Four Tips for Hiring Digital Team Members

Four Tips for Hiring Digital Team Members

Perhaps entrepreneurs often have a hard time letting go of the reins in their business because we’ve put our blood, sweat, and tears into building a solo business. If you’re successful, though, there will come a time when you cannot handle it all on your own. When done properly, outsourcing can be a beautiful thing.

As your company grows, you may need help with administrative tasks or managing projects so that you can focus on your true zone of genius. Some of the most common ways to outsource initially are to engage someone like:

  • A project manager
  • A virtual assistant
  • A bookkeeper
  • A social media manager

If you have a bad experience hiring someone, though, you may get burned and decide that outsourcing is a nightmare. That’s why you need to do it the right way by following these tips.

Ask for References First

There are many places to find virtual helpers- Facebook groups, job boards like Upwork, and referrals. If you have a choice, pursue referrals first. Someone you know is unlikely to send you an inexperienced or unqualified virtual employee. This is often the way that I have found the best help.

Conduct an Interview

Before hiring any virtual team member, you should interview the person first. Ask questions like:

  • What has been your favorite virtual position to date?
  • Tell me about a time you encountered a challenge working virtually and how you handled it.
  • When you make a mistake, what do you do next?

Use a Test Job

Before investing in a big retainer, give someone the opportunity to meet and exceed your expectations. If they miss the deadline or don’t work well with your communication style in a smaller, 1-3 hour job, there’s a good chance it’s the wrong fit. Unfortunately, sometimes even a person who seemed like the best fit on paper and in the interview just doesn’t live up to your expectations. I hired a pricey high-end VA earlier this year and was really disappointed because I did not use a probationary period to measure results. Lesson learned.

In cases with my most successful VAs and team members, the trial period is my opportunity to test out 3-4 people and identify the right fit. I did this recently when interviewing four separate people for an opening on my team. I ended up finding two people who were perfect for different roles, and both met and exceeded my expectations with the trial run. I couldn’t bring them on in a bigger role fast enough. Meanwhile, one of the people I thought would be the best just didn’t do well with the trial and missed a deadline by four days. Always, always give someone a chance to prove themselves! The right people will make a solid effort to impress you.

Two years ago, I hired ten writers for a test project of one blog each. Two never completed the project at all. Two duplicated content, and among the remaining six, two were superstars that I worked with for a long-term engagement. Sometimes the only way to tell who is the right fit is a test job.

Give Outstanding Directions

Aside from situations where the person hired thought it was an easy gig where they’d collect money for no work, 90% of the communication breakdowns between virtual team members and clients has to do with instructions. Bad instructions should always prompt the contractor to ask for further information, but in a new relationship, this might not happen easily and then everyone’s disappointed by the experience. Here are my recommendations for giving phenomenal directions:

  • Provide a sample of what a completed outcome or goal looks like
    • “The CTA at the end of the blog should always prompt someone to book a call with me.”
    • “Each month, I’d like 200 new followers organically on my Facebook page.”
    • Use video screencapture to show you working on your screen. This means that you can create video instructions one time and use it with all new team members. Someone who needs to review multiple times is not emailing you ten times to clarify but can instead watch the video again.
      • Use the free version of Screencastomatic for up to 15 minutes of recording, or shell out the $15 for the premium version and upload videos with a password for videos on their site for videos of any length (and a great cost-effective option for making online courses, too!)
      • Use a trello board or Google Drive folder for all your training videos and have each new team member review your materials so that you can save time
      • Own up to your mistakes and use it as a learning opportunity.
        • Even with your best efforts, mistakes will happen and deadlines will be missed. When this occurs, rather than totally blaming the contractor/employee and cutting the relationship, figure out what you could have done differently. Did you overload the team member? Give poor directions?

Your virtual team should be made up of people who support you and make your life easier, not more difficult from an administrative perspective. In an ideal world, your team captures mistakes and opportunities to grow before you do because you treat them as a valued member of the team.

Four Tips For Hiring Digital Team Members
Four Tips For Hiring Digital Team Members

Laura Pennington is a writer, freelance coach, and online course creator. She’s managed digital teams for companies like TrueCar and Microsoft and previously managed a team of writers creating more than 400 blogs every month. She gives advice to new and emerging freelancers at and

Twitter: @sixfigurewriter


Four Tips for Hiring Digital Team Members
Four Tips for Hiring Digital Team Members