation of the specific techniques used to close candidates (e.g. team lunches, building empathy, connection with candidate etc.)
• Have engineers followed them from company to company?

How do you think about your time allocation? 

• A substantial amount of time spent on hiring and managing

Management and Leadership

Can they manage across geographies? Have you done so in the past?

• If this is or will be applicable for your role, ask for examples of managing different teams. Candid description of challenges and what they learned from them.
• How do they ensure remote teams have ability and support to be successful?

How do they communicate something to a team that you disagree with?

•  Authenticity. Explanation of why this is important. Not undermining higher ups with employees, but challenging those higher up directly
• Should be able to understand and explain the rationale for a decision they don’t fully agree with or isn’t ideal for their team

Can they give you an example of a time they had a difficult conversation/issue with an employee and how they handled it?

• Clear communication and concrete milestones. 
• Holding the person accountable for meeting those milestones and making the hard call in the case the employee doesn’t succeed.

How do they motivate a team? What have been their most successful strategies for retaining engineers and fostering a strong engineering culture?

• Looking for empathy
• Creating an environment where it’s safe to fail, and engineers feel supported, cared about, and like management is invested in their growth
• Articulating why their company’s technical problems are unique and rewarding to solve

How do they manage up, and how does it compare to how they manage down?

•  Looking for a balance between the two. Responsibility for the team they manage, but not friends. Understand the same relationship for their managers.

How have they mentored people in the past? How many mentees do they take on it one time? What do they look for in their mentees?

• 1-2 people at a time. It’s quite a bit of work. Some form of leading that person to water, helping them through the journey and motivating them along the way. Giving them challenges that are just out of their reach to motivate them. Introducing them to others who can help them.

Technology

What was the state of the product and technology at their last company when they joined? How did they prioritize assessing their challenges?

• Should be fairly in the weeds. Assessing frameworks, languages, tools, and other technology and why they made changes to those things.
• Assess culture and how it impacted business/product challenges

What are the main technical challenges facing this company as they see them? How do they think the business should respond to those today?

• Some sense of technical acumen. An impression that engineers who work for this person will be impressed by that technical skill. A logical argument for how the business should proceed especially when it comes to scaling

How do they avoid accruing technical debt in a business that’s scaling rapidly and prioritizing revenue generation?

• Concrete examples of pushing back against other company priorities
• Implementing infrastructure or frameworks early on that allowed them to scale cleanly

How do they stay involved with technology? Do they still write code or do code reviews? How involved are they with architecture of their company’s products?

• Will vary in importance, but always a plus
• How hands-on they are should match the needs of your company, if they’re too hands-off they may not garner respect from strong engineers, if they’re too hands-on with a large team they might be a better engineer than a manager.

How involved are they with customers and how does that affect product roadmap?

• Weighting of this question depends on how involved they need to be with selling and customer success
• Concrete examples of roadmap influenced by customer interaction

Management Team Success

What are the keys to success in working with the management team at this company?

• Building relationships with each of the key executives, especially the ones that they’re working with frequently
• Communicating clear expectations for what the engineering team can and cannot do. Providing clear trade-offs between different alternatives
• Standing firm on things that don’t make sense for their team but working to collaborate whenever possible

Product Management

How do they work with the Product org, and the leaders of that function? What is the role of the engineering team and the product management team (and those leaders) in the relationship they envision?

QA

Have they managed QA in the past?

What is their QA philosophy? Devops or separate team

‍