Here's my situation. I work as a web developer at a fairly large tourism company. Our dev department is really small though, there's me, one colleague who's on the same level as myself, and another frontend developer (who's also expected to test work that we do and write manuals) and my boss (he's one of the directors of the company and he also does development).

Because our department is so small there's pretty much nothing in terms of protocol. So when it comes to developing new stuff there's no specs or anything, we're just told more or less what the thing we're developing has to do and then when it comes to specifics we have to ask our boss what he wants and he'll then figure it out on the spot and tell us. There's also no protocol around testing, and there's also no deadlines, we just carry on until we feel it's good and then after the frontend dev tests it and confirms that it's good we make it live.

Now to the problem at hand: The three of us (myself, the other developer and the frontend dev) feel that our boss is too ambiguous when communicating to us what to do and when we end up not doing something we get in trouble because, to quote our boss,

"I can't think of everything and you should've known [what the right thing to do was]"

as if it's common sense.So my question is how can I approach him about this? What I want to tell him is that he needs to work on his communication because several of the problems that arise is his own fault. I don't want to insult him though and I don't want to just hint at it (which I've done in the past) because that doesn't get the message through.

We don't hate him and generally he is really nice and approachable. He's a really good mentor when it comes to development and technology and we're "friends" outside of work, i.e. we game together online and sometimes go for dinners and do other social things.

  • He desperately needs training in team management. If you don't have official feedback channels, ask him for a meeting to discuss how to optimize your project management. – Roland Oct 25 '17 at 10:15
  • This is a huge wall of text. Please simplify. – Mister Positive Oct 25 '17 at 11:40
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    I'm voting to close this question as off-topic because it is not readable. A simple question without such a exhaustive example would be easier to answer. – JasonJ Oct 25 '17 at 12:38
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    I've pruned a lot of out of this question, hopefully leaving the core question intact and more readable. Anyone wanting to see the full question can take a look at the revision history. – user44108 Oct 26 '17 at 7:54

Get Professional.

You are the developer, you should know what you need and how a complete spec looks like.

Treat your boss as an internal client. You should counsel what is need for you do be able to do your work. You should identify ambiguities in request and clear them up before you start developing.

If you feel you need a better testing environment and procedures, set them up.

If you need some agile planning and tool and protocol - introduce it.

If you feel you are missing resources, write a thorough e-mail to your management what you request and how and why it would benefit the company.

Stay constructive. Stay patient, one step at a time, and your can transform you team to excellence and develop yourself in the process.


Learn to communicate on your bosses level. You've been through a few already, so you should learn from them.

What sorts of questions do you need to clarify

PLAN the project before commencing, take it to the boss for approval.

Document the whole process for reference to cover yourself when told off. Politely refer to where the problem lies rather than be resentful. Just basic professionalism.


Write notes during these ad-hoc meetings and start creating at least basic requirements documents.

Get the document signed off by your boss before you commence the bulk of the work. This should protect both parties from the effects of forgotten/conflicting requirements.

Start off with at least some bullet-points per stack and work from there. Pitch this as a "trial period" thing to soften the blow and then ramp up the detail when it's proven to be a beneficial thing to do.

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