The Ultimate Guide to Hiring an Offshore Assistant

Side Hustla:

You need an assistant. Even if you have a W2. 

Someone to triage your emails, take the little stuff off your hands, keep your time free for the big stuff. Someone to research travel arrangements and organize your messages on 4 different platforms.

But you have no idea how to find that person.

Consider this your Ultimate Guide To Hiring Offshore Talent.

This method works for just about any kind of offshore hire, with nuance of course, but we'll focus on hiring someone that will report directly to you and unburden your day.

Also, I have a ton of friends who have staffing services. I have not used them but if this whole process looks arduous, just get someone to hire for you. It will cost ~$3,000 but will save you a lot of time. Hang out on SMB Twitter for about a day and you’ll find at least 5 people that have staffing agencies - no joke.

This is for the DIY crowd.

Ready? Go:

1.  Write down WHAT you want them to do. This is where most people drop the ball. They literally write down "executive assistant" like everybody should know what that means.  

Don't half-ass this.  Take a week or two to fill in a task list that you need someone to do.  Things like:

• anything redundant or repeatable

• anything that doesn't really move the needle for revenue or profit

• email/instant messaging/phone triage - I'll show you how to manage this

• bookkeeping, coding credit card statements, invoicing

The more thought you put into this, the easier the entire process will be. As you do this, you'll accumulate various skills needed (excel, Quickbooks, Zoom, video editing etc.)

2. Write down HOW you want to work with them.  This is not the what, this is the when, where, how.  What hours do you expect them to be available?  What meetings must they attend and when are they?  How do you like to communicate, all day chat or once a day update?  (hint: in the beginning you're probably going to need to be available nearly all day or it will take forever to get them up to speed, plan accordingly)

3. Choose your region. Here's where I get myself into trouble. I'm going to make some broad generalizations about cultural and geographical fit. Deal with it. This is just from my experience:

• Philippines: these folks are just inherently nice. They aim to please, so customer service and EA work is a natural fit. The problem: their time zone. They're roughly 12-15 hours ahead of the US. If you need them during US working hours they'll be working the night shift, which (IMO) is not sustainable for working parents. They'll do it, of course, but it's really hard to maintain it for years. Their English is GREAT, and often have almost no accent. 

• South Asia (India, Pakistan, etc): these folks are so diverse you can find anyone to do anything, but I've found their proficiency with technology to be the most useful. Fixing websites, integrating software, writing code, etc. are easy for them.  They too are geographically challenged so I prefer them for tasks that can be done without my watchful eye.  English is generally good but they tend to be heavily accented.

• Eastern Europe: These folks are highly technical proficient. We do have a writer and graphic designer from this region too. Tend to have heavy accents. They tend to be gruff and very direct though, I wouldn’t hire here for positions that require a soft touch.

• Latin America: This region is just now emerging as a great option. They have a wide breadth of abilities, but we'e used them mostly for customer service and writing so far. English is good, slight accent. Their one massive advantage is time zone. They are right at or near the US timezones. This is huge for real-time communication, meetings etc. 

If this is your first remote hire and you need an assistant, I would go for Latin America or the Philippines. 

4. Choose your platform: Upwork is the easiest because you can target anywhere in the world. But if you're attached to the Philippines go to http://www.onlinejobs.ph/, or https://www.remoteco.com/ for Latin America.  

Notes: 

• Generally, you can pay $600-$800/month to start. Some high quality candidates will want $1000+. You will often pay a "13th month" at the beginning of December...so know you'll pay 10% more than you think. Still it's minimal.

• I pay them weekly with Wise. I have it set up to autopay them.

• I make videos to convey tasks, then have them save the videos in Google Drive or a wiki so they can reference later (and have them organize, categorize the videos/training).

• Note that, culturally, they are often anti-confrontational, so if they screw up, give them praise, then tell them what they did wrong, then more praise. If you're too harsh, sometimes they just "disappear." Most of them are not used to Americans’ directness. Use a lighter touch and then move mountains for you.

5.  The application process. I have an example job posting for a customer service rep right here.

Feel free to copy and adjust as needed. But you'll put your job description with one big addition. DO NOT SKIP THIS STEP. Near the end of your job description, but not at the end, insert this or something like it:

• All job applications must start with the word 'unicorn'. Your job application will not be reviewed if you do not include this word as the very first word on your job application. 

This is a filter for attention to detail. So many applicants will scan your job description and cut and paste an application.  You need people who were so interested in the job that they reviewed the entire description. Having them write your trigger word first makes it easy to review your job board since the inbox will show you the first few sentences of the messages. You'll simply archive any application that doesn't start with that word. Boom - 75-80% of your job applicants are gone without a single interview. 

6. Narrowing them down.

Then you'll review the remaining and nuke anyone that doesn't seem like a fit. It might be poor English or no experience. For the remainder, you can use our 2nd step which is under the "Next Steps" header again on this page. It involves writing, creating and video, and answering some questions.

This part does several things: 

• eliminates another 10-15 of applicants too lazy to jump through your hoops

• the video that they will let you know a ton about their work environment, their internet speed, their English and their general demeanor.

From here we try to get people who GWC:

• Gets it: understands what you want, what you're looking for 

• Wants it: you can't coach enthusiasm, you want people who are excited to work for you

• Capable of it: they have to to able to do the darn work - for this we often set up a few test projects (and we pay them for these)

And - most importantly - you have to like them!  You don't want a highly capable a-hole. If you naturally smile when you see them message you, its a good sign. 

7. Hire them. You'll have to figure out payments etc, and cadence for meeting, and then its time to get to work. Tell them you'll give them 4-8 weeks as a test.  Then its best to train using Loom and training videos. Be prepared to do some hand-holding in the beginning. Stay patient. This person is literally going to be your right hand if you do this right. It's best of they kind of shadow you, in close contact throughout the day. 

Begin by unloading your email inbox. Anything autogenerated (invoices, orders, etc.) get that stuff out of your inbox but have your assistant do a daily report or similar so you know how orders are going. Set up automatic filters.  Stop doing data entry for God's sake! Forward messages from your various platforms and coach them how to respond. Of course have them explain their roles to the reciever.

Introduce them to your team, your big vendors and clients, and tell them your EA may be responding in the future. Get any bookkeeping off your shoulders right away, but have your accountant review to make sure they're doing it right.

NEVER let go of the checkbook or bill paying authority, but things like QB online and Bill.com will allow your assistant to set up the payee and the bill and you simply go in and approve payments. 

Remember: the most effective leaders have a relentless focus on high leverage tasks. 

ANYTHING THAT IS NOT HIGH LEVERAGE (DRIVING REVENUE, PROFIT, BRINGING IN MORE CUSTOMERS, GETTING YOUR EXISTING CUSTOMERS TO SPEND MORE OR MORE OFTEN) COMES OFF YOUR PLATE NOW. JUST DO IT.

Focus on the important stuff, your assistant is there now for everything else. It will take time but after about 2 weeks you’ll say, “I should have done this 3 years ago”. Eventually you’ll find you have need for another person. Guess what: you can have your first assistant hire the second one. We hire 3-4 people a year and only talk to them once they are on board. It’s great.

Yes, of course this process is going to be painful as you train someone, but if you wait it's only going to get worse. Do. It. Now.

Questions? Just hit reply and fire away…

Kriss Berg

PS: if this was useful for you please send out a Tweet about it and tag me @KrissBergTweets, or reply to this with your thoughts. Appreciate ya…