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I work in a small startup where my boss who starts a conversation with me as a way to making "in-between" talk (usually when he has to move away from his desk because the maid is cleaning the space), asked me a work related question and I answered it in all seriousness but when the conversation continued it feels like all he wants to hear is a "yes it can be done" than mule over the nuances of what it entails. I am in a technical role so I give an answer based on my previous technical experience.

To make light small talk I sometimes talk about non-work related things and even if I am saying something, he acts like he didn't hear anything, basically checks out of the conversation so it feels like I am only "forcefully" talking but nobody is listening.

Once in awhile this is fine because I know not all of what one says is of any use to another person but repeatedly trailing off a conversation tells me as if he is not interested in holding a conversation after he feels like his itch to make small talk has been satisfied and that I should just shutup after it.

How do I deal with this kind of conversation where I feel cut off despite being asked for my opinion?

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Some bosses are interested in the technical details of a solution. Most aren't. One of the skills you'll want to pick up as a technical person is the skill of reducing your arguments to the minimum of information required to make an informed decision. Your boss doesn't understand the technical details, so he checks out of the conversation when he gets lost. If you can instead do something like the following fictive example:

As I see it, we have two options. One option is to use an Oracle database but there will be licensing costs involved and it's more complex so it is likely to take longer to develop with. The other option is to use MySQL but that has technical limitations that might cause issues at a future point in time.

By boiling things down to their essence, you're giving your boss enough information to make an informed choice but you're not overloading him with things he won't understand anyway. This also helps you steer your boss towards your preferred choice, as you will usually have a reason for preferring that choice which you can mention.

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    Thanks! I kept my technical jargon to minimum and only limited myself to plain English to describe features and he seemed to listen. Off work conversation I don't bother because I don't think he's into that. – anklebiter May 6 '15 at 10:24
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Is your boss a technical person? If not, it is likely that he is checking out if you are giving him technical answers to his questions. Non-technical people generally do just want a 'yes or no' answer rather than the nuances, as the nuances are not their job and probably not something they understand as well as you do. In situations like that, you need to learn to tailor your answer to the person who asked, rather than just giving all the facts all the time.

When it comes to small talk, it is difficult to answer without knowing you in person. How much do you make it a conversation? Are you asking questions as well as talking? If you are just giving a monologue that is probably too much, and more than people expect from small talk. It should be just a few sentences e.g. "How was your weekend?" -> "Oh we took the dog out, saw that new Avengers film, how was yours?"

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I have had plenty of bosses who just walk out on me the minute I give them the answer I want. That's fine by me because I need the rest of the day to get done the things I need to get done. If they suddenly decide that they more questions or need further qualifications, they'll hone in on me again.

I had one boss who so forgot himself that I yelled at him through the door: "Steve, I am in the bathroom! I'll be out in five minutes and we'll take care of this. Leave me alone!" :)

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