The Millionaire Action Guide To Hiring: Hiring Like A Millionaire


One of the very first obstacles that aspiring six- and seven- figure business owners encounter is hiring and growing their team. It’s understandable. After all, your business is your baby — and entrepreneurs are notorious control freaks!

We like to do it all ourselves. We’re moving fast, we want to stay “lean,” and we often feel that it’s easier to just do it all ourselves?

Until it isn’t.

At a certain point, to grow you’re going to need to bring on team members. But slowing down long enough to tease apart the hiring process and figure out who you need to hire, for what position, where to find them, and how to select the right person for the right job can be overwhelming. You’ve got clients and customers to serve, products to perfect, and sales to make.

So typically, what I see my clients do is avoid the whole thing.

They figure they’ll just limp along as they are. If you have a team of two, five, or even ten great hires, you just keep piling on the work — even if it’s outside their field of expertise, or the workdays are getting longer and longer. The team will all just work harder, work longer, and “work smarter.”

It’s almost like you think one day you’ll wake up and the business stork will have deposited your new employees on your doorstep in a wicker basket, complete with laptops and stellar references!

I don’t need to tell you that it doesn’t work quite like that.

And then when the dream employee doesn’t just ring the doorbell, people put off hiring until it’s just so painful and they’re so desperate and they hire the first person with a pulse who applies.

And I’m also sure I don’t need to tell you that method isn’t too effective, either.

The biggest difference I see between the millionaires I interview and the business owners I coach when it comes to hiring is that millionaires don’t hesitate. And they don’t hire on a whim, either. All of them — and I’ve interviewed hundreds — have processes for defining the position, soliciting applications, evaluating applicants, and then onboarding them once they’ve found a winner.

Imagine that — having a PROCESS that kicks into gear as soon as you identify the need to expand your team — or better yet, you already have a few people in the queue, ready to hire, fully vetted and ready to go.

You don’t have to guess at the best way to locate applicants. You don’t have to slap together an interview process. You don”t have to figure out what questions you ask. You already have a proven system to support your end goal.

Pretty cool, huh?

That’s what this Millionaire Action Guide is: A step-by-step process for hiring the right person for the right job at the right time, developed specifically for those of you scaling from 2 to 20 employees. (If you don’t have that first hire yet, don’t worry — many of the principles introduced here will help you find that #1 employee. Keep reading!)

This guide encapsulates the results of my interviews with over 400 millionaires from all industries. I’ve taken the advice I’ve gained from them, combined it with guidance from my own mentors and coaches, and tested it in my own business and with dozens of my clients over the years.

This is the same guidance I provide my private clients, and I’m excited to share it with you in this Millionaire Action Guide.

One note: Of course, there are so many different elements that will affect your particular business, including where you are in your business’s growth and development, your resources, your industry, and more. So while I want to give you an infinitely actionable process, you’re going to need to use your brain a bit. If something doesn’t sound right, check it out.

I’m not a lawyer, accountant, or expert in employment law. What I am is a business owner myself, as well as someone who’s dug deep into what’s working with some of the most successful entrepreneurs in the world, then tested and validated that advice. Now, I want to share that knowledge with you.

Let’s get to it…

Jaime Masters


I’m Jaime Masters, founder of Eventual Millionaire. I’ve interviewed over 400+ millionaires and billionaires in business for my podcast, Eventual Millionaire, and I’ve been helping business owners make things more simple and more profitable for the last 10 years.

I compiled the knowledge and advice from my weekly millionaire interviews into a bestselling book, The Eventual Millionaire: How Anyone Can Be an Entrepreneur and Successfully Grow Their Startup.

My work with millionaires has also garnered the attention of media giants, such as Yahoo Finance (6x homepage feature), (5x), SUCCESS Magazine, Entrepreneur, Women’s Health Magazine, TIME, CNN, Business Insider and more.

In this Guide We’ll Cover

  • Getting Ready to Hire: Why build a team, when to start, and what type of team member to add
  • The Big Picture of the hiring process
  • Finding qualified applicants
  • Handling applications and interviews
  • Making an offer and onboarding your new team member
  • FAQs and troubleshooting
  • Additional resources for you to explore


Why Hire?

This is kind of an obvious question, right?

But I’ll answer!

It’s going to be really, really hard to build your business to seven figures and beyond if you’re doing everything yourself.

If you’re reading this guide, you already know that you can’t grow the way you want, and serve your customers and clients the way they deserve, if you’re stretched thinner every day. You probably already feel the pain of that “DIY” approach.

Bringing on additional team members will allow you to focus on your highest value tasks and projects, and work “on your business” instead of “in your business.”

Millionaire Tip!

Check out “The E-Myth Revisited” by Michael Gerber for a full discussion of the importance of working ON vs. IN your business. He stresses the importance of the entrepreneur separating him- or herself from the everyday goings-on of delivering your product or service to your customers.

One of my favorite quotes from the book:

“If your business depends on you, you don’t own a business you have a job. And it’s the worst job in the world because you’re working for a lunatic!”

Listen to my interview with Michael Gerber Here.


Whether it’s freeing you from the minutiae of admin tasks like billing and bookkeeping, or handling customer service so you can build bigger and better products and services, lightening your load in key areas pays off in terms of lower stress, fewer hours worked, more rapid business growth, and better results for your customers.

With this kind of return, it’s kind of funny that entrepreneurs are reluctant to hire.

But I get it — You might be worried about cash flow. How will you make sure you have enough revenue coming in on a regular basis to ensure you can cover the overhead associated with a new hire?

And then there’s the bad hire horror stories.

The ‘nes who look good on paper, but once they’re hired they take more time and effort to do a fraction of what you could do, but take twice the time.

Or the ones who start strong but blindside you when, just as you get them up and running, they take off for another opportunity or to tour Iceland with their folk band.

Or the ones who were awesome during the interview process and get along great with you, but when you put them in the office “pool,” they cause drama, gossip, and discontent.

I know you want the right person. You want someone who fits the team as it is but who will also help take you to the next level. You want someone who complements your weaknesses. You want someone who won’t take more time to manage than if you just did the work yourself.

That’s a tall order!

And that’s why I get this question ALL THE TIME?

“When Should I Hire?”

Now depending on where your business is right now, there’s a difference between hiring your first and your 51st employee. If you’ve been a solopreneur and are now thinking about bringing on that first team member, I want you to stop right now and check out the sidebar: “When Do I Hire My First Person?”

That will really help you with the mindset and skills you’ll need to make the most of your team members.

As I mentioned above, this guide is really about building a team and a business — not just an individual outsourcing tasks to a few contractors. So if you’re just at the beginning of your entrepreneurial journey, know that we may talk about some concepts and action steps that aren’t immediately applicable to you. But they will be soon enough!

And if you’re looking to hire employee #2, 5, or 10 — you’re in the right place. We’re going to take good care of you!

Those horror stories we talked about? Been there, done that — as have the hundreds of millionaires I’ve interviewed and whom I count among my friends, mentors and clients. Together, we’ve covered every mistake you could possibly dream up — and many you can’t! The good news is, this guide will help you avoid the majority — if not all — of the common hiring missteps.

Millionaire Tip! “When Do I Hire My First Person?”

Ummm? NOW!

Learning to delegate is an essential skill for an entrepreneur, and chances are you’re not very good at it (we’re not taught how to be millionaire business owners in school!)

Even if you don’t have the cash (or the workload) to justify bringing on a permanent full- or part-time employee, I want you to hire someone (even the kid next door for a couple of hours a week to help you clean your office and walk your dog) to take some of your lower-value tasks off your plate.

Learning to lead and learning to delegate are two of the most powerful skills you can master as an entrepreneur. I want you working on those NOW.

For more guidance, including a video and worksheet on making your first hire, check out this video I created here: “When to Hire.”

If you’re prepared to bring on a long-term employee rather than a few-hours-a-week helper, typically, the first hire I recommend is an admin or a virtual assistant (VA). This is someone who can take the lower-level, repetitive, administrative tasks off your plate.

Stuff like:

  • Managing your schedule, including arranging interviews and appointments
  • Taking the first pass at your email inbox (and in my experience, about 80 percent of your inbox can be handled before you set eyes on them!)
  • Creating and following up on invoices
  • Performing basic research
  • Simple project management
  • Basic customer service
  • Basic social media updating

You can follow the tips in this guide to make your first hire. There are also some great VA agencies that will help you find and evaluate candidates, and then hire and manage your Employee #1.

Check out:


When it comes to hiring additional team members, it’s always a balance between finances and workload.

There are some obvious indicators that your existing team needs more help:

  • Increase in turnaround time for deliverables due to growing workload
  • Bottlenecks — projects are getting hung up because someone (maybe you??) is taking too long to move it along
  • Decrease in quality because people are working so fast they’re missing things
  • Increase in number of hours you and your existing employees are working because there’s so much to be done
  • Complaints about workload from existing team members
  • Requests from clients for a profitable line of services or products your existing team doesn’t have the expertise to handle

Sometimes you just “know.” It’s just so painful to turn down business, or to keep doing what you’re doing. You’re stressed, your team”s stressed, you’re not operating on all cylinders.

Or, you may have set objective benchmarks, like “When we reach 1000 software installs, we’ll hire a dedicated customer service person.”

In either case, it’s clear that to move ahead, you need to add bodies. Honestly, if you’re even thinking about hiring, it’s time to hire.

Millionaire Tip!: Only As Are Acceptable

One of the first things I have my clients do when we talk about leveling up, is to sit down and rate their current team with a grade: A, B, C or F. (This is a concept I picked up from “Topgrading” by Dr. Brad Smart. See the “Resources” section for how you can access a free copy of his Topgrading ebook — as well as the complete “Topgrading” book.)

It’s really funny — no one ever gives a team member an “F.” I think it’s because they know I’d say, “FIRE THEM!” So they go with a “C” instead.

But I know that game? and when they rate a team member as “C,” guess what I say?


“But they’re average!” my client will plead.

“I don’t care. Are you running an average organization?” Cs have to go — immediately. (I know, it’s hard! And don’t fire them all at once – just do it as fast as you can find “A” players to replace them!)

So, the Cs are gone. That leaves Bs and As.

If someone is a “B,” I ask, “Can we train them to be an “A” If not? they have to go. And that’s REALLY hard because these are usually good people that you like? but you can’t keep B players and expect to create an “A” organization.

Only As are acceptable on your team.

As you go through this guide, remember that. We’re not looking for Bs or Cs. We’re not looking for warm bodies who can “fill in” until you find someone better. You are better off leaving a vacancy than bringing on a sub-performer who will ruin morale and send the message to other team members that less than “A” performance is acceptable.

Remind yourself over and over: Only As stay.

brad smart quotes

Once you sense the need to bring on another team member, there are some more structured exercises you can undertake to help figure out if you’re at the point where adding another body makes sense.

EXERCISE: Where Does It Hurt?

Let’s say you’ve hired your first team member — an executive assistant (see “Who to Hire” below).

You get the sense your current EA could be doing more higher-level tasks since he’s taken on some responsibility as a project manager, but you want to make sure that his current workload is covered.

Ask him to sit down and write down everything he currently handles that the new hire could take off his plate. Then have him estimate how much time he spends on those projects and activities.

Have him do the same for his anticipated new activities and projects, including a list of the activities and a time estimate. (If there’s a direct dollar ROI to those activities, have him add that in, too.)

If the list totals 20 hours or more, it’s time to bring on another person, either full or part-time.

If it’s less than 20, consider a contractor or freelancer to use on a project basis until the workload is consistently at 20+ hours.

What Type Of Hire

In today’s internet economy, there are all sorts of ways to add bodies to your team, including:

  • Freelancers/contractors vs. employees
  • Part-time vs. full-time
  • Hourly vs. salaried

NOTE: As I mentioned above, I’m not an expert in accounting or employment law, and depending on what country and even what state you live in, there are a variety of different legalities and tax implications of the type of hire you make. PLEASE make sure to contact an expert to ensure you’re handling payroll taxes, disability, withholding, etc. appropriately! (It doesn’t have to be complicated, and you don’t have to do it yourself? my accountant handles all these concerns for me!).

What I can speak to, though, is the difference between the broad categories of hires. What type you ultimately select will depend a lot upon your business, but I’ll give you an overview here:

Freelancers vs. Employees

When you hire a freelancer, you are hiring an independent contractor who is not technically (in the eyes of US law, at least) an “employee.” Typically, they’re compensated on an hourly or project basis, such as hiring a web designer to redo your website, or paying someone $15/hour to help register attendees at your annual conference.

Freelancers are great when you’re doing a one-time project that doesn’t require constant staffing, like designing your logo, creating an app, ghostwriting a book, etc., or the type of work isn’t frequent enough to warrant a permanent team member.

Millionaire Tom Gimbel explains it like hiring someone to mow your lawn or wash your windows. “It doesn’t mean you’re outsourcing the whole house,” he says. “You’re still going to decorate it and paint the walls and pick the colors, but you’re allocating a chore, a responsibility.”

Here are just a few of the projects that are commonly outsourced to freelancers/contractors:

  • Sales funnel implementation
  • SEO support
  • Software development
  • Website design
  • Copywriting
  • Graphic design
  • Video/audio editing
  • Legal assistance
  • Taxes/bookkeeping
  • Facebook ads
  • Affiliate/JV support during launches
  • …and anything you can think of!

Some contractors and freelancers might actually become almost like team members, in that you work with them again and again over the years. But there’s no ongoing employment contract. The agreements you create with this category (and you definitely need an agreement!) are for a specific project, a specific type of task, or a specific time period — for a specific dollar amount.

Because they’re independent contractors, you do not have to withhold payroll/Social Security/disability taxes. You don’t have to provide health care, pay overtime, or handle other benefits. Independent contractors are handled differently for payment and tax deduction purposes as well, so again, consult an accountant to see what kind of paperwork and documentation you need to create and file.

One main downside of working with freelancers is simply lack of control. The woman who designed your website a year ago may or may not be available next week for an emergency update. The guy who handled your paid advertising for the last six months may suddenly drop off the face of the earth without warning, and you have no idea what’s going on. When workers aren’t “your” employees, you have less say over their workflow, work process, and even cost.

Speaking of costs? because freelancers typically pay their own taxes and overhead, those costs are rolled into the price you pay — which can mean you pay a premium over what it might cost to handle the same tasks or projects in-house. That’s why it’s essential to regularly review the projects you’re outsourcing to see if it makes more sense to consolidate and bring them in-house.

When screening for contractors, you will want to go through the same sort of screening as if you were hiring an employee. Millionaire Nathan Hirsch of says, “If you’re going the contractor route? you have to do your due diligence. What other clients they work for, when can they work for you, what their long term plans are. If you see on their resume that they’re switching jobs every three months just like you would do with an employee, they’re probably not the best fit.”

Sidebar: How Much Will It Cost?

To get a sense of how much a freelancer or employee will cost on a per-hour basis, you’ll need to do a bit of research. There are a number of online sites you can dig into in order to see general ranges for different services.

Here are just a few:

  • (check your local market, “gigs” and “resumes,” as well as the “jobs” categories)

Remember, this will just give you a taste. Ranges will vary widely, depending on experience, geographic location, and skill.

For instance, I did a quick search and found logo design for as little as $5/hour to as much as $100/hour, with most in the $45-$50/hour range.

Content writing ranged from $4/hour to $100/hour, with most also falling in the $45-$50/hour range.

Again, this is just one data point.

When you’re looking for “A” players, you’re dealing with the best. And they’re probably not going to come for $4 an hour.

Part-Time vs. Full-Time

In general, I prefer to hire full-time employees vs. part-time.

I only want to hire people who are 110 percent committed to their job and to the business, and I find that it’s difficult to get people who are “all in” when they’re part-time. They just don’t have the same commitment if the job is something they do on the side, away from their regular work or if they have a few part time jobs. Something else ends up being the priority — school, another job, etc. — and then that takes away from the culture of excellence I’m trying to create.

There is one exception I want to mention, and that is stay-at-home parents — super-smart moms and dads who are choosing not to go back to the workforce full-time because they want or need to be available for their kids. They’re committed, professional, and talented, and are looking for fewer hours per week than a “regular” office job would require.

I’ve had some amazing success hiring these types of parents part-time through sites like

Not every position will work for a part-timer, but if you want a permanent employee instead of a contractor, think about hiring a stay-at-home parent looking to keep his or her foot in the business world!

Hourly vs. Salaried

In general, I prefer to pay hourly vs. salary. It gives me more flexibility in terms of pay, and also in terms of hours and days worked. I keep everyone on hourly unless I find myself paying a ton of overtime, and then I’ll consider moving someone to a salaried position. But even then, they’d start as an hourly employee.

One note: Sales can be a different beast entirely because their compensation is typically a combination of base pay and commission.

Sidebar: Legally Speaking? What’s Considered “Full Time”?

According to the IRS, “A full-time employee is, for a calendar month, an employee employed on average at least 30 hours of service per week, or 130 hours of service per month.”

Once someone reaches full-time status, you need to follow other legal requirements regarding the Affordable Care Act (ACA), overtime pay, and other benefits.

You can find out more about overtime requirements here.

The requirements on the ACA will likely be changing in the upcoming year, so consult a lawyer or CPA for more info.

Words from Doug Kisgen of

There are two aspects of job descriptions:

1. What do you put in an ad to attract the right candidates?

This should be done with the “who” in mind and very little with the “what.”

Job ads are bait. It’s best to only set the hook with the exact bait you need to get a nibble. So, I recommend short ads in general (with some caveats). The first few sentences should not be about the company, but about the person you are trying to attract. Think of traits.

Does this person need to be a self-starter or more of an order-taker? Extrovert vs. Introvert? Big picture or detail-oriented? And many more…

Put words in the first paragraph that would say to the right person, “This sounds just like me.” One good litmus test after drafting the ad is to run it by someone on your staff, who has similar traits, and see if it appeals to them.

In terms of “what” (experience, skills, education), I suggest limiting this in order to increase the number of total candidates.

For example, if you think the job requires 5 years experience, put 2-3 years instead. Aim lower. We want more people to raise their hands at this stage, not less.

2. Once a person is hired, the job description (or more of a scorecard) should be reviewed during the interview process.

The job description is now more extensive and should include KPI’s/measurables. The best source for this is Topgrading by Dr. Brad Smart and Who by Geoff Smart. Here’s an example.

And here’s a good resource for more job description tips and examples.

I bet you’re saying, “Jaime, I want to hire someone who can DO IT ALL. They’re a little bit of this, a little bit of that, and A LOT awesome!”

However? vague, imprecise job descriptions lead to vague, imprecise results — which is exactly what I DON’T want for you!

The better you’re able to specifically identify the role you want this new hire to fill, (a) the better the odds of finding someone who will say, “I can do that!” and (b) the better your ability to evaluate the likelihood they’ll be what you’re looking for, and (c ) the happier they’re likely to be because they are doing the job they were hired to do.

I also know that in start-ups, employees typically wear multiple hats. But as hard as it may be, you’re going to have to do your best to hone in on the specific job you’re hiring someone for.

There’s a tendency to want to hire someone “just like you” because you want to clone yourself! But that’s the wrong approach. Instead, figure out where your weaknesses are. Those things that you’re really weak at? That’s what you should be hiring for first.

The millionaires I interview stress that the “one thing” that will take you to $1 million and beyond is “Knowing your strengths and leveling up on that.” That requires some serious self-reflection! (Which means you probably are going to want to take the assessments that I talk about in Section Two!)

EXERCISE: Future-Casting

You know you need to hire someone — great! Is it a programmer, a full-time customer service person, a web designer?v- (Or maybe you want one of each!)

One exercise I ask my clients to do is “future-cast” their organizational chart.

Here’s how it works:

Sit down with a clean sheet of paper and sketch out your org chart right now. Obviously, that’s you right at the top!

But underneath you, what boxes are there? Who’s handling finance, operations, customer service, research and development, engineering, marketing, sales, HR? (Chances are, most of those boxes have your name in them — that’s okay!)

Now, hop in my time machine and transport forward five years.

What do you want that org chart to look like now? What boxes will exist that don’t exist now? Where has your name been replaced by someone else’s?

Remember, not everyone’s ideal business is the same. Some people envision themselves sitting on top of a 500-person organization in five years, while other people would cringe at that thought because they want a lean, mean machine.

The number of boxes on your org chart doesn’t matter — what matters is that you have a clear idea of what those boxes are, and where YOU are spending your time!

Once you’ve figured that out, you can backtrack to figure out what your next hire, or better yet, five hires, should be.

If you envision a team of hundreds, removing yourself from which box will have the most impact on your ability to get there?

Or, if you plan on outsourcing many tasks, who will oversee those contractors?

Thinking ahead is the ONLY way to create your ideal business. Yes, your organization — and your org chart — will be a living “organism” that will change and morph over time. But you have to have some kind of vision in mind to move toward NOW.

Sidebar On Finances

When you’re hiring a salesperson, it’s pretty clear cut to determine their ROI. They need to more than cover their salary, commission, and other benefits to justify their hire. But other positions aren’t so cut-and-dried. How, for instance, do you determine what the value of a customer service person or a developer or designer?

There are a couple of calculations you can do.

First, who is doing the work now? If you’re doing all the customer service, what is the opportunity cost of each hour you spend answering emails or phone calls instead of your higher value tasks?

For instance, if you’re spending 25 hours a week on customer service, and you could hire a customer service person for $12 an hour, that work is valued at $300 per week.

However, in that same amount of time you could have worked on a project for a client at a value of $5000, or $200 an hour.

That means by bringing on someone to handle customer service, you should be able to generate an added value of $188 an hour.

By the same token, if you are currently having your $40/hour web designer handle questions and comments that come in via email or the site, you’re losing $28/hour by having him or her deal with customer service issues that can (and should!) be handled by a lower-paid rep.

Here are other questions to help you calculate the worth of an additional employee:

  • Will adding this employee allow you to better service your clients? How? What is that higher level of service worth? Will you be able to pass that onto your clients?
  • Will adding this employee let you transfer tasks from an existing, higher-paid employee? What is the differential in their pay? What will the existing employee do with the freed-up time? What is the value of those tasks?

You can also check salary databases like:

Again, these are just data points. Your experience might be different.


Now that you have a good idea of whether it’s time to bring someone on (usually: YES!) and what responsibilities you’d like them to handle, it’s time to take a look at the overall hiring process.

A note on the process: Whether you’re hiring your fifth or 25th employee, I want you to develop a step-by-step system for hiring. By standardizing the process, you’ll be able to replicate the system over and over again, saving a ton of time and, ideally, removing yourself from most of the entire process.

This standard process is often called a Standard Operating Procedure, or SOP, in the corporate world. It’s an encapsulation of best practices that removes guesswork and recreating the wheel. See the sidebar for an example of my hiring SOP.

Sidebar SOP Example

Systems enable companies to save time and ensure quality as they grow. They also let you know that your future marketing manager is using the same process and evaluation criteria as your future CFO will use. Click here for an example of my hiring SOP.


Once you’ve decided what type of person you need to fill what role, here’s a roadmap of the process (we’ll get into the specifics of each piece, so don’t freak out!):

1. Give yourself a target date when you want to have the new hire start work (This may take more time than you think). Create a job description and set application procedure, including assessments.

2. Post the description to appropriate places and put your hiring antenna on (you might see the perfect candidate at the local Starbucks or working the front desk at your dentist’s office!)

3. Compare resume submissions with job description.

4. Hold 15-minute phone interviews with first-round applicants.

5. Have those passing first round to take additional assessments as necessary.

6. Hold second-round competencies interviews, including team members as appropriate.

7. Give skills tests – could be via email.

8. Review tests.

9. Narrow it down to at LEAST 2 you are super excited about. I actually prefer three!

10. Give trial task to final group.

11. Review trial tasks (so you can compare apples to apples) and rank your candidates.

12. Make your offer!

Now let me warn you — as soon as you make up your mind to bring someone onboard, you’re going to get really impatient. You’re going to want to hire the first person who submits a resume that looks halfway decent.


You’ve probably heard the old adage, “be slow to hire, quick to fire.” It’s true! If you rush into hiring someone, you might overlook really strong candidates — and overlook shortcomings of the candidate you have your sights set on.

The hiring process can take anywhere from a few weeks to a few months. In my experience, the fastest it can be done is about a month, and it takes about 6-12 weeks on average.

As much as you think you can shortcut it, resist the temptation!

Now that we’ve got that out of the way, let’s discuss the elements of the hiring process in more detail.

First, the job description.

After you’ve established what you want this stellar employee to do, let’s get started crafting a stellar job description to match.

One of the biggest mistakes I see people make is watering down their job description to the point it’s super-generic, and really uninteresting. I’m betting you and your company are neither, so your job description shouldn’t be, either!

I direct my my clients to this great article from Mashable on how to create a stand-out job description (it’s what I use as part of my hiring process. You can see a few samples of my job descriptions here.).

In sum, create a specific, interesting job description that not only lets potential applicants know exactly what you’re looking for in terms of qualifications and skills, what their responsibilities will be, and how to apply, and also gives a sense of what makes your business different from others.

Where To Find People

My first line of referrals is my network. I love getting hiring recommendations from my colleagues, mentors, clients, and millionaires.

So spread the word among your friends and business network. You might even want to send out an announcement to your email list as people already in your “world” will have a better understanding of you and your business.

These days, online job boards have replaced the newspaper classified ads of yesterday.

Here are the broad-based sites I always use when posting for jobs:

  • (choose your local market for local jobs; post across the country if local isn’t required) Cost $25 per post per section
  • (I typically set a budget of $100 – with a low cost per click)
  • (if it doesn’t have to be local)

There are also a number of location-specific boards and even Facebook groups, such as or Austin Digital Jobs here in Austin, and for Portland, OR. Other niche sites have job boards too like for writers. Ask your network for recommendations of sites where you can post your job announcement.

Sidebar: Do You Need To Hire Locally?

The answer, like a lot of things, is “it depends!”

For some of my positions, like my personal assistant, I want them to be local to me, even if they eventually may end up working remotely from home. I want to meet and train them in person, and then over time, as their competence and my comfort level increases, they have the choice to work remotely.

The benefit to having someone locally, whether or not they work with me day after day, is that they’re close by and I can occasionally catch up with them in person — which increases the connection, cuts down on misunderstandings, and makes it much easier to train them. In the early days when you’re getting to know each other, it’s a lot easier to keep an eye on them and what they’re doing, answer questions, adjust or correct workflow, etc. — all of which would be more difficult if not impossible if they live across the state or around the world.

Of course, the converse is that if you share an office space, your own schedule — and physical location — will need to accommodate them. If you’re used to working strange hours, heading to the coffee shop, the pool, or your home office as the mood strikes you, you can lose some flexibility.

If it’s not essential to work side-by-side with your team, I like to build in flexibility. My own schedule changes from week to week, and I travel a fair amount, so even if I told someone they had to be “in the office,” I wouldn’t always be there myself!

For other jobs and projects, you may not need your team member to be on-site at all. In particular, I know several web and digital agencies, such as Rich Brooks’s Flyte New Media in Maine, that operate at least partially remotely. And for salespeople (who are always a little bit different from everyone else!), they may be on the phone, in meetings, or on the road a lot of the time anyway.

As far as needing some kind of central “office,” more and more millionaires that I interview are totally okay with having their teams work remotely.

That being said, when you’re not in the same physical spot, you need to ramp up your communication and team-building efforts! Remote teams often get together several times a year — biannually or even quarterly — for retreats because nothing replaces a face-to-face connection. So there are tradeoffs with expenses and advantages.

NOTE: For information on the pluses and minuses of hiring internationally, see the FAQs in Section 5.

The First Hurdle: Evaluating The Resume And Application

You’ll hear some career gurus say that resumes aren’t necessary anymore, but I disagree. Even for a personal assistant or entry-level position, I ask for the applicant to submit their resume.

Resumes are one of the few apples-to-apples comparisons you’ll have, and it’s an easy way to review all of the material they think is important at a glance. Resumes also give a great indicator of attention to detail (spacing, spelling, etc.) as well as professionalism.

The goal for this first pass through the applications and/or resumes is to evaluate a couple of things:

1. Did they follow instructions?

2. Are there obvious problems (lack of attention to detail, “weird” stuff)?

3. Do they have the experience, skills, and other qualifications you mentioned in your job description?

This first pass is something you can have a support person or admin do. They can quickly toss out any clunkers.

If they pass the first evaluation, your admin can schedule them for a short, 15-minute phone interview. There is no need for you to get involved before this point! In fact, it’s probably better if you don’t.

Millionaire Michael Hyatt tells a story on his podcast about how, when hiring a personal assistant for his wife, his admin went through the 45 submitted applications, did a short Skype interview with the dozen or so who passed the minimal qualifications on paper, and then presented three final candidates to Gail and Michael.

The later in the process you can be brought in after the initial criteria have been established the better (Remember how I warned against hiring without going through the process? That’s what we’re guarding against — If you spy an application from someone who went to your high school, who also raises greyhounds, and who lives two streets away, you just might want to pull them out and say “Hire them!” That’s a no-no!)

In the next section, we’re going to dive deep into interviews: Who should be interviewing candidates, how they should be conducted, and what you should (and shouldn’t!) ask.

But first, I want to have a discussion about?


I’m a total data girl. If I can use objective tools to inform and justify my decisions, I’m super-happy.

A lot of the hiring process is subjective rather than objective. And that’s why I’m a big believer in using tools like assessments to help bring some data to the process.

Of course, any assessment tool has its limitations. People are unique with unique skill sets, experiences, and backgrounds, but assessments do give us a way to put some rails on what we’re measuring, so we can get a better sense of how a person might fit into our existing organization, how they prefer to take direction and be managed and motivated, and what matters to them.

There are a ton of assessments out there: From personality tests like the Enneagram and the Myers-Briggs type indicator, to the DISC assessment, an IQ test, and a dozen more, you can look at everything from someone’s astrological sign to their favorite color.


Not all this info is going to be helpful in determining whether a candidate is a good fit in your organization. I’m all about sharing JUST the best info, so in my experience, these assessments are invaluable (and they’re the ones I ask all my potential hires to complete):

1. DISC Assessment. The DISC assessment is a behavior assessment that helps employers determine a person’s work behavior patterns or styles. It can help you see if the responsibilities of the position match the general profile of the person you’re considering. It can also help pinpoint missing “styles” or “types” in your current team. (Note: Full disclosure: I often recommend the DISC because it’s free! Take a sample test here to find out more.)

2. Values Assessment. The Values assessment (which is also free to take) can tell you what a candidate values most among seven different categories. It can help you figure out how to motivate them. It will also give you a sense of whether they may be satisfied with their role in the organization. For instance, if they are highly motivated by economics (“a drive for economic or practical returns”), they may be a great fit for a sales position that is highly rewarded on a commission basis. Take a free assessment here.

3. Kolbe Assessment. The Kolbe A Index measures your instinctive way of doing things and the result is called your M.O. (method of operation). It’s a great indicator of the way someone approaches a situation and takes action — and if they thrive most when innovating, building, evaluating, or coordinating. Obviously, certain types are more suited for specific jobs and responsibilities than others!

On this assessment I am a quick start, which means I like to start things quickly but don’t have great follow through. That is why I have hired people on my team who have great follow through. I am also a fact finder, which is why I love interviewing millionaires, because I get the best of the best advice and information. Tons of the millionaires that I have interviewed use this not only for themselves, but also for when they hire employees.

4. Culture Index. The Culture Index is a tool I discovered from millionaire Doug Kisgen. In just a few minutes, it will give an uncannily precise view of someone’ strengths, weaknesses and talents. I had my whole team take the assessment so I can see how potential new hires will fit — or not — into the existing culture of the business.

As valuable as this assessment is, you can’t take it independently – you have to access it through a consultant like Doug, and you pay for access and interpretation. If you’re bringing on five or more people in a year, it’s worth the investment.

Each of these sheds light on different elements of someone’s work personality, strengths and potential weaknesses, and likelihood they’ll fit into your team like they were made for you.

Will they tell you EVERYTHING about a potential hire? Of course not. But they give you a more complete picture of what they’ll be like to work with, and in some cases, work for. Kisgen says, “Even with [assessments] it’s still not simple?. But I will tell you that it takes a ton of the headache away and it takes the guesswork away.”

You’re doing yourself and your entire team a disservice if you don’t use every reasonable tool at your disposal to make sure your new addition will be the best fit possible.

Sidebar: Values Statement

How do you know if someone’ values fit your company values?

Well, you better know your company values first! Get super-clear on your company values. And then once you have those, make sure NO ONE gets past the evaluation process if they’re not in alignment.

Values are critical because your employees are a reflection of your business, and your business is a reflection of you.

As millionaire Jeff Hoffman explained to me, you want to make sure that each employee can do a great job of standing in for you and doing what you’d do in the same circumstance. Ask yourself, “If I was not here, would [they] make the same decision I would make? Do we have the same values? Do we believe in the same things? Do we care about the same things?”

One key tip now: make sure when you create a values statement, it’s short and memorable. One of my clients created his company values statement, and it sounded great — but it was super long! I said, “Can you remember all this?”

“I guess I better pare it down?” he said. EXACTLY. šŸ™‚

He realized that it needed to be short enough so not only he was able to remember it, but his entire team could keep it top of mind as well.


As I mentioned above, if you have a person on your team who can conduct the first round of interviews, back off and let them — after giving them careful guidance about how to conduct the interview, of course.

During the first interview, you or your proxy can evaluate the applicant for general interest, ability to communicate, and specifics of their background/experience.!

The interviewer can ask questions like:

  • “What made you interested in this position?”
  • “What are your salary requirements?”
  • “What is your availability?”

Sidebar: What To Ask In That First Interview?

The first 15-minute interview is really about screening. You can wing it by asking questions about their resume, but it’s better to be prepared — and it’s also good to ask applicants the same questions!

Here’s a list of questions that you, your assistant, or the hiring manager can ask:

  • Why are you leaving your current position?
  • When will you be available to start?
  • What made you interested in this particular position?
  • What skills do you have that complement this job?
  • What are your salary requirements?
  • What skills do you have that complement this job?
  • What are your goals?

After that first round of interviews, even if you only have a couple of successful candidates remaining, I like to administer the assessments.

Then I’ll do a one-on-one with the candidates and learn more about them, and confirm what the assessments may indicate.

In that interview, you’ll want to dig in a little bit to how people think, says millionaire Nathan Hirsch of “You can kinda trick them and challenge them by asking them questions about their past job, asking them about situations,” he says. “That’s why you hear all those crazy interview stories of, “Someone asked me how many marshmallows it takes to get from here to Wisconsin.” They don’t really care how many marshmallows, they care about how you would problem solve.”

After that, I’ll make sure the rest of the team has an opportunity to meet the applicants. “I want the person who I’m ultimately going to hire to meet with every significant stakeholder in the company,” says Michael Hyatt.

Competency interviews (rounds 2-3, depending on your team size and availability), are all about the person’s ability to get the job done and meet the position’s requirements.

If the person is being hired for a customer service position, for instance, someone might role play with them. If they need to have project management skills, you might ask them to explain how they’d go about prioritizing certain tasks, handle a team member whose deadlines are slipping, or tell you about their methods of keeping projects on schedule.

Then, one of the last things many millionaires do — including Michael and Tom Gimbel, as well as radio personality Dave Ramsey — is to get together in a social setting — coffee, drinks, dinner — with that person, and possibly their spouse. “Depending on the level of the person, the more I’ll invest from a time standpoint and do dinner with someone coming in who’s going to be a direct report,” says Tom.

Not only does it let you see them in a more relaxed environment, you also might pick up on some social cues that didn’t come out in the more structured office or phone interview. Michael tells the story on his podcast of one time when he was about to offer someone a position, he went for dinner with the candidate and his wife. His disrespectful treatment of his wife in such a high-pressure situation was an immediate red flag. Michael passed on the candidate.

Sidebar: How Many Interviews Do We Have To Do?

I can already hear you whining? “But Jaime? multiple interviews! Isn’t one enough?”


Let me remind you, we’re going after A players and ONLY A players — and it will take effort and time to find them!

Millionaire Doug Kisgen, who helps me with my hiring by administering the Culture Index to my potential hires, told me that in the book “Work Rules” (see resources list), the authors investigated the way that Google locates, evaluates, and brings on new talent.

Based on the company’s huge sample size, they determined that the optimum number of interviews is 4.


That might sound crazy — but Google probably knows what they’re doing!

The first interview could be your admin doing a quick phone or Skype interview to check the person out.

The second interview could be you, one-on-one, diving into their skills, motivation and competencies a bit more.

The third interview could be a team interview where you sit back and let the rest of your team — with pre-training from you — interview the candidate.

Sidebar: The Team Interview

Make sure to train your team to interview and what you want them to look for. The better you can train them, the better results you’ll have.

Tell them to look for these things:

  • Do you see them as a good fit with the team?
  • Will they get along with the team?
  • Will they contribute positive value to the team?
  • If the team is missing that one core skill set that we’re hiring for, do they fill that?
  • Do you like them?
  • Are you enthusiastic about having them join the team?


Then interview #4 could be where you and your team members see the person in a social setting.

Remember: A players are going to require A effort on your part.

It’s worth it!

Yes, it takes time. Yes, that time translates to money. But the cost of a bad hire — estimated to be 10X the person’s salary or more — is way, way higher than the cost of another round of interviews.

Do it.

Rating And Eliminating Candidates

The first stages of the hiring and evaluation process are pretty rigorous — and pretty objective. You’re looking for check-box answers (“Are they available when I need them? Do they have the skills required? Do their assessments indicate they’d be a good fit in this role/on this team?”)

After candidates make it through those early stages, you can rely more on your gut feel — but ONLY after the objective data indicates they’ve satisfied the requirements!

What you’re looking for is someone who brings MORE value to your organization than you’ll pay in wages.

Olga Pechnenko of says of 100 applicants, only about 12-15 will make it through the initial application/resume screening and rate a 15-minute round one interview. Then 7-8 will make it past that interview to the next round, ending up with only 2-3 for the third interview round.

Millionaire Tip: Red Flags

Many of my clients want to like and be liked — I know how you feel!

But when it comes to hiring, you need to look for reasons to ELIMINATE candidates — not keep them.

Here are some red flags that should immediately cause you to pause:

  • What other commitments do they have? If you need someone who’s available on weekends or is willing to work overtime, you will want to know about any other claims on their time. “If I talk to someone and they do piano every day at 5:00 p.m., and then every weekend, they’re booked, and they’re traveling, and all this, that’s a red flag for me,” says Nathan Hirsch of
  • Communication. If you feel like you’re on different wavelengths and communication isn’t clear, that’s a warning signal.
  • Attention to detail. “If I have someone who’s showing up for interviews late or who can’t figure out what time zone matches mine, to me, that’s a red flag,” Nathan adds.
  • Things you don’t have but want someone to compliment you — like grammar and spelling! If you’re a lousy writer or speller, for instance, you probably want your assistant to have that skill.
  • Dishonesty of any kind. That’s a non-starter — whether it’s how long they worked somewhere, why they left, or how much they made at their last job.
  • Lack of passion. They need to have some sort of fire in them — whether it’s for teamwork, customer service, coding, design, or even accounting? I want to see their eyes light up at some point in the interview process!

Any one of these would be cause for serious reflection, if not immediate elimination. More than one? Move on!


Ideally, you’d have your choice of candidates who fit every skill and competency requirement, are fantastic people with stellar experience, and who you’d love to work with.

But sometimes — usually — there are a few gaps. Maybe they are perfect in every way but industry knowledge. Or they look great on paper, but they’re missing “something” in a live interview.

How perfect do they have to be?

According to the millionaires (and my personal experience), they don’t have to be 100/100 to get the job offer.

There are some things that are immediate causes for removal from consideration: Dishonesty, rudeness, and even that “funny feeling” you get when you meet some people, where you feel like there’s something there you can’t put your finger on. PASS ON THEM. It’s not worth the risk!

But they don’t have to be perfect. In general, attitude and potential are more important than skill.

“If you start at 80% or even 70% of what you ideally want, but they’ve got a great attitude and great value congruency and vision, you’re going to build a great team,” says millionaire JV Crum III.

Millionaire John Spence agrees. “Hire for attitude and aptitude, and train for skills,” he says.

That doesn’t mean you’re settling for “B” or “C” players; you’re looking for “A”-level potential and aptitude.

Put it this way: You want to create a learning environment because your business will be changing all the time. You and your team will never be 100 percent up to speed all the time — you’ll constantly be pushing outside your comfort zone. Having the desire to learn and grow and change and contribute? You can’t teach — or learn — that.

BUT? (like always, there are some caveats!)

If you have a very small team (under 5 people), you will need to find someone with a combination of skill AND attitude/aptitude. You can’t afford a long ramp-up period; you need someone who can hit the ground running. Be realistic about your ability to train someone and get them up to speed before they’re self-sufficient and filling the job responsibilities at an “A” level.

Sure, you might pay less for someone without the requisite skills. But what may look like a bargain (“They’re awesome! I’ll just train them!”) may turn into a liability when you spend more time and energy getting them to independence. You might be better off paying a bit more for an “A” player who is awesome AND has the skills you need!

Sidebar: Salespeople Are From Mars

Are you hiring salespeople? If so, you probably already know that top sales folks are a different breed — in a bunch of ways!

As my friend and superstar sales recruiter Olga Pechnenko, owner of, says, awesome salespeople know how to play the game. That means the usual screening methods — assessments, interviews, etc. — may not work if they’re smart enough to “game” the system. “They’ll tell you exactly what you want to hear,” she says.

So what do you do?

You could hire a recruiting firm (like Olga’s!). But if you’re doing it on your own, don’t ask them what they expect you to ask.

But before you even get to the interview stage, you have to dive deep into the role you expect this salesperson to fill. Not all sales jobs are the same, and someone who does very well with phone sales for a low-cost product may be awful at generating business for a five- or six-figure deal.

So outline the nature of the job:

  • Sales quota (how much are they expected to sell?)
  • Sales cycle (how long does it typically take to close a sale, from lead to signed deal?)
  • Size of the deal (how much does a customer or client typically buy at once?)
  • Business-to-consumer or business-to-business?
  • Inside sales or field sales?
  • How much travel is involved?
  • etc.

Know what you’re looking for so you don’t even interview the wrong people to begin with!

Then when you write the ad or job description, write it in such a way that the ideal candidate will say, “That’s me!” (That’s actually great advice when you’re hiring for ANY position).

When evaluating a salesperson’s resume, Olga says to look not at the words, but at the numbers.

  • How long were they at their previous jobs?
  • Are they telling you “I was 120% of quota every year” or “I grew the account significantly?”
  • Look for RESULTS. (If they don’t include specific results, there were no results — not good!)

Then look at a match between the job requirements and the skills and experiences laid out in the resume.

Only then should a potential sales recruit make it to the interview stage? and Olga says that interview should be TOUGH. She spends the first 10-15 minutes “poking” at the interviewee, trying to make them uncomfortable and put them on the defensive. Why? Because she wants to know how they’re going to respond to an unpleasant customer or tense situation.

That means asking questions like:

  • You say you’re a top performer but your last two years were flat. Why?
  • It sounds like you make a lot of excuses. Can you tell me more about that?
  • I have a couple of concerns about your resume? why were you at your last three jobs for only 18 months each?

(This can be really hard for “nice” people? like me? it’s a learned skill which you will get better the more you do it!)

After they do a good job of answering the tough questions, you can soften up a little bit (you don’t want them to think you’re a TOTAL jerk, after all!).

Remember, a salesperson should be AWESOME at following your hiring process. After all, they’re selling THEMSELVES.

Making Your Final Decisions

One of the best pieces of advice that I got about hiring from my mentor was to keep looking until I had two people I’d be happy with.

Sometimes, like I warned against before, we will stop as soon as we have someone halfway decent who can fill a chair at the table. But if we force ourselves to look for not one, but TWO candidates we’d like to hire, we’re ahead of the game in a couple of key ways.

First, you know what’s out there. You didn’t settle for the first one.

Second, at this point in the hiring process, you haven’t extended an offer yet. You aren’t 100 percent certain your offer will be accepted, or that you won’t come to a bypass on working hours, pay, or other considerations.

Next, because you had two great options, you know no one is irreplaceable. If your “right hand guy or gal” quits or gets sick or otherwise has to leave unexpectedly, there’s someone (and probably more than one) equally good out there.

So keep going until you and your team have two great candidates. Then get ready for the final steps?

Background And Reference Checks

Many people take more care in choosing a mechanic for their car than they do in selecting a new employee!

If there’s one thing all millionaires agree on (other than the need for multiple rounds of interviews), it’s the absolute necessity of checking references and running a background check.

I’s not enough to see a list of people your candidate claims she’s worked for, and who will say nice things about her. You have to actually CALL them and ask. “Did so and so do this job for you? How long did she work there? She said her title was X, can you confirm? Would you have any hesitation about hiring her again? Why did she leave?”

In fact, one of the questions I ask the applicant before I conduct background checks is, “Is there anything that might show up on your background check or in calls to your references that you want to tell me about now?”

This gives them the chance to explain what might come up BEFORE you hear it from a third party. And also, it’s a great checkpoint. If they say, “No, nothing!” and then you get a report that they’ve been convicted of multiple DUIs or their second employer let them go under less than stellar circumstances, then you DEFINITELY don’t want to hire them.

When you do the reference checks, read between the lines. A lot of people today are really hesitant to say anything bad about a previous employee, for fear of being sued.

So listen for the tone of voice. Are they enthusiastic? Do they say, “Yes, she worked here,” or do they say, “Oh my gosh, she was amazing, we’d hire her tomorrow if she moved back?” Their enthusiasm — or lack thereof — is MORE important than the words they say. (And that’s a big reason why you should make reference checks by phone, not by email).

Background checks go deeper into criminal records, bankruptcy records, and more.

According to, a background check could be as simple as verifying your candidate’s Social Security number, to a very detailed account of the person’s history. A background check could cover:

  • Driving records
  • Vehicle registration
  • Credit records
  • Criminal records
  • Social Security number
  • Education records
  • Court records
  • Workers’ compensation
  • Bankruptcy
  • Character references
  • Medical records
  • Property ownership
  • Military records
  • State licensing records
  • Drug test records
  • Past employers
  • Personal references
  • Incarceration records
  • Sex offender lists

You might think this information is superfluous, and it might be. But if your new employee is driving as part of their job, or coming in contact with confidential financial information about you and your business, it’s essential to know more about them.

There are a number of companies that will do basic background checks for you for a nominal fee — as little as $20 for a basic public records check.


How Much Do I Pay?

You should have a good sense of the range of compensation for the position, based on the resources listed above.

But before you make an offer, ask THEM what they want first!

I suggest this for several reasons. First, it’s possible they’d be very happy with less than you had planned on offering. That’s a win-win!

Next, letting them set the bar gives you a great idea of what they think of themselves — how confident they are. Of course, if someone’s asking for a lot, that doesn’t mean they’re worth that? but it’s great that they have the confidence to ask for it! Remember, you’re looking for “A” players, and they usually have a good sense of their own worth.

A few other considerations:

  • Cost of living. Hiring in NYC is almost ALWAYS going to be more expensive than hiring in, say, Maine (where I’m from!). However? you can make this work to your advantage if you’re hiring remotely. You can hire someone in a lower cost of living area and pay them less than you’d pay someone in a major metropolitan area.
  • Required skill level. Typically, the higher and more specialized the skill set, the higher the compensation. Just as a brain surgeon makes more than a Starbucks barista, someone with specialized skills will command more than someone whose job tasks are easily mastered.
  • Bonuses and other benefits. We won’t get too much into bonuses and benefits here, as it’s a specialty in and of itself, but often there are other considerations that can compensate (no pun intended!) for a lower dollar wage. These include (but aren’t limited to) training, performance bonuses, flexibility, retreats and team building events, etc.

Millionaire Tip: Reward Performance

If there’s a gap between what your candidate wants to be paid, and what you had in mind, negotiate!

  • Stress the non-monetary rewards (listed above)
  • Hire at a lower rate, but offer bonuses
  • Start them at a lower rate and then offer them incremental increases according to their performance.

For instance, let’s say there’s a $2 gap between what you are prepared to pay and what your new hire would like. Tell them they’ll come on at $16, which you’ll raise to $17 after they complete their first three months. Then you will give them an increase to $18 — their desired rate — at their first year anniversary.

Making The Offer

Congratulations! You’re ready to make the offer to your #1 candidate. You’re probably very eager to get them up and running and contributing to the team? but don’t cut corners now!

Once you’ve decided on an appropriate hourly wage or salary, make the offer IN WRITING and have them sign the offer letter to indicate their acceptance. If they have questions or want to work out specifics (pay, for example) do that over the phone or in person, and then issue a new letter. You can see sample offer letters here.

I always start my new hires on a temporary/contract basis for 60 days. This gives us time to get to know each other and figure out if this is going to be as amazing as we both thought it would be! It’s much easier to enter into an agreement knowing you have an “out” for 60 days if things aren’t working out. (Of course, you?ve done such a great job hiring that we know that’s not going to happen…)

Note: I’ve said this like a zillion times, but I have to repeat it here? Consult an attorney and a tax expert about the implications of hiring! There are so many different factors, from what state you’re in to what country they’re in, how many hours they’re working, the type of job they’re doing, etc. I don’t want you to get caught in a bad position — so get expert advice early on!

The Onboarding Process

Once your future team member signs their offer letter, don’t forget about them! Now is not the time to throw them in the water to see if they can swim. You need to have a considered, deliberate process for training them and assimilating them into your company culture.

I always set 30- and 60-day evaluations upfront so the new hire knows that they’ll be talking directly with me at those times. But I also provide a lot of opportunity for us to connect more informally.

Yes, things are crazy — that’s why we had to hire more people, right?! — but you HAVE to make time for your new employees. My former coach, millionaire Amy Applebaum, says to make your new hire your TOP priority for their first month (or the top priority of whoever is training them). Just as you’d let a new client know they’d made the right decision by choosing you, you want to let your new team member feel absolutely incredible for joining.

Here are a few of the things we do to onboard our new hires:

  • Introduce them to the rest of the team. They’ve likely met everyone during the interview process, but it might all be a blur. Let them know who’s who, who to contact for what types of questions, and everyone’s contact information. This is a great time to show them the org chart you prepared — with their name on it so they see how they fit the big picture.
  • Let them know the communications standards. Some teams use Slack (we do!). Some use interoffice email. Some use Skype, Basecamp, or something else (sometimes even the phone!). Tell them how to contact others, formally and informally.
  • Make them feel welcome. This can be as simple as taking them to lunch (if you’re all local), or sending them the “official” company t-shirt (which is what we do!).
  • Set them up with the passwords and access to the company software, platforms, etc. Nothing says “outsider” like not being able to log in to the company project management center!
  • Set up and explain Key Performance Indicators (KPIs). These are the performance metrics they’ll be evaluated against. It might be something like handling a certain number of calls in a call center, or writing a certain number of blog posts, or making a specific amount of progress on a larger project. Make sure they understand how these are measured and how they’ll be evaluated.
  • Sync up their calendar. If you have recurring team meetings or other events, let them know when and where they occur.

Onboarding is a process, not a one-time event. Someone should be checking in frequently with the new hire to head off any issues, identify any training needs, and just provide general support. It’s like being the new kid in the classroom — make sure they have someone to sit with at lunch, even if lunch is virtual!


As much information as we’ve included here, I’m sure you still have questions! Here are some thoughts that may have popped into your mind:

Is there a good or bad time of year to hire?

It depends. Most of the positions you’re likely hiring for won’t be seasonal. However, if you are looking specifically for a recent college graduate then yes, you might see more applicants if you time your search around graduation dates. Remember, though, you don’t want to start looking when you’re desperate. Start the process ahead of time!

If you have a seasonal business, then you may have peaks and valleys of hiring. But think about the costs involved in hiring a new crop of workers every year, and then training them. You may find it’s more financially advantageous to find a way to keep your employees year-round, finding some way to make use of them in the “off” season. Think outside the box. You’ll likely get a better quality employee — and not have to rehire and retrain everyone year after year.

Do you have to hire before you have the money to do so? It seems like I have to bring someone on before I have the revenue to pay for them!

There are a lot of pieces to this! There are projections — what you think you can bring in when you are fully staffed — and cash flow — what you’re dealing with on a monthly basis, including while you’re getting people trained and on board. That means you may have to hire someone before they’re paying for themselves. Even for the best employee won’t necessarily “earn their keep” from day one.

I work with my clients to reduce the amount of time you’re running in the negative due to new hires. For instance, with one client, we decided to bring on a salesperson — who generates his or her own revenue — before hiring for other support positions that don’t contribute directly to the bottom line. If you make sure you have enough revenue coming in, the rest of these hires will make a lot more sense.

Also consider what you — or your other employees — will do if you’re freed from other tasks. If you and your team can now spend more time bringing in new business because you’re not handling non-revenue-generating tasks.

I remember early in my business, I was hesitant to bring someone on as an assistant, even though I was working round the clock. My mentor told me I needed to bring in more business to generate the cash flow to finance the assistant. “It’s just going to be crazy for a while,” she told me — and it was! But knowing that I had the cash in the bank to pay that person for a set period of time gave me a huge level of comfort. And eventually, it did even out.

What if I go through this whole process and no one applies? Or the applicants are lousy?

Honestly, if you advertise the position as instructed above, it would be super-rare to get NO applicants! But if that does happen, chances are there’s something amiss with the process, so we’d move into Troubleshooting 101:

  • Simplify the process. Do you make your prospective applicants jump through too many hoops to even apply for your opening?
  • Look at the description. Is it well-written and compelling? Are you asking for too much (e.g., someone who can handle your bookkeeping, do customer service, design your logo, and install your new bathroom sink?)
  • Test the process. Sometimes the smallest thing — like a broken link or typo in your email address — can make it impossible for anyone to apply! Give the whole process a test-run.
  • Make sure you’re posting in all places listed. Sometimes you think you’ve “posted” your opening when you’ve emailed a few people. That’s not enough — go through the whole list above.
  • Check your pay range. If you include the pay range in your ad, double-check that it’s reasonable for the job, responsibilities, and skills you’re looking for. (I actually prefer NOT listing the salary for this very reason.)

What if no one meets my standards? Is it possible I’m asking for too much?

Being picky and being a total jerk are different things! Standards are good. But there’s a balance between finding the “perfect” person and how quickly you need to hire. (You can be too picky. You can take so long that your top candidate — who is an “A” player after all — finds another job!)

If you are not finding “the one” (or “the two,” as I explain above), take a look at why you are rejecting people.

  • Is it because you didn’t like their tie, or because you doubt they have the ability to perform the job?
  • Are you having trouble finding anyone in your geographic area who has the skills you want? (If so, maybe you can expand your hunt to other areas, or offer to train the right person)

Another thing you can do is to define an “A+” player. Have you had people close to that, that you rejected? Or did no one even come close?

You can also get feedback from others. Check in with your network, mentor, coach — ask them if you’re being unreasonable in what you’re looking for. And then LISTEN to them if they say you’re expecting -Mr./Ms. Right? for $9/hour.

What do you think about hiring family?

I?ve actually tried this. In my experience, you have to be really careful about hiring family. If you have to let someone go, or talk to them about their performance, it can make for an uncomfortable Thanksgiving dinner table! Although I do know people who have navigated that minefield successfully, I?d recommend avoiding it.

What do you think about hiring internationally?

It’s an interesting concept. A lot of people are drawn to it because it seems like a great way to reduce your costs. And yes, while it’s typically less expensive to hire someone overseas (particularly in Asia), there are drawbacks?

  • Language barriers — if it’s a front-facing role like phone sales or customer service, language might be an issue.
  • Time zones — don’t underestimate the challenges associated with working with a team around the world — literally. It can be tough to get everyone together at a convenient time for team meetings, plus if you need something immediately, you may have to wait 12 hours before they’re in the office. This can be really frustrating!
  • Cultural differences — as much as we have a “global economy” of sorts, there are marked differences between how people receive instructions, respond to direction, and interact with their employers.

Hiring internationally can work. There are pluses and minuses – just know what you’re getting into!

I’m worried I’ll bring someone on and then business will dry up and I won’t be able to pay them. Help!

Welcome to the wonderful world of business ownership!

Honestly, that is a valid concern. When you are bringing people onboard, you have a responsibility to them. But you know what? This situation happens every single day and businesses let people go. It’s not something you want to have happen, and I don’t want you to enter into hiring people without giving it some serious thought (which is the purpose of this guide!). But it does happen, and life goes on. It sucks, but that’s a business reality.

At the same time, though, I love that hiring someone will move you outside your comfort zone. So much of building a successful business involves taking calculated risks, so this is a great way for you to grow.

That being said, there are a ton of things you can do so you don’t find yourself in this situation:

  • Run the numbers. Know what your cash flow and projections look like, so you are hiring the right people at the right time.
  • Create contingency plans to pre-empt the need to let anyone go. Set yourself up so you don’t have to deal with that. That means doing stuff like getting a line of credit (you don’t have to use it, but it’s great to have when you need it!), having at least one month’s operating costs in the bank in cash form, and otherwise preparing for the inevitable ups and downs of business.

Bottom line: You are going to make a best-faith effort to take care of your business and your employees. No one can ask for more than that.

I need at least two people in the same role, maybe more. Should I hire them both at once?

Why wouldn’t you?? Hire them both at once, and train them both at once. The exception would be if there’s a cash flow issue. If you can’t afford to bring them both on at once, then space them out and have one train the other. But if you can, just do it once!

How do I know my new hire is doing what they are supposed to do?

Track them! Hubstaff is the system I use for tracking people remotely. It actually takes screenshots and monitors activity levels while tracking time, so I can see what people are really doing.

I’m actually a big believer in Key Performance Indicators — “quantifiable measures used to evaluate the success of an organization, employee, etc., in meeting objectives for performance.” KPIs let you and your employees know EXACTLY how you’re going to be rating them, when. (You can find out more about KPIs here: and here:

Another method is to ask your employee to prep reports at the end of the day, letting you know what they did and how long it took. Then you can review the list with them and help direct them.

You can also use project management platforms (Asana, IDoneThis and Basecamp, for example) to keep up on what your entire team is doing.

In short, there’s no excuse for not knowing what your employees are up to. Start by ASKING!

What do you think about hiring interns or college students part-time?

This is one of those ideas that sounds great in concept, but can often be more effort than it’s worth. People think they can get a few part-time interns and pay them slave wages (or maybe not at all if they’re getting college credit!) and then you get a ton of work done.


Let’s say they’re great employees. You can only have them part-time, and only for a limited timeframe. You get them all trained up and then they head off for greener pastures!

Or? they’re not so great and need a ton of supervision, so you find yourself spending your time (or your team’s time) monitoring, managing, and supervising them.

There are also legal aspects that may make hiring interns even more difficult (you know what I’m going to say — ask your attorney!).

I’d rather see you invest your time in hiring a permanent employee, rather than trying to save a few bucks by bringing on interns.

HOWEVER? (did you sense a “but” coming?) there can be circumstances when interns can be a great help. If you need several people (like for a specific project, live event, etc.) for a short period of time (a few weeks or so), and the required skill level is very low, having a crew of enthusiastic college students can be awesome! Just be prepared for some hand-holding.

I blew it! Despite my best efforts, someone made it through the hiring process and I already know it was a mistake. What do I do???

First off, this happens. Don’t beat yourself up too much. But don’t compound that initial mistake by keeping them on any longer. Get rid of them as soon as you recognize it was a mistake.

Millionaire Nathan Hirsch says, ?If you hire someone and in the first hour, all these red flags come up and they?re not who they said they are, or they?re not learning quick enough, or they?re not as good past people you?ve hired, end it. I understand it might be tough to fire someone after you?ve just hired them, but it?s gonna get so bad down the line if you just let it keep going, and going, and going, and then have to fire them later.?

Nathan says that he once hired a sales guy who seemed great, but they forgot to check his spelling and grammar. In the first three days, they knew it was a big problem. ?We had to terminate him right there,? he says.

It was awful, but keeping him on when it?s not a good fit isn?t fair to him or to your team. Let him go, and move on.


There are over 100 articles and posts on hiring on the Eventual Millionaire website. Check them out!


Traction by Gino Wackman (recommended by Doug Kisgen)
Who by Geoff Smart
Topgrading by Dr. Brad Smart (Free PDF of ?Topgrading Lite? here.)


DISC Assessment
Values Assessment
Kolbe A Asessment ($49.95)
Culture Index

Ideas For Interviewing:

The Topgrading book (and ?Topgrading Lite? PDF) has terrific ideas for digging deep in the interviewing process. See above for links.

This article from Hubspot has a great list to get you started, too.


Now that you have some specific guidelines for finding your next great hire, you have one more assignment?

Answer this question (really!):

?What is one action you can take right now, today, to move you closer to building your team of A players??

(If you don?t know how to answer that, go back and re-read section 1!).

As an interviewer, I always ask my millionaires a variation of that same question at the end of each and every interview.

And as a coach, I always have my clients commit to ?active actions? — steps that push them outside their comfort zone and on their way to building their million-dollar business.

So I?m asking you to commit as well.

You probably have at least a few ideas. But you probably also have at least a few excuses?

?Well, I?ll order those books Jaime suggested in the ?Resource? section. After I read them (in five or six months) maybe then I?ll start thinking about hiring someone??


?I?ll wait until my finances smooth out and I can better predict how much I?ll bring in this year?? (when will that be? December 29th?)


?I?m not sure I have enough work to hire someone NOW. My team and I can just stretch a bit to keep it going?? (yeah, I?m sure your current team LOVES those 15-hour work days!)


Remember in the introduction when I said that one of the main hiring differences between millionaires and others is that they don?t hesitate? It?s true. They willingly put themselves outside their comfort zones, over and over again.

I know this is scary. But you?re not doing it alone. And by pushing yourself to build your team, you?re making huge steps toward your goal of a million.

In fact, real estate superstar Gary Keller (and co-author of NY Times bestseller ?The One Thing?) told me, ?You?re only five hires away from a million dollars.?

FIVE ?A? HIRES. That?s all it takes.

So get started — and know that I?m here for you. There?s a TON of other info on my blog to help you get there.

I think you?re utterly amazing!


Jaime Masters

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Hi Iā€™m Jaime. Each and every week I bring you the top business advice from the people who know best.

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