I am new to my job and my boss constantly talks in suggestions like “you can achieve so much here,” but sometimes this familiarity continues outside of work, for example, they send me messages. Should I ask directly, or should I pretend to misunderstand? I don’t want to lose my job.
The same thing happened to me, I also had those motivational phrases like “you can achieve a lot.” But then they started sending too many personal messages, and eventually their intentions became clear. I suggest keeping some distance before asking directly.
Things like this happen quite often at work. Maybe they are trying to boost your motivation for your job, which is why they may come off as overly familiar. If it’s work-related, there’s no issue, but be cautious with personal messages.
I’ve noticed something here, sorry but do you reply to your messages outside of work? I think you should also know how to establish your boundaries a bit. People sometimes don’t realize how they are perceived; it can backfire.
It’s important for the boundaries in patron-employee relationships to be clear. If there is any discomfort, direct communication rather than indirect is always healthier. However, if there is a risk, it may be safe to share it with an HR representative.
Let me add a detail, he has always talked about work-related topics in his messages, but his way of speaking outside of work is much more relaxed. It’s like he’s right on the edge.
Let me be frank, these kinds of things always cause problems. Work should stay work. If you feel any doubt, just step back right away. Otherwise, people will talk, and you won’t be able to defend yourself 
In this type of communication, you set the boundary. If there is a familiarity that goes beyond work, you need to be very clear about it. It is unacceptable for someone to overstep your boundaries without your consent while using their power position; if necessary, escalate the situation to the authorities.