Essential Work Samples for Evaluating Executive Assistant Candidates

Executive Assistants serve as the backbone of executive productivity, enabling leaders to focus on strategic priorities while ensuring operational excellence behind the scenes. The role requires a unique blend of organizational prowess, communication finesse, discretion, and adaptability that can be difficult to assess through traditional interview questions alone.

While resumes and behavioral interviews provide valuable insights into a candidate's experience and past behaviors, practical work samples offer a window into how candidates actually perform tasks they'll encounter daily. For Executive Assistant roles, these exercises reveal crucial capabilities like prioritization skills, attention to detail, communication style, problem-solving approach, and ability to anticipate needs.

The most effective Executive Assistant hiring processes incorporate realistic scenarios that simulate the challenges and responsibilities of the position. By observing candidates in action, hiring managers can evaluate not just what candidates say they can do, but what they actually demonstrate in real-time.

The following work samples are designed to assess the core competencies required for Executive Assistant excellence. Each exercise targets specific skills while providing candidates an opportunity to showcase their unique strengths. Additionally, incorporating a feedback component allows you to evaluate a candidate's receptiveness to coaching—a critical trait for long-term success in this collaborative role.

By implementing these practical assessments, you'll gain deeper insights into each candidate's capabilities and fit, ultimately leading to more confident hiring decisions and stronger executive-assistant partnerships.

Activity #1: Calendar Management Challenge

This exercise evaluates a candidate's ability to manage complex scheduling demands, prioritize effectively, and resolve conflicts—core responsibilities for any Executive Assistant. It reveals how candidates approach time management, attention to detail, and decision-making when faced with competing priorities.

Directions for the Company:

• Prepare a mock executive calendar for one week that includes several existing appointments, meetings, and commitments.
• Create a list of 5-7 new meeting requests that need to be scheduled, including details like requestor name, purpose, priority level, duration, and flexibility.
• Include at least two scheduling conflicts that require resolution (e.g., two high-priority meetings requested for the same time slot).
• Provide the candidate with the executive's general preferences (e.g., no meetings before 9 AM, prefers to group internal meetings on certain days, needs 30 minutes between meetings when possible).
• Allow 20-25 minutes for the candidate to complete the exercise.

Directions for the Candidate:

• Review the executive's current calendar and the new meeting requests.
• Schedule the new meetings according to priority and the executive's preferences.
• Resolve any scheduling conflicts by proposing alternative times or solutions.
• Prepare a brief email to the executive summarizing your scheduling decisions and any questions you have about priorities.
• Be prepared to explain your reasoning for how you scheduled each meeting and resolved conflicts.

Feedback Mechanism:

• After reviewing the candidate's work, provide specific feedback on one aspect they handled well (e.g., "I appreciated how you prioritized the board meeting and protected preparation time before it").
• Offer one suggestion for improvement (e.g., "The client meeting might have been better scheduled earlier in the week given its importance").
• Ask the candidate to revise one specific element based on your feedback, observing how receptively they incorporate the guidance.

Activity #2: Executive Communication Role Play

This exercise assesses a candidate's written communication skills, professionalism, discretion, and ability to represent an executive effectively. It reveals their judgment in handling sensitive matters and skill in crafting appropriate responses.

Directions for the Company:

• Create 3-4 sample emails that an Executive Assistant might need to handle, such as:
• A frustrated client requesting an urgent meeting with the executive
• An internal team member asking for information that requires discretion
• A high-profile invitation that conflicts with existing commitments
• A vague request that requires clarification before action
• Provide context about the relationships and any relevant background information.
• Allow 25-30 minutes for the candidate to draft responses.

Directions for the Candidate:

• Review each email scenario and draft appropriate responses on behalf of the executive or yourself as the Executive Assistant.
• Consider the tone, level of formality, and information to include or withhold in each response.
• For each email, note whether you would send it directly or have the executive review it first, and why.
• Prioritize which emails should be addressed first and explain your reasoning.
• Be prepared to discuss how you would follow up on each situation after the initial response.

Feedback Mechanism:

• Provide positive feedback on the candidate's strongest response, highlighting specific elements that were effective.
• Offer constructive feedback on one response that could be improved, focusing on tone, clarity, or content.
• Ask the candidate to revise the response that received constructive feedback, observing their ability to incorporate guidance and improve their work.

Activity #3: Travel Planning Scenario

This exercise evaluates a candidate's organizational skills, attention to detail, and ability to anticipate needs—essential qualities for coordinating executive travel. It reveals how thoroughly candidates consider logistics and potential complications.

Directions for the Company:

• Create a scenario for an executive's upcoming business trip that includes:
• Multiple destinations over 3-5 days
• Several meetings with different stakeholders
• Specific executive preferences (e.g., airline preferences, hotel requirements, dietary restrictions)
• At least one logistical challenge (tight connection, meeting in an unfamiliar location, etc.)
• Provide necessary details like meeting times/locations and the executive's general travel preferences.
• Allow 30 minutes for the candidate to develop a travel plan.

Directions for the Candidate:

• Create a comprehensive travel itinerary for the executive's trip.
• Include all transportation details, accommodations, meeting information, and relevant contact information.
• Identify potential issues or challenges and propose solutions or contingency plans.
• List any questions you would ask the executive to better prepare for the trip.
• Prepare a brief pre-trip email to the executive highlighting key information and any items requiring their attention.

Feedback Mechanism:

• Highlight one aspect of the travel plan that demonstrates exceptional foresight or attention to detail.
• Identify one area where additional information or planning would improve the itinerary.
• Ask the candidate to address the improvement area by adding to or revising their plan, observing how they incorporate the feedback and enhance their work.

Activity #4: Executive Meeting Preparation

This exercise assesses a candidate's ability to gather and organize information, prepare materials, and anticipate an executive's needs for an important meeting. It demonstrates research skills, judgment about what's relevant, and presentation of information.

Directions for the Company:

• Create a scenario for an upcoming executive meeting (e.g., board meeting, client presentation, strategic planning session).
• Provide basic information about the meeting purpose, attendees, and general agenda.
• Include some background materials about the topic and participants (company profiles, previous meeting notes, relevant articles).
• Allow 30-35 minutes for the candidate to prepare meeting materials.

Directions for the Candidate:

• Review all provided information about the upcoming meeting.
• Prepare a concise briefing document for the executive that includes:
• Key information about meeting participants (roles, backgrounds, relevant history)
• Critical points to be aware of regarding the meeting topic
• Suggested talking points or questions for the executive
• Any potential issues or sensitivities to be mindful of
• Organize the information in a clear, scannable format that would be easy for a busy executive to review.
• Include any additional materials or preparations you would recommend.

Feedback Mechanism:

• Provide positive feedback on the most valuable or well-presented element of the briefing materials.
• Suggest one way the preparation could be enhanced or made more useful to the executive.
• Ask the candidate to implement your suggestion by revising a portion of their materials, observing how they incorporate feedback and improve their work.

Frequently Asked Questions

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

Each exercise requires 20-35 minutes for completion, plus time for instructions and feedback. We recommend selecting 1-2 exercises most relevant to your specific needs rather than attempting all four. Allow approximately one hour total for a work sample session, including setup, execution, and feedback.

Should we provide these exercises as take-home assignments or conduct them during the interview?

Both approaches have merit. In-person or virtual live exercises allow you to observe how candidates work under pressure and think on their feet. Take-home assignments may provide more polished results and reduce interview time. Consider your priorities and the specific role requirements when deciding.

How should we evaluate candidates who have strong technical skills but seem nervous during the exercises?

Some nervousness is natural during interviews. Focus on the quality of their work and thinking process rather than presentation confidence alone. Consider providing a brief warm-up activity to help candidates get comfortable before beginning the formal assessment.

Can we modify these exercises for remote or hybrid work environments?

Absolutely. These exercises are designed to be conducted virtually or in person. For remote roles, you might place additional emphasis on digital organization, virtual communication skills, and technology proficiency throughout the exercises.

How do we ensure these exercises don't disadvantage candidates without specific software experience?

Focus evaluation on the candidate's approach, organizational thinking, and communication rather than proficiency with specific tools. Allow candidates to use familiar applications or provide simple templates. Clarify that you're assessing problem-solving and organizational skills, not software expertise.

Should we share these exercises with candidates in advance?

Providing general information about the types of exercises helps candidates prepare appropriately without compromising the assessment. For example, you might inform candidates they'll be asked to complete a calendar management exercise without sharing the specific conflicts they'll need to resolve.

Executive Assistants are critical partners in leadership effectiveness, and finding the right match requires thorough evaluation beyond traditional interviews. These practical work samples provide valuable insights into how candidates approach real-world scenarios they'll encounter in the role.

For additional hiring resources, explore Yardstick's suite of AI-powered tools to streamline your hiring process, including our AI Job Description Generator, AI Interview Question Generator, and AI Interview Guide Generator. You can also review our complete Executive Assistant job description template for more insights into this critical role.

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