Can I bring this up with my boss? Should I take it on a case by case basis and only bring it up when I need to be home for something specific. Or does being the boss entitle him to separate rules and I should remember the next time I interview for a job to ask about the work from home policy?
Yes, you can bring it up with your manager, but you need to be prepared to get an answer that you may not like and to accept it graciously. My employer allows telework on a department-by-department basis, but my department has chosen not to implement a work-from-home policy. We are only allowed to work from home during inclement weather (we only close if the New York Stock Exchange closes, and it's only closed once (Hurrican Sandy) in the last six years) or if there's a specific need, when the alternative would be having us miss an entire day (waiting for a repairman). It's frustrating that other groups in the company are allowed to work from home, because my job could easily be done remotely, but them's the breaks.
Yes, being the boss does entitle him to separate rules. "Do as I say, not as I do" implies that you believe that there is a level of hypocrisy at play here, and taking that attitude with a supervisor when there isn't can be a career-limiting move. As I posted (http://www.etiquettehell.com/smf/index.php?topic=133576.msg3151914#msg31519140
) in response to your thread about having to leave if an allegely unqualified returning employee were to be hired in "above" you, access to advancement -- and perks -- is not just a function of time at the company or time in a position. People in senior or supervisory positions are expected to have and to exercise a level of judgement greater than that of those below them. This includes being able to telework effectively.
Yes, you can certainly ask about the telework policy (and I would call it telework or telecommuting, not work from home) in a future interview if it's that important to you. Do remember that there's between asking about
it and asking for
it in an interview. A questin like "What types of work-life balance initiatives do you offer your employees?" is the way to go. Going right for what is considered by many to be a perk, not an entitlement, might lead a hiring manager to believe that you will not be happy if there is no telework policy or if the policy has to be changed in the future. Very often, people don't start out being able to telecommute; they earn that privilege based on their performance.