27 “Offensive” Interview Questions That Flip the Dynamic
Stop interviewing for a job. Start auditing an opportunity. Here are the scripts to expose red flags, test leadership, and secure your leverage before you sign.
Most people walk into an interview and immediately lower their status—even the most prominent senior leaders.
They sit down, fold their hands, and enter a subservient state.
They wait to be asked questions.
They hope to be picked.
They treat the company like a benevolent benefactor and themselves like a lucky recipient.
This is a signal of weakness.
When you act subservient, the hiring manager’s brain immediately devalues you.
Humans assess social hierarchy in milliseconds.
If you signal that you are “lower” status, the interviewer categorizes you as a commodity to be bought at the lowest price, not an asset to be acquired for growth.
You must flip the dynamic.
You are not there to simply answer questions about your past.
You are there to perform due diligence on the opportunity ahead.
You are trading your most finite resources—your time, your cognitive load, and your reputation—for their equity and salary.
If you don’t audit the opportunity to the best of your ability, you are gambling with your career.
Below are 27 “offensive” questions designed to test the reality of the company, expose toxic leadership, and demonstrate that you are a peer, not a subordinate. The last 5 are borderline insane asks—but I’ve seen it all.
Forward this to inspire a friend who is interviewing this week.
Category 1: Strategic Clarity
The Goal: Determine if the ship is growing, steering, or sinking.
Too many leaders operate in a state of reactive panic. They are putting out fires and lack a coherent vision. They will never admit this to you in a standard interview.
You have to drag it out of them.
1. “If we are sitting here one year from today celebrating a massive win, what specifically did we achieve?”
This forces them to define success with metrics, not feelings.
If they give you a vague answer (“We want to grow,” “We want to disrupt”), it means they don’t know where the goalposts are.
Note: Be especially mindful if your compensation is tied to undefined performance goals.
2. “What is the one strategic threat that keeps everyone on edge that you haven’t told me about yet?”
By asking for the “threat,” you signal that you are strong enough to handle the truth. A secure leader will respect this. An insecure leader will pretend everything is perfect.
Bonus points if you can predict the threat based on your experience and help them solve it right then and there—solve their future, don’t explain your past.
3. “If this role fails, what will have been the structural cause(s)?”
Script A (Weak): “What are the challenges?”
Script B (Strong): “What is the structural cause of failure?”
“Challenges” invites them to talk about your lack of skill.
“Structural cause” forces them to audit their lack of support. This separates personal failure from organizational incompetence.
4. “How do you make decisions when you don’t have enough data?”
Executive leadership is rarely about 100% certainty; it’s about probability.
This reveals their cognitive processing style. Do they freeze (analysis paralysis)? Do they shoot from the hip (impulsive)? Or do they have a framework?
5. “What is the biggest decision you made in the last 6 months that you regret?”
You are testing for their ability to take ownership and adapt. If a leader cannot name a regret, they may suffer from ego-lock. They may blame you for their mistakes later.
6. “Who holds you accountable?”
This is the boldest question.
In toxic hierarchies, the CEO or VP is a feudal lord with no oversight. In high-performance cultures, everyone answers to a metric or a board. Watch their body language when you ask this. If they flinch, you found the ego.
Remember: Everyone wears their Sunday best during the interview process. It’s your job to expose where the dirty laundry is—so you don’t end up laying it in later.
Category 2: The Cultural Stress Test
The Goal: Understand the cost of the payroll.
Most companies sell a culture brochure that has nothing to do with reality.
They talk about “family” and “work-hard-play-hard.” These are often code words for “no boundaries” and “burnout.”
For more, see The 7 Habits of Highly Toxic Companies.
You need to bypass the HR rhetoric and identify if this environment creates high performance or just high chronic stress that degrades decision-making.
7. “Who is the most successful person here, and what specific behaviors make them successful?”
This reveals what the organization actually values versus what they say they value. If they say they value “balance,” but the most successful person is someone who replies to emails at 2:00 AM on Saturdays, believe the behavior.
You are auditing “Promotable Behavior.”
8. “When was the last time a direct report disagreed with you, and did you implement their idea?”
If a leader cannot recall a time they were wrong, you are entering a dictatorship.
In a dictatorship, you are paid to agree, not to think.
Eventually, that silence will cost you your reputation when the strategy fails. Or you challenge them and put yourself on the chopping block.
This behavior can slide in the early to mid stages of your career, but if you’re aligning your career with senior leadership, it’s no longer appropriate to simply be an order taker.
9. “What happens to high performers who have toxic traits here? Are they promoted or fired?”
Every company seems to have a “brilliant jerk.” If that person is promoted because they hit revenue targets, the company’s values are a lie. If they hesitate, it means revenue trumps respect.
Don’t be surprised by this—just know it before you sign.
10. “When was the last time you sent an email on the weekend, and did you expect a response?”
Script A (Weak): “What is the work-life balance like?” (They will give a generic answer).
Script B (Strong): “Did you expect a response?” This asks for a specific event, not a general sentiment. It forces them to confront their own habits.
Recognize that the most serious senior leaders will perform nights, weekends, holidays whether it’s healthy or not.
If that’s your prerogative, this question doesn’t apply.
However, for companies and employees that purport to value balance, it becomes more applicable to assess if they really mean it.
11. “What is the turnover rate of this specific department over the last 24 months?”
Do not accept “We have normal attrition.” Ask for the number—or listen for “We lost Carl in the spring and Roopa in July.”
If the number is high, ask “Why?”
Good leaders look in the mirror; bad leaders blame the exits.
Category 3: Trap Detection
The Goal: Ensure you aren’t walking into a “Glass Cliff.”
You need to know if you are being hired to build a future or to be the scapegoat for a past failure.
12. “What’s the real reason the last person left this role?”
Watch their eyes.
Do they give you a rehearsed HR answer (“They wanted to pursue other opportunities”), or the truth (“We misaligned on strategy”).
If they speak negatively about the predecessor, assume they will speak negatively about you when you leave.
13. “How much of the team’s recent failures do you take personal ownership of?”
You are looking for ownership.
A leader who owns the failure is usually better to work for. A leader who externalizes failure (“The market turned,” “The team wasn’t ready”) is a liability.
You cannot fix a problem your boss refuses to own.
14. “Is this role fully funded for the next 18 months, or is it dependent on a future round of financing?”
Never assume the money is in the bank.
Startups often hire “ahead of the curve” to show growth to investors. If your salary depends on a Series B that hasn’t closed yet, you aren’t an employee—you are an investor with no equity upside.
Similarly, teams within larger orgs, including F500 companies, are malleable and could be in turnaround mode or slated to get reorged or removed in an accelerated time frame.
Suss this out ahead of time to better manage expectations.
15. “What resources will I not have that I might expect to have?”
You might expect a team of thirty; they might expect you to be an individual contributor. You might expect a marketing budget; they might expect “organic growth” and 10x annual growth.
Find the gap and challenge it now, not during your first board meeting.
16. “What are the hidden blockers—the politics or bureaucracy—that will slow me down?”
Every organization has hidden blockers—people or processes that don’t appear on the org chart but control the flow of work.
Asking this shows you are a veteran who knows how corporate machinery actually works.
Category 4: Relationship Dynamics
The Goal: Establish the status quo for your relationships before Day 1.
Many relationships fail because of misaligned communication styles and unspoken boundaries.
You need to know how this person operates when the pressure is high, and you need to establish that you are here to drive results, not just “stay busy.”
17. “If I accept this role, what is the first thing you want me to stop doing that the team is currently doing?”
Inexperienced hires ask what they should start doing.
Strategic executives ask what they should stop doing. Strategy is often about what you decide to deprioritize.
This question shows you care about efficiency, not just activity.
18. “How do you prefer to be communicated with during a crisis?”
Do not guess.
Some leaders want a text message at 6:00 AM; others want a summarized email at 9:00 AM.
Asking this shows high emotional intelligence—you are preemptively managing their anxiety during the most stressful times.
This also invites a follow up like, “What constitutes a crisis?” which shifts the conversation to working conditions and how you and the team will best collaborate.
19. “What is the one quality you’ve seen in other candidates that I haven’t demonstrated to you yet?”
Every hiring manager has a hidden hesitation about you.
If you don't ask this, they will discuss that hesitation with the hiring committee after you leave—and you won't be there to defend yourself. (And you’ll likely never find out if you ask for feedback after a rejection).
By asking this now, you force the objection into the light.
You get the chance to say, "I'm glad you brought that up. Let me give you an example of how I handled that exact situation..." or “Thank you for bringing that up. I’ll assess in more detail the next few days and address your concerns directly in our next conversation. Do you have any additional hesitations?”
20. “If I asked your team to describe your leadership style in three words, what would they really say?”
Pay attention to the pause.
If they struggle to answer, they are disconnected from their team. If they give you generic buzzwords (“Visionary, Empathetic”), be skeptical.
If they give you something gritty (“Demanding, fast-paced, but fair”), they are likely telling the truth.
21. “When we inevitably disagree on a strategic decision, how do we resolve the stalemate?”
Notice the phrasing: “When,” not “If.”
Subordinates fear disagreement; strategic partners expect it.
This question establishes immediately that you intend to have a point of view and you both expect to be challenged.
You need to know how the tie is broken.
Does the leader pull rank (“Because I said so”)? Do they defer to data? Do they vote?
This reveals if they lead by consensus, decree, or debate.
22. "Why me? Specifically, what gap in your current armor do I fill?" or “What about my experience excites you the most?”
This forces the interviewer to verbally articulate your value proposition.
Psychological research shows that when someone speaks an argument out loud, they believe it more.
Make them sell you to themselves.
This is one of my favorite ice-breaker questions to CLARIFY why you’re in the room. It tells you their priorities and builds your confidence. A double whammy.
Take a look at our executive interviewing video in the Complete Job Search Course to learn more about how to apply this. (Free, no sign up required)
Bonus: The Highest-Risk, Highest-Reward
Warning: These questions are some of the most aggressive I’ve heard from senior leaders. Use them only if you have high leverage, or if you suspect the interviewer is testing your dominance.
23. “I see [Competitor] eating your market share in [Segment]. Is that a strategic concession, or did they outmaneuver you?”
This challenges their competence directly. If they get defensive, they are losing. If they say, “They outmaneuvered us, and here is how we are countering,” you have found a strong leader.
24. “You’ve been looking to fill this role for [X] months. Is the market lacking talent, or are your expectations unrealistic?”
This flips the script on “Why should we hire you?”
It forces them to admit they are struggling. It positions you as the solution to a problem they have failed to solve.
25. “I’m expensive, I challenge authority, and I don’t do ‘busy work.’ Why would you want to hire someone like me?”
This is classic “Push/Pull” psychology. By listing your “expensive” traits as negatives, you force them to chase you. You make them argue for your high price tag.
26. “Am I being hired to replace you eventually, or to support you indefinitely?”
This is an arrogant question to ask. It signals you are coming for the throne. A weak leader will hire a “supporter” because they fear you. A strong leader will hire a “successor” because they want to move up, too.
27. “I have two other offers I’m reviewing. Why should I pause those conversations to finish this process with you?”
This creates immediate scarcity.
Use this only if it is true, or if you are the best poker player in the room.
The “Mic Drop” Closer
Sometimes, the best move isn’t a question—it’s a challenge.
One female C-suite leader recently landed a multi-seven-figure deal with a hot unicorn tech company.
The negotiation was stalling, and she sensed they were afraid of her price tag.
She ended the meeting with this:
“Look, you either have the balls to take this strategy head on—or you don’t. Call me if you’re the executives you think you are.”
She got the offer the next morning.
To clarify — I did not advise this, but I simply clapped at the sheer aggression and unapologetic confidence. She absolutely crushed stereotypes and is performing incredibly well.
When your W2 is 3 million plus—the rules of the game are notably different.
Bonus: The “Unhinged” Questions From My Game Film
I review hundreds of hours of interview recordings from private clients to identify leverage points every year.
Occasionally, I hear a question that sets my nerves on fire. I’ve also spit my coffee out on multiple occasions.
These are not for the faint of heart—but they are real. I thought you’d like another sneak peek into my life.
Use these only when you are auditing a turnaround, a private equity takeover, or a Founder who has lost their way.
“Everyone knows the biggest bottleneck in this organization is you. Are you hiring me to dismantle your control, or are you hiring me to validate it?”
“I’ve looked at your C-Suite. “Mark” has been here since the beginning, but their department is continually failing. Do I have the mandate to fire your friends on Day 1?”
“Does the Board work for you, or do you work for the Board? Because I don’t take orders from a 28-year-old Private Equity associate.”
“Your last valuation was in 2021. Are we operating on reality, or is your ego still attached to a number that doesn’t exist anymore?”
“I don’t need another salary; I need a liquidity event. Do you have the stomach to sell this company in 36 months, or are you going to hold on until it dies?”
“If I walked into the CFO’s office right now and looked at the real cash position—not the board deck version—how many months of life do we actually have left?”
“To get to this valuation, where specifically have you operated in the ‘grey area’ legally or ethically that I need to know about before I put my name on the filing?”
“Who is the ‘real CEO’—the spouse, the advisor, or the investor—who actually makes the final call after the meeting ends?”
“You’ve burned $50M in three years with flat growth. Why shouldn’t we just return the remaining capital to investors and call it a day?”
“If this company disappeared tomorrow, would the market actually care, or would they just switch to [Competitor] without blinking?”
Conclusion
The goal of these questions is to shift the psychological leverage in the room.
When you ask hard-hitting questions, you stop being a candidate begging for a slot and start being a senior leader auditing an opportunity.
You signal that you have options.
You signal that you belong in the room.
You signal that you are protective of your time and talent.
Confidence is not saying “I can do this job.”
Confidence is asking “Is this job worth doing?”
Before you leave the room, there is one final bonus question you must ask. It is the catch-all that often reveals the most critical piece of information they forgot to mention.
Bonus Closer:
“We’ve covered a lot today, but what is the one question I should have asked you—but I didn’t?”
This puts the integrity of the leader on the line.
A good answer will use this opening to reveal a hidden challenge, a team dynamic, or a critical context you missed.
A bad answer will be, “No, I think we’re good.”
Listen to the answer. Then, make your decision.
Your career is your most valuable asset. Manage it accordingly.
Need help applying this? Upgrade to paid for monthly live sessions with Jacob.
Stay fearless, friends.