Everybody needs one friend who’s allowed to ask the uncomfortable question.

Most friendships settle into agreement, which is comfortable and leaves you unchallenged in exactly the places that matter. You need at least one person with standing permission to ask the question everyone else is being polite about, and that permission has to be given in advance, because nobody takes it uninvited. The value of the friendship is in the moment it is inconvenient.

Pick that person and tell them plainly that you want the hard question asked. Then be safe to ask, since one defensive reaction usually ends the arrangement. Offer the same thing back.