The reason is simple. Founders and managers often don't know exactly what they need. They hire someone with "ops" or "HR" in their title, assume the role will define itself, and end up with a person doing a lot of work but not solving the actual problems. Two years later, the company is still missing the same things it was missing before.

This article gives you a question bank for hiring operations roles (operations manager, chief of staff, business operations) and people roles (first HR hire, people partner, head of people). Both functions share a common DNA: they're enablers. They make everyone else more effective. The interviews should test for that.

Before the questions: what these roles actually need

Three traits matter more than any specific functional experience.

Systems thinking. Strong ops and people hires see organizations as systems. They notice patterns, identify the upstream causes of recurring problems, and design solutions that hold up over time. Weak hires fix individual issues without seeing the structure underneath.

Pragmatic prioritization. These functions are infinite. The list of useful things to do is always longer than the time available. Candidates who can describe how they pick what matters consistently outperform candidates who try to do everything.

Comfort with ambiguity. Ops and people roles, especially at small companies, rarely come with a clear remit. The role is whatever the company most needs. Strong candidates thrive in that. Weak candidates wait for someone to tell them what to do.

The questions below test for these.

Questions about past work

These are the highest-signal questions. The goal is to push past the title on the resume and into what the candidate actually did.

Walk me through the most impactful project you've owned. What did you specifically do, and what was the outcome?
Tell me about a problem you identified that nobody else had noticed. What did you do about it?
Describe a time you had to build something from scratch with no template to copy from.
Walk me through a project that didn't work. What happened, and what did you learn?

What to listen for: Specificity. Strong candidates describe the actual problem, the constraints, what they did, and how they measured success. Weak candidates describe activity ("I ran weekly all-hands") without articulating outcomes ("which surfaced X recurring issues and led to Y change").

Follow-up that tends to surface the real signal: "What would have happened if you hadn't done this work? Would someone else have done it?"

Questions about prioritization

Operations and people roles are infinite. Test how candidates think about what to do.

Tell me about a time you said no to a request from someone senior. How did you handle it?
Walk me through how you decide what to work on in a given week.
Describe a time you stopped doing something that was working fine, in order to do something more important.
If you joined our team next month, what would you want to spend your first 30 days understanding before you committed to a roadmap?

What to listen for: Whether they have a framework for prioritization. Strong candidates can articulate how they trade off competing requests. They know what their function is for and what falls outside it. Weak candidates either describe doing everything or describe doing only what they're told.

The last question is especially useful for senior roles. Strong candidates resist diving into delivery before they understand the context. Weak candidates start planning before they understand the problem.

Questions about systems thinking

These test whether the candidate sees patterns or just sees tasks.

Tell me about a recurring problem you noticed and what you did about the underlying cause.
Describe a process you've built. Why did you build it that way?
Walk me through how you'd diagnose why a team is missing its goals.
Tell me about a time you saw a small issue and traced it back to something bigger.

What to listen for: Whether they think upstream. Strong ops and people hires don't just solve the immediate issue, they ask why it happened and whether the same kind of issue will happen again. Weak hires fix things one at a time forever.

Operations-specific questions

Apply these for ops manager, chief of staff, biz ops, and similar roles.

Operating cadence and rhythms

Walk me through the operating rhythm you'd want to build for a 50-person company. What rituals would you put in place and why?
Tell me about a planning process you've owned. What did you change about it, and what was the result?
Describe how you'd set up reporting for a team that doesn't currently have any.

What to listen for: Practical experience and judgment. Strong ops candidates have actually run planning cycles, built dashboards, and designed operating rhythms. They can describe what worked and what didn't. Weak candidates speak in abstractions.

Cross-functional work

Tell me about a time you partnered with finance, legal, or another function on a project. How did the collaboration work?
Describe a time you had to align a team or function around a decision they weren't excited about.
Walk me through how you build trust with senior leaders who didn't hire you.

What to listen for: Political intelligence and influence without authority. Strong ops candidates can navigate political dynamics, build coalitions, and get things done across functions. Weak ones either avoid politics or get caught up in them.

Tools and execution

What tools do you reach for when you're trying to understand a part of the business you're new to?
Walk me through a spreadsheet or analysis you've built that drove a real decision.
How do you balance building scalable systems versus shipping quickly?

What to listen for: Practical capability. Strong ops candidates are comfortable in spreadsheets, dashboards, project trackers, and the actual tools where work gets done. Weak candidates stay at the conceptual level.

People and HR-specific questions

Apply these for first HR hire, people partner, head of people, and similar roles.

Building the people function from scratch

If you joined a 40-person company with no formal HR function, what would you build first and why?
Tell me about a time you had to introduce a new process at a company that was skeptical of process. How did you handle it?
Walk me through how you'd build a hiring process for a function you don't know well.
Describe how you balance compliance work with strategic people work.

What to listen for: Pragmatism. Strong first HR hires don't try to build the policies of a 500-person company on a 40-person team. They prioritize what matters most for the current stage. Weak first HR hires over-engineer for a stage the company isn't at.

Manager development and culture

Walk me through how you've coached a struggling manager.
Tell me about a time you had to push back on a leader about how they were treating their team.
Describe how you've helped a company maintain culture through rapid hiring.

What to listen for: Confidence and clarity. Strong people leaders coach managers directly and aren't afraid to push back on senior leaders. Weak ones smooth things over or stay neutral when they should be taking a stand.

Difficult conversations

Tell me about the hardest people decision you've helped a manager make.
Walk me through a performance management situation you owned. How did it resolve?
Describe a time you handled a sensitive employee relations issue. What was your approach?

What to listen for: Clear thinking under pressure. Strong people leaders can describe the structure of difficult situations: what was at stake, what they did, what the outcome was. They don't hide behind HR jargon or generalities. Weak ones speak in euphemisms.

Compensation and structure

Walk me through how you'd think about building a compensation structure for a 50-person company.
Tell me about a time you advised a leader on a comp decision. How did it go?
Describe how you'd handle a pay equity issue you discovered after the fact.

What to listen for: Comfort with numbers and judgment under ambiguity. Comp work is technical but also political. Strong people leaders can handle both.

Practical exercises worth running

For senior ops or people hires, a written exercise produces high-signal output.

Diagnostic exercise. Send the candidate real (anonymized) data from your company: a team's OKRs, last quarter's planning output, a sample of all-hands feedback. Ask them to spend 60 minutes diagnosing what they see and writing a one-page memo of recommendations. Then review their thinking together.

Planning exercise. Ask the candidate to draft a 90-day plan for their first three months in the role. What would they prioritize, how would they spend their time, what would success look like at the end?

Difficult conversation exercise. For people roles especially, role-play a difficult conversation: coaching an underperforming manager, addressing a comp inequity, handling an employee relations situation. Tests how the candidate actually behaves under realistic pressure.

The diagnostic exercise is especially good because it surfaces the gap between candidates who can talk about ops/people work and candidates who can actually do it.

Red flags to watch for

A few patterns to watch for.

Activity language without outcome language. Candidates who describe their work in terms of meetings held, documents written, and processes implemented, without articulating what changed as a result, are usually weak in these roles.

Allergy to politics. Some candidates frame organizational politics as something they "stay out of." This is usually code for inability to navigate them. Strong candidates engage with politics directly.

Bureaucracy instinct. Candidates who reach for policy and process as the answer to every problem tend to over-engineer. Strong ops and people hires know when not to build process.

Insufficient business context. Candidates who can't connect their work to commercial outcomes ("how does HR contribute to revenue?") tend to operate disconnected from the business.

Risk aversion that masks low judgment. Some candidates frame caution as professional discipline. Strong people and ops hires take judgment-based risks. Weak ones default to playing it safe and slow.

Build your interview guide

These roles are too consequential to interview inconsistently. Use the same questions for every candidate, score with a rubric, and debrief structurally.

Build your free interview guide with Oryx

Previously in this series: Interview Questions for Customer Success and Support
Next in this series: Interview Questions to Assess Culture Fit (Without Bias)