Essential Work Samples for Evaluating VP of Product Strategy Candidates

The Vice President of Product Strategy role is pivotal to any organization's success in today's competitive marketplace. This executive position requires a unique blend of strategic vision, analytical prowess, leadership capabilities, and cross-functional collaboration skills. When hiring for this critical role, traditional interviews alone often fail to reveal whether candidates can truly execute on the complex responsibilities they'll face.

Work samples and role plays provide a window into how candidates approach real-world challenges they'll encounter as VP of Product Strategy. These practical exercises reveal a candidate's ability to analyze market opportunities, develop compelling product strategies, communicate effectively with stakeholders, and lead product teams. Unlike hypothetical questions, these activities demonstrate how candidates actually perform under conditions similar to those they'll experience on the job.

For companies seeking to fill this strategic leadership position, implementing targeted work samples can dramatically reduce the risk of a poor hiring decision. The right VP of Product Strategy can accelerate growth and innovation, while the wrong hire can lead to misaligned product offerings, team dysfunction, and missed market opportunities—costly mistakes that can take quarters or years to correct.

The following four work samples are specifically designed to evaluate the essential competencies required for VP of Product Strategy success. Each exercise targets different aspects of the role, from strategic thinking and market analysis to leadership and cross-functional collaboration. By incorporating these activities into your interview process, you'll gain deeper insights into each candidate's capabilities and fit for your organization.

Activity #1: Market Opportunity Analysis and Product Strategy Development

This exercise evaluates a candidate's ability to analyze market data, identify opportunities, and develop a coherent product strategy. It tests strategic thinking, analytical skills, and the ability to translate market insights into actionable product direction—core responsibilities for any VP of Product Strategy.

Directions for the Company:

• Prepare a realistic but anonymized dataset about a market segment relevant to your industry, including market size, growth trends, competitive landscape, and customer pain points.
• Include some ambiguity and conflicting data points to test how candidates handle uncertainty.
• Provide the candidate with this information 24-48 hours before the interview.
• Allocate 20 minutes for presentation and 15 minutes for Q&A during the interview.
• Ensure executive stakeholders from product, engineering, and marketing are present to evaluate the candidate's ability to communicate with different functions.

Directions for the Candidate:

• Review the provided market data and identify 1-2 key opportunities for product development or enhancement.
• Develop a high-level product strategy that addresses these opportunities, including:
• Target customer segments
• Value proposition
• Competitive differentiation
• High-level product roadmap (6-12 months)
• Key success metrics
• Prepare a 15-20 minute presentation outlining your analysis and recommendations.
• Be prepared to explain your thought process and defend your strategic choices during Q&A.

Feedback Mechanism:

• After the presentation, provide specific feedback on one strength (e.g., "Your competitive analysis was particularly insightful") and one area for improvement (e.g., "The success metrics could be more specific and measurable").
• Ask the candidate to take 5 minutes to refine their proposed success metrics based on the feedback.
• Observe how receptive they are to feedback and how effectively they incorporate it into their thinking.

Activity #2: Cross-Functional Alignment Role Play

This role play assesses the candidate's ability to navigate cross-functional challenges and build alignment—critical skills for a VP of Product Strategy who must regularly collaborate with engineering, marketing, sales, and other departments.

Directions for the Company:

• Create a scenario where there's tension between departments about product priorities.
• Example scenario: Engineering wants to delay a product launch to improve technical architecture, while Sales is promising the feature to key customers by a specific date.
• Assign team members to play the roles of VP Engineering, VP Sales, and CEO.
• Brief the role players on their positions, concerns, and personalities.
• Provide the scenario to the candidate 30 minutes before the exercise.
• Allocate 25-30 minutes for the role play.

Directions for the Candidate:

• Review the scenario and prepare to facilitate a meeting between the VP Engineering, VP Sales, and yourself as the VP of Product Strategy.
• Your goal is to navigate the tension and develop a solution that addresses the core concerns of all parties.
• Consider both short-term needs and long-term strategic implications.
• Be prepared to:
• Facilitate the discussion
• Ask clarifying questions
• Propose potential solutions
• Build consensus around a path forward
• Document the agreed-upon next steps at the conclusion of the meeting.

Feedback Mechanism:

• After the role play, provide feedback on one strength (e.g., "You effectively acknowledged each stakeholder's concerns") and one area for improvement (e.g., "You could have more explicitly connected the discussion to our overall product strategy").
• Ask the candidate to spend 5 minutes reflecting on how they would approach the meeting differently based on the feedback.
• Have them share their reflections, noting their self-awareness and adaptability.

Activity #3: Product Roadmap Prioritization Exercise

This exercise evaluates a candidate's ability to make strategic trade-offs and prioritize initiatives—essential skills for a VP of Product Strategy who must balance competing demands with limited resources.

Directions for the Company:

• Create a list of 8-10 potential product initiatives with varying levels of:
• Revenue potential
• Strategic alignment
• Technical complexity
• Customer demand
• Competitive pressure
• Include a mix of short-term wins and long-term strategic bets.
• Provide basic information about company goals, available resources, and market context.
• Give the candidate this information 1 hour before the exercise.
• Allocate 45 minutes for the exercise (30 minutes for preparation, 15 minutes for presentation).

Directions for the Candidate:

• Review the list of potential product initiatives and the company context.
• Develop a prioritized roadmap for the next 12 months, allocating the limited resources available.
• Create a simple framework to explain your prioritization decisions.
• Be prepared to explain:
• Your prioritization methodology
• Why certain initiatives were prioritized over others
• How your roadmap aligns with company goals
• Key dependencies or risks in your plan
• How you would communicate this roadmap to different stakeholders
• Present your roadmap and rationale in 15 minutes.

Feedback Mechanism:

• After the presentation, provide specific feedback on one strength (e.g., "Your framework for evaluating strategic alignment was very clear") and one area for improvement (e.g., "The plan could better address how to manage stakeholder expectations for deprioritized items").
• Ask the candidate to take 5 minutes to develop a brief communication plan for a key stakeholder whose priority initiative was not included in the first 6 months of the roadmap.
• Evaluate their ability to handle difficult conversations and manage expectations.

Activity #4: Product Team Coaching Role Play

This role play assesses the candidate's leadership and mentoring abilities—crucial for a VP of Product Strategy who must develop and guide a team of product managers.

Directions for the Company:

• Create a scenario involving a product manager who is struggling with a specific challenge.
• Example scenarios:
• A product manager having difficulty translating customer feedback into clear requirements
• A product manager struggling to influence engineering without formal authority
• A product manager who is technically strong but having trouble communicating with non-technical stakeholders
• Provide background information on the product manager's experience, strengths, and areas for development.
• Have someone play the role of the product manager, briefing them thoroughly on how to respond.
• Give the candidate the scenario 30 minutes before the exercise.
• Allocate 25-30 minutes for the role play.

Directions for the Candidate:

• Review the information about the product manager and their current challenge.
• Prepare for a coaching conversation to help them improve their effectiveness.
• During the 25-minute conversation:
• Build rapport
• Ask questions to understand their perspective
• Provide constructive feedback
• Offer guidance and suggestions
• Develop a plan for improvement
• Set clear expectations and follow-up
• Your goal is to help the product manager grow while maintaining their motivation and confidence.

Feedback Mechanism:

• After the role play, provide feedback on one strength (e.g., "You asked excellent questions to understand the root cause of the issue") and one area for improvement (e.g., "You could have provided more specific examples to illustrate your points").
• Ask the candidate to take 5 minutes to reflect on how they would follow up with this product manager in 2 weeks.
• Have them share their follow-up plan, evaluating their approach to ongoing development and accountability.

Frequently Asked Questions

Q: How much time should we allocate for these work samples in our interview process?

A: Plan for approximately 2-3 hours total across multiple interview sessions. Activity #1 and #3 work well as standalone sessions, while Activities #2 and #4 can be combined if time is limited. Consider spreading these across different days to avoid candidate fatigue.

Q: Should we use all four of these work samples for every VP of Product Strategy candidate?

A: While using all four provides the most comprehensive assessment, you can select the 2-3 most relevant to your specific needs. At minimum, include one strategic exercise (Activity #1 or #3) and one leadership/collaboration exercise (Activity #2 or #4).

Q: How should we weigh performance on these work samples compared to traditional interviews?

A: Work samples should account for 50-60% of your evaluation, as they provide the most predictive insight into on-the-job performance. Traditional interviews remain valuable for assessing cultural fit and exploring past experiences.

Q: What if our company doesn't have team members who can effectively role play for Activities #2 and #4?

A: Consider bringing in external recruiters or consultants who can be briefed to play these roles. Alternatively, you can modify these exercises to be discussion-based, where candidates explain their approach to handling these scenarios.

Q: How much company-specific information should we include in these exercises?

A: Provide enough context for meaningful engagement without requiring deep company knowledge. For candidates advancing to final rounds, you can include more company-specific elements. Always ensure that sensitive information is anonymized or modified.

Q: How do we ensure consistency when evaluating different candidates?

A: Develop a structured scorecard for each activity based on the key competencies being assessed. Have the same interviewers evaluate all candidates on a given activity, and conduct a calibration session before beginning the interview process.

Finding the right VP of Product Strategy is a critical investment in your company's future. By incorporating these work samples into your interview process, you'll gain deeper insights into each candidate's capabilities and significantly increase your chances of making a successful hire. Remember that the best candidates will appreciate a rigorous process that demonstrates your commitment to excellence.

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