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How do you ask a former star employee to leave?
“Your question on "How to?" seems a little more in-depth than just a superficial question to a performance related situation.
You mention - - this person is emotionally attached to the company
- Why / How ? - is this person a former partner who is not happy with a new direction the organization may be going?
- Was this person promised / awarded with high rewards compared to initial baseline
expectations than what the company initially had? Now that that the business is maturing the expectations are different? So a change in star status????
- Since yours may still be a fledgling organization you may not have a formal HR setup and everyone maybe viewing themselves as having potential ownership of the company, though in reality there may be only one or two real owners.
- No matter where you are or what you do a - 'friend' is never perceived as a - 'boss' or 'mentor', so don't try to become a 'boss' now after being a 'friend'. You will usually be ignored at best and / or be viewed with antagonism and being arrogant otherwise.
My suggestion is to have a peer of your's have a formal heart to heart talk with this associate and plant a seed of separation on either a voluntary or involuntary basis. Sometimes even the office grapevine has it's uses in resolving such issues. This way if and when you finally discuss the separation issue directly it will not come as a surprise to this individual as then it would be viewed as inevitable since others in the work place knew of it also.
Lastly, I can't imagine having dead weight around as you imply is good for the company bottom-line, so also mention that the organization's finances cannot support operational inefficiencies therefore separation would be the most mutually beneficial option. Keep the discussion focussed on the organizational needs and expectations, do not delve into personal issues, habits, or behaviour as this would be counter-productive.
Be firm, but compassionate. Offer a personal recommendation to assist with new endevours if the person requests and keep it brief and business oriented. Hopefully, your friendship will survive this incident."
