Should You Hire an Assistant?


Being a CEO for a small business isn’t easy. Madeleine Costa, Founder and CEO of Succeeding Small (a small business digital marketing firm located in Colorado Springs) knows the stress that comes with being a CEO. At the beginning of her business, she remembers, “it was just me and a couple of other people who were actually doing the work. And I was actually working with a business coach at the time. And I had a monster to-do list. I mean, it was a mile long. I was already working 80 hours a week. I hadn’t taken a weekend off in a decade. Like it was, I was so exhausted and burnt out, but I still had a million things to do and I didn’t have enough time to do them.” That is when Madeleine hired her administrative assistant at the time, Madison Bowers. 


Madison, now Operations Manager at Succeeding Small has extensive experience working with CEOs and Presidents of companies in the past. She and Madeleine have also known each other for almost a decade now, which aided in their professional relationship. 


Madeleine and Madison discuss the keys to building a healthy work relationship with your assistant and how they can help you have a more work-life balance. By the end of this episode, you might be considering hiring an assistant for yourself, or asking yourself, ‘what would I want in an assistant?’ 

Find someone who complements your skill set

“I remember the day I cleared out your inbox and you were so excited. I was like, oh, wait, if that gets you excited, wait until you see what else I can do,” Madison recalls her first few weeks being Madeleine’s assistant. “I think it’s just one of those that like our skill sets are very, very different. So it’s cool to see how we can complement each other in that way.”


Finding an assistant that complements your skill set and work language is crucial when finding an assistant for yourself. For example, you want to find someone who likes spreadsheets if you hate them; enjoys answering your emails when it feels too overwhelming to you; someone who can do all those things on your to-do list that has been weighing you down or making you feel burnt out. 


Madeleine explains how liberating it was in her personal and professional life when hiring Madison as her assistant, “The fact that you actually enjoy that stuff, like just blew my mind in terms of this woman likes checklists, she likes systems and processes. Like she actually enjoys doing these things and I hate them. So that was just so funny to me to have somebody who really just complemented my skills, it in a way, and you thrive in, in your space and hiring you allowed to allowed me to really thrive in my own space and what I am best at. So I think that was just really eye-opening for me. And you have just become such an influential person in, in our company and just allowing different people to play to their strengths. So that was just, that was something so interesting to me.”

Madison also discusses what she defines an administrative assistant to be, “I’m not the vision caster. I don’t necessarily pick the final destination, but I can tell you how to get there… I don’t want to be in charge but I have no problem taking charge.

As a small business owner, where do i start?

 “The place to start, especially if you’re a business owner who is, you know, kind of in the place you were in Madeleine when you started off just looking for an extra set of hands, I think honestly you can go with a virtual assistant or an executive assistant of sorts because a lot of times they have a very diverse skillset. Um, when I was, and, and a big quality that I pride myself on, and that I’ve seen in all of the executive assistants, I’ve had the pleasure of working with is they, they are kind of go-getters and figure it outers. They are just good at rolling up their sleeves and being like, no, I don’t know how to do that, but I’ll figure it out and like, or I’ll find somebody who can,” Madison expresses about where to start when looking for an assistant. 


Madison goes on to say that there are different things to discover when looking to hire an assistant. Do you want a virtual assistant? Someone who can transcribe videos and answer your emails for you. Or are you looking for someone who is going to be an extra set of hands in your day-to-day schedule? 


As a CEO you want to find someone who can do the things that you don’t have time for or you shouldn’t be doing in the position of a CEO. An assistant should be put in the position where you fulfill the CEO role and not the day-to-day management of minuscule tasks. 


“Your business is your baby,” Madeleine says, so it is hard to delegate those tasks at first that you want control over, like answering client emails, but once you develop a relationship with your assistant, the delegating gets easier and you are able to let your assistant thrive. “And in return, I got my time back and I could be more strategic with what I was doing,” Madeleine recalls. 


This letting go of daily tasks can ultimately make you grow into the CEO you have always wanted to be; “You [Madison] were one of the very first people that taught me that like that is a possibility that I could actually be this more of this CEO strategy driver, visionary person versus being in the weeds all of the time.”


Having an assistant can also make you realize how you work well with others, which will benefit your company in the long run; “I realized like, and again, that was just something like I learned working with you that you like to have something to work with and you like a starting point as far as like you will go in and make your changes and, you know, tweak things here and there to fit your liking,” Madison explains learning Madeleine’s work style.

communication is key

Madeleine talks about how important communication is in this professional relationship, “I think communication is one of the biggest pieces in working successfully with an assistant. It’s also the hardest to learn because it’s not, it’s not natural. And when you, as a CEO have been in your business so long, you know exactly how things are done, you know, the way you like it’s so in your brain and trying to translate that to somebody else is a challenge and it takes a, a lot of learning to be able to do that effectively.”


So how can you communicate better with your assistant? The answer is opening up a line of communication from the start. Madison recommends having a meeting once a week with your assistant, if not daily, to go over the tasks and how you want to streamline them for the week ahead. “Even do like 8:00 AM every morning we touch base for 20 minutes and I, you know, as the CEO give, them the three things that I’m doing today that are my top priority.”


However, a good assistant also communicates as well; “A good assistant is typically able to say, ‘oh, hey what appointments do you have coming down the line?’ Or ‘do we have any major bills that need to get that you need help with’ or, you know, ‘let me see your to-do list. And let me pick out the things that I think I could help you with.’”

Madison's Advice for ceo's considering hiring an assistant

“I would go and make a master to-do list of everything that needs to get done, even the really small items. If you had basically an uninterrupted month where money was not an object, and you could just basically dive through your huge list of, to-dos and do all the things that are going to move the needle in your business, or even just the things that have to be done in your business, that makes a huge list of everything. And from there, I would really kind of look through and figure out things that you really are dreading doing and kind of figuring out what things you don’t like to do. I know that sounds weird to pick all the things you don’t enjoy doing and like putting it on a list of things to give to somebody else, but really delegating of like, these things are important,” Madison explains the first steps in hiring an assistant and delegating work to them. 


Mainly, Madison says, you want someone who is organized, has a good personality, is a go-getter, and connects with you on a professional and personal level. She says to interview candidates carefully and strategically. Hiring an assistant is the first step to finding a work-life balance and growing into the more hands-off CEO that you have always wanted to be. 


So when asking the question, ‘Should I hire an assistant?’ you first have to ask yourself what you are looking for in an assistant, and then begin to think of things to delegate them before beginning the interview process. When it comes down to it, you should get an assistant if you are struggling to find balance in your personal and professional life.

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