Any concerns is the most-asked question in professional life and it returns nothing, reliably, in every organization.
Not because people have no concerns. Because answering requires them to volunteer that something is wrong, decide it is important enough to raise, and accept whatever follows from having raised it. The question makes the person do all the work and carry all the risk, and no is the path of least resistance in every case.
The principle
A good question is one whose easiest honest answer is informative.
That is the whole design criterion. If the least effortful truthful response is nothing, the question has failed regardless of how sincerely it was meant. If answering honestly requires courage, the question has been aimed at the wrong people, since only the confident will use it.
Six that work
What would have to go wrong for this to fail? Presupposes that something could, so naming a risk is answering the question rather than raising an objection. This is the most useful single question available to a leader.
What is the part you are least sure about? Assumes uncertainty exists, which every plan contains, so admitting to some is compliance rather than weakness.
If this were entirely yours, what would you do differently? Removes the person from having to criticise a decision and invites them to describe an alternative instead.
What is the earliest date this could finish, and the latest if the things you are worried about happen? A range rather than a number, and the second half grants explicit permission to describe the worry.
Who would disagree with this, and what would they say? Lets a person voice an objection they hold without owning it. Frequently the objection they attribute to somebody else is their own.
What am I not asking about? The most valuable and least used. It concedes that your framing may be wrong, which is the thing nobody will tell you unprompted.
Questions that survey rather than probe
Several common questions collect a verdict when what was needed was information, and the verdict is nearly always favourable.
Does that make sense produces yes, since no is an admission of not following. How is the project going produces fine, because a fuller answer requires deciding which parts you want. Are you comfortable with that produces comfort, since discomfort would need justifying.
Each is answerable in one word and each of those words is uninformative. The repair is to ask for something specific: what is the first thing you will do, what is the part that will take longest, what would you need in order to be comfortable.
The leading question you did not notice
Questions frequently contain the answer, and a person with less power will take the offer.
You are happy with the timeline, right? Do you think we should go ahead? We are still on track, aren’t we? Each of these names a preferred response, and disagreeing now requires contradicting a stated expectation rather than simply reporting.
The tell is a question you could answer yourself before it is asked. If you could, so can they, and they will.
Second questions
The first answer is nearly always the prepared one. Almost all of the value sits in the second exchange, and most leaders never reach it.
What makes you say that. What would change your mind. Say more about that part. Each is short, each signals that the first answer was heard rather than merely received, and each frequently produces the version the person had not planned to give.
Moving briskly to the next agenda item after a first answer teaches the room that answers are collected rather than used, and subsequent answers get shorter accordingly.
The question is not the whole system
Good questions asked by somebody who reacts badly to the answers stop working within about two rounds.
The person who names a risk in response to what would have to go wrong is testing whether the invitation was genuine. If naming it produces visible displeasure, ownership of the problem, or a reference to it three weeks later, the question has been answered honestly once and will not be again.
Which means the phrasing in this entry is worth perhaps a third of the outcome. The remainder is what happened the last time somebody told you the truth, and everybody in the organization already knows what that was.
Edited by Patrick J. Wolf, PhD