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I echo Marc's comments and will add that an over arching objective of good documentation of this type needs to be based on what the objectives are of the process and then how those objectives are achieved (in code or process). So often, I have seen where massive investments over time have been lost and replaced by lesser effective delivery systems simply due to the fact that the person or persons that assumed the support of those processes was ill-informed of the full story of 'why' this process is as it is and as a result assumes that there are serious gaps that must be corrected or the entire process replaced.
In a high number of these situations, at some point later there is a realization that the legacy process was sufficient and perhaps covered gaps which the replacement process creates. Thereby creating a cycle of waste.
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In addition to the exceptional answer by Marc, as tool I can think of Latex too. My wife wrote Doctor-Thesis on it and results were way better than usual word files. But... it is a bit PITA until you get how to use it, I had to sit down myself and look for examples, try-error myself to get some stuff she wanted done.
Personally I used MS Visio a lot to make relational diagrams, workflows, structure graphics. Afterwards embedded it in Word (company wanted it so)
M.D.V. 
If something has a solution... Why do we have to worry about?. If it has no solution... For what reason do we have to worry about?
Help me to understand what I'm saying, and I'll explain it better to you
Rating helpful answers is nice, but saying thanks can be even nicer.
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I agree with what's already been posted. Make sure you explain the why of your decisions instead of the how. Many developers will explain how something works but they leave out the reason that they chose that solution in the first place. For example:
- Explain why you chose a commercial solution over an open-source solution (or vice-versa)
- Explain any failed attempts at complicated code before arriving at the current solution
- If it's not obvious, explain the problem you were trying to solve with certain pieces of code
Chances are the next developer will be able to work through your code and understand how things work, but typically documentation is the only way to explain why.
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Quote: Chances are the next developer will be able to work through your code and understand how things work, but typically documentation is the only way to explain why.
This is a great point! Thoughtful and useful documentation is hard, which is why we're having this conversation. And we routinely focus our efforts in the wrong place when creating content.
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Wow. When I'm leaving a job I delete comments and rename variables.
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F-ES Sitecore wrote: When I'm leaving a job I delete comments and rename variables.
You may actually be doing everyone a service. Speaking for myself, I know my comments are often outdated with regards to what the code is now doing (that part is more true than humor), and obfuscating variable names is a motivation to work out the code without trusting the programmer named them well and spelled them correctly (again, sadly less humor and more true for code I've had to work with that others wrote.)
Marc
Latest Article - Create a Dockerized Python Fiddle Web App
Learning to code with python is like learning to swim with those little arm floaties. It gives you undeserved confidence and will eventually drown you. - DangerBunny
Artificial intelligence is the only remedy for natural stupidity. - CDP1802
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When I was at the University, one of my fellow students did his hand-in exercizes the other way around (or, I guess it is opposite of your renaming): While writing program code, his integer variables were named I01, I02, ..., float variables F01, F02 etc. He would never wast the line space and typing effort of using those long, descriptive names demanded by the professor. The last edit before handing in the assignment was to replace I01 with NumberOfApplesInEachCrate and F02 with AverageWeightOfEachApple, and so on.
I am not defending his work style, but can't help being impressed by his mental capacity to developp and comprehend quite complex software without the aid of descriptive names.
(My first programming language was BASIC, in those days when it REALLY was basic... Variable names one letter, or one letter and one digit. Programs exceeding 100 lines were big ones. Under those conditions, you can manage without descriptive variable names.)
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F-ES Sitecore wrote: Wow. When I'm leaving a job I delete comments and rename variables.
Surely, you jest ?
The consequences of such an action, depending on your contractual agreement with your employer, and the legal system you are in, could be very serious.
«Beauty is in the eye of the beholder, and it may be necessary from time to time to give a stupid or misinformed beholder a black eye.» Miss Piggy
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Yes, I jest. It's something we call a "joke", an anecdote that probably isn't true but told for amusement 
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... and don't call him Shirley
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There is already a bunch of good advise in the comments. It also becomes obvious that relevant documentation should be kept up to date as good as possible. What if you just leave or create a heap of lorem ipsum stuff? Is anybody gonna review the documents you produce? How likely is it that the next person will just create his own set of documentation and don't even look at what you created? From your question I get also the impression that there isn't any expectation regarding the deliverable from your managers side.
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The documentation will definitely be used. I'll have some training sessions with the person taking over the project as well. Just sometimes difficult to get concepts over onto paper.
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That's good to hear that there will be somebody looking at it! Will you do the documentation with your successor together if possible? By that he can already make himself familiar and provide feedback in a very early stage.
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I'll definitely give him the documentation before I go and ask for feedback and add in extra info as needed.
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Start with a description, in plain English, of the problem you are trying to solve. Next, explain, in plain English, your thinking process in arriving at your chosen solution and outline the pros and cons of that solution. In other words, give the next person an insight into your thinking process.
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Like jgrogan, above, I am not Politically Correct - I think plain English has a definite place in the documentation, as opposed to machine generated, strictly formalized and structured documentation. The latter has its definite place as a dictionary of details for future maintenance, but not to make your follower understand your code.
I draw a line between that which is independent of your implementation tools and the implementation details. Think of the first part as something that won't be changed at all if your system is re-implemented in a different language, one with different mechnamisms. Not that you will switch to another language, but it helps you keep the irrelevant details out of (that part of) the documentation, and focus on the essentials.
It will be fairly stable: You can do a lot of code changes without the algorithms, data structures, functional modularization etc. being changed. Maybe new functions are added and data structures extended, but that rarely has any large impact on the old parts.
The dividing line between implementation independent and dependent details may of course be discussed. E.g, I assume that an algorithmic language will be used for implementation, so I can describe flow using pseudocode that won't be useful if someone would implement the solutionin a predicate language (like Prolog). Given an algorithmic implementation, it is irrelevant whether the language provides foreach or repeat-until, dictionary structures etc, if short and long values are provided or not, if there is a distinction between count values (i.e. integers) and measurement values (i.e. float/real) - the implemnetation independen doc will reflect whether a value is a count or a measurement (or whatever) at a semantic level, but not as "data type".
When writing code comments and using automatic documentation tools for the formalized, directoroy style information, you can leave out descriptions of module and data structures, algorithms etc, assume that is known from general part, and focus on the implementation details.
OK, some (maybe most) methodologies pretend to take such an approach, but they succeed only partially. E.g. information modelling is often done in a way that assumes specific mechanisms, limitations etc; essentially as programming objects with a simplified syntax. E.g. you decide at a design level whether a list of names is a name array or a List<names> - even if the decision is not absolute, the tools strongly favors specific implementations. So I dislike most rigid technologies and their tools - they restrict my freedom in designing solutions.
Jacquers' task is not to choose a design tool for a new project; neverhteless I think it is relevant to approach his documentation task as if his system was designed this way, with a distinct separation between the solution at conceptual level and the way it is implemented.
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I've done quite a lot of this type of documentation in the past - my advice to you in your situation with the limited time you have is to create high level diagrams explaining how things are put together (as you have already done). Also document build and deploy procedures. I've used Visio for this in the past - but in my current job I've been using Lucidchart [^] and I would highly recommend that if you are not already a Visio "pro" 
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Lots of good ideas here, but depending on your situation, preferences and comfort level you could consider offering a different approach:
- Make an outline (mental or otherwise) of all the information you want to convey.
- Set up meeting(s) with the staff who will take over your projects.
- Present the material.
- THEY create the documentation.
- You can give the documentation a once over afterwards if you are inclined.
In addition to saving you the agony of writing documentation, the company gets the benefit of having remaining staff become familiar with your projects before you are out the door.
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Don't forget to document the environment.
Have they Imaged the development machine, is it a VM so they boot and go.
Can they even install all of the components and compile it.
Next up: 80/20 rule. 80% of the changes are caused by 20% of the system.
Think in terms of a few recent requested changes...
Next up: do you have a bug tracker tied to version control? If so, I would
consider adding contextual information to the old bugs to make clarifications.
I would RATHER you have them:
1) Know how to build/deploy the system
2) Know how to use Source Control/Bug tracker to learn from (so they keep using them BOTH)
3) Know if they have a potential issue: Document the NEVERS that many don't document...
4) The Coding Standards and Guidelines so they continue with Code Reviews!
After that, I think you can assume a professional can generate class diagrams on their own, with the tools they like (I don't usually bother), and they can spend the requisite time seeing the types of code changes made, and what requests were tied to them.
In stable systems it will be change requests. In new systems, it is usually bug fixes, or story implementation...
HTH!
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Visio (Pro) can do all the diagrams listed; and then some. You can also combine, link, publish, etc.
"(I) am amazed to see myself here rather than there ... now rather than then".
― Blaise Pascal
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My $0.02, I use Visio to document state diagrams (with a 1-1 correspondence between code and diagram in terms of states and transitions), and OneNote to document process of developing the code, leaving a trail of process and of how-to notes, documenting how to use a particular device etc.
Atle
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DocFX for documentation, WebSequenceDiagrams for your diagramming needs, bingo bango (which means you're already almost done)!
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You want to leave documentation? Just set the titles, copy-paste man pages for the contents. Nobody ever reads this junk anyway, we all know that the code (if there is a "the" code) is light years away from any existing docs.
No, that's not what I did when I left, but I could have.
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