Questions to Ask a Chief Revenue Officer
For sales leaders, candidates, investors and operators meeting a CRO. Twenty questions on the number and how much of it is already contracted, forecast accuracy, quota attainment and ramp, where deals die, retention and renewals, the comp plan, and what breaks if revenue doubles.
The questions
Open any question for the note
What is the number this year, and what was it last year?
Why ask it
The growth rate matters more than the absolute figure, and the two together show whether the plan is an extrapolation or a step change. A CRO who cannot give both immediately is not the person building the plan.
How much of that number is already contracted before anyone sells anything?
Why ask it
In subscription businesses a large share of the year is renewals rather than new business. Separating the two shows how much real selling is required, and stops a retention problem hiding behind a headline growth figure.
What has your forecast accuracy been over the last four quarters?
Why ask it
This is the best single measure of whether a CRO controls their business. Landing within a few points repeatedly is impressive. A large miss in either direction, including an overshoot, means the pipeline is not understood.
What share of the team hit quota last year?
Why ask it
The percentage tells you whether quota is set realistically. When only a minority hit target, the number was worked backwards from a board plan, and the consequences show up as attrition, heavy discounting and a forecast built on hope.
How long does a new rep take to become productive, and how many make it?
Why ask it
Ramp time and survival rate together give the true cost of a hire. A long ramp with heavy first-year attrition makes recruiting a treadmill, and any plan assuming new headcount produces revenue on schedule is fiction.
What is your average deal size and cycle length, and who closes fastest?
Why ask it
The last part is the useful part. The fastest closers usually cluster around a segment or use case the company sells well without having deliberately targeted it. Averages conceal that; the outliers are where the strategy is hiding.
Where do deals die?
Why ask it
Strong answers name a stage and a cause: security review, no economic buyer, procurement, an entrenched incumbent, a champion who left. Losses blamed mostly on price usually mean value was never established earlier in the process.
How much of the pipeline do you believe, and how do you know?
Why ask it
This tests pipeline hygiene. Look for stage definitions that require evidence from the customer rather than the rep's optimism, and for stale deals being removed regularly. A pipeline that only ever grows is a morale exercise.
What does the comp plan pay for, and what behaviour does that produce?
Why ask it
Compensation explains conduct better than any strategy document. Accelerators on new business explain neglected renewals; paying on bookings rather than collections explains badly fitting customers. Ask them to trace the plan through to what reps do in the last week of a quarter.
Who is your best rep, and could you hire nine more of them?
Why ask it
The second half is the real question. If your top performer wins through unusual relationships or deep personal expertise, the model does not scale by hiring. If they win because the process works, it does.
What are gross and net retention, and who owns the renewal?
Why ask it
The two figures answer different questions, and net retention above one hundred percent can conceal real customer loss. Ownership matters just as much: renewals nobody owns are the most common source of a surprise miss.
When a customer churns, who finds out first and what happens next?
Why ask it
You want the mechanism and how early the warning arrives. A company that learns about churn from the cancellation notice has no usable health scoring, and the answer also shows whether anything post-sale is genuinely in the CRO's remit.
How much discounting are you doing, and when did someone last refuse a discount?
Why ask it
Routine discounting is a pricing or positioning problem surfacing in sales. Ask for the average discount and the approval threshold. If nobody has walked away from a deal recently, the list price is decorative.
How much revenue comes through partners, and would it happen without your direct team?
Why ask it
Partner revenue is often quoted as a percentage while consisting of a few deals the direct team sourced anyway. Ask how many partners produced anything at all last quarter, because a channel only counts once it generates deals unaided.
What does marketing owe you, and do you get it?
Why ask it
This exposes the real relationship between the two functions. Look for an agreed number of qualified opportunities with a written definition. If the answer is that marketing provides awareness, sales is sourcing its own pipeline and the org chart is misleading.
What is in your sales process because of one bad deal in the past?
Why ask it
Processes accumulate steps from old crises: a legal review after one damaging contract, an approval after one discount that went wrong. Knowing which steps came from where, and whether they still earn their place, shows whether anyone maintains the process or only adds to it.
What was the last quarter you missed, and what did you actually change?
Why ask it
Everyone misses eventually. What matters is whether the response was structural, redrawn territories, a higher qualification bar, headcount moved between segments, or simply more activity. More calls is what teams do when the problem has not been diagnosed.
Which customers should you never have sold to?
Why ask it
Naming badly fitting customers proves the CRO looks past the signature. Someone who cannot think of any is either not seeing churn data or is measured purely on bookings, which is precisely how a support and renewals problem gets built.
If revenue doubled, what breaks first?
Why ask it
This tests the plan against reality. Credible answers name a constraint: onboarding capacity, one solutions engineer who knows the enterprise product, the billing system, a legal review that already takes three weeks. Vagueness means nobody has checked operations against the growth plan.
What are you being asked to deliver that you do not think is achievable?
Why ask it
Asked late and directly, this often gets a straight answer, and it is usually the most valuable thing in the conversation. A CRO who publicly agrees to an impossible number will hire against it, spend against it, and lose the team doing it.
Getting past the dashboard with a CRO
Practical guidance for the conversation itself
Before the meeting
Agree definitions before you compare numbers
Bookings, ARR, pipeline and qualified opportunity mean different things in different companies, and a favourable definition can move a figure substantially. Ask how each term is calculated here before you draw any conclusion from it.
Work out which motion this is
A team selling six-figure contracts to enterprises through a long committee process is a different business from a self-serve product with a small sales assist. Ramp times, cycle lengths and quota attainment only mean something when compared within a single motion.
Know what stage the company is in
A CRO hired to find repeatability is judged on discovering what works. A CRO hired to scale a motion that already works is judged on execution and hiring. Asking scale questions of the first, or invention questions of the second, wastes the conversation.
How to ask
- 1Ask for the number, then ask how it is defined, then ask what it was a year ago. Any one of those alone is easy to present favourably.
- 2Follow every process answer with the last deal it was applied to. Process described in the abstract is usually aspirational.
- 3Ask what they stopped doing. Revenue plans that only add motions, segments and headcount are wish lists.
- 4When you hear an average, ask for the distribution. In sales the spread between reps is where most of the information is.
- 5Let a pause sit after an answer about a missed quarter or a departed rep. The candid half arrives second.
- 6Ask to speak to a rep and someone in revenue operations. What the front line says about the process is the best check on what you have just been told.
If you are joining their team
- Ask what percentage of the team hit quota last year, and get the number rather than a characterisation of it.
- Ask how the territory or patch you would inherit performed, and what happened to the person who had it.
- Ask for the comp plan in writing, including how accelerators work and when commission is actually paid.
- Ask where inbound leads come from and how they are allocated. Compensation is meaningless without knowing how the pipeline reaches you.
- Ask how long the average rep stays. It is a question about the manager as much as the market.
If you are hiring a CRO
- Give them your real pipeline and forecast in the process and ask what they see. The diagnosis is the interview.
- Check whether their previous success came in a comparable motion, deal size and sales cycle. These are not transferable in the way titles suggest.
- Ask for references from a rep they managed and a marketing counterpart, not only the CEO above them.
- Establish before an offer who owns pricing, renewals, customer success and revenue operations. Most CRO failures trace back to that being left ambiguous.
- Ask what number they would sign up to, and why. A candidate who accepts your number without negotiating the assumptions behind it is telling you something.
Answers to discount
- Activity metrics offered in place of pipeline conversion or forecast accuracy.
- A pipeline coverage ratio quoted with no reference to how stages are defined or policed.
- Every previous miss attributed to marketing, product or the market, with none to sales execution.
- Retention discussed only as net revenue retention when customer counts are falling.
- A plan that depends entirely on hiring, with no answer on ramp time or historical rep attrition.