When you’re looking for innovative and action-driven talent, why not open your doors up to people that have already pioneered their own lives?

Finding Top Talent: Stop Looking Inside a Box for People Thinking Outside of One

I was recently contacted about an opportunity. On many levels, this opportunity “checked all the boxes”, but there was one caveat: I’d have to move to San Francisco. For many (including a previous version of myself) that would be a dream. But for current me, it would mean throwing away the very life that I had spent the last 3+ years intentionally building.

Despite having spent over 10 months looking for the “right” remote job back in 2015 and now living the life I had long envisioned, I would be lying if I said that I didn’t seriously consider the switch. The lure of money, connections, and “the valley” was cogent.

Yet, when I thought about what I truly wanted and prioritized in my life, it became immediately clear that I’d be trading down. More specifically, I’d be trading the freedom to optimize my life for one that was predominantly determined for me.

Ultimately, I turned down the role, which of course prompted the company to continue to look for the right person to bring onsite. That response?while completely logical?got me thinking…“Will they be able to fill the role?”. The obvious and correct answer is yes. But what sparked the question was the realization that they were looking “inside a box” for someone who is already thinking outside of one.

Looking Outside of the Box

In the digital age, many companies cite their greatest challenge as the imminent “war for talent”, due to the imbalance of supply and demand, resulting from the widening skill gap.

With the speed of change in our workforce increasing, companies see “winning the war” as the only way to stay innovative and ahead of the competition. Their solutions result in ping pong tables, salary wars, and ridiculous inflation within tech hubs, in an effort to attract top talent.

As companies place higher importance on attracting, recruiting, and retaining top talent, I wonder whether some companies are missing a big puzzle piece. I ponder whether the companies that couple their highly developed vetting processes with a need for onsite talent, are not only limiting the sheer number of candidates, but perhaps the best? I can’t help but wonder if they’ve eliminated a significant chunk of individuals who are already living in the very future that these companies are hoping to create.

Do you see the disconnect?

Company: “We need someone who has proven their ability to execute. We’re looking for people who see things differently; people who think outside of the box and create innovative solutions.”

Recruiter: “Great, how about someone who lives in Poland? She moved there to be with her husband, so that they can raise their daughter together. Flexibility has allowed her to bootstrap a company to an 8-figure valuation, but she just sold it and is looking for her next challenge”.

Company: “Sorry, we can’t do remote.”

Finding Top Talent: Stop Looking Inside a Box for People Thinking Outside of One
Discovering gravity “outside the box”

Although I can certainly recognize my own bias, it confounds me that companies are willing to auto-eliminate a group that I’d consider diverse and forward-thinking; a group of people who have already creatively redefined their world.

Put simply, these individuals literally looked at their lives and thought, “There must be a better way”, and then took the initiative to impact change. As more companies search for “creative ways to recruit employees”, I can’t help but wonder if they could develop a strong, yet overnight, competitive advantage by simply opening their doors up to the remote workforce.

The Remote Affinity Ratio (RAR)

The first step in evaluating whether you should be more open or less open to working or hiring remotely is identifying the potential bias you may have towards this new way of working.

I’ve personally been working remotely for the past 3 years. That may not be a significant amount of time for most people, but it’s actually represented 75% of my experience in the full-time workforce. In many ways, it’s all that I can remember.


As I started to further consider the concept of quantifying someone’s affinity or openness to remote work (and perhaps new ways of thinking or living), I conceptualized the “remote affinity ratio” or RAR.


Put simply, it’s the ratio of: years worked remotely and total work experience.

RAR = (# of years worked remotely) / (# years in workforce)

The metric is not intended to be one born out of competition, but instead to reflect on how one’s prior experience may impact one’s openness to new working norms.

With this lifestyle so ingrained in the way I operate, I need to keep in mind that much of the world still does not operate this way. So while it surprises me when individuals or companies are completely closed off to the concept, when I think of the timescale that others draw their context from, it starts to make a little more sense.

As a simple example, picture the life of a 55 year-old, who’s been in the workforce for 35 of those years and the comparison of their “world” compared to the picture of my own that I drew above.


Even if this individual works remotely for three years, it only represents a single digit percentage of their career and therefore a majority of their perception will still fall outside of this new approach.

When compared side-by-side, it’s not surprising that it’s easier for me to visualize a different way of working and living. Not because I’m better, smarter, or more creative, but because I have lived this new approach for longer and I have fewer barriers in seeing past decades of prior experience. My viewpoint on how things should work isn’t solidified yet.

RAR is a metric which is purely meant for reflection; to try to understand how our experiences accumulate to form our perception of what is or isn’t possible/better/optimal.

So to those who are still remote-averse in their quest towards finding and retaining talent, consider whether the concerns are founded in experience or historical perception. More importantly, is your perception a reflection of where the world is today or your RAR?


With the concept of RAR in place, I started to think about some of the fundamentals of remote work and what someone with a high RAR may deeply understand, yet may be invisible to those with limited exposure. I honed in on three ideas that seem to be the most nascent:

  • By convention, remote workers tend to think outside of the box
  • Flexible work incentivizes people to optimize and improve
  • Survivorship bias impacts the way people view remote work

With a deeper understanding of these three points, I truly believe that hiring managers may be more open to the concept of hiring remotely because of the positive tradeoffs that exist in enabling a larger, more innovative talent pool.

Innovation Nation

TechCrunch recently published an article claiming that remote workers and nomads are the next tech hub for innovation. A few weeks later, Stripe declared that their next engineering hub is… remote! It’s no secret that companies are capitalizing on the intersection between innovation and the distributed workforce.

By simply giving someone the freedom to replace a commute with other things, they not only have more time to innovate, but are left less exhausted and more inspired. These individuals have not only started thinking outside the box, but living outside of one (a cubicle) as well.

Remote work enables people to start thinking creatively about how they get their work done, but also invites people to optimize past that. Many take that opportunity to consider how they can improve their mental and physical health, finances, business opportunities, and more. Consider the overlap between digital nomadism and things like financial independence, technology, entrepreneurship, minimalism, and investing here. The creative force of the remote revolution has pushed people to innovate across each of these domains, resulting in entirely new concepts, like FIRE.

Finding Top Talent: Stop Looking Inside a Box for People Thinking Outside of One
Visualization of related subreddits to r/digitalnomad

Many people are familiar with Peter Thiel’s famous question from Zero to One:

“What important truth do very few people agree with you on?”

Thiel, in effect, is attempting to isolate how individuals think. While Thiel’s question may unearth intelligent or creative minds, I would argue that an even better way of isolating those who are able to predict the future would be to find talent who are currently living it.

The Wrong Incentives

Suppose that you have a series of plants that you no longer have the capacity to take care of yourself. You have two options:

  1. You can offload your plants to individuals who will come into a specific location to water them. This location has the exact amount of water and sunlight to keep the plants alive. The plants likely won’t die, but they certainly won’t flourish. The good news is that you can watch those who you’ve hired come in and water the plants.
  2. You can opt to have other individuals take care of your plants. These individuals have more resources and can optimize them as they see fit. While you can’t watch these individuals water the plants, you can pay them based on their successful ability to get the job done well. The success of this working relationship is built on trust and impact.

Finding Top Talent: Stop Looking Inside a Box for People Thinking Outside of One

Now imagine these plants as your company. These scenarios are not so unlike the comparison between hiring individuals “in-house” and giving employees the freedom to work remotely. While the second scenario may result in some dead plants (or terminated hires), what is more likely to happen is that the individuals will appreciate that they have the space to operate and produce results. Meanwhile, the first scenario still has ample potential to result in dead plants and can only ever achieve the maximum potential that you’ve predetermined.

Here’s the thing that a lot of people don’t acknowledge about offices: you literally have no incentive to improve. When your day is ultimately tethered to the number of hours you need to be there, why decide to be more efficient?

  • Why bother producing higher quality work?
  • Why bother improving your workflow to half the time it takes to do a task?
  • Why bother developing 2x complex solutions that deliver 10x impact?

Why bother being better, quicker, or more optimal? Why bother.

This concept, of not giving people space to innovate and create their own path to impact, compounds further.  

Why? I fundamentally believe that once you get someone to start considering how they can work more optimally, this permeates into other aspects of their life. They have now trained their brains to remove noise and optimize toward impact. This will inevitably impact the way an employee engages with problems they face across contexts.

In short, by enabling remote work, you are inadvertently training your people to improve the way they think and how they can achieve more. Most importantly, you are giving them the space they need to get there.

Survivorship Bias: Searching in the Wrong Places

Still not convinced? Let’s talk about survivorship bias.

When I go to coworking spaces full of nomads, I’m always impressed by quality of people that I meet. While there is always a distribution, a majority of individuals are looking to improve their lives in some way, whether it be starting a new business, learning a new skill, investing in a better diet, or looking to develop some form of a better habit.

When I hear of significant swaths of industry being apprehensive of remote workers, I can’t help but wonder if some survivorship bias is at play.

For those new to the term, survivorship bias is: the logical error of concentrating on the people or things that made it past some selection process and overlooking those that did not, typically because of their lack of visibility.

In this context, consider that individuals with a bad experience working with remote workers will likely be the loudest. Similar to the insurance industry, people are quick to report and amplify a bad experience, while being perfectly content to tread silently when multiple positive experiences happen.

“Studies have shown that the most vocal customers are the ones who’ll express their feelings. Everyone else will either give companies another chance or just leave.” – Walker Donohue

Instead of treating negative experiences as an outlier, these amplified experiences become the narrative for others. In insurance, if a few claims are processed slowly, their Trust Advisor rating is 2 stars. With remote work, if a few individuals are unaccountable, the entire distributed workforce is deemed undependable.

Finding Top Talent: Stop Looking Inside a Box for People Thinking Outside of One
The “voice” of a negative experience is often most amplified, impacting the perception of those who have yet to form an opinion based on their own experience.

Once this narrative is set, it’s hard to break. Even when positive stories are shared, the “N” is too low to offset the perception.

When you think about what examples may be forming your perception of remote work, how many of those are based out of your own experiences? What is the sample size? How does this compare to the good or bad hires onsite?

There is a false perception that all remote workers want to “go remote” to lead an easier life. The reality is that they often want to live a better life, which is distinctly different. For example, many individuals are looking for the opportunity to spend more time with their children, to optimize their schedule, or to devote unproductive time like a commute to something more productive. In fact, according to the IWG Global Workspace Survey, over 50% of people would prioritize flexible working over working for a prestigious company or more holiday allowance.

Founders often ask how they will find talented employees and furthermore, retain these talented employees. Here’s a hint: give them the freedom that they so clearly desire. The vast majority of distributed employees are not looking to work at the beach or even live anywhere near one?they are looking simply for autonomy over their lives.

What am I trying to communicate here?

  1. Don’t let survivorship bias influence your perception of remote workers. Build up your own impression through experience.
  2. It’s important to reframe the intentions of those looking to work remotely. Often, people do not want to work remotely to do less, but instead are looking to do more. If you vet for these signs of ambition, you will likely find yourself attracting talented employees.

Hiring Outside the Box

We’re taught from a young age to “think outside the box”, yet I think many have been trained throughout the decades to optimize within one. As hiring managers, when you’re looking for these truly disciplined thinkers, I question why so many companies automatically eliminate so many that have already proven through action their ability to think outside of the box.

You may hear the “horror stories” of a company hiring a remote candidate that went exceptionally badly, yet I’m sure the same hiring managers could cite an equally misguided in-office hire. Since remote work is the newer, more innovative model, we use a few examples to push back on the more innovative model.

Instead of using bad hires to discredit the entire model, I would encourage hiring managers to think about the type of individual they want to hire from the ground up:

  • Is it someone that takes initiative to design their own life?
  • Is it someone that works to find creative solutions to enable this life?
  • Is it someone who can work dynamically and flexibly?

If that’s the type of person you want in your company, don’t eliminate an entire cohort of them and open your mind to the future of work. In the “war for talent”, there is no better competitive advantage than getting access to thousands of candidates that your competitors are too fearful to explore.

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Posted by News Monkey