Employ "X" has a niche skill set in my small business but is hardwired to find issues & risks with everything. He's an honest guy and means well but absolutely sucks the life out of team members. There is a problem or risk with every tiny matter we discuss and suggest and it wears me down.
I guess my question is, would you ask him to work on himself. Or would you see this style of personality as a bad fit for a very small team and look for somebody less skilled but more positive.