The safest avenue to go about telling your boss you like him is to do so after having built a rapport with him outside of the workplace.

Telling your boss you like him at your workplace compels him to turn you down.

A question of professionalism arises.

He isn’t comfortable talking about it at the workplace, as he believes that it is a professional environment, and he is the one that everyone is looking to for leadership.

This threatens his position and the respect of his employees.

Get him in an environment where he is comfortable and free.

An environment that is away from the workplace.

The reason why it is a good idea to build rapport with him first is in how it facilitates in getting him to see you as a unique individual, not just one of his subordinates or employees.

The goal of rapport building in this instance is to get him out of the mode of thinking that you are a subordinate.

He has to start looking at you as his equal.

The best place for him to do that is outside of the workplace, where he gets to see you in your element.

You are not his employee or subordinate outside of the workplace, you are you.

You are in your element, and his equal.

When you show him what you are capable of outside of the workplace, he gets to see more of what makes you who you are.

He gets to separate the subordinate from the person.

In essence, you become that separate individual in his eyes.

He gets to experience and note the person you are outside of work.

He begins to relate to what you love to do and your personality outside of work.

He finds similarities that make him feel a connection to you as an individual as opposed to as an employee.

Getting him in an outside environment where he gets to know you and experience your persona is highly effective.

The more he learns about you and hangs out with you, the more comfortable he becomes around you.

He no longer feels like he needs to be the boss.

He drops that sense of responsibility in being an authority figure and is himself.

This is the mindset you should get him to in order to make this have the best shot of working for you.

When he has reached the point that he is comfortable enough to be himself and let his guard down, let him know that you like him.

Having already established a rapport with him, he is inclined to give you an honest answer.

He doesn’t answer as your boss.

He answers as your friend.

This means that he tells you how he legitimately feels.

This is where you want him to be.

A boss that has built such a good amount of rapport with you that he has no qualms being open with you in terms of how he feels.