When deciding to entrusting an assistant with your companies, it’s not always simple. Maybe, you had your assistant close to you for the last ten years, or you’re deciding now that it could be a great investment for your day-to-day needs. Whether you’re a busy entrepreneur, a growing business, or an individual in need of specialized support, hiring an independent assistant can be a game-changer. However, making the right choice requires careful consideration and a thorough vetting process. Before entrusting a mission to the right Independent assistant, it’s essential to ask the crucial questions to ensure a successful and long-term partnership.
In this article, I will explore key questions that you can or should investigate before deciding to entrust your next independent assistant with your company and personal matters.
Experience
and Expertise
This section is about understanding whether your candidates can adapt to your needs. Do they have the right training and have they faced the same requirements in other experiences? It may seem a bit standard. In fact the way you ask the questions can reveal important information about candidates and their ability to adapt.
Simple questions to the right independent assistant first
You can start with simple, open-ended questions that your next independent assistant should have worked on. A good example is What is your experience as an assistant over the last (5) years?
This question will highlight the most important experiences of the freelance assistant. Find out which experiences are important to them. Also, check whether they adapt their answer to the information you have given them. You can also ask: How long have you been working as an assistant and then as a self-employed assistant?
Although it’s not always important to have an assistant with 10 years’ experience, it can help you to understand their level of independence.
Don’t forget that hiring a freelancer can be the same as hiring an employee. Even if their situation in the company is not administratively the same, they will have an impact on the day-to-day work and environment of your company. It’s good to ask questions about the soft skills and hard skills they can offer. I would not recommend immediately asking “what are your strengths and weaknesses“. Indeed, they have worked on that and it will not be really constructive. Instead, you can try questions that focus on specific topics, such as How would you organize and follow up meetings?
You can also send your candidates a test or ask them about a case study. How did you deal with this particular situation in this experience? Can you tell about an experience where the deadline was very short and complex to meet and you managed it? Can you give an example of a situation where you took the initiative to address a problem?
It’s important to identify the soft and hard skills that the candidate mentions or demonstrates.
Training is a matter to discuss
There’s one question I like to understand more about a candidate. I think that executive assistants or administrative assistants need to train regularly. That’s why I recommend asking: Are you currently training in a particular field or subject?
This is not a question about past or other experiences. It is a question that helps you to understand whether the assistant will improve and continue to develop their skills
Availability and Workload
When hiring freelancers, you need to be aware that they will rarely be fully dedicated to you and your business. More often than not, you will hire them for a specific purpose. For example: replacing a missing assistant, or for a few hours a week, which you can tailor to your needs.
The questions in this area are quite simple, they are technical. I always avoid direct questions in this area. For example, I would recommend asking “How much free time do you have in your schedule each week?” instead of “Can you give us 10 hours of your week?”
The first question will help you understand if the time offered by the candidate can meet your needs.
As mentioned before, it is quite certain that the right independent assistant will not only work for you. You can then ask What is your daily routine? How much time do you already have with other clients? How will you deal with my requests if you are dealing with another client at the same time?
If you are used to working nights or weekends, or if you travel a lot, make sure the candidate is able to cope with these demands.
Questions about understanding
of Mission Objectives by the right Independent Assistant
You now know a bit more about the candidate, but before you go any further, I’d advise you to find out if the candidate can relate to the jobs you’re asking them to do. Either you contacted them with a list of tasks, or they contacted you in response to an offer where you explained the tasks, but generally the freelancer already knows a bit about the tasks he/she will have to take on. For me, given that they already know some information, I’d recommend asking questions like Can you articulate your understanding of the objectives and goals of the assignment?
Or Can you name a client and context for whom you’ve done the same assignment before?
Of course, if the candidate is unaware of the assignments they are being considered for at this point, it is time to make the list and see if they can identify themselves on it. Ensuring that the assistant fully understands the objectives of the assignment is fundamental to success.
Tools
and Technology
Working with an independent assistant doesn’t mean you have to adapt to the tools they use. In contrast to the first questions, which I advised you not to ask directly to the independent assistant, talk clearly about the software and tools you use. Before interviewing the candidate, review all the important information about the tools, hardware and software. Will they need to install any software on their computer? Do you expect them to have the necessary licenses? Will you provide a computer or telephone?
You can then decide what questions to ask. Are you familiar with this tool, this software? How do you deal with adapting to new tools? Have you worked with this type of tool before? Can you name a tool you have used for accounting?
Remember to ask about your candidate’s workspace if they will be working remotely: Do you have everything you need to work comfortably and efficiently at home? Do you use fiber optics or other technology to access the internet?
Communication
and Reporting
This part is a bit different, you can decide that as a client you don’t really need to ask, just tell the freelancer what you are looking for. Let’s say that asking these questions to the independent assistant will make it easier for you to understand their character and way of working, essure that you find the right independent assistant. It will be harder to make a mistake when hiring the freelancer.
To understand how candidates works in terms of communication and reporting, you can start by asking them What is your preferred way of communicating?
If they tell you that they prefer email when you only like phone calls, it can be difficult to act in a long-term relationship. In the same area, you can ask the candidate: How often do you usually provide updates on the assignment?
A really important issue is the candidate’s ability to hear feedback in order to adapt to your needs. A good question to ask might be: What was the last feedback a client gave you? You could also ask: What was the last criticism someone gave you? What did you do about it?
A willingness to learn and grow is a sign of a proactive and dedicated freelancer.
References, Testimonials and Network
A freelance assistant has to go through a number of experiences before he or she becomes a freelancer. Even if they are starting their solo adventure today. As their future client, you need to know as much as possible about their past experiences. At this point, they have told you about their experiences, but feedback from previous employers or clients can be useful, depending on the tasks you are willing to entrust to the freelancer.
There are two solutions, either you can do your own research, if the candidate has been practicing for a few times, there is a chance that they may have recommendations from their previous clients on platforms such as LesBonsFreelances or Malt. The second solution is to ask to call former clients or employers yourself to ask your questions: Can you provide references from former clients or employers?
Working with the right independent assistant means that you will need support, advice and a lot of initiative from them, and this means that you may need services other than the ones they provide in the first place. One day you might need a lawyer to help you with a case, another day you might need recommendations for a special place to hold your events. Knowing that the freelancer you choose has an important or specific network can be a great opportunity. You could simply ask directly, What network do you rely on?
Or more specifically, If I were to ask you for an accountant to do my bookkeeping, do you have anyone you could recommend?
Confidentiality and Security
Confidentiality is a big issue when working with a freelance assistant: they may be working from home, even on their own equipment. You may wonder what they will do with your data and information, and what risks you’re taking. As the right independent assistants, they should be used to working with a number of clients and their confidential data. You can then ask them How do you ensure the confidentiality and security of sensitive information?
Or How do you store/secure your clients’ sensitive information?
Another interesting topic would be to ask your assistant: Are you going to entrust other people with my or my company’s data?
It can sometimes be useful to discuss issues with others to speed up the process or to find the right way to do something, but confidentiality should be discussed first.
Don’t forget that you can sign a non-disclosure agreement with your candidate, even before the interview, if necessary. Remember that confidentiality is not an option for your company, your next assistant will have to apply the same level of confidentiality that you ask of your employees.
The way people work has changed. Freelancers can work on-site or off-site, and this last option can mean a lot. An interesting question might be: Where do you work when you work for your clients?
It is more and more common to work in a coworking space or in cafes, for example. Does your assistant do this? Is it okay for you? Also, if you work in public places, you should ask these questions to your next independent assistant: Do you use a privacy screen? Do you only work on documents or do you make phone calls and video calls in public places?
Contracts, rates
and Payment Terms
Last but not least, you need to know how the contract between your company and your next assistant will work.
The Mission Letter : questions to ask to the right independent assistant
First of all, I think it is very important to define the tasks precisely and to ask your assistant to write a mission letter. This type of contract lists all the tasks he/she will carry out for you during your collaboration. It will also set out the terms of the contract, such as rates and payment terms, conditions for fulfilling or terminating the contract, duration, etc.
Speak about the rates and needs
To write this letter, you need to discuss a number of elements. Questions need to be asked to find the right independent assistant: What is your hourly, daily or project-based rate? Are there any additional costs or expenses I should be aware of? For example, if you come on-site, Are the on-site costs already included in the hourly or daily rate?
Speaking of payments, talk about payment terms, it won’t be the same for a project-based assignment as for a recurring contract. When should we pay you? What are your payment terms?
Remember also to ask if the candidate is self-employed – not subject to VAT – or invoicing through a company – subject to VAT, this could make a big difference to you: Are you subject to VAT?
It is also important to discuss equipment and software: Do you have this specific software or equipment? Will you purchase it? Do you need us to supply it? In most cases, independent assistants will have their own equipment (computer, telephone), as well as the basic software licences (Office). However, if you work with specific devices or software, it may be important to provide them with the tools needed.
In France, as a freelancer, you can’t work with just one client as this could mean a hidden employment contract. Please check that your candidate is working or will be working with other clients throughout the year. Do you have current contracts or ongoing discussions with other potential clients?
Conclusion : hiring the right independent assistant
Hiring the right independent assistant is not as different as you might think from hiring an employee for your business. Choosing the right independent assistant is a critical decision that can significantly impact the success of your mission. Most of the time, you will be expecting this assistant to fit into your organization quickly. You will expect him/her to work autonomously and to make strong proposals. By taking the time to ask these questions, you can gain a full understanding of the assistant’s skills, work ethic, and compatibility with your organization. Taking the time to thoroughly vet potential candidates will ensure a more fruitful and harmonious working relationship. Imaging setting the stage for successful mission outcomes right away!
Need help preparing your next freelance assistant recruitment? Download our dossier to make it easier.
File to prepare interviews
Send download link to:
