Matt Spoke: Entrepreneurs are uniquely suited to working from home - The Hub

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I’m sitting in my home office as I write this. In the other room, I can hear my two children and my wife. I’ll take a break from my computer in an hour or so to go do some parenting and offer my wife a break in her day and stay “on duty” until bedtime, at which point I’ll get back online to finish my day. We became parents early in the pandemic, and we both have entrepreneurial careers. We’re not like most families.
All that to say, we’ve been incredibly fortunate over the past two-and-a-half years to have the types of careers that provided us the flexibility to have children and be incredibly present in their early years, all while pushing ourselves with risky and ambitious professional lives.
Of course, the flexibility we’ve enjoyed has become true for lots of families, whether or not entrepreneurs. The pandemic altered our reality in fundamental ways; maybe most significantly in our work. But now, as we get more comfortable leaving the darkest days of COVID behind us, society (and our economy) will have to reckon with what the relationship between people and work should be.
I won’t pretend to know how labour should adjust to the post-pandemic world, but I’ll try to provide some perspective based on my experience as an entrepreneur and as a CEO of a small company, and I’ll try to specifically answer the question of whether employees should be required to return to offices or stay remote indefinitely.
And before I lay out my thoughts, I’ll caveat this by saying that in-person human interaction in all contexts is incredibly important and competitively valuable to any company. For my company specifically, we find that encouraging teams to occasionally gather for social events and regularly bringing the whole company together for “off-site” retreats creates the social cohesion that we need to be productive and to have fun working together.
For context, I lead a team of 35 people, spread across the country but intimately connected to one another through our work. We primarily work remotely (we have a small office in Toronto that can be used optionally). I think this setup is working incredibly well for us, although I realize that I’m uniquely fortunate to have a team that I have complete confidence in and who I trust.
I can imagine other workplaces where this is not the case; where workplace relationships are loosely held, where some roles are menial in nature and easily glazed over in the grand scheme of a large company, and where people are primarily there for a paycheque and benefits.
So naturally, there is no prescription for what a “new normal” might look like across the board. But I do take from my own personal entrepreneurial experience that there are types of people and types of jobs that are well suited to thrive in completely autonomous work environments, and there are types that are not.
I generally like to think of entrepreneurship as a spectrum. On the one end is a person taking an enormous risk in the pursuit of an entrepreneurial idea. On the other end is a person who clocks in and out for a shift in a large company and who optimizes their career for stability and benefits.
Along the middle of that spectrum are many different kinds of people and jobs. In the context of my company, I like to think that we only hire entrepreneurs—or people very close to that first end of the spectrum. Every one of our employees is taking a risk working on an early-stage company that could fail. They’re all taking personal and professional risks by choosing not to work at a big bank or a big tech company.
This is frankly the number one thing we filter for in interviews. “Will you thrive in an environment of risk?” “Do you understand that your work directly impacts the probability of our success?”
So when considering how workplaces should adjust their work policies between remote work and offices, I think it’s important to roughly place people on that spectrum. An “entrepreneur” (or someone close to it) is likely to be hugely productive in any environment. Ultimately, their livelihood depends on it. Their contributions every day can be directly linked to the likelihood of the company succeeding or failing.
The moment that’s no longer true, I’d argue it’s worth considering a transition back to “normal” office work.
There is likely some strong correlation between the size of the company and the more I’d think that this is true.
Rogers or TD Bank would probably be well served to transition back to in-person work if they don’t want to harm their bottom line and competitiveness over the medium term. Although their employees will be the first to kick and scream, they ultimately take close to no risk along that entrepreneurial spectrum in their careers, and the quality of their work will slowly suffer the longer they spend away from a structured work environment.
On the other hand, for the class of talent that contributes to our most innovative and entrepreneurial companies, they should be given lots of latitude. This type of person already naturally thrives in an environment with less structure and more accountability. Remote work is simply that.
The less obvious cases will be companies with lots of talent somewhere in the middle of that spectrum. Shopify and Apple come to mind. But I think there are mitigating factors that can allow for experimentation in different companies.
In Shopify’s case, after their recent and significant layoffs,¹ the message was quite clear: employees are being trusted to contribute from home or be cut.
Apple, on the other hand, is relying on the power of its brand as an employer to insist that employees adhere to its new mandatory office policies or look for a job elsewhere.²
Ultimately, I think the market will eventually solve this problem. With employers finding that their work policies directly impact how competitive they are, they’ll have no choice but to adjust and the talent market will slowly shift back to normal work expectations.
Companies that are not well positioned to succeed with a fully autonomous “entrepreneurial” workforce, but who continue insisting on remote policies at the request of employees, will face the harsh reality of competition from someone being more pragmatic about the issue.
But for now, I’m going to get back to work.
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