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How a Clandestine Las Vegas Birthday Party Changed My Approach to Hiring

Written by: Sandra Lewis

A while back, a longtime Boldly client emailed me:

“You guys have built such a high-quality remote team. What tools did you invest in to measure and assess the performance of your remote staff?”

It was gratifying, of course, to receive that kind of feedback. But it also reminded me how far we’ve come. During our first year in business, we had more quality problems than I’d like to admit. And if there was one thing I learned, it was this:

While measurement and collaboration tools can be helpful, they’re no substitute for hiring team members you can actually trust.

The best companies scale on trust, not performance monitoring.

Disappearing Team Members And All-Nighters

When we first launched Boldly in 2009, virtual teams were on the rise, and remote-worker monitoring was a hot topic. After all, how would you know if that Upwork designer wasn’t billing you for time spent watching TV?

As a result, apps for tracking remote workers began emerging — some actually captured screenshots of remote workers’ computers to keep them honest.

As someone new to building and managing remote teams, I was naturally concerned about performance. But in the rush to supply early customers with business support specialists, I didn’t have the luxury of designing a rigorous process for quality control. I was basically posting jobs on various platforms that targeted remote workers and began delegating work to people who sounded competent.

Thankfully I have an innate sense for good talent, but disasters occurred more frequently than is acceptable.

For example, one day, a remote team member in Colorado disappeared without a trace, leaving me with 30 hours of unfinished voice transcription work. My co-founder and I toiled into the wee hours that night to complete the project ourselves.

Why Remote Monitoring Apps Don’t Help

Desperate to avoid more all-nighters and even one disappointed client, I invested in one of those tracking apps. After all, if I could monitor progress, wouldn’t there be fewer surprises? I asked our team to start logging their hours and send screenshots of their work.

Unfortunately, tracking had virtually no impact on quality.

For one thing, enforcing compliance — making sure everyone was actually logging hours and sharing progress — turned out to be a lot more time-consuming than I had expected. Worse, it quickly became clear that screenshots and time logs gave me zero insight into the quality of the work being performed.

It finally dawned on me: if I was spending so much time keeping people honest, maybe I was hiring the wrong people. What if I devoted more time and energy to evaluating those people before bringing them on board?

Screening For A Sense Of Ownership: The Lie In Las Vegas

In my initial attempts at better screening, I focused solely on skills — and the results were still hit and miss.

One woman I hired, who had all the right qualifications, later emailed to say she couldn’t complete a project because she had been hospitalized with acute appendicitis. After sending flowers, I logged into Facebook to discover 25 photos of her escapades at an all-night Las Vegas birthday party!

Needless to say, I never heard from her again.

Of course, many team members I hired turned out to be superstars. They went the extra mile for clients, did amazing work, and never missed deadlines.

One day, I decided to analyze these “lucky” hires: Was there something they had in common that I could screen for in new candidates?

It turned out there was. While these people had the necessary skills, they also demonstrated a clear sense of ownership of their work. As one of those high-performing executive assistants once told me, “I’m not doing my best work for your sake. I’m doing it for mine because it matters to me, and because I want to retain both my clients and this lifestyle.”

How I Hire People Who Share Our Values: “Everyone Wins”

The only way to successfully grow was to find a way to hire remote team members who shared that sense of ownership. Specifically, we needed people who wanted our clients to win, who wanted us to win, and — just as importantly — wanted themselves to win.

The funny thing is that, from the moment we founded the company, “Everyone Wins” was one of the core values we identified. But for some reason, we never intentionally screened for it. Clearly, that had to change.

Over the last decade, as the Boldly team has grown to more than 100 administrative professionals throughout North America, the UK, and Europe, “Everyone Wins” has been the key to maintaining the quality of our team.

Here’s what I look for, and some techniques I’ve developed to spot it:

#1. Wanting others to win

One question I often ask candidates is, “Tell me about a time you were successful.”

Many people answer by speaking only about themselves. I look for candidates who credit collaborators — subordinates, peers, mentors, or managers — for their successes. These people tend to be cheerleaders, people who actively support others to make great things happen.

#2. A desire to win for oneself

To date, we’ve connected our clients with business support specialists who also happen to be military spouses, parents, and expats, all of whom find the flexibility of remote work appealing.

For example, we have a number of longtime team members who have moved from state to state for a spouse’s military postings, and we give them the chance to maintain a steady income while building a rewarding career. Without exception, our best performers made it clear from our earliest conversations that they had a personal stake in succeeding at their job.

#3. Passionate personal interests

We ask clients and executive assistants to approve matches before working relationships begin. Having them meet and get acquainted extends our sales cycle (and sometimes we have to delicately handle rejections), but the long-term results are always better for both sides. These matches work best when the Boldly assistant shares a personal passion for — and experience in — the client’s domain.

#4. Curiosity about how our team defines success

Now that we’re better at hiring people who share our values, we don’t have to tell them what to do. Rather, when one of them has a challenging situation, instead of telling them what to do, we ask, “How can we help you succeed?”

This is also the question we want our executive assistants to be asking our clients, so I like it when candidates ask me questions about how we define success.

#5. Positivity

Our best people have always seen challenges as opportunities to learn and solve problems. So during interviews, I pose challenges for candidates to tackle. Of course, the solution is less important than the candidate’s demeanor.

Some people are clearly overwhelmed by a tough challenge; others light up at the chance to make things better.

Ultimately, Great Teams Scale Through Trust

When you define core values and base hiring decisions on them, you have a much easier time trusting the people on your team. That’s certainly what has happened at Boldly.

That’s not to say that problems never arise. But when they do, it’s comforting to know that firing someone probably isn’t the answer. Just last month one of our managers called to say she was struggling to meet one of the performance targets we had established for her.

When I asked what I could do to help, she said, “Honestly, I’m worried you think I’m not working hard enough.”

I told her what I now say to everyone on my team: “I hired you because I trust you.” She smiled, and the tension in her shoulders disappeared. Then she went back to doing great work.

Later that month, she smashed through her performance target.

This article was originally published on

Topic: Remote Executive Assistant

Updated on August 10th, 2022

About the author: Sandra Lewis is the Founder and CEO of Boldly. She's passionate about helping founders move their business forward with the right skills and resources. Setting an example of the efficiencies gained working virtually, she manages her entire team on a virtual basis.