The Shark Side of Remote Work: An Open Letter to Kevin O'Leary

Published March 15, 2023

Dear Mr. O’Leary

As a long-time remote work advocate, consultant, and advisor, I’m happy that you see the reality of the situation unfolding around you. Employees clearly prefer choice over status-quo, and remote work appears to be a permanent fixture. Several of the quotes you shared in a recent Fortune article suggest that you have a good pulse on how working flexibly is impacting your corporate endeavors and the labor marketplace as a whole. You stated:

  • Productivity remains unchanged
  • People aren’t interested in going back to an office.
  • Project management styles have to change
  • People entering the workforce now may have zero in-office experience

Broader research is telling as well…

  • 98% of remote workers want to keep working remotely, at least some of the time, for the rest of their careers.1

I’d love to stop here and let this be another nail in the coffin of return-to-office demands, but remote work the way you described it is a major risk to the sustainability of your workforce as well as every employer that follows your lead. Here’s the excerpt from the article that raises the alarm: 

"The tradeoff for workers, he noted, is there’s “probably less private time on weekends.” He said he feels free to call his employees at any time on any day of the week. ‘That’s the deal. If you don’t work in the office, I can call you at two in the morning if we’ve got a crisis. And they’re gonna answer. That’s the way they’re used to it now."

My big concerns are as follows:

The remote work penalty.

Treating a completely viable working model as a concession that allows you to make unreasonable demands on employees is out of date and should be out of the question!  

Your statement suggests that in-office employees aren’t held to the same standard as those working flexibly. Rewarding presenteeism while creating an environment where remote workers sleep with their phones on their nightstands with notifications on and ringer volume up is a near-sighted operational model. The old-guard power struggle that hides behind the acceptance of remote work only serves to intensify the struggles that remote workers report.

  • Burnout - 69% of remote workers report that they are experiencing burnout, contributing to a $322 Billion loss to companies around the world in turnover and productivity costs.2
  • Overworking - 53% of remote employees report working more hours than when they were in the office, with nearly ⅓ working ‘much more’ than before.3
  • Unable to unplug - 61% of remote workers find it difficult to unplug outside of working hours, with 1 in 5 describing this as their biggest struggle.4 

Personally, as an employee who has been roused from sleep at 2 AM by a boss in “crisis”, that was on-call 24 hours a day, your approach is doing more harm than good. 

Your influence in a toxic direction.

Your reach as a TV personality and investor is exceptional. People will follow your lead, and the path you’re suggesting leads to reduced retention, engagement, and employee satisfaction. It’s a bad approach to remote work and it's bad for business.

It’s also illegal in a growing number of places around the world. Ontario, home to Canada's largest city and a booming tech scene, has recently enacted a “Right to Disconnect Law” to protect employees from bosses like you. They’re not the only ones. Spain, Portugal, and France have also passed similar legislation.5

I’ve consulted organizations where employees felt the need to pull off the highway during their commute to respond to direct messages and emails in order to keep their bosses happy. They were always ‘on’ and were afraid of their leaders.

Rather than doubling down on a power play that gives you the right to access employees at any time of the day or night, consider the following suggestions:

  • Set reasonable expectations for response times and out-of-office hours. These should be documented, distributed, and discussed openly, and you should give your team the power to hold you accountable. 
  • Encourage remote work employees to toggle off notifications on their mobile devices. No one needs to know that they got an email from you at 10:00 PM.
  • Develop an emergency action plan that addresses what a “crisis” is, and what to do about it. Don’t use business-as-usual events as an excuse to disrupt the private lives of your employees.

I urge you to embrace more than just the inevitability of a flexible workplace. Embrace and lead the way for a human-centric working experience.   

I welcome your response, but please, don't send it at 2 AM.


  3. Ibid
  4. Ibid