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Executive Assistant

Cushman & Wakefield · Chicago, IL · $72,250–$85,000 a year · Full time

Posted Sep 15, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you anticipated what an executive needed before they asked.

What they are checking: Whether they think ahead, which is the difference between a good assistant and a great one.

Working in Legal, you'll see confidential information. How do you handle that day to day?

What they are checking: Whether they understand discretion around privileged and sensitive legal matters.

Describe a time you were juggling urgent requests from more than one boss. How did you keep them all satisfied?

What they are checking: Whether they manage competing demands fairly and communicate tradeoffs openly.

Tell me about a mistake you made supporting an executive and how you fixed it.

What they are checking: Whether they own errors quickly and put a fix in place so it doesn't happen again.

How do you build working relationships with the rest of the Legal team, not just the leaders you support?

What they are checking: Whether they contribute to the broader team's operation, which the posting expects.

What would you do

You'd support several senior leaders in the Legal department. Two of them want the same hour on the same day. How do you decide?

What they are checking: Whether they can resolve routine conflicts on their own and know when a priority call belongs to the leaders.

A leader's flight is canceled the night before an international meeting. What do you do?

What they are checking: Whether they can rebook quickly within travel policy and update everyone affected.

What do you put in a briefing packet so a leader walks into a meeting prepared?

What they are checking: Whether they understand how to help leaders use their time well, as the posting stresses.

About the work

Walk me through how you manage a calendar that spans multiple time zones without double-booking or scheduling someone at 3 a.m.

What they are checking: Whether they have reliable tools and habits for complex scheduling across regions.

How do you prepare and reconcile expense reports so they go through cleanly the first time?

What they are checking: Whether they are accurate with receipts, coding and policy so leaders aren't chasing corrections.

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The full job description

As published by Cushman & Wakefield.

Job Title Executive Assistant Job Description Summary We are seeking a highly organized, proactive, and adaptable Executive Assistant to support multiple senior leaders within the Legal department. This role independently manages complex administrative priorities, coordinates day-to-day executive support activities, and helps ensure that leaders are prepared, informed, and able to use their time effectively. The successful candidate anticipates needs, exercises sound judgment within established priorities, and delivers accurate, timely support in a fast-paced environment. This individual manages competing demands across multiple leaders, builds strong working relationships, and contributes to the effective operation of the broader Legal team. Job Description Responsibilities • Provide proactive administrative and operational support to multiple senior Legal leaders, managing priorities, anticipating routine needs, and ensuring timely follow-through. • Own complex, high-volume executive calendars, including scheduling across stakeholders and time zones, resolving routine conflicts, and escalating material prioritization issues when appropriate. • Coordinate domestic and international travel in accordance with company policies and executive preferences, including itineraries, accommodations, transportation, and timely adjustments when plans change. • Prepare, reconcile, and submit accurate executive expense reports, ensuring compliance with company policies and established deadlines. • Coordinate logistics for team meetings and offsites, including scheduling, venues, materials, attendee communications, travel arrangements, vendor coordination, and on-site support. • Prepare and organize agendas, meeting materials, presentations, and other routine executive documents using established templates, content, and direction. • Manage executive correspondence, records, and information with professionalism, discretion, accuracy, and appropriate confidentiality. • Coordinate defined administrative and operational projects, track milestones and action items, and follow up with stakeholders to support timely completion. • Build effective working relationships with senior leaders, administrative colleagues, internal business partners, and external vendors to facilitate communication and execution. • Identify practical improvements to assigned administrative workflows and support the adoption of approved processes and tools. • Provide coverage and knowledge sharing to administrative colleagues as needed to support continuity across the department. • Perform other related duties as required or requested. Qualifications • 3+ years of experience in executive support, business administration, operations coordination, or a related field. • Demonstrated ability to support multiple senior leaders while managing competing priorities, deadlines, and changing business needs. • Experience independently managing complex calendars, travel arrangements, meeting logistics, and expense reporting with a high degree of accuracy and attention to detail. • Strong organizational, communication, and relationship-building skills, with the ability to work effectively and confidently with senior leaders, executive stakeholders, administrative partners, and cross-functional teams. • Ability to anticipate needs, exercise sound judgment, handle sensitive information with discretion, and operate independently while recognizing when escalation is appropriate. • Advanced proficiency in Microsoft 365 and experience with enterprise systems such as Workday and Concur. Cushman & Wakefield also provides eligible employees with an opportunity to enroll in a variety of benefit programs, generally including health, vision, and dental insurance, flexible spending accounts, health savings accounts, retirement savings plans, life, and disability insurance programs, and paid and unpaid time away from work. In addition to a comprehensive benefits package, Cushman and Wakefield provide eligible employees with competitive pay, which may vary depending on eligibility factors such as geographic location, date of hire, total hours worked, job type, business line, and applicability of collective bargaining agreements. The compensation that will be offered to the successful candidate will depend on factors such as whether the position is covered by a collective bargaining agreement, the geographic area in which the work will be performed, market pay rates in that area, and the candidate’s experience and qualifications. The company will not pay less than minimum wage for this role. The compensation for the position is: $ 72,250.00 - $85,000.00 Cushman & Wakefield is an Equal Opportunity employer to all protected groups, including protected veterans and individuals with disabilities. Discrimination of any type will not be tolerated. In compliance with the Americans with Disabilities Act Amendments Act (ADAAA), if you have a disability and would like to request an accommodation in order to apply for a position at Cushman & Wakefield, please call the ADA line at 1-888-365-5406 or email Accommodations@cushwake.com . Please refer to the job title and job location when you contact us. INCO: “Cushman & Wakefield”

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