This is good problem-solving. Why spend tens (if not hundreds) of thousands of dollars building technology to do a complicated task if you can cut that effort in half or more by having somebody where a funny vest?
Remember, the problem is "I need to know when I don't have two managers on the floor," not "how do I use machine learning to know when I don't have two managers on the floor."
This particular problem is "I need to know when I don't have two managers on the floor, and they aren't always wearing funny vests just because the computer guys are bad at deep learning".
If we can make up arbitrary rules and assumptions then just have them jot down on a piece of paper when they come and go, and if they are the last to leave then they have to send an email.
I don't think they are making up arbitrary rules, I think it's problem solving. Brainstorming alternative solutions that are cost effective and solve the problem is a useful exercise. We shouldn't just blindly use machine learning because it's there.
Honestly, despite your facetiousness, this is the best starting point. And then from here work up to more complex solutions if there are reasons why rhis simple one isn’t suitable
This wouldn't work as there is a time requirement of 20 minutes. A solution to this would have to be real-time and not require one to manually log their presence, which would defeat the whole point.
The problem with supervisors was just an example. The person asking the question isn't served by simplifying the problem, because clearly they are after a more general solution.
The requirements were not changed. Supervisors of almost every working class position already wear different clothes to begin with. Heck, even doctors wear different clothing than nurses, teachers than students, coaches from athletes, etc.
The general point is to capitalize on preexisting information than to do the "true" solution which is error prone and even a human might not have 100% accuracy at, due to the fact that in certain settings (such as this hypothetical) the perfected solution cannot be accomplished without constraints.
This solution would change the work place culture - and I 100% bet would lead to a lot of good (for MY definition of good!) supervisors leaving.
Imagine where you worked suddenly introduced this: "Yes, previously everyone could wear whatever they wanted - but from today, just the senior programmers must code while wearing a high-vis jacket around the office so we can track when they at their desks".
The supervisors have now changed their relationship with coworkers - signaling their superiority, while simulataneously feeling stalked by their bosses, and looking "unfashionable"/un-cool - all because someone couldn't figure out how to do deep learning properly... which was the OP was actually asking about!
1. Supervisors are already by definition "superior" than their subordinates.
2. Supervisors on factories already wear distinctive clothing - especially in fully automated factories.
Finally, you have yet to propose a solution to the problem yourself that would be highly accurate and easy to train. You vastly underestimate the difficulty to create a bespoke solution from scratch and no data.
In any case since the supervisor thing was just an example - the original poster's only real choice is to manually label everything, but AI is really problem centric so it's hard to recommend anything without knowing the actual problem. Assuming it really is just [someone in an area for a period of time] kind of problem, and the difficulty is picking apart the 'someone' and you cannot influence their behavior, you just need massive amounts of data. Even then there's no guarantee you'll have high accuracy.
If high accuracy is required the problem itself needs to be examined on a higher level.
I don't have a deep-learning solution to the problem (I know nothing about it, that's why I clicked on it!). Seems really hard to me. I'd certainly go with an obvious "clock in and out" or "rfid" approaches... but I've worked in factories - and if you make someone wear some special clothes (or do some special tasks) when they didn't have to before - you're asking for trouble. People really hate change. That's presumably why the OP was looking for an answer for a tough problem.
A nerd analogy would be making a programmer change OSs (or even text editors) against their will: They could do it, but they won't be very happy about it.
"nerd", "computer guys bad at..." it feels like you have an irrational axe to grind here, when a simple solution presented causes this line of argument.
Remember, the problem is "I need to know when I don't have two managers on the floor," not "how do I use machine learning to know when I don't have two managers on the floor."