What are the Risks of Hiring an Assistant and How to Avoid Them?

What are the Risks of Hiring an Executive Assistant and How to Avoid Them?

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Many founders and entrepreneurs come to the same, harsh realization when they’re trying to take their companies to the next level: it’s time to stop doing everything yourself and refocus your energy. The next logical step would be to find someone who can help take care of everything that isn’t your core responsibility. Hiring executive assistants to manage your communications and calendar can have positive trickling effect on your productivity, work-life balance and effectiveness as a leader. Which ultimately impacts your company’s bottom line. But let’s be real, hiring an executive assistant comes with its share of risks and challenges.

Think about it: if the EA you hire isn’t a good match, that could disrupt your workflow and productivity instead of improving it. And what about your and your company’s reputation?

No business decision comes without risks, we all learned that the hard way at some point. What’s the first step to overcome these challenges? Knowing what the risks associated to hiring an assistant are.

Let’s walk through them.

Lack of Training

That’s probably the number one thing executives are dreading when it comes to hiring: the costs and time involved in training EA and the risk that it may eat up more time than it actually saves. Academic and formal qualifications don’t necessarily mean an Executive assistant has the hands-on skills needed to deliver premium assistant services to their executives.

If you end up spending time and money recruiting and training your EA, where’s the benefit for you? If only they could hit the ground running and already know what you need from them…

Communication Issues

What happens if you and your EA don’t understand each other? From language barrier to mismatching needs and expectations, even simple aspects can turn into a daunting back and forth on Slack between you and your EA.

Maybe you’re an async communication advocate, while your EA keeps trying to call you for quick catch-ups. Or you might like to have extensive, regular updates on ongoing and outstanding tasks, but your assistant prefers to drop you only one message a day once things are done.

Like any relationship, it takes time and effort to get used to one’s communication style and know what both of you expects from each other.

Data Security Risk

When it comes to hiring an executive assistant, data security and privacy are an important aspect you should consider. You need to fully trust someone to securely manage your personal details and correspondence.

Discretion is key! Some assistants might not have the skills and knowledge to uncover and avoid spear-phishing attacks. Or they might not have secure processes in place to store and handle sensitive information. They could fall for email attachments purporting to be relevant such as voicemail messages, invoices, documents, and payment advice.

Cultural Background Differences

Executive assistants come from all walks of life and backgrounds. This can be a great added value, but it also means that their understanding of your culture and company goals could take some time. If you hire a virtual or freelance assistant in a different country, you might not get the support you need when it comes to dealing with local bureaucracy or knowing the best restaurant in your area.

Single Point of Failure

One of the biggest risks of working with an EA, often overlooked, is becoming people-dependent. Which means, being completely reliant on one single person. What happens if your freelance virtual assistant is suddenly sick or decides to move to another role? Who takes care of your calendar and schedule while they’re on vacation or parental leave? All of a sudden, you find yourself without the help you need, and nobody to take over your to do list.

That’s a risk that we overcame at Headroom: with us, you get more than an extra pair of hands, you get a dedicated mighty EA team who knows what your workflow and needs are. They can hand tasks over to each other when your primary EA is away. So you are always covered and nothing falls through the cracks even if someone is on sick leave or vacation!

The Unknown Factor

Sometimes, it just doesn’t work, no matter how perfect the assistant was on paper. It could be the connection between the both of you, the work environment, or the EA’s inability to deliver to your company’s expectations.

How to find the right EA for you & minimize risk

We just talked about the risks and challenges that come with hiring an executive assistant. But this doesn’t mean you should not get one.

Executive Assistants can take many important tasks off your plate: they can manage your complex inbox and agenda, book private and business travels and follow meetings on your behalf. Beyond that, an assistant should be able to think along with your about how you can achieve goals and unlock possibilities. At Headroom, for example, all executive assistants are trained to be proactive, strategic partners to the members they assist.

In addition, an EA can also support you on a personal level. They can take care of personal tasks and workload so everything will be balanced and streamlined. This way you will have more time for new business ideas, family and social activities and a better work-life balance.

Let’s see the steps you should follow to hire the perfect executive assistant for you.

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Write down your expectations and what you need your EA to do for you

To hire an EA with your interests in mind, tie your search to a goal. Know your expectations and the kind of bond you want to create with the assistant, as well as the type of tasks you would need them to perform.

Use an EA Service or vetting agency

Hiring a vetting agency or EA service ensures the EAs have a minimum level of training and consistent quality of service, in contrast with hiring a freelance assistant. That reduces the time wastage and costs of training the EA after hiring them.

Decide on the Communication tools

Choose the communication tools you’ll use and ensure your EA is knowledgeable and comfortable using them. Negotiating your expectations and needs is crucial to transparent communication and proper flow of information. Decide on whether you want 24/7 coverage or office hours, async communication, and how often you should check in with each other.

At Headroom, we have weekly check-ins between EAs and executives; we use Slack for every other matter and integrate seamlessly into your tool stack – be it Gmail, Outlook or Notion.

Decide the information you want to share with your EA

You probably don’t want to give out every executive detail of your business. We recommend that you create a personal inbox and only give your EA access to your business inbox. Get your EA to sign an NDA and ensure they stick to it.

When you need to share sensitive data like ID number or bank details, use a digital wallet and encrypted password manager like 1Password or Keeper. That’s precisely what we at Headroom use to guarantee the safety of customer data when our EAs are booking tickets, holidays, and appointments for our executive clients.

Decide if you need someone local to your area

Is cultural affinity and language fluency important for you? Do you need someone with in-depth knowledge of local bureaucracy and regulations? Then you should look for EA services that offer assistants local to your area.

If you’re working with a virtual assistant from another country, it’s always worth checking in with them to avoid any ambiguity or possible misunderstanding. As in any other partnership, the key is to talk to your EA and build a healthy and transparent relationship with them.

Be present and Anticipate

Don’t completely withdraw from what’s happening with your schedule. Ensure you have a regular overview of outstanding tasks and meetings coming up. Ask your EA to notify any PTO at least 2 weeks in advance. It’s also good practice to prepare a plan with them to stay on top of things while they are away.

Or you can also consider using an assistant service like Headroom.

To overcome the EA single point of failure, we offer an entire EA team dedicated to crushing your to do list. This means continuous support: even if your primary EA is off, another colleague will take over your tasks and you won’t even notice, we promise. How can we do that so efficiently? We use our task management platform to seamlessly hand over tasks to each other and make sure our members get ongoing support, with the same quality standard.

Ask for recommendations

Some things simply cant be predicted, especially when it comes to people and human relations. What we can say is, don’t let one bad experience stir you away from getting the support you and your company need! To reduce the risk, why not asking advice from your entrepreneur community? At Headroom, we see many of our members coming from referral and word of mouth. After all, people trust people. Especially when it comes to a high involvement decision like hiring an executive assistant.

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Entrepreneurs can ask for recommendations in Slack groups

Determine the Tech-savviness of the EA

It’s 2022, is there still someone out there using Word and pdfs share documents?

Whatever your favorite productivity and communication tool is, make sure your executive assistant is comfortable using it. You can rely on your EA to recommend the latest collaboration software and apps to track performance, collaborate and manage tasks.

One thing that sets Headroom remote EAs apart is their tech-savviness. Our expert assistants have an in-depth understanding of administrative and productivity tools such as Google Slides, QuickBooks, and Excel.

Know if they reflect Your Executive Values

Ultimately, EAs are the right hand to executives and they should also represent them. Therefore, look for an EA with solid attention to detail and incredible verbal and written communication skills. Someone who will be able to deal with things on your behalf in a professional manner.

Headroom is a premium Executive Assistance company with over 10 years of experience supporting executives in the US and Netherlands. We are a top-rated service with a solid track record providing c-suites, tech founders, and CEOs with the help (and time) they need to unlock growth and possibilities.

What we bring to the table is not just additional hands to assist with administrative tasks. But committed and tech-powered specialists to enable you to handle any task and unlock your own potential. We hire, manage and train our own EAs, so you can simply subscribe to one of our flexible memberships and start getting your time back, one task at a time!

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