The Entrepreneur’s Ultimate Guide to Hiring Your First Employee


We get it – your business is like your baby; you’ve grown it from nothing and now you want to protect it. But hiring your first employee is a really exciting time and speaks to how well you’re running the place! Take a moment to pat yourself on the back, and then get ready to build a sturdy hiring process with us and ensure you find someone who’s going to treat your baby as well as you do.

If a job posting falls in a forest, does it still get applications? It’s one of life’s unanswerable questions… until now. You need to cast a big net to find the perfect employee. People need to hear your call!  “We generally post to LinkedIn first. When you post, Indeed – a sort of catch-all from different job sites – picks it up also” says Therese Van Es, Vice President of People and Culture for Buckland and longtime small business owner. You do pay a fee to post on the network, but she assures us it’s worth it. “You get the passive jobseekers as well… people who are happy and good at their current jobs. If a job comes up on their feed that looks intriguing, they’ll often casually apply. That’s where we get the best candidates.”

“I’m in a small town, so posting locally is also very helpful” she adds. Still, Therese is in favor of digital posting, noting that newspapers and other print postings don’t work as well as they did just a few years ago.

Almost 40% of all job applications and resumes have inflated facts. It’s your job to cut through it all and get to the heart of who they really are – if they’ll be a good fit for your company, will do a good job, and if you could stand being on a 5-hour flight with them.

“There are questions you can’t ask” Therese explains. A candidate is entitled to keep some details private. Things like race, religion, gender, sexual orientation, national origin and age. You can find the full list of regulations through the Equal Employment Opportunity Commission. Beyond that, dig in.

“The best piece of advice I can offer is to ask questions about past performance rather than the future.” Instead of asking how someone would respond to a made-up situation, ask them the last time they handled a similar scenario. “It gives [the candidate] less room to concoct an ideal and you’ll get an answer more authentic to their professional behavior.”

Everyone has their own interview style. Some stick to the job and how well they could do it, others are more lenient on skill level if they think they’ll be a good cultural fit. Here’s a few questions that industry big wigs ask to uncover personality:

  • What do you think about when you’re alone in your car? (Glassdoor)
  • Describe the color yellow to somebody who is blind. (Glassdoor)
  • I ask them what the last costume they wore was (Oprah… because who doesn’t want to steal Oprah’s interview questions?)

Oh yeah, and don’t forget to check their references.

Every company has their own onboarding process. At Hubba, we make sure the new hire feels like they’re a part of the gang right off the bat. We send out a company-wide email introducing and welcoming the new team member, decorate their desk, give them swag, and ask them what their party trick is at their first big meeting. But we also make sure we have our administrative duck in a row.

Therese’s company has specific requirements for training. Maybe they need a SmartServe license; maybe WHMIS training. “I send them a package with everything they need to complete before their first day at work.”

There are also legal requirements in the US that you need to comply with as a small business owner with an employee. In accordance with the Department of Labor, you need to keep track of:

  • Employee’s full name and social security number.
  • Address, including zip code.
  • Birth date, if younger than 19.
  • Sex and occupation.
  • Time and day of week when employee’s workweek begins.
  • Hours worked each day.
  • Total hours worked each workweek.
  • Basis on which employee’s wages are paid (e.g., “$9 per hour”, “$440 a week”, “piecework”)
  • Regular hourly pay rate.
  • Total daily or weekly straight-time earnings.
  • Total overtime earnings for the workweek.
  • All additions to or deductions from the employee’s wages.
  • Total wages paid each pay period.
  • Date of payment and the pay period covered by the payment.

You can get more information on their website.


What did our users have to say about hiring their first employee?

“I require people who apply to send in cover letters, or their resume may not be reviewed. We are a creative business with a unique name, so cover letters help me recognize those who’re creative and have taken the time to look into [what we do]. I sometimes don’t even look at resumes until the day they come in to interview. We train for all of the jobs we hire for, so experience isn’t much of a concern for me.” – Andi from Whiskey, Ink & Lace