It's hard to do the right thing

There's a trap in running a Salesforce program that's three, four, five years old. You can be extremely busy and still be doing the wrong thing.

Building new features is easy. A Sales rep wants a new field on Opportunity, a manager wants a new Report, support wants a new automation. You say yes, you build it, everyone's happy, the backlog moves. It feels like progress because it looks like progress.

Cleaning up is hard. Try removing a field nobody's used in two years and watch what happens. Someone finds a Report that references it. Someone remembers "we might need that for Q4." Someone who hasn't opened that Object in eight months suddenly has a strong opinion about it. Simplifying a Flow that's grown three layers of nested logic means untangling decisions made by people who left the company. Rewriting a screwed-up screen flow means admitting the original one was wrong, and someone built that one too.

This is the actual signal. If a piece of work is easy to get agreement on, it's probably additive, and addition is rarely the problem in a mature Org. If a piece of work makes people defensive, slows down a meeting, or gets quietly deprioritized three sprints in a row, that's usually where the real value is sitting.

Doing the right thing in an old Org is almost always the harder conversation, not the harder ticket. The technical work of removing a field takes ten minutes. Getting permission to remove it takes months, because it means confronting ownership, habits, and a little bit of ego.

You can judge your roadmap by this test. Look at what's easy to greenlight and what's hard to greenlight. The hard ones are usually the ones that matter most.