Diversity and Inclusion Questions to Ask Senior Leaders
Twenty questions to put to executives and board members, written to get a number, a date or an example rather than a position. They cover missed targets, pay reviews, promotion decisions, retention by group, budget, unpaid work, and what leaders got wrong. Suited to a skip-level, a town hall, or a board session.
The questions
Open any question for the note
What are the current numbers, and where can employees see them without asking you?
Why ask it
Published data behaves differently from data held by leadership, because publication forces the numbers to be reconciled. If nobody can find them, the figures are being used for reporting outward rather than managing inward.
Which of last year's goals did you miss, and what was the reason?
Why ask it
Every organization misses some. A leader who cannot name one either does not track them closely or is unwilling to say, and both answers tell you how much the rest of the session is worth.
How were your own direct reports hired or chosen?
Why ask it
Executive teams are usually assembled through personal networks, which is exactly the mechanism the rest of the program is meant to counteract. The answer shows whether the leader sees that tension.
What did the last pay review find, and what did it cost to fix?
Why ask it
Any company can run an analysis. A review that found nothing and cost nothing was usually scoped so that it could not find anything, so ask what was included and what was excluded.
Who is accountable when a target is missed, and does it affect anyone's compensation?
Why ask it
Accountability that cannot be located anywhere specific does not exist. If the answer is that everyone owns it, ask which single person would have to explain a miss to the board.
How do promotion decisions get made one level below you, and who challenges them?
Why ask it
This is where most inequity is produced and where senior leaders are least informed. A leader who has never sat in a calibration session at that level is describing a process they have not seen.
What does retention look like broken down by group, and where is the drop?
Why ask it
Hiring numbers can be improved without anything else changing, so departures are the honest measure. Ask whether exit interviews are read by anyone with the power to act on them.
How much budget sits behind this work, and who controls it?
Why ask it
Budget and its owner tell you the actual priority more reliably than any statement. Money held by a function that must request permission for each spend is not really allocated.
Which employee network has asked you for something recently, and what did you do?
Why ask it
A specific request and a specific response is the most concrete evidence available of whether these groups have any leverage. Vague warmth toward them usually means no.
What proportion of this work is done by people whose job it is not?
Why ask it
Unpaid effort by the people most affected is the standard way a program looks active while resting on goodwill. It also predicts that the program will disappear in a difficult quarter.
What complaint reached you personally in the last year, and how did it end?
Why ask it
Ask about an outcome, not a policy. If nothing has reached this level, that may mean the process resolves matters well or that it absorbs them, and the follow-up question is which.
How do you know whether somebody who raises an issue is worse off afterward?
Why ask it
Retaliation is usually quiet: a reassignment, a cooler rating, a project that goes elsewhere. Very few organizations track outcomes for people who complained, and the honest answer is often that they do not.
What did your last engagement survey say that you did not want to hear?
Why ask it
The framing invites candor and most leaders will take it. Watch whether the uncomfortable finding was acted on or reclassified as a communications problem.
Who is in your succession plan, and how did they get there?
Why ask it
Succession lists are where the next decade of leadership is decided, usually informally and out of sight. How people arrived on the list matters more than who is currently on it.
Which supplier or partner decision has this actually changed?
Why ask it
Supplier diversity commitments are easy to state and easy to leave unimplemented. One named contract with a date attached is worth more than a stated percentage target.
What did you personally get wrong about this in the last few years?
Why ask it
A leader who has revised a view can usually name it precisely; one who has not will answer with a general lesson about listening. The specificity is the whole signal.
Which initiative did you stop, and why?
Why ask it
Programs that never end tend to be programs nobody evaluates. Stopping something is evidence of judgment, and the reason given tells you what criteria are actually applied.
What is the most expensive change you have made here, and was it worth it?
Why ask it
Cost is the clearest proxy for seriousness, and the second half checks whether anyone measured the result. Expect the answer to be a salary correction or a rebuilt hiring process.
What would make you conclude a program is not working and should end?
Why ask it
Asking for the failure condition in advance is harder to answer than asking for a goal. Leaders with no such condition will keep reporting activity indefinitely.
What is genuinely outside your control here, and what is inside it?
Why ask it
A closing question that separates realistic constraints from the ones being used as cover. Anything placed outside the leader's control that plainly sits inside it is the most useful thing you will learn.
Asking senior people these questions
Practical guidance for the conversation itself
Choose the setting
Town hall
Public forums reward a single short question with a factual answer, such as where the numbers are published or what last year's miss was. Long questions get summarized into something easier before they are answered.
Skip-level or small group
This is where the questions about promotion decisions, retaliation and unpaid work belong, because they need a follow-up and a public setting does not allow one.
Board or investor session
Budget, accountability, pay review scope and succession are board-level matters and phrasing them as governance questions gets further than framing them as culture.
Written in advance
Submitting one or two questions ahead of time produces a researched answer instead of a recollection. It also makes the question harder to skip over on the day.
Getting a real answer
- Ask for one number or one example, never both plus context. Compound questions get answered on whichever part is easiest.
- Have a single follow-up ready: and what changed as a result. Most deflection survives the first question and not the second.
- If it is handed to HR, ask what the leader themselves decided. Delegation of the answer is itself informative.
- Note whether you are given activity or outcomes. Training completion is activity; a rewritten promotion rubric is an outcome.
- Ask for a date and a name at the end. A commitment with neither will not be findable in six months.
Asking when there is risk to you
In some organizations these questions are read as disloyalty, and it is worth deciding in advance how much exposure you are willing to take. Anonymous channels, an employee network, a union representative or a works council can carry a question without a name attached, and a question asked by a group is much harder to dismiss than the same question from one person. If you do ask openly, keep the tone factual and the question narrow, since a specific request for a number is harder to characterize as an attack than a general challenge. Write down what was said and when. If your standing changes afterward, that record is the only thing that will make the pattern visible.
What goes wrong
Asking for a commitment instead of a fact
Leaders can promise almost anything at low cost. Facts about last year cannot be produced on the spot, which is why they are the better ask.
Letting the answer end the exchange
A fluent answer with no specifics in it should be followed by a request for one example. Accepting it graciously teaches everyone present what standard applies.
Making it about one leader
Questions that read as a personal accusation get defended rather than answered. Aim at the process and the numbers, which are harder to take personally.
Not recording what was said
The value of asking accrues over time as commitments are compared with outcomes. Without notes and dates, next year's session starts from nothing.