I spent most of my career as an analyst working for management in the government. I found (somewhat surprisingly) that bosses appreciate it when you give them bad news. There are several reasons:
- It gives them a chance to react and make the situation better
- They should hear it from someone who works for them rather than an outsider. They don’t want to be caught offguard.
This applies to this situation. Putin’s employees should have told him the truth. If he discourages people from giving him bad news, that’s going to harm him in the long run (which is fine with me).