An executive assistant can be a godsend to your landscape or lawn care company if you hire the right fit and define their role well.
One big question is when you should add an assistant. This is mostly a case-by-case situation. Taylor Milliken, owner and president of Milosi, based in Hendersonville, Tennessee, says it depends on the company’s structure and org chart as well as the role of the executive assistant (EA). He hired his EA in the past 12 months when his company was at $13 million.
“I would do a calendar review (audit) of everything you are doing and see if those are the most valuable things for your time,” Milliken says. “For instance, what are you doing that someone else could do so that you can work on the business and not in it. This could potentially help them take their company to the next level.”
Justin White, owner of K&D Landscaping, Inc., based in Watsonville, California, hired his assistant in spring 2022. He had worked as a CEO for almost 10 years before bringing her on.
“Immediately within the first month, I wished I did it sooner,” White says. “I would just say to those who are on the fence, one of the key things that successful CEOs have of growing companies is they have an executive assistant.”
White says that any company can benefit from an executive assistant, whether they’re a $1 million company or a $10 million company as long as the owner or CEO is willing to use the new time they get back to further benefit the business.
“If you’re looking to take more time off and get more vacations and spend more time with your family, I would say you need to be around $5 million minimum, but if you’re looking to take that new time you have and reinvest it in the business, then you can hire an executive assistant when you’re less or around a million in revenue,” White says.
White says once you get over $10 million, you really need to hire an assistant. Otherwise, you become one yourself.
What An Assistant Can Do
Make sure you have a clear job description for this role, as all executive assistants are different, but their main role is making your job easier.
White notes that you get to decide what exactly you want your assistant to help with. He says a good analogy is walking his dog – technically, anyone could do this, but it’s something he enjoys and benefits from. Likewise, you don’t have to give up a low-skill task, if it’s one you enjoy and it benefits the organization in a healthy way.
White’s assistant’s main job is to ensure he is focused and has an awareness of the right things in the company. He says she serves as a canary in the coal mine for when things are getting off track.
“The other part is email and calendar management is a huge one,” White says. “Just helping, even if it’s not totally managing it, but when I need an email sent, I can call her if I’m in a hurry or text her and tell her, ‘Hey, I need you to send an email and so and so’ and I know that it’s going look super professional and be well polished. Versus if I’m trying to get on a plane or I’m walking into a meeting, I don’t really have time to create an email that’s professional and double check the spelling and everything. I know that she’s going to handle it.”
Milliken says that he has a daily call with his assistant where they run through his day before and day of and what he didn’t accomplish or anything that needs more attention.
“If it is important, it lands on my calendar even for ‘thinking time,’” Milliken says. “She looks for patterns in things I do to help me automate or streamline these items. She helps me anticipate current and future needs.”
Milliken’s assistant also helps him in his personal life with planning date nights, lunches with kids at school, connecting with friends, training time for his health and rental property items.
“We sit down and look at the most important things for the month, quarter, year and build my calendar around my non-negotiables,” Milliken says. “She also is a voice of reason for me so that I am not steering away from what I said was important for my professional and personal life.”
White notes that his EA also serves as his R&D department as she is able to learn about new opportunities and technology and report back to the leadership team.
What to Look for in an Assistant
White suggests finding an assistant who has strengths in areas where you are weak.
“I don’t think there’s a certain type of executive assistant that is a mold,” White says. “If an owner is a really well-organized person, and they have everything in order, but they really struggle with conversations and some of these other things, then you want someone who can help complement you in those areas.”
As for industry experience, White says it’s almost better for your EA not to have any because they can easily get pulled into solving day-to-day problems.
“You want someone who is professional because they are representing the owner or CEO’s office,” White says. “You want someone who’s going to be neutral with your team. You don’t want someone who’s going to need a lot of a lot of compliments or recognition because ultimately being the executive assistant is doing all the hard work and getting none of the recognition for it. It’s a really hard position to emotionally play.”
Milliken adds other traits to look for in an executive assistant, include:
- Well-organized
- Able to multitask
- Empathetic
- Supportive
- Self-starter
- Problem-solver
- Consistent
- Strategic
- Great communicator
- Good listener
“If you’re continuing to grow and you want to be the best CEO of your company, you owe it to your employees, you owe it to your company and your board and your owners to hire an executive assistant,” White says. “If you’re not doing it, I think it’s a selfish move. Even though you think by hiring, it’s selfish, it’s the opposite. In short, I would say just do it.”
