Work-From-Anywhere: Building an Innovative, Healthy Culture

By Ryan Barton | November 16, 2021

Why call it “Work-From-Anywhere” (WFA)?

Because this is bigger than simply “working from home,” or “working remotely.”

If you let them, team members may choose to work in the office or out of it. Locally or on the road. Will you allow them to work from the home or the Himalayas? From Boston and Bahamas? From a box and with a fox?

(In defense of the last line, I have 3 small children, and “Green Eggs and Ham” is in regular rotation.)

5 principles for building an innovative, healthy culture with just the right amount of remote work.

Your organization’s “Work-From-Anywhere” policy will become one of the defining aspects of your culture, your recruitment, and your retention.  This one decision will spawn significant, long-term consequences. 

Crafting that policy is difficult.  Today, we spin in a blender of change, narrative, and counter-narrative.   

Headlines roar:  

“Remote Work Contributing to the Great Resignation”  
“68% of Large Companies Plan to Downsize Office Space”   
“Amazon Allows Indefinite Remote Work for Some”   
“Huge Study Suggests Remote Work Creates Silos, Changes Communications” 

Because the wrong decision will clearly erode success, I searched for an easy answer by talking to business leaders, reading books, discussing with my team, consuming articles, and digging into studies.  

An easy answer proved to be a Sasquatch.  Some believe.  Some of us raise an eyebrow.  

One thing is clear: employee expectation has changed fundamentally since March 2020.   

Every single employee who worked remotely over the pandemic has new preferences, beliefs, and expectations about their work.  But those preferences, beliefs, and expectations are all over the map. 

Those who hated working remotely will be dismayed if you close your office.  Those who thrived while working remotely will likely object to any mandatory days in the office.   

And yet, it’s also clear that if you don’t bring people back together, it can drag mental health, stifle communication, and hamper creativity.   

The hard right answer is to grind through the necessary questions, blend a policy, taste, and refine the recipe as needed.  

Hard to make a headline out of that.  But we aren’t here for headlines.  

We are here for a wise decision. 

5 principles for how to decide: 

Principle 1: Think well. Banish the easy button.   

WFA is not a simple problem.  It is not solved with a simple, easy policy.  Embrace it as a complex problem. 

Cut loose the anchor of the past. Until March 2020, your entire career was spent in a business climate that held certain assumptions about remote work.  Question each assumption and recognize our new paradigm. Do you think employees can’t be managed effectively if you can’t see them? That is a myth thoroughly busted.  Do you think everyone prefers coming to the office? Not uniformly, not anymore.  

And be suspicious of extreme changes. Before you close the office, think well.  Before you mandate everyone’s return, pause.  Remember: This is a complex issue. A simple solution will not solve it.   

Principle 2: Listen well.  Consider what is best for each person. 

No one is ever solely an “employee.” We are people: with dreams and anxieties, love and loneliness, families and pursuits. Thanks to video meetings, we have met others’ kids and dogs. Because of this window into their homes, we have learned new things about their lives and passions.  

Start with yourself. The only way to ask authentically. How is remote work for you? What do you want? What is healthiest for you? And does your emotional experience of work change when out of the office?   

Ask the people who work for you: what do they want?  In an ideal world, how much flexibility would they like?  What kind of schedule? When away, what do they miss about the office? When in the office, what do they miss about being away?  

Ask them about their wellbeing.  How is their anxiety and their joy, when working remotely?  What is the healthiest balance of WFA? Not the easiest balance, but the healthiest?  

Principle 3: Build well. Optimize for long-term, holistic success. 

Whatever the policy, it must further the most success for the most people over the longest time.  It must have the long-term in view. 

This means we must consider people and the business.  

A good business culture encourages creativity.  Creativity benefits from random interactions which are difficult to replicate remotely.  A famous example is Steve Jobs’ design of the Pixar office. He put the bathrooms in an atrium at the center of the workspace, forcing people to bump into each other and interact. Reportedly, it worked.  

A good business culture also includes mentoring.  Mentoring remotely must be done intentionally. In the office, it can happen far more organically. Consider this: Who do you talk to when you work remotely? And who do you talk to when you work in the office?  For most of us, those are two different answers.  

A business is also well served by attracting new applicants, and a flexible WFA policy tops the list of many looking for a new job.  Team members who move out of the area can be retained with WFA. 

A balance must be struck between flexible remote work options and necessary time together in person.   

Principle 4: Enable well. Evolve your technology. 

WFA groans and clanks if the technology doesn’t support it well.  All aspects of your technology plan should be in tune with supporting WFA.  Infrastructure moves to the cloud.  Desktops are replaced with laptops.  Communication tools are deployed (like Microsoft Teams).  Phone systems move to the cloud.  Business Intelligence software becomes more important (measuring outcomes in data).   

Of course, security measures must evolve rapidly.  Your workforce isn’t behind the firewall anymore!  A flexible WFA policy results in connection from unknown and possibly unsafe networks.  This puts the emphasis on securing the endpoint (the laptop, smartphone, and tablet), securing the infrastructure (email, applications, and files), and training staff diligently (and then real-world testing that training).  

At Mainstay, the IT service provider I lead, we use advanced planning and cybersecurity models to guide our clients through their technology evolution (and I risk the ire of Marketing if I don’t say that we’d be delighted to talk to you about your organization and its technology!) 

Principle 5: Accelerate well. Seize new opportunities. 

WFA opens new opportunities for the business.  Each business leader should carefully think through how WFA can be used to further success.   

Your clients and potential clients are more understanding of remotely delivered service.  This creates new markets for businesses typically bound by geography.   

Sales can be done more efficiently and to a broader audience.  Recruiting opportunities open.  Managers can use data in new ways to inform their understanding of team performance.   

Team members are more open to wellness initiatives and to benefitting from training for mental wellbeing.  Culture can evolve and become deeper and healthier.   

Intentionality can increase, as everyone wrestles with new routines, new schedules, and new events.  The office can be reimagined to support a changing work landscape.  

To facilitate this, all HR leaders must see WFA leadership as a competence to develop.  They serve a critical job of enabling a healthy culture and supporting each leader through the challenges of WFA.   

What Others are Deciding About Work From Anywhere: 

At Mainstay, we encourage team members to thoughtfully choose their own balance. The offices are a tool to improve their work and their experience.  It’s critical that each teammate monitors personal wellbeing.  Work isn’t just about being productive and too much alone time is detrimental.  Some teammates come into the office daily while others rarely. 

Mainstay holds events in-person and encourage in-person for deep conversations. There is no substitute for the presence of another human being. We ask teammates to try to come in one day per week, on the same day, so we create as much opportunity for random encounters as possible.  In person, we have different conversations, with different people, than we do when working remotely.   

WFA has allowed us to support teammates who move geographically.  In the past, when life called someone to another state (or to an on-the-road adventure), it meant the end of their time at Mainstay.  Not anymore. There are some legal hassles, but they are well worth solving.    

Currently, we are not currently hiring from out-of-area.  We believe training, mentoring, and integrating into the team is better done face-to-face.  We value deep relationships in our team, and building those from scratch, remotely, is harder.  We are working on this though and learning from the experience of other companies.  Someday, we may pursue it. 

The NH CPA firm Nathan Wechsler & Company decided the full team needs to be in the office, but only on Tuesdays + Thursdays, with personal choice MWF.  Exceptions are considered for days or roles that have no impact on clients, and they monitor for success.   

Basecamp, a popular software company, decided on no office at all.  The founders wrote a book on Work-From-Anywhere, called “Remote Work: Office not required.”  They are a wildly successful company with a far-flung team who have proven this can work.   

However, they also have proven full WFA has downsides.  In 2021, internal societal and political discussions went awry over their electronic channels.  All-hands meetings to handle the crisis had to be held on Teams.  And in a highly publicized way, it imploded, and 1/3 of Basecamp employees quit.  

The description of those online meetings (readily available online) is sobering.  It’s impossible not to wonder what could have been if they gathered in-person to hash things out. As a team who regularly worked together, face-to-face, and who had held all hard conversations in each other’s presence. 

WFA contains great promise and some peril.  Don’t limit your team with draconian measures.  And don’t hurt your culture with sweeping changes.   

Decide with care. It’s worth it.  


Ryan Barton is the founder and CEO of Mainstay Technologies, an NH-based technology services firm.  Mainstay believes technology and business can be powerful forces for good.  The company measures its success by its impact on people: Its clients, team, and community. It has received multiple awards, including Best Companies to Work For 4 years running, Business of the Year, 5 years on the Inc 5000 list, Business Excellence, and the Torch Award for Marketplace Ethics.  Ryan is a husband, father of three, and an insatiable reader. He loves to write and share about the relationship between our work and meaning. You can reach him on LinkedIn.