The Timing of Your Questions During an Interview Is Everything!
- Nick Kossovan
- D.O.C Supplements - Trending News
- The Art of Finding Work
- May 2, 2025

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Most interviewers appreciate candidates who come prepared with thoughtful questions. However, while your questions are important, the strategic timing of when you ask them is more crucial.
You’ve likely heard, “Timing is everything.” This is especially true in interviews. Asking about work-life balance too early—during the initial (introductory) or second interview—can lead to elimination. Sure, work-life balance matters, but raising it early screams: “I just want to do the bare minimum!” “I’m not a team player!” “I’m already planning my escape.”
As a job seeker, understand that the hiring process is inherently a process of elimination, necessitated by many candidates vying for one role. Therefore, before you ask questions that answer, “Will this job serve my self-interests?” first, focus on establishing stickiness—a connection and trust. By demonstrating your awareness of the employer’s needs, something candidates you’re competing against are unlikely to exhibit; you increase the odds of your interviewer envisioning you as the ideal candidate for the role and the company.
Also, keep in mind that an interview is a sales meeting. Your initial and second interviews should revolve around selling yourself. Emphasizing the value you can bring—how you’ll generate revenue, solve problems, increase savings—distinguishes you from candidates more focused on WIIFM (What’s in it for me?).
The exception is the “money question.” Ideally, you should know the salary range for the position. I always ask within the first five minutes of an initial interview, “To ensure we’re not wasting each other’s time, I’m looking for an annual salary of $X. Is that within the range for this position?” There’s no point in pursuing a job that won’t meet your compensation requirements. Save everything else for later, as those details are often negotiable.
During your first and second interviews, ask:
Discovery questions:
- What’s the most important thing I should accomplish in my first 90 days?
- What challenges might I face in this position?
- Will my responsibilities change in the next six months to a year?
- Can you tell me about the team I’ll be working with and my direct reports?
Clarification questions:
- Can you elaborate on the day-to-day responsibilities of this role?
- What specific skills or experiences are you looking for in the ideal candidate?
- Please clarify the reporting structure for this position.
- What’s the timeline for the expected projects or initiatives this role will be involved with?
Closing questions:
- What am I not asking you that I should?
- What is essential for success in this role and at [company]?
- How is performance in this role measured and evaluated?
- Is there anything valuable for me to understand about the role or [company] role that we haven’t discussed?
Regarding closing questions, the purpose of asking such questions is to create a selling opportunity to emphasize that you have the skills, experience, and confidence, a critical aspect of interview success that jobseekers underestimate, to do the job. If you don’t believe in yourself, then why should your interviewer?
For instance, if you ask, “What are the biggest challenges I will face in this position?” and your interviewer answers, “Rimway is currently implementing a new company-wide software program called GLaDOS, which will greatly enhance our ability to interface with our customers and inventory; therefore, Rimway employees are in a steep learning curve.” You can respond in one of two ways:
- That you’re familiar with GLaDOS, having used it extensively while working at [company], this would be the ideal answer, or
- Recount a STAR (Situation, Task, Action, and Result) story in which you were successfully part of an implementation, be it new software, change in process, new government regulations, etc., to demonstrate (sell) your ability to adapt to changes and learn new technology, processes, regulations, a mindset not everyone has.
During your first and second interviews, focus your questions on the company, its people, and how the role contributes to its overall success. More than ever, your entire job search, not just when you’re interviewing, but your resume, LinkedIn profile, and how you present yourself during a networking opportunity, needs to clearly (keyword) demonstrate—this is where your quantifying results and achievement numbers (revenue, savings, time, amount, size, percentage) come in—how hiring you will add value.
An interview is your chance—never easy to obtain—to demonstrate (read: sell) what you can do for an employer. As the job seeker, you’re trying to land the job, not vice versa. (In today’s job market, an employer will have many viable candidates per position. You’re not an employer’s only option.) More than ever, especially as employers are understandably increasingly running their business on lean, a job exists because the employer believes that by creating the job and having it occupied by the right person (key), they’ll make more money than by not having it.
Strategically timing your questions is a crucial factor in achieving interview success. Asking about benefits, flex hours, vacation, sick days, professional development offered or “Can I work from home?” (despite the job posting stating the job is on-site) too early in the interview stage is perceived as an indication that you’re focused on what the employer can do for you, not on what you can do for the employer.
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Nick Kossovan, a well-seasoned corporate veteran, offers “unsweetened” job search advice. Send Nick your job search questions to artoffindingwork@gmail.com.