Before You Hire an Assistant, Consider These Questions

Picture of Ryan Cassin

Ryan Cassin

When you hire an assistant, there are a lot of complications to consider.  We’ve put together a quick guide here:

Selecting the Right Staffing Service:


1. Do you want a virtual assistant or a virtual Executive Assistant?

Most remote assistants on sites like Upwork and Fiverr are virtual assistants. There are some specialist companies like Superpowers that provide virtual Executive Assistants.

Standard virtual assistants check off a to-do list and call it a day; they are great for maintaining your company and completing simple, routine tasks.

A virtual Executive Assistant tackles your to-do list and then looks around for “what’s next.”  They are fully dedicated to your business and take a proactive role in getting things done, even before you ask.  Here’s a detailed look into virtual Executive Assistants.

Virtual assistant: Can handle routine, simple tasks you provide them.

Virtual Executive Assistant: Works as your proactive partner, coordinating your schedule, team, and business.


2. What is the hiring and onboarding process?

Onboarding an assistant is a costly process, both in direct expenses and in time dedicated to training. Consider finding a staffing solutions company that handles the entire process for you.

We provide the easy button! Instead of devoting significant time and money to finding and training your assistant, let us 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.


3. What support does the staffing service provide? 

Assistants occupy a unique space in a company’s structure, and they rarely have counterparts with whom they can connect about their ideas and challenges.

You likely don’t have the time to provide specialized and dedicated help to ensure your assistant’s success.  Consider the support systems provided by the staffing solutions company you are considering.

At Superpowers, we personally ensure your assistant’s success. Superpowers 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 to equip your Executive Assistant for success.

Training Resources – Our training intensives, masterclasses, continuing education resources, playbooks, and learning events for equipping your assistant to exceed your expectations.


Selecting the Right Assistant:


How do you determine if a virtual assistant is an ideal assistant for you and your business?

Here are a few thoughts:


1. They have the practical skills to do the job

Try this step-by-step approach:

  1. Identify why you are hiring an assistant. What are your big-picture goals?
  2. Identify what tasks and duties your assistant will need to fulfill to reach your goals.
  3. Consider what skill sets and knowledge your assistant needs to have to complete those tasks
  4. Request information on the assistant’s training and skills. Are you confident they can do the job.

To get an idea of what you need from an assistant, create a list of all the tasks that you do.  As you go throughout your week, write down the different tasks that take up your time.

Then process the tasks:

1. Eliminate Tasks:

  • Before you spend time delegating a task, consider eliminating it altogether.  Think a task is unnecessary?  Try temporarily eliminating it and monitor the impact.

2. Delegate Tasks:

  • Identify the tasks you don’t enjoy.
  • Identify the tasks that are outside of your skill set.
  • Identify the tasks that aren’t worth your time.

Once you have this list, your assistant can either personally handle these tasks or orchestrate the delegation of these tasks to others.


2. Their communication style syncs with yours

Like any relationship, everything works better if you “get each other.” Having communication styles that work well together is a time-saver for productivity. Effective communication facilitates growth.

Numerous reputable assessments help you avoid time-consuming trial and error.


We use the Predictive Index Behavorial Assessment when making pairings for our clients. This specific test assesses the working and communication traits of test-takers and provides information about their compatibility with others and allows us to predict compatibility with improved ease and accuracy.


3. Their attitude aligns with your vision

You want an assistant with a committed, resilient and positive attitude towards you and your business. They get behind your vision and are ready for anything that might come their way. Such a virtual assistant is a likely good fit for you.

Design your interview process to determine how well your potential assistant fulfills this standard. At Superpowers, we conduct rigorous interviews with potential assistants to assess these qualities.

Consider questions that identify adaptability, temperament, collaboration, initiative, and growth potential.


Here are just a few helpful questions we have found useful:

  •  Tell me about a time when you were asked to do something you had never done before?
  • What’s the most interesting thing about you that’s not on your resume?
  • What was the last collaborative project you completed? What was easy and challenging about this project?

We’ve Designed the Easy Button


Our founders, Ryan and Steven are serial entrepreneurs. They founded Superpowers in response to a need they and their fellow entrepreneurs were feeling:

“I know a high-performing assistant would help me and my business, but I don’t have the time and energy to invest in finding one.”

Ryan and Steven set to work identifying the essential qualities of a strong assistant-entrepreneur relationship and then developed a system for creating those ideal matches between assistants and entrepreneurs.

Seeing an opportunity, they turned it into Superpowers!

How it works: 

  1. Learn your needs: We sit down with you to identify your specific needs, wants, goals, and values.
  2. Learn about you: We have you work through a few short, but reputable and comprehensive assessments like a Predictive Index test.  These help us understand your personality and work style.
  3. Find your assistant: Equipped with our knowledge of your needs, we filter through thousands of applicants to find your ideal partner.
  4. Get your approval: We bring them to you for an initial meeting and approval.
  5. Handle onboarding: We bring them onto our payroll and handle the entire onboarding process – you don’t need to do a thing.  You just send us a payment each month.
  6. Upfront training: Before their day one with you, we equip take them through a week of rigorous training.
  7. Continued support: We continue to provide unrivaled support through our unique-to-industry Curriculum, Coaching, and Community.


There are a lot of questions to consider when hiring your assistant – these questions are our specialty. If you’d like to discuss finding your right-fit assistant, book a Discovery Call.  We’ll sort out the process with you – let’s determine what kind of virtual assistant is a good fit for you.

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