My Detailed Notes From Hiring An Assistant On Upwork

A few months back I hired a virtual assistant on Upwork; she’s a star.

In total I shortlisted 19 candidates, and interviewed 13 (11 women and 2 men, which was roughly the same ratio of applicants). The average call length was 13 minutes 57 seconds. This post includes my detailed notes on each of the candidates I interviewed, including their strengths and weaknesses. This post is just one perspective, mine, and my hope is that it will help you succeed in your future applications.

First, a little about the job I hired for…

Why Having a Virtual Assistant is Important to Me

I came to Upwork to find a virtual assistant to help with my personal website. Work tasks include uploading my essays to WordPress, transcribing podcasts, managing calendars, etc.. I posted this as an intermediate level job (mid-ranged experience, mid-ranged hourly rate), for less than 30 hours per week, for a duration of six months or more.

But my goal isn’t just to complete these projects, my goal of hiring a virtual assistant is to:

  1. Give me more leverage on my time. I have my own work projects and obligations, so I’m looking for someone that can help take a little off my plate. I’d like to optimize my time for writing and consulting, so it’s great for someone to help with the elements that tie those together.
  2. Do it better than I can do myself. I’ve heard some employers talk about passing off “low level work” to their assistant, but I don’t think of it that way. The work virtual assistants do is incredibly valuable and important to my projects and personal brand. Every item, from formatting an article to replying to reader comments to invoicing is critical.
  3. Help me improve my work. My strengths are in project growth and writing. I believe having a great virtual assistant can augment my strengths with their own. For example, the freelancer I hired has excellent organization skills, so can help keep me on task and on deadline for projects.

Okay, enough about me, here is the review of the thirteen awesome candidates I interviewed. These are my raw notes, with a little bit more added for context. I’ve changed the names to what are generic names in North America to respect each candidate’s privacy, but the substantive feedback is the same.

Candidate #1: Helen, Kenya [10:00am]

  • The first applicant for the job! Being fast helped her stand out.
  • She didn’t message me at 10am. I had to message her at 10:02am.
  • We called via Skype. It was a slow connection on her end. I don’t want to penalize her for this, and I understand that international may not have the same access as us, but it was an indication that working together may be a challenge.
  • A few minutes into the call, she said “can I call you back in a couple minutes because I’m getting out of the car.”
  • I’m not sure why she wasn’t ready for our call, because she didn’t explain.
  • Again, with empathy for any reason she may have, my expectation and hope was for a reliable call. It was 6pm her time.
  • A lot of lag on the call, so we switched to text chat. She is a fast typer!
  • Her answers were short and literal, so didn’t tell me much. E.g., I asked about her passions outside of work and she just said one word, “travel.” I expect this could have been a cultural difference, but my expectation was to learn a little more about her.

Conclusion: I would love to work with folks abroad, but we need to have reliable communication.

Candidate 2: Zach, Canada [10:30am]

Note: Zach and I connected via another job site, and he was the only non-Upwork candidate.

  • Stood out because really customized intro message. He researched me, shared some of his personal story, etc.
  • Emailed me an hour early to say he would be out, so can we please switch from Skype to phone call? No problem! Great to have the advance notice.
  • He is currently commuting between two major cities, tired of the corporate world, etc. He wants to eliminate his commute and realign to working for nonprofits. He felt like a kindred spirit.
  • He has hustle: he built a restaurant business from the bottom up.
  • He is tech savvy: he built his own site on WordPress, and one for his SO’s art business.
  • He is focused on productivity and learning: uses a calendar to intentionally schedule his time.

Conclusion: Great candidate and I think he could help with my projects, but the admin work may not be a great fit for him.

Candidate 3: John, American Abroad [11:00am]

  • Very strong candidate from initial message. Like Zach, shared his personal story and researched me to really customize the intro. He told me that he connects with my mission.
  • I pinged him at 11:00am, no response until… 11:07am. He was running behind, in another meeting, and asked for another five minutes. Totally understandable! But I wish he had messaged me a little earlier so I wasn’t waiting.
  • He has diverse interests, and gave me a lot of info for each answer.
  • Seems to have high level tech abilities. He made a massage business more automated with emails, scheduling, etc.

Conclusion: It was a nice honest convo. I think he’d be great to have lunch with. Like Zach, I’d love to work with John, but I don’t think my current position is a great match for his skills and experience.

Candidate 4: Belinda, California [12:00pm]

  • From her application, one of the strongest candidates skill-wise. She has a strong research background as a paralegal. Plus certifications from Udemy in digital marketing, content, project management, etc.
  • She has volunteered for charities that help women all over the world. I love this and want to support it.
  • She is a people person, loves people, social, travelling.
  • She was very friendly, but IMO a little too casual, I’d like to have someone that is very professional on the phone incase I need them to call my clients, etc.
  • She said, “this is my dream job” – Awesome!
  • Good framework for the convo. She focussed on productivity and organization. She wants to have clear goals and ask what the client wants. A lot of clients don’t know what they want or need, so she will proactively step up to help.
  • Each client: contract, proposal, so both on clear page, and weekly update by phone or email. Great! I love the organization.
  • She works around the clock sometimes, even for free. Wants her clients to succeed. Wow!
  • Her questions for me were GREAT. She asked what I need from the role, and followed up with “here’s how I can help based on that.”
  • She has people behind her, to edit, proofread stuff, check over things. Has network with web developer, social media manager. That’s all tied in with regular rate. It’s not about money, they help her out she helps them out.

Conclusion: Very strong candidate and I expect would be great to work with. Only criticism was that she was a little too casual on the phone. I’m not sure if three-hour time difference would be an issue.

Candidate 5: Cailey, Canada [1:00pm]

  • Told me about her social events projects: events to raise money for charity. I love it!
  • Was in insurance. Wants to work from home and travel more.
  • Started her own social media company, has a few clients. Learning and developing more skills.
  • Passionate about helping people, like small businesses using social media. Her favorite client is a pet apparel Etsy shop.
  • Cailey is tech savvy. Built her own site on Weebly, she says “not the best site, but learned.” Also, Canva, any social media, planning tools., etc.
  • Uses Trello for self. Keeps organized there with weekly to-dos for each client, projects, etc.
  • Asked great questions about my goals, hours and expectations, communication preferences, etc.

Conclusion: Another great candidate. No real qualms. I’d love to hire her. (I ended up referring her to a friend and they are now doing regular work together.)

Candidate 6: Jessica, Canada [2:30pm]

  • New mom, so her priorities changed. She gave up career and is looking for something to do from home.
  • Doesn’t want her talents and skills to go to waste. I admire this.
  • Loves online marketing. Started a FB page for her new jewelry business.
  • Working with clients, experienced with technology.
  • Temp worked for investment company.
  • Very marketing, SEO focussed.
  • Very diverse, learning focussed, accounting, marketing, etc. Also creative side.
  • Willing to experiment with tools to improve productivity.
  • Seems capable but very, very casual on phone.
  • Spoke over me a few times.

Conclusion: Good candidate. Likely capable of doing the work, but similar concerns as others with phone manner.

Candidate 7: Kim, Canada [6:00pm]

  • She messaged me at 5:52pm to reschedule a 6:30pm meeting. No explanation and I haven’t heard from her since.

Conclusion: Easy to exclude.

Candidate 8: Amy, Florida [Day 2, 2:00pm]

  • Answered, “Hi, Amy speaking!” – I love this, it’s a small pet peeve when I have to ask, “is this Tina?”
  • Very passionate interests: music! piano! singing!
  • Well spoken, talks about expertise like an expert. Music theory and how it works. Enthusiastic.
  • Plans for career: business and marketing.
  • Why studying music + business? That combo makes it accessible to her.
  • Work projects: some writing projects, social media. She worked with a social media company and their messaging wasn’t working, so she fixed it. It was such a good fit that client asked her to template it so other freelancers could follow.
  • Started taking on more clients, difficult to keep track of everything to do. Learned Trello, uses it for projects.
  • Generally organized person, but too many deadlines. Went and bought big planner, will list everything to-do, break it down into different days and then check them off one by one. Great!

Conclusion: Great candidate. Phone manner was friendly but professional. Smart and organized. A little less experienced than some of the other candidates. I offered her a test project, but cancelled the contract after multiple delays and a partial delivery.

Red Flag: I asked applicants to include the words, “I love charity” in their application so I would know they read the job description. Amy didn’t include this.

Candidate 9: Fiona, Michigan

  • Friendly, clear answers, though a little long.
  • Passionate about oil painting.
  • Working on: school, theatre, music, performance, etc.
  • Technology: learned how to use iOS light board to program lighting for a show.
  • Productivity: does voice recordings during car rides.
  • Asked me about the specifics of work, e.g, recording podcasts.

Conclusion: Great candidate. I sent her a test project to complete and she set her own due date. On the due date she emailed me to say that she was unable to take on my project due to a personal matter.

Red Flag: I’m not sure. Fiona seemed like a good candidate but I wonder if someone with a part-time focus will be able to make this work. I’m not against hiring students, but this is something I will ask about in the future.

Candidate 10: Mona, California

  • Passionate about food. Moved to Cali and didn’t realize how many foods in the world hadn’t tried yet.
  • Has been working on a lot of video game stuff, reviews of games, editing, etc.
  • She takes a deliberate moment before answering questions that I’m not sure about, e.g., “What am I working on? Hmmmm”.
  • Seems very young. Has four associates degrees.
  • Got more comfortable and had more fluid answers about halfway through the call.
  • Technology: Freelancing for variety of different clients, use a variety of different things: editing, streaming on Twitch, using Trello, etc. LOVES Google docs because of editing feature. Yay!
  • Productivity: Single mom, she says making the most of couple hours = very important. Created a designated work area. First two years freelancing, did it half heartedly, didn’t know if would be lucrative enough to do full time. Def. get out of it what you put into it. After, able to create space, desk, own area, set work hours, younger daughter has care.
  • No questions for me.

Conclusion: Seems very smart and capable. I have a soft spot for single moms and if I can give her good work then great! I sent her a test project and then didn’t hear back. I ask candidates to set their own due date for test projects and she didn’t respond to that.

Red Flag: Lack of focus. Non-responsive.

Candidate 11: Melissa, New Jersey

  • I did this call just before a family dinner, so was a little distracted.
  • She is passionate about funding the arts, artists being able to support themselves and create etc.
  • Has done project management stuff and is now looking for real world work because recent graduate.
  • Loves Trello but her teammates wouldn’t use it.
  • Productivity: Using calendars to set schedule because not in school anymore.
  • I don’t recall what questions she had for me.

Conclusion: She seems good. I sent her a test project and she said, “great, I’ll start on this tonight!” Melissa did well on the test project and we worked together for a few weeks, then I cancelled the contract because the work wasn’t getting done on time and communication was slow.

Candidate 12: Kimberly, American Abroad

  • Passion: education and travel, it helps point her in direction for future. Ultimately teach high school about business and life direction.
  • Becoming passionate about education, well rounded.
  • Why move to France? BF in military.
  • Did auditing for gov entities and non-profits.
  • Spent some time traveling: Indonesia, Hawaii, etc.
  • Visa in France doesn’t allow her to work in France. Language also a barrier. Moving to online work, a couple hours per week.
  • Organized software at accounting office to get everyone on board for how to operate that software.
  • Productivity: Moving abroad, aside from one job, have different ways, calendars, apps, to-doist.

Conclusion: Seems very smart and capable. Worked as professional in industry with high standard of detail and organization (government audits!). New to remote work so seems willing to learn and explore. I sent her a test project which she did well on.

Candidate 13: Amanda, New York

  • Recognized my phone number as from NY, asked about it.
  • Visiting friends, college, service learning program, harder to do now, but creative writing program for underprivileged students, loves working w/ the kids, really fun, doesn’t take as much time as would like to, want to get more into it, passionate about learning ins and outs of non profits.
  • Used to do freelance writing, little projects here and there. Not using full potential, wanted to connect more with clients, know the identity, working for content mills, 1000 word pieces, no connection to the company, now writing with clients more, look at overall strategy etc.
  • Talks a lot, lots of specific examples. Lots of passion.
  • She gave an overview of my site that showed deep understanding. Great!
  • Asked about podcasts content.
  • Told her about side project, next steps, etc.

Conclusion: Probably the most experienced freelancer that applied. Suggested rate was higher than I had in mind for this role. She is willing to negotiate.

So, who did I hire? I’ll share that in a minute. First, one quick point: notice that very little of the feedback above is about money. I wanted to evaluate each of the candidates on merit first, to make sure they are a great fit for the role I have available. The rate is relevant, but was a secondary consideration.

I hired #12 🙂

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