Part-time owners, full-time debt

Organizations are accumulating a type of debt that no one has been hired to pay down.

At Vercel, I was brought in to handle some of this debt, but not all of it. The last year helped me understand just how much of this debt exists at every company I’ve worked with or for, and how rare it is for someone to be hired to handle it.

Organizational debt (and maintenance more broadly) keep coming up in conversations I’m having as people have turned the AI slop cannon dials to 11 and we’re starting to feel the reality of letting people plant anything. Somehow, this recent LinkedIn post from Dan Hockenmaier about org debt showed up in my feed and here I am revisiting ideas from Stewart Brand and Clay Parker Jones about how organizations learn at different speeds. TLDR: the fast layers (execution, the next 90 days) get all the attention while the slow layers (functional advantage, vision, the next 5-20 years) hold all the power.

I find debt fascinating, because different types of debt become visible on different time scales. If slow holds all the power and the debt that accumulates there is both expensive and invisible — who is paying it down?

At Vercel, I was responsible for a meeting I did not own.

Every Monday, the leaders from our EPD and GTM organization would review what has shipped and will ship soon, as well as whatever other topics needed attention that week. The meeting was owned by our CPO, but the meeting working, that is, making sure the right context was shared beforehand, that the right people were present, and the right decisions were captured and followed up on — that was my responsibility.

Our EPD Org all hands meeting was similar. I helped create it. I would set agendas and prepare the presenters. I would work with EAs to get the right people scheduled. The all hands was owned by EPD leadership, but the all hands working was my responsibility.

I think it’s easy to look at what I’m describing and assume that it’s chief of staff work. Every CoS role is different, though many of them spend their time managing someone’s time and attention, acting as an extension of their principal. Making sure a ritual is useful and successful is not just managing time and attention for one person, it’s taking responsibility for the organization’s ability to understand itself.

I was paying down the debt of organizational misunderstanding.

Every company has this debt, and most companies are both accumulating it faster than they realize and do not recognize it as debt. This is the result of decisions being made with the wrong people in the room, information that loses fidelity as it traverses the organization, and teams building duplicative things because they didn’t communicate rather than by design. None of this is anyone’s fault necessarily, it’s simply the result of growth in an organization that wasn’t ready to handle it.

The way you pay down this debt is by building the right rituals that create surface area for understanding among the right people at the right time. Those rituals work because they have someone to tend to them — someone to think intentionally about why it exists on people’s calendars, how it can be more valuable, what shape it needs to take, and redesigns or sunsets them when they are no longer working.

But at most companies, this work is no one’s job. Making sure a ritual works is probably the fifth or sixth priority for most people. Everyone cares about it, but no one is doing the operational work of building and tending to these rituals because they are doing the work that their title actually demands. The debt of organizational misunderstands compounds quietly in the background, accruing slow enough to never be on anyone’s radar, until it shows up in the symptoms that everyone recognizes. The strategy doesn’t make sense. Teams are doing the same work. Decisions are being revisited.

Work has become theater.

At an organization, this work cannot be a part time job. You cannot pay down this kind of debt with the fraction of an executive’s time in the same way you cannot tend to a garden only once a quarter. Designing the right rituals, running them, auditing them, and sunsetting them need to be someone’s full time responsibility or they do not happen.

The companies that have figured this out have hired for it. I was brought to Vercel because leadership understood that the things that worked at 300 people were not working at 600. The rituals that carried the company through earlier periods were insufficient for the work ahead and someone needed to own the work of building the new rituals. Vercel didn’t have some secret playbook, they just had awareness of the problem and the willingness to do something about it.

Jaya Gupta has argued that in an era when products and technical advantages get copied in weeks, the shape of the organization is itself the moat. Most companies have the same problem Vercel did, and most of them have not named it. When we assume that the executive closest to the debt is both accountable and responsible for paying down debt they don’t have the individual capacity to handle, we fail to acknowledge that the work will fall to whoever in the organization cares to do something about it.

The reason this matters is that the debt is getting worse, not better. (I’m sorry to say, but agents are not coming to save you.) Every organization is producing more than ever. More launches, more rituals, more decisions, more tools, more people. And the rate at which a company accumulates this debt is not linear.

You probably know where this is happening at your company. You see new hires asking the same questions as they ramp up and getting different answers. You see a tool that no one remembers adopting and no one is willing to do the work of replacing. You’re a part of a recurring conversation about how “we should be better about X” that happens every quarter and no one takes action on.

None of these are the debt themselves, they are simply the surfaces on which the debt is visible. The debt is underneath, accumulating at the slow layers, on a horizon no one has the bandwidth to attend to.

The harder question is not whether you recognize any of this (you almost certainly do), but whether anyone at your company has been hired to do anything about it.