6 Interview Questions to Ask Candidates When Hiring
Updated: Oct 12
Hiring the right candidate is one of the biggest challenges for any business. The resume may look perfect, but how do you know if the person behind the paper is a good fit for your company? Interviews are key to getting to know candidates on a deeper level, but structuring them effectively can make all the difference.
In this post, we’ll walk you through the challenges of interviewing and provide six must-ask questions that will help you uncover whether a candidate is the right fit for your role.
Why Is Interviewing Candidates So Difficult?
Interviews provide limited time to determine whether someone's experience, working style, expectations, and abilities align with the position.
And sometimes, getting candidates to the interview is a challenge in itself.
At Digital Executive, we've experienced interview show rates of approximately 50% during certain hiring processes.
That means businesses may need to account for cancellations and no-shows when building their candidate pipeline rather than assuming every scheduled interview will happen.
But getting someone onto the call is only the beginning.
Once the interview starts, you need a structure that helps you learn as much as possible without turning the conversation into an interrogation.
How Should You Structure a Candidate Interview?
Start by briefly explaining the company and position, then use a consistent set of core questions to evaluate each candidate.
At the beginning of the interview:
Introduce yourself.
Explain what the company does.
Provide additional context about the position.
Clarify important day-to-day responsibilities.
Mention relevant expectations that may not have been obvious from the job description.
Then consider doing something slightly different:
Ask the candidate what questions they have for you before you begin asking yours.
Candidates usually expect this at the end of an interview.
Moving it to the beginning can reveal what they researched beforehand and what matters most to them.
Did they research the company?
Do they understand the position?
Are they curious about the team?
Do they ask about expectations?
Their questions can sometimes tell you almost as much as their answers.
Once that's finished, move into your structured interview questions.
1. How Would You Handle This Situation?
Scenario-based questions can reveal how a candidate approaches unfamiliar problems when the answer isn't immediately obvious.
Create a realistic problem that requires the candidate to think through a solution.
For example:
“Your boss is supposed to fly out of France on Wednesday, but their flight is canceled and flights from the area aren't expected to resume until Friday. They need to be back in the U.S. by Thursday for an important event. What would you do?”
Don't focus solely on whether they arrive at the same answer you would.
Instead, listen to their process.
Do they look for another airport?
Could they take a train to another city?
Do they investigate alternative routes?
What information would they need before making a decision?
Do they give up when the obvious solution disappears?
You're evaluating how they approach the problem—not whether they guess your preferred answer.
For positions requiring independence and problem-solving, this can be particularly valuable.
2. What Do You Think Your Day-to-Day Would Look Like in This Position?
This question helps you understand whether the candidate actually understands the role they're interviewing for.
Someone who has carefully reviewed the job description should be able to explain the core responsibilities in their own words.
Listen for whether they understand:
The primary responsibilities
The purpose of the role
Who they may work with
What they would be responsible for producing
How their work contributes to the business
If their expectations are completely different from yours, that's important to discover before making an offer.
It also gives you an opportunity to correct misunderstandings.
3. Why Did You Apply for This Position?
A candidate's answer can help reveal what attracted them to the opportunity and what they're hoping to find in their next role.
Don't expect every candidate to give you an inspirational story about why your company is their lifelong dream.
That's usually unrealistic.
Instead, listen for alignment.
Maybe they're interested in the responsibilities.
Maybe the position is a logical next step in their career.
Maybe they want greater ownership.
Maybe they're interested in the industry.
Maybe the working environment matches what they're looking for.
It's also reasonable for someone to want to leave an unsatisfying job.
The important question is:
Are they moving toward something they genuinely want—or simply applying to anything that allows them to leave their current situation?
4. Tell Me About a Time You Solved a Problem Before It Became a Bigger Issue.
Behavioral questions like this can help reveal whether a candidate proactively identifies and solves problems.
Ask for a real example.
Then dig deeper.
What was happening?
How did they notice the problem?
What did they do?
Did they need approval?
What happened afterward?
A candidate's first answer may be relatively surface-level.
Follow-up questions are often where the useful information appears.
You're looking for evidence that the candidate can recognize problems and take appropriate action rather than simply waiting to be told what to do.
5. How Do You Stay Organized?
This question helps you understand the candidate's actual system for managing responsibilities, deadlines, and competing priorities.
Avoid accepting an answer like:
“I'm a very organized person.”
Ask them to show you how.
Do they use:
A task-management system?
A calendar?
Asana?
Notion?
A written to-do list?
CRM reminders?
Time blocking?
Another system?
One of the most memorable answers we've received came from a candidate who offered to screen-share their customized Asana setup.
They weren't simply telling us they were organized.
They could demonstrate the system they used to stay organized.
That's much stronger evidence.
6. What Type of Working Environment Helps You Perform Your Best?
This question can help you evaluate working-style alignment without relying on someone's hobbies or personality as a proxy for “culture fit.”
Ask about the environment where they've performed well in the past.
Do they prefer clear processes or greater autonomy?
How frequently do they like receiving feedback?
How do they communicate when they're stuck?
How comfortable are they making decisions independently?
How do they manage competing priorities?
If the position has specific scheduling requirements—such as evenings or weekends—ask about availability directly.
For example:
“This position requires availability from 10 a.m. to 6 p.m. Eastern and occasional Saturdays. Are you consistently available during those hours?”
That's much more useful than trying to infer availability based on what someone likes to do outside of work.
What Makes a Good Interview Question?
A good interview question should help you evaluate something that's actually relevant to success in the position.
Before adding a question to your interview, ask:
What am I trying to learn from this?
Scenario questions can evaluate problem-solving.
Behavioral questions can uncover evidence from previous experience.
Role-specific questions can test knowledge.
Questions about organization can reveal systems and habits.
Questions about working style can help determine whether the candidate fits the environment you're actually hiring them into.
Avoid questions simply because they're popular interview questions.
Every question should have a purpose.
Should You Ask Every Candidate the Same Interview Questions?
Using the same core questions for candidates interviewing for the same position can make comparisons more consistent.
You can—and should—ask relevant follow-up questions based on someone's answers.
But having a standard set of core questions gives you a common framework.
Instead of finishing five interviews and thinking:
“I liked candidate #3 the most.”
You can compare how each person responded to the same competencies:
Problem-solving
Preparation
Motivation
Initiative
Organization
Working style
That creates a more structured hiring decision.
What Should You Look for During a Candidate Interview?
The goal of an interview isn't to find someone who gives you perfect answers.
It's to gather evidence.
Can they solve problems?
Do they understand the position?
Why do they want the job?
Can they provide real examples of taking initiative?
Do they have systems for staying organized?
Does their working style align with the actual requirements of the role?
Hiring will never become an exact science.
A candidate can have an impressive resume, interview well, and still not work out.
But a structured process gives you more useful information before you make that decision.
How Does Digital Executive Interview Remote Candidates?
Digital Executive helps U.S. businesses source and vet remote professionals in Latin America.
Interviews are one part of that process.
Depending on the position, candidates may also be evaluated based on their work history, English proficiency, role-specific experience, technical skills, and other requirements established by the client.
After interviewing thousands of candidates, one lesson has remained consistent:
Don't use an interview simply to decide whether you like someone. Use it to gather evidence that they can succeed in the role you're hiring them to perform.
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