My non-technical manager just paid for a license to use a tool which designed to pick mentions of your brand name at blogs, "social media", comments, etc. and gauge the sentiment (positive, neutral, negative) of the post. What he wants me to do is use it to do a task which can only be achieved with a certain level of natural language processing and hence shows up unrelated results for whatever query you can try.

I want to be able to explain to him that this tool is designed for task X and what we are trying to do is task Y. Y cannot be modelled as X. And all the success of the tool he cites as proof is proof of X which is not Y.

4 Answers 4


Simply send an e-mail to the tech support of the product: "How should I do task Y using your tool?"

Maybe you'll be surprised, maybe your manager...


First of all, be cautious when explaining him that the tool he choose isn't apt. Your intentions, however good they may be, they may be perceived as a way for you to evade doing the task or even worse - you can make him feel stupid (and you don't want that).

As you explained here - the tool isn't capable of doing such things. Explain to him in plain language what are the intended use cases for this tool and which results are possible with this tool.

Also, you can find out about other ways (tools) to accomplish the task and discuss it with him. Prepare good for his questions so that he can see that you know what you're talking about.

If he's still not convinced try another approach. Calculate the time you will need to spend doing task (if you even succeed) with the tool X and time that will take you using tool Y. If the time benefits of using the tool Y are great (time == money) he can choose the other tool.


User christian.p had some excellent suggestions which I will recap:

  • Don't make him feel stupid: This will illicit irrational emotional based responses.

  • Look for other tools that perform Task Y: This shows that you genuinely wish to help him solve the problem by offerring alternatives.

  • Provide quote for custom development of Y feature: This shows you aren't lazy and gives him the impression that you aren't brushing him off.

What I would like to add is that you should try to see this through the management perspective. I am sure it doesn't surprise you that there are a LOT of worthless software developers and IT professionals in the field, and your manager has probably been around the block enough times that he had the misfortune of managing a number of such individuals.

Managers get told "Y is impossible" by supposed "professionals" all the time that are either tragically misinformed, blatantly untrue, or scandalously deceitful. Many of them figure this out later talking to a more qualified technical person or figure these things out years later after said person had already left the company and the new guy rolls in and actually does the imaginative impossible.

Where I work now my manager had a number of myths about the capabilities of the technology platform we are working under, fed by the previous development team (and if the abysmal quality of their code speaks to their skill level then it is not flattering). I prototyped and implemented a number of game changing things on top of meeting deadlines and goals and now my manager trusts me.

Earning your managers trust is the only way to actually avoid the annoying leg work of proving your assertions. Now that I have his trust I can tell him that something is "an extreme challenge" (I NEVER use the word impossible to describe anything), and he takes my word for it.

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    But it is stupid to buy a tool, without consulting experts before. A good manager never trusts a sales person blindly.
    – Ingo
    Oct 12, 2011 at 14:36
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    @Ingo And is it smart to tell your boss that he's stupid? Oct 12, 2011 at 14:49
  • @Ingo Agreed, but I don't always think it is wise to call a spade a spade just because its true. Being in the business world is a lot like being married. There are some things you just don't say or even discuss no matter how true.
    – maple_shaft
    Oct 12, 2011 at 15:18
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    @maple_shaft I guess this depends on many circumstances, from unemployment rate to your personal standing - in germany, currently, you'd not hesitate to complain. This can be done in a cooperative way, i.e. from face to face without someone else listening: It is your responsibility to enable us to make a good job, hence, please don't buy tools for use by people without asking them for their opinion first. (Or else I tell upper management how you waste money.)
    – Ingo
    Oct 12, 2011 at 15:28

Take the desired task that you expect the tool to handle and create some use cases. Show your manager that the tool fails to produce the desired output of those cases. Explain that the modification can't be done for reasons such as the tool has no potential for hooks, the tool vendor is not providing documentation to do that, etc.

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