The Ultimate Playbook for Hiring and Managing a Remote Executive Assistant - Outsource Access

The Ultimate Playbook for Hiring and Managing a Remote Executive Assistant

If you’re someone who’s tired of being tired, then strategic support from a remote executive assistant might be for you. When you’re running a business, then odds are you are constantly on your feet, fixing problems, attending meetings, answering emails, juggling deadlines, and trying to keep a dozen spinning plates from crashing.

But its time to make that (exhausting) scenario a thing of the past.

The right remote executive assistant (EA) can become your right hand – streamlining operations, managing your calendar, handling communications, and freeing up your time for what really matters: growth, innovation, and of course, a well-deserved lunch break.

Today, we’re sharing you a playbook that shows you a step-by-step guide to not just hiring a remote executive assistant, but doing it the right way. Want to reclaim your schedule and make time work for you? Let’s get started

Step 1: Define what you really need

Always start with defining your needs. For one week, try tracking every task that you do. Highlight the ones that could be delegated, such as admin work, scheduling, email triage, document prep, travel planning etc. The test is, if you’re doing it but someone else could – put it on the list. 

Try asking yourself these questions:

  • Do I need help mostly with business or personal tasks?
  • What platforms or tools do they need to know?
  • What time zone or availability works best for me?

The more sure you are of your goals, the easier it is to achieve them.

Step 2: Hire smart, not fast

When you put out a job posting and get a flood of resumes, who do you know which to pick? Sometimes, you can get overwhelmed with the applicants, so instead you can:

  • Use a vetted outsourcing service or recruitment platform that specializes in executive assistants
  • Give equal weight to interpersonal strengths and technical expertise. Communication, creativity and discretion are non-negotiables.
  • Don’t skip the trial tasks –  give candidates a real assignment to see how they think, solve problems, and communicate.

Here’s a bonus tip: Hire for personality and productivity. Since this is someone you’ll be working closely with, it has to be a good match professionally and personally.

Step 3: Build a Bulletproof Onboarding Plan

The first 30 days is the most crucial part of the relationship – its the stage when you find out if the executive assistant is a really good fit for you. That’s why laying a strong foundation from the start is essential by:

  • Sharing your preferred tools, platforms, and processes
  • Giving access to a clear SOP or video walkthrough for recurring tasks
  • Scheduling regular check-ins (daily at first to help settle in, and then you can transition to weekly)

Remember: a great remote EA isn’t a mind reader, but with the right onboarding, they won’t have to be.

Step 4: Communicate, communicate, communicate

Communication is the key to success. It clears up misunderstandings and provides clarity, which is everything when working remotely. You can use tools like

  • Slack – for real time updates
  • Trello or Asana –  for task tracking
  • Loom – for explaining complex tasks via quick screen recordings

Set expectations around availability, response times, and feedback loops. Clear, consistent communication is the key to building a powerful working relationship.

Step 5: Grow Together

As your EA gets into the groove, they’ll start to anticipate your needs. Encourage them to own their tasks, and time, you’ll have a match made in heaven. This is not just about delegation – its about collaboration. 

When you’re paired with the right executive assistant, you open up opportunities you never thought possible. Unlock possibilities with a remote executive assistant – use this playbook to find your match today.

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