This is a re-publishing of a blog post I originally wrote for work, but wanted on my own blog as well.

AI is everywhere, and its impressive claims are leading to rapid adoption. At this stage, I’d qualify it as charismatic technology—something that under-delivers on what it promises, but promises so much that the industry still leverages it because we believe it will eventually deliver on these claims.

This is a known pattern. In this post, I’ll use the example of automation deployments to go over known patterns and risks in order to provide you with a list of questions to ask about potential AI solutions.

I’ll first cover a short list of base assumptions, and then borrow from scholars of cognitive systems engineering and resilience engineering to list said criteria. At the core of it is the idea that when we say we want humans in the loop, it really matters where in the loop they are.

My base assumptions

The first thing I’m going to say is that we currently do not have Artificial General Intelligence (AGI). I don’t care whether we have it in 2 years or 40 years or never; if I’m looking to deploy a tool (or an agent) that is supposed to do stuff to my production environments, it has to be able to do it now. I am not looking to be impressed, I am looking to make my life and the system better.

Another mechanism I want you to keep in mind is something called the context gap. In a nutshell, any model or automation is constructed from a narrow definition of a controlled environment, which can expand as it gains autonomy, but remains limited. By comparison, people in a system start from a broad situation and narrow definitions down and add constraints to make problem-solving tractable. One side starts from a narrow context, and one starts from a wide one—so in practice, with humans and machines, you end up seeing a type of teamwork where one constantly updates the other:

The optimal solution of a model is not an optimal solution of a problem unless the model is a perfect representation of the problem, which it never is.
 — Ackoff (1979, p. 97)

Because of that mindset, I will disregard all arguments of “it’s coming soon” and “it’s getting better real fast” and instead frame what current LLM solutions are shaped like: tools and automation. As it turns out, there are lots of studies about ergonomics, tool design, collaborative design, where semi-autonomous components fit into sociotechnical systems, and how they tend to fail.

Additionally, I’ll borrow from the framing used by people who study joint cognitive systems: rather than looking only at the abilities of what a single person or tool can do, we’re going to look at the overall performance of the joint system.

This is important because if you have a tool that is built to be operated like an autonomous agent, you can get weird results in your integration. You’re essentially building an interface for the wrong kind of component—like using a joystick to ride a bicycle.

This lens will assist us in establishing general criteria about where the problems will likely be without having to test for every single one and evaluate them on benchmarks against each other.

Questions you'll want to ask

The following list of questions is meant to act as reminders—abstracting away all the theory from research papers you’d need to read—to let you think through some of the important stuff your teams should track, whether they are engineers using code generation, SREs using AIOps, or managers and execs making the call to adopt new tooling.

Are you better even after the tool is taken away?

An interesting warning comes from studying how LLMs function as learning aides. The researchers found that people who trained using LLMs tended to fail tests more when the LLMs were taken away compared to people who never studied with them, except if the prompts were specifically (and successfully) designed to help people learn.

Likewise, it’s been known for decades that when automation handles standard challenges, the operators expected to take over when they reach their limits end up worse off and generally require more training to keep the overall system performant.

While people can feel like they’re getting better and more productive with tool assistance, it doesn’t necessarily follow that they are learning or improving. Over time, there’s a serious risk that your overall system’s performance will be limited to what the automation can do—because without proper design, people keeping the automation in check will gradually lose the skills they had developed prior.

Are you augmenting the person or the computer?

Traditionally successful tools tend to work on the principle that they improve the physical or mental abilities of their operator: search tools let you go through more data than you could on your own and shift demands to external memory, a bicycle more effectively transmits force for locomotion, a blind spot alert on your car can extend your ability to pay attention to your surroundings, and so on.

Automation that augments users therefore tends to be easier to direct, and sort of extends the person’s abilities, rather than acting based on preset goals and framing. Automation that augments a machine tends to broaden the device’s scope and control by leveraging some known effects of their environment and successfully hiding them away. For software folks, an autoscaling controller is a good example of the latter.

Neither is fundamentally better nor worse than the other—but you should figure out what kind of automation you’re getting, because they fail differently. Augmenting the user implies that they can tackle a broader variety of challenges effectively. Augmenting the computers tends to mean that when the component reaches its limits, the challenges are worse for the operator.

Is it turning you into a monitor rather than helping build an understanding?

If your job is to look at the tool go and then say whether it was doing a good or bad job (and maybe take over if it does a bad job), you’re going to have problems. It has long been known that people adapt to their tools, and automation can create complacency. Self-driving cars that generally self-drive themselves well but still require a monitor are not effectively monitored.

Instead, having AI that supports people or adds perspectives to the work an operator is already doing tends to yield better long-term results than patterns where the human learns to mostly delegate and focus elsewhere.

(As a side note, this is why I tend to dislike incident summarizers. Don’t make it so people stop trying to piece together what happened! Instead, I prefer seeing tools that look at your summaries to remind you of items you may have forgotten, or that look for linguistic cues that point to biases or reductive points of view.)

Does it pigeonhole what you can look at?

When evaluating a tool, you should ask questions about where the automation lands:

• Does it let you look at the world more effectively?
• Does it tell you where to look in the world?
• Does it force you to look somewhere specific?
• Does it tell you to do something specific?
• Does it force you to do something?

This is a bit of a hybrid between “Does it extend you?” and “Is it turning you into a monitor?” The five questions above let you figure that out.

As the tool becomes a source of assertions or constraints (rather than a source of information and options), the operator becomes someone who interacts with the world from inside the tool rather than someone who interacts with the world with the tool’s help. The tool stops being a tool and becomes a representation of the whole system, which means whatever limitations and internal constraints it has are then transmitted to your users.

Is it a built-in distraction?

People tend to do multiple tasks over many contexts. Some automated systems are built with alarms or alerts that require stealing someone’s focus, and unless they truly are the most critical thing their users could give attention to, they are going to be an annoyance that can lower the effectiveness of the overall system.

What perspectives does it bake in?

Tools tend to embody a given perspective. For example, AIOps tools that are built to find a root cause will likely carry the conceptual framework behind root causes in their design. More subtly, these perspectives are sometimes hidden in the type of data you get: if your AIOps agent can only see alerts, your telemetry data, and maybe your code, it will rarely be a source of suggestions on how to improve your workflows because that isn’t part of its world.

In roles that are inherently about pulling context from many disconnected sources, how on earth is automation going to make the right decisions? And moreover, who’s accountable for when it makes a poor decision on incomplete data? Surely not the buyer who installed it!

This is also one of the many ways in which automation can reinforce biases—not just based on what is in its training data, but also based on its own structure and what inputs were considered most important at design time. The tool can itself become a keyhole through which your conclusions are guided.

Is it going to become a hero?

A common trope in incident response is heroes—the few people who know everything inside and out, and who end up being necessary bottlenecks to all emergencies. They can’t go away for vacation, they’re too busy to train others, they develop blind spots that nobody can fix, and they can’t be replaced. To avoid this, you have to maintain a continuous awareness of who knows what, and crosstrain each other to always have enough redundancy.

If you have a team of multiple engineers and you add AI to it, having it do all of the tasks of a specific kind means it becomes a de facto hero to your team. If that’s okay, be aware that any outages or dysfunction in the AI agent would likely have no practical workaround. You will essentially have offshored part of your ops.

Do you need it to be perfect?

What a thing promises to be is never what it is—otherwise AWS would be enough, and Kubernetes would be enough, and JIRA would be enough, and the software would work fine with no one needing to fix things.

That just doesn’t happen. Ever. Even if it’s really, really good, it’s gonna have outages and surprises, and it’ll mess up here and there, no matter what it is. We aren’t building an omnipotent computer god, we’re building imperfect software.

You’ll want to seriously consider whether the tradeoffs you’d make in terms of quality and cost are worth it, and this is going to be a case-by-case basis. Just be careful not to fix the problem by adding a human in the loop that acts as a monitor!

Is it doing the whole job or a fraction of it?

We don’t notice major parts of our own jobs because they feel natural. A classic pattern here is one of AIs getting better at diagnosing patients, except the benchmarks are usually run on a patient chart where most of the relevant observations have already been made by someone else. Similarly, we often see AI pass a test with flying colors while it still can’t be productive at the job the test represents.

People in general have adopted a model of cognition based on information processing that’s very similar to how computers work (get data in, think, output stuff, rinse and repeat), but for decades, there have been multiple disciplines that looked harder at situated work and cognition, moving past that model. Key patterns of cognition are not just in the mind, but are also embedded in the environment and in the interactions we have with each other.

Be wary of acquiring a solution that solves what you think the problem is rather than what it actually is. We routinely show we don’t accurately know the latter.

What if we have more than one?

You probably know how straightforward it can be to write a toy project on your own, with full control of every refactor. You probably also know how this stops being true as your team grows.

As it stands today, a lot of AI agents are built within a snapshot of the current world: one or few AI tools added to teams that are mostly made up of people. By analogy, this would be like everyone selling you a computer assuming it were the first and only electronic device inside your household.

Problems arise when you go beyond these assumptions: maybe AI that writes code has to go through a code review process, but what if that code review is done by another unrelated AI agent? What happens when you get to operations and common mode failures impact components from various teams that all have agents empowered to go fix things to the best of their ability with the available data? Are they going to clash with people, or even with each other?

Humans also have that ability and tend to solve it via processes and procedures, explicit coordination, announcing what they’ll do before they do it, and calling upon each other when they need help. Will multiple agents require something equivalent, and if so, do you have it in place?

How do they cope with limited context?

Some changes that cause issues might be safe to roll back, some not (maybe they include database migrations, maybe it is better to be down than corrupting data), and some may contain changes that rolling back wouldn’t fix (maybe the workload is controlled by one or more feature flags).

Knowing what to do in these situations can sometimes be understood from code or release notes, but some situations can require different workflows involving broader parts of the organization. A risk of automation without context is that if you have situations where waiting or doing little is the best option, then you’ll need to either have automation that requires input to act, or a set of actions to quickly disable multiple types of automation as fast as possible.

Many of these may exist at the same time, and it becomes the operators’ jobs to not only maintain their own context, but also maintain a mental model of the context each of these pieces of automation has access to.

The fancier your agents, the fancier your operators’ understanding and abilities must be to properly orchestrate them. The more surprising your landscape is, the harder it can become to manage with semi-autonomous elements roaming around.

After an outage or incident, who does the learning and who does the fixing?

One way to track accountability in a system is to figure out who ends up having to learn lessons and change how things are done. It’s not always the same people or teams, and generally, learning will happen whether you want it or not.

This is more of a rhetorical question right now, because I expect that in most cases, when things go wrong, whoever is expected to monitor the AI tool is going to have to steer it in a better direction and fix it (if they can); if it can’t be fixed, then the expectation will be that the automation, as a tool, will be used more judiciously in the future.

In a nutshell, if the expectation is that your engineers are going to be doing the learning and tweaking, your AI isn’t an independent agent—it’s a tool that cosplays as an independent agent.

Do what you will—just be mindful

All in all, none of the above questions flat out say you should not use AI, nor where exactly in the loop you should put people. The key point is that you should ask that question and be aware that just adding whatever to your system is not going to substitute workers away. It will, instead, transform work and create new patterns and weaknesses.

Some of these patterns are known and well-studied. We don’t have to go rushing to rediscover them all through failures as if we were the first to ever automate something. If AI ever gets so good and so smart that it’s better than all your engineers, it won’t make a difference whether you adopt it only once it’s good. In the meanwhile, these things do matter and have real impacts, so please design your systems responsibly.

If you’re interested to know more about the theoretical elements underpinning this post, the following references—on top of whatever was already linked in the text—might be of interest:

• Books:
  • Joint Cognitive Systems: Foundations of Cognitive Systems Engineering by Erik Hollnagel
  • Joint Cognitive Systems: Patterns in Cognitive Systems Engineering by David D. Woods
  • Cognition in the Wild by Edwin Hutchins
  • Behind Human Error by David D. Woods, Sydney Dekker, Richard Cook, Leila Johannesen, Nadine Sarter
• Papers:
  • Ironies of Automation by Lisanne Bainbridge
  • The French-Speaking Ergonomists’ Approach to Work Activity by Daniellou
  • How in the World Did We Ever Get into That Mode? Mode Error and Awareness in Supervisory Control by Nadine Sarter
  • Can We Ever Escape from Data Overload? A Cognitive Systems Diagnosis by David D. Woods
  • Ten Challenges for Making Automation a “Team Player” in Joint Human-Agent Activity by Gary Klein and David D. Woods
  • MABA-MABA or Abracadabra? Progress on Human–Automation Co-ordination by Sidney Dekker
  • Managing the Hidden Costs of Coordination by Laura Maguire
  • Designing for Expertise by David D. Woods
  • The Impact of Generative AI on Critical Thinking by Lee et al.