How to Evaluate Operations Hires Before You Commit

An operations hire decides how well the rest of your company runs. A good one keeps work running reliably, and also finds where it gets stuck and fixes the process behind it. Someone who can only keep today's processes running will leave the problems where they are. That difference rarely shows on a CV, and a friendly, unstructured conversation may not reveal it either.

This guide is for founders, CEOs and operations leaders hiring an operations manager, a head of operations or a first senior operator. It covers how to define the role before you recruit, what to look for, how to test candidates on real work, and how to use the first months in the job as the final part of the evaluation.

DisclosureJake Jorgovan co-founded Alpha Apex Group, which is mentioned in this article.

Decide what "operations" means in your business

Operations covers very different jobs. A candidate who has run a warehouse and one who has run a sales team's systems can both call themselves operations managers, and comparing them against each other tells you little. Name the kind of operations you need first.

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The approach described in this article, shown as a visual guide.

Then write down where execution is breaking today. Are vendors missing dates? Is fulfillment still manual? Do teams work without seeing each other's priorities? The hire should be measured against the problems you have, which a generic job description won't name.

How your team is organized changes the profile too. Where each person owns one area end to end, you need someone who works independently with clear measures. Where work passes in stages from one team to the next, documentation and clean handoffs matter most. In small cross-functional teams that own a whole workflow, look for range and communication.

Learn enough of the job to judge the hire

I learned this one the hard way. At one point I had someone who was really a project manager trying to act as the COO of my company, and they didn't know how to build the systems we needed. The fix was on my side. I had to understand what the company actually needed from a systems standpoint. Then I built some foundational systems that were, as I said on the productize.co podcast in May 2025 (opens in a new tab), "messy and ugly and not great, but like they did the job". My next COO or operations hire worked well, because by then I knew exactly what I was looking for.

You need enough working knowledge of the function to define success, judge candidates and manage the person you hire. That includes being able to tell a strong answer from a confident one. I'd put that on one page before the first interview.

What separates a strong operations hire

Andy Mowat, writing in 2020 about his go-to-market operations team at Culture Amp, argued that operations success should be judged (opens in a new tab) "not on what you ship but the impact those projects have on the business". Among the things he saw in the people his team promoted: they anticipated issues and brought solutions, dealt well with challenge and change, and drew unprompted praise from the stakeholders they supported. That is a useful frame for a hiring panel, because it moves the conversation from how busy a candidate has been to what changed because of them.

In practice, look for:

• Systems judgment: they can see why a process fails and how to redesign it, not only how to work around it.
• Ownership without a full brief: they make progress when the documentation is thin, and they know when to ask for help. Mowat's rule for new hires is to research for at least 10 minutes before asking, but never to stay stuck for more than 20 minutes without asking.
• Clear communication across teams: they raise problems early and keep other teams informed.
• Composure when priorities change: vendors, systems and team structures move, and the work has to keep going.
• Working knowledge of your systems: if the role needs a particular CRM, ERP or project tool from the first week, test it with a task in that system. For tools you plan to teach, test the underlying skill instead.

Probe for the warning signs rather than guessing at them:

• Generic answers about processes. Ask for one process they improved: what was broken, what they changed and what happened afterwards. A candidate who can't get specific may never have owned one.
• How much they decided on their own. Ask which decisions they owned, which needed approval and when they escalated a problem. Compare that with the independence this role needs.
• Tools in place of thinking. Ask why they chose a tool or template, what else they considered and how they checked that the workflow improved. A new tool on a process nobody understands can automate the problem instead of solving it.
• Thin evidence. Use the same follow-up questions with every candidate to establish what they did, why and what changed. Note where the evidence stays unclear.

Test the work before you hire

An interview asks people to describe their work. A work test asks them to do some of it. The US Office of Personnel Management describes work sample tests (opens in a new tab) as tasks that mirror the job, and notes that applicants often see them as very fair. It also says they suit roles where candidates should have the skills on day one, which fits an experienced operations hire, and that they can take time and money to build and run.

I came to a similar view through bad finance hires. Several of them in a row didn't work out. Writing about it in a 2023 post on preparing for growth, I concluded that I should have given each of them a quick test project before ramping them up: "For tactical roles like this, test their work before you make the hire."

The interview still matters, as long as it is structured. A 2022 reanalysis of personnel selection research (opens in a new tab) in the Journal of Applied Psychology concluded that earlier estimates had substantially overstated how well many hiring methods predict job performance. In the revised estimates, structured interviews came out as the top-ranked method. The five steps below combine a work test with a structured interview.

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Selected mean validity estimates from the 2022 reanalysis, reproduced in Sackett and colleagues’ 2023 follow-up: structured interviews 0.42, work samples 0.33, and unstructured interviews 0.19. These are corrected correlations with job performance, not percentages of candidates a method predicts correctly. Validity varies across settings.doi.org (opens in a new tab)

1. 1

   Ask two or three questions on the application

   Paul David Mather, an operations adviser who has hired for startup operations roles, prefers a short application form (opens in a new tab) to a CV alone, with questions such as "Give an example of a time you faced a major operational challenge." The answers show how someone thinks before you spend time on a call.

2. 2

   Set a short assignment built from your own work

   Mather's example for an operations manager combines 30 minutes of spreadsheet problems based on the company's order patterns, 15 minutes to prepare a five-minute pitch, and a five-minute Q&A on the pitch. He suggests one to two hours is enough, and warns that a longer assessment will probably put applicants off. Use your own data, with the confidential details removed, so the task reflects your business.

3. 3

   Ask for a critique of a real workflow

   Share one of your processes as it runs today, warts and all, and ask where it would break as volume grows, what they would change first and how they would measure the change. The answer shows how they think about a system they didn't build.

4. 4

   Run a structured interview

   Ask every candidate the same questions, with the same follow-ups, and rate the answers against criteria agreed in advance. The US Office of Personnel Management says interviews with more structure (opens in a new tab) show higher validity and better agreement between interviewers, and that questions about past behavior have shown higher validity for complex professional and managerial work. The general manager interview guide sets out a fuller structured interview process.

5. 5

   Offer finalists a paid project or a contract-to-hire period

   For a finalist you are still unsure about, a scoped project with real stakeholders, paid at a fair rate, shows how they work with your teams, unclear boundaries and live systems. A contract-to-hire arrangement extends the same test over a longer period. Fix the length and the terms in writing before it starts, and agree in advance what the project must deliver and how you will judge it, and accept that some strong candidates in secure jobs will not leave them for a contract.

Each step should test something on the one-page brief. If a step doesn't, drop it: a long process costs you candidates as well as time.

Interview questions that show how they think

These questions ask for specific past work, which gives you something to probe. The fourth adapts one Andy Mowat uses in his own interviews. Follow each answer with "what did you do next?" and "how did you know it worked?"

Agree the criteria, then debrief

Choose the criteria from the one-page brief: the systems judgment, technical skills and ways of working this role needs. Initiative, clarity of thinking, communication, adaptability and ownership are a reasonable start. Before meeting candidates, write down what a weak, an acceptable and a strong answer would show for each one.

For example, when the test is diagnosing a broken workflow, a weak answer names symptoms without looking for causes. An acceptable answer identifies a likely cause and a way to check it. A strong answer also weighs the trade-offs, names who needs to be involved and proposes how to measure the improvement. Adapt the example to your role.

OPM notes that in a structured interview each panel member usually rates the answers individually, and the panel then discusses significant differences. Ask everyone to record a rating, and the evidence behind it, before the debrief. That reduces the chance that one confident voice decides the outcome. Agree in advance which criteria are essential, and record missing evidence separately from a weakness the candidate showed.

Treat the first 90 days as the last check

The evaluation doesn't end with the offer. You see the full picture only once the person is working inside your systems with your team.

The success criteria you wrote in the brief become the plan. On my podcast in 2020 I described the 90-day criteria I set for a new hire, giving the example of someone who should, by the end of 90 days, be completely owning the operations for one segment of the business. In the same episode I described a staged hand-over: the new hire shadows someone and learns the processes, then does the work with oversight, then works alone with weekly check-ins, and finally reports the metrics each week.

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The staged handover Jake described on his podcast. The article uses a 90-day ownership goal for one segment of the business.

In the first few weeks, watch for three things:

• Where they create momentum and where work stalls. Are they removing friction or adding steps?
• How they handle what is unclear. Do they find problems without being told, and ask the right questions to get unstuck?
• What their colleagues say without being asked. Mowat counted unprompted praise from stakeholders among the signs of a successful operations teammate.

If the 90-day criteria are slipping, say so early and agree what changes. Sometimes the problem is the hire. Sometimes it is a role or a brief that was never clear, and that is worth knowing before you hire again.