The Factors That Influence Remote Work Success

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Which kind of leads to today’s topic: remote work success

Recently, a study found that the distractions of working from home have people feeling less productive than they were in the office. While tempting to blame this on COVID lockdown, I don’t think it’s entirely fair (though I still believe coronavirus is a terrible thing for remote work). Instead, I consider this a failure of process, whether impacted by COVID or not. 

Looking to my own experiences plus the interviews I’ve done with successful remote entrepreneurs, it seems there are 7 factors that influence whether someone - or an organization - will be successful at remote work. This framework also explains a bit more about why COVID pushed some people to love remote work and others to hate it. 

Here are the factors: 

  1. A mindset opening

  2. The right introduction

  3. Connecting what you have to what you want

  4. A plan for success

  5. Knowing where you’re going

  6. Getting involved beyond work

  7. The strength of your community

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1 - A mindset opening

Because offices are the norm in the professional world, remote work needs an opening to become a viable option for you as an individual for or an organization as a whole. In other words: you need goals that remote work can make easier to achieve (or at the very least won’t hold you back).

This typically happens in one of four ways: 

  1. Career goals: My career goals were to detach my earning potential from my physical location, something I wrote about in Thrive Global. Short of being incredibly wealthy, the only way I saw to make money without needing to be in a specific location was remote work. 

  2. Financial goals: Floyd Marinescu shared with me that he started his business remotely not for some altruistic reason, but purely for money - not renting an office was cheaper than renting an office. Only then did he start to love the other benefits of remote work.

  3. Talent access: Melissa Kargiannakis wanted to build a world-leading AI company in her small hometown of Sault Sainte Marie, Canada. That required her to have some hybrid remote arrangements purely from a talent access perspective.

  4. Lifestyle and family: Joshua Teirnan worked in an office for years, commuting upwards of 2 hours per day. He saw remote work as an opportunity to spend more time with his young family. 

Without this mindset opening, individuals and organizations will have a much tougher time adapting to, and enjoying, remote arrangements. This might be the reason why some folks pushed into remote work due to COVID hate it - they were forced into it without any prior mindset opening.

2 - The right introduction

People need introductions to remote work that are easy to digest. Preferably, this exposure is in some form of revocable way or is 100 percent the individual’s choice. 

My first exposure to remote work was the occasional work-from-home day in my office job back in 2014. From there, I worked remotely while trying to build my first business throughout 2015 and 2016. 

A cool example I like of gradual exposure comes from Soapbox HQ. CEO and co-founder Brennan McEachran shared their journey into remote: 

  • The company had “Wired-In Wednesdays” where everyone was expected to do execution-focused work. No meetings were allowed, and you could work from wherever you wanted - home, office, cafe, etc. 

  • Surveys went out after a while, and employees reported feeling way more productive when they could work from anywhere. So the company expanded the program to Tuesdays and Thursdays - with a catch. Tuesdays and Thursdays were “Work From Anywhere Days” but you were still expected to be fully available for meetings, brainstorming, team work, etc.

  • Employees still reported feeling more productive overall, both individually and as a team. 

  • The company was about to add one more day - either Monday or Friday - when COVID hit, so they just went full remote. 

  • Now, the lease is up on their office and the company (with employees sharing their opinions via surveys) has chosen to go full-time remote even post-COVID. 

3 - Connecting what you have to what you want

A challenge with COVID-induced remote work is that it initially put people into a frenzy. Suddenly, it felt like every system was breaking down and all of them needed to be replaced. The reality, though, is that many systems and processes from office environments work in a remote setting as well - if you have the time to suss things out. 

This is also where a common misconception occurs: many folks believe that remote work is fundamentally opposite to in-office work, and that you must be totally alone for remote work to be real. This is not true. 

For example: as I built my remote business, I was still regularly attending networking events and popping by client offices when I wanted to. I didn’t need to do this, since I delivered value remotely, but I wanted to... So I did. It was the system I had in front of me to help me grow. I do this far less now, but it’s totally ok to leverage what you have in front of you. 

The trick is to understand that those systems can - and probably will - break down over time. It’s not feasible to go to downtown networking events when you work remotely outside of the city. Or it may not be a good idea to pop by a client office when you aren’t already nearby. But you can still start with the systems you have in place - no need to tear out everything. 

4 - A plan for success

It’s easy to plan for remote work failure - you just find a new office lease and start up again. What you really need to plan for is success, since success means maintenance and scale. 

That means: 

  • Pricing systems: Is your technology all-in-one pricing? Per-seat model? Something else? It’s less about the model and more that you know how you can scale it out as you grow. 

  • Infrastructure setup: If you’re using a piece of software, can it handle increased usage, requests, or other systematic pressure? As you grow remotely, you’ll be using infinitely more data / bandwidth - prepare for that. 

  • Systems setup: Do your processes, such as communications triage, scale easily, or will things get messy with everyone working full-time remote? 

  • Social setup: Do you have a real virtual water cooler or virtual social opportunities for the team?

  • Value delivery: With shifts to remote delivery or remote production, are you ready for scale and efficiency?  

When folks went remote from COVID, most companies upped their zoom subscription and hosted happy hours, both of which lost their lustre pretty quickly. The reality is that you have to plan for success if you want it to last. This doesn’t mean buying tons of expensive technology up front - look for pay as you grow tools like Slack, Workplace by FB, Zoom, Miro, and others. 

5 - Knowing where you’re going

This is tied to the first step - having a vision that remote work can enable. Simply “being remote” is not an end goal, but a means to an end. 

As an individual working remotely, you need to know what kind of lifestyle you’re aiming for, whether travel, family life, urban living, or country property (or something else entirely). 

As a company working remotely, leadership needs to understand where remote fits into the vision: employee freedom, talent access, cost savings, etc. 

How a company (or individual) approaches remote work changes depending on why they are leveraging remote work in the first place. An example here is Basecamp, which talks about being a “calm company” - their choice to go remote-first, according to their book It Doesn’t Have to be Crazy at Work, was based on making it easier for employees to do their jobs and not get caught up in the performative aspects of work. 

6 - Getting involved beyond work

Wherever you are in the world, real success will not come from working alone. Working or running a business remotely doesn’t change that.

From an entrepreneur perspective

As a founder or business leader, your ability to care for employees, sell, talk to customers, deal with admin, and all the other stuff that entrepreneurship throws your way depends on your emotional and mental capital. Giving back, being part of your community, and indulging your passions or interests outside of work is how you fill up your emotional and mental bank accounts. Let the business fix the financial side, but don’t forget about the other two - it’s critical for you as a leader. 

From a remote worker perspective

One of the biggest benefits of remote work is the freedom to engage with the world on your own terms. Travel, volunteer, indulge interests, have hobbies… it all adds up to a more well-rounded human experience. 

This was a step I took to heart with my remote business. Over the years of getting it off the ground and running it, I’ve: 

  • Co-founded Venture Out, one of Canada’s largest LGBTQ+ nonprofits.  

  • Started Remotely Inclined!

  • Travelled to France to help a family restore their chateau.

7 - The strength of your community

The office isn’t perfect. But it did provide a built-in social life with coworkers, chit chat, gossip, and more. Even if you didn’t engage in it much, it was nice to have. Going remote flips the script - instead of starting with a social life, you start with nothing. 

You have to build your own community as a remote worker, and especially as a remote entrepreneur. 

So if you want remote work to be a success, you - whether leader or employee - have to join communities: 

  • Social: Shared interest or identity groups, especially non-work interests or identities.

  • Professional development: People who have skills you want to learn.

  • Networking: People you can sell to, buy from, or partner with.

  • Doing your job better: People who can help you with the tricks of your trade.

Ideally, you’ll have a mix of online and in-person communities. Online communities will help you further hone skills in digital relationship building and value delivery, which is critical to your work. But in-person communities will help fight against feelings of isolation and provide the closeness that humans need. 

Did another factor contribute to your success in remote work? Join the conversation in the comments. 

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