I would point to a few things.
There is really not very good life-cycle planning when it comes to military procurement. The gaps the country is potentially facing didn't sneak up on Canada; you knew that there would be a useful life to a ship or an airplane. Planning ahead for that needs to be done better.
I would then point to the complexity of the procurement processes. It isn't just about buying a good anymore. Many of the procurements are trying to accomplish many things, whether they are about creating an industry, as in the shipbuilding case, or trying to have economic benefits come out of procurement. There is a trade-off when you try to accomplish many things in a procurement.
Finally, I would point to not really having a stable outcome. What should the Canadian Armed Forces look like and what does it need? There needs to be better consensus about that across the government.