Boldly Executive Assistant Interview Questions
& Process

This company's hiring process is really thorough and challenging because it's a very competitive place to work. Even if you're a super talented and experienced assistant, you might not get through their tough interview stages. You need at least 7 years of experience to even apply. If they like your application, they'll email you a series of questions. The first email thanks you for applying and stresses that it's a part-time role (up to 25 hours/week, with potential fluctuations based on client needs) and you must commit to at least 20 hours. They'll ask if you understand this and why you're moving from full-time to part-time, noting there's no guarantee of exceeding 25 hours. The fourth email explains that hours start slow (maybe 5-10/week) but ramp up quickly, asking if you're okay with that, while still requiring a 20-hour minimum commitment. The second email states the hourly pay rate, possibly like $22 ($22-$24). They want long-term employees, so read email questions carefully and respond precisely. Around the third email, they'll ask you to create or copy your resume into Google Sheets and format it to match your original resume within 24 hours. If you pass that, they'll ask if you want to proceed to an automated video interview (Kira Talent), which you have 3 days to respond to. Make sure you've watched all videos on their website (Careers, candidate requirements, Open Positions, About Boldly, FAQs, Inside View, Boldly Benefits) and truly understand their company model – you'll need to explain it like you're telling a friend. The automated video interview is about 30 minutes. You'll register, test your equipment, and take an assessment to get familiar with the format. Questions are presented verbally, you get about 30 seconds to think, then a short countdown before a 1-minute recording. You can take a brief break between questions. Dress professionally, ensure a clean background, and good lighting. A downside is you can't elaborate or change answers like in a live conversation; it's one and done, which felt impersonal. There are 6 questions in total. Knowing the company inside and out is crucial, especially their client-matching model for long-term relationships. If you pass the video interview, you'll have a Zoom call with the Recruitment Manager, Devin, followed by a video interview with the founder, Sandra Lewis. After all that, you must provide 3 supervisor references from the last 5 years, and background checks are done if an offer is extended. The whole process spans several weeks. This experience didn't result in an offer, but the goal is to inform others about the exact steps involved. If you're up for this extensive process, go for it; otherwise, there are other remote opportunities available.

The interview process took about a month and involved answering multiple emailed questions that were often repetitive. There was a strange Google Sheets exercise, followed by an automated video interview with six questions. After that, there was a video interview with HR, and then a final video interview with the founder, who was late. While the process seemed to go well and they were encouraging, they would ultimately decide you weren't a good fit. This is why they have a low score in this area: they ask a lot from applicants, especially concerning their time, for a remote, part-time, 1099 contractor role where the only real benefit offered is flexibility.

I got an email after applying online and chatted briefly with a nice person. They said I'd get a task to test my skills, which turned out to be transferring my resume into a spreadsheet. It was weird because it didn't really show spreadsheet skills, but I did it. After a few days, I passed that and was told to expect a 'taped video interview.' It had about 5 questions, mostly normal stuff, but the last one was a totally weird personality quiz asking what kind of cake I'd be. Those questions are so annoying and feel like fake science. Still, it was an interesting process, and everyone was polite. I got a standard rejection later, which is fine since these jobs are competitive. I'm calling it difficult because it took weeks, the spreadsheet thing was odd, and the cake question was baffling.