Cultivating a fruitful collaboration with your freelance executive assistant

In Search of Professional Harmony: A Guide to Establishing a Flourishing Relationship with Your Independent Executive Assistant

When it comes to recruiting a freelance executive assistant, the key to success lies in creating a harmonious collaboration. It’s easy to imagine that you’d like the relationship and collaboration with your freelance assistant to be a long-term one. You’d also like to have confidence in your executive assistant. Like any manager, you need cohesion, so that your assistant understands you easily, can anticipate your needs and, above all, doesn’t have to train several freelancers one after the other.

Your assistants can do much more than carry out administrative or repetitive tasks; they can become real pillars of your organization. That’s why building a healthy relationship with your assistants will contribute to your company’s efficiency and productivity. Here are a few tips to help you cultivate a fruitful collaboration with your freelance executive assistant and turn your partnership into a success story.

1. Authentic Communication for Healthy Collaboration with your Freelance Executive Assistant

Transparent and constant communication for a sain collaboration

Transparent communication is the cornerstone of any successful collaboration, but even more so with your freelance executive assistant.Establish the basis of your communication with him/her right from the start. Create open communication channels from the outset, encouraging frank exchange. Clarity about mutual expectations and deadlines prevents confusion later on.

First of all, remember to make time in your week for your assistant. Set aside time for discussion, so that he can understand your requests and express his questions, report back to you on the information he has obtained, and so on.

Many companies choose to work with remote freelance executive assistants. This could very well be the case for you. You’ll need to establish the means of communication from the outset: telephone, e-mail, LR mail (you never know!)? I think it’s wise not to choose to multiply the channels. If you send a text message, followed by an email reply, crossed with a WhatsApp message, the information is likely to be lost. Your assistant could quickly become overwhelmed by the means of communication rather than the tasks at hand.

When it comes to working on site, you might think that communication is easier and more natural. This may be the case if your working environment is conducive to communication, but it’s not always that simple. When the new employee arrives, you can explain how you work: are you a fan of the open-door office? Or, on the contrary, do you prefer to set aside time for specific exchanges?

Your assistant needs to understand your communication needs. He or she should also be able to tell you what expectations he or she has, so that your collaboration with your freelance runs as smoothly as possible.

2. Define the Responsibilities and Objectives of your Independent Assistant

To cultivate a fruitful collaboration with your freelance assistant, one crucial point: make sure your independent executive assistant has a clear vision of his or her responsibilities and of your company’s objectives.

During the training phase, be sure to explain to him or her what is at stake for you and your company. For example: you want to sell your company within the next 3 years. So you need to start handing over the reins in the next few months. By knowing your objectives, he’ll be able to adapt his work. He’ll understand his position within this objective and won’t be at a loss when discussing the subject.

Define the missions

It’s not always easy to define the tasks your freelance assistant will have to carry out on a daily basis. You may not know exactly how to describe all the tasks, or it may seem obvious to you. All managers are different, and what you expect of your assistant may be laterally opposed to what is expected of him or her on another contract. I think there are two ways of approaching the problem of assignments:

  1. List everything she can do (or have your current assistant do it);
  2. Offer her a simple explanation of your daily routine. She can also follow your work over several days so that she can establish which assignments are relevant to your daily routine.

The list of tasks defined for an administrative assistant or secretary is often incomplete, unless you have very specific needs. For example, you might only want to ask them to create quotations. However, drawing up an exhaustive list from the outset will help you avoid disappointment in the event of an urgent need. What’s more, a detailed list will help prevent disputes, a reality that is sometimes unavoidable in this field. Above all, it will help to establish a relationship of trust that is indispensable in this collaboration.

Next week, I’ll be offering you an article on how to write an engagement letter to create a fruitful collaboration with your freelance executive assistant.

3. Collaborate successfully: Respect reasonable deadlines

I believe that one of the keys to a healthy collaboration with your freelance assistant is undoubtedly the definition of urgencies. Avoid pitfalls by setting realistic deadlines. Transparency about priorities makes it easier to organize work and prevents unnecessary stress.

Of course, your assistant must be able to understand whether the e-mail he or she has just received deserves to go on the top-list, or whether it can wait a few minutes before being processed. However, it can be very easy to interrupt him frequently with new requests. To ask him to send messages later in the day, but before 6 p.m. the next day… When, according to your definition of his working time, he’s not working for you the next day and he’s got 10 minutes left before his day ends. I hope you read that last sentence without catching your breath.

At the start of your collaboration, it’s important to let him know what’s important to you. How to handle them, and which tasks can be done at his discretion. He also needs to rely on transparent communication to tell you when he’s facing too many emergencies. At this point, you should be able to discuss how to handle things: can he delegate, do you decide to put certain files on the back burner?

4. A Positive Work Environment to encourage collaboration with your freelance executive assistant

Cultivating a beneficial working relationship with a freelance executive assistant also means cultivating a positive and motivating work environment. Recognizing your administrative assistant’s achievements. Providing constructive feedback and encouraging professional development are crucial to strengthening the relationship.

Acknowledging successes, whether big or small, creates a sense of accomplishment and boosts your employee’s motivation. Constructive feedback is also essential. Instead of simply pointing out mistakes, focus on opportunities for improvement. Adopt a constructive approach that encourages learning and growth. This type of communication fosters an environment where challenges are seen as opportunities to evolve rather than failures.

Encouraging your freelance administrative assistant’s professional development demonstrates an investment in his or her career. Identify areas where he could improve or acquire new skills, and support his access to relevant training. This shows that you value his professional growth and are willing to invest in his long-term success.

And don’t forget to integrate them into your company: although they may be independent, they are very much part of the life of your business. By facilitating professional relations between them and your teams, you’ll encourage their work and facilitate the exchanges they need to support you and develop their skills alongside you.

By encouraging these practices, you help create a positive, dynamic working relationship. It reinforces your administrative assistant’s loyalty and commitment. It also creates an environment conducive to profitable collaboration and the achievement of common goals.

Cultivating a positive collaboration with your freelance

5. Collaborative tools for maximum productivity

A constant theme in modern-day business, there are dozens of tools available to help you with your day-to-day tasks. These tools can facilitate the work and collaboration with your freelance assistant, but also that of your team in general.

It’s quite possible that you may feel disconnected from these solutions, but don’t panic. I believe that any good assistant knows a lot of tools and will be able to advise you or explain to you what he or she needs to function in the best possible way. Talk to him, explain what you like, what you don’t like. He’ll be able to put in place solutions that suit your environment.

In the event that you’re an afficionado of the latest tools, think about providing your assistant with training in your tools so that he or she can easily get to grips with these technologies.

I should do an article on the software I’m loving at the moment (yes, it’s changing), but I’d like to mention a few that are helping or have helped me:

  • Trello: a tool for organizing yourself according to the SCRUM method. These are post-it notes that you move around to track the progress of your project. Trello can be used solo or collaboratively;
  • Notion: a kind of large briefcase that lets you add and organize all kinds of documents, surveys, images, etc.
  • TogglTrack: a small application that tracks time spent on tasks or projects;
  • Microsoft To-Do: to create to-do lists, manage deadlines and rehearsals [and avoid filling your calendar with all kinds of reminders];
  • Slack: a collaborative communication platform. It lets you exchange messages, images, documents and more.

6. Respect for privacy and working hours

Respectinf delays and working hour to collaborate with a freelance assistant

Recognizing and respecting professional and personal boundaries is essential. Someone once said to me: “Okay, you’re there for your company from 7.30am to 9pm, […] so when the day comes and there’s a real emergency situation that needs your full attention… how will you make the decision?”. Whether manager or assistant, our jobs are not sprints but marathons. By giving your assistant the opportunity to rest, disconnect and be free, you’ll be able to benefit from his or her renewed energy every day.

To build a fruitful collaboration with your freelance executive assistant, remember to define working hours from the outset. This won’t prevent flexibility, but it will ease the pressure on a day-to-day basis. You’ll also know when to count on him.

Here’s a useful tip: check your contract (engagement letter, general terms and conditions of service, etc.) to find out the freelancer’s rates. It’s possible that you’ll be required to work longer hours and that you’ll have to pay a higher fee.

7. Regular Feedback: A Key to Success

To build a successful collaboration with your freelance assistant, follow-up is just as important as communication and planning. Consider scheduling regular meetings to discuss progress, challenges and opportunities for improvement. Just as you would with your employees during their annual appraisal, for example.

Although a freelance assistant may be interpreted as outside the company, he or she is something between employee and supplier. You don’t have the same contract with him as with an employee, but his contract is not simply that of a distributor. He will have access to a great deal of information, and will become a pillar of your daily work. It’s vital to be able to discuss both his work and your future objectives.

Open up the discussion with regular updates, either every 6 months or every month, depending on your needs. You’ll probably need to do this more regularly if your executive assistant is working remotely. This would also be a good opportunity for an on-site review. Think of it as a free, open and trusting discussion to bring your relationship up to date.

Conclusion to cultivating a fruitful collaboration with your freelance executive assistant

Establishing a healthy relationship with your freelance administrative assistant takes time, understanding and mutual respect. The key to this relationship is undoubtedly communication. Before, during and after. As with any relationship… By investing in these fundamentals, you create a solid foundation for a fruitful collaboration, beneficial to both your company and your valued freelancer.

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