There are a lot of good mental models to keep in mind as a manager when asking "what's harder than it should be?."
Bottlenecks, limiting factors, and chain link systems are two that I use frequently.
The idea of a chain link system is that the system, is only as strong as the weakest link in the chain. If you try to improve a strong link, you won't make a big impact because you're working with a complex inter-connected system. You will get the most dramatic results by focusing your energy on fixing the weakest link in the chain.
Once you identify which link in the chain isn't working well, you need to figure out what the limiting factor is. It could be a process, tool, set of beliefs, missing skills, technologies, a set of beliefs or behaviors, clarity, communication, culture etc. When you fix one bottleneck, something else will become the bottleneck.
Learning to identifying new bottlenecks and removing them as limiting factors is critical to improving the operation of teams and the business. Through this work, your team shifts from spending time on low-value activities to higher-value activities.
And one of the best ways of identifying bottlenecks is by asking "What's currently harder than it should be?"
Doing time audits with people to get a better understanding of how people and teams are spending their time is another great way to figure out if where your team spending time in low-value areas.
Everyone wants to know they are working on high-value tasks and projects. A way to get your team there is to spend the time and do the work to minimize time spent in low-value areas—this is high-value work.
The reality is that managers don't view this work as high-value. It doesn't mesh well in a world where middle managers are incredibly focused on getting work out the door quickly. It requires longer term vision and the belief that not doing this work has a longer term cost that will limit the organization and team down the road.
The problem with longer term costs is that the pain associated with them isn't felt immediately. It's not as real as missing that deadline this week. But ignoring the work needed to get you to a longer-term horizon will often delay the realization of bigger goals by years. Or worse, prevent the realization of those goals entirely—this is not an exaggeration.