Essential Work Sample Exercises for Evaluating Chief of Staff Candidates

The Chief of Staff role is a critical position that serves as a strategic partner to executive leadership, particularly the CEO. This role requires a unique blend of strategic thinking, operational excellence, communication skills, and the ability to navigate complex organizational dynamics. Unlike many other positions, the Chief of Staff must excel at both high-level strategic planning and detailed execution, making traditional interview methods insufficient for thoroughly evaluating candidates.

Work samples and role plays provide invaluable insights into how candidates actually approach the multifaceted challenges of the Chief of Staff position. These practical exercises reveal a candidate's ability to prioritize competing demands, communicate effectively with various stakeholders, solve complex problems, and drive strategic initiatives forward—all essential competencies that can't be adequately assessed through conversation alone.

By implementing structured work samples, organizations can observe candidates' thought processes, decision-making frameworks, and execution capabilities in real-time. This approach significantly reduces the risk of hiring someone who interviews well but may struggle with the practical demands of the role. Additionally, these exercises give candidates a realistic preview of the position, helping ensure mutual fit.

The following four work sample exercises are specifically designed to evaluate the core competencies required for Chief of Staff success. Each activity simulates real challenges the candidate would face in the role, providing both the hiring team and the candidate with meaningful data points for evaluation. When implemented thoughtfully, these exercises will help identify candidates who can truly excel as a strategic partner to your executive leadership.

Activity #1: Strategic Initiative Prioritization Exercise

This exercise evaluates the candidate's ability to analyze competing priorities, make strategic recommendations, and communicate their rationale effectively—core skills for any Chief of Staff who must help executives focus organizational resources on the highest-impact initiatives.

Directions for the Company:

• Prepare a document outlining 6-8 potential strategic initiatives for the organization, including brief descriptions, estimated resource requirements, potential impact, and alignment with company goals.
• Include some initiatives that clearly align with the company's strategic priorities and others that may be valuable but less aligned.
• Allocate 45-60 minutes for this exercise.
• Provide the candidate with the company's mission statement, annual goals, and current resource constraints.
• Have a senior leader available to answer clarifying questions during a portion of the exercise.

Directions for the Candidate:

• Review the list of potential strategic initiatives and the company's strategic context.
• Develop a prioritized recommendation for which 2-3 initiatives should be pursued immediately, which should be scheduled for later implementation, and which should be deprioritized or eliminated.
• Create a one-page executive summary explaining your recommendations and rationale.
• Prepare a 10-minute presentation of your findings and recommendations to deliver to the interview panel.
• Be prepared to defend your prioritization decisions and discuss how you would communicate these priorities across the organization.

Feedback Mechanism:

• After the presentation, the interview panel should provide specific feedback on one aspect the candidate handled well (such as their analytical approach or communication clarity) and one area for improvement (such as considering additional stakeholders or implementation challenges).
• Give the candidate 5-10 minutes to revise their recommendation based on the feedback, focusing specifically on the improvement area identified.
• Observe how receptively and effectively the candidate incorporates the feedback.

Activity #2: Cross-Functional Meeting Facilitation Role Play

This exercise assesses the candidate's ability to facilitate productive discussions among stakeholders with different priorities and perspectives—a critical skill for a Chief of Staff who often needs to drive alignment across departments.

Directions for the Company:

• Create a scenario involving a cross-functional challenge that requires input and buy-in from multiple departments (e.g., a product launch delay, a new company-wide initiative, or a resource allocation decision).
• Assign 3-4 interviewers to play the roles of department heads with specific concerns, priorities, and personalities.
• Provide role players with character briefs that include their department's priorities, concerns, and potential points of resistance.
• Prepare a briefing document for the candidate that outlines the meeting's purpose, background on the issue, and desired outcomes.
• Allow 30 minutes for the role play meeting.

Directions for the Candidate:

• Review the briefing document 30 minutes before the exercise begins.
• Prepare an agenda and approach for facilitating the meeting effectively.
• During the role play, facilitate the discussion to achieve the stated objectives.
• Navigate conflicting priorities and perspectives to drive toward consensus or a clear path forward.
• Demonstrate active listening, effective questioning, and the ability to synthesize diverse viewpoints.
• Conclude the meeting with clear next steps and ownership assignments.

Feedback Mechanism:

• After the role play, provide feedback on the candidate's facilitation strengths and one specific area where their approach could be more effective.
• Give the candidate 5 minutes to explain how they would adjust their approach in a follow-up meeting based on this feedback.
• Assess their self-awareness and ability to adapt their facilitation style.

Activity #3: Executive Communication Exercise

This exercise evaluates the candidate's ability to distill complex information into clear, actionable communications—an essential skill for a Chief of Staff who often serves as the bridge between the executive team and the rest of the organization.

Directions for the Company:

• Compile a set of materials that might typically cross an executive's desk: departmental updates, financial reports, customer feedback, competitive intelligence, and internal operational metrics.
• Include some contradictory information and potential red flags that require attention.
• Provide context about upcoming executive decisions that need to be informed by this information.
• Allow 60 minutes for the exercise.

Directions for the Candidate:

• Review all provided materials and identify the most critical information, trends, and issues that require executive attention.
• Create three deliverables:

1. A concise executive summary (1 page maximum) highlighting key insights and recommendations
2. A more detailed briefing document organizing the information logically with supporting data
3. A draft email communication to the broader organization about one of the key issues, appropriate for the CEO to send

• Be prepared to explain your process for determining what information was most important and how you structured your communications for different audiences.

Feedback Mechanism:

• Provide feedback on the clarity, completeness, and strategic focus of the candidate's communications.
• Identify one aspect of their communication approach that could be improved (e.g., better data visualization, more actionable recommendations, or clearer messaging).
• Ask the candidate to revise one section of their work based on this feedback within 15 minutes.
• Evaluate their ability to quickly incorporate feedback and improve their communication.

Activity #4: Crisis Response Simulation

This exercise assesses the candidate's ability to handle unexpected challenges, make decisions under pressure, and coordinate an effective response—critical skills for a Chief of Staff who often needs to manage crises on behalf of the executive team.

Directions for the Company:

• Develop a realistic crisis scenario relevant to your industry (e.g., a major product issue, negative press coverage, unexpected leadership departure, or operational disruption).
• Create a series of evolving updates that will be provided to the candidate at timed intervals during the exercise.
• Prepare role players who can act as key stakeholders the candidate might need to consult (e.g., legal counsel, PR director, department heads).
• Allow 45-60 minutes for the full simulation.

Directions for the Candidate:

• You will be presented with an emerging crisis situation that requires immediate attention.
• As information becomes available, determine what actions need to be taken, who needs to be involved, and what communications are necessary.
• You may consult with available stakeholders (role played by interviewers) as needed.
• Develop a crisis response plan that includes:

1. Immediate actions to address the situation
2. Communication strategy for different stakeholders (employees, customers, board, etc.)
3. Process for ongoing monitoring and management of the situation

• Be prepared to adjust your approach as new information emerges during the simulation.

Feedback Mechanism:

• After the simulation, provide feedback on the candidate's crisis management approach, highlighting one strength and one area for improvement.
• Ask the candidate to reflect on what they would do differently if faced with a similar situation in the future, based on the feedback.
• Evaluate their ability to learn from the experience and adapt their approach.

Frequently Asked Questions

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

Each exercise requires 45-60 minutes to complete, plus time for feedback and discussion. We recommend selecting 1-2 exercises that best align with your organization's priorities for the Chief of Staff role, rather than attempting all four. The entire work sample portion should ideally not exceed 2-3 hours of the candidate's time.

Should these exercises be conducted in person or virtually?

These exercises can be effective in either format. For virtual assessments, ensure you have reliable technology for document sharing and collaboration. The meeting facilitation role play may be more effective in person but can be adapted for video conferencing with proper preparation.

How should we evaluate candidates across these different exercises?

Create a structured scorecard for each exercise that aligns with the key competencies for your Chief of Staff role. Have multiple interviewers evaluate the same dimensions independently before discussing their observations. Look for patterns across exercises rather than focusing too heavily on performance in any single activity.

What if our organization doesn't have the resources to create these detailed scenarios?

Start with simplified versions of these exercises. For example, the strategic prioritization exercise could use publicly available information about your industry rather than detailed internal initiatives. The key is to create scenarios that test the relevant skills, even if they're somewhat abstracted from your specific organizational context.

How do we ensure these exercises don't disadvantage candidates without prior Chief of Staff experience?

Focus evaluation on the underlying competencies rather than specific knowledge of Chief of Staff responsibilities. Provide clear context and expectations for each exercise. Remember that these exercises are designed to assess capabilities that may have been developed in various roles, not just previous Chief of Staff positions.

Should we share these exercises with candidates in advance?

For some exercises, like the strategic prioritization activity, providing the scenario 24 hours in advance can lead to more thoughtful responses. For others, like the crisis response simulation, the ability to think on one's feet is part of what's being evaluated. Consider which approach best tests the skills most critical for your specific role.

The Chief of Staff role requires a unique combination of strategic thinking, operational excellence, and interpersonal savvy. By incorporating these work samples into your hiring process, you'll gain invaluable insights into how candidates actually approach the complex challenges of the position. This approach not only helps identify the most qualified candidates but also gives applicants a realistic preview of the role, leading to better hiring decisions and stronger organizational outcomes.

For more resources to improve your hiring process, check out Yardstick's AI Job Descriptions, AI Interview Question Generator, and AI Interview Guide Generator. You can also find our Chief of Staff job description at https://yardstick.team/job-description/chief-of-staff.

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