The current customer base is not representative of what the business wants to be in the future.
There seems to be a lack of acceptance that current clients are only concerned with getting the cheapest service possible, and are not interested in improving their businesses by investing in technology.
Technology being supported is non-standard, dated and unsuitable for the job - leading to problems that cannot be accurately diagnosed or fixed remotely.
A recent office move was extremely badly managed, and led to a massive number of employees leaving at the same time, with no plan to replace them.