We are a 30-agent real estate brokerage company with one administrative assistant, our lone employee. However, her professional abilities have not kept pace with the times. She has no technical skills and can’t keep up with her other tasks. She is 75 years old and we are at a loss regarding how to handle easing her into retirement.

Is after-hours employee fraternization between a co-founder and an intern inappropriate, or am I just being extra cautious?

A client recently threatened to quit working with us after seeing politically-charged posts she deemed offensive on one of my account manager’s social media accounts. I’ve asked the employee not to let this happen again, but he countered that we have no policy in place (which is true), and furthermore, these are his personal accounts and he is entitled to free speech. How can I deal with this situation?

I interviewed a job candidate who was severely overweight and had trouble walking. While the job is mostly a desk job (administrative assistant) the admins are expected to run things back and forth when needed. Could I have asked her about her health? I didn’t. I didn’t offer her the job, either, and now I’m feeling guilty. What should I have done?

We drug test new hires at my company. When a potential employee’s test comes back positive it’s easy enough to rescind the offer, but we had a candidate have a test returned “negative but diluted” and we rescinded the offer. The candidate had already given two weeks’ notice at his current company and they won’t take him back. Did we do the right thing?

I have an employee who hasn’t been performing well. Last week, she was out sick again and I needed a report. I tried to call her, but she didn’t answer. So, I asked IT if I could get the report from her email, and they gave me access to her inbox. I found the report, but curiosity overcame me, and I opened a few other emails. I feel totally guilty — I snooped. Is this legal? Is it moral? What do I do with this information?

My assistant “Jane” has a reduced work week, from 8:30 a.m. to 3:30 p.m. I agreed to this when she was hired. However, two years later, I now need her to work more hours. I don’t need or want to hire an additional person — I just need her to work an 8-hour day. But she doesn’t want to. What can I legally do?

I recently made an offer to a new director of communications for my company. However, I then found out this individual had posted to Facebook asking friends for feedback on two job offers — one for my company and another for a local competitor. I was horrified and I want to remove my offer. Any advice on how to tactfully prevent this from happening in the future?

We have a female employee who reported sexual harassment from a male coworker. The woman didn’t want to come forward, but once the CEO found out, he felt he had an obligation to handle the claim. We currently are without an HR manager. What is the proper way to handle this? Should an investigation be made? 

I recently received a promotion, so two months ago I hired “Jane” to assume the role of my former position. Since she’s been here, Jane has constantly undermined me. She has told lies about my character and my productivity to other employees. It is quite obvious that she intends to do whatever she can to show that I am not fit for my new role. What is the best way for me to document her behavior?