Leadership ethics questions to ask your team, before approving, and upward

The questions a leader asks themselves are covered elsewhere on this site. These are the ones to ask other people: the team, in the ordinary run of conversation; a person about to sign something off; and your own manager, when you have been asked to do something and are not sure.

Each comes with what a reassuring answer sounds like, what a worrying one sounds like, and the follow-up that separates the two. The examples are hypothetical.

What to take away

Questions for a one-to-one

Ask these routinely, in the same tone as anything else, so that they carry no signal when you ask them of a particular person.

"What is the thing you are most worried about that nobody has asked you?"

Reassuring: a specific worry, quickly named. Worrying: "nothing really", from someone whose area has visible problems. Follow-up: "What would I be worried about if I did your job for a week?" People will describe in the third person what they will not report in the first.

"What did you do this month that you would not want described in a meeting?"

Reassuring: something small and honestly told: a shortcut, a rushed piece of work, a conversation handled badly. Worrying: nothing, ever, from anyone. Follow-up: "What does the team do that fits that description?" Teams are more candid about the group than about the self.

"Who on the team would you go to if you saw something serious, and would you actually go?"

Reassuring: a name, and a yes with a reason. Worrying: your name, offered quickly, from someone who has never brought you anything. Follow-up: "What would stop you?" The answer is the list of things you need to fix, and it usually includes something about what happened to someone else.

"What is the customer we treat worst, and why?"

Reassuring: a specific account and a reason that sounds like a trade-off rather than an accident. Worrying: "we treat everyone the same". That is never true and is the answer of someone who has not looked.

What is owed to that customer is covered in customer ethics. The question here asks whether your team knows who it is.

Questions before a sign-off

Someone brings you a decision to approve: a deal, a hire, a change to how something is done. These questions take five minutes and are the difference between approving and rubber-stamping. The distinction between a program that reviews decisions and one that records them is the same one drawn in the Department of Justice's compliance program guidance.

"What would have to be true for this to be the wrong call?"

Reassuring: a clear condition, and evidence that they checked it. Worrying: "I can't think of anything" or "it's pretty straightforward". Follow-up: "Who argued against it?" If nobody did, ask who should have.

"Who is worse off if this goes to plan?"

Reassuring: a named party and an honest account of their cost. Worrying: "nobody, it's a win-win". Follow-up: "Have they been told?" If the cost is real and the party has not been told, the sign-off waits until they have.

"Which rule does this come closest to?"

Reassuring: they name the rule and say why this is on the right side of it. Worrying: "it doesn't really touch any rules". Every decision worth a sign-off comes close to something. Follow-up: "If it were on the wrong side, what would it look like?" The person who can describe the breach can be trusted to have avoided it.

"What are you not telling me because you think I won't like it?"

Ask this with a straight face. Reassuring: a pause, then something. Worrying: an immediate "nothing". Follow-up: none needed; the pause was the answer.

Questions to ask upward

Your own manager, or someone senior, has asked you to do something. It is not clearly wrong. It is not clearly fine. These questions are what a careful person asks and are not insubordination, whatever the tone in which they are received.

"What is this for?"

A legitimate request has a purpose that can be stated. Reassuring: a purpose, and one that the request actually serves. Worrying: "just do it" or a purpose that does not fit the request. Follow-up: "Is there another way to achieve that?" Offering an alternative is cooperation, and a refusal to consider one is information.

"Who else has approved this?"

Reassuring: names, and they are the right names. Worrying: "it doesn't need approval" for something that plainly does, or "I'll handle that side". Follow-up: "Can I check with them?" A request that the asker does not want checked is a request the asker does not want on the record.

"Can I have that in writing?"

Reassuring: yes, and it arrives. Worrying: "you don't need it in writing" or "let's keep this between us".

This question resolves most cases. A request that cannot be written down usually cannot be defended, and both parties know it. If the answer is no, you have your answer. What you do next depends on what was asked.

Where the request concerns wrongdoing of certain kinds, a disclosure may be protected by law, as the UK's whistleblowing framework shows for one jurisdiction. Where it touches anything legally governed, the next conversation is with counsel, and the structured method for weighing your obligations is in ethical dilemmas.

"If this goes wrong, whose decision was it?"

Ask it plainly, not as a threat. Reassuring: "mine", from the person asking. Worrying: "yours, you're the one doing it". A person who wants the outcome without the authorship is asking you to carry something they will not.

What the answers sound like, side by side

Why the follow-up matters more than the question

Anyone who has worked for a while has a first answer ready for most of these. The first answer is a performance, sometimes an honest one, sometimes not, and you cannot tell which from the words.

The follow-up is asked of a person who has used their prepared answer. What comes next is composed on the spot, and it is the closest you will get to what they think. Make a habit of one follow-up, always, in the same tone, so that it is never an interrogation.

Why this matters is in leadership ethics. What reaches you is filtered by what people have seen happen to others who brought things. Questions are your only tool to pull information through that filter.

The other side of that filter, where the person deciding whether to tell you stands, is in employee ethics. Read it before you ask any of the above. It tells you what your questions cost the person answering.

Common questions

Will these questions make my team feel interrogated?

Not if they are routine. The damage comes from asking them only of the person you suspect. Ask them of everyone, in the same order, in the same tone, every time.

What if my manager refuses to put a request in writing?

Write it yourself: a message confirming what you understood you were asked to do, and asking to be corrected if you have it wrong. Their reply, or their silence, is the record.

How many follow-ups is too many?

One, per question, per conversation. A second follow-up is an interrogation, and a person who has given two composed answers has given you what they are going to give.