Hiring Guide for Personal Assistants in Chicago
Business leaders use up to 36% of their workweek handling minor admin tasks.


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How do business leaders save more time for revenue-generating activities?
Did you know that an average decision-maker spends around 36% of their week handling minor admin tasks?
That’s too much time spent on tasks that could be better handled by someone else—rather than focusing on revenue-generating activities!
Choosing the right remote staff provider is crucial.
It’s important to select a provider that operates ethically, promotes a strong community and culture, and prioritizes data security.
If you’re considering this route for your organization, it’s crucial to partner with a remote staffing provider that adheres to ethical standards and fosters a supportive and positive workplace environment. This ensures that you’re not only meeting your staffing needs but also contributing to a sustainable and responsible business ecosystem.
Make sure they have robust endpoint security, hold ISO certifications, and have reliable Business Continuity Plans. These measures ensure that your operations and data are securely managed, allowing you to focus on growing your business with confidence.
When hiring a Personal Assistant, it’s crucial to select a candidate who is proficient in a variety of key personal assistant job responsibilities.
The right person will have expertise in the following areas:
- Administrative tasks: These include handling administrative duties such as managing daily schedules, answering phone calls, and sometimes performing personal tasks, requiring strong time management and the ability to prioritize many tasks.
- Travel arrangements: Coordinating business trips by booking flights and accommodations, which demands previous experience in organizing and coordinating travel plans. This is an essential skill for any full-time assistant handling executive assistant duties.
- Calendar management: Scheduling meetings, appointments, and event planning without conflicts is a key administrative support task
- Email management: Sorting and responding to emails, organizing them effectively, and ensuring important communications are prioritized. Being the first point of contact for staff members and clients, handling sensitive information is a significant part of administrative work.
- Meeting coordination: Organizing meetings, setting agendas, and managing logistics to ensure productive outcomes is crucial for success. It requires strong communication skills and working closely with managers.
- Skills in various tools: A personal assistant role requires efficiency in tools like Microsoft Office 365, Google Workspace, Trello, Slack, and Zoom. Professional skills in these tools support a business’ rapid growth and help maintain work-life balance.
A virtual assistant job description may also include social media management, overseeing social media accounts, and data entry. Job titles in this field often highlight the importance of managing both personal life and business responsibilities, assisting with specific needs on behalf of one individual or multiple full-time employees. Research and preparing reports are also common tasks that help ensure overall success in this role.
A guide to interviewing Personal Assistance Chicago Specialists:
What to ask in a job interview
When interviewing potential Personal Assistants, it is crucial to clearly understand their technical skills and ability to handle important tasks.
Here are some questions to ask:
- Can you walk me through your background as a Personal Assistant?
- How do you prioritize and stay organized when tasked with multiple responsibilities, such as managing meetings, scheduling, and answering emails?
- What’s your experience with business administration tasks, like preparing reports or coordinating presentations?
- How do you handle sensitive tasks involving money or confidential information about the client’s personal life?
- Can you share how you handle planning and organizing events or presentations for a manager?

How much does hiring an outsourced virtual Personal Assistant for Chicago cost?
Hiring Personal Assistants can increase your productivity, but keep in mind that the costs vary widely depending on location and level of expertise.
When you hire Personal Assistants locally in Chicago, you’re looking at more than just their salaries. You have to consider additional costs like health insurance, retirement benefits, and office space, which can increase the total by about 30%.
Don’t forget about the expenses tied to advertising the position on platforms like Seek, Monster.com, and LinkedIn, or even the fees if you go through recruitment agencies like Hays, potentially increasing your initial costs by another 20%.
On the flip side, if you’re open to outsourcing internationally to places like the Philippines, Colombia, or India, you could see significant savings. The monthly outlay for an outsourced virtual Personal Assistant is often much lower than what you’d pay locally.
Tools like Cloudstaff’s Teambuilder can help you calculate those savings effectively.
By outsourcing, you can tap into a global talent pool without the hefty overhead costs that come with local hires. This is a smart move to keep your business agile and cost-effective.
Steps to hiring virtual Personal Assistants with Cloudstaff
Here’s how Cloudstaff simplifies hiring virtual Personal Assistants for Chicago.
Match
We use a database of 700,000 candidates and AI technology to find the right match for you.
Interview
We streamline the selection process to ensure you meet only the best candidates.
Offer
We handle all local employment paperwork, from offers to contracts.
Enable
On day one, your new hires have everything they need, including equipment and secure logins.
Induct
Our thorough legal induction ensures all new hires are compliant from the start.
Train
We provide access to training materials and to our learning platform, CS Academy, for ongoing talent development.
Manage
Our team supports productivity, staff relations, and growth, helping your workforce thrive.
Onboarding & training Virtual Assistants at Cloudstaff, your Employer of Record
When outsourcing Personal Assistants for your Chicago business, it’s essential to understand the staffing laws of your target countries. Companies like Cloudstaff, operating in the Philippines, Colombia, and India, handle compliance issues such as labor laws, payroll, taxes, and benefits, so you don’t have to.
It’s also important to find someone who fits both skill-wise and culturally.
We help you find virtual Personal Assistants proficient in English who align with Chicago’s work culture. We’ll guide you through assessing their technical skills and cultural fit with your company.
Cloudstaff ensures that the onboarding and training of your virtual Personal Assistants are smooth, helping them integrate effortlessly with your Chicago team. We start with clear expectations, provide comprehensive training, and nurture a supportive work environment.
Plus, our Client Growth Partners are always just a call away, ready to help and get your feedback, which is crucial both during the initial phase and as you continue to grow your team with us.
What makes Cloudstaff’s remote staffing solutions different from other outsourcing models?
We set ourselves apart in the bustling outsourcing scene with our unique approach to remote staffing.
Cloudstaff’s remote staffing solutions
Ethical outsourcing
- Committed to safety, employee growth, and a celebrated work culture
- Transparent pricing, and comprehensive benefits
- Robust Business Continuity Planning (BCP)
#1 Workplace
- Your trusted co-pilot to find the best talent
- Our recruitment experts offer access to over 700,000 skilled remote professionals worldwide, supported by our comprehensive Cloudstaff Academy
Operational brilliance
- Dedicated to your remarkable growth, our Client Growth Partners are always there for you whenever you need them
- We provide exceptional staff, mobilize teams, and manage performance to move your business forward
Enterprise-grade outsourcing
- Significant investment in advanced technology and platforms
- Unrivaled security features tailored for enterprise need
- Leading-edge in tech-enabled solutions with top-tier remote work technology and AI talent augmentation
- We have a Google-alum Chief AI Officer who is advancing our proprietary AI to enhance matching accuracy, ensure a private generative AI environment for secure staff usage, and develop specialized AI toolkits for various industries.
Other outsourcing models
Direct contracting
- Compliance issues due to legal concerns
Freelance hiring
- Tax obligations not met
- Lack of full-time commitment
Traditional outsourcing
- Ethical considerations
- Potential business risks
- Limited post-sales support
Establishing a local entity
- Initial investment requirement of approximately $250k
- Additional considerations for local equipment procurement
- Necessitates investment in local human resources and cultural integration
- Local bureaucratic hurdles

Keeping your remote Personal Assistants engaged goes beyond recognizing their skills
They need to feel valued. Foster a people-first culture with perks, recognition programs, professional development opportunities, engagement initiatives, and a focus on work-life balance to make a real difference.

Check out how you can save up to 70% vs traditional hiring costs with our TEAM BUILDER.

Download a custom remote staffing business case tailored to your hiring needs.
Having trouble hiring while watching your budget?
Let’s work together to find the perfect remote Personal Assistant.
