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Day 10 of 20 Β· AI for Recruitment

Interview Questions That Reveal Fit

Most interviews fail before they start β€” not because the candidates are wrong, but because the questions are. Generic questions get generic answers. "Tell me about yourself" tells you almost nothing. "What's your greatest weakness?" reveals nothing except how well someone has rehearsed.

The best interviewers ask questions that are impossible to fake. Questions tailored to the specific role, the specific team, and the specific challenges the person will face in the first 90 days.

Today you will learn how to use AI to generate interview questions that actually reveal whether a candidate can do the job β€” and whether they will thrive doing it.

Competency-based questions that dig deep

Competency-based interviewing is the gold standard for a reason: it asks candidates to prove their skills through real examples, not hypothetical promises.

The framework is simple. For each core competency the role requires, you create questions that demand specific, verifiable evidence:

Leadership: "Tell me about a time you had to lead a team through a project where the requirements changed mid-way. What did you do, and what was the outcome?"

Problem-solving: "Describe the most complex problem you solved in the past year. Walk me through how you diagnosed it, what options you considered, and why you chose your approach."

Collaboration: "Give me an example of a time you disagreed with a colleague on an important decision. How did you handle it? What was the result?"

The key principle: past behavior predicts future behavior. A candidate who can describe a specific, detailed example of leading through ambiguity has proven the skill. One who speaks only in generalities has not.

AI excels at generating these questions because you can feed it the job description and ask for competency-aligned probes specific to that role.

Knowledge Check
Why are competency-based questions more effective than hypothetical ones?
A
They are shorter and easier to ask
B
They require candidates to demonstrate skills through real past examples, which are harder to fake
C
Candidates prefer them because they are less stressful
D
They are required by employment law
Hypothetical questions ("What would you do if...") test imagination, not experience. Competency questions ("Tell me about a time you...") require real evidence. A candidate might give a brilliant theoretical answer to a hypothetical scenario but have never actually done it. Past behavior is the most reliable predictor of future performance.

Culture-fit questions without the bias

"Culture fit" has earned a bad reputation β€” and for good reason. Too often it becomes code for "hire someone who looks and thinks like us." That is not culture fit. That is cloning.

Real culture fit means alignment on values and working style, not personality or background. AI can help you generate questions that assess genuine alignment without introducing bias:

Values alignment: "Our team values transparency β€” even when the news is bad. Tell me about a time you had to deliver difficult feedback or share bad news with a stakeholder. How did you approach it?"

Work style: "We operate with a high degree of autonomy β€” each person owns their projects end-to-end. Describe a situation where you had to figure out priorities and drive a project forward without much guidance."

Adaptability: "Our industry moves fast and priorities can shift quickly. Give me an example of a time you had to abandon a plan you had invested significant time in. How did you handle the pivot?"

Notice what these questions do not ask: where you went to school, what you do for fun, or whether you would be "fun at a happy hour." They probe work behaviors that predict success in the specific environment β€” nothing more.

Interview Question Types β€” Competency, Culture-Fit, Technical, Situational
Four types of questions that reveal whether a candidate can do the job and thrive.

Technical assessment questions

For technical roles, the interview needs to go beyond "Do you know this tool?" toward "Can you think through technical problems the way this job requires?"

AI can generate role-specific technical questions that test depth, not just familiarity:

The prompt: "Generate 5 technical interview questions for a [role title]. The role requires expertise in [specific skills/tools]. Each question should have three levels: a surface-level answer (acceptable), a solid answer (good), and an exceptional answer (hire signal). Focus on practical application, not textbook definitions."

This three-tier structure is incredibly useful for interviewers. It gives them a rubric in real-time β€” they know what a mediocre answer sounds like versus a standout one, even if they are not deeply technical themselves.

For hiring managers who are not technical: "Create 5 questions for a non-technical interviewer to assess a [technical role]. Each question should evaluate the candidate's ability to explain complex concepts simply, collaborate with non-technical stakeholders, and prioritize technical decisions based on business impact."

Knowledge Check
Why is the three-tier answer structure (acceptable, good, exceptional) useful for interviewers?
A
It ensures every candidate gets the same score
B
It allows candidates to choose which level they want to answer at
C
It gives interviewers a real-time rubric so they can evaluate answer quality even if they are not experts in the topic
D
It makes the interview shorter
Most interviewers β€” especially hiring managers pulled into technical interviews β€” struggle to evaluate whether an answer is genuinely good or just sounds good. The three-tier structure gives them concrete benchmarks. They can compare what they heard to what an acceptable, good, and exceptional answer looks like and score accordingly.

Situational and behavioral frameworks

Beyond competency questions, two powerful frameworks round out your interview toolkit:

STAR framework questions (Situation, Task, Action, Result) β€” These structure the candidate's response so you get complete stories, not fragments:

"Tell me about a time you [faced specific challenge]. What was the situation? What was your specific role? What actions did you take? What was the measurable outcome?"

The prompt: "Generate 5 STAR-format interview questions for a [role title] based on this job description: [paste JD]. Each question should target a different key competency from the JD."

Future-scenario questions β€” These test how candidates think, not just what they have done:

"In this role, you will face [specific realistic challenge]. Walk me through how you would approach it in your first 30 days."

The key is making the scenario realistic and specific to the role. Generic scenarios get generic answers. When the scenario mirrors an actual challenge the team is facing, you get to see how the candidate's brain works on problems they will actually encounter.

πŸ€–
AI Assistant
online
I need interview questions for a Senior Customer Success Manager role at a B2B SaaS company. The team manages enterprise accounts ($100K+ ARR). Key challenges: reducing churn, expanding accounts, and managing difficult renewal conversations. The JD emphasizes relationship building, data-driven decision making, and cross-functional collaboration with product and sales teams. Give me 8 questions covering different competencies β€” mix of behavioral and situational.
Here are 8 interview questions for your Senior CSM role: **Relationship Building (Behavioral):** 1. "Tell me about an enterprise account that was at risk of churning. How did you identify the risk, what steps did you take to save it, and what was the outcome?" **Data-Driven Decision Making (Behavioral):** 2. "Describe a time you used customer data or product usage metrics to identify an expansion opportunity. What signals did you look for, and how did you translate data into a conversation with the customer?" **Difficult Conversations (Behavioral):** 3. "Walk me through a renewal conversation where the customer pushed back on price or questioned the value of the product. How did you prepare, what was your approach, and how did it resolve?" **Cross-Functional Collaboration (Behavioral):** 4. "Give me an example of a time you worked with the product team to get a customer's feature request prioritized. How did you make the case internally, and what was the result?" **Strategic Thinking (Situational):** 5. "Imagine you inherit a portfolio of 15 enterprise accounts. Three are up for renewal in 60 days, two have declining product usage, and one just had an executive sponsor leave. How do you prioritize your first two weeks?" **Expansion Mindset (Situational):** 6. "A customer is using 60% of the features they are paying for. They seem satisfied but not enthusiastic. What is your approach to turning this into an expansion conversation rather than a churn risk?" **Resilience (Behavioral):** 7. "Tell me about a time you lost a major account despite your best efforts. What happened, what did you learn, and how did it change your approach going forward?" **Leadership & Influence (Situational):** 8. "Our sales team sometimes overpromises during the deal cycle, which creates challenges for CS during onboarding. How would you address this pattern without creating tension between teams?" *Tip: Questions 1-4 require real examples β€” listen for specifics. Questions 5-8 test strategic thinking β€” listen for structured approaches, not just instinct.*
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Briefing hiring managers on interview questions

Generating great questions is half the battle. The other half is making sure hiring managers actually use them well. Most hiring managers have never been trained to interview β€” they default to gut feelings and favorite questions that may not be relevant to the role.

Use AI to create a one-page interviewer brief for each role:

The prompt: "Create a one-page interview guide for a hiring manager conducting a 45-minute interview for a [role title]. Include: the 5 most important questions to ask, what a strong answer looks like for each, what red flags to watch for, topics to avoid (illegal or biased questions), and a suggested time allocation for each section."

Send this to every interviewer 24 hours before the interview. It takes them five minutes to read, and it dramatically improves the quality and consistency of their feedback.

Knowledge Check
What is the best way to prepare a hiring manager who has not been trained in interviewing?
A
Let them wing it β€” they know the role best
B
Have the recruiter sit in on every interview to guide them
C
Send them a one-page interviewer brief with questions, strong answer indicators, red flags, and time allocation
D
Send them the candidate's resume and hope for the best
Most hiring managers interview infrequently and have no formal training. A concise, role-specific brief gives them structure without overwhelming them. It ensures they ask relevant questions, know what good looks like, and avoid problematic questions β€” all in a format they can review in five minutes.
Final Check
A candidate gives a vague answer to a competency question β€” "I'm generally good at handling conflict." What should the interviewer do?
A
Accept the answer and move to the next question
B
Rephrase the question as a hypothetical instead
C
Mark the candidate down immediately for a weak answer
D
Probe deeper with a follow-up: "Can you walk me through a specific example?"
Vague answers are not necessarily bad answers β€” some candidates need prompting to get specific. A simple follow-up like "Can you give me a specific example?" often unlocks detailed, impressive responses. The goal is to help the candidate demonstrate their best, not to trip them up.
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Day 10 Complete
"Generic questions get rehearsed answers. Role-specific, competency-based questions β€” generated from the actual JD β€” reveal who can truly do the job. AI builds your question bank in minutes."
Tomorrow β€” Day 11
Structured Interview Scorecards
Tomorrow you'll build AI-generated scorecards that make interview feedback consistent, fair, and actionable.
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1 day streak!