Interview Guide for

Chief of Staff

This comprehensive guide outlines a structured interview process for the Chief of Staff position, a critical executive partner role that requires exceptional leadership, communication, and strategic capabilities. By following this methodical approach, you'll be able to identify candidates who can effectively drive strategic initiatives, manage operations, and serve as a trusted advisor to your executive leadership.

How to Use This Guide

This interview guide provides a framework for consistently evaluating Chief of Staff candidates while allowing for personalization to your organization's specific needs:

Customize for Your Context - Adapt questions and assessments to align with your company's specific industry, culture, and the executive whom the Chief of Staff will support.
Prepare Your Interview Team - Share this guide with everyone involved in the hiring process to ensure alignment on evaluation criteria and interview approach.
Follow the Sequence - The structured progression of interviews helps systematically evaluate different aspects of the candidate's capabilities.
Use Follow-up Questions - Dig deeper into candidates' initial responses to gain comprehensive understanding of their experiences and thought processes.
Score Independently - Each interviewer should complete their scorecard before discussing the candidate with others to prevent bias.

For additional guidance on making your interviews more effective, check out our resources on how to conduct a job interview and why structured interviews matter.

Job Description

Chief of Staff

About [Company]

[Company] is a [Industry] company located in [Location] dedicated to [Company Mission/Values]. We are a rapidly growing organization committed to [Company Goals] and building a dynamic and impactful team.

The Role

As Chief of Staff, you will partner directly with our [Executive Title] to drive strategic initiatives, manage day-to-day operations, and ensure the effective execution of our company's vision. This pivotal role serves as the right hand to our [Executive Title], helping to amplify their effectiveness while managing critical projects and communications. You'll be at the center of our organization's most important work, connecting strategy with execution.

Key Responsibilities

Drive strategic planning and execution alongside the [Executive Title]
Manage complex projects and oversee operational priorities
Serve as a key communicator and liaison between the [Executive Title] and stakeholders
Prepare high-impact presentations, reports, and communications
Identify and implement process improvements for organizational effectiveness
Manage the [Executive Title]'s time, priorities, and communications effectively
Provide leadership support across teams and departments
Anticipate challenges and develop proactive solutions

What We're Looking For

Exceptional strategic thinking and analytical capabilities
Outstanding communication and interpersonal skills
Strong project management experience and organizational abilities
Proven track record of leadership and influencing stakeholders at all levels
Ability to handle sensitive and confidential information with discretion
Experience working directly with executive leadership
Adaptability and comfort with ambiguity in a fast-paced environment
Proactive problem-solving mindset with attention to detail
Experience in [Industry] preferred but not required

Why Join [Company]

At [Company], we're not just building a product/service – we're reshaping [Industry]. By joining our team, you'll have the opportunity to make a significant impact in a high-visibility role that touches all aspects of our business.

Competitive compensation package: $[Salary Range]
Comprehensive benefits including [Benefits]
Opportunity to work directly with top leadership
Professional development and growth opportunities
[Additional perks and benefits]

Hiring Process

We've designed our interview process to be thorough yet efficient, enabling us to make quick decisions while ensuring the right fit for this critical role. Here's what you can expect:

Initial Screening - A conversation with our recruiting team to discuss your background and interest in the role
Leadership Assessment - A practical exercise that simulates key aspects of the Chief of Staff role
Career Journey Interview - An in-depth discussion about your professional experience and accomplishments
Strategic Leadership Interview - Focused conversation about your approach to strategy, execution, and leadership
Stakeholder Management Interview - Assessment of your communication and relationship-building capabilities
Executive Team Meeting - Opportunity to meet with key leaders you'd be working with (for finalists)
Final Conversation - Meeting with board members or additional stakeholders (for finalists)

Ideal Candidate Profile (Internal)

Role Overview

The Chief of Staff serves as a strategic partner and force multiplier for the [Executive Title], driving key initiatives, managing complex projects, and facilitating effective communication across the organization. This role requires someone who can think strategically while executing tactically, navigate ambiguity with confidence, and build strong relationships at all levels. The ideal candidate will seamlessly balance analytical thinking with exceptional people skills to advance the executive's agenda and organizational priorities.

Essential Behavioral Competencies

Strategic Thinking - Ability to see the big picture, identify patterns, and connect dots across various business functions. Adept at balancing short-term needs with long-term vision and translating strategy into actionable plans.

Execution Excellence - Consistently delivers results through disciplined planning, resource allocation, and follow-through. Can manage multiple complex workstreams simultaneously while maintaining high quality standards.

Communication Mastery - Exceptional verbal and written communication skills with the ability to tailor messages to different audiences. Can distill complex information into clear, compelling narratives.

Relationship Building - Establishes trust and credibility quickly with diverse stakeholders. Navigates organizational politics effectively and builds collaborative partnerships across functions and levels.

Adaptability - Thrives in ambiguous situations and rapidly changing environments. Can pivot quickly, reprioritize work, and maintain effectiveness during uncertainty.

Desired Outcomes

Increase the [Executive Title]'s effectiveness by 30% through strategic time management, prioritization, and preparation
Successfully drive 3-5 cross-functional strategic initiatives to completion annually
Establish and maintain effective communication channels between the executive office and key stakeholders
Identify and implement at least 2-3 significant process improvements that enhance organizational effectiveness
Build trusted advisor relationships with the executive team and board members

Ideal Candidate Traits

7+ years of progressive leadership experience, ideally including direct work with executive leadership
Strategic mindset paired with strong operational capabilities and attention to detail
Political savvy with ability to navigate complex organizational dynamics
High EQ with exceptional listening and observation skills
Confidence to push back appropriately and provide candid feedback
Discretion when handling sensitive and confidential information
Comfort with ambiguity and ability to create structure in unstructured situations
Professional presence and executive maturity
Proactive problem-solver who anticipates issues before they arise
Ability to manage up effectively while building horizontal relationships

Screening Interview

Directions for the Interviewer

This initial screening interview aims to quickly assess candidate fit for the Chief of Staff role. Focus on evaluating the candidate's relevant leadership experience, strategic capabilities, and communication skills. This conversation should help determine if the candidate has the core qualifications and leadership presence needed to succeed in this role.

Pay particular attention to how candidates articulate their experience working with executive leadership, managing complex projects, and driving strategic initiatives. Their communication style during this interview often reflects how they would interact with stakeholders as Chief of Staff.

Allow 30-45 minutes for this interview, reserving 5-10 minutes at the end for candidate questions. Take notes on both the content of their responses and how they communicate.

Directions to Share with Candidate

This conversation will focus on understanding your background, experience, and approach to strategic leadership. I'll ask about your career journey, particularly your experience working with executive leadership and managing cross-functional initiatives. Feel free to ask clarifying questions, and we'll reserve time at the end for any questions you have about the role or company.

Interview Questions

Tell me about your current role and how it has prepared you for a Chief of Staff position.

Areas to Cover

Current responsibilities and scope of impact
Experience working directly with executive leadership
Strategic vs. operational balance in current work
Key achievements that demonstrate readiness for Chief of Staff role
How they've served as a multiplier for leadership effectiveness

Possible Follow-up Questions

What aspects of your current role do you find most relevant to this position?
How have you partnered with executives to enhance their effectiveness?
What strategic initiatives have you helped drive in your organization?
How do you balance strategic thinking with tactical execution?

Can you describe a complex, cross-functional project you've led and how you ensured its success?

Areas to Cover

Project scope, stakeholders, and complexity
Their specific role and approach to leadership
How they managed relationships across different departments
Challenges encountered and how they were overcome
Results achieved and lessons learned

Possible Follow-up Questions

How did you gain buy-in from different stakeholders?
What was the most challenging aspect of coordinating across functions?
How did you track progress and ensure accountability?
What would you do differently if you could lead this project again?

How do you approach managing confidential information and navigating sensitive situations?

Areas to Cover

Experience handling confidential material
Their philosophy on discretion and trust
Examples of managing sensitive situations effectively
How they balance transparency with confidentiality
Judgment in deciding what information to share and with whom

Possible Follow-up Questions

What guidelines do you follow when determining what information to share?
How have you built trust with executives regarding sensitive matters?
Can you share an example of a sensitive situation you navigated successfully?
How do you manage relationships when you have information others don't?

Tell me about a time when you had to influence decision-making without formal authority.

Areas to Cover

The context and stakeholders involved
Their approach to influencing others
How they built credibility in the situation
Tactics used to gain support for their position
Outcome of their influence attempt and what they learned

Possible Follow-up Questions

What specific techniques did you use to influence the outcome?
How did you tailor your approach to different stakeholders?
What resistance did you encounter and how did you address it?
How did this experience shape your approach to future situations?

How would you describe your communication style, and how do you adapt it for different audiences?

Areas to Cover

Their natural communication preferences
Awareness of different audience needs
Examples of adapting communication approach
Experience with executive communications
Methods for ensuring message clarity and impact

Possible Follow-up Questions

How do you prepare for high-stakes presentations or communications?
What feedback have you received about your communication style?
How do you ensure complex information is understood by different audiences?
What communication channels do you find most effective for different situations?

How do you manage competing priorities and help executives make decisions about resource allocation?

Areas to Cover

Their prioritization framework or methodology
Experience managing multiple high-priority initiatives
How they've helped leaders make difficult trade-off decisions
Approach to communicating priorities to stakeholders
Examples of realigning resources based on changing priorities

Possible Follow-up Questions

What factors do you consider when prioritizing initiatives?
How do you handle situations where key stakeholders disagree on priorities?
How do you maintain focus on strategic priorities amid daily operational demands?
What tools or systems have you found effective for priority management?

Interview Scorecard

Strategic Thinking

0: Not Enough Information Gathered to Evaluate
1: Shows limited strategic perspective; focuses primarily on tactical execution
2: Demonstrates some strategic awareness but struggles to connect execution to broader vision
3: Effectively balances strategic thinking with operational execution
4: Exceptional ability to see big picture, identify patterns, and translate strategy into action

Communication Skills

0: Not Enough Information Gathered to Evaluate
1: Communication lacks clarity or tailoring to audience
2: Communicates adequately but may not adjust style effectively
3: Clear, articulate communicator who adapts approach for different contexts
4: Exceptional communicator who conveys complex information with remarkable clarity and impact

Executive Presence

0: Not Enough Information Gathered to Evaluate
1: Lacks confidence or authority in presentation
2: Shows some executive qualities but may not consistently project leadership presence
3: Projects confidence, credibility, and professionalism appropriate for the role
4: Exceptional presence that commands respect and instills confidence

Increase Executive Effectiveness Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to significantly enhance executive effectiveness
2: May provide some support but limited impact on executive effectiveness
3: Likely to effectively amplify executive impact through strategic support
4: Exceptional potential to transform executive effectiveness through outstanding support capabilities

Drive Strategic Initiatives Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to successfully drive complex strategic initiatives
2: May complete some initiatives but likely to face challenges with more complex efforts
3: Likely to successfully drive multiple strategic initiatives to completion
4: Exceptional capability to lead strategic initiatives with outstanding results

Establish Effective Communication Channels Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to establish effective communication systems
2: May improve some communication flows but gaps likely to remain
3: Likely to create effective communication channels across stakeholder groups
4: Exceptional potential to transform organizational communication effectiveness

Recommendation

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Leadership Assessment (Work Sample)

Directions for the Interviewer

This assessment evaluates the candidate's ability to handle core Chief of Staff responsibilities in a simulated environment. The exercise tests the candidate's strategic thinking, prioritization skills, communication abilities, and judgment – all critical competencies for success in this role.

Send the exercise materials to the candidate 24 hours before the interview to allow for preparation. During the 60-minute session, you'll spend 40-45 minutes on the role play exercise and 15-20 minutes on follow-up questions and candidate questions.

Observe how the candidate structures their approach, the quality of their analysis, their communication style, and their ability to handle challenging questions. Pay particular attention to how they balance competing priorities and make recommendations, as these are crucial skills for a Chief of Staff.

Directions to Share with Candidate

This assessment simulates aspects of the Chief of Staff role to understand how you would approach real-world challenges. You'll receive materials 24 hours before our meeting that outline a scenario requiring your analysis and recommendations. During our session, you'll present your approach as if briefing the [Executive Title], followed by a Q&A discussion where I may introduce new information or challenges. We'll conclude with time for your questions about the role or company.

Exercise: Executive Briefing Simulation

Scenario: You've been the Chief of Staff at [Company] for one month. The [Executive Title] has a board meeting in two days and has asked you to prepare a briefing on three pressing issues:

A major strategic initiative is behind schedule and over budget
An unexpected competitive threat has emerged in the market
There's an internal conflict between two department heads that's affecting progress on a key project

Materials Provided to Candidate (24 hours prior):

Background on the strategic initiative, budget/timeline issues, and stakeholders involved
Information about the competitive threat, including market data
Context on the department conflict, including perspectives from both leaders
The [Executive Title]'s calendar for the next week (heavily booked)
Company organizational chart

Exercise Format:

Candidate presents a 15-minute briefing covering:

Analysis of the three issues, their potential impact, and priority level
Recommendations for addressing each issue
Suggested talking points for the board meeting
Proposed next steps and timeline

25-minute discussion/role play where you, as the interviewer, will:

Ask challenging questions about their analysis and recommendations
Introduce new complications (e.g., "The board chair just called and is particularly concerned about the competitive threat")
Test how they handle conflicting priorities

Interview Scorecard

Strategic Analysis

0: Not Enough Information Gathered to Evaluate
1: Analysis is superficial or misses key implications
2: Identifies main issues but may miss some nuances or connections
3: Strong analysis that identifies key issues and their strategic implications
4: Exceptional analysis demonstrating deep insight into complex situations

Prioritization & Decision-Making

0: Not Enough Information Gathered to Evaluate
1: Struggles to establish clear priorities or make sound recommendations
2: Establishes reasonable priorities but rationale may lack depth
3: Effectively prioritizes issues with clear, well-reasoned recommendations
4: Exceptional ability to prioritize competing demands with sophisticated decision framework

Executive Communication

0: Not Enough Information Gathered to Evaluate
1: Communication lacks structure, clarity, or executive-level polish
2: Communicates adequately but presentation could be more concise or compelling
3: Clear, well-structured communication appropriate for executive audience
4: Exceptional ability to communicate complex information in a compelling, executive-ready format

Adaptability

0: Not Enough Information Gathered to Evaluate
1: Struggles to adapt to new information or challenging questions
2: Shows some flexibility but may be thrown off by unexpected challenges
3: Adapts well to new information and handles challenges effectively
4: Exceptional adaptability, seamlessly incorporating new information and turning challenges into opportunities

Increase Executive Effectiveness Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to enhance executive effectiveness through preparation and support
2: May provide adequate support but limited impact on executive effectiveness
3: Likely to significantly enhance executive effectiveness through quality preparation
4: Exceptional capability to transform executive effectiveness through outstanding support

Drive Strategic Initiatives Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to successfully manage complex initiatives to completion
2: May advance initiatives but with potential gaps in execution
3: Likely to successfully drive initiatives with effective planning and follow-through
4: Exceptional ability to advance complex initiatives with superior results

Implement Process Improvements Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to identify or implement valuable process improvements
2: May implement modest improvements but miss larger opportunities
3: Likely to successfully identify and implement valuable process improvements
4: Exceptional ability to transform processes for significantly enhanced effectiveness

Recommendation

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Chronological Interview

Directions for the Interviewer

This in-depth interview explores the candidate's career progression, focusing on achievements, leadership experiences, and growth. The goal is to understand the candidate's background in detail and evaluate patterns of success, leadership style, and fit for the Chief of Staff role. This interview provides crucial context for assessing the candidate's readiness to serve as a strategic partner to your executive.

Structure the interview chronologically, starting with the candidate's earliest relevant experience and moving forward. For each role, use the questions below to understand responsibilities, accomplishments, challenges, and lessons learned. Spend more time on recent, relevant roles and less on earlier positions.

Listen for evidence of:

Increasing scope of responsibility and impact
Experience working directly with executives
Track record of successful project and initiative management
Growth in leadership and strategic thinking capabilities
Patterns in how they approach challenges and relationships

Allow 60-75 minutes for this interview, reserving 10 minutes for candidate questions.

Directions to Share with Candidate

In this conversation, we'll explore your career journey in detail, focusing on your key experiences, achievements, and growth. We'll walk through your professional history chronologically, discussing your roles, responsibilities, and impact. I'm interested in understanding not just what you did, but how you approached challenges, what you learned, and how you've grown as a leader. Please feel free to ask clarifying questions along the way.

Interview Questions

To start, I'd like to understand which aspects of your career journey have best prepared you for a Chief of Staff role.

Areas to Cover

Key experiences that relate directly to this role
Skills developed across different positions
Evolution of their leadership approach
Pattern of roles/projects that demonstrate relevant capabilities
Self-awareness about strengths and areas for development

Possible Follow-up Questions

Which experiences have most shaped your leadership philosophy?
How has your approach to supporting executives evolved over time?
What aspects of your background do you see as most relevant to this position?
What skills have you deliberately worked to develop throughout your career?

Let's start with [earliest relevant role]. What were your main responsibilities, and what key achievements are you most proud of from this time?

Areas to Cover

Scope of role and key responsibilities
Major projects or initiatives led
Relationship with leadership/management
Challenges faced and how they were addressed
Growth and development during this period

Possible Follow-up Questions

How did your responsibilities evolve during your time in this role?
What was the most challenging aspect of this position?
How did you measure success in this role?
What key relationships were most important to your success?

What prompted your transition from [previous role] to [next role], and how did your responsibilities change?

Areas to Cover

Decision-making process for career moves
How each move built on previous experience
Expansion of skills and responsibilities
Adaptation to new environments/cultures
Career trajectory and intentionality

Possible Follow-up Questions

What were you looking for in your next opportunity?
How did you navigate the transition between roles?
What new skills or capabilities did you develop in this role?
How did your leadership approach evolve with this transition?

In your role at [company with most relevant experience], tell me about a situation where you had to navigate complex organizational dynamics to achieve results.

Areas to Cover

The specific organizational challenge
Stakeholders involved and their perspectives
Strategy for building alignment
Communication approach
Outcome and lessons learned

Possible Follow-up Questions

How did you identify the key stakeholders and understand their positions?
What resistance did you encounter and how did you address it?
How did you build trust with different constituents?
What would you do differently if faced with a similar situation?

Describe your experience working directly with executive leadership. What have you learned about effectively supporting senior leaders?

Areas to Cover

Nature of executive relationships
Understanding of executive priorities and constraints
Approaches to managing up effectively
Examples of serving as a trusted advisor
Lessons learned about executive effectiveness

Possible Follow-up Questions

How have you helped make executives more effective?
What have you found to be the most challenging aspect of supporting senior leaders?
How do you balance being a trusted advisor with challenging executive thinking?
How have you helped executives navigate difficult decisions?

Tell me about the most significant strategic initiative you've led. What was your approach and what results did you achieve?

Areas to Cover

Initiative scope and strategic importance
Their leadership role and approach
How they managed stakeholders and resources
Challenges encountered and addressed
Outcomes and impact on the organization

Possible Follow-up Questions

How did you gain alignment on the initiative's objectives and approach?
What obstacles did you face and how did you overcome them?
How did you measure success and track progress?
What would you do differently if leading this initiative again?

Looking at your career as a whole, how would you describe your leadership style and how it has evolved?

Areas to Cover

Self-awareness about leadership approach
Growth and development as a leader
Adaptation to different contexts and teams
Strengths and development areas
Approach to developing others

Possible Follow-up Questions

How has feedback shaped your leadership approach?
How do you adapt your style for different situations or individuals?
What leadership principles have remained constant throughout your career?
What aspect of your leadership are you currently working to develop?

Interview Scorecard

Leadership Experience

0: Not Enough Information Gathered to Evaluate
1: Limited leadership experience or effectiveness
2: Some leadership experience but may lack depth in key areas
3: Strong track record of effective leadership in relevant contexts
4: Exceptional leadership history with proven impact across multiple roles

Strategic Impact

0: Not Enough Information Gathered to Evaluate
1: Limited evidence of driving strategic initiatives or creating significant impact
2: Some strategic contributions but impact may be limited in scope
3: Clear history of leading strategic initiatives with meaningful results
4: Exceptional track record of driving high-impact strategic initiatives

Executive Partnership

0: Not Enough Information Gathered to Evaluate
1: Limited experience working directly with executive leadership
2: Some experience with executives but may not have served as close advisor
3: Strong history of effectively supporting and advising senior leaders
4: Exceptional track record as trusted executive partner and advisor

Career Progression

0: Not Enough Information Gathered to Evaluate
1: Limited growth in responsibility or scope
2: Some progression but may have plateaued or taken lateral moves
3: Clear pattern of growth and increasing responsibility
4: Exceptional career trajectory showing consistent advancement and impact

Increase Executive Effectiveness Outcome

0: Not Enough Information Gathered to Evaluate
1: Career history suggests limited ability to enhance executive effectiveness
2: May provide some support value but impact on executive effectiveness uncertain
3: Career demonstrates ability to significantly enhance executive effectiveness
4: Exceptional history of transforming executive effectiveness through partnership

Drive Strategic Initiatives Outcome

0: Not Enough Information Gathered to Evaluate
1: Limited evidence of successfully driving strategic initiatives
2: Some success with initiatives but may struggle with more complex efforts
3: Strong track record of successfully driving strategic initiatives
4: Exceptional history of leading high-impact strategic initiatives to successful completion

Establish Effective Communication Outcome

0: Not Enough Information Gathered to Evaluate
1: Limited evidence of creating effective communication systems
2: Some success improving communication but impact may be limited
3: Demonstrated ability to establish effective communication channels
4: Exceptional track record of transforming organizational communication

Recommendation

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Strategic Leadership Interview

Directions for the Interviewer

This interview assesses the candidate's strategic thinking capabilities and leadership approach – critical competencies for a successful Chief of Staff. Focus on evaluating how the candidate analyzes complex situations, develops strategic recommendations, and drives execution of initiatives. This is also an opportunity to assess their ability to effectively partner with executives and lead through influence.

Structure the interview around behavioral questions that explore past experiences related to strategic leadership, focusing on both their analytical process and execution capabilities. Probe deeply into their examples to understand their specific contributions, approach to challenges, and the outcomes they achieved.

Listen for:

Depth of strategic thinking and ability to connect tactical actions to broader vision
Approach to gathering and analyzing information to inform decisions
Skill in translating strategy into executable plans
Experience leading cross-functional initiatives
Ability to navigate ambiguity and organizational complexity

Allow 60 minutes for this interview, reserving 10 minutes for candidate questions.

Directions to Share with Candidate

In this conversation, we'll focus on your approach to strategic leadership and execution. I'm interested in understanding how you analyze complex situations, develop strategic recommendations, and drive initiatives to completion. We'll discuss specific examples from your experience that demonstrate these capabilities. Please provide detailed examples, including the context, your specific actions, and the results achieved.

Interview Questions

Tell me about a time when you identified a strategic opportunity that others had overlooked and how you developed and implemented a plan to capitalize on it. (Strategic Thinking)Areas to Cover

How they identified the opportunity
Analysis process and information gathered
Strategy development approach
How they built support for their vision
Implementation plan and execution
Results achieved and lessons learned

Possible Follow-up Questions

What analysis or information led you to spot this opportunity?
How did you validate your assumptions?
How did you gain buy-in from stakeholders?
What obstacles did you encounter during implementation and how did you address them?

Describe a situation where you had to translate a high-level strategic vision into concrete action plans. (Execution Excellence)Areas to Cover

The strategic vision and its objectives
Their approach to breaking down strategy into executable components
How they established priorities and timelines
Methods for tracking progress and ensuring accountability
How they managed stakeholders during the process
Outcomes achieved and lessons learned

Possible Follow-up Questions

How did you determine which initiatives would have the greatest strategic impact?
How did you communicate the strategy and plans to different stakeholders?
What systems or processes did you put in place to track progress?
How did you handle situations where execution deviated from the plan?

Tell me about a complex, ambiguous situation you faced and how you navigated it to achieve results. (Adaptability)Areas to Cover

Nature of the ambiguity or complexity
Initial approach to understanding the situation
How they created structure or clarity
Decision-making process in the face of uncertainty
How they adapted as new information emerged
Results achieved and lessons learned

Possible Follow-up Questions

What frameworks or approaches helped you navigate the ambiguity?
How did you make decisions when you didn't have all the information?
How did you help others remain productive amid the uncertainty?
How did this experience shape your approach to future ambiguous situations?

Describe a time when you helped an executive think through a difficult strategic decision. (Executive Partnership)Areas to Cover

Nature of the decision and its strategic importance
How they structured the decision-making process
Information/analysis they provided to support the decision
How they presented different perspectives or options
Their approach to providing advice while respecting executive authority
Outcome of the decision and lessons learned

Possible Follow-up Questions

How did you gather and analyze information to support this decision?
How did you present complex or potentially negative information?
How did you handle disagreement or push back from the executive?
What did you learn about effectively supporting executive decision-making?

Tell me about a time when you had to drive change across multiple departments or functions. (Influence Without Authority)Areas to Cover

The change initiative and its strategic importance
Stakeholders involved and their varying perspectives
How they built support and alignment
Methods of influence used across different groups
How they overcame resistance
Results achieved and lessons learned

Possible Follow-up Questions

How did you identify key stakeholders and understand their perspectives?
What resistance did you encounter and how did you address it?
How did you maintain momentum when the change process slowed?
What would you do differently if leading this change again?

Interview Scorecard

Strategic Thinking

0: Not Enough Information Gathered to Evaluate
1: Limited strategic perspective; focuses primarily on tactical execution
2: Shows basic strategic awareness but may miss broader implications
3: Strong strategic thinker who connects initiatives to organizational vision
4: Exceptional strategic capacity with ability to identify non-obvious opportunities

Execution Excellence

0: Not Enough Information Gathered to Evaluate
1: Struggles to translate strategy into effective action plans
2: Can execute basic plans but may miss details or face challenges with complex initiatives
3: Effectively translates strategy into clear, actionable plans with strong follow-through
4: Exceptional execution skills with outstanding attention to detail and results

Adaptability

0: Not Enough Information Gathered to Evaluate
1: Struggles in ambiguous situations; seeks excessive structure
2: Can manage some ambiguity but may become less effective in highly uncertain environments
3: Effectively navigates ambiguity and creates clarity for self and others
4: Thrives in ambiguous situations; creates opportunity from uncertainty

Executive Partnership

0: Not Enough Information Gathered to Evaluate
1: Limited experience or effectiveness in supporting executive decision-making
2: Provides adequate support but may not fully understand executive perspective
3: Strong advisor who effectively supports and enhances executive decision-making
4: Exceptional partner who significantly elevates executive effectiveness

Influence Without Authority

0: Not Enough Information Gathered to Evaluate
1: Struggles to influence without direct authority
2: Can influence in some situations but may face challenges with resistant stakeholders
3: Effectively influences across functions and levels through relationships and persuasion
4: Exceptional ability to build coalitions and drive change without formal authority

Drive Strategic Initiatives Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to successfully drive complex strategic initiatives
2: May complete some initiatives but will likely struggle with more complex efforts
3: Likely to successfully drive multiple strategic initiatives to completion
4: Exceptional capability to lead strategic initiatives with outstanding results

Increase Executive Effectiveness Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to significantly enhance executive effectiveness
2: May provide some support but limited impact on executive effectiveness
3: Likely to effectively amplify executive impact through strategic support
4: Exceptional potential to transform executive effectiveness

Implement Process Improvements Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to identify or implement valuable process improvements
2: May implement modest improvements but miss larger opportunities
3: Likely to successfully identify and implement valuable process improvements
4: Exceptional ability to transform processes for significantly enhanced effectiveness

Recommendation

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Communication & Stakeholder Management Interview

Directions for the Interviewer

This interview assesses the candidate's communication capabilities and stakeholder management skills – essential competencies for a Chief of Staff who must effectively represent the executive, build relationships across the organization, and navigate complex interpersonal dynamics. Focus on evaluating how the candidate communicates in different contexts, builds relationships, manages conflicts, and influences stakeholders at all levels.

Structure the interview around behavioral questions that explore past experiences related to communication and relationship management. Probe deeply into their examples to understand their approach to crafting messages, building trust, navigating sensitive situations, and managing diverse stakeholders.

Pay attention to:

How they communicate during the interview (clarity, structure, active listening)
Their approach to tailoring communication for different audiences
Experience managing up and representing executives
Skill in navigating conflict and building bridges
Ability to influence without authority

Allow 60 minutes for this interview, reserving 10 minutes for candidate questions.

Directions to Share with Candidate

In this conversation, we'll focus on your communication and stakeholder management capabilities. We'll discuss how you build relationships, craft and deliver messages, navigate complex interpersonal dynamics, and represent leaders to different stakeholders. Please provide specific examples from your experience, including the context, your approach, challenges you faced, and the outcomes you achieved.

Interview Questions

Tell me about a time when you had to communicate a complex or sensitive message to diverse stakeholders. How did you approach it? (Communication Mastery)Areas to Cover

The message and its complexity/sensitivity
Stakeholder analysis and communication strategy
How they tailored the message for different audiences
Channels used and timing considerations
Challenges encountered and how they were addressed
Feedback received and results achieved

Possible Follow-up Questions

How did you determine the communication needs of each stakeholder group?
What resistance or misunderstanding did you encounter and how did you address it?
How did you ensure consistency while tailoring the message?
What would you do differently if communicating this message again?

Describe a situation where you successfully built relationships and influence with senior stakeholders. (Relationship Building)Areas to Cover

The context and stakeholders involved
Their approach to establishing credibility and trust
How they identified stakeholder needs and priorities
Specific relationship-building strategies used
How they leveraged relationships to create impact
Long-term outcomes of the relationships built

Possible Follow-up Questions

How did you initially establish credibility with these stakeholders?
What challenges did you face in building these relationships?
How did you demonstrate value to maintain these relationships?
How have these relationships evolved over time?

Tell me about a time when you had to manage a difficult conflict between stakeholders or departments. (Conflict Management)Areas to Cover

Nature of the conflict and parties involved
Their role in addressing the conflict
How they understood different perspectives
Approach to finding common ground or resolution
Communication techniques used
Outcome of the conflict and lessons learned

Possible Follow-up Questions

How did you identify the underlying causes of the conflict?
What strategies did you use to de-escalate tensions?
How did you build consensus for a resolution?
How did this experience shape your approach to future conflicts?

Describe a time when you had to represent an executive to key stakeholders or make decisions on their behalf. (Executive Representation)Areas to Cover

The context and their representative role
How they ensured alignment with executive's priorities and perspective
Their approach to making decisions or speaking on behalf of the executive
How they handled questions or situations beyond their explicit authority
Feedback from the executive and stakeholders
Impact of their representation

Possible Follow-up Questions

How did you ensure you accurately represented the executive's position?
How did you handle situations where you weren't sure of the executive's stance?
What challenges did you face in representing the executive?
How did you build credibility as the executive's representative?

Tell me about a particularly challenging negotiation or persuasion situation you've managed. (Persuasion & Negotiation)Areas to Cover

The situation and stakes involved
Their preparation and strategy
Understanding of other parties' interests and positions
Techniques used to influence or negotiate
How they handled resistance or objections
Outcome achieved and lessons learned

Possible Follow-up Questions

How did you prepare for this negotiation/persuasion effort?
What was your strategy for addressing resistance?
How did you find areas of mutual benefit or compromise?
What would you do differently in a similar future situation?

Interview Scorecard

Communication Mastery

0: Not Enough Information Gathered to Evaluate
1: Communication lacks clarity, structure, or audience awareness
2: Adequate communicator but may struggle with complex or sensitive messages
3: Strong communicator who adapts effectively to different audiences and contexts
4: Exceptional communication skills with outstanding ability to craft impactful messages

Relationship Building

0: Not Enough Information Gathered to Evaluate
1: Struggles to establish effective relationships, particularly with senior stakeholders
2: Builds adequate relationships but may not leverage them strategically
3: Effectively builds and maintains relationships across levels and functions
4: Exceptional relationship builder who creates strong networks that drive results

Conflict Management

0: Not Enough Information Gathered to Evaluate
1: Avoids conflict or manages it ineffectively
2: Basic conflict management skills but may struggle with complex situations
3: Effectively addresses conflicts and builds constructive resolutions
4: Exceptional ability to transform conflicts into opportunities for collaboration

Executive Representation

0: Not Enough Information Gathered to Evaluate
1: Limited experience or effectiveness in representing executives
2: Can represent executives in basic situations but may struggle with complexity
3: Effectively represents executives with appropriate judgment and credibility
4: Exceptional ability to embody executive perspective and make decisions on their behalf

Persuasion & Negotiation

0: Not Enough Information Gathered to Evaluate
1: Limited persuasion or negotiation effectiveness
2: Some persuasive ability but may not succeed with resistant stakeholders
3: Effectively persuades and negotiates across various contexts
4: Exceptional ability to influence others and create win-win outcomes

Establish Effective Communication Channels Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to establish effective communication systems
2: May improve some communication flows but gaps likely to remain
3: Likely to create effective communication channels across stakeholders
4: Exceptional potential to transform organizational communication effectiveness

Build Trusted Advisor Relationships Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to establish trusted advisor status with leadership
2: May build adequate relationships but limited trusted advisor potential
3: Likely to establish strong trusted advisor relationships
4: Exceptional potential to become an indispensable trusted advisor

Increase Executive Effectiveness Outcome

0: Not Enough Information Gathered to Evaluate
1: Communication approach unlikely to enhance executive effectiveness
2: May provide some communication support but limited impact
3: Communication skills likely to significantly enhance executive effectiveness
4: Exceptional communication capabilities that will transform executive impact

Recommendation

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Executive Team Interview (Optional)

Directions for the Interviewer

This interview gives key executive team members an opportunity to assess the candidate's fit with the leadership team and organizational culture. As a senior leader who would work closely with the Chief of Staff, your assessment of interpersonal dynamics, cultural alignment, and leadership presence is crucial. Focus on evaluating how the candidate would integrate with the team, support the [Executive Title], and contribute to the organization's strategic priorities.

Structure the interview as a conversational assessment of the candidate's experience, working style, and approach to collaboration with senior leadership. This is also an opportunity to share more about how your leadership team operates and to answer the candidate's questions about the organization.

Pay attention to:

How the candidate builds rapport and engages with you as a senior leader
Their understanding of executive priorities and challenges
Communication style and executive presence
Ability to balance supporting leadership while providing candid input
Cultural fit and alignment with organizational values

Allow 45-60 minutes for this interview, with ample time for two-way dialogue.

Directions to Share with Candidate

This conversation is an opportunity for us to get to know each other and explore how we might work together. I'll share some context about our leadership team dynamics and priorities, and I'm interested in understanding your approach to supporting executives and collaborating with leadership teams. Please feel free to ask questions throughout our discussion - this is as much about you assessing fit with our organization as it is about our assessment of you.

Interview Questions

Based on what you've learned about our organization and [Executive Title]'s role, what do you see as the key ways you could add value as Chief of Staff?

Areas to Cover

Understanding of organizational context and challenges
Insight into executive needs and constraints
Vision for the Chief of Staff role
Specific ways they would enhance executive effectiveness
Self-awareness about their strengths relative to organizational needs

Possible Follow-up Questions

What aspects of the role would you find most challenging?
How would you approach learning about our organization and leadership team?
What questions do you have about our strategic priorities?
How would you establish credibility with the leadership team?

Tell me about your experience working with executive teams. What have you learned about what makes these relationships effective?

Areas to Cover

Specific experiences with executive teams
Understanding of executive team dynamics
Their role in supporting team effectiveness
Challenges they've encountered and how they've addressed them
Lessons learned about effective collaboration at senior levels

Possible Follow-up Questions

How have you handled disagreements among executive team members?
What approaches have you found most effective for keeping executive teams aligned?
How do you balance supporting individual executives versus the team as a whole?
How do you manage confidentiality within executive contexts?

How would you approach representing [Executive Title] in meetings or communications with the leadership team?

Areas to Cover

Understanding of representational role
How they would ensure alignment with executive's perspective
Approach to building trust and credibility
How they would handle challenging situations
Balance between advocacy and collaboration

Possible Follow-up Questions

How would you prepare for representing the executive in important meetings?
How would you handle situations where you're unsure of the executive's position?
How would you manage pushback from other leaders?
How would you ensure you're adding value rather than creating communication barriers?

Our organization values [key organizational values]. Can you share examples of how you've embodied similar values in your work?

Areas to Cover

Understanding of and alignment with organizational values
Specific examples demonstrating these values in action
Authenticity in their response
Consistency across different examples
How values inform their leadership approach

Possible Follow-up Questions

How do you ensure your values are reflected in your daily work?
Have you ever worked in an organization with different values? How did you navigate that?
How would you help promote these values in your role as Chief of Staff?
How do you handle situations where values may conflict with short-term business needs?

What questions do you have about our leadership team, culture, or how we work together?

Areas to Cover

The quality and depth of their questions
Areas of interest and concern
How they engage in dialogue
What they prioritize in organizational culture
How they're evaluating fit with the organization

Possible Follow-up Questions

Based on what you've learned, what do you see as our team's strengths and challenges?
What else would be helpful for you to know about our team dynamics?
How does our approach compare to leadership teams you've worked with previously?
What excites you most about potentially joining our team?

Interview Scorecard

Executive Team Fit

0: Not Enough Information Gathered to Evaluate
1: Significant concerns about fit with executive team dynamics
2: May fit with some aspects of team but potential misalignment in others
3: Strong alignment with executive team culture and dynamics
4: Exceptional fit; would enhance executive team effectiveness

Leadership Presence

0: Not Enough Information Gathered to Evaluate
1: Lacks the presence needed to be effective with senior leadership
2: Adequate presence but may struggle in high-stakes executive contexts
3: Strong leadership presence appropriate for senior-level interactions
4: Exceptional presence that commands respect while building rapport

Cultural Alignment

0: Not Enough Information Gathered to Evaluate
1: Limited alignment with organizational values and culture
2: Some alignment but potential mismatches in key areas
3: Strong alignment with organizational culture and values
4: Exceptional embodiment of organizational values with potential to strengthen culture

Strategic Understanding

0: Not Enough Information Gathered to Evaluate
1: Limited grasp of organizational strategic context
2: Basic understanding but may miss nuances or implications
3: Strong comprehension of organizational strategy and context
4: Exceptional strategic insight with valuable perspective on organizational priorities

Build Trusted Advisor Relationships Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to establish trusted relationships with executive team
2: May build adequate relationships but limited trusted advisor potential
3: Likely to establish strong trusted relationships with leadership
4: Exceptional potential to become a valuable advisor to the entire leadership team

Increase Executive Effectiveness Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to significantly enhance executive effectiveness
2: May provide some support but limited impact on executive effectiveness
3: Likely to effectively amplify executive impact through strategic support
4: Exceptional potential to transform executive effectiveness through partnership

Establish Effective Communication Channels Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to improve executive team communication
2: May enhance some communication aspects but limited broader impact
3: Likely to significantly improve executive team communication effectiveness
4: Exceptional potential to transform communication across leadership

Recommendation

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Board Member Interview (Optional)

Directions for the Interviewer

This interview provides an opportunity for board representation in the hiring process for this critical role. As a board member, your perspective on how the candidate will support the [Executive Title] and interact with the board is invaluable. Focus on assessing the candidate's strategic thinking, judgment, communication skills, and understanding of governance – all crucial for effective engagement with the board.

Structure the interview as a higher-level discussion of the candidate's experience, strategic perspective, and approach to executive support. This is also an opportunity to share your perspective on board expectations and organizational priorities.

Pay particular attention to:

Strategic thinking and business acumen
Executive presence and communication skills
Judgment and discretion with sensitive information
Understanding of governance and board dynamics
Ability to effectively represent and support the [Executive Title]

Allow 45-60 minutes for this interview, ensuring time for substantive dialogue.

Directions to Share with Candidate

This conversation will focus on your strategic perspective, leadership experience, and approach to supporting executives in board-level contexts. As a board member, I'm interested in understanding how you think about organizational strategy, governance, and executive effectiveness. I'll also share some context about our board's expectations and how we work with the executive team. Please feel free to ask questions throughout our discussion.

Interview Questions

Based on what you know about our organization, what do you see as our most significant strategic opportunities and challenges?

Areas to Cover

Understanding of the organization's market position and context
Depth of strategic thinking and business acumen
Ability to identify non-obvious opportunities or risks
Balanced perspective considering multiple stakeholders
Quality of their strategic analysis

Possible Follow-up Questions

How might these strategic considerations influence board priorities?
What information would you want to gather to refine your assessment?
How would you help the [Executive Title] address these challenges?
How have you helped organizations navigate similar situations?

Tell me about your experience preparing executives for board interactions. What have you found to be most effective?

Areas to Cover

Understanding of board dynamics and expectations
Experience supporting executive-board communication
Approach to materials preparation and briefings
Strategies for handling difficult questions or situations
Lessons learned about effective board engagement

Possible Follow-up Questions

How do you ensure an executive is well-prepared for critical board discussions?
How have you helped executives navigate challenging board dynamics?
What approaches have you used to simplify complex information for board consumption?
How do you balance transparency with appropriate filtering of information?

How do you approach handling sensitive or confidential information, particularly in contexts involving the board and executive team?

Areas to Cover

Philosophy on confidentiality and information management
Experience with sensitive situations
Judgment about appropriate information sharing
Systems or practices they use to maintain confidentiality
How they build trust while maintaining appropriate boundaries

Possible Follow-up Questions

How do you determine what information should be shared and with whom?
How have you handled situations where you had information others wanted but shouldn't have?
How do you manage relationships when you're privy to sensitive information?
What systems have you used to protect confidential information?

Describe a situation where you had to help an executive navigate a particularly challenging strategic decision with board implications.

Areas to Cover

The strategic decision and its board implications
Their role in supporting the decision-making process
How they helped the executive think through board perspectives
Their approach to preparing materials and communications
Outcome of the situation and lessons learned

Possible Follow-up Questions

How did you help the executive consider different stakeholder perspectives?
What frameworks or approaches did you use to structure the decision?
How did you prepare the executive for board questions or concerns?
What would you do differently if facing a similar situation?

What questions do you have about our board's expectations, governance approach, or relationship with the executive team?

Areas to Cover

Quality and depth of their questions
Understanding of governance and board dynamics
Areas of interest or concern
How they think about board-executive relationships
What they prioritize in governance structure

Possible Follow-up Questions

Based on what you've learned, how would you approach supporting the [Executive Title] in our specific governance context?
What aspects of our governance structure seem most distinctive to you?
How does our approach compare to other boards you've worked with?
What would be most important for you to learn about our board to be effective?

Interview Scorecard

Strategic Perspective

0: Not Enough Information Gathered to Evaluate
1: Limited strategic insight or business acumen
2: Basic strategic understanding but may miss important nuances
3: Strong strategic perspective with good business judgment
4: Exceptional strategic insight with sophisticated understanding of business context

Board Engagement Readiness

0: Not Enough Information Gathered to Evaluate
1: Limited understanding of board dynamics or governance
2: Basic understanding but may struggle with complex board situations
3: Strong grasp of governance and board engagement principles
4: Exceptional understanding of board dynamics with proven effectiveness in governance contexts

Executive Communication

0: Not Enough Information Gathered to Evaluate
1: Communication lacks the polish and precision needed for board contexts
2: Adequate communication but may not consistently meet board-level standards
3: Excellent communication appropriate for senior governance contexts
4: Exceptional communication that would enhance board-executive dialogue

Judgment & Discretion

0: Not Enough Information Gathered to Evaluate
1: Concerning judgment or approach to confidential information
2: Generally sound judgment but potential gaps in certain contexts
3: Excellent judgment with appropriate handling of sensitive matters
4: Exceptional judgment that inspires complete confidence

Increase Executive Effectiveness Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to enhance executive effectiveness in board contexts
2: May provide basic support but limited impact on executive-board dynamics
3: Likely to significantly enhance executive effectiveness with the board
4: Exceptional potential to transform executive-board engagement

Drive Strategic Initiatives Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to effectively support strategic initiatives at board level
2: May provide some strategic support but impact likely limited
3: Likely to effectively support board-level strategic initiatives
4: Exceptional capability to advance strategic initiatives with board alignment

Establish Effective Communication Channels Outcome

0: Not Enough Information Gathered to Evaluate
1: Unlikely to improve executive-board communication
2: May enhance some aspects of communication but limited broader impact
3: Likely to significantly improve executive-board communication
4: Exceptional potential to transform board-executive communication

Recommendation

1: Strong No Hire
2: No Hire
3: Hire
4: Strong Hire

Debrief Meeting

Directions for Conducting the Debrief Meeting

The Debrief Meeting is an open discussion for the hiring team members to share the information learned during the candidate interviews. Use the questions below to guide the discussion.

Start the meeting by reviewing the requirements for the role and the key competencies and goals to succeed. The Chief of Staff role requires someone who can think strategically while executing tactically, communicate effectively with diverse stakeholders, and serve as a trusted partner to the [Executive Title].

The meeting leader should strive to create an environment where it is okay to express opinions about the candidate that differ from the consensus or from leadership's opinions. Given the close working relationship this person will have with the [Executive Title], ensuring alignment with their working style and approach is crucial, but diverse perspectives are still valuable for making the best decision.

Scores and interview notes are important data points but should not be the sole factor in making the final decision. Consider how the candidate would perform across the full spectrum of responsibilities and how they would integrate with the executive team and organization.

Any hiring team member should feel free to change their recommendation as they learn new information and reflect on what they've learned.

Questions to Guide the Debrief Meeting

Does anyone have any questions for the other interviewers about the candidate?

Guidance: The meeting facilitator should initially present themselves as neutral and try not to sway the conversation before others have a chance to speak up.

Are there any additional comments about the Candidate?

Guidance: This is an opportunity for all the interviewers to share anything they learned that is important for the other interviewers to know.

How well does this candidate align with the [Executive Title]'s working style and needs?

Guidance: Given the close partnership nature of this role, alignment with the executive they'll support is crucial. Discuss specific observations about communication style, work approach, and potential chemistry.

Is there anything further we need to investigate before making a decision?

Guidance: Based on this discussion, you may decide to probe further on certain issues with the candidate or explore specific issues in the reference calls.

Has anyone changed their hire/no-hire recommendation?

Guidance: This is an opportunity for the interviewers to change their recommendation from the new information they learned in this meeting.

If the consensus is no hire, should the candidate be considered for other roles? If so, what roles?

Guidance: Discuss whether engaging with the candidate about a different role would be worthwhile.

What are the next steps?

Guidance: If there is no consensus, follow the process for that situation (e.g., it is the hiring manager's decision). Further investigation may be needed before making the decision. If there is a consensus on hiring, reference checks could be the next step.

Reference Checks

Directions for Conducting Reference Checks

Reference checks are a critical final step in validating your assessment of the Chief of Staff candidate. This role requires exceptional trust, judgment, and effectiveness, making thorough reference checks particularly important. Focus on gathering specific examples and context about the candidate's performance in areas directly relevant to the role.

Select references carefully, ideally including at least one executive the candidate has directly supported, peers who have worked closely with them, and direct reports (if applicable). Ask the candidate to facilitate introductions, as their relationship with the references can affect the quality of information you receive.

Conduct reference calls by phone rather than email to allow for follow-up questions and to better assess tone and nuance. Begin each call by explaining the Chief of Staff role and its importance to your organization, then ask targeted questions about the candidate's relevant experience and capabilities.

Remember that reference checks should validate your existing assessment, but also be open to new information that might change your perspective. If you hear something concerning, consider whether additional references might provide more context before making a final decision.

Questions for Reference Checks

In what capacity did you work with [Candidate], and for how long?

Guidance: Start with context-setting questions to understand the reference's relationship with the candidate. Listen for the depth and recency of the relationship, as well as the reference's enthusiasm when describing their connection to the candidate.

How would you describe [Candidate]'s greatest strengths, particularly in relation to supporting executive leadership?

Guidance: Listen for specific examples rather than general statements. Pay attention to strengths that align with your key requirements for the Chief of Staff role, such as strategic thinking, communication, discretion, and execution capabilities.

Can you describe a situation where [Candidate] effectively managed a complex project or initiative? What was their approach and what results did they achieve?

Guidance: This question assesses execution capabilities and project management skills. Listen for how the candidate structured the work, managed stakeholders, addressed challenges, and delivered results. The level of detail in the response often indicates how closely the reference observed the candidate's work.

How would you describe [Candidate]'s communication style and effectiveness, particularly when representing executives or communicating sensitive information?

Guidance: Communication is a critical skill for a Chief of Staff. Listen for examples of how the candidate tailored communications for different audiences, handled difficult conversations, and maintained appropriate confidentiality while ensuring necessary information flow.

How does [Candidate] handle ambiguity or rapidly changing priorities? Can you provide an example?

Guidance: Chief of Staff roles often involve navigating uncertainty and shifting priorities. Listen for the candidate's approach to creating structure amid ambiguity, ability to reprioritize effectively, and resilience when plans change.

If you were in my position, how likely would you be to hire [Candidate] for this Chief of Staff role on a scale of 1-10, and why?

Guidance: This direct question often elicits more candid feedback. Pay attention to not just the number given but the explanation and any hesitations. A truly enthusiastic reference will typically provide a high rating with specific, compelling reasons.

Is there anything else I should know about [Candidate] that would help me make a better hiring decision for this role?

Guidance: This open-ended question often yields valuable insights that wouldn't emerge from more structured questions. Listen carefully for both what is said and what might be conspicuously absent.

Reference Check Scorecard

Executive Support Capability

0: Not Enough Information Gathered to Evaluate
1: Reference expresses significant concerns about effectiveness in supporting executives
2: Reference indicates adequate but not exceptional capability in executive support
3: Reference confirms strong ability to effectively support and enhance executive effectiveness
4: Reference enthusiastically endorses exceptional capability as executive partner

Strategic Execution

0: Not Enough Information Gathered to Evaluate
1: Reference indicates concerns about candidate's ability to execute strategic initiatives
2: Reference suggests adequate execution capability with some limitations
3: Reference confirms strong track record of successfully executing complex initiatives
4: Reference provides compelling examples of exceptional execution capabilities

Communication Effectiveness

0: Not Enough Information Gathered to Evaluate
1: Reference expresses concerns about communication capabilities
2: Reference indicates adequate but inconsistent communication effectiveness
3: Reference confirms consistently strong communication across different contexts
4: Reference enthusiastically endorses exceptional communication capabilities

Judgment & Discretion

0: Not Enough Information Gathered to Evaluate
1: Reference expresses concerns about judgment or handling of sensitive information
2: Reference indicates generally sound judgment with possible limitations
3: Reference confirms strong judgment and appropriate handling of confidential matters
4: Reference emphasizes exceptional judgment that inspires complete confidence

Increase Executive Effectiveness Outcome

0: Not Enough Information Gathered to Evaluate
1: Reference feedback suggests limited ability to enhance executive effectiveness
2: Reference indicates some positive impact on executive effectiveness
3: Reference confirms significant enhancement of executive effectiveness
4: Reference enthusiastically describes transformative impact on executive effectiveness

Drive Strategic Initiatives Outcome

0: Not Enough Information Gathered to Evaluate
1: Reference feedback suggests limited success with strategic initiatives
2: Reference indicates mixed results with strategic initiative execution
3: Reference confirms successful delivery of strategic initiatives
4: Reference enthusiastically describes exceptional strategic initiative results

Establish Effective Communication Outcome

0: Not Enough Information Gathered to Evaluate
1: Reference feedback suggests limited effectiveness in communication systems
2: Reference indicates some improvement in communication but incomplete impact
3: Reference confirms successful establishment of effective communication channels
4: Reference enthusiastically describes transformative impact on communication

Frequently Asked Questions

How many interviewers should be involved in the Chief of Staff hiring process?

Typically, 5-7 interviewers is ideal for a Chief of Staff role. The core interview team should include the executive the candidate will support, 2-3 key stakeholders they'll work closely with, and 1-2 peers or functional experts who can assess specific competencies. For the final candidates, optional interviews with board members or additional executives may be added.

How can we assess a candidate's ability to manage confidential information?

This is a critical capability for a Chief of Staff. Beyond direct questions about confidentiality, observe the candidate's discretion during the interview process. Do they inappropriately share information about previous employers? How do they talk about sensitive situations? Reference checks are also crucial for validating this attribute. Ask references specifically about the candidate's judgment with sensitive information. You may find our article on conducting effective interviews helpful for additional guidance.

What's the most important competency to assess for a Chief of Staff candidate?

While all the competencies in this guide are important, the ability to effectively support and amplify the executive they'll work with is paramount. This requires a combination of strategic thinking, communication skills, and relationship building, but also specific alignment with the executive's working style and needs. The chronological and stakeholder management interviews, combined with the executive's own assessment, are particularly helpful in evaluating this fit.

How do we balance assessing tactical execution skills versus strategic thinking?

A successful Chief of Staff needs both capabilities. The leadership assessment (work sample) is particularly valuable for evaluating this balance, as it simulates a realistic scenario requiring both strategic analysis and practical execution planning. Look for candidates who can "zoom in and zoom out" – shifting between big-picture thinking and detailed execution as needed.

Should we prioritize industry experience for a Chief of Staff candidate?

Industry experience can be helpful but is typically less important than the core competencies outlined in this guide. A candidate with strong strategic thinking, communication skills, and executive partnership capabilities can usually learn industry specifics relatively quickly. That said, for highly specialized or regulated industries, some baseline knowledge may be beneficial.

How can we ensure the Chief of Staff will integrate well with the existing leadership team?

The executive team interview is designed specifically for this purpose, giving key leaders an opportunity to assess cultural and working style fit. Additionally, the communication and stakeholder management interview provides insights into how the candidate builds relationships across different groups. For senior Chief of Staff roles, consider including a social component (like a team lunch) in the interview process.