For years, I wanted to hire an assistant, but I was petrified.
I didn’t know what to expect, how to get started, how to find someone worth hiring, how to go about hiring them, or what to do with them once I hired them.
Solving all of these problems could fill a small book. Today I want to walk you through the system I built to find applicants, automate 95% of the process, and find my dream employee.
Hiring An Employee Is Like Leveling Up Your Business
When you hire an employee, you’ll discover that you have these amazing new powers and that you’ll be facing huge, new challenges.
No joke: I view hiring a part-time employee as THE level up for my business this year — and as a point of growth for me as a business owner.
When I hired my first (part-time, contractor employee), I had to confront my personal fears, increase my business’s expenses, and invest time in training someone.
It took over two years of thinking before I finally pulled the trigger and tried an employee.
How To Hire Your Employee
Today, I’m going to walk you through the 95% automated system that I built. I’m going to teach you how to hire a first, part-time employee for your business.
- Writing a Job Ad — the system I used to focus on the benefits to them, instead of a traditional job ad
- The 95% Automated Application System that lets me accept applications, qualify candidates, and be hands-off until I decide we’re ready to meet
- Interview Questions — what I ask and what you can ask
- Test Projects and why they make more sense than (a) asking someone to work for free or (b) hiring off of just a resume and an interview
In this article, you and I will walk through:
- How you can decide if you’re ready to hire a part-time employee for your business
- The specific steps to take before you post your application and start getting applications
- How to set up a 95% automated process to manage your employee applications
- The exact tools that you’ll be using (and the steps to take) to set this system up
You’ll also get:
- Samples of my email templates
- The actual job ad I used to find (and hire!) my employee
- The application and interview questions I asked
- The test project I sent to high-quality candidates
— Zack Gilbert (@zackgilbert) May 11, 2015
Hiring, Administrative, and Financial Notes
All of the employees I hire are part-time contractors. That way, I don’t have to worry about insurance/taxes/all that fun stuff.
I have all of my contractors sign a subcontractor agreement that includes an NDA and a non-compete clause. That way I’m protected if Something Terrible™ happens.
Nothing Terrible™ has ever happened, but contracts are the bedrock of a sustainable business — so I invested in my attorney reviewing and offering feedback on my subcontractor agreement.
My (95% Automated) Hiring System
I wanted to automate as much of my hiring system as possible:
- A prospect sees a job posting on Craigslist with a call to action of “Email email@example.com”.
- When they email that address, they get an automatic reply, directing them to an application form
- When they fill out the application form, I get an email that I have a new applicant to review
- If the applicant looks like a good candidate, I sent them a pre-written template with a call to action to schedule a 30-minute time for us to meet (I use calendly for that)
- At the meeting, I ask them 6-8 questions about their background and experience. I’m looking to see how conversational they are, if they’re interesting, and if I’d enjoy working with them
- If they pass, I assign them a paid test project to complete
- Finally, if I like the results of the test project, I offer them a part-time job.
Now, let’s walk through some Big Questions and the steps behind this system.
How to Decide if You’re Ready to Hire An Employee
Looking at your business, you want to answer four questions:
- Can you AFFORD to hire an employee?
- What will the employee be DOING?
- Do you have the TIME to hire an employee?
- Do you feel CONFIDENT in hiring an employee?
Cost — Can you AFFORD to hire an employee?
I advocate hiring contractors, not W2 employees. Hiring contractors reduces your cost (you won’t be paying taxes, etc.), and it also reduces your risk. (I use the terms ‘employee’ and ‘contractors’ interchangeably in the article).
If you’re hiring a contractor, you won’t need to worry about payroll taxes (and other expenses). But there are two key costs you’ll need to consider:
- Wages — How much you’ll be paying them.
- Cost of Tools — The subscriptions, tools, and resources they’ll be using.
Let’s say, for example, that you’re planning to hire someone to work, on average, 10 hours/week for your business. You’ll be paying them $15/hour. That’s a $600/month expense.
In addition to that, you have to account for the cost of any tools (e.g., SaaS subscriptions, pens, etc.) that you’ll be investing in for your employee.
You might be thinking “Kai, I’ll just share my logins with them,” but that gets messy. What if you both are using a tool at the same time? What if data gets overwritten? What if a tool tracks who did what — and you’re trying to figure out who made a change?
It’s worth the additional investment for clean data
An Example on Costs
When I hired my employee, here are the additional monthly costs that I had to spend on tools:
- Buzzstream: Upgraded to the Professional Plan, +$85/month
- Yesware: Registered an additional monthly ‘Professional’ account, +$15/month
- Freckle: For time tracking, +30/month
- ZenPayroll: adding a contractor to pay, $5/mo
- StreakCRM: Registered an additional account for collaboration, +$40/month
- Google Apps Account: For an “@kaidavis.com” email address, +$5/month
That’s an additional $180/month in monthly expenses. I’m sure I’m forgetting a few things.
Point being, there are multiple costs you will be experiencing when you hire an employee. When you’re working on making that decision, consider the additional tools (Photoshop? Google Apps? Hubspot? Salesforce?) that you’ll need to pay for them to access.
Can your business afford that? (If you can’t answer that question, you should probably start keeping a budget for your business. Go download You Need A Budget. It’s what I use for my business, and I highly recommend the program).
Tasks — What will the employee be DOING?
It’s easy to think about someone working for you. It’s hard to figure out what, exactly, they’ll be doing.
I’m a big fan of writing out Standard Operating Procedures (“SOPs”) for the repeat projects that I work on. One additional benefit of robust SOPs is that it makes it easy for you to train a new employee:
- Review this document explaining, step by step, the process to follow
- Watch me as I model the process
- Run through the steps in the document, alerting me if you run into anything that I’m not explaining well
- Together, we’ll update the document.
Time is… fleeting
If you’re planning on hiring someone to work for you for, say, 10-hours every week, you’ll want to have 15-hours of tasks set aside and documented for them.
- Start by tracking what you spend your time doing: responding to customer support requests, prospecting and qualifying individuals for outreach, etc
- Then, isolate 10- to 15-hours/week of work for that employee to handle
Why try and have more work set aside? There will be areas where your employee will be more efficient than you. I like having too much work set aside for them — and trimming down their responsibilities — than having to ‘make work.’
For every system or project you’ll be delegating, make sure you have a rough Standard Operating Procedure written out. This doesn’t have to be perfect, something like:
- Do this thing first
- Do this other thing next
- Then do this third thing
- And finally make a record of what you did in this place
is a fine starting Standard Operating Procedure. Ideally, you want to be able to hand them a rough framework that they can follow to get started, get to 70%, and use as a basis for their questions. I use Google Docs to store my SOPs.
Plan Out A Week
You’ll want to write out an example week for your employee, with time breakdowns of where you’d like them to spend their time. For my Outreach Coordinator, it looks like:
- 5 Hours Prospecting and Qualifying influencers for outreach
- 3 Hours Outreaching
- 3 Hours Managing Opportunities / Placements
- 2 Hours Email Copywriting
Writing out a weekly agenda helps you plan out what your employee will be working on. Likewise, this strategy gives your employee a clear idea of what they’ll be working on, where they’ll be focusing their time and attention, and what their priorities are.
Time — Do you have the TIME to hire an employee?
Delegating 10 hours of work? That doesn’t magically give you 10 hours of free time. At least, not at first.
As you onboard your employee, there will be questions, meetings, explanations, mistakes, and trainings to take care of.
In the first month or two, expect to spend at least as much time training your employee as you’ll be ‘freeing up’ by hiring them.
After the first month or two, as your employee becomes more familiar with your procedures and tools, they’ll be more up to speed. At that point, you’ll be spending a fraction of your time on managing the employee, but you’ll still be spending time managing them.
The woman I hired as my Outreach Coordinator — Stephanie — is an ace at what she does. But part of the ‘cost’ of hiring an employee is the time you’ll need to spend managing that employee.
For Stephanie, this is how that typically breaks down:
- A weekly two or three hour meeting to review the campaigns we’re working on, answer any questions, and co-work together (2-3 hours/week)
- Time spent in Slack answering questions (1 hour/week)
- Time spent revising documentation — and writing out new Standard Operating Procedures (1 hour/week)
Roughly, I look at it as a 2:1 ratio. For every 2 hours the employee saves me, I’m spending 1 hour on managing the employee.
I’m happy with this ratio. And, as we answer questions, revise documentation, and write more Standard Operating Procedures, we make it easier for me to train my next employee and get them up to speed quicker.
Confidence — Do you feel CONFIDENT in hiring an employee?
I struggled with this for years. I never felt confident in my ability to hire an employee.
The first (few) times you hire someone, you’ll feel overwhelmed, scared, and convinced you don’t know what you’re doing.
That’s okay. That’s normal. That’s natural. You’re doing something new. You’re pushing outside of your comfort zone. This is okay.
What’s the absolute WORST thing that would happen?
- You underestimated the amount work that you have for the employee and you reduce the amount of hours they’re working
- You fire them
That’s it. That’s the worst case scenario. Business will continue on.
You can do it. I believe in you.
On Who To Hire
You can hire Undergraduates (Juniors, Seniors), Graduate Students (1st years), Ph.D, Candidates (1st and 2nd year), and Community Members.
Which should you hire? Hard to say. There’s costs and benefits to each. Let’s walk through the options:
- Undergraduates are hungry for experience, but don’t have a lot of experience. You’ll (probably) be the first employer they have. Expect to train them on both your Standard Operating Procedure, your business procedures, and General Business Stuff™. Undergraduates are the most affordable.
- Graduate Students have some real world experience and may be looking for part-time work while they pursue their masters degree, meaning they’ll be around for 2-3 years. Upside? They’re looking for work. Downside? They’re looking for work related to their major. I like hiring 1st year graduate students in field related to the work I’m doing. Graduate students are slightly more expensive than undergraduate students.
- Ph.D. Candidates have more real world experience. They may be looking for part-time work while they pursue their Ph.D., meaning they’ll be around for 2-6 years. They may also be pursuing a GTF position, which means they have no time.
- Community Members are a great option. In the past, I’ve been gun-shy about hiring employees who aren’t students because of the “I Want To Work 40 Hours A Week” problem. That aside, community members are much more stable than students and are often interested in learning something new. Prices may vary, depending on experience.
The Steps To Success
Let’s walk through each of the parts of this system individually. Then, in the following section, I’ll show you how to put all of these parts together into an automated system.
Writing a Job Ad
You’ll want to write up a short job description to post on Craigslist and send to your local University.
Write the job description like a sales page. You are selling a specific person on the joy and reward of working with you. Focus your job description on answering these questions:
- What will they learn?
- What skills will they build?
- How will they become a better person?
- How will this set them up for future, exciting things?
Preparing a Test Project
I like having a small, paid test project for qualified candidates to tackle.
By using a paid test project, I can learn what it’s like to work with them, how they communicate, and the quality of the work and, most importantly, they get paid for their time.
I like to break my test projects into 2-4 parts. Each part touches on some of the responsibilities that they’ll be handling as part of the position.
I don’t like resumes. I like seeing actual, real work.
Preparing Interview Questions
You’ll want to prepare a few — six or so — interview questions to ask applicants when you meet with them. Here’s what I like to ask:
- What interested you in applying to this position?
- What skills would you like to gain by working in this position?
- What similar projects have you worked on in the past?
- How would you handle [common situation]?
- Walk me through how you’d manage organizing a camping trip with 6 friends. How would you prepare? What would you do? How would you stay organized?
- What’s your availability look like, week to week?
- If I tell you that I want to start next week, walk me through the next steps on your side?
Mostly, I’m checking to see if we have rapport, if they prepared for the interview, if they’re interesting to talk with, and if they’re organized.
Setting Up An Application
Within the job ad, the call to action is to email me. When they email me, I respond (automatically) with a little more information and a call to action to fill out an application form.
On the application, you’ll want to ask questions like:
- What’s your background in [industry]?
- What’s your name, email, and contact information?
- Do you have a website or blog? If so, what’s the URL?
- What are you looking to learn through this position?
(Here’s a link to my sample Application Form)
Screening, Qualifying, and Interviewing
As people apply, you’ll want to weed out people who aren’t a good fit. This is more subjective than objective.
As you look at the results coming into your spreadsheet, make note of the people who you think are good matches and reach out to them.
Writing a ‘Let’s Meet!’ Email
Once you’ve qualified your best candidates (they’re qualified, they’ve filled out the application, you’d like to meet with them), you’ll want to meet with them!
It’s valuable to prepare a template email to have on hand to send to them. I use an email like this:
Thanks so much for applying for [Position]. I’d love to schedule a time for us to meet to discuss the position and answer any questions that you have.
As a next step, choose a 30-minute time for us to meet on my calendar here: [Link to Scheduling Tool],
(I use Calendly as the scheduling tool).
When I meet with an applicant, I’m interested in learning three things:
- Did they prepare for the interview by researching me, my company, or the position?
- Are they interesting to talk with?
- Are they organized?
I’m less focused on their direct experience and skills and more interesting in verifying that they’re a person I’d enjoy working with.
If someone qualifies as a serious candidate, I send them the information on the test project and give them a timeline and due date to complete the project by.
Advertising and Promotion
Once you’ve completed all of these steps, you’re ready to promote your job description!
- Post it on your local Craigslist
- Email the career center at your local university and/or college and tell them you’re looking to hire a part-time student. Attach the job description.
- Email the specific, relevant departments at your local university and/or college. Attach the job description.
- Email your friends, family, and local network, letting them know you’re hiring, including a link to the post, and asking them to share the ad with anyone they think would be a good fit.
And, with time, people will start to email you and receive a link to fill out the application.
As people send back their responses to your test project, you’ll want to review the results:
- Did they complete the project to specification?
- Did they do a good job?
- Did they approach it in an interesting or unique way?
- Were they communicative, reaching out to ask clarifying questions?
And then you’ll want to hire the best candidate.
Setting Up The Automated System
Now, let’s walk through putting all of these pieces together to create a 95% automated application and screening process.
The Tools You’ll Be Using
- Typeform, Wufoo, or Google Forms
- Google Spreadsheet and Google Docs
- Gmail Email Templates and Canned Replies
It’s really simple to connect all of these together. Don’t worry.
Setting Up Your System
- Set up an ‘Application Form’ for an applicant on Typeform, Wufoo, or Google Forms.
- Set the form to email you when someone submits it.
- Write up a Craigslist ad / ad to send to your college career center or college departments. Here’s the ad I used when I hired my Outreach Coordinator (Craigslist Link, Text Copy).
- Write up an email template in Gmail to send to people who apply to your job. (Here’s the template I used). If you don’t use gmail, just save the template as a text file and reply to applicants with it.
- Set up a Canned Reply template in gmail, so that any email sent to the address you specify (like firstname.lastname@example.org) is automatically sent your canned reply. (Here’s a quick screen recording showing how to set this up)
- Post your ad on Craigslist. Call the career centers at your local colleges and universities and ask who you should send a paid part-time job posting that you’re looking for a student to fill. Also contact the relevant departments at your local colleges and universities (I contacted the Public Relations, Journalism, and Business / Marketing departments at the University of Oregon).
- When an individual applies, they’ll be sent your canned reply, linking them to the application form.
- When an individual fills out the application form, you’ll get an email with their responses to review.
- For the people that you think are a good match and want to interview further, send them a short email to schedule a time to meet. (I recommend using Calendly to let them pick a time to meet).
- Then, if they pass the face-to-face meeting, you’ll want to give them a small, paid test project. That way, you’ll be able to discover what it’s like to work with them, before you hire them on full time — and they’re compensated for their time. (This is the test project that I gave my applicants)
- Once you receive the results of the test project back, you can make a hire/don’t-hire decision on the candidate.
And That’s The System!
This system is how I hired my first employee and the system I’ll be using to hire my second and third employees when the time is right.
I like this system because it automates a lot of the busy parts of the hiring process. This system has helped me spend less time on the low-value parts of the hiring process (receiving and sending emails, reading applications, etc.) and more time on the high-value parts (interviewing the candidate, reviewing their test project).
If you have any questions about the hiring process, feel free to leave a question below. I promise I’ll respond to everything.