I work in a company that's extremely chaotic and absolutely not modern in terms of IT technologies and processes.
I worked in 5+ companies before but haven't experienced anything like that before. Basically, it's a major disaster and the causes are clear, although I wouldn't like to go into them now.
Now I have a new employee. When recruiting him I did signal what the situation is. I also asked him situational questions ("What would you do if ...") to find out what his reaction to the situation would be.
Now he is onboard and I see he is getting more and more shocked and frustrated with what he's got to work with. I understand this frustration since my reaction was exactly the same. Actually he's asking the same questions I asked after I started. I make it clear to him that I understand what he's frustrated about but also that it's a long way to change it - I don't want to lie.
Apart from that, he is very good, picking up things quickly. I'm happy with his performance.
At the same time, I have reasons to think he might be looking for a new job because of his frustration. Realistically speaking he would get similar money (probably 5-10% less, but that's not a huge difference) but have a much easier job at another company.
What can I do to make him stay? A salary increase isn't an option. I try to stress the potential to learn and transform things in the current setting, but I'm not sure that's convincing. Our relationship is good and I don't expect him to do unpaid overtime.
Why I want him to stay: I've had several people quit quoting the issues mentioned here or unable to work in these conditions. I can't afford to have another one.