Not having the right contact or level of engagement/ownership
What do you do when you have the wrong person, or persons assigned as the owners of your software? I have had this happen many times.
After the sale, the owner delegates, often to someone who had no role in the purchasing decision or real stake in its success. Being told to own it, and actually caring and wanting it to succeed are two different things.
My worst example was a VP assigned to own a deployment. On our first meeting we established that there needs to be an administrator. I asked who that would be? What? They responded, why do we have to do anything? I expect you to do that. I explained that we cannot own data management, edits/updates, additions, maintenance or onboarding. We had tools/programs to help with each, but an internal administrator would have to manage it. They had a giant fit and were very unprofessional, actually threatening a colleague. (If I go down for this, so are you!) I could tell this was going south, very south and after a few weeks went to my leadership and said this one is not salvageable and there is almost zero chance of success, as long as this person owns it. They will not renew, I told them. It was the first and only time I have done that. Months pass and I am long off this troubled account and I hear about the VP swearing at our team members. Finally someone at a very high level from our org went to the purchaser, a very senior executive, and let them know his VP is out of control and we will no longer deal with that person. We kicked the customer contact off the project! Again, never saw this before or since.
In the end they cancelled and the VP spewed toxic nonsense all over the place about the product and our team. The entire thing was money down the drain for them, a complete nightmare for us. That VP is still there, no doubt terrorizing everyone who reports to him and that he works with.
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