Questions to Ask a COO
Twenty questions for the half hour you get with a chief operating officer you do not work for: an informational call, a conference introduction, a coffee arranged by a mutual contact, or an interview where they are the hiring manager. None of them assume inside knowledge of the company, and several are about how they got the job rather than how they do it. If they are your own COO and you can act on the answers, the skip-level questions for your COO are the ones to take instead.
The questions
Open any question for the note
What does your week actually look like? Which meetings are yours to run?
Why ask it
A calendar is harder to spin than a mission statement. If most of the week is unplanned escalation, the operation is running reactively whatever the strategy deck says about it.
How would you describe what the company is trying to get right this year, in one sentence?
Why ask it
The one sentence limit is the point. A COO who needs five initiatives and four minutes is describing an organisation without a clear priority, which explains a lot of the confusion further down.
How would you explain what the company actually does, operationally, to someone outside it?
Why ask it
The version a COO gives is about flows and constraints rather than the marketing story, which is the fastest way for an outsider to get oriented. Where they simplify tells you what they treat as incidental.
What is different about how the company works now compared with two years ago?
Why ask it
Comparing then and now gets you the trajectory instead of a snapshot, and it shows which changes stuck. Vague answers often mean growth happened to the company rather than being managed.
How do decisions get made when two teams want the same resources?
Why ask it
Resource conflict is the substance of the job. Listen for a named forum or process; if it is settled case by case, seniority is deciding it and you should know whose.
What is the last process you personally redesigned, and what prompted it?
Why ask it
Asks for one artefact rather than a philosophy of improvement. The prompt is the interesting half: a customer complaint, a bad quarter, an audit finding, a resignation.
What does the company do well that does not show up in the marketing?
Why ask it
Gives them something to be proud of that they are rarely asked about, which usually opens up the rest of the conversation. It also shows an outsider where the real capability sits.
What would surprise someone joining from a company twice your size?
Why ask it
Turns a vague culture question into a concrete comparison. The answer is usually about speed, formality, or how much ground one person is expected to cover, all of which matter if you are considering the move.
Which part of the operation are you leaving alone on purpose this year?
Why ask it
A deliberate not this year shows sequencing. A COO who says everything matters is describing a place where projects begin, compete for the same people and stall.
How much of your job would be the same at any company, and how much is specific to this one?
Why ask it
Separates the craft of the role from local circumstance, which is exactly what an outsider cannot see. It also tells you how far their advice will travel to your situation.
What is the last thing you changed your mind about?
Why ask it
Reversals show whether someone updates on evidence or on pressure from whoever complained loudest. No examples from a person making dozens of calls a week means outcomes are not being tracked.
When cost, speed and quality collide, which one usually gives here?
Why ask it
Every operation has a default tiebreaker and it is rarely written down anywhere. Knowing it explains most of the decisions you have already seen and predicts the next several.
What do you look for when you hire into operations?
Why ask it
A direct route to the thing you probably want to know, asked in a way that is easy to answer generously. Listen for the qualities they name unprompted rather than the qualifications they list.
What do you look at to tell whether a manager is doing well?
Why ask it
Tells you what actually gets rewarded. If the answer is only targets, expect turnover on the teams underneath the managers who hit them.
Which of your current risks worries you most: a vendor, a single person, a compliance exposure?
Why ask it
A COO who has mapped concentration risk answers with specifics and a mitigation attached. A general answer about risk management means the register exists but nobody is working it.
What is the hardest thing about working there that you would tell a candidate straight?
Why ask it
Frames honesty as fairness to a candidate rather than disloyalty to the company, so you usually get a real answer. Whatever they name is the thing you would be signing up for.
How do you keep a sense of what the front line is dealing with?
Why ask it
Reveals whether they still visit the warehouse, listen to support calls or read tickets. The answer also gives you a usable model if you want their job one day.
What did you have to unlearn when you moved from running a function to running operations?
Why ask it
Only someone who has made that move can answer with specifics, usually about giving up the work they were best at. It is one of the better questions for a mentoring conversation.
How did you end up in operations in the first place?
Why ask it
Almost nobody plans this career, so the route is usually accidental and worth hearing. It is the easiest question here to ask a stranger and the one most likely to produce a long answer.
What should I be paying attention to that I probably am not?
Why ask it
An open close that lets them raise whatever your questions missed. In practice this is where you hear about a coming reorganisation, a systems migration or a shift in the market.
Getting Value from Time with a COO
Practical guidance for the conversation itself
Know which conversation you are in
Time with a COO arrives in a few shapes: a skip level as a newer employee, an informational conversation while you weigh a move, a mentoring half hour, or a meeting where you are the one presenting. The same question lands differently in each. In a skip level, ask how the operation runs. In an informational conversation, ask about the company's trajectory. In a mentoring conversation, ask about their own transitions. Trying all three in twenty minutes gets you shallow answers to all of them.
Ask about mechanics, not values
- Operators give detailed answers about cadence, metrics, escalation and resourcing, and slogans about culture and mission.
- Anchor a question in something specific you can see from outside: a new market, a systems change, a hiring surge, a restructure.
- Ask for one example rather than a general approach. "What did you change last quarter" outperforms "how do you approach change".
- Do not ask anything answered in the last earnings call, the annual report or the company handbook.
How much time you actually have
- Twenty minutes realistically holds three questions plus follow ups. Choose them in advance and rank them.
- Lead with your best question rather than saving it, because these meetings get cut short far more often than they run long.
- Write the numbers down during the meeting. Metrics and headcount figures are the most durable thing you will take away.
- Send a short note afterwards that references one specific answer rather than thanking them in general terms.
What the answers tell you
- Specific figures recalled from memory suggest a leader close to the operation rather than to the reporting layer above it.
- A named broken process with a stated next step is a better sign than a polished account of continuous improvement.
- If nothing has gone wrong in the past year, either the organisation has been unusually lucky or you are being handled.
- If their stated priorities do not match what your own manager tells you, understand that gap before you plan your year around either version.