entrepreneur thinks about the best way to hire an assistant

The Best Way to Hire an Executive Assistant: Outsource it.

Ryan Cassin

Ryan Cassin

entrepreneur thinks about the best way to hire an assistant

What’s the best way to hire an Executive Assistant?  Don’t.

Often, the best approach is to outsource the hiring process altogether.

Hiring an Executive Assistant is a crucial step in an entrepreneur’s business growth strategy.

Yet, the hiring process is time-consuming and expensive.  What’s more, hiring an Executive assistant isn’t something you do every day, so you may feel you lack the knowledge and resources to make the most of this important hire.

Fortunately, an Executive Assistant service like Superpowers can help you hire an Executive Assistant.  With Superpowers Match, we handle everything for you.

We find your ideal Executive Assistant, train them, and ensure their success through our specialized Curriculum, Coaching, and Community.

The Time and Money Problem 


Onboarding an Executive Assistant is a costly process, both in direct expenses and in time dedicated to training.

On average, the cost of onboarding a new employee is $3,000, according to SHRM‘s Human Capital Benchmarking Report.  For you, a business owner, the opportunity cost may be even higher.

What high-value tasks could you be completing in the time you dedicate to training your new Executive Assistant? What deals could you have closed? Clients you could have landed?

We provide the easy button! Instead of devoting significant time and money to finding and training your Executive Assistant, we handle it for you.

We use our proven hiring process to connect you with an Executive Assistant that uniquely fits your values, work style, and needs.

Your Executive Assistant undergoes rigorous screening and training, and we take them onto our payroll, saving you the paperwork.

Your job on day one? Enjoy the benefits and get things done!


The Training Problem 


Setting aside the cost of training when you hire an Executive Assistant, do you have the infrastructure in place to provide the top-tier training your Executive Assistant needs?

SHRM also reports on the value of high-quality onboarding training programs.  SHRM references a Wynhurst Group report that found employees were 58 percent more likely to stay with the company past three years if they received a structured onboarding process.

Within the same article, we learn the Aberdeen Group found that 62 percent of organizations with onboarding programs report experiencing higher levels of efficiency in their employees.

The easiest way to maximize your chances of having a high-performing, long-term Executive Assistant?  Provide them with a strong onboarding process and valuable continuing education resources. 

Training Executive Assistants is our expertise.  We pride ourselves on training and supporting the industry’s top-performing Executive Assistants.  After we hire an Executive Assistant, we provide:

Superpowers University – A three-day training intensive covering essential technical and soft skills for Executive Assistants.  This occurs before they arrive for their first day with you.

Continuing education resources – Training resources for continued growth after Superpowers University.  These cover many of the soft skills required to excel as an Executive Assistant, including stress management, entrepreneur-assistant communication, and representing their entrepreneur.

Proven Playbooks – A growing library of practical guides to help your Executive Assistant seamlessly manage your daily business activities.

Masterclasses – How-to videos presented by fellow Executive Assistants.

Quarterly learning events – Learning events with leaders in the entrepreneurial community.

Monthly Focuses – Each month, your Executive Assistant selects and completes a training module on a specific high-value skill.


The Support Problem


When considering the best way to hire an Executive Assistant, consider your long-term support structure.

Executive Assistants occupy a unique place in a company’s organizational structure.  They rarely have direct colleagues with whom they can share their challenges, questions, and ideas.

Even after you’ve hired an Executive Assistant, you and your team may sometimes feel underequipped to help your Executive Assistant navigate assistant-specific challenges.

Who can help? Other experienced Executive Assistants!

In our Superpowers Community, Executive Assistants are equipped, challenged, and encouraged through:

Monthly cohort meetings – Structured peer-to-peer discussions designed for continued growth, accountability, and encouragement.

Slack community – A space for sharing ideas, best practices, and problem-solving techniques among top-performing Executive Assistants.

Coaching – One-on-one calls with our veteran coaches designed for equipping your Executive Assistant for success.



Typically, you only hire an Executive Assistant every 5 to 10 years.  If it’s not something you do every day, it’s hard to know how to best approach this important hire.

The process of hiring an Executive Assistant can be time-consuming and costly – so it’s important to get it right the first time around. 

Once you’ve made the hire, do you have a ready-made onboarding and continuing education strategy in place?

So, what’s the best way to hire an Executive Assistant?  We hope this helped you get closer to your answer.

We’re happy to help make the process of hiring an Executive assistant easier!  Interested in learning more about finding and hiring your ideal Executive Assistant? Book a discovery call today!

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