Hiring an Effective Manager to Run Your Online Business (Batman, Find Your Robin)

Elisa Doucette Updated on February 29, 2020

hiring a manager

Hiring an Effective Manager to Run Your Online Business (Batman, Find Your Robin)

Bruce Wayne is two things.

One: He is Batman.
Two: He is the wealthy and successful entrepreneur behind Wayne Enterprises, Inc.

Sure, he inherited a gazillion dollars and the family business when his parents were gunned down in a back alley, fueling a life of retribution-seeking and criminal-vengeance.

But there are plenty of people who squander the gifts they are given.

While many view Wayne as a lone operator, with only a few trusted companions to execute the day-to-day tasks of his business and life (looking at you Alfred and Lucius), even he eventually had to take on an apprentice to fight crime in Gotham.

Unfortunately, not all of us have an orphaned circus acrobat tumble into our paths when we are looking for someone to help us build our empires.

Which is why we’ve put together this start-to-hire guide on the process we’ve used to hire many of our apprentices and current employees — and how you can apply them to your online business as well.

How To Know You’re Ready to Hire A Manager

There are few mistakes more melancholy than hiring someone that you weren’t ready to hire.

Perhaps you read an article on some website that told you that you needed to hire someone to run your operations? Maybe your business coach suggested you outsource your major tasks? Or your team told you that you suck as a manager, but kick ass as a leader?

You should take some time to make sure you are really in need of a full-time manager for your business. If you are still starting up and growing, a virtual assistant or part-time independent contractor might be all you need for now. A big hire, like a business or operations manager, is going to end up causing more problems (fiscally and otherwise) than you originally thought.

Before you put up your big pie-in-the-sky job ad, there are a few things you should think about, to make sure you are still happy with the decision in three months. Acting as the hiring manager gives you a certain freedom to step back from the company and assess what it really needs.

Know Why You Are Doing This

Want to free up your time? Want to travel more? Want to focus on a different area of your business?

If you don’t have specific “other things” that you will be doing with the time that you are freeing up with this new hire, a couple things will happen. Either:

  • You’ll find yourself very bored, very quick, with nothing to else do (we know that sounds idyllic, but we bet you’ll be wanting to put your eye out within a month of navel-gazing)
  • You’ll never truly let go of the reins and allow your new hire to shine, because you have nothing else to do

This is also going to tell you a lot about the characteristics you’ll want in the person you hire (we’ll go into that in more detail below). The gaps you are looking to fill will take a special sorta someone, but if you don’t know what those gaps are, you won’t know who that someone is.

Not everyone will be able to make use of a recruiter or hiring manager to find the best candidates for them. Using this guide will help you to systemize the process of finding someone that’s the right fit for your business.

Red Flags To Look For in Your Day-to-Day

In addition to the existential “why” questions of entrepreneurial life, there are some very solid real-world examples of things that might be happening in your business that will require a big hire.

You Need to Focus More on Strategy & Growth

Stop us if you’ve said this before.

“I want to do XX (launch a new product, try a new marketing strategy, meet with more customers, do more public speaking to establish your authority in the industry, etc), but I just don’t have the time to dedicate to doing that AND running the business.”

Another solid red flag that is quite tangible is your to-do list. Primarily that you start with one every morning, and even though you work hard for 5-8-10 hours straight, you barely make a dent in what you set out to do in the first place.

Instead, you spend most of your time putting out fires and making sure things are getting done.

Which leads us to the next red flag…

There are More Mistakes and Fixes Than Actual Work Being Done

You are only one person. With only so many hours in a day and so many attention spans to devote to various processes.

Whether it is you causing the mistakes or you having to fix the mistakes your team of contractors and freelancers is making (or, if you are a good manager, having them fix the mistakes they made and learn from them) — if there are a lot of errors popping up on a regular basis, then that’s a sure sign that you need to bring someone in to do some serious oversight on your operations and processes.

The same way a factory has a quality control officer to make sure everything is done well and correct, you may need that in your business if too many things are slipping through the cracks.

You’re Overwhelmed

We’re not talking about that feeling you occasionally get, when you look at your to-do list and think there is no way you can ever accomplish it all and manage to make it to your kid’s soccer game by 3 pm.

We’re talking about that feeling you get every single day, when you look at your to-do list, want to crumple it up and curl into a ball in the corner of your room rocking and sobbing for all of humanity to hear.

You only have to get this feeling 3-4 times before you realize there is something very wrong in your business setup. It will probably take you at least another 5-7 times before you actually do something about it, but hey, not everyone makes it to Mensa.

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Get Your Business in Order Before Hiring Someone to Run It

Now that you know you need to hire a business manager, there are still a few things you need to do before you start the job posting and hiring process.

See, if you are hiring this person to come in and help fix your world, you need to make sure your world is at least vaguely in order. While it would be lovely to find one of those managers who can take your flaming hornet’s nest of an operational mess and make it the best business setup ever.

The reality of finding that person is…well…not a reasonable reality.

You need to make sure you have your shop in order before handing over the keys.

Make Sure You are Clear on Your Business Vision

Similar to how you have to know why you are hiring a business manager, you have to know what you are hiring them to do.

We’re not talking about the explicit details and tasks (we’ll get to that in a second) you’re going to assign this position, we’re talking about the nitty-gritty soul searching reason for your business.

Before you worry that we’re about to lecture you on your life purpose, and chastise you for not becoming Elon Musk yet, that’s not what this is about.

If your business vision is to change the world, kudos. If you are looking to make enough money to travel the world or pay for your kid’s education or keep yourself fully stocked with KitKat bars for the rest of time — you do you, boo.

But know what it is your business is working towards, so that you can make sure your business manager will help you work toward the same thing. This isn’t just a hire that is going to check items off a list. They need to buy into what you buy into, and help you build it.

Don’t Clear the Coffers

In online business, our coffers generally live in the world of Amazon and PayPal payment interfaces, but they are a very real ledger line on a healthy business plan.

We’ve seen a lot…we’re talking a LOT of business people who notice that everyone else is having extreme success hiring apprentices to come learn from them and help them build an empire. Bonus points if you can offer sweet perks like travel and trained personal chefs.

Here’s the thing though. You have to have the money and resources available to pay for the person without straining the rest of the business.

Cause the other thing we’ve seen happen (PS – seeing it happen once is more than it ever should have happened) is that people have high hopes and a good month or two of income, so they fly someone across the world to work with them. Then a Google update happens, their business tanks, and they’re like, “Oh hey, sorry. We can’t pay you anymore. So, that sucks.”

If you are spending every last expendable cent in your war chest for a hire like this, and expecting them to believe that you are a successful and savvy enough business owner for them to put their trust and devotion in, don’t. Just don’t.

Have Systems and Processes Already in Place

The truth is, you might need to hire an operations manager because your business is a mess.

But most of the time, you aren’t going to magically fix your messy business systems by hiring a manager.

Bruce Wayne didn’t just hand over the keys to the Batmobile and give Robin his own utility belt. There was a learning curve, and Batman already had a pretty efficient system in place that Robin could plug and play into.

You will find a much smoother transition, and better results from your business manager if you have systems and processes in place for the team to execute on their daily tasks. If you aren’t sure how to set those up or get them documented, this post on giving your team members the keys they need to grow your kingdom should help.

In fact, the best business managers excel at managing team members or independent contractors who are already capable of working on their own. They can focus on making changes that take the business forward, rather than fixing the disaster that a business is currently.

Clearly Defined Job Role

The final thing you’ll want to lock up before you get started with the job posting and hiring process is figuring out exactly what it is you want this new manager to do.

Aside from “All the Things!!”, you should have a carefully delegated list of tasks and general activities that you are going to put your new manager in charge of.

Don’t be afraid to aim high here. Similar to dressing for the job you want, rather than the job you have, you want to hire the manager they will eventually be, not just the manager who will need to start at the beginning of the learning curve.

batman job

In addition to task-based responsibilities, like:

…you will also want to let them know that this isn’t a position that you simply expect them to show up and check boxes for. Let them know that there is a lot of flexibility for the position to change as they find their own stride and that they should bring their own suggestions to make the job their own.

What To Look For in a Manager

Of course, beyond just figuring out what you want your new manager to do, you’ll want to make sure you are hiring someone who is going to be right for the position — and your company.

Personality Fit

This is going to be someone who is working with and communicating with you a lot. We’re talking at least a few times a week, if not daily. Make sure you’re excited about that. Sometimes it doesn’t have to be a bad fit to not be a good fit.

Also consider, how will they fit with the rest of the team and company culture? Are you a mostly laid-back, very freestyle organization? Perhaps someone who wants to institute strict corporate policies isn’t going to be a good match. Or if you have a very carefully documented list of processes and tasks to be done, but the candidate “likes to fly more by the seat of their pants”, then send them off into the wind.

It might seem like they’ll be a great balance to your style if they are the exact opposite of you, but we guarantee, too different in all the wrong ways will be too much of a problem.

Track Record

Well, this one is kind of obvious, but we’re gonna touch on it anyway.

If you are going to hire someone to run your business, they better have a proven track record of successfully doing similar things in the past. That doesn’t necessarily mean they have to have run their own business, or have built other empires (though wouldn’t that be a sweet hire!), but they do have to have the background. Even a diamond in the rough will have spots that shine brighter than the untarnished portions.

The same way you wouldn’t buy a site that has no solid background and results, you shouldn’t put your future in the hands of someone who can’t prove they can back up their claims of greatness.


We’re not talking about their background and expertise, that’s pretty well covered in vetting their track record.

Instead, we recommend you make a “Dream List” of the skills you want your perfect candidate to have. Things like leadership skills and communication skills are usually must-haves for a decision-maker role. Look back at your earlier brainstorming and soul-searching — are there red flags that could be solved with a particular skill set? Do you need help with the systems and processes you have in place? Figure out what you need in your business, and then figure out what skills will help with that need.

Of course, the chances you’ll find a candidate who perfectly fits and matches what you are looking for in a “perfect candidate” are probably pretty slim.

So make this list with the intention that it is likely never going to manifest fully. But if you can figure out, before you even begin to put together the job ad and start the interview process, exactly what you want, you’ll be elated when you find someone who fits 70-80% of the bill.

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How to Hire a Manager

Whew! We’re about 60% into the process at this point.

It seems a bit counterintuitive, but similar to so many other important relationships, you’ve got to make sure you are 100% squared and ready to bring someone like a business manager in.

Otherwise, you are expecting them to fix everything and make you whole — but as Shel Silverstein taught us, in love and life, you can never expect someone else to be your missing piece.

You’ll spend a lot of time working on these beginning steps before the process of applications and interviews and hiring. To be honest, you’ll be surprised how much more time you spend on these parts than the actual process of applications and interviews and hiring.

As a quick recap, here’s what you’ve done so far:

  • You Know You Have to Hire a Manager
    • You have reasons why your attentions need to be focused elsewhere
    • You’ve identified serious red flags in your day-to-day that need to be addressed
  • You Have Your Business in Order
    • You are clear on your business’ vision
    • You won’t bankrupt your company with this hire
    • You have systems and processes in place that can be improved on
  • You Know What To Look For
    • You know what personality type(s) will be a good fit (we’re not talking Myers-Briggs, unless you’re big on that, in which case quiz away!)
    • You know what kind of background and track record you expect from an ideal candidate
    • You have the basics of a job posting, that includes a “dream list” of the skills you are looking for (but you are willing to accept that you may need to hire someone who fulfills only 70-80% of them)

We’re now at the “writing up the rest of your job posting and putting it out to the world” portion.

The Rest of the Job Posting

Most entrepreneurs, when they are putting together a job description for a big position (or any position, really) consider only what they are looking for in a candidate.

But if you want to get a quality candidate, someone who will dig in and help you grow your business, you have to also consider what they might be looking for in a company.

Quality candidates that are searching for jobs like this are going to be looking for a place where they can not only add to the company, but will be happy to do so and excited to work with you. You need to sell them on your company and position as much as they need to sell you on their personality and abilities.

Here are some things we’ve found, in our postings, that added to our field of interest:

Consider benefits and perks that might be worth more than money to someone

Here at Empire Flippers, Joe and Justin live a “location independent lifestyle”, meaning anywhere they have wifi and their laptops, they can work. This doesn’t mean they flit around the planet working just four hours a week (you’d likely be surprised how much they work, actually).

But they aren’t going to say that they can work hard, and be leaders of the company, and not offer the same set up to their team members. Hypocritical much?

Sure, there are times when you may need to be in one place (most of the Empire Flippers apprenticeship and team member jobs start with 90-180 days in one location, working closely with a senior member of the EF team, or Joe and Justin themselves) — but after that, you are free to live and work wherever you want, as long as you are able to get your work done.

It doesn’t have to be a global office to be a benefit or perk that might matter to someone. Consider some of the more traditional structures and policies you are willing to be flexible on (look back on your business vision if you’re struggling to figure out what sets you apart) and make sure to sell those points in the posting.

Have them include a video

Want to know how someone is in person? Ask them to include footage of themselves, “in person”.

But don’t base your hiring decision totally on this. In today’s Snapchat and Facebook Live world, people are becoming more and more proficient at putting up a cultivated personality for the internet.

The right person will likely not be perfectly polished. If they are perfectly polished, ask them how they got to be so good.

Use easter eggs and specific asks

Nope, we’re not talking about those delicious chocolate treats that come around every spring in stores and candy shops.

Easter eggs are random, sometimes seemingly non sequitur, requests that you ask your candidate. Specific asks are detailed instructions on a particular piece of background vetting you are looking for.

Things like “Start your application with Orange Sky” or “Send four links to blog posts or articles you have pitched successfully to outside websites and media outlets” to see who is paying close attention to your requirements and requests.

Like your “Dream List”, an ideal candidate might miss one of these but be exceptional in every other way possible. We have yet to see that happen.

Eliminate tire kickers

You have a cool online business. You’re successful. You allow people to work where they want, when they want, and are interested only in making great things happen.

There are a lot of people who want to sign onto an opportunity like that.

So you need to make it very obvious to them some of the “not-so-great” things about this gig. We do this by flat out listing the things that we know are not fun about these positions. In our most recent hiring post for an Account Manager in Saigon, we included an entire section: “Love It, Now What’s the Catch” — where we outlined the sometimes weird hours, the high-pressure expectations and demands of an account manager, and the starting pay.

Make a probationary period clear

Online business, location independence, analytics report review for seven hours starting at 11 pm — what isn’t fun and sexy about this work?

Lots of people will apply and seem like the most exceptional candidate, but once they start in, it will quickly become apparent that this is not going to work. There’s a saying in business, be slow to hire and quick to fire. With a probationary period, there’s no harsh firing chants by a tiny-fisted orange reality television star.

Rather than dragging it out, making it excruciating for you and for them, be clear from the beginning that you are both going to be testing each other out. And either party is free to walk away, no hard feelings, for the first 90-180 days (depending on what works for you).

You want people who are willing to accept that while they look for their dream gig, they will often have to find something that is going to hit only 70-80% of their list. And they need to be ok with that. You aren’t a charity, it isn’t your job to take on every person who wishes for something more, and thinks they might get it working with you.

Where To Post Your Job Ad

If you have a non-traditional business structure, like most online businesses tend to be, especially in their starting phases, you are going to want to hire through the non-traditional routes.

Newspapers and corporate job boards might bring a certain string of candidates, and are probably what more people are familiar with. But that probably won’t work for you.

Write a post or create a page

The same way you’d sell a product or service online, if you are selling an extremely vital hiring opportunity, you want to SELL THAT SHIT.

We write a new job posting for every big open position we want to fill in Empire Flippers. Since we’ve written a number of sales pages in our day, we write the job posting very similar. It’s a trick we picked up from our friends over at Tropical MBA. You can see some of the prior postings among our other hiring and outsourcing articles here.

It gives you a place to direct inquiries and referrals, because the #1 place to find exceptional business managers is…

Hit your network first

Getting a recommendation from someone you know is almost always better than hiring cold.

Or hire someone from your audience and customers, who you know is already a devoted fan. Devoted fans make for great devoted team members.

Try posting your newly created job post or page to your professional and personal social media, especially Twitter and Linkedin. Share it in any online communities you are a part of. Email it to trusted colleagues who might know someone that would be a good fit (use this one sparingly — if you are in super expansion mode, hitting 50 of your closest entrepreneurial friends with every hiring post is gonna get old fast.

Find non-traditional job sites and communities

Aside from the popular choices like oDesk and Craigslist, for finding independent contractors and non-traditional workers, you can also try out some of these up-and-coming contenders.

Escape the City – A job posting board with “hundreds of job opportunities from forward thinking and progressive employers.”

Get Apprenticeship – Taylor Pearson literally wrote the book on the changing scene of jobs (his book, The End of Jobs, was a breakout best-seller last summer) and now runs a curated email list that he will send vetted apprenticeship opportunities

Location Rebel – Longtime Empire Flippers friend Sean Ogle runs an online community specifically for people looking to break out of their cubicle and create a life that allows them to travel the world. It’s a prime spot for finding someone who wants a better life, and is willing to work to get it.

With a job offer like this, in places like these, the applications are likely to come flooding in. So now we’re on to the main event…

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Application Pare-Down, Interviewing Techniques, and Hiring Ideas

You’re sitting on a mound of applications and videos, and you don’t know where to begin.

You don’t have to talk to EVERYONE, do you?

Of course you don’t. You’re going to spend your time now finding the BEST person from all the people interested.

How does one do that?

Have rounds internally to pare down the general pool of applicants

You are going to sift through this list multiple times. You’ll probably watch certain applicant videos three or four times, 20-30 if you include all the viewings from everyone on your team.

In fact, make sure to include key members of your team. If they are going to be working with this person closely and often, they should be part of choosing who that person will be. Often, you can ask them to take some of the earlier rounds, and they’ll quickly be able to identify tire kickers and unqualified managerial candidates.

Test Them

If there are specific tasks they will have to do exceptionally well, and with little supervision, have them do a “test” in the final rounds of the interview.

Using Google Forms or Typeform or a similar platform, you can put together a quick 7-10 question “test” that will ask applicants questions or to complete certain quick tasks.

Don’t take advantage though. Asking someone to do an hour-long project for a job you are only kinda considering them for is a jerk move.

Don’t do phone interviews with more than 3-5 candidates

Have a list of interview questions pre-prepared so you can ask the same questions to help you compare the candidates.

We once heard of an entrepreneur who did 17 phone interviews with candidates.

Shockingly, it was really difficult for him to make a decision on who was the best.

Use a matrix to quantify skills and values

With all this talk of skills and personality and touchy-feely soft subjects, it can be difficult to quantify a candidate’s ranking among other applications.

Remember that Dream List you put together? Everything you want in a candidate?

Well, open a Google Spreadsheet, and list those things (or, general categories that embody those things) along the top. List the top candidates in Column A along the side.

On a scale of 1-10, rate each candidate on the skills, categoric background, and personality fit you are looking for.

Then, add up the ratings. Magically, you now can rank your candidates based on what you felt was their overall impression. And dig down into whether there is a weighting to various categories — meaning how they work with others matters to you more than how well they know their way around Longtail Pro.

Also, be ok with emailing for more information and clarification. Press them on their information and answers. Goodness knows you’ll be talking enough in the following months and years.

If they can’t deal with some hard follow up and challenges, they aren’t going to be able to handle what is to come.

Ready To Hire Your First Manager?

This was a long article, and with good reason.

Hiring someone to take over essential roles and responsibilities is not something you should take lightly.

You want to find someone who is going to be with you for at least a couple years. They are going to want to dig in, and help you grow your company to new levels of success you had previously only dreamed about.

You want to free up your time, for personal or professional reasons (often both), and feel happy walking away from certain parts. Without worrying if everything will fall to shambles if you aren’t around.

It is hard work, finding someone who will make your work easier.

But most of us aren’t in this game because we thought it would be easy.

Put in the effort, find the best person, and see what happens. Once you get this process down, it becomes possible to scale it up to create an entire management team.

It’s certainly worked well for Empire Flippers.

Have you hired a business manager successfully? UNsuccessfully? What would you add here?

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