How do you tell your boss that they are disorganized?

You ned to figure out why you are telling them this in the first place. There’s only one good reason to tell your boss that they are disorganized. This reason is: it is interfering with your ability to peform. This will help you align your motive (better performance) and your boss’s motive (more productivity i.e. money) out of your work.

In most cases, though, you might want to be a little more sensitive about what you say. YOU are disorganized, right or not, is still an acccusation and won’t be very productive. Phrase this issue as one that “we” need to solve. Try this:

Boss, I think I could be doing a better job if we were a little more organized.

This takes the edge off and makes it a business problem not a personal problem. Once “we” can work on the problem together, you have permission to make suggestions: put things on the computer, get outside help, communicate better etc.

Your best case here is to open a dialogue where you can both create a better working environment.

Sometimes, though, it may feel like you don’t have “permission” or “room to talk” to your boss about this kind of thing.

If permission

Flatland is a great "thinking book."

is the problem – ask for permission first. Few people will deny this request. Try saying: “I want to make an observation about something happening here but I want your permission, and your promise that you will not take this obeservation personallly.”

A long request for permission, perhaps, but by asking for permission to say sometthing that can be misinterpreted, you are asking for the boss to “pay attention to the message and not the messenger.” This simple trick can let you say nearly anthing you may need to say (provided that it is not a verbal personal assault.

Use this technique sparingly though. Like the story of the boy who cried wolf, it can be overdone if misused.

In the case of not having “room to talk” you are presuming that your own lack is getting in the way of making an observation. First, no one is perfect. Second, the guidance that “those without sin cast the first stone” doesn’t hold in this context. We are not stoning people – we aren’t saying anything judgemental or disparaging. You are trying to address a gap in your current performance versus what you are capable of – if the work were a bit more organized.

Good luck, and if this doesn’t solve the problem, shoot me an email and we can try some other non-verbal techniques.