Romans, Middle Managers and AI. What Block Gets Wrong About the Future of Teams

The title, Romans, Middle Managers and AI sounds like the start to a bad joke. It's actually the story of a poorly formed organizational structure, deemed as the innovative future by Sequoia capital's Roelof Botha and Block's Jack Dorsey.

I got a bit riled up after I read Dorsey and Botha’s 31st March article “From Hierarchy to Intelligence.”

The primary issue is their theory of middle management is flawed and it lays the groundwork for misconceptions that unfortunately allow them to perpetuate some of the worst problems our middle managers face.

It opens with a historical recounting of how today’s corporate hierarchy was conceptualized by the Roman military out of necessity. They had to figure out a way to share information over vast territory.

No cell phones.

I didn’t know this history nor the additional iterations that came from more war (Prussian) and then shifted to commercialized entities (American railroads) eventually being optimized by Frederick Taylor and then enhanced by numerous management entities.

You’re not snoozing are you?  I find this quite interesting. Dorsey and Botha wrote a really good piece, weaving history and work and theoretical innovation.

But it’s not the point of this article. The history didn’t rile me up. It’s their proposed innovative organization design at Block that did it.

Their central argument is that hierarchy was created and exists for the primary purpose of routing information across layers that are too large for any one person to oversee.  They’re positing that AI enables an entirely new model, a replacement for this centuries-old hierarchy, one that will revolutionize how companies get work done.

Meanwhile they make some huge assumptions and declarations. Specifically, they indicate that middle management is merely a bunch of people who relay information, sit in meetings, and jockey priorities across the organization.

Wow.

This description is overly simplistic and limited in its understanding of how good management structures align and contribute. It completely ignores the tacit knowledge, the situational judgement, relationships, and focus on improving individuals and as a consequence the organization. Well, it ignores that part until it reframes it as if it were an entirely different beast in a new role of Player-coach. But we’ll get to that.

To be fair, bad management is real and widespread. We recognize that this middle management layer is a leading contributor to both our major successes and our biggest missteps. Largely that’s because of who’s in the layer, how they got there, and how they are (not) treated.

Middle management is often composed of individuals promoted without management experience or expertise in leading others. They come from a hodgepodge of backgrounds and perspectives. And, we place an inordinate expectation on them to figure things out & take initiative, while simultaneously asking them to toe the line, follow senior direction and regurgitate what they think they heard to the masses around and underneath them in the hierarchy.

The original expectation of middle management, as described in Dorsey’s and Botha’s article, is that we just needed enough people to connect across spans and distances to relay communications and decisions. Through trial and error, Romans found a kind of magical number of subordinates that “most” managers could handle, which allowed for aggregated information to disseminate, somewhat consistently, through the ranks.

What a limiting explanation of what these people did.

And Block’s proposed new approach to people management is STILL serving up the same limited understanding of the manager’s role and responsibilities.

Middle management does have the formidable challenge of interpreting from above, disseminating across and below. The really good managers also influence across these same directions and layers. More importantly they listen, solicit feedback and perspective, and cross pollinate that information so that the leaders at the top have more informed insights and the layers and levels get the specificity and quantity they need without the noise and irrelevant details.

And yes, many, many managers (individuals and leaders) are not yet great at this. They have much more to learn and finesse in regards to their communication abilities.

However, what we need to drill down on is the premise that this is all middle management does. That as suggested in the article, they waste time in meetings and determining priorities.

Even the Romans are unfairly dismissed. How simplistic is the view that the Decanus, a manager of a team of eight, or a Centurion, a manager of 10 teams of eight each, were just relaying information up and down the line.

You can imagine as well as I can. One Centurion encouraged teams to be forward thinking and to take initiative. They were often known as the best squad in the area. Another was power-hungry and a control freak, punishing any team member or manager who stepped out of permitted roles.

And still, even in the most restrictive environment, those managers had to communicate, to listen, to correct, to guide. The really good ones were harnessing energy, soliciting feedback and perspective, and honing the eight individuals to bring their unique strengths into play in a way that tightly aligned the group to work as a unit, as part of the nine other teams in the centurion and under the command of a broad and powerful organization.

That Block interprets middle managers then and now as participants in a relay race is the heart of the issue. Block appears unable to perceive the nuances beyond the premise that a manager’s “primary job is information routing.” It’s this lack of understanding about the value (or the harm) that these managers bring to an organization that mis-serves all of us and it’s likely going to cause Block to stumble in their new approach.

I’ll set aside some of the arguments that I’m unqualified to debate, hoping some others might take up the mantle. The ideas that money is the source of truth, the complete disregard for moral obligations to workers, to humans, to society and community and the flawed allusion that the new model will empower everyone.  These make me grind my teeth. We need to care more about how our decisions and actions impact real people, real societies. Our end game isn’t, or shouldn’t be, only efficiencies and using technology to get “deeper understanding” with no real human centered benefit or goals.

What I am suited to debate are the issues surrounding the arguments on middle management or how oblivious the new edge structure appears to be.  Block is proposing technology as the central intelligence with people at the edge in one of three roles:

Individual contributors (ICs) – specialist worker bees who can “make decisions without being told what to do”

Geez, they REALLY don’t get how good teams work.

Comically, ICs appear to be allowed to go ahead and punt the hard stuff over to the DRIs, no need for them to be directly responsible.

Directly responsible individuals (DRIs) – folks who get to own and solve problems & opportunities.

Hmm. You know what we call those today?

But wait for it, this next one slays me…

Player-coaches – “combine building with developing people”

 Record scratch. Pause.

I’d like to take a moment to remind you that Block just preemptively terminated over 4K employees.

They did that in anticipation that this new model would be advantageous.

 And now back to our scheduled programming.

Yet, they still have the mystifyingly obtuse idea that they’ll have player-coaches.

People who have real work obligations and responsibilities AND who get to teach and coach and guide other people. “They invest in the growth of the people around them.”

 Who’s gonna tell them?

The best they can come up with in this new regime structure is to perpetuate one of the biggest issues our middle management and workforce face today… the expectation that a manager will do all the work equivalent to an individual contributor while simultaneously “investing in the growth of the people around them.”

Why? Why would I do that job in the future?

It’s already the burden of our managers today.

And today they do it for the quasi-guarantee of a job and the potential chance of promotion, increased authority, influence, experience and pay.

Why would Block assume that it is innovative to create a role where other employees get to do their job and be done, but a Player-coach gets to do their job and help other people get along, interact with the organization and the customers, and probably gets to go in the server room and check on the electrical grid while they’re at it.

Dang, aren’t we tired of this attitude?

Our middle managers are already overburdened. The best Block could come up with was a narrow and limited interpretation of the purpose of the middle manager while simultaneously side-eyeing the reality that we need people to “invest in the growth of the people around them” …apparently off the side of their desk.

This innovative new-world organization both minimizes the importance of humans and still expects a manager to do more than everyone else and help them learn to do it better?

The Player-coach is not innovative. It’s the oldest labor arrangement in corporate history, asking someone to lead, mentor and perform while providing limited support or guidance. The role inherits every burden of middle management that exists today.

Block describes the edge as “intuition, opinionated direction, cultural context, trust dynamics, the feeling in a room.” It just fails to realize and admit that managers are the ones who facilitate or inhibit this in today’s workplace. With bad management or no management, those capacities often atrophy or concentrate in the most politically visible individuals. With good management, people thrive and harness these attributes across teams and the organization.

I think it’s safe to say that Dorsey is also completely discounting his own creativity, leadership and contributions. Since executive leadership is entirely ignored in the model, we can only assume that it’s up to those player-coaches to determine how to structure work so that human capacities are developed, evaluated, and protected. Goodness knows who’s gonna talk to the investors.

If your organization is full of middle managers who relay information, sit in meetings, and jockey priorities across the organization, then I argue that it isn’t the structure that is the problem. It’s your expectations, your company values, your convenient lack of accountability at the root of the problem. It’s your leadership and your culture that created and enabled this problem.

Instead of scrapping 4K jobs and designing a new structure that dismisses the importance of human dynamics, reduces value to money and systems, and still asks the manager to do more than most anyone else in the company…maybe take a closer look. Look instead at how you might create alignment within, harness that energy and potential, and redefine expectations, roles, goals and engagement so that we maximize the rarest, most special resource we have on earth: people.

None of this is an argument for preserving hierarchy as-is. Middle management, as practiced in many large organizations, is genuinely dysfunctional not because the people in those roles are inadequate, but because the expectations, accountability structures, and development investments surrounding those roles are. Organizations have consistently promoted people into management without giving them the tools, time, or organizational support to do it well. That is a leadership failure more than an individual or structural one.

I encourage curiosity and innovation. I applaud the disruption that Block is attempting. Given the context they carefully provided to why we should consider dismantling normal, it seems like they’ve spent some time and effort on this.  I appreciate that they admit it may come with failures and issues to learn from. I especially appreciate that they'll consider feedback.

But did anyone ask this intelligent central layer if it even understands how management works, what they do, and whether this new model is truly serving us? 

Approximately 4,000 people lost their jobs in the weeks before this article was published. The article describes this not as a loss but as a structural correction, evidence that the model works.

The people who were laid off are not variables in a model. They are the stakeholders whose lives were restructured by the experiment, and they are not represented in the intellectual framework the article presents. A theory of organizational intelligence that does not account for its human cost, not as sentiment, but as a measurable variable in the model doesn’t do justice to all the factors that make up business and society.

Might we challenge the system and ourselves to think about the value people bring and the right way to honor and hone that?  I’d like Block to feed that into the system and their own perspective.

Take another look at the role of management and leadership, of workers and teams and community and society.  And refocus on what real management accomplishes.