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Inside The Office Management

The Art of Hiring: When to Start and How to Begin

If you don't know where to find the first member of your staff, we've got you covered.

If you’ve been running a solo operation for a while, the idea of hiring your first employee may feel overwhelming. Can you really trust someone else to handle the work you do every day? How will you know if you’ve found the ‘right match’ to join your business? And what should you even be looking for in a potential candidate?

Worry no more! I asked female entrepreneurs the same questions to gather their direct advice on the art of hiring and recruiting. We discussed when they first made the choice to hire, how they narrowed down the recruits and what qualities made their choice a perfect fit.

Let’s get hiring!

When did you decide that it was time to recruit?

Meg Marrs, Founder, K9 of Mine

I knew I had to look into hiring when I just felt constantly overwhelmed every day. I wasn’t responding to important emails and even missed out on some potentially powerful connections because I didn’t have the bandwidth to do it all. Many days, it felt like I was just putting out fires, with no time actually dedicated to helping the business grow. That’s when I realized it was time!

I started looking to hire about three years after starting the business, but I wish I had done it sooner.

Valentina Dragomir, Owner & Founder, PsihoSensus Therapy and PsihoSensus Academy

I knew it was time to recruit when I increasingly felt overwhelmed by the amount of work and areas I was managing on my own: appointments and client onboarding, invoicing, emails and phone calls. Also, I knew that a different person could do this better than me full-time. This way, I would be able to focus on the things I did best—therapy.

Linda Thompson, Founder, Notta.Ai

I had a solo business until I realized that I couldn’t handle everything on my own. I decided to recruit two employees: one to help me with marketing, and the other to handle customer relations. This was just eight months into the business. I found myself spending most of my time on customer relations and marketing, which left the real work in shambles.

Jenna Biancavilla, Founder, Owner & Financial Expert, Pearl Capital Management

For the first three years, I outsourced many jobs to third-party B2B partners. This can greatly leverage your hiring capabilities and ensure that you find a true expert for the task. A simple example of this is using a third-party lawyer/legal company instead of hiring in-house counsel, but it can also be a third-party marketing expert or bookkeeper.

It wasn’t until my third year of business that I hired my first employee: a personal assistant. I knew the power of delegation, but my frugal scarcity mindset struggled with the non-income producing hire and the salary and training time that comes with it.

In hindsight, I should have hired an assistant on day one of opening my business. After ripping off the band-aid of the first hire, I am much quicker to hire for all of my business ventures.

Alice Li, Owner & CEO, First Day

While hiring your first employee, your needs are going to differ. But there are some key pointers you should keep in mind:

1) Make sure that the cost of hiring doesn’t outweigh the revenue they would bring in. If it does, hold off on hiring just a bit longer.

2) When you’re certain that you have enough extra workload to keep a full-time employee busy throughout the day, then it’s okay to hire them. Otherwise, consider hiring a freelancer.

3) Don’t compromise on the quality of the service you provide. If you start getting customer complaints or if the quality of your product/service starts deteriorating, definitely hire an employee as soon as possible.

How did you decide on a specific candidate?

Meg Marrs, Founder, K9 of Mine

I used Upwork to collect potential candidates and made sure to also have Zoom calls with the top three potential employees I selected. I knew right away who I wanted to hire once we jumped on a Zoom call. For me, personality and energy sync is really important. With remote work, you really want to have people on your team who you can trust. My now-employee and I really hit it off immediately.

I truly enjoyed just chatting with him and got the sense he was a very authentic, trustworthy person. He’s been my editor for several years now, and our business could never have gotten to where it is today without him!

Having a Zoom call or phone call is really pivotal, even if it can feel intimidating. It gives you a much better sense of who the candidate is.

Sawsan Abublan, Co-Founder & CEO, Shawarma Press

I decided on candidates after comparing their qualifications and interviews with other candidates applying for the same position. It helped to rank applicants during the interviewing process. For example, after interviewing someone, I would review their qualifications, think about the interview and assign them a ranking. When all the interviews were completed for a certain position, I had applicants ranked 1-50 and automatically knew those I wanted to contact first.

Samantha Myers, Co-Owner, Let’s Dress Up

Finding the right person is challenging. As a kids’ business, we need someone energetic and fun, but who is also professional and understands that we are running a business. Reliability is a big one for us. I am always very upfront with candidates as far as our needs and our expectations, what the job is and what it is NOT. I don’t like surprises, and I try to be totally transparent throughout the interview process. It’s also helpful to have people come into the shop so they can really see it in action.

My number one piece of advice is to trust your gut when it comes to deciding on the person. People can say all the right things, but if you don’t feel it’s sincere or if their actions tell you something different, don’t be afraid to move on. Start with your network and ask for referrals. It is definitely a difficult time, so realize it may take longer than you like, but it can be done.

What qualities did you look for in a candidate?

Valentina Dragomir, Owner & Founder, PsihoSensus Therapy and PsihoSensus Academy

When I hired a secretary for my therapy place, I looked for someone friendly and personable. I also looked for someone organized and efficient to manage the appointment calendar. Excellent communication skills were a must, as the secretary is the primary point of contact for my patients and their families. Another important quality was a strong attention to detail to ensure that all paperwork is completed correctly and filed in a timely manner.

Veronica Moya, CEO & Founder, Wedding Packages NYC

Interviewing candidates can be very tricky. It takes practice. Practice to figure out who is a fraud and who is not. Everybody looks great on paper, and most people interviewed well. But I hired a few employees who turned out to be a total disappointment, even though they had all the right credentials and education. At the time, I was focusing on people who had previous experience in event management and wedding planning.

Finally, I picked someone who had NO experience in our field, but she had been with her previous company for over 15 years. She was loyal, hardworking and willing to learn something new.

In conclusion, I would recommend going with someone who shows integrity, discipline, and common sense. You can always teach the tricks of the trade, but you can’t teach good judgment.

Marina Vaamonde, Owner & Founder, HouseCashin

I have three priorities when hiring. One: the applicant must be smarter than me. As a CEO, my job is to hire the best people in real estate and have them do the work for me while I delegate and manage the company’s long-term direction. If I’m not hiring people who are smarter than me, then I end up doing the work.

Second, I don’t have the time to micromanage employees. Applicants have to be self-starters and independent workers that don’t need to wait for me to give them instructions on every single thing to do. Lastly, given that I own a small business, everybody has to be willing to wear multiple hats. I don’t like hiring people that only do exactly what’s stipulated on their contracts and aren’t willing to roll up their sleeves and help their colleagues when needed.

Valnea Skansi, CEO, Brick and Bytes

After some careful consideration, I realized that the ideal candidate would be someone who was both coachable and excited about what we were building. From my experience in managing a team in a corporation, I’ve learned to appreciate smart lazy—that is, someone who could find creative ways to streamline and automate certain tasks.

Finally, given that my company was still quite small at the time, it was important to me that I find an individual with whom I would feel a good personal fit and be able to communicate easily on a regular basis. I hired an entry-level employee, so technical skills were secondary. However, I valued all of their previous experience. They’ve been an invaluable asset and have helped us to grow our business.

Sawsan Abublan, Co-Founder & CEO, Shawarma Press

The first thing I looked for was experience. If someone had previous experience either managing or working in a fast-casual restaurant, this was always a plus. However, it was more important if an applicant seemed willing to learn and wanted the job. I believe that enthusiasm and having the right attitude are both just as important as having experience in many cases. (Of course, for more skilled positions such as chefs, managers, or professional positions such as accountants, it’s imperative to hire someone who is qualified).

Overall, I look for applicants who I believe will work well with others, be a part of the team and look forward to coming to work every day. That’s priceless!


If you want to start with finding an assistant, read four tips to find the best candidate.

About the author

Laura Grant

As Managing Editor of Lioness, Laura Grant works with the editorial team and a slew of freelancers and regular contributors to produce a publication that offers equal parts inspiration and information. Laura is a graduate of Western New England University with a bachelor’s degree in English Literature and a master's degree in Communications. She spent her undergraduate term developing her writing and communication skills through internships, tutoring and student media involvement. Her goal is to publish a novel one day. Before joining Lioness full-time, Laura was a freelancer herself and wrote many stories for the magazine.

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