Questions to Ask Your CRO
Questions for a skip-level, a one-to-one, or an all-hands with the Chief Revenue Officer. They ask about the number the business is carrying, where the pipeline is thin, and what the revenue organisation rewards, in terms specific enough to be answerable.
The questions
Open any question for the note
What number are you carrying this year, and where did it come from?
Why ask it
Whether the target was built from capacity and pipeline or handed down from a fundraising plan changes everything downstream. A CRO who cannot explain the derivation is managing a number they do not own.
What's the first metric you look at each morning?
Why ask it
The honest answer names one or two figures and reveals what the whole function is actually optimised for. If it is bookings only, expect renewals and margin to be somebody else's problem until they become a crisis.
Which part of the funnel worries you most right now?
Why ask it
Forces a single answer instead of a tour of the strategy. Top of funnel, conversion, deal size, and cycle length imply completely different fixes, and knowing which one is live tells you where your own work matters.
What are we winning on, and what are we losing on?
Why ask it
Ask for both halves and listen for evidence from lost deals rather than positioning language. A CRO who can only describe the wins is not reading the loss reasons.
How much of next year's revenue is already contracted?
Why ask it
The proportion that is committed versus needs to be won is the single most useful number for understanding pressure in the business. It also predicts how the year will feel for everyone selling.
Where does pipeline coverage actually stand against what we need?
Why ask it
A specific ratio, by segment and by quarter, is the answer. Anything reassuring but unquantified usually means coverage is being met with old opportunities nobody has qualified out.
At what stage does a forecast become something you'd bet on?
Why ask it
This gets at forecast discipline, which is where most revenue leaders are either rigorous or exposed. Watch for whether the answer references evidence in the deal or a rep's confidence.
If we miss the number this year, where will it have come from?
Why ask it
Asking about failure in advance is uncomfortable and far more informative than asking about plans. A leader who has already named their two biggest risks is managing them; one who deflects is not.
What is marketing supposed to be delivering, and are we getting it?
Why ask it
The gap between the agreed lead or pipeline commitment and actual delivery is where most internal friction lives. Notice whether they describe a shared number or two teams keeping separate scores.
What is our churn telling us about who we should stop selling to?
Why ask it
The most valuable revenue decisions are often about turning business away. If churn analysis has never changed the target customer definition, the loss data is being collected and ignored.
What's the reasoning behind our current pricing, and what would make you change it?
Why ask it
You are listening for whether pricing was tested and reasoned or inherited and defended. The trigger conditions for change matter more than the current model.
Which deals do you get personally involved in, and why those?
Why ask it
Where a CRO spends their own selling time reveals the real priorities: strategic accounts, rescues, or wherever the largest number is that quarter. It also tells you what gets executive air cover and what does not.
Where do sales and product disagree most, and how does that get settled?
Why ask it
Every company has a standing argument about the roadmap and what is being promised in deals. The interesting part is the mechanism for resolving it, and whether there is one at all.
How do you decide when to redraw territories or change quotas?
Why ask it
These changes decide who can hit their target and who cannot, so the process matters to everyone in the field. Vague answers here are why good sellers leave in January.
What does the board push you on that the rest of us never hear?
Why ask it
Gets you the pressure the organisation is actually responding to: efficiency, net retention, sales cycle, cost per acquisition. It usually explains a recent decision that looked arbitrary from below.
Who on the team is doing something the rest of us should copy?
Why ask it
A specific name and a specific practice is a good sign, and a useful thing for you to go and learn. Generic praise for the whole team suggests they are not close enough to the work to know.
What behaviour gets someone promoted here, and what quietly stalls a career?
Why ask it
The second half is the part nobody volunteers. Answers about hitting a number differ sharply from answers about developing others, and both are worth knowing before you plan your next two years.
What did you get wrong last year?
Why ask it
A leader who names a real misjudgement, a hire, a segment, a bet on a channel, and what it cost, is telling you how learning happens here. A polished non-answer is also data.
If you had one more headcount tomorrow, where would it go, and what's stopping you?
Why ask it
Reveals both the perceived constraint and the internal politics around getting resource. The reason it has not happened is usually more informative than the role they name.
What could someone in my role do that would genuinely help you hit the number?
Why ask it
Ends with something actionable and shows you are not just gathering intelligence. Push for one specific thing rather than accepting encouragement, and then go and do it.
How to use these questions
Practical guidance for the conversation itself
Match the question to the setting
All-hands Q and A
Ask about strategy, priorities, and what the board is pushing on. Anything about individuals, quotas, or a possible miss puts a CRO in a position where they cannot answer honestly in front of the company, so you will get the safe version.
Skip-level or one-to-one
This is where the questions about the funnel, forecast discipline, churn, and what they got wrong belong. Send one or two in advance if the answer needs a number, and you will get figures rather than impressions.
As a candidate interviewing
Contracted revenue, coverage, quota attainment across the team, and recent territory changes tell you whether the role is achievable. A CRO who will not discuss attainment distribution is telling you something.
Reading the answers
- Numbers with periods attached, rather than adjectives: coverage by quarter, attainment across the team, retention as a percentage.
- Loss reasons described in the customer's language, which is a sign the company debriefs deals it did not win.
- A named owner for every problem mentioned, since revenue issues without an owner tend to reappear at the next quarterly review.
- Consistency between what is said about priorities and where the leader spends their own week.
- Willingness to describe a risk before you ask about one, which is the clearest indicator of a leader who is actually forecasting rather than hoping.
What to avoid
Public questions with only one safe answer
Asking in a large meeting whether the quarter is at risk, or whether layoffs are coming, forces a non-answer and costs you credibility. Take those to a one-to-one.
Asking for information you cannot be given
Named account details, individual compensation, and anything under a quiet period are off limits regardless of how the question is phrased. Ask about the mechanism instead of the specific case.
Collecting insight and doing nothing
The last question in this list commits you to something. A CRO remembers the person who asked what would help and then reported back a month later, and forgets everyone who only asked.