Before You Hire a CRO, Ask Them to Do the Selling

A CRO candidate can describe a forecasting process, explain a compensation plan, and present a convincing account of organizational change. I would still want to see what happens when a buyer says, “We already have a vendor, and switching is not a priority.”

That is a different test. It asks whether the person can uncover a reason to act rather than simply explain how a sales organization should operate.

What the source says—and where our view begins

The SaaStr headline and accompanying snippet argue that a CRO or VP of Sales must also be a great salesperson. The snippet identifies a hiring mistake: founders selecting someone with many strengths who is not particularly strong at selling personally. It also expresses the author’s view that this mistake is widespread among B2B CEOs as they begin scaling.

The supplied material does not establish how often this happens or quantify its consequences. I would treat it as an editorial warning, not a measured prevalence claim.

Our view at Leads.biz is narrower and actionable: personal selling ability deserves its own assessment in a revenue-leadership hiring process. It should not be inferred from title, tenure, or fluency with sales terminology.

Test the work, not the performance polish

I would give each finalist the same fictional account brief, product summary, and meeting objective. The brief should specify a buyer role, an existing alternative, a relevant business constraint, and one important unknown.

For example, the exercise could involve an operations leader evaluating a workflow product while facing an implementation-capacity constraint. The candidate’s objective would be to earn a mutually useful next meeting—not force a purchase decision in a simulated first call.

Use a 25-minute conversation followed by a 10-minute debrief. Tell candidates the format in advance. This is a proposed assessment design, not a benchmark established by the source.

I would score five observable behaviors:

• Discovery: Do they ask what the current process costs the buyer in time, effort, or missed work before recommending a change?
• Listening: Does the next question reflect the buyer’s previous answer?
• Qualification: Do they distinguish a relevant problem from an active buying priority?
• Objection handling: Do they investigate the implementation constraint rather than dismiss it?
• Next-step discipline: Do they propose a specific follow-up with a purpose, participants, and information needed?

A simple scale can keep the discussion concrete: zero for absent, one for attempted, and two for clearly demonstrated. The score should inform judgment, not substitute for it.

Use the debrief to assess coaching potential

Selling well and teaching someone else to sell are separate capabilities. I would test both.

After the exercise, ask the candidate to identify one question they should have asked, one assumption they made, and one moment when they changed direction. Then ask how they would coach a rep who had conducted the same conversation.

I would favor specific answers over broad self-assessments. “I needed to ask who owns implementation capacity before proposing a timeline” gives an interviewer something to evaluate. “I would build more rapport” needs further explanation.

This also creates a useful distinction: can the candidate explain a repeatable decision, or only describe their personal style? My preference would be for a leader who can make their reasoning visible without insisting that every rep imitate them.

Give marketing a defined role in the assessment

I would include a marketing counterpart in the debrief, with a focused responsibility: evaluate how the candidate connects audience selection, messaging, and sales discovery.

Ask which account attributes justified the outreach. Ask what the conversation revealed that the original brief missed. Ask which message they would stop using after hearing the buyer’s constraint.

Before running that exercise, define the audience precisely. Industry, company size, geography, and buyer role provide a practical starting point when you build a prospect audience. Keep the interview itself fictional; the candidate does not need live prospect information to demonstrate judgment.

Keep selling ability in proportion

I would not hire a CRO solely because they handled this exercise well. Leadership, hiring, forecasting, and cross-functional judgment still need separate evaluation.

But I would not let strengths in those areas erase weak evidence of selling ability either. The hiring question is not whether the candidate can become the team’s permanent closer. It is whether they understand the work well enough to demonstrate it, diagnose it, and help others improve it.

That is the standard I would put on the scorecard before the first interview—not add after an impressive résumé has already shaped the decision.