Employee surveillance will increase. An unfortunate consequence of the rise of remote working is the expansion of employee monitoring from employers concerned about productivity and security. With the disappearing division between work and home life, I expect to see conflicts in the near future between employee privacy and a company’s right to measure performance.


When it comes to designing the future of work, one size fits none. Discovering success isn’t about a hybrid model or offering remote work options. Individuals and organizations are looking for more freedom. The freedom to choose the work model that makes the most sense. The freedom to choose their own values. And the freedom to pursue what matters most. We reached out to successful leaders and thought leaders across all industries to glean their insights and predictions about how to create a future that works.

As a part of our interview series called “How Employers and Employees are Reworking Work Together,” we had the pleasure to interview Jason Morwick.

Jason Morwick is the Head of Remote-first at Cactus Communications, a global technology company that accelerates scientific advancement. He is the co-author of 3 books on remote work, including Making Telework Work (2009), Workshift: Future-proof Your Organization for the 21st Century (2013), and Remote Leadership: Successfully Leading Work-from-anywhere and Hybrid Teams (2021). Jason has been a remote work advocate for over a decade.


Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today.

The most defining experience in my life was attending the United States Military Academy at West Point and the following years I spent as an infantry officer in the Army. West Point taught me discipline, organization skills, how to think analytically, handle stress, and most importantly, how to lead others. Those skills were put to the test after I graduated and went to Ranger school, a grueling 61-day course that trains soldiers to exhaustion while leading small teams. Ranger training was like a finishing school in a way. It taught me how to adapt to changing situations and think on my feet. I consider all these life skills that I have applied to corporate life.

Let’s zoom out. What do you predict will be the same about work, the workforce and the workplace 10–15 years from now? What do you predict will be different?

We are living through a period of great disruption and that is accelerating changes in the workplace that have been proposed and theorized over the past couple of decades. It’s exciting to witness these transformations firsthand and watch what is working and what isn’t. Employees are reevaluating their relationship with work and pushing employers to rethink how, where, and when they need people to work. Working from home and remote working will evolve into true work-from-anywhere models. The Monday through Friday, 9-to-5 schedule that has been around for over a century will finally become a thing of the past. Career paths won’t necessarily follow a traditional, linear trajectory as people may decide to opt out from corporate life for extended periods to pursue a passion, focus on their family, or just enjoy life more. New technologies, such as virtual reality (VR) and augmented reality (AR), will become more common in the workplace and will improve our virtual interactions. To better handle labor shortages, employers will have to increase automation and leverage artificial intelligence to fill the gaps.

What won’t change is the human element that companies rely on. Despite being thousands of miles apart, people want to feel connected to their coworkers and to the organization. Employees want leaders that are empathetic, engaging, and willing to listen. Beyond new workplace designs and structures, everyone still wants to feel valued and do meaningful work.

What advice would you offer to employers who want to future-proof their organizations?

First, listen to your employees and be open to new ideas. Right now, there is a shortage of talent in most sectors and employees are reexamining what they want from an employer. Leaders that ignore employee needs or desires run the risk of losing talent to competitors. Pay attention to what is happening in your industry and what competitors are doing to prevent attrition. Be willing to listen to what your employees want and take some risks to experiment with new ideas. Next, make someone responsible for the transformation. Not only does this demonstrate the organization’s commitment to change, it also increases the chances of success. If you are striving for organizational change but it’s perceived as just another HR initiative with little sponsorship or no one accountable, then it will likely fail. Many companies that want to transition to a remote working environment have recently created positions, such as a Head of Remote. This ensures that there is someone, or a team, that will provide the focus and energy needed meet organizational goals.

What do you predict will be the biggest gaps between what employers are willing to offer and what employees expect as we move forward? And what strategies would you offer about how to reconcile those gaps?

Employee aspirations will always outpace an employer’s ability to fulfill those requests. For example, we have employees inquiring about living as a digital nomad, living temporarily in one country for a period and then moving to another. Before we can say yes, we are obligated to do the due diligence on various country employment laws, make decisions around compensation, and understand any risks or impacts to the business. A lot of thought and effort can go on behind the scenes for something that may seem simple from the employee’s perspective. We are frequently taking the pulse of the organization and collecting feedback from employees. We receive so many ideas that it is impossible to do everything at once, so we have to prioritize, schedule, and execute on the most impactful initiatives. Communicating back to employees, providing visibility on where we are, and being transparent about what we can or can’t do helps to keep everyone engaged and aligned.

We simultaneously joined a global experiment together last year called “Working From Home.” How will this experience influence the future of work?

Remote advocates like me have been saying for almost 2 decades that the remote work revolution was just around the corner. But it never really happened until the pandemic hit. Why? Years ago, as a remote work consultant, I saw the reluctance most leaders had to letting employees work from home and the biases many had against teleworkers. Remote work advocates were constantly pushing through headwinds to make progress. However, the experience of the past 2 years forced people to change their work behaviors whether they wanted to or not. That shared experience is tearing down the mental barriers that prevented remote working in the past. We are seeing a tidal change in how people think of work and the flexibility that is possible. At a minimum, we’ll see working from home continue in the future, but it’s likely we’ll also see even more flexible work structures, from condensed work weeks to allowing more flexibility throughout the day.

We’ve all read the headlines about how the pandemic reshaped the workforce. What societal changes do you foresee as necessary to support a future of work that works for everyone?

First, we need to bridge the digital divide in this country. Studies from the past 2 years show that over one-fifth of Americans still do not have access to the internet. That’s unimaginable to someone like me that spends most of my working hours online. We need better access to broadband, specifically in rural areas and areas of low income. If we don’t improve the infrastructure and encourage more competition in the market, then we are missing a tremendous opportunity to engage a large number of potential workers.

Tax laws also need to improve. Current state income tax laws are not written with remote workers in mind. States like New York, apply a “convenience of employer” rule which allows them to tax nonresidents on their entire income while they work remotely in another state for a New York-based business. This can lead to double taxation in some scenarios, paying income tax to 2 different states. New York is not alone. Several other states have similar laws. Obviously, this can dampen the expectation of working from anywhere. Employers may also have issues if they have a single physical location but remote workers in several states. And it only gets more complicated when you start going beyond income tax issues. Federal laws on remote work are needed to cut through all of this and can simplify taxation for employees and employers.

What is your greatest source of optimism about the future of work?

A decade ago, when I was consulting and advocating for remote work, there was always an apprehension for employees to request remote work options or increase the amount they were already teleworking. They were afraid that it would be held against them. Their careers might suffer because they were not getting face time with their boss or peers. Leaders were skeptical of workers being out of sight. Now that everyone has been forced into a 2-year experiment with remote work, leaders and employees alike have found that remote work can offer more time and flexibility to improve their lives. Productivity doesn’t have to suffer. Work still gets done. Few people that I speak with now want to go back to the way things were pre-pandemic. Mindsets have finally changed.

Our collective mental health and wellbeing are now considered collateral as we consider the future of work. What innovative strategies do you see employers offering to help improve and optimize their employee’s mental health and wellbeing?

There’s a lot going on in this area. Many employers are taking an active interest in the well-being of their workers. Some of this may have occurred prior to the pandemic, but not to the level that it has been raised to now. Of course, managers are conducting lots of internal surveys and focus groups to better understand some of the biggest pain points, such as feeling burnt out, overwhelmed due to balancing childcare with work, feeling isolated, or staying motivated. At CACTUS, we have taken many steps to improve employee well-being. We’ve engaged with partners to offer online classes from meditation to physical health, provided access to a well-being app, created online communities based on employee interests to keep people connected, and 24/7 chat capability with a mental health counselor. We are also rolling out training for managers so they are better equipped to recognize potential mental health issues.

It seems like there’s a new headline every day. ‘The Great Resignation’. ‘The Great Reconfiguration’. And now the ‘Great Reevaluation’. What are the most important messages leaders need to hear from these headlines? How do company cultures need to evolve?

The most important message for leaders is that the old paradigms may no longer be valid. Whatever you were doing to retain talent in your organization pre-pandemic may no longer apply. The data gathered over the past 2 years may seem contradictory — employees want flexibility on when they have to be in the office, but they also want to work for companies where they feel connected. Ensuring that the organizational culture doesn’t become diluted as it becomes more dispersed is going to be a challenge for most leaders.

Let’s get more specific. What are your “Top 5 Trends To Track In the Future of Work?” (Please share a story or example for each.)

  1. Flexibility is our future. Survey after survey reveals similar results: employees want more flexibility in where they work. Although the pandemic challenged us to rethink where work gets done, the next phase will push companies to reconsider when work gets done. Software company Bolt recently announced that it was permanently moving to a 4-day workweek. Employee preferences will push more companies to experiment with alternative work schedules in order to attract or retain talent.
  2. Solutions for working mothers. While remote working challenged many workers, it was particularly difficult for working mothers. Women still bear a disproportionate amount of childcare and domestic responsibilities which contributed to almost 2 million women leaving the workforce during the pandemic. Companies will have to get creative to help working mothers, whether it is more flexibility in work scheduling, more accommodations for new mothers, or creating internal support groups.
  3. Artificial intelligence for internal operations. At CACTUS, we use Amber, an employee engagement chatbot, that periodically checks in with employees and collects feedback. It is intended to augment human interaction and collect broader samples than if the HR team had to do it themselves. This type of technology will become more sophisticated and personalized in the future. For example, the AI may be able to recognize when an employee becomes disengaged by measuring their activity across the network and intervene to offer solutions before the employee decides to leave the organization.
  4. The gig economy will reach all job sectors. For years, the gig economy has continued to gain momentum. Upwork and Fiverr became popular for providing access to global talent pools of freelancers that could do a variety of jobs. Now, you can find freelancers with even more complex skills. For example, at Kolabtree you can find a freelance scientist to help with business or research needs. Soon, employers will have access to any type of freelance or contract.
  5. Employee surveillance will increase. An unfortunate consequence of the rise of remote working is the expansion of employee monitoring from employers concerned about productivity and security. With the disappearing division between work and home life, I expect to see conflicts in the near future between employee privacy and a company’s right to measure performance.

I keep quotes on my desk and on scraps of paper to stay inspired. What’s your favorite “Life Lesson Quote”? And how has this quote shaped your perspective?

“Don’t be a linear thinking in a time of exponential change.” I’m paraphrasing a quote from a recent interview with Nobel prize winner Daniel Kahneman. He said, “People are linear. When linear people are faced with exponential change, they’re not going to be able to adapt to that very easily.” He was specifically referring to artificial intelligence but his thoughts could apply to any disruption change, such as what we are seeing in the workplace due to the pandemic and how people are re-evaluating their relationship with their job.

(For reference to the article I am referring to: Daniel Kahneman: ‘Clearly AI is going to win. How people are going to adjust is a fascinating problem’ | Science and nature books | The Guardian)

Our readers often like to continue the conversation with our featured interviewees. How can they best connect with you and stay current on what you’re discovering?

They can connect with me on LinkedIn: https://www.linkedin.com/in/jason-morwick.

Or, they can email me at [email protected].

Follow Cactus Communications at https://twitter.com/Cactusglobal (@CactusGlobal).

Thank you for sharing your insights and predictions. We appreciate the gift of your time and wish you continued success and good health.