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Advice on dealing with my boss

Not sure if it has been mentioned, but dress up nice and go to any/all services or viewings that are published publicly. You won't have to say anything but he will know.

I worked for a boss for just a short period when his son was killed in a wreck. I attended the funeral and paid my respects. It floored him that I took off of work and showed up. It sealed a very long and solid work relationship and friendship.
 
I'd write a note to him (on paper or a blank card, don't get a fucking sympathy card) and just write--> Thanks for sharing with me the other day. I have tremendous respect for you and truly appreciate all you have done for me and our team. I wish you and yours only the very best and my thoughts are with you. If I can be of help, know that I am available and happy to assist.

and sign it.

If you are 100% sure his daughter has passed, stalk his home address and send flowers and a card with "I am so sorry for your loss. Your family is in our thoughts and prayers'

thats it. He'll reach out if he is ready or needs help.
 
We had a woman in our office lose her 11 month old daughter a couple years ago. All our staff attended the funeral and supported her through a months long decline so it is different from your boss. For her, it is just following up and really meaning the "how are you and the family doing?" and sometimes letting her talk about it - till she is done - even 18 months later.

Heck, it choked me up when my business partner showed up at my grandma's funeral in a little town 2 hours away from our office during business hours.

Thank God for my wife, I just don't think about the little things that can be meaningful, she has to tell me to do them.
 
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