Shoot Your (Carefully Aimed) Shot

A crush is a healthy thing, so try not to overthink this. At the end of the day, if you really, really like this person, why not shoot your shot? The worst he can say is that he’s not interested, which will hurt, yes, but you will handle it, and have new information about how to proceed. And if he says yes to a date, well, like I said, everything is possible. Good luck, and be good to your heart.

Blurred Boundaries

I work as tech support at a small asset management firm. As the lone support person, people come to me with all their random requests. Recently the C.E.O. stopped by and handed me an iPhone he wanted to be wiped and restored. Then he sent me a link to a spyware app he wanted installed on it without anyone being able to detect its presence. The phone wipe was successful but unfortunately it could not be activated.

I convinced him to take the phone to an Apple Store to get it activated, hoping he would forget his earlier request. Knowing his child is far too young for a cellphone, I can only assume this device is for his wife. When he returns with the phone, how should I handle this? Should I help him potentially spy on his wife, state my opposition or not install it but say that I did? He’s a petty man so I’m sure I could lose my job for refusing. But do I risk any legal actions against me?

— Henry, New York City

Your C.E.O. seems to be asking you to do something illegal. Installing spyware on someone’s phone without that person’s knowledge or permission is wiretapping. In New York, there are any number of offenses attached to installing spyware on someone’s phone without consent, including tampering with private communications, unlawfully obtaining communications information and failing to report wiretapping.

You’re being put in a terrible position here. I would tell him that you can’t install the spyware because it is considered wiretapping, which is a felony. If he wants to spy on someone, he is going to have to watch a YouTube video or something to figure out how to do it, like everyone else.

Sisterhood and Solidarity

I am a woman in a male-dominated technical field. In my industry, we frequently collaborate with academic researchers. A colleague introduced me to a professor who works at a top university and she has the background and tools to tackle a research problem we are focused on. During our meetings she suggested interesting, unique and insightful ideas.

I am excited to work with her and think she will be a great collaborator. I recently invited some colleagues to engage in this collaboration. After the first group meeting with her, two of these colleagues expressed that they did not think she was the right collaborator for this project. They said they had recently met with a different (old, white, male) professor and thought compared to him she was not as inquisitive as an academic should be. They would prefer to work with a more established professor.

The professor I want to work with is a young woman of color, which is rare in our field. The implicit bias is glaring. I have continued to express my support for working with her but I have not pointed out their bias for fear it would backfire. How can I best support this woman? While I truly enjoy my work, I face situations like this, where I see bias against myself and others, frequently enough that it can be exhausting. How do I continue to fight without burning out?

— Anonymous

The most important thing you can do is continue to be vocal in your support of this woman. When relevant, offer evidence for why she is the best person for this collaboration. And sometimes, yes, point out the implicit bias of your colleagues. They may not be receptive to having their biases pointed out, but that’s their problem, not yours. When they say they prefer to work with a “more established professor,” what they’re saying is that they prefer to work with someone they are more comfortable with, someone like them. They want to work in an echo chamber, and it would behoove you to point that out.