So I have a very good relationship with the executives at our company. I am not in management, nor am I in a salaried position. The CEO (owner) loves to make his employees happy, but is a bit disconnected from the daily goings on of the hourly employees.

Now I am in an analytical role, and was chatting with the CEO, as we occasionally do, or if he has any questions. I'm looking to go to a work from home model, and passed it on to my boss, with not really much of a reaction ("We'll see"). He's a pretty easygoing guy, and although my boss has thoroughly completely, these are things the CEO has direct control of.

Being the underhanded miscreant I am, the subject came to housing (looking to buy a house, and we struck up a conversation). We began talking areas and I accidentally let slip that if we had the old office or I had the ability to work from home, it would greatly increase my home search area. He laughed and said yeah, it would.

Is dropping not-so-subtle hints about things like that frowned upon if it comes up naturally in conversation or is this a tactic commonly used to get what you're looking for in a job?

I'm not trying to go over my boss' head or anything, but I'm genuinely curious if this sort of thing is frowned upon.

  • I think the kind of interaction you're talking about is too vague and too dependent on the particular situation to give a useful answer in general. No, you shouldn't go over your boss's head to get what you want, especially if you've already raised the subject; yes, things come up in conversation sometimes. Whether you get what you want, or whether someone feels like their toes were stepped on, will depend on particulars.
    – Caleb
    May 17, 2017 at 20:45
  • @Caleb Wondering whether it's appropriate in a professional setting to drop hints like that, intentionally or unintentionally, is too broad?
    – Anoplexian
    May 17, 2017 at 21:15
  • I think so, yes. What do you mean by like that for example? Is the CEO someone who picks up on hints? Are you good at dropping hints while maintaining some deniability? Is your boss the kind of person who's likely to be offended if he finds out? Nobody is going to say Oh, yes, it's totally appropriate to suggest things to the CEO when you didn't get the answer you wanted from your boss, but at the same, depending on the people involved, you might be confident that you can get away with it without real trouble. Or not. It depends.
    – Caleb
    May 17, 2017 at 21:25
  • I'm thinking of "Inception" on this one...
    – mutt
    May 17, 2017 at 22:57
  • Would someone care to explain the downvote and how I could make this a better question?
    – Anoplexian
    May 18, 2017 at 20:11

2 Answers 2


Is dropping not-so-subtle hints about things like that frowned upon if it comes up naturally in conversation

Without context, no, it's not frowned upon. However, consider a situation where your gardner makes subtle hints when you briefly chat about how he's been.

I've been good, trying to buy a house, but it would be easier if I made more money.

What do you think about that quote? Would you offer him more money? He doesn't seem to be asking for it and you'd rather not offer if there's a chance that you don't have to. Now you're in a situation where he always does this, but you'd rather avoid a confrontation since you're not quite sure if he's asking or is just bad about sharing his personal problems.

A note about working remote

Unless the company has taken interest in allowing employees to work from home and it becomes a cultural thing the situation can turn out less than satisfactory. This is a huge topic that is more detailed in other questions. In summary, it's hard to do and sometimes things are out of your control.


My suggestion is be blunt with your manager.

I have a goal of buying a home outside the immediate area for X reasons and am wondering if remote work is a possibility. Would you consider it by doing a trial run? Perhaps WFH 2 days a week?

Working remote is a lot about you being a stellar employee, being available, reaching out to people etc, but the one thing you can't control is other people. They may choose to ask other people questions instead of you since it's "easier in person" or they just don't think of you. Having a remote culture really takes a lot of effort from everyone, not just you.

I would not mention that you went to the big boss and essentially indirectly asked him. Your immediate manager might take that as going over their head. Rather than them making a decision and choosing to involve the big boss, the big boss sort of made a decision and now your boss feels like you don't respect his position and that the big boss isn't respecting his position. Ideally the big boss would say bring it up with your boss, but that doesn't always happen.


Is dropping not-so-subtle hints about things like that frowned upon if it comes up naturally in conversation or is this a tactic commonly used to get what you're looking for in a job?

What you did was fine, and pretty smart.

Dropping hints in all the right places can occasionally get the ball rolling on lots of ideas. Unfortunately it doesn't sound like you got much reaction from the CEO. Now you need to look for other ways to advance the topic.

Perhaps HR does annual employee satisfaction surveys or discussion? If so, bring up the topic there.

You might also happen to find a time to talk to the CEO in the future. Perhaps something like "I was thinking more about that 'work from home' idea recently. That's a benefit I know I'd appreciate, and I suspect the same would be true of many others. Any chance that could happen?" might work.

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