[imbnwa]

The real issue in a situation like this is the use of the Agile Story point BS to create competition between developers in order to have leverage exactly this to push back against the Engineering team with. You need to have a Dev-only meeting so Bob doesn't feel specifically called out and talk about how you all want to negotiate the interests of Product/Business with the dwindling engineering situation, i.e. Tech Debt.

Bob, and others like Bob who live to impress management with their personal 'agility', will implicitly feel more pressure to not go against the whole engineering team if you're able to reach even near-unanimity about what that strategy will look like, in this case, perhaps coming to agreement about how certain tasks will be pointed univocally, amongst other possible strategies. Your only obstacle at this point is a head of Engineering whose interested in their own career over and above his team.

Agile SCRUM exists, largely and for the most part in my experience, as an abuse to prevent this kind of 'collective bartering' on the part of Engineering.