Be careful about equating lobbying and electioneering.  Public charities may engage in lobbying in support of or in opposition to legislation so long as it is not a substantial portion of their activity.  (See Ready Reference Page: “Lobbying Rules Create Opportunity for Charities.”). My general position is that if a public charity is not lobbying on the conditions that affect its mission, it is probably not doing its job. But electioneering is different.  There is an absolute prohibition on electioneering, i.e. supporting or opposing a candidate for election to public office at any level of government.  A charity can lose its exempt status if it engages in electioneering.

The IRS rules do not prohibit employees of charities from supporting or opposing candidates on their own time with their own money, so long as they do not do so in official publications or at official functions of the charity.  (See Ready Reference Page: “IRS Guidance Has Not Changed on Electioneering”).  Individuals may make personal political contributions but may not use any resources of the charity, such as office phones or copy machines, in supporting or opposing a candidate.

A minister can appear at the announcement event of a candidate for office where there is no indication that the church supports the candidate, but cannot support the candidate at a church function.  A charity CEO can support a candidate in an advertisement in the local newspaper where the ad says that titles and affiliations of each individual are provided for identification purposes only, the charity does not contribute to the cost of the ad, and the ad is not an official publication of the charity. 

The rules apply to all employees of the charity, whether they are well-recognized leaders or not, and you should be sure that the rules are known by all employees.  Employees should make clear that any partisan election opinion they express is purely their own and not that of the charity.  Violation of the rules by any of them could cause your organization real grief.