Oh how it’s true that the more things change, the more they stay the same.

And based on my years of experience (yeah, I’m old) in many roles, functions, industries and territories, I might offer that within the workplace, the theory holds. Sure, we roll into work on the daily and engage in furious activity aimed at changing our collective economic trajectory. But if we take a giant step back, we might observe that over time in our own organization and across others, we simply haven’t advanced at the same pace of society at large in one or more of these more crucial areas of management practice to transform performance and enhance well-being:

1. Innovation. And I mean real, entrepreneurial-minded, value-added, disruptive innovation. Thankfully, startups have become a thing over the last dozen years or so to take up much of this slack. But at some point in our business life stage we all-too-regularly lose our entrepreneurial spirit. You know this is happening when execs start calling emergency brainstorming meetings to plead their employees to produce some sort of thinking that is both transformational, yet importantly, easy to implement. 

2. Time and productivity. What is your biggest time suck? The answer usually toggles between meetings and emails/messages. I’ll use meetings as the great offender to make my point. Why have countless articles and blog posts been written on how to run more effective meetings yet we still waste soooo much time in those we find of so little value? (I have written on this before and will present similar arguments in the context of the broader observations of this piece). Or as Juliet Schor of Boston College examines in this video, why are we not working less having invented so much labor-saving technology?

3. Equity, Diversity and Inclusion (EDI). It has never been a secret that exemplary EDI practices breed more innovation and better business outcomes, so why are we simply not seeing enough examples of robust policies and strategies being implemented? This is incrementally frustrating particularly to BIPOC professionals and stakeholders who have been audience to widespread stated commitment to more inclusive workplaces in the wake of the social tragedies leading up to and including prominent events in 2020.

4. Remote work options. At the time of writing, we haven’t yet seen how this practice will play out; we’ll have to wait until the pandemic subsides. But I have gone on record that this great idea that is valued by employees faces some real headwinds once we get our regular lives back. And, given the perspective I am about to present, I feel it prudent to flag this one to recognize some pitfalls ahead that we should anticipate and act on before we lose this worthwhile initiative.

Comparing our lives at the turn of the century, it’s safe to say that we have materially different tools and processes to help us get organized, plan, query information, stay informed, date, socialize, look after our health, travel, create content and entertain ourselves.

The contrasts in our work life are less noticeable by comparison. Professional conduct has improved over time for sure, but the biggest difference I think has been the introduction of smart phones and complementary communication tools. The impact: work is now present in our lives 24/7. Yay. I remember the days when I could cross the threshold of the office door and completely forget about work until I crossed that threshold once again to start my next work day. Glorious. Some days I really miss it.

So why do we get stuck? Let me first say that I’m not here to make excuses for anyone, but rather to simply audit the reasons for the lack of widespread progress in the most necessary and transformational areas. My plan is to conclude with some thoughts on how to go about causing some of that progress; but to do this effectively, we have to first acknowledge the forces that act alone or conspire together to get in our way:

We chase what we can measure.

I have heard this issue brought up in different contexts using different language. In marketing, we tend to favor digital promotional activity (versus, say, a sponsorship or other offline engagement) simply because we can measure it. If we can report back a concrete result we are more likely to invest.

I don’t have many mentors that I idolize among those I have never met. But I will say that former Harvard Professor and innovation guru Clay Christensen (RIP L ) would be one exception. He makes this point by examining our lives, to reconcile our late-life regret for not caring for our health and relationships with the decisions on what to pursue in our earlier years – more quantifiable things (that we can also promote).  This is almost a human-nature default mindset we can’t seem to shake.

To properly invest the time and energy in productivity and EDI for example, we’ll get easily distracted by trying to quantify the benefit. If we can’t do that on the front end we almost immediately start to lose incentive assign resources. To make matters worse, only the more entrepreneurial leaders have appetite for risk, so even if we come up with some kind of number we demand certainty to go with it. If we fail on both of those – well, that’s two strikes already.

I realize there is always a case to attaching goals and metrics to any initiative and that certainly applies here. The challenge is, we can only measure so many elements with metrics that feel important. The consequence tends to be more focus on the less meaningful but more measurable metrics we can formulate. In the EDI world that likely means a primary dashboard on representation with little consideration to the question of knowing if the company has actually become one that diverse employees would like to be a part of.

How we are measured affects what we chase.

This concept is a variant of the first, but needs to be recognized independently. Except for self-funded startups, government institutions and some non-profit organizations, we all ultimately report to some higher entity that is usually some combination of a board and investors.

And what is their expectation? Results. Historically, the fate of CEOs are typically determined by results over an approximately 18 month stretch. Within that time period are monthly and quarterly cycles that need to show progress, especially if Wall/Bay Streets factor in. What’s more, because the proportion of shareholders (VCs, equities, etc.) are increasingly institutional more than individual or private, the pressure to produce substantial returns over ever-shortening time frames has been gradually mounting.

I have often said – and others have concurred – that the quarterly financial cycle is the enemy of invention. Christensen has gone on record in his keynotes and most famous book The Innovator’s Dilemma asserting that common shareholder metrics such as RONA have effectively killed the business case for disruptive innovation. Because as we all know, new business ideas are likely to take more than three to five years to financially realize. Plus, the most disruptive innovation usually begins in a niche market with a substandard product. These factors effectively conspire to sabotage our interim financial performance. So we pursue less disruptive innovation as a result. Luckily, as noted, the startup ecosystem has evolved to close the gaps.

And any other robust initiative among the four shared in the opening is similarly affected. We can always find an excuse to prioritize a project of smaller scope as a tradeoff for more immediate impact, even if it’s marginal (Christensen’s Sustainable Innovation).

These transformations are massively infrastructural.

Several years ago, in the context of graduating founders to a new role, I summarized in a separate post what I thought were the critical functions of a CEO. One of them is to oversee the development and maintenance of organizational infrastructure: culture, people, structure, process, (decision support) systems, real estate and many other essential elements that form the engine of how a company operates. Those who do this well will scale easily, remain agile and secure employee well-being.  Sadly, far too many leaders occupy themselves with shorter-term business results, because this is where they are directly rewarded and is also historically the skill set that tends to sustain career momentum.

Consequently, matters of infrastructure are sectioned off and syndicated to departments that function more administratively relative to others in the organization.

For an infrastructure to work well and even be a competitive advantage, it has to be a coordinated effort. Real estate/remote work and EDI is not effective without process, culture, systems and structure innovation all collaborating in one system of policy or purpose. So to implement effective change in these areas requires an incredible amount of coordination among departments with only nominal influence if the initiatives are not championed by the C-Suite.

Innovation isn’t brainstorming – it’s roles, process, culture and performance measurement. We have to crave to have our thinking challenged and reward prudent failure. So far, we’re not ready to do that.

Productivity is particularly problematic. I won’t go into detail but will instead link one of my favorite business articles of all time on the challenges of getting stuff done efficiently. In short too many leaders see productivity as an individual pursuit – ‘time management’ they call it – a total fallacy. Productivity is similarly not attained through software installation, but rather the result of rebooting all the infrastructural elements highlighted. The software is but a tool. The role of leaders is to strategize and adapt the organization to make best use of it.

Someday I’ll circle back with links to all the HBR articles I have read on why diversity initiatives fail. Short story – creating an inclusive culture is a massive undertaking; it must be seen as such and championed by passionate and invested leaders.

Change management skill void.

Now this one will really sound like excuse-making but I have to call it out because I think it’s a real problem. Meaningful change does not happen for a host of reasons highlighted here, but also because there are not enough experts on hand to cause it. The terms we use in the org behavior courses I teach are Transformational vs Managerial Leadership. The former knows how to create a long-term vision for transformation and then implement it. The latter can plan, set goals and coach people through more short-term activities. Organizations do a much better job at nurturing and rewarding Managerial Leadership styles; as a consequence the more transformational projects tend to fizz out.

Change management involves long-term planning and implementation of in many cases a complete reorganization of key infrastructural elements. It’s like building and launching a complicated flagship product. Beyond planning it requires phases of launch, reinforcement and reward management of substantial scope. From earlier, if you’re not structured and resourced to manage your infrastructure and then also lack the necessary skill, you quite frankly won’t go far. No, a town hall, an email blast, posters and buttons just won’t cut it.

This is what makes me nervous about effective EDI implementation.  I’m all for engaging outside experts to inform the process. The challenge is, they may need to come with not only subject matter expertise but also a track record of change management experience or their valuable insights could go to waste. I have been in a number of focus groups, webinars and other forums on the subject. I see a lot of advocacy and information sharing, however the formation of a sequential playbook or an action plan remains far, far in the distance.

Virtue Signalling.

You can think of this like ‘branding’ or in worse cases ‘lip service’. There are many companies that somehow feel they can get further with a new coat of paint in the form of corporate communication than do all that it takes to back it up. The objective behind this is likely a bump in credibility or favorable opinion.

As a result, we will see many companies market themselves as entrepreneurial yet they have no process to nurture innovation, nor do they empower employees to take risks. The lip service behind DEI is complicated in that it could be a blatant attempt at more relevant branding but could also start with genuine intent followed by hangups in one or more of the factors cited here. Hard to be sure unless you’re in the right meetings on the inside.

Employment Leverage.

Power dynamics play a substantial role in HR policies and practices. I know for remote work the narrative seems to be that employees will demand workplace flexibility because so many are now used to it, they value it and they will come to expect it.

But my question is, why, in a post-pandemic recession will employers take on all that is needed to accommodate it? I do recognize that opportunities can open up for large companies that hire in bulk. As for the rest, the answer to me remains the same as it did pre-pandemic: supply and demand for that particular job will continue to inform policy. Rules will be largely the same. So if you are a smaller company with less cache, you will need to step up your offering. If you have a specialized skill or are an elite performer, you call more of the shots on working conditions. If you are a generally-liked company hiring any one of the other 95% of us, employment conditions are much less negotiable. And in a post-pandemic recession this will be even more the case.

So if you’ve moved to the lake and can only take on remote jobs, your subset of employers will greatly reduce unless you bring something unique to the table. For less specialized roles, expect most employers to feel confident they can source in incumbent locally or make only a handful of exceptions.

The power game will boil down to leaders asking themselves what happens if they don’t build a remote-work culture or implement EDI strategies (absent of third party incentives or government regulation, which I see signs of happening but will factor out for now). If the answer isn’t compelling, we shouldn’t count on the commitment.

People Strategy.

In the cases where employees do not possess the necessary leverage, the game of attracting and retaining people takes on a specific flavor. Much like how in business we concede little on price until customers stop buying, we might similarly approach the working environment with a ‘just good enough’ approach to meeting staffing objectives.

See, there are countless value-adds that can cause an employee to join or remain with a company. These motivators as we call them are both extrinsic (compensation, benefits, perks, role, etc.) or intrinsic (Daniel Pink argues for Freedom, Mastery and Org Purpose as the big 3, which dovetails nicely with my 2015 post on the subject that does call out inclusion btw). There are many other culture elements that tend to lure people to a job as well. The hard truth is that there are innumerable levers for employers to pull – and many are simple to deploy — to motivate employees. And so far, EDI policies have not yet proven to have risen to the top of the list of deal makers and breakers. Unless preferences change substantially, we risk employers consciously or subconsciously evaluating how they prioritize overhauling a company and its culture when there might be easier paths to achieving staffing objectives.

The nature of traditional business culture.

Although I am hopeful we are on our way of purging some of this, there remains some prevalent mindsets and habits relative to workplace expectations that we still need to shed.

The first is that time is something you willingly surrender to progress, so to innovate to give time back to employees is automatically counter culture. Far too many leaders believe that embracing the grind is a rite of passage we all must experience; such narratives are sadly familiar in companies of all sizes and life stages.  We do see cursory head-nods to time wasting but I’ll believe an org is serious about it when I start to see real action on wasteful synchronous meetings. The storied Gitlab is taking this on, combining remote work with migration to asynchronous work in an broadscale transformation led by an empowered head of Remote Work.

The second is appearing more in digital narratives in communities I’m a part of. The contemporary term is toxic positivity. I see it as one of the authentic approaches to lazy leadership – positioning people who speak up for change as being the problem. In toxic positive cultures, leaders use positivity that is not authentic as a tool for influence (and even oppression in the most dramatic cases). If you resist going to a useless meeting, you are labeled a team player. If you make your voice heard where it’s otherwise not, you’re rocking the boat. It’s a tool for compliance where leaders can demand you be better, but the reverse is not allowed; you are expected to like it. At the core of this phenomenon is the underlying belief that convergence > divergence, a flawed assumption that thwarts innovation and diversity from the get-go.

The final cultural/leadership norm is that the best change is grassroots. It can be, but needs to be resources and championed. Otherwise, it’s simply delegated to people who do not have the capacity to lead massive side projects that may not be endorsed by those who sign their paychecks. As a result the grassroots movements that do form can often take on a negative tone, born out of frustration and sheer loss of patience. Not optimal and not always constructive.


OK. Yeah. That’s a lot. And it needs to be seen that way, because there is a lot that’s in the way of creating a new vision for how we run companies and how we work. As I said, I’m not here to excuse anything – quite the opposite – but instead feel that meaningful change has to first come from a place of understanding, as frustrating as the obstacles are. Political leaders are reflecting, and now championing a great reset of our economies as we work to emerge from the pandemic. I trust that across organizations, we can do the same.

We have a long way to go, but I’m optimistic we can get there. I have seen and been a part of significant efforts in all of these areas, so I know the templates are there. The critical element is leadership (always starts at the top!) with more vision, empathy and altruism. We see this most in the entrepreneurial space; unfortunately, startups face massive risk to survival before best practices are established.

The best organizational moves deliver business results and promote employee well-being. Both can be massively served through more consistent attention to the most important transformations not yet addressed, and what’s more could be weaponized for competitive advantage to those who ultimately recognize the potential.

I am both trusting and hoping that events particularly over the last year will direct us to the most powerful opportunities to create a better workplace – and with it, perhaps an even better world.