'Desire' was probably the wrong word to use in this context. I've written about this more in a post up-thread, and it's been discussed plenty before, so I won't rehash too much. But for me it's more about the parameters within which the organization operates, and their risk profile. There are certain things they won't do, or at least are unwilling to, certain things they prioritize which broadly center around stability and long-term competitiveness.
There are exceptions - last year Sweeney absolutely went all-in, as I've already said elsewhere, and good on him for that. But that was uncharacteristic. Had he done the same in 2019 the Cup might well have been won. For the most part there are norms and levels of risk that management generally tend to adhere to.
Which is not to say they're content merely to make playoffs. Of course not. Again, as I've already said, they want more, they want what we all want. But the ways they are willing to go about achieving that have limits. And end of the day, as far as I can tell, as long as the team's turning a profit to the desired level, the Jacobs are essentially happy.
There's nothing necessarily wrong with any of that. Any company has its methods of operating. Most of what the Bruins do is clearly quite effective. But it's open to comment and critique same as anyone else.