Interviewing with Confidence Asking Questions and Showing Interest

Questions You Should Always Ask in an Interview

Change your interview from a talk to a serious business deal. Learn 7 key questions to discover hidden problems and stop yourself from taking a 'bad apple' job.

Focus and Planning

Major Changes in Job Interview Strategy

  • 01
    Change Your Goal Stop trying to get picked and start focusing on fixing the company's problems. Think of the interview like meeting a client to figure out their business needs. Focus on the results you can deliver that will give them a good return on their investment, instead of just trying to impress them.
  • 02
    Find the Real Issues Find out what's really going on behind the polished sales pitch. Research from Columbia University (2023) shows that 90% of job seekers overestimate the full picture of what a role offers, creating a dangerous information gap. Close that gap by digging into hidden issues (like broken systems or lack of team support) and why the last person left. This helps you avoid taking on a job that is set up to fail.
  • 03
    Get Real Power Focus on having the real power to make strategic choices over just having a fancy title. Kevin Kelly, CEO of global executive search firm Heidrick & Struggles, found that 40 percent of executives hired at the senior level are pushed out, fail, or quit within 18 months. Make sure the goals for your area are important to the CEO, and confirm that you have guaranteed money and the right to make decisions. This stops you from getting burned out by having a job with lots of duties but no real control.

What Are Strategic Interview Questions?

Strategic interview questions are questions you ask an employer to uncover hidden problems, assess decision-making authority, and confirm that the role offers the resources and support needed for success. Unlike generic questions about company culture or daily tasks, strategic questions focus on business realities: budget constraints, power structures, and the real obstacles you'll face in the role.

The goal is to shift from being evaluated to evaluating. Most candidates treat interviews as a performance where they try to impress. Strategic questioning treats the interview as due diligence, where you investigate whether the job is set up for you to succeed or fail. This approach protects your career by ensuring you don't commit to a position where structural problems guarantee burnout or failure.

Checking the Job Offer

Most career advice treats job interviews like a social gathering where you ask questions just to "seem interested" or "check the office vibe." You are often told to ask about a normal day or what the boss likes best about the workplace. In a serious professional setting, this is a big risk. Treating an interview like a friendly chat keeps you unaware of the actual business problems and internal struggles of the company.

The truth about any new hire is that the employer knows much more about the job's real problems, team fights, and budget limits, while you only get a polished story. According to Leadership IQ (2005), 46% of new hires fail within 18 months, often because critical red flags were visible during interviews but went unexplored. Your questions aren't meant to make friends. They are tools to learn the hidden facts and make sure you are not "buying a bad deal." If you don't find out the hidden truth of a job, you risk a "bad start": committing your career to a position where success is impossible because of how it's set up. This lack of clarity wastes years of effort and causes you to get stuck.

This guide helps you move past just hoping a job is a good fit and gives you a clear plan to prove it. The system below will change the interview from a performance into a serious business discussion that protects your future career path.

Checklist for Interview Types

Self-Check Chart

Use this chart to see what kind of questions you are asking. Figure out which type fits how you interview now to see where you might be missing out on strategic advantages, and what simple steps you can take to improve.

What You Do

Ask general questions about the "typical day" or "company culture."

Why You Do It

You treat the interview like a polite social meeting instead of a business agreement.

What to Change

Shift from focusing on "fitting in" to doing your necessary research.

Your Type

The Surface Participant

What You Do

Only ask about goals and "What does success look like in 90 days?"

Why You Do It

You assume the path to success is clear and that just working hard is the only thing that matters.

What to Change

Check that the company’s goals match the tools and support you will be given.

Your Type

The KPI Specialist

What You Do

Ask about hidden problems, like "Why is this job open?" or "What is the biggest thing stopping us here?"

Why You Do It

You know that employers often hide structural problems or things that make the job seem bad.

What to Change

Find out about hidden problems so you know if the job is set up for you to fail.

Your Type

The Risk Auditor

What You Do

Ask about big, important issues, like "What happens if this project fails?"

Why You Do It

You know your career success depends on the company’s most urgent needs.

What to Change

Match your specific skills to the company’s most costly problems.

Your Type

The Value Closer

Smart Research: Seven Ways to Take Control in the Interview

Your Action Plan

As an executive coach, I tell you to stop seeing the interview as you performing and start seeing it as you checking things out carefully. Use these seven methods to get the upper hand.

1
Define the Win in 90 Days.

Ask: "What specific, measurable things must I achieve in my first three months so that the company sees a high Expected Return from hiring me?" This forces the interviewer to focus on the real results you need to create, not just vague job duties, ensuring your work helps the most important projects.

2
Check the Job's History.

Ask: "Why did the last person leave this job, and what is the one thing they could have done better to succeed?" Use this to solve the problem of Unequal Information, finding out if you are walking into a bad situation with hidden issues or a job with a clear path forward.

3
Find the Main Problem.

Ask: "If I started tomorrow, what is the single biggest thing that would stop me from reaching my goals?" This lets you look at the job's biggest slowdown (maybe it's lack of money, bad tools, or difficult people), which will limit how much you can actually do.

4
Map Out Who Has Power.

Ask: "Who has the final Say and Approval Power for the work I'll manage, and how do they usually judge if a project is good?" Knowing who controls the money and final sign-off stops you from being responsible for results without having the real control to make them happen. For deeper questions about team challenges, explore questions to ask about the team's biggest challenges.

5
Figure Out the Resource Shortage.

Ask: "What specific money and staff have been set aside to support the plans you mentioned today?" This helps you see the Cost of Not Having Enough; if they expect big things but haven't given the tools, they are setting you up to do low-impact work.

6
Check If You Match Company Goals.

Ask: "How does my department’s success directly help the CEO’s top three goals this year?" This reduces the Risk of Being Unimportant by making sure your job is necessary for the main mission, not just something that can be cut easily later.

7
Bring Out Hidden Doubts.

Ask: "Based on what we talked about, what is one worry you have about me being a good fit for this job that might stop us from moving forward?" By facing their Fear of Hiring the Wrong Person, you get a chance to prove those doubts wrong before the interview ends.

Becoming an Interview Investigator

To be great at interviews, you must stop seeing it as a test of your personality and start seeing it as carefully checking out the facts. Your main goal is to discover the real story behind the job description. For a complete guide on handling the final Q&A portion of an interview, see how to answer "Do you have any questions for us?"

How do I ask about red flags without sounding negative?

Frame your questions around solving problems, not finding faults. Instead of asking "What's wrong with this team?" ask: "What is the biggest challenge the person in this role will face in their first 90 days?"

This changes the focus to fixing things rather than complaining. If they say there are no problems, that in itself is a bad sign, showing they are not honest or don't understand what the job involves.

Should I ask the recruiter tough questions?

Yes. Recruiters know the real reasons hiring happens. Ask them: "Why is this job open now, and what happened to the person who was in it before?"

Their answer tells you if the company is growing (new job) or if people keep quitting (a pattern of problems). You are looking for stability, not a cycle of people leaving.

How do senior candidates avoid bad hires?

Ask: "What will my performance review focus on in one year, and is the budget currently set aside to achieve those goals?"

This reveals the company's money situation and what they expect. If their goals are huge but they don't have the money or support, it's impossible for you to succeed.

What's the best question to ask at the end of an interview?

"Based on our conversation, what's one concern you have about my fit for this role that might stop us from moving forward?" This gives you a chance to address doubts before the interview ends.

Most candidates never ask this, which means objections stay hidden. Asking it directly shows confidence and gives you control over the final impression.

How many questions should I prepare for an interview?

Prepare 5-7 strategic questions. Some may be answered during the conversation, so having backups ensures you always have thoughtful questions ready when the interviewer asks, "Do you have any questions for us?"

Prioritize questions about obstacles, decision-making authority, and success metrics. Avoid generic questions about company culture or "a typical day," which signal that you haven't done your research. For more on what NOT to ask, see what not to ask in a first interview.

The Change in Action

To manage job interviews well, you must change from asking for approval to demanding control. When you stop treating the talk like a friendly chat and start treating it like a tough negotiation, you take back charge of your career path. The tough questions reveal what the business needs and ensure you take a job where you have a real chance to win.

Focus on what matters.

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