How to Hire for Curiosity at a 75-Person Company

Where this started

I recorded a podcast recently, and my guest opened with a line I have not stopped thinking about: "The thing we have to index most on is curiosity."

Agreeing with that on air costs nothing. Doing it at 75 people means working with no learning and development team, hires who need to be productive within a month, and hiring decisions made between other meetings. Under those conditions curiosity loses to whatever is easiest to verify on a resume.

So I took away a practical question: what would it take to make curiosity count in a real hiring decision at our size?

Picture two candidates for the same customer success role. Both have five years of experience and strong references. One answers every question you ask and stops. The other asks what the customer was trying to do before they bought the product. On paper they look the same, and the difference only shows up if your interview is built to surface it.

What follows is the version we would use: four interview questions for each of three role families, a four-point score, and a few lines for reviews and promotions.

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How to use this

Curiosity gets its own score in every hiring loop, from one named interviewer, on a 1 to 4 scale. At 75 people that is enough structure to change who you hire without adding process nobody follows.

Each role family below has four interview questions. Use two in a 20 minute slot and keep the other two as backups. The same interviewer scores curiosity for every candidate in that role so the scale stays consistent.

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• Score 1, no evidence. Answers only what was asked. Asks no questions about the problem or the business. Takes the brief as given.
• Score 2, reactive. Curious when prompted. Questions are about logistics, such as the deadline, the format, or who to send it to.
• Score 3, active. Asks questions that change the approach. Describes something they taught themselves recently and what they did with it.
• Score 4, driver. Reframes the problem, looks for evidence that would prove them wrong, and points to a concrete result that came from it.
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Two rules keep the score honest. First, a candidate needs a specific example with an outcome to score a 3 or 4, so enthusiasm alone tops out at 2. Second, always ask the follow-up "what happened next?" Curiosity that never produced a decision, a fix, or a changed plan is worth less than it sounds, and at your size you have little room to carry people who explore without finishing.

Technical roles

For engineers, data, and product-adjacent technical hires, the best signal comes from how they handle a problem with missing information.

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1. The underspecified brief. Give a one paragraph problem with a gap in it, for example: "Customers say the dashboard is slow. Fix it." Tell the candidate to ask you anything. Listen for whether they ask who is affected, what slow means in seconds, what changed recently, and what has already been tried. Count the questions that would change the solution. Questions about tooling or deadlines do not count.

2. Something you taught yourself. "Tell me about something technical you taught yourself in the last six months that nobody asked you to learn. Why that, and what did you do with it?" A 3 or 4 names a specific trigger (a bug, a customer complaint, a slow query) and a result (a shipped change, a doc, a decision to drop the approach).

3. A time you were wrong. "Tell me about a technical belief you held that turned out to be wrong. How did you find out?" Strong answers describe going looking for the evidence. Weak answers describe being told.

4. Questions about us. In the last ten minutes, ask "What would you want to know about how our product or our customers work that you could not get from the job description?" Score the quality of what they ask. Questions about our data model, our worst incidents, or what customers complain about most are a 3 or 4. Questions limited to benefits and remote policy are a 2.

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Follow-up probes for any answer.

• What did you try first, and why did you drop it?
• Who did you ask for help, and what did you ask?
• What would you do differently now?

Scoring note. For senior technical hires, require a 3 or higher. For early career hires a 2 with a clear trajectory is acceptable, since they have had less room to show it. A 1 is a no for any technical role regardless of other strengths.

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Customer success roles

In customer success, curiosity shows up as how far someone digs past the first thing a customer says. The requested feature is rarely the actual problem.

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1. The vague complaint. Role-play a customer: "Your product isn't working for my team." Let the candidate run the conversation for five minutes. Listen for questions about who on the team is struggling, what they were trying to do, what they did before using the product, and what success would look like in 90 days. A 3 or 4 asks at least four questions before suggesting any fix.

2. The customer who surprised you. "Tell me about a customer where what they asked for turned out to be different from what they needed. How did you find out?" Strong answers include the specific question or observation that revealed it, and what changed in the account afterward.

3. Learning a customer's business. "Pick an account you managed. What did you learn about their business that was not in the CRM, and how did you learn it?" A 3 or 4 describes reading their website, sitting in on their calls, asking about their quarter, or talking to users below the champion. A 2 describes what the customer told them in scheduled check-ins.

4. Questions about us. "What would you want to learn about our customers in your first 30 days, and how would you go about it?" Look for a plan that involves listening to calls, reading churn notes, and talking to customers, rather than reading documentation only.

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Follow-up probes for any answer.

• What did you ask that the customer did not expect?
• What did you find out that changed what you did next?
• How did you share what you learned with the rest of the team?

Scoring note. For customer success, finding the real issue behind a request drives retention and expansion, so require a 3 or higher for all hires. Reference checks can confirm it: ask a former manager for an example of the candidate finding the real issue behind a customer request.

Sales roles

Sales candidates are practiced at sounding curious, so the questions below ask for evidence and test live behavior rather than self-description.

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1. The discovery call. Role-play a prospect with a stated need and a hidden one. Give the candidate ten minutes and tell them to run a discovery call. Score the questions, not the pitch. A 3 or 4 asks about the cost of the current problem, who else is involved in the decision, and what happened the last time they tried to solve it. A 1 or 2 starts presenting the product within the first three minutes.

2. A deal you lost. "Tell me about a deal you lost. What did you learn about why, and how did you find out?" Strong answers describe going back to the buyer or a contact to ask, then changing something in the next deal. Weak answers blame price, timing, or the competitor without any evidence.

3. Learning a new market. "Tell me about the last time you sold into an industry or buyer you did not know. How did you get up to speed before your first call?" A 3 or 4 describes specific sources: customer interviews, earnings calls, forums, a conversation with someone in the role. Ask how many calls they made before they felt ready to sell.

4. Questions about us. "What would you want to know about how our customers decide to buy, and where would you look for it?" Strong candidates ask to see lost deal notes, ask who our best customers are and what they have in common, and ask what our reps hear most often in the first call.

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Follow-up probes for any answer.

• What was the most useful question you asked on that call?
• What did the buyer say that you did not expect?
• What did you change in the next conversation because of it?

Scoring note. Pair this score with the quota history, because a rep with high curiosity and a record of missing targets is a coaching risk at your size. Require a 3 or higher for roles that handle new segments or complex deals. A 2 can work for a high-volume transactional role where the playbook is fixed.

Review rubric

Add one competency called Curiosity to the review form for every role, rated against the evidence below. The reviewer must cite at least one specific example, otherwise the rating defaults to Meets.

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• Below. Worked only from the assignment as given. Did not ask about the customer, the data, or the reason behind a request. Repeated the same approach after it stopped working.
• Meets. Asks clarifying questions when a task is unclear. Looked up or learned what was needed to do the job. Adjusted an approach when shown new information.
• Exceeds. Found a problem or opportunity nobody assigned and brought it to the team with evidence. Changed their own approach or a team process based on something they learned. Sought out customers, data, or colleagues outside their function to understand an issue.
• Outstanding. Their questions changed a decision, a roadmap item, or a customer outcome in a way others can point to. Taught what they learned to the team through a demo, doc, or training. Others come to them for help framing hard problems.
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Lines to add to the review form.

• Describe one problem you found this period that nobody assigned you. What did you do about it?
• What did you learn this period that changed how you work? Who else benefited?
• Describe a decision you changed your mind on and what evidence moved you.
• Manager prompt: Give one example where this person's question or research changed the outcome of a project or account.
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Lines to add to promotion criteria.

• To Senior: consistently identifies the right question before starting work, and does so without being prompted.
• To Lead or Manager: builds curiosity in others by asking questions in reviews, making room for experiments, and responding to "I don't know yet" with support rather than pressure.
• To Director and above: shapes what the company chooses to investigate, and can show a decision that changed because of it.
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Role-specific examples managers can cite.

• Technical. Traced a recurring support ticket to a root cause in the data model and proposed a fix before it was prioritized.
• Customer success. Interviewed three users below the champion and found the adoption blocker that the check-ins had missed.
• Sales. Called back three lost deals, found a shared objection, and changed the opening pitch for the next quarter.
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Rollout at 75 people

Start with hiring, since it changes outcomes the fastest, and add the review lines at your next cycle.

1. Pick one interviewer per role family (technical, customer success, sales) to own the curiosity slot and the 1 to 4 score. Give them this post and a 30 minute calibration session where they score the same two recorded or role-played answers and compare.
2. Add a Curiosity line to the interview scorecard, next to the existing skills ratings, with the 1 to 4 scale and a required example.
3. Add the Curiosity competency and the four review prompts to the next review cycle. Brief managers on the Meets versus Exceeds examples before they write reviews.
4. Add the promotion criteria lines to the next promotion cycle.

What to check after two quarters.

• Hires made since the change: the share who scored 3 or higher, and how they compare to earlier hires at their 90 day review.
• Review ratings: whether the Curiosity ratings cite specific examples, and whether they vary across people (if everyone is Meets, the evidence requirement is not being enforced).
• Retention and quota or customer outcomes for the higher-scoring group.
• Interviewer agreement: have a second interviewer score a sample of candidates and compare. A gap of more than one point on the same candidate means the scale needs recalibrating.

With a sample this small, treat the early results as a prompt for discussion rather than proof. The goal after two quarters is to see whether the process is being used and whether the scores are consistent.

Back to the guest's line

When my guest said we have to index most on curiosity, the part left unsaid was how. At 75 people two changes carry most of it: one scored interview slot, and one review competency that requires a real example. Managers who ask questions in the meetings where decisions get made are what make both of them stick.

Pick one role family, run the interview questions for a quarter, and compare the people you hired against the ones you would have hired before.