My company has been growing steadily over the past few years. We have been fortunate enough to take on more employees to. Last year, I took on a colleague of mine from a previous company I worked at (I always did my own thing on the side but only decided to fully commit to it start of last year). I feel that this person has, since the start of his employment, been trying to make strides to secure ownership of the company (shares). Although I have never really said no to his requests, I have also not explicitly said yes. The feeling I am getting is that he has an expectations that he should get shares for taking the risk to start working at my company, which at that stage was a lot smaller then it is now. I do not have a problem to give shares to deserving employees who turn out to be worthy partners, but I feel that simply dishing out shares, even if a minority percentage, is not something one should consider lightly. Recently, I was also disappointed by the person in question's handling of business meetings while I was on leave. Some clients phoned me to describe the meetings as downright awful and pathetic. This further causes concern. I am not entirely sure how to handle the situation and how to approach the conversation. The person has already gone to great lengths to set up business trusts in which he intended to hold shares in the company, so a part of me really feels bad. He also has a family to provide for, but the same is true on my side and my business is my sole income and pride and joy. My main worry is that I can be made out to be dishonest or untrustworthy for only having the difficult conversation with him now, but on the other hand, I need to make calls that I am comfortable with and which brings the most amount of reward my way (and I do not mean that badly, but that is why I started my own company and have grown it as much as I have instead of working to enrich someone else). Any advise or comments would be greatly appreciated.