How to Hire the Perfect Personal Assistant in Chicago

More and more, we hear our clients struggling to keep up with the high demands of life admin whilst managing busy professional schedules personal commitments. Sound familiar? If you’re one of the many families and individuals who find themselves juggling responsibilities, leaving themselves with limited time to focus on what truly matters: their family and personal pursuits, it may be time to consider hiring a Personal Assistant (PA) or Family Assistant. In this blog, we’ll break down exactly how a PA can help your busy family and what you need to look for so that you can hire the perfect personal assistant.

What is a Personal Assistant or Family Assistant?

Unlike in the corporate world where a PA is assigned to a senior member of staff, a personal assistant to a family is a professional who is adept at streamlining daily tasks and providing essential support, ensuring that families can reclaim precious moments for themselves.

Things you could ask your personal assistant to help with are:

  • Running personal errands, like picking up dry-cleaning

  • Managing calendars

  • Meal-planning

  • Organizing gifts

  • Helping manage family paperwork

  • Co-ordinating family travel

The role of personal assistant to a family has some key differences to the role of a house manager or nanny, so be sure to list out what is expected in any job description.

At My Household Managed, a Chicago-based domestic staff recruitment agency, we understand the significance of finding the perfect match to manage your household seamlessly. Here are our essential tips to consider when hiring a Personal Assistant to enrich your life and family experiences.

What to Look For When Hiring a Personal Assistant

  1. Experience and Skillset

    Inquire about their previous experiences and skills relevant to household management. Assess their proficiency in managing calendars, organizing events, handling personal correspondence. At interview, ask if they have any specialized skills or interests, like culinary expertise or childcare.

  2. Problem-Solving Scenarios

    Present hypothetical situations relevant to household management and observe how candidates strategize and approach problem-solving. Ask about a time they handled a challenging situation to gauge their resourcefulness and adaptability. Consider whether this is the same way you would deal with a situation.

  3. Communication and Interpersonal Skills

    Effective communication is key in this role. Assess their communication style, ability to maintain confidentiality, and professionalism in dealing with various stakeholders, including family members, vendors, and guests.

  4. Technology Proficiency

    In today's digital age, a tech-savvy assistant is invaluable. Inquire about their familiarity with relevant software, productivity tools, and their ability to adapt to new technologies that can streamline household operations.

  5. References and Background Checks

    Request references and conduct thorough background checks to ensure credibility, reliability, and integrity. Speak with previous employers or contacts to gain insights into their work ethic and reliability.

Qualities to Look for in the Ideal Candidate:

  1. Good Chemistry and Compatibility

    A good working relationship between the employer and the Personal Assistant is crucial. Look for someone whose personality aligns with your family's values, communication style, and work ethic. Chemistry and mutual respect create a more productive and enjoyable working relationship.

  2. Flexibility and Adaptability

    Household needs may vary, and flexibility in schedule and tasks is essential. Seek candidates willing to adapt to evolving situations, whether it involves traveling, attending events, or adjusting schedules as needed.

  3. Shared Values and Ethics

    Look for someone whose values align with your family's principles and ethics. A shared understanding of confidentiality, discretion, and respect for privacy is vital in this role.

  4. Initiative and Proactiveness

    An exceptional PA takes initiative and anticipates needs before they arise. Assess their ability to be proactive in managing tasks and providing solutions independently.

  5. Professionalism and Discretion

    Confidentiality is paramount in a private household. Seek candidates who exhibit professionalism, discretion, and the ability to handle sensitive information with utmost confidentiality and tact.

At My Household Managed, our mission is to pair high-net-worth families in Chicago with top-tier Personal Assistants who can efficiently manage households, allowing families to relish more quality time together. Hiring the perfect Personal Assistant is a transformative investment, streamlining your life and enabling you to focus on what truly matters—cherishing moments with your loved ones.


You’ve got enough on your plate in your day-to-day life — let us make your life easier by handling your unique household staffing needs.

If you are a family looking to hire a household employee or other home service, register with My Household Managed.

If you are a professional nanny, house manager, or other household employee looking for a job, apply at My Household Managed.



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