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You’ve Hired Your First Remote Assistant. Now What?

Learn how to ensure delegation success in this comprehensive guide for first-time remote employers.
In this post you will learn how to solve your recruiting challenges with remote hiring.
Congrats on hiring your very first remote assistant!‍We know that this can be an overwhelming time, especially if you've never worked with remote staff before.

In this guide, we'll walk you through six key steps that will help you ensure remote delegation success.

Let’s start from the beginning:

Starting Right

Many remote employers make the mistake of assigning tasks to their assistants on Day One. Now, we’re all for hitting the ground running, but this practice usually leads to a lot of confusion. Think: hours wasted communicating back and forth across timezones, your inbox flooded with access requests, and lots of questions from existing employees about the new hire.

You don’t want that kind of headache.

Instead of immediately assigning tasks, ease your remote employee into their new role with a thoughtful onboarding process.

What happens during onboarding?

An effective onboarding process involves:

  • Setting up your new assistant’s access to company tools and portals
  • Sharing key information like your SOPs and personal preferences document
  • Process training and orientation

Onboarding is also a great opportunity to give your assistant a virtual tour of your company. If you’re hiring an executive assistant, for example, you can introduce them to key team members and collaborators during the onboarding period.

Depending on the size of your company and the complexity of the role, the onboarding process can take a few hours to a couple of days to complete.

Bottomline: onboarding sets you — and the rest of your team — for remote delegation success. Don’t skip it.

Save our full guide on remote employee onboarding for later.

Build Trust, Foster Independence

Have you fallen into the Delegation Doom Cycle before? It’s when:

  • someone hires an assistant
  • they hesitate to give the assistant access or think it’s better if they do the task themselves
  • they fire the assistant
  • they end up overwhelmed with tasks
  • they want to hire an assistant…again

This vicious cycle prevents a lot of entrepreneurs from unlocking the true benefits of remote hiring. The good news is that you can easily avoid it by building trust with your remote employees.

How to build trust with remote assistants

We get it — entrusting your business to another person is a huge step. That’s why it’s vital to have a thorough screening and vetting process. When you’re assured that you’ve got a legitimate and reliable assistant, it’s easier to do these next steps:

  • Regular check-ins - Start by scheduling weekly 1:1 calls with your assistant. Get to know each other and build rapport.
  • Safely share access - Let’s be clear: sharing access doesn’t mean giving your remote assistant the keys to the kingdom on Day 1. Grant them only the necessary level of access to tools and accounts. For example, adding them as a delegate on Gmail allows them to manage your inbox without accessing your personal logins.
  • Foster an independent work culture - Give your assistants room to figure things out themselves. Instead of simply assigning them a task, share the importance of the assignment. Include your thought process when recording SOPs. Exercising agency gives them confidence and helps develop their problem-solving skills.

Related: How to find trustworthy remote assistants

Overcommunicate

"When you hire people internationally, you need to learn how to overcommunicate," shares Milkroad founder Shaan Puri.

Shaan explains that remote collaboration, while effective, is vastly different from working with people in the same office location. You’ll need to bridge the gap between different time zones, work cultures, and shared contexts.

Get your point across by overcommunicating.

Don’t assume your assistant knows everything. Instead, be super specific about things like:

  • project details
  • deadlines
  • deliverables —
  • — and expected outcomes.

🔥 HOT TIP

Ask your assistants to play your instructions back to you. Aside from ensuring that they understand your instructions, this method also helps you two build a habit of communicating clearly and specifically.

Related: How to improve communication with your remote team

Keep your remote team engaged

Like communication, remote team engagement also looks different from in-person engagement. You can’t just pop over to the breakroom for a casual chat, or invite team members for Friday Game Nights. Most — if not all — of your interactions with your team will be virtual, so make them count. Be intentional about keeping them connected despite the distance.

Simple ways to boost remote team engagement

  • Check-in genuinely. Ask them how their day is going. A little empathy goes a long way.
  • Create water cooler channels. Create a separate channel for non-work-related chats among your team members, like a channel for sharing pet photos.
  • Recognition - Reward high-performing team members with perks and recognition.

Engaged team members are happier, more productive, and less likely to churn. Set your business up for long-term growth by keeping your remote team engaged.

Read more: 9 Ways To Retain Remote Talent, According To Actual Employees

Keep their jobs simple

Maximize your remote team’s productivity by keeping their jobs simple. Sweaty Startup founder Nick Huber says it best:

“​​What happens when I try to get people to do 25 things well is that they ended up sucking at all 25 things.”

Nick shares a lesson he learned early in his self-storage business, where each employee was responsible for a bunch of tasks. Multitasking looked great on paper, but in reality, his employees struggled to check everything off their lists. They ended up doing mediocre jobs. Productivity plummeted — and Nick’s business almost followed suit.

Nick and his team were able to turn things around by simplifying the tasks of each employee. Instead of assigning a dozen disparate tasks, their employees are now focused on one or two key areas. When they needed someone to take ownership of a new task, they hired a new remote employee.

The takeaway: keep things simple from the get-go.

Related: How to track remote employee productivity

Create clear boundaries between life and work

Lastly, make sure you draw clear boundaries between life and work. It’s easier said than done, especially if you work from home. Especially if you love what you do.

But trust us, remote work is more productive — and more enjoyable — when it’s not burning you out.

Things you can do:

  • Set availability expectations- Don’t take meetings before 8 am? Have Wednesdays blocked off for brunch? Let your assistants know to set the right expectations.
  • Go async - Working asynchronously helps you cut back on unnecessary meetings. Use tools like Loom to record walkthroughs and SOPs.
  • Clock out from work - Create habits to bookend your work day. Physically step away from your workspace, or end each day with a workout. It may be a small step, but it helps you mentally separate “work time” from “home time”

Set yourself — and your team — up for delegation success

Hiring your first remote employee is a pivotal moment for your business. It can be overwhelming for first-timers, but if you get this right, you'll reap the benefits of global hiring for years to come.

Which of these tips will you implement first?

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