Questions to Ask a Small Business Owner in an Interview
Questions to ask a small business owner in an interview, for a job candidate at a company small enough that the person hiring you also owns the place. They are grouped by the role, the business, the owner as a boss, pay and time off, and what comes next, and each has a note on what a full answer or a thin one tells you. Small companies with a few dozen staff often send a manager to the first meeting, so one more group holds questions to ask an interviewer at a small business who runs the team but does not own the firm. Nobody gets through all 54 in one meeting: pick the handful whose answers could change your mind about the job. Interviewing an owner for a class or an article instead? The business and owner groups mostly work as they stand.
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The questions
Each question, and why to ask it
The role
What does a typical day in this job look like, from the first hour to the last?
Why ask it
Ask the owner to start from when the door opens and go through to closing. You are listening for how much of the day is the work in the job title, how much is interruptions, and whether anyone stops for lunch. If no two days are alike, ask about yesterday.
Why are you hiring for this now, and what happens if the job stays empty?
Why ask it
A fuller order book, someone leaving and an owner tired of doing the invoices at night are three different jobs under one title. Whatever would break without you is what you would be judged on. If the owner cannot say what that is, ask what you would be doing in your first week.
Who did this work before me, and what happened to them?
Why ask it
The honest answers range from the owner was doing it at midnight to three people have left in two years, and both are useful. If the last person moved up or still works there, ask whether you could have ten minutes with them. A change of subject is worth one polite second try.
What would my first ninety days look like if it went well?
Why ask it
There is rarely an onboarding plan at this size, so you may watch the owner work the answer out in front of you. The milestones they settle on, such as running the till alone by week two or taking over the ordering by month three, are worth writing down. Bring them up again at your first review.
What decisions would be mine to make, and which ones come to you?
Why ask it
One owner hands over the keys and the supplier accounts in the first month, another signs off every email. Either can work if you know which you are getting. Ask for something the last person decided without checking, such as a refund, a reorder or a change to the rota.
Would I report to you directly, or to someone else day to day?
Why ask it
The owner's name may be on the contract while a manager, a foreman or the longest-serving colleague actually runs the floor. Find out whose instruction wins when the two differ. Being caught between an owner and a supervisor is hard to sort out from below.
Outside the job as advertised, what else would I be expected to pick up?
Why ask it
At this size somebody has to answer the phone, sign for deliveries and fix the printer, and it is usually whoever sits nearest. A straight list is a good sign. 'A bit of everything' with no examples means the edges of the job have not been drawn, so ask which of those extras the last person did.
How will you judge whether I am doing the job well, and how will I hear about it?
Why ask it
Few small firms have written targets, so the measure may be a number, a customer who stops complaining or simply the owner's impression. The second half matters as much: with no review cycle, criticism can go unsaid until it has grown into a bigger conversation.
Who would train me, and how much of their week can they spare?
Why ask it
Training here usually means sitting beside someone who still has a full job of their own. If that person is the owner, ask what happens to your questions in a busy week. If nobody is named, expect to teach yourself from old emails and files.
What tools and systems would I be working in?
Why ask it
It might be current software, a spreadsheet the owner built years ago, or a paper diary by the phone. None of those is a reason to walk away. Ask who fixes it when it breaks and whether you would be free to change how it is set up.
Who would I be working with most closely, and can I meet them?
Why ask it
In a team of a dozen, one difficult colleague shapes every working day, and there is no other department to move to. Ten minutes with the person at the next desk tells you things the owner cannot. If meeting anyone before an offer is refused, ask why.
What are the hours in practice, and how often does work reach people in the evening or at weekends?
Why ask it
'In practice' is the part to stress, since an owner who answers messages at ten at night may not notice that staff feel obliged to reply. Ask what the last out-of-hours request was and who dealt with it.
What is the hardest part of this job that the advert leaves out?
Why ask it
Every job has one: a difficult client, a monthly deadline, a machine only one person understands. An owner who names it plainly is treating you as someone who will find out anyway. If you are told there is no hard part, ask what the last person grumbled about.
The business
How did the business start, and how different is it now?
Why ask it
Most owners enjoy telling this, which makes it a friendly way into the questions about the company itself. Listen for what is still done the original way out of habit, because that is often where a new hire's suggestions meet resistance.
How does the business make money, and which part is growing?
Why ask it
This is what the owner thinks about all day, so expect a long answer. Listen for whether the growing part is the part you would work in. If one or two customers bring in most of the income, ask how long they have been with the business.
Who are your customers, and how do most of them find you?
Why ask it
You will either deal with these people directly or tidy up after someone who does, so the type matters: trade accounts, walk-ins, a handful of long contracts. If new work arrives mostly through the owner's own contacts, ask what would happen to sales if they stepped back.
What would you want a customer to say about this business after dealing with me?
Why ask it
Asked as 'what are your values' this gets a slogan; asked this way it gets a word, such as fast, friendly or exact. Whichever the owner reaches for first is the standard you would be held to. Ask about a time someone on the staff got it right.
Who do you lose work to, and why do customers choose you over them?
Why ask it
'Lose work to' gets a franker answer than asking about competitors in general. A quick, specific reason for being chosen, such as speed, a specialism or being local, is the thing you would be expected to protect. When the only reason is price, there may be little room in the wage budget, so weigh the pay answers with that in mind.
Why would someone choose this job over the same one at a bigger company?
Why ask it
It invites the owner to sell the place, and the pitch shows what they think they offer: variety, a say in how things are done, being known by name. Weigh that against what a larger employer near you would give. If the whole answer is 'we are like a family', ask what that looks like on a busy Friday.
How many people work here, and how has that number changed over the last two years?
Why ask it
The direction matters more than the number. A team that has gone from nine to six may be sharing out three people's work, so ask who picked up what. Growth from four to eight in a year raises a different question, which is who trains everyone.
How long do people tend to stay, and who has been here longest?
Why ask it
Turnover is rarely tracked as a figure at this size, yet the owner knows exactly who left and when. Long-serving staff suggest the place is livable. If everybody joined in the last year, ask what changed.
What is the busiest season, and what does the workload look like then?
Why ask it
Year end for a bookkeeper, December for a shop, the first warm week for a garden firm: nearly every trade has one. Ask what hours people worked in the last one and whether holiday is off limits while it lasts.
How did the business get through its last slow stretch, and what happened to staff hours?
Why ask it
This is the stability question in a form an owner can answer without opening the books. Cut hours, a hiring freeze and the owner skipping their own pay are all believable answers. The reassuring detail is that people were told early.
What did not go to plan in the past year, and what did you change afterwards?
Why ask it
A lost contract, a hire that failed, a supplier that let them down: an owner who can name one and say what is done differently now is describing a business that learns. If the answer is that nothing went wrong, leave it there and judge by the other answers.
What is the biggest challenge the business faces in the next twelve months?
Why ask it
A lease renewal, a large customer up for re-tender, a key person nearing retirement: owners carry these around and will often share one if asked directly. Follow up by asking whether this role is meant to help with it, since that changes what the job will feel like.
What are you aiming for over the next year, and where does this role fit?
Why ask it
You find out whether you are being hired to keep things running or to build something new, which are different jobs with different pressure. An owner with no aim beyond staying busy is not a bad employer, but the role is unlikely to change much.
The owner
Where do you personally spend most of your time, and what are you trying to hand off?
Why ask it
Whatever the owner wants off their plate, whether quoting, chasing late payers or the social media, tends to land on the newest person, in the job description or not. It is also your quickest route to being trusted, so ask which one they would hand over first.
How would you describe yourself as a manager, and would your staff say the same?
Why ask it
The second half makes most owners stop and think, and what follows the pause is usually closer to the truth than 'hands off'. If you do meet the team, put the same question to one of them and see whether the two versions match.
How do you like to be told when someone disagrees with you?
Why ask it
There is no HR department or second manager to appeal to, so this is the only route a disagreement has. Ask about the last time an employee changed the owner's mind. A long silence tells you how often it happens.
How do staff find out what is going on: a regular meeting, a group chat, or word of mouth?
Why ask it
Where there is no meeting, news tends to travel by whoever happens to be standing near the owner. That suits a full-timer in the same room. If you would be part time, on the road or working from home, ask how the last person in that position kept up.
When you are away or off sick, who makes the decisions?
Why ask it
If the owner is never really away, your work will wait on their phone signal. A named deputy, or a rule about what staff can approve alone, means the business can run for a week without its owner and so can you.
Does anyone in your family work in the business, and in what roles?
Why ask it
Plenty of well-run firms employ a spouse, a son or a daughter, so ask it as a plain question about who does what. What you need to know is whether you would report to a relative, or have to disagree with one, and how that has gone for other staff.
What do you enjoy most about running this business?
Why ask it
It is the owner's version of 'what do you like about working here', and it gives them a minute to talk about something other than the vacancy. An owner who brightens at the customers or the craft sets a different mood from one who mentions only being their own boss.
What kind of person does well here, and who has found it hard?
Why ask it
Owners answer from memory, so you get real people with the names removed: the one who needed more structure, the one who took over the ordering without being asked. Hold the description up against yourself honestly before an offer arrives.
How would you describe the culture here on an ordinary day?
Why ask it
'Culture' can sound like a big-company word at a firm of eight, so the ordinary-day clause steers the answer to things you can picture: whether people eat together, whether the radio is on, how the owner greets a mistake.
Asking a manager
How involved is the owner day to day, and how often would I deal with them directly?
Why ask it
In a firm of thirty the owner might sit ten feet away or call in once a month. The answer tells you whose opinion of your work will carry weight at review time. If they are in every day, ask what they still like to check themselves.
Does the owner sign off on this hire, and would I meet them before an offer?
Why ask it
A manager at a small company can often choose the person but not the salary. Knowing who has the last word tells you where a pay question should go and whether another conversation is still to come. Five minutes with the owner is worth asking for.
What made you take a job at a company this size, and what has kept you?
Why ask it
The manager across the table once sat in your chair, and can say things about working here that an owner cannot. Listen for whether the reasons are about the work and the people or about convenience. How long they have stayed is part of the answer.
When you and the owner see something differently, how does it get settled?
Why ask it
You would be working inside whatever arrangement this describes. A recent example with an ending, such as a supplier the manager was allowed to drop, points to real authority. A careful reply with no example may mean decisions get made above both of you.
How much say do you have over my hours, time off and day-to-day priorities?
Why ask it
Some managers run the rota and approve leave on the spot, while others pass every request up and wait. It tells you who to go to once you have started and how long a yes usually takes. Pay is often the one thing kept back for the owner, so raise that separately.
Pay and time off
What is the pay range for this job, and how are raises decided here?
Why ask it
With no salary bands and no annual review, the true answer is often that the owner decides when it feels right. Ask when the last person in the role got a raise and what prompted it. If a pay review is promised after a set period, ask for the date to go in the offer.
Would I be on the payroll as an employee, and will there be a written offer or contract?
Why ask it
Some small firms take people on as contractors or on a handshake, and the difference affects tax, notice and what you are entitled to. The rules depend on the country or state, so ask how it works there and see the terms in writing before you resign from anywhere else.
What benefits are in place, and are there any gaps I should plan around?
Why ask it
What an employer has to provide differs by country, state and sometimes headcount, so ask what this business offers and assume nothing: health cover, retirement contributions, sick pay, paid holiday. Some owners will say plainly what they cannot afford yet. For leave, ask how it builds up and whether unused days carry over.
How do you handle time off when there is nobody to cover the role?
Why ask it
The allowance on paper is one thing, and a week away when you are the only person who does the job is another. Ask who covered the last time someone in a one-person role took a full week, and whether they were phoned while they were gone.
How are extra hours handled: paid, time off in lieu, or expected as part of the job?
Why ask it
Each of the three is common in small firms, and the owner may never have been asked to choose. Whether overtime has to be paid depends on where you are and the kind of role, so ask how they handle it there and whether busy-season hours are counted at all.
Is there a trial or probation period, and what changes when it ends?
Why ask it
Notice, benefits and sometimes the pay itself can differ during a trial, so ask for the terms on each side of it. An owner who can say how the end of probation is decided, and by what date, has probably done this before.
Is there any room to flex the hours or work from home some of the time?
Why ask it
A small employer that cannot match a big one on salary can sometimes make it up here, since the owner can say yes without asking anyone. Find out what current staff actually do, because an arrangement nobody uses is not really on offer. In a shop, a kitchen or a workshop, ask about swapping shifts instead.
Would the business pay for a course or qualification if it helped the work?
Why ask it
There is rarely a training budget, so the true answer is case by case. Name one specific course and its rough cost and you turn a vague yes into something the owner can agree to or decline. Ask too whether you would owe it back if you left.
Looking ahead
What does growth look like for someone in this role, given the size of the company?
Why ask it
There may be no ladder to climb in a firm of ten, and a straight owner will talk about wider scope, more pay and new skills instead. Ask what the longest-serving employee does now compared with the day they started. If a management post is promised, ask who you would be managing.
If the business grows the way you hope, who would you hire next?
Why ask it
The answer shows whether help is coming for you or the next wage goes somewhere else, such as a second van or a salesperson. If the new person would report to you, ask how soon the owner thinks that is realistic. Treat it as a hope, not a promise.
What is your longer-term plan for the business, and does it involve selling or handing it over?
Why ask it
A sale, a son or daughter taking over or the owner's retirement would each change who you work for. Ask it once, lightly, and late in the conversation. Some owners have not decided and some will not tell a candidate, so take 'no plans' at face value and move on.
Is there anything in my background that makes you hesitate?
Why ask it
An owner is spending their own money on this hire and usually has one concrete doubt: a short stint somewhere, no experience with their software, a long commute. Hearing it while you are still in the room is your only chance to answer it. Let them finish before you do.
Would a trial day or a small paid task help you decide?
Why ask it
Owners often trust what they see over what they hear, and a few hours on site shows you the place with its guard down too. Whether a trial has to be paid depends on where you are, so ask how they handle it. A request for several unpaid days tells you how your time would be valued.
What are the next steps, and when will you decide?
Why ask it
With no HR calendar behind the hire, the decision can drift for weeks while the owner deals with customers. Ask for a day you can expect to hear by, and whether a call or an email is better if it passes. If you have another offer with a deadline, say so plainly here.
Interviewing at an Owner-Run Business
Practical guidance for the conversation itself
How to Approach It
Choose a Handful Before You Go In
The list is grouped so you can take one or two from each part: the role, the business, the owner, pay and time off, and what comes next, with a separate few for a manager who is not the owner. Five or six asked properly, with follow-ups, do more than fifteen read off a page. Lead with the one whose answer could change your mind.
Read What the Business Puts Out
Customer reviews, the company's own social accounts and any local press give you specifics an owner will be pleased you noticed. Mentioning one real detail, such as a new product line or a second location, does more than saying you admire the company.
Assume the Owner Is Also the HR Department
There may be no recruiter buffering the process, so your questions land directly on the person whose money is at stake. Keep them practical rather than testing, and expect blunt answers.
When the Interviewer Is a Manager
Small companies past a couple of dozen people often have a manager run the first interview, and the owner may only meet the person they intend to hire. Most of the list still works if you say 'the owner' where it says 'you', and the group headed Asking a manager covers what only an employee can tell you. Find out early who makes the final call.
Ask About Scope Before Salary Structure
Once you know what the job actually contains, pay questions become concrete rather than abstract. It also stops you negotiating against a job description that does not match reality.
Get Anything Unusual in Writing
Flexible hours, a promised review date, a title change after probation: an agreement made across a desk is easy for a busy owner to forget, with no bad faith involved. A short email after the interview setting out what was agreed is enough, and the offer itself is the place for anything about pay.
Three Short Sequences
Understanding the Business
- 1How does the business make money, and which part is growing?
- 2How many people work here, and how has that changed?
- 3What did not go to plan in the past year, and what did you change afterwards?
- 4What is your longer-term plan for the business?
Understanding the Job
- 1Why are you hiring for this now?
- 2What does a typical day in this job look like?
- 3What decisions would be mine to make?
- 4How will you judge whether I am doing the job well?
Understanding the Boss
- 1How would you describe yourself as a manager, and would your staff say the same?
- 2How do you like to be told when someone disagrees with you?
- 3When you are away or off sick, who makes the decisions?
- 4What kind of person does well here, and who has found it hard?
Common Pitfalls
Treating It Like a Corporate Interview
Questions about matrix reporting, L&D budgets or headcount planning often have no answer at this size. Ask about how things actually happen instead of which process governs them.
Skipping the Money Questions Out of Politeness
A small business can be short of cash in ways a large employer is not, and it is better to learn that before you accept than after. Asking about the range and how raises are decided is normal, not rude.
Ignoring the Owner Dependency
If every decision, client relationship and password runs through one person, your job will stall whenever they are unavailable. Ask what happens when they are on holiday.
Over-Promising Flexibility
Saying you are happy to do anything invites a job with no edges, and at a small firm there is always more to pick up. Show your range, then ask which extras the last person actually did.
Saving Every Question for the End
An interview with an owner is often a conversation with no set slot for your questions. Ask about the business while they are talking about it and about the role when the job comes up, and keep pay, time off and next steps for the close.
Signs to Slow Down
- Nobody can tell you what happened to the previous person in the role
- The pay range is not disclosed even after you ask directly
- You are not permitted to meet anyone on the team before an offer
- The job has visibly grown during the interview process
- Questions about time off get a joke rather than an answer
- Every former employee is described as the problem
- Nobody can say whether you would be an employee or a contractor
- Every decision waits for the owner, including while they are away