How do you report a thieving boss?

My boss is stealing from the company. I have seen some documents where he inflates prices of items or makes up sales that did not happen. I have considered making an anonymous report, but I fear they will still know it was from me. -Isaac

Dear Isaac,
Progressive organisations will have some form of a whistleblowing policy, which provides a platform for such matters to be raised and then investigated. The policy provides a guideline of the process, however what is critical is that you feel confident in the process and that it will protect your anonymity. You may want to research within your organisation on whether the policy exists and its success rate, not only in addressing issues but also in protecting whistleblowers.
If there is one, review the policy and understand the process and what exactly happens once you raise an issue. If you’re organisation does not have a whistle blowing policy, you may have to conduct external research on where else you can table your concerns. If there is a union that represents the sector you work for an option is to establish whether they can help workers in such situations. Again, the issue of confidentiality and anonymity is important. In either case you’ll need to have some form of actual evidence that supports your concerns.
Whatever evidence is presented must be authenticated before an investigation is undertaken. This will protect you from allegations of pursuing your supervisor maliciously. If neither of the above are options then the fundamental question is whether you want to continue working in the organisation with a supervisor who has a questionable work ethic or if you’re prepared to leave, at which point you can leave and share the knowledge of what you know is happening.