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Better Hires Start With Better Interviewers

Interviewing well is a skill, and not every people leader gets the training (or practice) they need to do it right. Why? Because most managers don’t hire that often, and when they need to hire, there is no time for re-training them.

But the good news is that AI can help, and it’s more accessible than you might think.

Top 5 Cringe-Worthy Questions to NOT Ask in a Job Interview

1. What is your greatest weakness?
Why it’s cringe: It’s overused and invites canned, inauthentic answers.

Most candidates are prepared to spin a strength into a “weakness” (e.g., I care too much), so it reveals very little.

2. Where do you see yourself in five years?
Why it’s cringe: It puts candidates in a position to guess what the interviewer wants to hear.

Today’s career paths are rarely linear, and this question often misses real motivators or potential.

3. If you were an animal, what would you be and why?
Why it’s cringe: It’s vague, irrelevant, and can feel gimmicky.

Unless you’re hiring for an improv role, it’s not a helpful predictor of success.

4. Why should we hire you?
Why it’s cringe: This shifts the burden to the candidate to make a pitch without context.

A better approach is to ask situational or behavioral questions that draw out examples of past success.

5. How would your last boss describe you?
Why it’s cringe: It encourages speculation and can lead to awkward or performative answers.

It’s better to ask for real feedback examples or how they’ve grown through previous feedback.

Want to help your managers avoid these traps? 

AI can generate targeted, role-specific questions with the right prompt.

We often focus on using AI to screen candidates, but what about using it to coach the humans doing the interviewing?

Imagine giving a new manager an AI-powered practice round that gives real-time feedback while helping them refine behavioral questions for different roles.

Now we’re not just speeding up hiring—we’re making it smarter.

What is really cool is that AI doesn’t judge.

It gives managers space to rehearse, reflect, and improve without the pressure of performing in front of a live audience.

Plus, when you build strong prompts (something Paul’s always ready to help with), AI can simulate scenarios that are highly relevant to your company, your culture, and your hiring goals.

You can prompt AI to act like a candidate with a specific skillset, background, or communication style—and let your manager practice interviewing that person.

No more “one-size-fits-all” interview prep.

And this isn’t just for new managers.

Even seasoned leaders can benefit from fresh, tailored coaching—especially when they’re hiring for evolving roles in data, tech, or AI-related positions themselves.

Practicing with an AI assistant is a low-risk, high-value way to sharpen their approach and uncover blind spots.

Why You Should Work with Your Leaders to Use This

1. Interview quality directly impacts hiring outcomes
Your best candidates will leave the interview disappointed if the interview experience feels disorganized or irrelevant. With AI, you can help managers practice crafting stronger questions, listening for thoughtful responses, and identifying alignment with team culture.

By running practice sessions with AI, HR can spot where managers need support—before the next interview even starts.

2. Coaching managers at scale is hard—AI makes it easier
You likely don’t have the bandwidth to sit in on every interview or run dozens of prep sessions. But with AI, you can provide on-demand tools, feedback loops, and even auto-generated question sets based on the job description and competencies.

This means your training efforts can scale without sacrificing quality, and your managers feel more prepared going in.

3. Prompts matter more than ever
To get great practice sessions or question sets from AI, you need to give it clear, structured instructions—this is where strong prompting comes in.

It’s not about getting fancy; it’s about being specific. Who is the candidate? What’s the role? What are we trying to evaluate?

Paul helps HR pros sharpen these prompts every week so the AI doesn’t just generate generic content, but context-aware support that truly helps.

Want to give your managers the kind of prep that actually sticks?

Start by learning how to prompt AI to simulate interview practice, build tailored question guides, or coach managers based on role-specific needs.

And if you’re not sure where to start, Paul’s got you. Reach out to him and let’s get your team prompting like pros.

Takeaways:

1. AI isn’t just for screening job candidates. It’s also a powerful tool for interview coaching.

2. HR can use AI to scale personalized support for every manager on the team.

3. Strong prompts make the difference between generic advice and truly useful feedback.

Smarter interviews start with better prep. And better prep starts with you.

📄 Prompt of the Week

Use this prompt to help your leaders become better interviewers:

ROLE: You are an AI interview coach, skilled at helping leaders prepare for interviews by simulating responses and generating follow-up questions.

REQUEST: Help me prepare for an upcoming interview by simulating the role of the interviewee based on the ###Job_Description below. Generate realistic responses, suggest follow-up questions, and provide possible answers to those follow-ups.

GOAL: The goal is to refine my interviewing skills by practicing with AI. This will allow me to tailor my questions to the role, identify strong or weak responses, and improve the overall interview process.

INSTRUCTIONS:

Step 1: Review the ###Job_Description provided.

Step 2: Ask me what my first question is. When I ask the question, you will simulate the interviewee's response based on the job requirements.

Step 3: After you provide the interviewee’s response, provide 3 possible follow-up questions that will allow me to explore responses more deeply.

Step 4: We will continue this simulation as you provide answers to my chosen follow-up questions and then new questions I ask you.

Step 5: We will conclude the simulation when I state, “Thank you for your time”.

Step 6: After the simulation concludes, you will provide me with suggestions for improving my interviewing techniques.

CONTEXT: Use the following job description to guide the simulation:

###Job_Description:

[Insert job description or relevant details here]

🤩  The Fun Side of AI

Using AI doesn’t have to be all work. Here is a fun way to interact with AI.

Let’s Have Dinner

If you could host a dinner party with your favorite fictional characters, who would they be?

Imagine Sherlock Holmes debating philosophy with Yoda.
Or Hermione Granger bonding over dessert with Tony Stark.
Now imagine you’re the one planning the menu.

Sounds silly, right? But it’s actually a great creative exercise—and a surprisingly fun way to practice storytelling, design thinking, and detail planning.

ROLE:

Act as a creative event planner and literary expert who specializes in designing immersive dinner party experiences featuring fictional characters.

REQUEST:

Help me create a themed dinner party menu and experience for a group of fictional characters, with food, drinks, and atmosphere inspired by their personalities and stories.

GOAL:

Design a unique, detailed dinner party that feels personal and imaginative—where every element fits the character guests and makes the night unforgettable.

INSTRUCTIONS:

Fictional Guest List:

My guest list includes [Harry Potter, Katniss Everdeen, Tony Stark, Sherlock Holmes, Elizabeth Bennet, Aragorn, Daenerys Targaryen, Luke Skywalker, Jay Gatsby, Mario].

Theme or Mood of the Dinner Party:

I want the evening to feel [elegant and formal, cozy and magical, rustic and earthy, high-tech and futuristic, playful and quirky].

Cuisine Style or Cultural Influence:

Build the menu around [Mediterranean, Asian fusion, Southern comfort, classic French, Middle Eastern, vegetarian, medieval fantasy, space-age fusion].

Courses to Include:

Design a menu with [appetizer, main course, side dishes, dessert, drink pairings, custom cocktails].

Location or Setting for the Dinner:

Set the party in [a grand castle hall, a rooftop garden, a cozy woodland cottage, a spaceship dining room, a jazz-age mansion].

Character Dietary Preferences or Traits:

Take into account that [some characters are vegetarian, some love sweets, some are warriors who need hearty meals, some would only eat simple or nostalgic foods].

Extra Entertainment or Story Elements:

Add fun details like [background music choices, themed table decor, character dialogue during the meal, dramatic plot twists, mystery game elements].

TONE:

Use a tone that is [imaginative, playful, elegant, theatrical, warm].

STYLE:

Use a style that is [narrative description, menu with commentary, event guide, storytelling script, character journal entries].

OUTPUT FORMAT:

- Begin with a short intro setting the scene and the guest list

- Provide a full dinner menu with names and descriptions for each course

- Add one paragraph per course explaining how it connects to specific characters

- Include extra immersive details (setting, decor, dialogue, soundtrack) to bring the event to life