Essential Work Sample Exercises for Hiring a Vice President of Engineering

The Vice President of Engineering role is pivotal to any technology organization's success. This leader sits at the intersection of technical excellence, strategic vision, and people leadership. Finding the right person requires more than just reviewing resumes and conducting standard interviews – it demands seeing candidates in action through carefully designed work samples.

Work samples provide invaluable insights into how candidates approach real-world challenges they'll face in the role. For a VP of Engineering position, these exercises should evaluate technical judgment, leadership capabilities, strategic thinking, and communication skills. Unlike hypothetical questions, work samples reveal how candidates actually perform tasks central to the role.

The exercises outlined below are designed to simulate key responsibilities of a VP of Engineering. They assess a candidate's ability to develop technical strategy, lead engineering teams, make architectural decisions, and collaborate across departments. By observing candidates complete these exercises, hiring teams can make more informed decisions based on demonstrated capabilities rather than self-reported skills.

Implementing these work samples will significantly improve your hiring process by providing objective data points for comparison across candidates. They also give candidates a realistic preview of the role, helping ensure alignment between their expectations and the actual position. When executed properly, these exercises create a fair, consistent evaluation framework that leads to better hiring outcomes.

Activity #1: Technical Strategy and Roadmap Development

This exercise evaluates the candidate's ability to develop a coherent technical vision and translate it into an actionable roadmap. A successful VP of Engineering must balance technical debt, innovation, and business objectives while creating a strategic plan that engineering teams can execute.

Directions for the Company:

• Provide the candidate with a brief overview of your current technical stack, key challenges, and business objectives for the next 12-18 months.
• Include information about team structure, size, and any significant technical debt or architectural issues.
• Give the candidate 2-3 days to prepare a technical strategy presentation.
• Allocate 30 minutes for presentation and 30 minutes for Q&A with key stakeholders.
• Ensure the leadership team attending has representatives from Product, Design, and Business units to simulate cross-functional collaboration.

Directions for the Candidate:

• Develop a 12-18 month technical roadmap that addresses the company's challenges and aligns with business objectives.
• Include key initiatives, resource allocation recommendations, and technical debt management strategies.
• Outline architectural evolution plans and technology adoption recommendations.
• Prepare a 20-30 minute presentation with supporting slides.
• Be prepared to discuss trade-offs, prioritization decisions, and implementation approaches during Q&A.

Feedback Mechanism:

• After the presentation, provide specific feedback on one strategic element the candidate handled exceptionally well.
• Offer one area where the strategy could be improved or a critical consideration that was overlooked.
• Allow the candidate 10-15 minutes to respond to the improvement feedback and adjust their approach, demonstrating adaptability and receptiveness to input.

Activity #2: Engineering Team Leadership Scenario

This exercise assesses the candidate's leadership approach, people management philosophy, and ability to handle complex team dynamics. A VP of Engineering must excel at building high-performing teams, addressing performance issues, and creating a positive engineering culture.

Directions for the Company:

• Create a detailed scenario describing a challenging team situation, such as:
• A high-performing team experiencing burnout and decreased velocity
• Integration of two engineering teams with different cultures following an acquisition
• A critical project falling behind schedule with team conflicts
• Performance issues with a senior engineer who has critical domain knowledge
• Provide context about team composition, history, and relevant organizational factors.
• Schedule a 45-minute role-play session where an interviewer plays the role of a direct report.

Directions for the Candidate:

• Review the scenario and prepare an approach to address the situation.
• During the role-play, demonstrate your leadership style and problem-solving approach.
• Be prepared to discuss your thought process, including how you'd gather information, develop action plans, and communicate with stakeholders.
• Focus on both immediate actions and longer-term strategies to prevent similar issues.
• Consider team morale, productivity, and alignment with company values in your approach.

Feedback Mechanism:

• Provide feedback on the candidate's strongest leadership quality demonstrated during the exercise.
• Suggest one area where their approach could be enhanced or a perspective they might have overlooked.
• Ask the candidate to outline how they would incorporate this feedback into their leadership approach, allowing them to demonstrate adaptability and self-awareness.

Activity #3: Technical Architecture Review

This exercise evaluates the candidate's technical depth, architectural thinking, and ability to make sound technical decisions. While a VP of Engineering may not code daily, they must possess sufficient technical expertise to guide architectural decisions and evaluate technical approaches.

Directions for the Company:

• Prepare documentation for a significant architectural challenge your organization is facing or a recent architectural decision you've made.
• Include system diagrams, technical constraints, business requirements, and scalability considerations.
• Provide context about existing systems and technical debt that influences the decision.
• Schedule a 60-minute session with key technical leaders from your organization.
• Consider including a deliberate flaw or suboptimal approach in the architecture to test the candidate's critical thinking.

Directions for the Candidate:

• Review the architectural documentation prior to the session.
• Prepare to lead a technical discussion evaluating the architecture's strengths and weaknesses.
• Identify potential risks, scalability concerns, and alternative approaches.
• Be prepared to discuss trade-offs between different architectural options.
• Consider both technical excellence and practical implementation constraints.
• Demonstrate how you would guide a team through making this architectural decision.

Feedback Mechanism:

• Highlight one particularly insightful observation or recommendation the candidate made during the review.
• Identify one area where their technical analysis could be strengthened or a consideration they missed.
• Ask the candidate to elaborate on how they would address this gap in their analysis, allowing them to demonstrate technical adaptability and depth.

Activity #4: Cross-Functional Collaboration Exercise

This exercise assesses the candidate's ability to collaborate effectively with non-engineering stakeholders, balance competing priorities, and communicate technical concepts to non-technical audiences. A successful VP of Engineering must excel at bridging the gap between technical and business considerations.

Directions for the Company:

• Create a scenario involving tension between engineering constraints and business objectives, such as:
• A major feature request with unrealistic timeline expectations from key clients
• Technical debt remediation competing with new product development
• Security/compliance requirements impacting product launch timelines
• Resource allocation decisions between multiple high-priority initiatives
• Assemble a panel of 3-4 stakeholders from Product, Sales, Customer Success, and Executive leadership.
• Each stakeholder should have clear objectives and concerns relevant to their role.

Directions for the Candidate:

• Review the scenario and prepare to facilitate a 45-minute discussion with the cross-functional stakeholders.
• Your goal is to build consensus around a path forward that balances technical and business considerations.
• Demonstrate how you communicate technical constraints and trade-offs to non-technical audiences.
• Show how you advocate for engineering needs while remaining sensitive to business priorities.
• Prepare to handle pushback and navigate competing interests.
• Conclude with a clear action plan that addresses key stakeholder concerns.

Feedback Mechanism:

• Provide feedback on the candidate's most effective collaboration or communication strategy demonstrated.
• Suggest one way they could have more effectively built consensus or addressed a particular stakeholder's concerns.
• Allow the candidate 5-10 minutes to reflect on how they would incorporate this feedback in a similar future scenario.

Frequently Asked Questions

How long should we allocate for these work sample exercises?

Each exercise requires different time commitments. The Technical Strategy exercise needs 2-3 days of preparation time plus a 1-hour session. The Team Leadership and Cross-Functional exercises require about 30-45 minutes of preparation and 45-60 minutes to conduct. The Architecture Review requires 1-2 hours of preparation and a 60-minute session. We recommend spreading these across the interview process rather than conducting them all in one day.

Should we use real company challenges or create fictional scenarios?

Using real challenges provides the most authentic assessment and gives candidates insight into actual problems they'll face. However, ensure you're not sharing highly sensitive information. For earlier interview stages, you might use anonymized or simplified versions of real challenges. For final candidates, using actual current challenges can be valuable as their input might be immediately useful.

How should we evaluate candidates across these exercises?

Create a structured scorecard for each exercise that maps to the key competencies for a VP of Engineering. Include both technical and leadership dimensions. Have multiple observers score independently before discussing. Look for patterns across exercises – strong candidates should demonstrate consistent capabilities across different scenarios.

What if our company doesn't have the resources to conduct all four exercises?

If resources are limited, prioritize the Technical Strategy and Team Leadership exercises, as these assess the most critical aspects of the VP of Engineering role. You can also scale down the exercises – for example, making the architecture review more focused or combining elements of multiple exercises into a comprehensive case study.

How do we ensure these exercises don't disadvantage candidates from different backgrounds?

Provide clear instructions and equal preparation time to all candidates. Be conscious of potential biases in how you evaluate responses. Focus on the effectiveness of the approach rather than whether it matches your company's current methods. Consider having a diverse panel of evaluators to bring multiple perspectives to the assessment.

Should we compensate candidates for the time spent on these exercises?

For exercises requiring substantial preparation time (particularly the Technical Strategy exercise), consider offering compensation, especially for candidates who reach the final stages. This demonstrates respect for their time and expertise while ensuring candidates who may not have extensive free time aren't disadvantaged.

The VP of Engineering role is one of the most critical hires your company will make. By implementing these work samples, you'll gain deeper insights into candidates' capabilities than traditional interviews alone can provide. This comprehensive approach helps ensure you select a leader who can drive technical excellence, build strong teams, and align engineering efforts with business objectives.

For more resources on building effective hiring processes, check out Yardstick's AI Job Descriptions, AI Interview Question Generator, and AI Interview Guide Generator. You can also find the complete job description for this role at VP of Engineering Job Description.

Ready to build a complete interview guide for this role? Sign up for a free Yardstick account