If you have a great idea that your boss won’t likely approve, don’t ask for permission. At least not at first. Instead do the following:
- Take a few initial steps. Act quickly with the means at hand before you ask for approval. These steps should be easy to execute and help you gather information on the idea’s viability.
- Let your boss know. Give her a heads up that you’re exploring a new opportunity in your off-hours. And then gauge her reaction.
- Make small requests. When you need resources to move your idea, ask your manager for small things that are (at least at first) within her realm of acceptable loss. With risk-averse supervisors, you need solid evidence that the idea will work before you put all your cards on the table.