I'm currently in a new area of the business in what is somewhat a career change (from support to development).

I have been in this position for just over a year now, and when I started my boss wanted me to read a 800 page PDF on one of the software packages/IDE/platform that we primarily use. After reading it, he wants to send me on a course then get certified on it, but won't do it until I have read it and he's 'tested' me on some concepts.

From my previous role, I had learnt a great deal about this software already just by trial and error (and challenges), so when I read this PDF/Book I am struggling so hard to retain the information. I have never been able to learn anything this way, as I mainly learn by doing and researching certain things that I get stuck on, or from an instructor lead training.

My boss has told me that I need to read this book/PDF and won't take no for an answer. There are no reasonable videos that exist anywhere for this software, which makes things drastically harder.

How do I tell him that I need help?

  • 1
    It's not clear whether you need help learning or don't want to do this. Can you please clarify?
    – A J
    Sep 13 '18 at 4:50
  • 5
    This question should be moved to SE Workplace.
    – Santiago
    Sep 13 '18 at 15:16
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    If you must learn from the PDF, try entering the important bits of information into a spaced repetition system like Anki as you go and then work through your deck every day. It really helps with remembering things in my experience, although it does require some upfront work to build the deck. (Leaving this as a comment since it's not really an IPS answer.) Sep 14 '18 at 10:43
  • 5
    I'm voting to close this question as off-topic because it should be on workplace. Boss-employee relationships are different than interpersonal.
    – Joe S
    Mar 4 '19 at 16:05
  • 2
    @JoeS Something being on-topic elsewhere isn't a reason to close.
    – Ael
    Mar 4 '19 at 16:07

I can understand your problem, talking to and convincing your boss can be a daunting task. But i see a problem

I have been in this position for just over a year now

Imagine you are the boss, and someone comes upto you after a year tells you he/she doesn't feel like one year of studying a single pdf isn't helping. He/She will need special training or hands on experience. how would you feel? Do you see a problem?.

If you had told them sometime earlier he/she might consider. But after a year, IMHO don't think trying to convince them is a good idea. I might've misunderstood this point, but if this is the case convincing them otherwise will fully depend on he/her personality and might end up harming you. Now way of going around this.Remember there is a second view, your bosses view.

Sometime as a developer, you cannot expect tutorials or video blogs to exist and your team might not have the budget to hire a trainer and classes. I some times had to work with even software help manuals due to lack of tuts or docs.

This answer might not be what you were expecting but your best bet it is to just finish the PDF. This even might be a test to see if you are worth the training and certification spends.

Just imagine you have to teach from this pdf and do a presentation, how would you prepare? do the same way. Some time learning to teach, makes you ask the right questions and helps you compress the info a lot quicker. Try getting a sandbox environment and ask you colleagues/boss for small problems you can fix or try local exercises on(the pdf might have these).

I can understand the pressure from doing a career shift and i might've misunderstood your problem completely. But the best way to prove/grow yourself is just getting stuff done, by hook or crook.


I also moved into a more specialist area of ICT after nearly 2 decades working in support, so I can understand your situation very well. Support is such a wide field that is always changing. I often found myself in situations where I was under pressure to fix something I had never seen or heard of before, and so you develop the ability to quickly learn just as much as you need to solve an immediate problem.

That skill can transfer over to something like development and be very useful. I have managed to do what it sounds like you would prefer to - that is I have learned my new job skills whilst doing the job, incrementally. For example, I started by making amendments to existing code, so I'd Google for examples of what I was trying to achieve and by comparing that with what I was already starting with I was able to learn just enough to make the needed change. One year on, and I've built up enough knowledge to write stuff from the ground up. And my boss tells me that in his opinion I'm as competent now as anyone who has been here for years and years.

The problem is, your boss doesn't seem to have the insight to see that you could potentially learn any other way than reading an 800 page document. Seriously, I don't know anyone that could read that much continuously and retain it. You can't become a car mechanic by reading a Haynes manual. You can't fly a plane just by reading a book. I guarantee that the course your boss wants to send you on will not be pure theory, no practical.

The interpersonal problem you have is that your boss "won't take no for an answer". He has put up a roadblock to communication. The only interpersonal solution he will allow you to give him is going to have to begin with a "yes". Once you have satisfied him then you're going to get sent on the course, where you can learn properly in a classroom environment with both theory and practical elements. The course is really the "help" you say you need to ask for. By the end of that, surely you will be as competent to the level he expects. So you really need to jump through this hoop for your boss, read the document, and then you will get the course you need.

To say "yes", you've read it, you really are going to have to read it! But there are many different reading strategies. If you are studying something intensely then you read carefully and this takes time. As I said previously, I don't believe anyone can learn like that. When someone intensely studies a document it is usually a document about a field they are already skilled in - for example a historian studying a history.

Instead, skim or scan the document. Get the gist of it. Try and retain the basics involved. You can legitimately say to your boss that you have read it, and if he quizzes you on it then you should be able to give some basic answers that will satisfy him.

If he asks you a very detailed technical question that you can't answer, then you could say "Sorry, it was a very long document, I don't recall that. I'm sure the training course will consolidate what I read." This may prove to him that reading in this way has limited value, and indirectly asks for the "help" you need. However, I'm fairly confident he won't ask you anything so detailed - most managers are not deeply technical themselves, and as you say he only wants to test you on "concepts". A "concept" is really a very broad idea of something. You should be able to understand the concepts of this software by skimming the documentation.

I appreciate I have made an assumption about how technical your manager may or may not be, but the fact he believes you can learn from reading alone suggests he has not learned it himself. There are countless management theories, courses and qualifications that teach people how to manage staff - but there are also numerous counter-theories that focus solely on managing computer programmers. Many people believe that the usual management strategies do not work with the personality types most prevalent among coders. You're technically minded, and you fundamentally disagree with your manager over a point which at the core is really about personality and abilities, so I can't really see that he can be all that technical.


What I would do:

  • Read the contents of the document. Cherry-pick and read the bits I think are useful/interesting, plus play with the software as much as possible.
  • Ask boss for test, expect to fail it
  • Using the questions that I failed, use them as a guide of what I have to learn (if you pay attention to what was asked, then you'll have a better idea of may get asked the 2nd time around), or if the test felt especially unfair, use it as ammo to prove I need extra help. If I passed, hey course, here I come.

There'd be no way I'd read an 800-page instruction manual either. That's a reference document. If the course is expensive, that's probably why your boss wants you to be more than ready before doing it - so the company doesn't have to pay for the test twice. So yes, I'd likely cheese the task, or refuse it.

One thing I've done for videos (my bane), is pawn it off on someone else, and have them talk about it. The trick here is to pick the right person who'd watch it and actually find it interesting and then naturally talks about it (for you this may take the form of removing snippets from the book and giving them to an interested party). Or I'm going to have to wait for a point I'm mentally ready and take notes - taking notes helps a LOT with absorption. Just reading won't necessarily help - you either need to be interacting with the thing being mentioned, or writing down a summary of what you've just consumed. And you won't remember everything - humans don't. Don't beat yourself up if you don't remember it all in one go.

If you have a topic that isn't working out for you, then there's the option of discussing it with your coworkers. You don't have to mention The Book if you think they'll grump at you for it - but you might be able to do things like "Oh, I was having issues with the debugger the other day, can you show me how that works?" or "I saw in the IDE, do you use it? Is it good?". Depending how enthusiastic the people are around you, it might be possible to get bits of their time to help you.


Try working towards the common goal, not towards using the method your boss proposed to you. The common goal is for you to prepare for the certification.

Your boss proposed reading a lenghty PDF as his preferred way of learning, but if that doesn't work for you, find your own way. Talk to your him about it and present an alternative method of learning to him that you think is more effective for you. You will probably realize that it's not at all about reading instructions or tutorials, but about learning for the certification.

A possible alternative is using any and all information available in addition to reading the PDF. You write that you primarily use this software, so install it on your computer and execute important steps mentioned in the PDF. Find a "Hello World" tutorial and work your way up to more complicated projects. Read about the problems people have with it in forums.

If there are any arguments about wasting time because you should just read, not type or click anything, you tell him honestly:

  • That you're trying very hard to learn what he wants you to learn

  • You've tried his proposed method of learning but it doesn't work for you. You think just reading alone wastes more time than hands-on practice.

  • You apply your own method of learning in order to achieve a common goal (getting the certification)

The same argumentation can be used if you don't have the software installed on your computer and need permission or the setup to install it.

Hey boss, I was reading the PDF you gave me, but I don't think its very useful to read all that without some hands-on practice. I'm afraid I'll forget too much of those information and it will take another year before I can get the certificate. Installing the software and actually executing the steps mentioned in the PDF would help me a lot to learn faster.

Keep the common goal in mind. It's not about reading a PDF, it's about you getting the certificate.

  • So your interpersonal solution to OPs problem is "ignore the other person, do what you want and when they have the valid question of why you ignore him, only give your side of the issue as a response"? What if the boss gives an actual response that isn't just "oh... ok then"?
    – DonFusili
    Sep 13 '18 at 9:20
  • @DonFusili Does my answer realy read so negative? It's true that I wouldn't tell my boss that I choose to use additional sources of knowledge to the one he offered, but that's not ignorance. I also offered arguments and a different point of view for discussions of the matter.
    – Elmy
    Sep 13 '18 at 9:31
  • To me it does, but I understand I might be misinterpreting it, my question wasn't rhetorical: I genuinely want to know if my interpretation is correct. My apologies if the comment seems like a flat-out attack of the answer.
    – DonFusili
    Sep 13 '18 at 9:39
  • @DonFusili I didn't read this as "ignore your boss and do what you want". People retain information differently. This OP seems to learn by doing, and the boss prefers reading. The goal of the boss seems to get her certified, so it makes sense to go to him and say reading a lengthy pdf probably won't achieve that goal, so let's talk about how OP can best prepare for this test. What I understood from this response is : talk with your boss on how best to solve this issue and get the certification.
    – MlleMei
    Sep 13 '18 at 10:06

Question as asked:

I would talk to your boss about what he wants the end result to be and not about the process he assumes you will take to get there.

I think that it's unlikely that your boss truly cares if you read the manual or not. What your boss almost certainly wants is for you to be highly competent with the software, and the information required to achieve that happens to be in the manual. If your boss began testing you, and you passed all of the tests he posed, do you think he would care if that knowledge came from reading the manual versus some other method?

It also seems that the certification course would have some value in, you know, teaching you the stuff in the manual. Why does he want you to be an expert on the software prior to enrolling in the course?

So if you want to talk to your boss about this, those are the sorts of questions I would ask: what do you want me to be able to do in the end? If you are unwilling to interact with the manual at all, the conversation is about having the task reassigned to someone else.

Slight frame challenge:

If your boss wants you to be competent with the software, and the only real avenue towards that is the manual ("there are no reasonable videos available..."), what other options do you imagine you have? Failing to become an expert with the software is equivalent to just not doing the job assigned to you. I don't know of a reasonable IPS answer to that.

So instead I suggest using the manual to collate information in a way that is more useful to you, not just read it and (apparently) hope to memorize it as you go. If you read and annotate the manual you can end up with things like lists of functionality, glossaries, step-by-step instructions on how to do various tasks, etc. And you have a reference document which is better for you than the manual itself. I have done this myself for dry software documentation. You could also use your notes to plan and execute learn-by-doing style activities so that you can better retain the information in your preferred mode.

So you can satisfy your boss and also accomplish what he has assigned to you by using a reading of the manual as a starting point, not as an end in itself.

This is overwhelmingly what I advise in this case. If you can't get the required expertise from anywhere else, and you won't interact with the manual at all, how can you possibly complete the task assigned to you? Then it's about having the task reassigned to someone else, or else it might be time to polish your resume and have a different conversation with your boss.


Your boss thinks that reading a long document will help you. Fact is that people learn in different ways. Some learn by reading, some learn by listening, some learn by doing. Looks like your boss learns well by reading.

So when you ask: "How do I tell him", you are suggesting a communication method that he doesn't respond to very well. Instead, make all your points, print them out, and hand him the paper. So he can read it.

  • 3
    Could you give any feedback for the last paragraph? This sounds like a very interesting technique, but I never really heard of it and can't quite get an idea of how that should make a difference. Would love to read more about the reasons why this actually could work.
    – dhein
    Mar 5 '19 at 12:49

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