Some things should just be simple.

Like, having flexible workplace options.

The thing is, it is simple – at least to understand. Or justify. But easy?? That’s a different conversation.

It feels like cognitive dissonance to suggest that an uncomplicated workplace philosophy – which can inspire both productivity and employee well-being – could be in fact complex. What’s more, getting there en masse faces a number of headwinds.

We’ve done an incredible job adapting to the pandemic to make WFH tolerable at worst.  Hybrid (with flexibility – not the apple version!), however, represents a conscious effort – an explicit strategy and set of practices that has to be planned for and implemented, with no inciting force outside of our own determination.  So, to make it work we have to think about not only what we have to do but what can hold us back. The list of hurdles we need to overcome is anything but brief.

A Reluctance to Care.

I have been known to say that in business, caring is a strategy. Make no mistake – there are piles of compassionate leaders who naturally lead their teams with empathy; but the kind of caring I’m talking about survives transition and is deeply embedded in culture and policy. And not every company has that to a robust degree. Don’t believe me? Here’s a test – choose an exec at your organization and ask them for details of the employee retention strategy or best practices. See what you get back.

Far too many responses will be met with some spitting and sputtering (read: never thought about it), loads of philosophical rhetoric or an itemization of quick-and-dirty policy that can be uploaded with the stroke of a pen (bonus, vacation). What you might not hear enough of is a sensitivity to matters that more directly drive employee happiness (empowerment, elite coaching and performance measurement, efficient processes that give time back or proactively minimize job stress, etc).

Employers have historically held the leverage in employee relationships – or have seen themselves as having it. That translates into a lucky-to-have-a-job underlying management approach, which has in turn impeded much policy or initiatives designed specifically to promote employee well-being (not just maintain it when you are breaking down). Yes, companies need to be taught to care as a matter of course, and invest in long term well-being, and the productivity gains that can come with it. Caring hasn’t pervasively come naturally in the past; that makes it a challenge to easily incubate in the future.

I will note there are many exceptions to this phenomenon. Companies that are innovative by design, tech-based or otherwise with low task interdependence, young in their lifecycle or on a persistent growth trajectory are notorious for delivering value for their employees – at least as long as these foundational conditions exist. Some think that younger cohorts are just more empathetic; my experience has taught me that business conditions have greatest impact on opportunity.

...and do Employees even Care themselves?

If your entire perspective is derived from social media engagement – where everything is amplified – yeah, this might seem like a big deal to most employees. But if salary and benefits continue as the main drivers of employment upgrades, we’ll see employers continue to take the easy way out in attracting and retaining good staff – all through the stroke of a pen. No need to take on the hard stuff such as improving culture and working conditions.

All the Work.

Hybrid working is not simply the result of a policy document lathered up by HR. To be executed properly it will require integrated consideration of office space, performance management, recruiting, process, decision support systems, technical infrastructure and culture. I could write a separate piece on each of these, but suffice to say for now that one heckuva team needs to come together with enough available capacity to re-engineer the organization’s infrastructure in a co-ordinated way. Might all start with creating roles specifically for organizational effectiveness, because this is no side project for existing employees already working 10 hours/day in survival mode. If resources are not summoned/hired for this massive transitional project, if the C-Suite is not driving this, it simply doesn’t happen.

And it’s difficult work. We’re seeing brilliant companies come together to study the future of work in detail for months, and emerge with more questions than answers. How do we make systems and processes come together in a way that we can measure to assure us that we are moving forward? Still so much to learn and understand. Daunting.

Our view of this challenging and uncertain path forward is causing a bit of war-gaming among organizations that are likely standing by for the lowest-common denominator option to present itself. A year and a half in, many employers are still only thinking about plans (see results of one survey in this article) despite our imminent emergence from the pandemic. It is possible that leaders are taking an economizing, wait-and-see approach, to artlessly replicate any policies that become widespread, just to keep pace. A commonplace strategic approach to HR policy such as this, grievously void in vision, could prevent widespread flexible policy from gaining traction.

A Bias toward Immediacy and Certainty.

All the work comes with a cost – in both headcount and outright dollars – to implement properly. And there are barriers to securing these resources, in the form of a bias against spending.

The strength of this bias depends mostly on 3 factors:

  1. Your current business trajectory
  2. Who your investors are
  3. Who controls the purse strings

If you are a publicly-traded company, your line of sight is one or two quarterly cycles ahead. If you have private investors, there may be more flexibility. If you are self-funded, you’re golden.

In the worst of scenarios you have a CFO as a gatekeeper whose mind is squarely focused on the business metrics to be reported to the board and Wall/Bay Street analysts in the coming quarter. So when you approach them for investment for ‘the right thing to do’ that will pay dividends over the longer term (e.g. new product ideas, diversity programs and supports, infrastructure upgrades that promote productivity and well-being), expect some form of this conversation:

Them: So you want X dollars/people to invest in Y initiative. What will be the return to the top or bottom line and when?

You: …………….

I have lost count in my career of the number of great ideas that have died with this very conversation where I was an observer or participant. It’s how especially larger companies work. They want certainty and immediacy in results – something you just won’t be able to provide. So the pitch will lose momentum in this moment, because your request will cause a direct hit on the metrics upon which the C-Suite is evaluated. And you cannot provide them with clear justification that the investment will be recovered.

Fear and Mistrust.

Let’s face it: leaders are only so empowering and moreover, tend to fear what they don’t know or can’t see. And what they don’t know is what you’re doing every minute of the day – and they don’t have the ability to check in on you when it’s a good time for them. The desire for control underlines a resulting troubling dynamic, creating a double whammy: uncertainty over what you’re up to, mixed with frustration that we can’t influence your actions at a moment’s notice.


You may be one of the lucky people who works on a team whose members never change and does precisely the same thing every day. If that’s you, congratulations. You can establish structure and process once, then go on auto-pilot for the duration.

The rest of us stand to be caught up in an endless cycle of administration. We call this process loss in Organizational Behavior; it’s all the extra work to manage a team of ever-changing working situations, from structure to schedule to location. Don’t underestimate the added administrative burden placed on teams to (re)organize themselves on the daily. I teach several university-level distance ed. marketing courses; they are 9 weeks of working in teams with weekly deliverables, which the teams need to co-ordinate. The #1 complaint we get about the course is the incessant amount of coordination required to complete activities across time zones when they are rarely together on campus.

And as we teach in Org Behavior, the antidote to chaos is standardization. You can see where I’m headed with this.

Accepting that Flexibility comes with Compromise.

I think I’m not giving people enough credit here, but I’ll point this out anyway. Much like how there are many who think a 4-day work week simply means everyone works 20% less for potentially the same pay (although there will be cases where this seems to work), there are those who are assuming that flexible work means ongoing permission to come and go as they please.

Not likely so (and the more powerful insight here is that we haven’t yet begun to identify the parameters of flexible work as a foundation for implementation). Even if your organization does not mandate which days you are to be in the office, there are other forces that can urge you back in. You may have business partners who you need to please and have preferences. Your team(s) may agree to meet in a live setting for certain activities, and vote against your preferences on when to do so. Perhaps apple was getting ahead of this through its policy, attracting anger to the C-Suite and away from your own team mates who refuse to give in to your requests.


And there are many that can be caused or exacerbated. Not all can be easily measured from our current viewpoint:

  • Flexible work favors higher-paid knowledge workers and penalizes hourly wage workers who perform services in person. We’re driving a further divide in well-being between classes
  • Minorities and women make up a disproportionate level of low-wage service work
  • Those collaborating more in person are expected to form deeper relationships. This dynamic can breed a sort of favoritism (proximity bias), which can lead to disproportionate rewards for those regularly in attendance


And there are those who believe we will start out with the best of intentions, but then we will gradually revert to pre-pandemic conditions. A stalling post-pandemic economy paired with the dissolution of public supports could force workers back to whatever job is available.

And then, within your own organization, keep an eye on how leaders behave, because it causes a certain contagion that ripples across an organization. If execs start showing up every day, if your boss starts showing up every day, you or those around you may instinctively begin to change behavior in recognition of emerging, unspoken norms.

The other type of inertia comes from a plateau or decline in business results. The last 3 corporate jobs I held went through this transition. I cannot capably express to you how quickly culture changes when business results shift – how all the cool ideas get killed, perks are withdrawn, spending is pulled back. An all hands on deck mentality is instantly installed because the business is under duress; employees, as a result, start to introduce all sorts of endearing (and cut-throat!) behaviors to avoid the next round of headcount reduction.

Disconnection and Transition.

If a flex policy inspires a largely remote culture, then additional phenomena emerge. Bonds between employees progressively dissolve and with it goes what we in OB call the affective commitment that keeps employees loyal. If turnover becomes rampant, I can foresee situations where employers gravitate back to an office culture to compel employees to show their interest in sustaining employment with the company.

The Re-emergence of the Office.

You think commercial real estate is going down without a fight? Think again. The industry could reinvent itself, and with it, re-imagine the workplace in a way that repositions the vibe of your den or the table at the local coffee shop from oasis to third-world working conditions.

PS I’m expecting a similar reinvention with brick-and-mortar retail, eventually, too. But, I digress…


I could classify this within the realm of inertia, but it deserves its own headline. We’re early in the game here and more data mixed with rhetoric stands to emerge on results of hybrid policy, as we progress more deeply into the new normal. We know employees will continue to want flexible arrangements – they have wanted this long before the pandemic. But it’s the (perceived) successes and failures that command the headlines and control the narrative early on that may inform the ultimate direction we take. We like our sound bytes; if we start to hear chirps of ‘this doesn’t work’, look out.

There are tailwinds, though.

Hope for a sustained new flexible normal intensifies with time, and the persistence of the current and any forthcoming virus. As the widespread return to traditional office formal is put on pause, we see new habits calcifying. Organizations move from adapting to the current state to optimizing it. And then, particularly where it comes to Commercial Real Estate and other infrastructural matters, companies will be confronted with decisions that force them to commit to longer term, pandemic-style structures because they can no longer financially and operationally tread water.

And then on the labor front, we are seeing here in Canada an invasion of remote-first foreign companies tapping into our vast talent at more affordable rates than the home country. As organizations commit to spreading out talent globally, the opportunity to return to pre-pandemic structures becomes ever more limited.

In light of these obstacles, where do I, myself, stand? In truth, I’m not optimistic that flex working will sustain itself as some sort of normal beyond the medium term. I do believe, though, that our experiences with the pandemic will accelerate workplace innovation in this area – just not to the degree we might have hoped. It’s easy to get caught up in what feels like a movement that exists largely in social media; I have so many influencers in my feed who have convinced themselves these new habits are calcified – and it’s true, as days go by this is more and more the case. But I look at it as if we have assured ourselves that river water that has stopped moving with a dam in place will continue to rest in place once the dam is removed.

I see social media as a series of ideological bubbles that function like echo chambers. Almost everything in our feed is designed to support our wishes and thinking, but does not necessarily reflect the broader market conditions. So as the dam is removed, I caution all that there are a number of forces at play, working against us. If we truly want to manifest a new vision for how we work, we must avoid the temptation overlook some ominous hurdles, as we become much more deliberate and resolute in how we come together to influence a better future.