In job interviews, timing isn’t everything. It’s the only thing

Most job seekers ask the right questions, just at the wrong time

Interview requests

Most candidates know it’s smart to ask questions in a job interview. Fewer realize that when you ask them can make or break your chances.

Let’s be blunt: asking self-serving questions too early—about remote work, vacation or flex time—and you risk disqualifying yourself. Why? Because it sends the wrong message. Hiring managers may assume:
“I just want to do the bare minimum.”
“I’m not a team player.”
“I’m already planning my escape.”

In Canada’s current job market, where many roles attract dozens or even hundreds of applicants, employers are looking to narrow the field quickly. You need to give them a reason to keep you in the running. Don’t eliminate yourself before you’ve even made a case.

First: prove your value

Think of your first and second interviews as sales meetings—not in the aggressive sense, but as opportunities to show how your skills, experience and mindset solve the employer’s problems and contribute to their goals.

Before you ask what the company can do for you, prove what you can do for them. That means listening carefully, asking insightful questions and positioning yourself as a solution—not a risk.

The salary exception

There’s one exception to this timing rule: salary. If you have a firm minimum, raise it professionally and early to avoid wasting anyone’s time:

“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?”

While some Canadians are hesitant to bring up pay early, it’s perfectly acceptable, especially when framed with respect and clarity. If it’s a match, continue the conversation. If not, you move on.

Ask the right questions—at the right time

Your early questions should be strategic, focusing on expectations, alignment and success in the role. Here are examples that help you stand out:

• What should I accomplish in my first 90 days?
• What challenges might I face in this role?
• How might my responsibilities evolve over time?
• What does success look like in this position?
• What skills or experience do you value most in the ideal candidate?
• Can you describe the team I’ll be working with?
• What’s the timeline for key projects this role will support?
• What am I not asking that I should be?

Each of these opens the door to demonstrate your fit—and gives you a chance to emphasize how you’ll contribute.

For example:
Q: “What challenges will I face?”
A: “We’re rolling out a new software platform called Centrix, and the team’s learning curve is steep.”
You: “I’ve used Centrix extensively at my last job.”
Or: “I helped implement a system across a regional government office in Ontario, retraining 20 staff in six weeks. I’d bring that experience here.”

That’s how you turn questions into value statements.

Make it clear: you’re a strong investment

Everything about your job search—your résumé, LinkedIn profile, networking and interview presence—should answer one question:

Why is hiring you a better decision than not hiring you at all?

Employers don’t create roles out of generosity. They’re investing in someone they believe will improve efficiency, solve problems or drive growth. If you can’t make that case early, you may not get another shot.

Final thought: timing signals priorities

Asking about perks too soon—flex hours, sick days or remote options—can undermine your credibility. Even if those things matter to you, bring them up only when you’ve shown that you’re committed to the role, the team and the company’s success.

Ask smart. Ask strategically. Ask later. Or don’t get asked back.

Nick Kossovan, a well-seasoned veteran of the corporate landscape, offers advice on searching for a job.