Questions to Ask CIO
For managers, architects and senior engineers who get time with their own chief information officer: twenty questions on what they are actually measured on, which risks are accepted, where your decision rights end, and how they want problems raised.
The questions
Open any question for the note
What are the two or three things that need to be true a year from now?
Why ask it
Gives you the CIO's real scorecard, which is nearly always narrower than the published strategy. Anything you propose afterwards should map onto one of them, and anything that does not will struggle.
What is on the plan that you expect to slip, and what is holding it up?
Why ask it
More productive than asking about priorities, because it names the constraint: a vendor, an unfilled role, another department. That constraint is often the thing you are actually able to help with.
What are you hearing about IT from the rest of the business right now?
Why ask it
Tells you which complaints have reached the top and which have not. If your team's daily pain is absent from that list, you now know why nothing has moved on it.
Where are we carrying risk that we have decided to live with?
Why ask it
Accepted risk and unknown risk are different things. Knowing which items are deliberately parked stops you raising them as discoveries, which is a fast way to look uninformed.
How do you want to hear about a problem, and how early?
Why ask it
Some CIOs want the flag at the first sign; others want it with a proposed fix attached. Getting this wrong is how competent people acquire a reputation for panicking, or for hiding things.
Which decisions do you want to keep, and which would you rather I simply made?
Why ask it
Asking for decision rights directly is unusual and usually welcomed. An answer about empowerment with no examples in it means the boundary is unclear to them as well as to you.
How does the budget actually get allocated, and when is it too late to ask?
Why ask it
The planning calendar matters more than the merits of any request. The useful part of this answer is a date, and most people learn it by missing it once.
What has been tried in this area before, and why did it stop?
Why ask it
Saves you from proposing something that already failed for a reason still present. Note whether it stopped for technical reasons, political ones, or because one person left.
What would make you say no to a proposal in the first minute?
Why ask it
The disqualifiers are worth more than the criteria. Common ones are unfunded headcount, a new vendor relationship, and anything that touches identity, payroll or the general ledger.
Which number do you look at first at the start of each month?
Why ask it
Whatever they check first is the measure your work will actually be judged against, whether or not it appears in your objectives. Ask what a bad reading of it sets in motion.
Which of our platform decisions do you consider settled and not open for debate?
Why ask it
Saves you from reopening a choice that cost two years and a great deal of political capital. It also marks the edges of any architecture proposal you bring later.
Which audit, regulator or contract takes up most of your calendar?
Why ask it
Compliance work is close to invisible from inside a delivery team and often owns a third of a CIO's year. Knowing which one is live explains why unrelated requests keep sliding.
Where do you want AI used here, and where would you rather we did not?
Why ask it
Most CIOs have a much clearer view on the exclusions than on the ambitions, and the exclusions are rarely written down anywhere. Ask specifically which data is not allowed to leave the building.
Which relationship with another executive most determines whether IT succeeds?
Why ask it
Usually finance, or whoever owns the largest operational budget. Once you have the name, you understand why some projects glide through and others never get sequenced at all.
What do you actually read of what my team sends upward?
Why ask it
Reporting written for nobody consumes real hours every month. A candid answer lets you retire a dashboard, or discover that the one you assumed was ignored is read line by line.
Which cost line are you under the most pressure to bring down?
Why ask it
Points at the part of the estate where a credible saving makes you useful rather than inconvenient. Cloud spend, licensing and contractor rates are the usual three.
What would you like switched off that nobody has volunteered to own?
Why ask it
Decommissioning has no natural sponsor, so dead systems accumulate quietly. Taking one of them on is the cheapest way for someone at your level to be visibly helpful.
What skills will this team need in two years that we do not have today?
Why ask it
Converts a vague conversation about development into a named hiring and training gap. It is also the most useful thing to hear if you are deciding what to learn next.
What had the last person you moved into your leadership team done to earn it?
Why ask it
Asking for the case rather than the criteria produces behavior instead of adjectives: handling bad news early, taking over something that was going badly, being trusted outside IT.
What do you wish people at my level understood about your job?
Why ask it
An honest closer that usually produces the constraint they cannot state in a town hall, generally about board pressure, cost scrutiny, or how little slack the organization has left.
Making the Most of Time With Your CIO
Practical guidance for the conversation itself
Before the Meeting
Read what they have already said publicly
Town hall decks, the last all-hands recording, any external interview and the annual report if you have one. Asking a question they answered on stage last month spends your credibility in the first minute.
Pick three questions, not a dozen
A thirty-minute slot supports three questions with real follow-ups. A dozen questions produces a dozen short answers and nothing you can act on. Choose the ones whose answers would actually change what you do next.
Decide whether you are asking or selling
These questions work when you genuinely want the information. If you are really there to get a project approved, say so at the start and ask what would make it a yes, rather than disguising a pitch as curiosity.
Have one specific thing you can offer
Senior leaders remember the people who arrive with a problem they can help solve. A concrete offer, even a small one, converts a pleasant meeting into an ongoing relationship.
During and After
- Take the numbers and dates down verbatim. Budget cycles, headcount figures and dates are the parts you will need later and the parts you will misremember.
- When an answer is a framework, ask for the last time it happened. That single follow-up produces most of the value in any conversation with a senior leader.
- Do not fill silences. A CIO pausing before answering the accepted-risk question is deciding how much to tell you.
- Ask before you leave whether there is anything they want from you, and write down the answer exactly as given.
- Send three lines within two days: what you heard, what you are doing about it, and one date. Short beats thorough.
- Then do the thing and tell them it is done. Following through once buys you far more access than a good meeting does.
Common Pitfalls
Escalating in the meeting
Raising a specific grievance about your own manager or a peer team turns the conversation into an incident the CIO now has to handle. Ask about how such things get resolved in general instead.
Asking for a strategy overview
It is the question CIOs answer most often and the one where they are least likely to say anything you cannot read in a deck. Spend the time on constraints, accepted risk and decision rights instead.
Bringing a technology recommendation with no cost or owner attached
Every CIO fields these constantly. Without a run cost, a named owner and what it replaces, an enthusiastic recommendation reads as work being handed upward.
Treating the answers as fixed
Priorities at this level move with the board calendar, and an answer from March may be obsolete by September. Ask again rather than acting on last quarter's version for a year.