Anyone else here a "Boss"?

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I am not exactly self-employed, but I am technically a "small business owner" and I have "employees" of sorts who are somewhat under my command....
Sometimes this can be very difficult.
I can sometimes be heavy-handed
Sometimes I am afraid to talk to them
I am not naturally good at delegating tasks...
Anyone else in a similar position...

Working on coping mechanisms.

One coping mechanism I have is delegating an employee I am more comfortable with speaking to to get someone I am less comfortable with speaking to to do something.

Yeah, I feel for you. I used to be an Infantry Squad Leader in the USMC and I despised the role I had to take. Do you have subordinate leaders under you? If so you need to refer to them a lot and delegate tasks based on what they know about the people under them, as they will always know them better than you. Heavy-handedness is not necessarily a bad thing as long as it's in moderation, they need to know who's boss. On the flip side you also have to see things from their angle to, and be permissive. You work for them and they will work for you. Just remember what peeved you about your past bosses and try not to do the same thing. If you have a senior you report to, you'll need to keep some things from them and handle things on your level without getting them involved. handling on your own puts less on your bosses plate so they're happier and your punishment (on your employee in question) will be more lenient than your bosses so your employees are happy too. Hence the importance of subordinate leaders. To cover things for you so you don't have to find out.

One thing I was always criticized for was the fact I never got personally involved with them. I never knew when they were having family problems or just really stressed out.