How to Hire a Personal Assistant for Your Startup

how to hire a personal assistant for your startup

Ask anybody who’s ever started a business – running a growing startup requires a substantial commitment of time, energy, and money. As your business grows, you’ll inevitably become overwhelmed with all of the work needed to keep it going. You’ll try to start prioritizing your tasks, but, unfortunately, it’s easy to makes mistakes – giving more complex and urgent tasks precedence over the more mundane.

This sounds smart, but it’s a trap. Ignoring mundane, but essential, responsibilities can get you into a lot of trouble, as small things like forgetting to make your quarter tax payments, replying to emails and remembering to follow up with suppliers are every bit as important as pitching an angel investor or releasing a prototype of an upcoming product.

However, while these simpler tasks are extremely important, you don’t want to let them eat away at the limited time you have available to grow your business. In this case, the solution may be hiring a personal assistant to handle your administrative tasks for you.

Do You Need a Personal Assistant?

Personal assistants can be an asset to any growing business, but it can be difficult to tell when it’s time to pull the trigger and bring one on board. If you’re like most startups, you’re probably strapped for cash – meaning that you can’t afford to waste money creating a position that you don’t need right away.

If you aren’t sure whether or not you’re ready to take this step, ask yourself if any of the following sound familiar?

  • You feel exhausted at the end of the day.
  • You’re starting to question whether running a startup is worth all of the energy you need to allocate to it.
  • You find that you never have enough time to get everything done.
  • Your relationships with your spouse, children or friends are starting to suffer.
  • You’ve decided to slow the growth of your business to keep yourself from being overwhelmed.
  • Your partners or other employees are complaining that you keep trying to push mundane work on them, making it difficult for them to complete their more important responsibilities.

It’s also a good idea to score the activities you spend most of your time on according to the Eisenhower Box. Popularized by the 34th President of the United States, the box is composed of four quadrants designated as “Urgent” or “Not Urgent” and “Important” or “Not Important.”

  1. Urgent and Important (Quadrant #1) tasks include those that you must handle today and that you need to tackle yourself. Identify these tasks and handle them immediately.
  2. Important, but Not Urgent (Quadrant #2) tasks involve things that are important for your business, but that you can schedule yourself to handle later, such as developing your content marketing strategy or evaluating your business insurance.
  3. Urgent, but Not Important (Quadrant #3) tasks are those that need to be done, but that can be handled by somebody else (like, say, your new assistant…). Possible tasks in this quadrant may include booking travel plans or managing your social profiles.
  4. Not Urgent and Not Important (Quadrant #4) tasks shouldn’t be on your radar at all. Be ruthless about cutting them when you find them to make more time for tasks in Quadrant #1 and Quadrant #2.

If any of these factors or descriptions hit home with you, you’ll probably benefit from hiring a personal assistant. And assuming you can free up even a few hundred dollars a month, the following process will help you find, hire and train the worker that’ll make a big difference in your personal and professional lives.

How to Hire the Right Personal Assistant for Your Business

Your new personal assistant can either make your life much easier or create a ton of huge (and possibly expensive) headaches down the road. As pointed out in my “Hiring Secrets from Top CEOs” report, the average ROI of hiring the wrong candidate for a job is -298%. The repercussions of choosing the wrong person to be your personal assistant can be just as devastating, so make sure to do your due diligence during the hiring process.

Ultimately, it all boils down to finding a candidate that’s responsible, hardworking and dependable. Here are some tips to guide you through the process:

Set the Qualifications and Salary Before Posting the Position

Let me start this section with an illustration showing why it’s important to think through what your assistant will do for you before you post your position, rather than after…

You decide that you need a personal assistant, so you post a general ad to a site like Guru or Elance. Because these sites have thousands of people who identify themselves as such, you receive hundreds of different applications for your assistant position. You pick the one with the highest ratings and hire them.

The problems begin right away. You hadn’t really thought about it before, but it’d be really helpful if your assistant could take over your Facebook and Twitter posting. The problem? The candidate you hired has never done this type of work before. Now, you’re faced with a difficult decision. Do you spend time teaching your assistant how to do social media marketing, or do you go back to the drawing board and start the hiring process all over again with a clearer job description?

I think you’ll agree, it’s best to decide what tasks your assistant will need to be responsible for and what compensation will be appropriate before you even think about posting the position. The following sample responsibilities should get your creative juices flowing:

  • Taking calls from customers, vendors and other stakeholders
  • Filing W-2s, taxes and other legal forms
  • Managing the company’s social media profiles
  • Scheduling meetings
  • Organizing travel accommodations

If you need your assistant to be responsible for more complex job responsibilities, then you’ll need to be prepared to pay more. Startups on a tight budget may need to hire a less experienced assistant, but even a recent college graduate can significantly reduce your workload without requiring a hefty starting salary.

Consider All Possible Channels for Finding Candidates

Your first instinct is probably to look for candidates through sites like Indeed.com or Monster.com. But remember that four out of five jobs are never posted online, so there’s no reason to limiting yourself to candidates on these sites. While it’s still a good idea to post job opportunities online, you should consider other venues available to you. There are a number of other options to consider.

For example, you can start by speaking with the alumni office at your alma mater. Their representatives will be happy to refer recent graduates to you that may be looking for an entry-level career opportunity.

You should also always be on the lookout for potential candidates whenever you go out. Roberta Chinsky Matuson, founder, and principal of Human Resource Solutions, told Inc. that you may find the perfect candidate while out shopping, which is why it’s so important to keep your eyes peeled.
“If you’re a smart CEO, you are constantly on the look out for people who impress you. If you’re at the pharmacy and someone treats you with dignity and respect, ask them to stay in touch in case you have an opportunity,” she said. “Let’s face it, they’re pretty rare.”
Your existing employees or contractors are also another place to turn to for recommendations. They may know talented people that are interested in the position.

You may need to consider a number of different options before you can find the right candidate. Try to cast as large of a net as possible, as you never know where or when you’ll first encounter your new personal assistant.

Invest the Time Needed to Choose a Great Candidate

If you use all of these tactics, you’ll probably find a number of potential applicants for your personal assistant position. Some of them may be exceptional, while others won’t come close to meeting your qualifications. That’s why it’s so important to take your time to find the right candidate.  As Joan Burge, author of Become an Inner Circle Assistant, states:
“You can get desperate to fill the position, and then you pay for it later by having to start the search all over again.”
The bottom line is: don’t rush it. You’ve been able to make it this far without a personal assistant, and it’s worth waiting a bit longer to find the right fit. Don’t commit to hiring someone that you’ll only need to let go a few weeks down the road.

Most entrepreneurs spend less time interviewing potential personal assistants than other jobs they deem more important, which can be a tremendous mistake in the long run. Remember, your personal assistant will have access to some of your company’s most sensitive information and be responsible for some of its most important functions. Finding the right personal assistant is just as important as finding the right co-founder, so be diligent in your search.

Screen for Candidates that Will Fit Your Company Culture

There are many talented candidates out there, but they aren’t likely to succeed if they aren’t a good fit for your organizational culture. David Hassell, CEO of 15Five, said that first and foremost you should be screening potential candidates to see how they will fit in with the organizational culture.
“If people don’t have an attitude of ‘this is the most incredible company I can imagine working for and I wouldn’t want to work anyone else’ vs. ‘you’re one of three opportunities I’m looking at’ they’re almost always a ‘No.’”
You can train somebody to use a new project management system or fill out a W-2. However, you can’t train them to have the personality needed to fit in with the rest of your team. According to Russell Glass, Head of Marketing Products at LinkedIn:
“Think culture first.  The right culture fit is easy to train on the right skills, but the wrong culture fit with the right skills will never be successful.”
If two highly successful leaders recommend looking for people that fit into your organization culture – rather than those who have the best skills overall – I think that’s something you definitely need to pay attention to.

Gauge Ability to Take Initiative and Think Under Pressure

Most executive assistants will probably believe that they have the skills needed to thrive at your company. Their references and presentation may be very impressive, but that doesn’t mean they’ll be able to handle the real world problems that they’ll encounter in your company. This is particularly true for personal assistants that used to work in larger organizations, where they had greater access to resources and personnel they could leverage if they had problems.

Startups just don’t work that way. As a result, you need to make sure your candidates can take charge in situations where they don’t have these types of resources available to them. One of the best ways to measure these skills is to ask candidates questions about how they’d handle a hypothetical real-world situation, similar to one they’ll likely face at your company.

For example, ask how each candidate would respond if one of your top clients called to say that they had a serious problem they needed to address with you right away, while you were already in an important meeting with another stakeholder. Listen not just to the candidates’ answers, but to how they arrived at them. The promptness and correctness of their responses can give you an indication of how well they’ll perform under pressure.

Find Out What their Biggest Accomplishment Is

Elon Musk said that he asks every potential hire what their biggest accomplishment is to date. Many other entrepreneurs ask similar questions. You shouldn’t necessarily expect as spectacular of an answer when interviewing an applicant for a personal assistant position as you would when searching for a VP, but it’s still a very important question to ask.

In particular, this question will shed some light on several things that you’ll need to consider when making your hiring decision:

  • The skill sets your candidates consider most important in their new position.
  • Their confidence in their abilities.
  • How detail oriented they are.

Of course, you’ll need to ask follow-up questions to better understand the candidates’ state of mind, as well as the rationale behind their responses. For example, ask why they think their contribution is impressive to determine whether they can provide substantive answers. The most genuine applicants will give you a detailed, thoughtful accounting of their past performance and what it meant to their employers.

Use Leading Questions to Expose Any Flaws

Everybody wants to put their best foot forward when applying for a job, which is why we all tend to focus on our positive traits and either ignore or downplay our negatives. As a hiring manager, though, you need to know what those negatives are. Asking leading questions can help unearth any skeletons that candidates may be trying to hide.

Mark Bartels, the CEO of Stumbleupon, recommends asking applicants what their prior employers will say about them when they ask for a reference. Good applicants realize that any negative issues will come to light anyways, which is why they’ll try to be forthcoming about any problems they’ve had in the past. If a candidate doesn’t reveal issues that a former employer later brings to light, consider that a pretty major red flag against the potential assistant.

Bartels also recommends asking what types of workplace environments people struggle in. The great thing about this particular question is that candidates don’t really know enough about your workplace to try to sugar coat their responses in a way that suggests they’re the right fit for your organization. It’s a great way to get inside their heads and get the real responses you need to make an informed hiring decision.

Conduct a Sample Project

Many people talk a good game during an interview, but that doesn’t necessarily mean they have the skills needed to actually do the job. I’ve talked about this before on this site, but one thing I like to do is have candidates for sales positions try to sell me something during an interview. This lets me gauge their actual sales skills – not just what they think they’re skills are.

You can use a similar strategy when interviewing for a personal assistant. Say you’re planning an upcoming trip (or make one up for the purposes of this sample project). Ask candidates to describe to you the process they’d go through to book your hotel and flights. If you’re conducting an in person interview, you can even ask them to simulate the process in front of you to be absolutely certain they have the skills you need.

Your test project doesn’t need to revolve around travel arrangements – and it shouldn’t if you don’t anticipate your assistant handling these types of duties. If you expect your assistant’s work will involve tax or legal reporting, customer service responses, social media management or data gathering, design a sample task that will measure these specific needs.

Listen Carefully to References

Checking references is a crucial step in choosing a candidate, but unfortunately, it’s also one of the most overlooked.

First of all, you should focus your questions to references on things that actually illustrate the candidate’s ability to handle the job you’re hiring for. You may receive applications from candidates of various backgrounds that seem quite talented, but that doesn’t necessarily mean they have the organizational traits or interpersonal communication abilities needed to succeed as a personal assistant. A candidate’s references can tell you honestly whether or not they’ll be a good fit.

Try to speak to at least a few of the references by phone. Prior employers may be reluctant to sabotage the future job prospects of an employee that they genuinely liked but had to let go for incompetence or a one-time behavioral problem, while others may be limited in what they can say for legal reasons. Pay close attention to the tone of their voice and ask leading questions to see if they’re trying to hide something negative.

Give the Right Applicant Time to Consider the Offer

You’re hiring a personal assistant because you’re overwhelmed with everything you already have on your plate, so your first inclination might be to pick a candidate and ask them to start work as soon as you’ve completed your reference checks. However, being too forward can actually scare people away.

Steli Efti, the CEO of Close.io, argues that people have a hard time making such major life decisions on the spot, which is why the best candidates may turn down such an offer. Responsible people need time to process important decisions. Give them sufficient notice, and allow them a reasonable amount of time to make the necessary accommodations.

Working With Your Personal Assistant

I hate to break it to you, but finding and hiring the right personal assistant is only half the battle.

Personal assistants aren’t mind-readers, and they aren’t going to be able to join your company and immediately get up and running without some serious training time on your behalf. Don’t get discouraged. There’s always a learning curve, even if you’re overseeing an exceptional employee. The following tips may help make the process easier:

Commit to Training Time

It’s tempting to simply throw your assistant to the wolves and have them figure out how to handle the administrative needs of your organization. But that kind of short-term thinking won’t do your business any favors. The success or failure of your working relationship is built on the way you manage the first few weeks of employment.

After your assistant has accepted your offer of employment, but before they begin work, sit down and make a list of the specific tasks you want to transition to them. Rank them by importance and look for opportunities where learning one task will allow your assistant to take on other responsibilities more easily. Train your assistant on no more than 3-5 of these tasks at first and only add on more once you’re confident the work is being completed to your specifications.

Avoid Micromanaging

Training your assistant is important, and you’ll need to commit time upfront to be sure projects are being completed correctly. But that doesn’t give you a free pass to micromanage your new employee.

Renowned career coach and entrepreneur Penelope Trunk points out that a personal assistant doesn’t need as much handholding as many entrepreneurs believe. She said that good personal assistants can learn most tasks on their own through trial and error. In fact, Trunk found that one of her assistants was even able to subcontract work out to his fraternity brothers, proving that the work could be picked up quickly, with minimal instruction.

Your needs may be a bit more complex and, consequently, require more training, but it’s still important to remember that you hired your assistant for a reason. Micromanaging wastes the time you’re supposed to be saving, so do your best to leave your assistant to their own devices whenever possible and resist the urge to micromanage them.

Communicate Your Expectations Clearly

Even the best personal assistants won’t be able to do their job properly if you don’t communicate your expectations clearly. Here are a few things you’ll need to do to make sure the arrangement goes as smoothly as possible:

  • Try to make sure that the system you create is implemented as consistently as possible. Having different expectations across different projects results in confusion for everyone.
  • If you need to make changes to the processes your personal assistant will need to follow, do your best to communicate the reasoning behind the changes. Your assistant will have an easier adjusting to your requests if they understand the need for changes.
  • Ask if they need any additional resources to either complete their work or expand their skill sets in a way that benefits your organization.

It’s a lot of work, but ultimately, you’ll be glad you took the time to set your personal assistant up for success. If you do so, your assistant will be much more committed to their job and require less involvement on your part as they acclimate to their new responsibilities.

Always Accept Feedback from Your Assistant

Recently, I had the pleasure of interviewing Ryan Carson, the CEO of Treehouse, who has created a very efficient business model that allows everyone to work four days a week without reporting to a manager. There are a number of steps that Carson took to create such a seamless business structure, but one of the most important was accepting feedback from employees.

If you want your business to run smoothly, you need to seek regular feedback from every member of your team – especially your personal assistant. Your assistant creates a direct line of communication between you, your employees and many of your customers, and as a result, their feedback can be highly valuable for your personal productivity and your startup as a whole.

Just a word of caution, though. The feedback you hear may not always be positive, especially if you’re new to managing employees. Try to not get defensive. Instead, look for opportunities to improve yourself. Your business will benefit as a result.

Evaluate Performance with the Rest of Your Team

Evaluating every employee’s performance is a fundamental part of management, which is why you’ll need to make sure your personal assistant is staying on top of their responsibilities and acclimating well with the rest of the team. They may seem to be doing well from your point of view, but it’s important to touch base with other employees to get their feedback.

If they bring any issues to your attention, take them under advisement and use them as opportunities to coach your assistant. If you’ve chosen the right assistant, they should be motivated to improve. If you find that they’re resistant to feedback, consider carefully whether or not you’ve made the correct decision and remember that it’s often better to cut ties with the wrong employee quickly than it is to drag out a relationship that’ll eventually fail.

Invest in Hiring and Training the Right Personal Assistant

A personal assistant may not seem like the most essential job right now. If you’re already wearing the hats of a marketing department, R&D team and accounting service, it may seem like hiring these roles directly will help you move forward more quickly. But if you hire a personal assistant it can do wonders for your business and make your life much easier – as long as you hire the right candidate and give them the training and resources that they need.

Do you have a personal assistant on board helping with your startup? Feel free to share what you’ve learned from the experience and what tips you’d give other business owners in the comments below: