There are several types of chaotic work cultures. You mentioned a management that quite hands off.
Another type is where salespeople are running the show and multiple priorities happen all the time, "emergency fixes" need to be made "right now so that we get this sale" or "so that the client doesn't fire us", and there is no time to plan or have a software architecture. This type of company will succeed as sales will continue to happen, but the "technical debt" will pile up like crazy. What happens is that the software grows in complexity because of all the patches.
So, the questions I recommend are:
Do you plan out software development?
How are "emergency requests" from sales handled?
Are people given time to clean up technical issues from past emergencies?
What happens when a VP says to "fix this right now"? Do people sit down and plan how that fits into the architecture or does someone write code and present a "solution" in 15 minutes?
How many times does an upgrade break a fix that was done for a specific client and how do those situations get handled?
How many times do clients report that the process broke down on their order? (I had one client where the order process was hacked together by a previous person, and it would occasionally drop part of an order due to not handling an SQL lock error but never report any error. When the system dropped 80% of a $100,000 order, the client was not happy.)
How often do people have to work holidays in order to salvage a project? (I worked one 36-hour shift over a Labor Day weekend.)
How does working here affect people's relationships?
Does this place have plans for handling ransomware attacks? (If you want to see chaos, watch what happens when ransomware attacks.)
What is the attitude of other departments towards IT? Are they happy with the solutions or are they trying to find their own solutions? (You might be surprised at how many sales departments want to hire their own developers to get solutions or how many HR departments are researching outside vendors to replace the internal system.)