Recently a few folks talked about How to convince "the business folks" to let you do what you want.
While there isn't a universal and surefire way to convince your boss to let you do everything you want, below is a framework and an exercise that might increase your chances of success.
Convincing the boss is not much different than having to convince yourself.
Let's say you want to do some refactoring, here's what you can do:
- Imagine you are the boss and a stranger comes to you with this request
- Imagine what the stranger would need to tell you in order to convince you to approve that work. Their case better be comprehensive and show that they have considered it all: end-users, money, company priorities and alignment with company mission, chances of success, impact on coworkers etc.
- If the stranger manages to make a convincing case, review your notes and pitch that to your actual boss
Early in my career I ignored this and was getting frustrated and mad at people for not trusting my often valid suggestions.
The reality is that the "trust me" approach doesn't go a long way and it is crucial to make other people see the benefits and implications of what you are proposing – coming up with a strong case to convince yourself (the boss) first is highly valuable.