The When and How of Hiring an Assistant

Most people wait too long to hire an assistant out of fear that he or she will not be able to pay the assistant. Don’t wait! If you are reading this article, it’s likely you need one – and badly. So, here’s the brutal honesty of when is the right time to hire an assistant.

It’s time to hire an assistant or some form of help when you:

  • feel like your business is running you – and you are NOT running your business;
  • feel overwhelmed to the point of paralysis, except in the day-to-day where your to-do list is a mile long;
  • find yourself “dropping the ball” on more occasions than you would like to admit;
  • feel your business is sucking the life out of you and the joy for your business is a faint memory.


If you recognize yourself in any of the above statements, here is my advice on how to proceed with actually hiring someone.


First and foremost … do NOT hire the friend/neighbor/teacher that has expressed an interest in working for you. Or the person that is out of work and looking for something to do. In other words, do not stumble upon a person who needs/wants the work and then create the job for them. Instead, create the job and then find the right person.


Second – establish an intention and BELIEVE! I have not yet met an entrepreneur that excels at every single role in his or her business. We are not meant to do it alone. But I have also found that as human beings, we have a tendency to assume that if I hate doing something, so does everybody else in the world. For example, you might be a person who LOVES selling – that’s why you got in the business in the first place. But tasks like putting the client details into your CRM, invoicing the client, booking dinner reservations, etc make you want to pull your hair out. Guess what? For every single task you avoid like the plague, there IS someone who LOVES doing that. I promise you. So set the intention that you are going to find the most perfect (in skills and personality) person to fill this role with ease and grace.


Third – create the job description. Begin by categorizing every task on your plate into 1 of 4 categories that mirror the sales cycle:


– Phase 1 – The List Building Phase –
This phase includes all of your marketing activities for list-building. It’s the activities involved with putting on bridal shows, networking, speaking engagements, Facebook ads, blogging, etc, etc, etc. Anything on your list with respect to list building marketing activities, are Phase 1.


– Phase 2 – The Selling Phase –

This phase begins the moment you receive an inquiry, whether it’s by phone, email, or text message, and continues until you take a deposit on their itinerary. So this phase includes all the tasks involved in “closing the sale.” From itinerary creation, to the getting to know you phone call, to researching, to presenting quotes, to getting client details, etc.


– Phase 3 – The Service Delivery Phase –

This phase begins the moment you take deposit and continues until the day the client returns from their travel. This is the phase where you have the greatest opportunity to establish your value relative to a booking engine or booking direct with the supplier. This is the phase where you are preparing your client for their upcoming travel and enhancing the skeleton of their itinerary. So tasks like putting together great travel documents, making dinner reservations, spa appointments, notifying them of necessary travel documents, etc are included in Phase 3.


– Phase 4 – The Relationship Building Phase –

This phase begins the moment your client returns from the travel you just planned and continues until he or she reaches out to you again with an inquiry, completing the circle. Tasks in this phase include things like the welcome home phone call, the 12-month keep in touch campaign, handling Facebook posts and engagement, etc.


Once you have all your tasks categorized by phase, decide which tasks you enjoy and are great at, and look for the tasks you really don’t like and/or are not good at. It’s pretty common for travel entrepreneurs to keep Phase 2, sometimes Phase 1 and then delegate Phases 3 and 4. But everybody is different. Create a list and start writing a job description. Get clear on skills needed as well as certain requirements, like knowing excel or how to work your CRM.   Google job descriptions to give yourself a format to follow.


Fourth – Post your Job Description. You can post it in places like Craig’s list or your local Chamber of Commerce. You might want to consider posting it in your local newspaper. We have found luck in posting our job descriptions in private Facebook Forums where we know there are a lot of well educated, stay-at-home moms who were once professional and now have kids in school full time so they are looking to slowly join the workforce again. But be sure you post it somewhere that you feel your ideal employee will be hanging out and looking. It might be that a young, college kid is likely to have the social media skills for which you are looking, which then means posting in the college job postings would be a good option.


Fifth – Review the resumes and interview. Do not just jump on someone’s resume and hire them. Take the time to interview your prospects. Ask questions that will have them demonstrate the skills you are looking for. For example, if you want someone to help you with customer service type tasks, ask your prospect to describe an example in a prior work environment where she or he demonstrated great customer service skills.


Sixth – Hire.


And there you have it! It’s really a lot more simple than it seems. And you will feel like a new person when you have your new person onboard, doing all the tasks you can’t stand. I leave you with this – you are not meant to do it all alone.