5 Key Questions to Ask Your Next Operations Hire

1. “Can you tell me about a time you had to create or implement systems and procedures at work to help things run smoother or more efficiently? Walk me through it in detail.”

Why ask this?
Operations professionals should be systems-minded. While attention to detail is critical, the ability to build and improve systems is what separates good candidates from great ones. Detail skills matter — combining them with strategic thinking is even better.

What to listen for:

• Specific examples — Vague or generic answers signal inexperience.
• Ownership — What was their role vs. the team’s role? Be cautious of candidates presenting others’ work as their own.
• Problem-solving process — What was the challenge, and what solution did they create?
• Implementation and adjustments — How did they roll it out? Did they adapt based on feedback?
• Documentation — Did they create SOPs, checklists, or training tools to support the system’s use by others?
• Impact awareness — Do they understand how the system improved the business (e.g., saved time, reduced errors, improved client experience)?
• Sustainability — Was the system adopted by others and used consistently over time?

2. “Which brings you the most energy – starting projects or finishing them?”

Why ask this?
Business owners are often visionary starters who need a counterpart who can bring ideas to the finish line. This question reveals how the candidate complements that dynamic.

What to listen for:

• Clear self-awareness and a rationale behind their preference.
• Real examples of project-based work.
• “Both” is not an acceptable answer — ask them to prioritize one as their primary strength.

3. “This role will involve juggling multiple projects at once. How do you keep yourself organized and ensure nothing slips through the cracks?”

Why ask this?
Multitasking and prioritization are critical in administrative roles. You’re looking for systems and habits that help them manage competing demands effectively.

What to listen for:

• Daily structure and tools (digital planners, project management software, calendars).
• How they set priorities and manage time.
• Whether they are proactive or reactive. Can they anticipate problems or pivot when plans change?

Follow-up:

“What happens when your day gets thrown off completely? How do you adjust?”
Look for adaptability, resourcefulness, and calmness under pressure.

4. “This position will evolve over time and may include tasks outside a traditional job description—sometimes even personal assistant-type work. How do you feel about wearing multiple hats and filling in as needed?”

Why ask this?
Great administrative professionals are service-driven. You want someone who is flexible and eager to support — no task is too big or too small.

What to listen for:

• Tone and attitude — Do they light up or hesitate?
• A genuine service mindset — Do they enjoy helping?
• Real examples of past adaptability or willingness to jump into new responsibilities.

5. “What’s one area you’re currently working to improve in your career?”

Why ask this?
This question reveals if the candidate has a growth mindset. Are they curious, self-aware, and working to elevate their skills?

What to listen for:

• A specific, recent area of improvement.
• A clear plan and timeline — how they’re actively working on it.
• Why this growth area matters to them.

Bonus Follow-Up Question:

“What would you do differently next time?”

Why ask this?
Follow-up questions like this often uncover the real person who will show up on day one. Your job is to uncover true behaviors, habits, and decision-making patterns through a thoughtful, layered interview process.

What to listen for:

• Willingness to reflect.
• Accountability for outcomes.
• A growth mindset rooted in continuous improvement.
• Passion for the kind of challenges your role presents.