The Chief of Staff role serves as a strategic partner to executive leadership, acting as a crucial bridge between the C-suite and the rest of the organization. According to executive leadership experts, successful Chiefs of Staff combine strategic thinking with exceptional execution skills, enabling senior leaders to maximize their effectiveness while ensuring organizational priorities advance seamlessly.

For companies looking to hire a Chief of Staff, behavioral interviews provide invaluable insights into how candidates have navigated complex challenges in the past. This multifaceted role requires someone who can effortlessly shift between high-level strategy and tactical execution while managing relationships across all levels of the organization.

The role typically encompasses strategic planning, cross-functional project management, executive communications, decision support, and operational efficiency. A Chief of Staff must be adept at prioritizing competing demands, translating executive vision into actionable plans, and driving results through influence rather than direct authority. They often serve as a trusted advisor, sounding board, and proxy for the executive they support.

When evaluating candidates for this position, focus on behavioral questions that reveal how they've handled situations requiring judgment, discretion, and leadership. Listen for specific examples that demonstrate their ability to organize complex initiatives, navigate sensitive situations, and drive results through others. The most revealing responses will showcase both what the candidate did and their decision-making process, providing insight into how they might perform in your organization's unique environment. Follow-up questions are particularly valuable for understanding the depth of a candidate's experience and their approach to the multifaceted challenges faced by a Chief of Staff.

Interview Questions

Tell me about a time when you had to represent an executive in a high-stakes meeting or negotiation. How did you prepare, and what was the outcome?

Areas to Cover:

• How the candidate prepared to understand the executive's perspective and priorities
• Their approach to building credibility with stakeholders
• How they handled questions or challenges during the meeting
• Their communication style and adaptability
• The outcome of the meeting and any follow-up actions
• Lessons learned from the experience

Follow-Up Questions:

• What specific steps did you take to ensure you accurately represented the executive's position?
• How did you handle any unexpected questions or challenges that arose?
• Looking back, what would you do differently to prepare for a similar situation in the future?
• How did you communicate the results back to the executive you were representing?

Describe a situation where you had to manage competing priorities from multiple stakeholders while supporting an executive. How did you handle it?

Areas to Cover:

• Their approach to identifying and prioritizing competing demands
• Communication methods used with various stakeholders
• How they maintained relationships while setting boundaries
• Decision-making process for resource allocation
• How they kept the executive informed
• The outcome and impact of their prioritization decisions

Follow-Up Questions:

• What framework or criteria did you use to prioritize these competing demands?
• How did you communicate decisions about priorities to stakeholders whose requests were deprioritized?
• What role did the executive play in your prioritization process?
• How did this experience shape your approach to managing competing priorities now?

Share an example of a complex, cross-functional project that you coordinated. What challenges did you face, and how did you overcome them?

Areas to Cover:

• Their project management approach and coordination methods
• How they identified and managed project risks
• Techniques used to gain buy-in across different departments
• How they resolved conflicts or bottlenecks
• Methods for tracking progress and ensuring accountability
• The project outcome and lessons learned

Follow-Up Questions:

• How did you ensure accountability across teams that didn't directly report to you?
• What was the most significant obstacle you encountered, and how did you address it?
• How did you keep executives informed of progress without overwhelming them with details?
• What would you do differently if you were to lead a similar project today?

Tell me about a time when you needed to shield your executive from unnecessary distractions while still ensuring they had visibility into important issues. How did you approach this balance?

Areas to Cover:

• Their filtering process for determining what required executive attention
• How they maintained awareness of potential issues
• Communication methods used to brief the executive
• Systems implemented to manage information flow
• Examples of successfully preventing distractions
• Instances where they ensured critical information reached the executive

Follow-Up Questions:

• What criteria did you use to determine what warranted the executive's attention?
• How did you ensure you weren't filtering out information that might later prove important?
• How did you communicate your filtering approach to the broader organization?
• How did you build trust with your executive around your judgment in this area?

Describe a time when you had to deliver difficult news or feedback to your executive. How did you approach the conversation?

Areas to Cover:

• Their preparation process for the conversation
• The communication approach and timing they chose
• How they framed the message constructively
• Their handling of the executive's reaction
• Any solutions or recommendations they presented
• The outcome and relationship impact

Follow-Up Questions:

• What made this particular conversation challenging?
• How did you decide on the right timing and setting for this conversation?
• What was the executive's reaction, and how did you respond to it?
• How did this conversation affect your working relationship moving forward?

Tell me about a situation where you identified an opportunity for operational improvement that would impact the executive's effectiveness. How did you approach implementing the change?

Areas to Cover:

• How they identified the opportunity for improvement
• Their process for analyzing the potential impact
• How they pitched the idea to the executive
• The implementation strategy they developed
• Any resistance encountered and how they addressed it
• The results achieved and lessons learned

Follow-Up Questions:

• How did you quantify or demonstrate the potential impact of your proposed change?
• What stakeholders did you need to involve to implement this change successfully?
• What challenges did you encounter during implementation, and how did you overcome them?
• How did you measure the success of this operational improvement?

Share an example of when you had to gather and synthesize complex information from multiple sources to support an executive decision. What was your approach?

Areas to Cover:

• Their information gathering methodology
• How they evaluated source credibility and managed conflicting data
• Their process for synthesizing and distilling complex information
• The format and presentation of their findings
• How they handled uncertainties or gaps in information
• The impact of their analysis on the decision-making process

Follow-Up Questions:

• How did you ensure the accuracy and reliability of the information you collected?
• What frameworks or tools did you use to analyze and organize the information?
• How did you present your findings to make them actionable for the executive?
• Were there any critical knowledge gaps, and how did you account for them?

Describe a time when you had to manage a crisis or unexpected problem on behalf of your executive. What steps did you take to address the situation?

Areas to Cover:

• Their initial assessment and response to the crisis
• How they determined what needed the executive's attention versus what they could handle
• Communication strategies used with various stakeholders
• Their decision-making process under pressure
• Resources or support they leveraged
• The resolution and any preventative measures implemented afterward

Follow-Up Questions:

• How did you decide what aspects of the crisis required the executive's direct involvement?
• What communication channels did you establish during this crisis?
• How did you maintain composure and clear thinking during this stressful situation?
• What systems or processes did you put in place to prevent similar issues in the future?

Tell me about a time when you had to build relationships with key stakeholders to advance an executive's agenda. How did you approach these relationships?

Areas to Cover:

• Their strategy for identifying key stakeholders
• Methods used to understand stakeholder interests and concerns
• Their approach to building trust and credibility
• How they navigated organizational politics
• Specific examples of how these relationships helped advance objectives
• Any challenges encountered and how they were addressed

Follow-Up Questions:

• How did you identify which stakeholders were most critical to your executive's success?
• What techniques did you use to quickly establish rapport and credibility?
• How did you manage situations where stakeholder interests conflicted with executive priorities?
• How did you leverage these relationships to overcome obstacles or resistance?

Share an example of when you had to manage up and influence your executive's thinking or approach on an important matter. How did you handle this?

Areas to Cover:

• Their assessment of when and why influence was needed
• The approach they took to present alternative viewpoints
• How they balanced respect with the need for honest counsel
• Specific tactics used to influence effectively
• The executive's response and the ultimate outcome
• The impact on their working relationship

Follow-Up Questions:

• How did you determine this was a situation that warranted pushing back or offering an alternative view?
• What specific techniques did you use to frame your perspective in a way the executive would be receptive to?
• How did you respond if the executive initially disagreed with your viewpoint?
• How did you build credibility with your executive that allowed for this type of influence?

Describe a situation where you had to maintain confidentiality while still coordinating effectively with others. How did you balance these competing needs?

Areas to Cover:

• Their understanding of confidentiality boundaries
• How they determined what information could be shared and with whom
• Methods used to maintain trust while limiting information
• Strategies for coordinating work without disclosing sensitive details
• Any challenges encountered and how they were resolved
• The outcome and any lessons learned

Follow-Up Questions:

• How did you determine appropriate boundaries for what information could be shared?
• What techniques did you use to keep projects moving forward without divulging confidential information?
• How did you respond when pressed for information you couldn't share?
• How did you maintain trust with both your executive and the broader team during this situation?

Tell me about a time when you had to adapt your communication style or approach to better support your executive. What changes did you make and why?

Areas to Cover:

• Their process for recognizing the need to adapt
• Specific observations about the executive's preferences or needs
• The adjustments they made to their communication or work style
• How they implemented these changes
• The impact on their effectiveness and relationship
• Ongoing refinements based on feedback

Follow-Up Questions:

• What signals or feedback helped you recognize the need to adapt your approach?
• What specific changes did you make to your communication style or methods?
• How did you ensure you maintained your own effectiveness while adapting to their preferences?
• How has this experience informed how you approach working with different executives?

Share an example of how you've helped an executive navigate a significant organizational change. What was your role in the process?

Areas to Cover:

• Their understanding of the change and its implications
• How they supported the executive in planning the change
• Their role in communication and messaging
• How they identified and addressed resistance or concerns
• Methods used to monitor implementation progress
• The outcome and lessons learned from the experience

Follow-Up Questions:

• How did you help your executive anticipate potential resistance or challenges?
• What role did you play in crafting and delivering communications about the change?
• How did you gather feedback during the change process?
• What would you do differently if managing a similar change in the future?

Describe a time when you had to say "no" to a request that would have diverted resources from your executive's priorities. How did you handle it?

Areas to Cover:

• Their process for evaluating the request against priorities
• How they communicated the decision tactfully
• Alternative solutions they may have proposed
• Their approach to maintaining relationships despite the refusal
• How they kept the executive informed (or not) about the situation
• The outcome and any resulting impacts

Follow-Up Questions:

• What criteria did you use to determine this request didn't align with priorities?
• How did you frame your response to preserve the relationship?
• Were there any compromises or alternative solutions you were able to offer?
• How did you handle any pushback or escalation that resulted from your refusal?

Tell me about a time when you had to work autonomously on a high-impact initiative with minimal direction. How did you ensure you were on the right track?

Areas to Cover:

• How they clarified objectives and expectations at the outset
• Their approach to planning and organizing the work
• Methods used to validate direction and progress
• How they determined when to escalate issues or seek guidance
• Their communication approach with stakeholders
• The outcome and any course corrections along the way

Follow-Up Questions:

• What steps did you take initially to ensure clarity on objectives and constraints?
• How did you build in checkpoints to confirm you were on the right path?
• When did you decide to make decisions independently versus seeking input?
• What techniques did you use to maintain momentum while working independently?

Frequently Asked Questions

Why are behavioral questions particularly effective for Chief of Staff interviews?

The Chief of Staff role requires exceptional judgment, adaptability, and interpersonal skills that are difficult to assess through hypothetical questions. Behavioral questions reveal how candidates have actually handled complex situations in the past, providing concrete evidence of their capabilities across the diverse responsibilities this role entails. These questions help you understand not just what candidates did, but how they thought through challenges and navigated organizational complexities.

How many behavioral questions should I include in a Chief of Staff interview?

Rather than covering many questions superficially, focus on 3-5 behavioral questions per interview, allowing time for thorough follow-up. This approach encourages candidates to share detailed examples and gives interviewers the opportunity to probe more deeply. For a Chief of Staff role, consider structuring your interview process to cover different competency areas across multiple interviews with various stakeholders.

How can I tailor these questions for candidates coming from different backgrounds?

Focus on the transferable skills and competencies required for the Chief of Staff role rather than specific previous job titles. When interviewing candidates without prior Chief of Staff experience, look for examples from their background that demonstrate relevant capabilities - such as cross-functional coordination, executive communication, or strategic planning - and frame your follow-up questions to explore how those experiences would translate to Chief of Staff responsibilities. Learn more about designing your hiring process for maximum effectiveness.

What should I look for in candidates' responses to these behavioral questions?

Look for specific, detailed examples rather than generalities or hypothetical responses. Strong candidates will clearly articulate the situation, their specific actions, the reasoning behind their decisions, and the measurable results. Pay attention to how they navigated complex interpersonal dynamics, managed competing priorities, and influenced outcomes without formal authority - all critical skills for an effective Chief of Staff. Consider using an interview scorecard to standardize your evaluation process.

How can I ensure a fair assessment across different candidates with varied experiences?

Use a consistent set of core questions for all candidates, focusing on the fundamental competencies required for success in the role. While follow-up questions may vary based on each candidate's specific examples, ensure you're evaluating the same underlying skills and abilities. Document your assessment criteria before interviews begin, and use a structured interview guide to maintain consistency across your hiring team.

Interested in a full interview guide for a Chief of Staff role? Sign up for Yardstick and build it for free.