I have been at my company for over 3 years now and I see a very concerning pattern of people constantly over promising things and under delivering.
To give a little context, I work for a Saas company that provides critical business applications to clients. We are very sales focused and tend to make promises to larger prospects to win the business even if it means we have to build something custom for them. This in and of itself presents problems for a cloud based solution that hosts thousands of clients. It is not common that we will add little features here and there to satisfy a single clients needs adding complexity and extra configuration for customers.
I work as a product manager so I see this functional debt being added over time and what it does to the application. Often times when management promises things to clients it turns into us custom developing a solution to meet their exact needs. In some cases the customer quits because we promise to get them up and running on the solution by x date, without understanding the timeline of the feature development. In most cases we develop a specific feature and then they refuse to start using the software until other needs are met.
I have seen us waste hundreds of thousands of dollars trying to get large customers to use our software. It's extremely frustrating to me seeing it happen over and over again. It's at the point where people ask me if we can do something for a customer and I say no, but they end up selling the deal anyway.
I sometimes wonder if no one else learns from these mistakes. It seems like the upper management team does not. It's literally the definition of insanity in my mind. Doing the same thing over and over but expecting different results.
Does anyone else deal with this at their company or have any advice for how to deal with it?