01788 521 970

Common Challenges and Solutions when working with a Virtual Assistant

by Feb 9, 2023Blog, Operational Support

Challenges and issues can arise at any time in any business, and although virtual assistants are there to lift-the-load it does not mean they’re immune to problems. Rather than being caught off-guard, learn how to resolve common challenges, and have solutions to hand, with our in-depth guide below.


Healthy communication is essential to all levels and aspects of the workplace, and communication between you and your virtual assistant is no different. Especially in the early days while they learn your preferences and pet hates. During this process, it’s important to set out a pattern of communication which can be used as a solid foundation moving forward. Areas of initial focus, to consider:

  • Your priorities: In order to provide high quality and effective support, your assistant needs to understand your focus and goals, both short-term and long-term. As part of this, we always advise that our clients and assistants hold regular review meetings.
  • Clear expectations: From the outset, make clear your requirements and any deliverables. As part of the on-boarding process, key skills and tasks need to be identified. Of course, it goes without saying that your assistant’s standard of work should always be to a high and professional standard. If they fail to deliver on this, don’t hesitate to highlight any issues as they arise.
  • Understand your virtual assistant’s requirements: Your virtual assistant is not a full-time employee and will likely be working with other clients and have personal commitments which will affect their working hours. We recommend, enquiring about their availability before any work commences. Keep this in mind, in regard to last minute requests.
  • Open communication is key: It is fundamental to your working relationship that you and your assistant raise concerns as soon as they become apparent. This will allow you to learn from mistakes and move forward confidently. Be sure to create and commit to a working environment where this is acceptable and achievable.


It is important that infrastructure is in place to support your own (and your organisation’s) requirements. Key considerations to consider:

  • Internet connection: It is fundamental that your assistant has access to a stable internet connection. As part of this, you may wish to ask for information on bandwidth availability and internet speed. You also need assurance that, should they temporarily lose connection, back-up options are available to your virtual assistant.
  • Webcam, with clear video and audio: You and your assistant must be able to clearly communicate via video meetings.
  • Familiarity with your organisation’s email and project management systems: You should enquire whether your assistant is familiar with your preferred email system, and any CRM or project management tools you might use. If they’re not; schedule some time to talk them through these systems before they start working with you.
  • Working space: Your assistant should be used to working from home, but it is important to ascertain that they have a dedicated office space. Consider whether their working environment is conducive to a high standard of professionalism.
  • Create a hybrid-ready working environment: If your assistant is to work as a part of a team, it is important they are fully integrated. To successfully achieve this, your assistant needs to feel part of your team and be able to confidently speak to other members of staff when required.

Confidentiality and privacy

Your confidentiality and privacy is absolutely crucial to your working relationship. Your assistant should be sensitive to the areas of confidentiality within your business, which they have access to. We recommend taking the following steps to ensure confidentiality is maintained at all times:

  • Non-disclosure agreement: Your assistant can provide you with a non-disclosure agreement to sign before you begin working together. Alternatively, you may wish to ask them to sign an agreement from your organisation.
  • Computer security: Your assistant’s computer must not be at risk of security breaches. As part of this, you may wish to arrange for an IT security health check with your own, or an outsourced, IT support team.
  • File-sharing systems: We recommend having a cloud-based file sharing system in place. If your assistant is to work as part of a wider team, all members should share information within this appropriately, with security-protected passwords in place if required.
  • Password sharing: You will most likely need to share passwords with your assistant. In order to protect confidentiality, we recommend using LastPass or Dashlane. These systems will allow you to manage your passwords and keep your logins secure.
  • Data protection: All Virtual Assistants should be registered with the ICO as part of GDPR requirements.

Delegating Tasks

One of the biggest barriers to working effectively with a Virtual Assistant is nervousness, or reluctance, to delegate. Below are some suggestions on how this can be overcome and how tasks can be efficiently shared:

  • Respect your time: Recognise that your time is valuable and keep in mind your ambitions and goals. Identify tasks which do not reflect your worth and seek to delegate these.
  • Build on your working relationship: Recognise that your relationship with your assistant is long-term, and that you can increase how much you delegate as you both become more familiar in working with each other.
  • Make use of project-management systems: Software such as Trello, One Note or Slack, enable you to share projects with your assistant, setting out clearly identified tasks and deadlines.
  • Hold regular calls or meetings: These enable you to share your priorities and your focus going forward. Your assistant will then be able to suggest tasks which they can undertake to support you in achieving your objectives.

The culture of your organisation

It is important to recognise and acknowledge that cultures across organisations vary, and that this can affect behaviours and preferred communication styles. We set out below considerations to bear in mind:

  • Clarity on day-to-day communication: Set out your favoured preference for daily communication from the beginning. Whether this is email, phone, WhatsApp or another communication tool, make sure these are available to your virtual assistant.
  • Style of communication with colleagues, clients, and prospects: Some organisations can be very formal, whereas others are more relaxed. Whilst your assistant should be able to identify the level of formality required, it would nonetheless be helpful to set out some guidelines, such as your preferred email protocol, or any company/ in-house guidance or rules.
  • Different time-zones: If your assistant is based overseas, you should be aware of implications on working hours and availability.
  • Cultural differences: Styles of working can vary in different countries. There is no right or wrong to this, but you should bear in mind, when working with a Virtual Assistant, that someone’s cultural background inevitably affects their approach. This approach could include their communication style and their attitude to how business is conducted.

Just as in any other aspect of life, strong working relationships really matter. By identifying and addressing challenges as they arise, you will create a safe space for honest discussion going forward.

At Executive PA Solutions, we pride ourselves in understanding our clients’ requirements and goals. If you would like to discuss with us the tasks you would like to delegate, then please get in touch. We’d be happy to discuss how we can work together .




× Start a conversation...