I have my Kanban workflow(Simplified) with an added column(Waiting) and a couple extra statuses in 'In Progress'.
I see the usual 'Notifications'

My Kanban Columns and Status

1) How do I let my boss know when an issue is 'Waiting' or 'Help' or a different status?
2) Which notification covers 'In Progress' and the columns?
I.E. I don't think my boss cares if something get's moved to 'To Do' or 'In Progress' but he does if it's sitting in 'Waiting.
Is there anyway to match the issues up closer to the Columns/Status?
Thank you!