Should I tell my boss what I think of his business ideas?

Can you think of a positive way to tell him what would work better?

Send him this?

Offer him solutions not just criticisms. So, very diplomatically explain how you think his idea could be improved and why you think his original plan might cause problems. Definitely don’t start off with “I think you are wrong” or similar.

You’re correct that it’s not your place to interfere or give unsolicited advice. It would be nice if he would ask for input. In that case, you would be justified to give him your views from the vantage point of dealing with his customers all the time.

But, your boss might have reasons for his plans that you know nothing about. Better to wait to be asked.

If you have a good working relationship with your boss, I do not see any problem telling him about your concerns. You could tell him that you were thinking about his planned changes and have a few questions. You could pose your concerns as “what if’s” and ask if he thinks they are likely and, if so, how he would be able to handle them. Do not, under any circumstances, make any derogatory remarks about your boss’s ideas.

I do not think it is not your place to give advice. On the contrary, I think you should, because it is as much your company as it is his (but I am egalitarian like that). Sometimes bosses need to be called on their bullshit.

I sort of agree with others in this thread (including @ragingloli, but maybe not to that degree) that it is certainly your place to voice concerns about how changing policies will affect the people you deal with. But how you do that is vital.

As @Bellatrix says, don’t just criticize and “bring problems”, but attempt to understand why the new changes are being made (“cost savings” is always an obvious and reasonable concern, as well as “reduce processing time” and other direct and indirect ways to improve profitability, marketability, sales, etc. – even employee turnover) and recommend a resolution to the problem that you predict. Many times managers don’t think far outside of the particular issue they’re looking at, which can lead to effects opposite to what is intended.

So if you think you know something that’s being overlooked, then by all means ask, “Have you considered the effect of this change on [whatever]? Can we include [something else] in your proposal, so that those effects will be mitigated?”

Use @CWOTUS‘s excellent suggest of asking questions. People feel much more compelled to answer questions than declaratory statements.

It is a wonderful technique for any sort of confrontation and often gets a teen-ager with lock jaw to say a few words more than usual.

If I were your boss I would want to hear your concerns, and would think more highly of you for having the courage to speak up and voice opposition (even if you’re ultimately wrong about how it would effect the bottom line). Unfortunately not all bosses are as amazing as I am, so that approach could be hit/miss. I would be sure to focus on how it would effect the company, and your customer’s relationships and remove the personal aspect from the decision (i.e. “the” idea instead of “your” idea).