Question: I’ve read your blog for several months now and have found it very interesting. However, I have a situation that seems to fall through the cracks between your articles.

My husband and I moved to this medium-sized city in Illinois three years ago when he accepted an attractive job in the local school system. After settling in (finding new doctors, auto repair shops, etc.) and getting the kids in school, I found a job as the administrative assistant to the CEO of well-known local company. Though the company has fewer than 40 employees, both it and the CEO are well-known for supporting the community and have sterling reputations.

My elephant is this: The CEO went through an amicable divorce about 18 months ago. Since that time, he has engaged increasingly in sexual innuendo during our one-to-one meetings. While he’s never said anything overtly sexual, I’m becoming more and more uncomfortable in this setting. I like my job and have been told I’m very good at it. I like the people I work with, yet the situation with my boss is worsening.

Lynn, in several cases, you have suggested that employees go directly to their HR representatives when they encounter such challenging situations. In my case, there is no HR department. The CEO, as founder of the company, handles all hiring, firing, counseling, and everything else that he considers human resources, even though his knowledge of labor law is largely anecdotal. As an entrepreneur, he still retains strong operational control of the company so there is no leadership team member who can help me with the situation.

My husband has told me that I should file a sexual harassment or hostile work environment lawsuit against the CEO. My fear is that, in doing so, the issue may “go public” and be totally misunderstood by the many people in this city who respect him. I could imagine my husband losing his job and our having to move somewhere else. I feel justifiably paranoid. I have no evidence and I feel I cannot invite a third party into these traditionally one-to-one meetings with my boss. To make matters even worse, my failure to act on the situation is now causing friction between my husband and myself.

Lynn, with no one in the company I can turn to, what do you see as my alternatives?

Sincerely, Alison

Answer: The predicament you are in is not that unusual for small companies; especially ones where the current owner is the founder.

Small company CEOs are used to making all the rules and having no one to question their authority.

The first line of defense is always to ask someone to stop something the first time it happens. There is a good chance the CEO may not realize how he is being perceived and once it is pointed out, the behavior should stop.

While this may seem confrontational, it is not. If you let the behavior continue and it builds into something more significant, the confrontational scale escalates rapidly.

The more either party invests into the relationship, whether functional or dysfunctional, emotions can get in the way of having a productive conversation.

The next time something happens, you could say “____, what you just said makes me feel uncomfortable. I value our work relationship and it is important for me to be professional by keeping business and personal things separate.”

While you many not want to initiate a difficult conversation, it is the easiest and most effective option – as you will see when I describe the other alternatives.

My second suggestion is to find someone else on the management team (HR or another manager) who has influence with the CEO and confide in them about how you feel and ask them to intervene on your behalf. In your case, it appears the CEO micro-manages to the extent there is no one else to go to in the company.

Another option is to confide in someone who might be providing outside HR or legal services for the company. I would not approach outside vendors who do not have any human resources background since this conversation would need to be handled tactfully.

Absent these alternatives, you really have two choices – to seek legal recourse on your own and file a complaint or to look for another job.

If you seek legal recourse, expect that you will leave the job anyways. The work relationship will be broken.

Calling out the CEO will automatically put him on the defensive. By nature of the CEO/Administrative Assistant relationship, there must be a high degree of trust and respect for one another.

Without trust and respect, the lack of communication will become frustrating for you and your performance will suffer. There is no place in the company to transfer to avoid the “boss”.

If for some reason you think he might react positively to an outside legal action, then rethink the first line of defense – talk to him.

The other alternative is to find another job. If you are that uncomfortable with him and you do not think talking to him will change the behavior, you are probably in the wrong place.

The fact is he owns the company and there is no one that is going to fire him or tell him to leave. Ask yourself – Is this the best environment for you to be working in?

If you decide to leave, you can revisit taking legal action or just put it behind you.