There is an issue I am seeing that is causing a problem with shared time in fastly growing IT department along with business matters and the CEO trying to oversee all of it. Ultimately, what once were status checks that can include full detailed information and explanation on a particular project and where it stands, now must be very simple magic bullet points that do nothing but cause wrong assumptions and misunderstanding leading to false and unrealistic expectations. Critical decisions can't be made just by bullet points. The business is growing to a point where the CEO needs to offload the IT portion to a CTO who has a much larger area of responsibility than a department manager reporting direct to the CEO can do.
Anyone ever been through this? How were you able to convince the CEO (who can't otherwise see this problem) they need to hire a CTO? Did some tragedy have to happen first? Lost large client, business, etc?