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I have been working here for several months, and he usually looks so chill and funny, empathic. Lately he still likes to joke, but the smile quickly fades off and I can see despair in his eyes. This has happened on the last couple of days.

The business seems to be going well, we hired five people since me. My best guess is that he's sick and depressed, but it could be anything.

I want to tell him that I'm worried about him, and casually ask if he's feeling Ok. He's the CTO and I'm a junior developer. Recently the company had a party celebrating an achievement and the two of us chatted; that was when I noticed that something changed. He's been down since then.

So the problem could be some unrealistic expectations about that achievement (could get there earlier, could get 1st place instead of 2nd). Or the party itself (coworkers could be more woke and at least bring some interesting ideas).

Would attempting to talk to him be appropriate? Or this is guaranteed to be awkward for both of us?

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Based on what you describe, I doubt that he is behaving that way because of your performance or the achievement obtained; this seems more like a personal situation he might be facing.

There is nothing wrong in worrying for you colleague's state of mind or mood (even if they are superiors); in fact, perhaps he is having trouble dealing with it and perhaps a chat and showing some support is just what he needs.

So, I suggest that if you plan on talking to him do it privately, and try phrase it something like this (as to avoid any awkwardness but still show support and empathy):

Hello boss... [casual intro chat] ... Now, if I may, I also want to talk about something personal with you. I have always known you to be a cheerful and positive boss and I admire those traits. Lately I have noticed that those things have changed a bit, and that made me worry.

Now, I know that perhaps it is something personal and I understand if you prefer not to discuss it, but be reassured that you can count on me whenever you feel like talking to someone; I'll be glad to hear you out and hopefully help that cheerful boss we all admire.

Optionally, if you feel this is still to direct/awkward, consider making it more discrete and "smooth" by briefly updating him on your tasks on the [casual intro chat] part. Or, as PagMax suggested in comments, cut the last part if you consider it too personal or out of place to say in your context.

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    Thank you, the message is golden. Need to figure out the phrasing (nobody talks this formal at our office), that's going to take a while. Will upvote asap. – Саша Давиденко Feb 14 '18 at 1:08
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    I don't know the OPs and boss's age and the cultural background and I think that is important. I am sure in some countries a junior developer could talk like this to the boos. But I am also sure in other countries and especially if there is some age difference that would not be appropriate. Some bosses might think that you only play the nice guy and you hope for a better personal relationship i.e. to get later more money. I don't think you think like that but you should consider that your boss might get that impression. Be careful that the boss does not misinterpret what you want. – Edgar Feb 14 '18 at 2:07
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    @DarkCygnus: I know some people who would interpret such behavior as "sucking up to the boss" - even if it is well intended. I think the OP and other people who might consider something similar should be aware of this possibility, even if it might be remote. – Edgar Feb 14 '18 at 3:26
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    @Edgar shame those people have such mindset, perhaps they have been through negative experiences. I agree that care is needed to not come out as sucking up, but given this is a special and unfrequent incident that possibility is more unlikely. – DarkCygnus Feb 14 '18 at 3:29
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    While I agree with most of the answer, I agree with @Edgar as well that depending on age and hierarchy difference, this will be awkward and misinterpreted. I would just leave at first paragraph and not include the second one at all. More like "You have always been so jovial but lately I see you rather serious. Is it work? Is everything alright?" or some variation if it. – PagMax Feb 14 '18 at 4:54
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Generally a change like this means something very bad is going on in his personal life. Someone close to him may have died or been diagnosed with a serious disease, he might be going through a divorce or he might have been diagnosed with something. I bring up these things because that is the level of thing you may have to deal with if you choose to talk to him and he decides to confide. So be aware that you might be opening a can of worms you don't want to get into or are not prepared to handle if you ask about it.

I personally have asked coworkers about something that seems to be upsetting them and have had to help them get through a child with cancer, a spouse with cancer, a terminal diagnosis for themselves (she died about 8 months later and I was one of only four people at the office who knew of her disease and the only one who knew it was terminal.) and a very messy divorce. You take a real risk when you ask about this type of sadness that you will get more than you wanted to deal with. I have been through many of these types of things myself being widowed and having a great niece with cancer, etc. So I am prepared to deal with whatever a person might bring up. If you are not (as I was not in my twenties), it may be best to stay quiet and simply try to make sure that you don't add to this person's stress by creating work issues for them.

Generally when I see symptoms like this, I usually make sure that we are in a private place and say something along the lines of, "Are you OK? You seems very sad. Is there anything I can do to help?"

Now this accomplishes two things. First, it lets him know that people are noticing which he might not want if he doesn't want to tell and he can then be more careful about his behavior.

Next it lets him know that you are willing to help which can be important when someone is in a personal mess.

However, if he hasn't made a general announcement of a problem, he will likely say he is fine. That's ok, we don't owe a coworker a description of our personal problems. That doesn't mean it was wrong to ask if he was OK, even when they don't want to tell you the problem, people like to know others are concerned for them.

Just be aware that OK doesn't necessarily really mean OK. Look for ways you can relieve work stress on him if he continues to look sad. Sometimes the best way you can help is by not creating more stress. And don't continue to ask.

If he chooses to talk or breaks down, be prepared to handle that and understand that in general this type of conversation is confidential. Don't blab about it to others in the office. If he chooses to talk that is a big sign of being trusted. Be worthy of that trust.

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    It helps a lot when someone asks "Are you OK?" Even if they just say "I'm OK" back. So don't worry that you've not helped if that's what happens. – user74616 Mar 16 '18 at 17:55
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Be very careful about making a diagnosis of anyone - even if you think you see "despair in their eyes" - unless you have qualifications in mental health. Certainly don't try to ascribe a reason - as has been said by others, it's more likely something happening in theirs personal life than at the office. It's also possible nothing specific at all, depending on the person.

That said - there is nothing wrong with reacting with some concern. Here in Australia, we've been promoting a campaign called RUOK? for some time - sometimes just asking threes question helps. If you don't think you can be direct, you could try "how's things?", or "are things okay for you at the moment?"

I agree with others not to discuss this with anyone elder at work, though.

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