I don’t think this is bad advice, but you can’t do that for everyone, not all the time. First, make sure that feedback comes in a context of trust. Say it’s a

I don’t think this is bad advice, but you can’t do that for everyone, not all the time. First, make sure that feedback comes in a context of trust. Say it’s a vendor — give it after it’s signed. They’ll likely forget your name seconds after the contract is signed. Still, that’s when you are not trying to get something from them. Because of how they are focused on sales tactic, they’ll be tempted to hear your feedback as disingenuous. Same: context is everything. Raising it in front of their boss isn’t always the best approach—especially someone as perfectionist for idiosyncratic things as sales middle-managers can be. It has to be actionable. It has to fit the rhythm of the interaction. The person has to be in a listening mood, not following a script. That’s why I recommend techniques to open all those doors: humour, especially self-deprecation, can be very instrumental to feel if someone is receptive to constructive feedback.