How to Hire and Work with an Assistant for Your Business

As your business expands, the list of things you either don’t want to do or can’t do grows with it. Whether you’re a solopreneur or you work with a full team, there will always be things you should hand over to someone else.

Outsourcing should excite you. It should be a positive experience for both you and your new hire. But it’s not always like that. In fact, more often than not, business owners who lack the proper preparation or perspective find themselves stuck in the sticky situation of parting ways with the people they bring onto their team. And each time that this happens, it feels like the right person for the job or role just doesn’t exist. 

Have you ever experienced this? Out of my 120+ clients, most of them come to me with a bold fear of hiring. 

And I get it. 

Being jaded too many times can feel exhausting. Endless, even. But what if the blame wasn’t all on the people you’ve hired? I’ve found business owners are generally pretty good at knowing they need to delegate, but many struggle with the how and what of delegating. With some coaching, my clients are often able to get past some barriers that they didn’t even know existed. The common denominator with all your past hires is often you as the business owner. So let’s give you some tools to be the best manager you can be AND how to find the right hire(s) for the tasks you need help with. 

In today’s post, I want to dive deeper into the specific things you can do as a business owner to cultivate a thriving relationship with your hire(s).  We’ll talk more about all of the following:

  • What Tasks Do You Need Help With?
  • What Skills & Qualities You Need Most?
  • Organize Your Workflows and Processes
  • Create a Job Description and Application
  • Establish Boundaries and Expectations
  • Use a Project Management Tool
  • Set-up a Healthy On-Going Foundation

What tasks do you need help with?

Anytime you outsource you need to know the state and needs of your business. Knowing exactly what you need and what you don’t can actually help you narrow in on the right person - the one that actually has the skill sets you need. It can be a cost saving thing in the long run.

You may hire someone for a one-time project or for a regular role within your team. Business owners should always be aware of their bottom line. Arming yourself with this information allows you to weed out people who don’t match your role’s standards and skip over anyone who only adds to your hiring fears or frustrations.

In the long run, taking the time to define the role, the responsibilities, and the remuneration helps you sharpen your focus so you’re able to find the right person for the job. Most of the time, I have clients come to me and say, “I need an assistant”, but they have no idea what to have them do. So my first step with them is to syphon the specific pain points or struggles they are having so we can get a better understanding of what an assistant might actually be doing to support them. Before you can even start the hiring process, it is crucial that these details be laid out. Otherwise, you may hire someone and realize they cannot do the things you need them to do. 

Here are your action steps to help you figure all this out: 

  • Figure out what you want (or need) to outsource. You can do this by keeping a log of everything you do in your business. Then split that into two parts: things only you can do and things that can be delegated. Pssst… experts say most of what you do CAN be delegated.
  • Prepare yourself to give up some control over the things or areas you want to outsource. It won’t be done perfectly.  In fact, the 70% rule will serve you well. Plainly put, if you can hire someone to do a job 70% as well as you, then it’s 100% worth it. 
  • Set-up a budget, an ideal/maximum hourly rate, or a pay range you can accommodate. An easy way to determine this is to start with what you can give up monthly for this hire. Then work backwards. Here it is broken down:
    • $500 per month = your budget 
    • $25 per hour = assistant cost (this will vary largely based on your location, skills needed, and more)
    • That leaves you with 20 hours per month or 5 hours per week that you can pay an assistant. Hurray!
  • Look at how YOU operate your business (and figure out what works and what doesn’t). Knowing this will help you know what skills you need in your new hire.

What Skills & Qualities You Need Most?

Here’s where a lot of people get messed up. Too often, business owners want to hire a Virtual Assistant that can do EVERYTHING. It’s just not realistic. What they don’t realize is that these tasks often require a different hire. 

I can’t tell you how often I’ve worked with clients who have told me none of their past assistants worked out. When I start diving deeper into their needs and how they operate, it is crystal clear why the right person was never found…. It’s because that ONE role is actually FIVE roles!

Here are the most common things my clients want help with and the different people needed for each task: 

  • Build a website = Web Developer or Designer
  • Create a social media strategy & manage socials = Social Media Manager or Strategist
  • Develop beautiful graphics = Graphic Designer
  • Write SEO rich blog posts = Ghost Writer or Copy Writer
  • Run Facebook, Instagram, or Google Ads = Digital Marketer
  • Organize all the admin parts of the business = Virtual Assistant

Yes, it is certainly possible to find someone with overlapping skills (like a VA who can also create beautiful graphics), but generally, you will absolutely set yourself up for failure if you expect one person to wear all of the hats. So you need to identify what skill sets are the most important to you before hiring. Keep in mind that each role will have varying levels of compensation. A VA for example will often be less than a Digital Marketer.

You may also want to consider: 

  • Can this hire live internationally? Generally, the answer is yes unless you need help with phone calls or shipping. 
  • What level of English do they need to have? 
  • What time zones would make it difficult to work together? 
  • What kind of personality do you work best with? 
  • What tools/programs do you need help with? If you have any specialized tools that cater to your niche or industry, you’ll want to make sure you find someone who is, at minimum, capable of learning them.

Once you have these things narrowed down, now you know specifically who you are looking for and you can better explain the job tasks. 

Organize Your Workflows and Processes

I often tell people, “You don’t need to clean the house before the housekeeper comes.” Similarly, you don’t need to have your business completely organized before hiring. This might even be why you are hiring to begin with - you want someone to help you organize it all. 

However, the more organized and clear you can get beforehand, the smoother the transition will be. At the very least, have the immediate tasks and projects laid out so your hire(s) can support you faster.

Every business has their own unique way of operating. So, it’s important to document your signature processes and workflows in the form of standard operating procedures (SOPs). Again, you may not have ALL of these ready right away. Start with the core things. 

SOPs are great for not only keeping your business consistent, but they also allow you to support or enhance the way you onboard or train your employees, assistants, and contractors. Basically, think of SOPs as your training material for new hires. 

SOPs can be as simple or as detailed as you need them to be. Don’t be fooled by what anyone says. These don’t have to be pages long. It may feel like a big commitment, but if you invest the time now to record these, it will pay off over and over again. You will spend less time hand holding each new hire and can instead just hand them a series of videos or documents to review first.

A boring Word document isn’t your only option when documenting these! You can also create a video tutorial showing the process on your screen. These videos don’t need to be long. They can be just a few minutes long for each process. This is way better than an hour long tutorial. Break it up into smaller parts.

Here’s a simple format you can use for creating your SOPs:

  • Purpose (what process are you trying to document and what does it achieve in the overall business plan?)
  • Prerequisites (what do you need to know before you can begin this task?)
  • Process (what do you need to do - the exact steps - to achieve this task?)

Bonus points if you seamlessly integrate your video SOPs into a location that can be easily shared with future hires.

Here’s what you can do to prepare for this step:
  • Create a list of all of the things you want to outsource (one list per hire)
  • Write out or record a standard operating procedure for each task 
  • Upload, store, & organize your SOPs (Google Drive, Dropbox, Trello, ClickUp, etc.)
Create a Job Description and Application

Despite what you see online, your job description doesn’t have to be several thousand words long. And, no! You don’t need a 100+ question application to be able to find your perfect fit, either. In fact, too many questions will turn away potential candidates.

All you need is: 

  • a solid introduction of who you or your company is
  • an overview of the role and its responsibilities
  • a summary of your expectations for your assistant
  • and instructions on how they can apply for the role

If you’re strapped for time, you can easily find templates via a Google search to start. 

Here are a few action steps and ideas you can use to create or set-up your job description:

  • Add your questions to a Google Form
  • Design a landing page on your website and embed the Google Form there

Pro tip: one of the things I like to ask for in applications is a short 5 min video from the applicant. It helps me get to know each candidate better AND it helps me be more efficient so I don’t spend hours in interviews with people I can quickly see are not right for the role. 

Establish Boundaries and Expectations

The age of independent contractors has exploded since the start of the pandemic. A plethora of virtual assistants are ready to work with you and are easier than ever to find. But before you go and hire one, know that working with an independent virtual assistant is vastly different than working with an employee.

Here’s where setting boundaries and expectations can save a client-assistant relationship before it even begins. After working with as many clients as I have, I have an eye for knowing whether one will flourish or fail. If your expectations aren’t compatible with your assistant’s boundaries (and vice versa), things can fall apart. And fast.

Your assistant is an independent contractor which means you are not their employer. This won’t be your traditional boss/assistant dynamic. You’re partnering and working with another business owner: one whose policies or processes may vary slightly than yours. So it’s important that you set up your working relationship clearly. 

Here are a few things to discuss whenever you hire someone: 

  • Whose contract will you use? (please don’t work without one! If you don’t have one yet, I recommend this one.)
  • What’s the assistant's rate change policy (meaning if their rate changes in the future, how will that be handled)?
  • What happens when an SOP or a workflow needs to change?
  • What are both of your working hours? If messages are received after those hours, it’s important to determine what you will do. Typically, it’s understood that the message will be responded to the next business day.
  • If your hire is hourly, how will he/she track time and send invoices? 
  • Do you find it helpful to receive a weekly recap of all that’s been done, the number of hours worked, and what’s coming next? 

Be open to questioning yourself — Mistakes happen. They’re not just caused by the assistant. When any miscommunication occurs, never rule yourself out. When a member of my team falls short, my first thought is, “What could I have done to delegate this better?” 

Use a Project Management Tool

To answer my last question, “What can I do to delegate better?”. This is it! When a client or assistant tells me their relationship is struggling, my first question is always, “Are you using a project management tool consistently?” If not, then it’s the first thing we do. 

So what is a project management tool? It’s a localized place where you can delegate tasks and make your expectations crystal clear. I used to use Trello, now I use ClickUp

Whether you’re working with a full team or just one other person, this is a MUST. It’s non-negotiable in my mind. 

Too many people hire an assistant and start delegating everything via text message, Voxer, Marco Polo, or some other tool. This can cause all sorts of chaos and miscommunication. Imagine being the assistant on the other end and scrolling through endless messages on a variety of platforms to find the details for some project you delegated a week ago…. I guarantee that if you do not use something more legit to organize the things you are delegating, the client/assistant relationship will suffer. 

Trello — I have been using this for years and I love it. It’s perfect for those that are not tech savvy and just need something simple. I love that you can get away with using the free version for a very long time depending on what features you need most.

ClickUp — I recently migrated to ClickUp because I needed something more robust. I’m completely obsessed. Their free plan offers more than Trello’s free plan. Once we moved over. Our efficiency shot up exponentially. 

Basecamp — Another great alternative for small and large teams is Basecamp. The features aren’t as sophisticated as ClickUp, but could be a great option. 

Asana — Finally, Asana has a rather sleek but simple free plan. While you won’t get access to many of its more necessary features, you can get started quickly.

Since everyone works differently, you may need to play around with each option to see which one resonates best with you. The biggest thing is to just choose one. 

Set-up a Healthy Foundation

When you gather up everything I’ve mentioned in this post, you’ll begin to see the structure of your day-to-day work with your assistant. To make sure this structure remains intact, here are a few things to do when you begin working:

Legalize your business — In case you missed it, I recently went in-depth about how you can legalize your business. There’s no one-size-fits-all approach to this, so I highly recommend you catch up with that post. One of the key takeaways was to have a contract between you and your hires. Here’s the contract I use

Never just sign a contract. Read it thoroughly. Not only is it just a bad business practice, but it can also potentially harm you or your business in the future. They are so important and help protect you and your assistant for the duration of your client-assistant relationship. Ideally, a good contract will establish boundaries between you and define anything relevant to your project or scope of work.

Keep up with your SOPs — Ensure you’re using your SOPs for consistent work quality, answering questions, and updating any change in role or work expectations.

  • Update any that aren’t working anymore
  • Create new ones as your assistant’s role expands

Set-up regular meetings — Make sure you’re meeting weekly or bi-weekly (even for just 15 minutes) to keep in contact with your assistant and to keep track of any project milestones or upcoming deadlines. If your assistant is working for 5 hours or more each week, I suggest meeting for 30-60 minutes per week. 

  • Hold effective meetings (more on this below)
  • Encourage collaborative communication and constructive feedback in these meetings. 
  • Honor each other’s time and commit to these meetings. This should be the one meeting that CANNOT change on your schedule if something else pops up. Too often business owners cancel their meetings with their assistant on a regular basis and it makes it VERY hard for them to support you. 

Hold effective meetings — This is the time for you and your assistant to chat about all the project goals, milestones, and potential obstacles, you’ll need to define what an effective or productive meeting looks like.

  • See what your assistant needs from you. I guarantee there are things he/she needs from you before they can complete a project. Reserve time to discuss those things first. 
  • Create and stick to your meeting agenda. Here is an example agenda that I share with my clients. Note: you will notice it mentions my weekly assistant calls. Those are for those who are in my program so disregard that bit if it does not apply
  • Ask for your assistant’s availability for the week. I like to ask, “What is your bandwidth for more projects right now? Are you ready for more?”
  • Identify your macros: the big projects or tasks on your pipeline
  • Figure out your micros: the small tasks (or subtasks) that needs to happen in order to accomplish the big projects

When you’re first laying out your meeting structure, keep in mind that you might have multiple macro projects running at the same time. This is where project management tools like ClickUp and Trello come in handy to keep track of all of the smaller subtasks that need to happen in order to complete the overall project. I recommend not having more than 1-2 large macro projects at a time (that take a month or more to complete).

Communicate regularly — Communication is the most important piece in any relationship. Since you’ll likely hire someone working remotely, great communication only becomes that much more pivotal to your client-assistant relationship.

  • Expect that you will have miscommunication. It’s going to happen. Decide together how you will handle it WHEN that moment comes. Remember, conflict is healthy. Contention is not. 
  • Don’t “ghost” (this means ignoring) them for extended periods of time: even when life happens. If you have a medical emergency, don’t go dark for 2 weeks and make everyone wonder if you are alive. Send a quick message that you are in the hospital and won’t be available for a few days. 
  • Say thank you and be honest about your expectations. 
  • Show your appreciation by praising their work when done right or well. 
  • Stay professional: treat your assistant with respect and like a human being. This means recognizing they have a life beyond working with you. 
  • Do not delegate tasks last minute and expect your assistant to be available. Yes, ask if he/she happens to be free, but be okay with a no answer. 
  • Try to answer emails or questions within 24 hours. 
  • Do not expect your assistant to respond within an hour. They are not on call. 
  • If you expect your assistant to be available at specific times, you need to pay for that time they are sitting around on call for you even if you have not delegated anything. PS: expecting them to be available at specific times is the definition of an employee and not an independent contractor. So if you need this, you might need to buck up and hire an employee instead. 
  • Create a team “out of office” calendar to prepare for future work. 

Set and keep realistic deadlines — Deadlines are crucial. When you assign your assistant a task or job, communicate that task’s priority and clearly make them aware of the deadline. 

A task is never fully delegated if it does not have a deadline. Seriously, I cannot stress this one enough. When I don’t know how long a task will take, I ask my assistant, “What feels like a healthy deadline for this task?” Then stick that on your project management board. 

Remember, no one can read your mind. Urgent, ASAP, and right away mean nothing since everyone interprets that differently. Get very specific on when you need something done by. 

Just as you expect your assistant to meet deadlines, you should give them the same respect. If you delegate a newsletter for example, then your assistant sends you the first draft to review, you must review it in a timely manner. Do not expect him/her to make changes last minute just because it took you a week to review it. If you operate this way, you must be okay that the newsletter will go out later than you want. 

Conclusion - You Are Not Alone

If you’re reading this blog post and you feel overwhelmed, I want you to take a deep breath. The beauty about being a business owner is that, ultimately, YOU make all the decisions (which can sometimes feel like a curse more than a blessing). 

Take what resonates in this post with you and leave what doesn’t. And if you struggle with any of it, you don’t have to do any of this alone. As the Business Matchmaker, I’ve successfully matched more than 120 clients with their dream assistants.

I choose these assistants based on what I know and what I have experienced as a former assistant myself AND now as a global CEO with multiple assistants.  My support doesn’t end after I help you find someone either! I’m there to support and guide you throughout the onboarding process, setting up your project management tool, and more so you can feel confident with the whole process. 

Forget the weeds and head straight for that bed of roses. Let’s scale your business without the fear and drama with the right assistant you’ll actually enjoy working with. Get on my calendar to learn more

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