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I'm a developer who has developed an idea for my current workplace that I'd like to take a lot further and take to market.

The company I work for has no interest or legal way to sell software (we've discussed this before) and I believe it to be in their best interest if I were to further develop the product. I would most certainly be sharing any future updates/revisioning with them at no charge.

Before I take the step of approaching any sort of legal advice I'd like to approach the CIO of my employer candidly and discuss this as well as find out their appetite for the idea.

My intention is to write a full business analysis of my proposal so the CIO would have a clear understanding of the features that I wish to develop. If they decided that these features are more worthwhile of an internal effort I would instead focus on that and not pursue it as an outside interest, as would be their right and expectation from me as my employer.

How should I begin this discussion and is there anything I should be prepared to answer? Is it better left alone entirely given potential legal pitfalls I'm not yet aware of? Finally, ethically is this a bad idea even though through my biased perspective I can see advantages for my employer as well?

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    Start by reading your contract and talking to HR. There may be policies already in place for this, and if so you don't want to waste the CIO's time. – keshlam Jul 29 '15 at 14:20
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    @keshlam Good point - looking into that now. Still also interested in how to proceed if there isn't anything in place already. – Michael A Jul 29 '15 at 14:25
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As Keshlam noted, you check your employment contract to ensure there are no clauses prohibiting outside professional endeavors or requiring consent prior to undertaking. Once you've verified that and additional elements like non-compete and non-disclosures, then you should spell out the scope of what you aim to do at a high-level.

Its doubtful the CIO will care about deeply technical elements of it. You are best writing a 1-2 page executive summary of what you aim to develop. Present it in a compare and contrast to clearly show how it will improve the existing process, solve a problem. Think in terms of business plan more than a technical scope document.

Once you're done with the initial document, simply express to your CIO a desire to discuss some ideas for improvement and feature releases. Depending on the nature of your employer, you should be prepared to answer questions regarding rights to intellectual property, ownership, licensing; all of the normal boilerplate items synonymous with application development. You may ultimately want to seek initial legal counsel from an intellectual property lawyer prior to even meeting with your CIO. They can point out potential conflicts of interest that aren't immediately seen at this stage.

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Don't approach him about outside work if Plan A is an internal effort. Present it as an internal project and see if he say OK. That is plan A. If he says no to plan A then ask him if it would be OK for you personally to pursue it outside the company.

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