How to hire an assistant

How to Hire the Best Assistant

You’ve got 53 unopened emails in your inbox. You are behind in writing your weekly email. At some point, you’ll need to call Delta to do a name change. You haven’t posted on social media in over a week. Billy needs to be picked up from ballet lessons at 4, along with your dry cleaning, and it’s already 3:30! Maybe it’s time to hire an assistant.

Every Batman Needs a Robin

Every Sonny needs a Cher. At some point, you are going to have to hire an assistant if you want to take your travel business to the next level.

How do you know it’s time to hire an assistant?

Hiring your first assistant for your travel business is a rite of passage. It’s a rip-the-bandaid-off moment but how do you know when it’s time? 

You’ll know you are ready when you have more money than hours in a day. To be conservative, let’s say you value an hour of your time at $50 and you work an eight-hour day. That equals $400 a day. But you’ve just closed 2 bookings that will net you $8000 total.

Does it really make sense for you to stop what you are doing and decline an opportunity to meet with another set of potential clients because you have to do a grocery run? Or fold Billy’s bedsheets that have been gathering lint in the dryer for three days?

Why you won’t want to hire an assistant.

You’ll think it’s frivolous.

“What mother pays for someone to fold their laundry” will be the judgy soundtrack playing in the back of your head. Your mother-in-law had a full-time job and still did it all. What will she think? But that’s such a backward approach. 

How to hire an assistant

You have to consider the opportunity cost. Sure you could do it yourself but if you can bring in more than $50 an hour working in your zone of genius…why the hell would you waste your time trying to go all Martha Stewart on a fitted sheet when someone would be happy to do it for far less?

Just because you can, doesn’t mean you should. It’s time to hire an assistant.

Or, you’ll mistakenly think when it comes to small inconsequential yet necessary tasks…

“Oh, but it will only take me 2 minutes”

Have a serious conversation with your family members and ask them how long your minutes are? If you are anything like me…I’ll shout..” I’ll be there in just a minute!” as my family sits baking in the car waiting for me to emerge.

It’s never really just 2 minutes…now is it?

You won’t trust that an assistant will do things as well as you.

Maybe they will. Maybe they won’t. Have a moment of some serious reflection on what you can relinquish control over. Maybe what you get won’t be pure perfection, but ask yourself, is the time it saves you to focus on more pressing things worth the sacrifice?

You might even be surprised by how well others can do the tasks you hate.

You’ll be worried you won’t have enough work to delegate once you hire an assistant.

Hiring a full-time employee is scary. The last thing you want is to hire them and then have them stare at you, drumming their fingers on the desk, waiting ever so impatiently for the next task. 

That would be a heartbreak. Instead, before you post for the position, these are some steps you’ll want to take.

Steps to take before you hire an assistant

Step One – Track everything you do for a week

For the tasks that are more administrative and not inside your zone of genius, add to the growing list of things to delegate. But before you can, you’ll need to create a “how-to” tutorial to document your process.

Video is best. Save a copy in an iCloud library. This is a far more effective way than attempting to teach firsthand. It will save you from having to repeat yourself and I’m sure whoever you hire will appreciate the resource.

why you should hire an assistant and stay in your zone of genius

Step Three – Write a job description to attract the perfect assistant.

Next up, draft a job description. A job description provides clear expectations and will avoid time-consuming and awkward conversations later. 

Most employees crave job satisfaction. They want clear and measurable markers that once accomplished, they can self-assess that they’ve done a good job.

Ambiguity just leads to disappointment. When creating a job description, be as detailed as possible about the tasks they’ll be expected to complete.

A good job description should also sell your business. You don’t want to attract just anybody. You want someone who you could potentially see growing alongside you in your company. They may start out as an assistant, but someone with the right attitude can quickly become an invaluable key player later in your business.

Write a job description that will attract the most amazing candidates and not applicants who are only looking for a paycheck. Think about what might motivate the ideal candidate. Opportunities for growth and career development are a good start. 

5 Common mistakes to avoid when hiring an assistant

Mistake #1 – Hiring the wrong person because it seems easy.

Everyone knows someone who’s looking for a job. Maybe it’s your sister-in-law? Plus, you might think, if I hire Mary, then I won’t have to go through the hassle of posting the position, weeding through resumes and interviewing. Yuck.

But when it comes to hiring, the easy path is almost always fraught with thorns. Do the work and get the right fit. You’ll thank me later.

Mistake #2 – Hiring an assistant who is too much like you.

It’s normal to be attracted to people that look like you, talk like you and laugh like you. The only problem is, if they are so much like you, they’ll probably suck at the same things you do. 

In my experience, it’s a rare thing to be exceptional at sales and equally exceptional at details. I’ve seen a few unicorns who exhibit both qualities, but seriously…not many. I’m going to take a guess and suggest that if you are reading this, you are great at sales.

Be sure that whomever you hire, complements your strengths and has amazing attention to detail.

tips for hiring

Mistake #3 – Hiring an assistant before you’ve created processes and expecting them to read your mind.

Sometimes, tasks that seem so obvious to you, because you’ve done them a million times, aren’t as obvious to someone walking in off the street. I’ve interviewed probably close to a thousand people and I have yet to come across anyone who resembled the Amazing Kreskin.

Mistake #4 – Underpaying

You may be tempted to cut corners when it comes to compensation. Usually, around the time you decide to make your first hire, money is still tight. I would rather you think abundantly and focus on how much more money you’ll be able to bring in, once the right hire is in place.

How to hire an assistant

Creating an attractive compensation package doesn’t just come down to dollars and cents, however. Get creative. What other benefits could you include to make the position more attractive? What about offering flexible work hours? Consider paying for results vs. time. 

Mistake #5 – Hiring for Potential

I always prided myself on being able to find diamonds in the rough. Mentoring talent was the favourite part of my job working for large travel companies.

But as a solopreneur running a lean travel business, you simply won’t have time to train someone from scratch…no matter how eager they seem and how much you like them. Never hire for potential. You’ll want to look for someone who can hit the ground running.

5 Tips to help you narrow down the candidates

If you’ve done your job right and you’ve written an enticing job posting, you may find you get quite a lot of applicants. Now what? You’ll be thinking…I don’t have time for this. Here are five tips to help you weed through the pile.

  • Eliminate anyone who didn’t provide a cover letter
  • Remove anyone who didn’t bother running their application through a grammar and spell checker
  • Do a quick social media check for any obvious red flags

Just those three steps alone will surprisingly shrink the pile to something more manageable.

  • Give each applicant a similar task to perform. I think researching an itinerary makes for a perfect task. You’ll want to give them enough guidance to get them on their way but also be intentionally vague in one small area of the assignment so you get an idea of how well they think on their feet. As a small business owner, this is an invaluable skill to have in your team. 
  • The last step, give them detailed instructions on how to submit the assignment along with a feasible timeline.
How to hire an assistant
  • Cross out anybody who didn’t follow instructions and/or meet the deadline. 

After all of that, you’ll be lucky if you are left with three viable candidates to interview. And if you don’t have at least three, I’d probably repost the job description. You can’t really afford to make a bad hire so take your time until you find the right fit.

But take comfort in knowing the right fit is out there and when you find them, you’ll know it, immediately.

The good news is when it comes to hiring an assistant, there is a lot of amazing talent in the travel industry and because this position will be remote, the world is your talent pool.

Good luck.

I’d love to get your feedback. Please leave a comment below.


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