The Other Side. The Selection.

A corporate interview is a process you can prepare for. There is a format: behavioral questions, case studies, panel interviews, sometimes an assessment center. There is an HR person moderating. There is a funnel with a logic to it, and at every stage you have a reasonable sense of what is expected and how you are being evaluated. You can read Glassdoor, find out what questions get asked, and rehearse your answers. Many people do exactly that, and it works.

Meeting the owner of a private business is a different thing entirely. There is no fixed format, no list of questions, no scoring matrix. The meeting might take place in his office, at a restaurant, or in his car on the way to a site visit. It might last forty minutes or four hours. The owner might fire ten questions at you in a row, or he might spend ninety minutes talking about his business and watching how you react. This is not an interview in any conventional sense. It is an introduction, at the end of which he will decide whether he wants to work with you, and that decision will be largely intuitive.

This article is about how the selection process works in private business: what the owner is actually evaluating, how to prepare, what stages the process goes through, and what mistakes candidates make most often.

What the owner is evaluating

When a corporate executive prepares for a meeting, he usually thinks about how to present his track record: which projects to highlight, what numbers to show, how to construct a career narrative. This makes sense, because in the corporate world that is exactly how it works: you are judged by what you have done, and the more compellingly you package it, the better your chances.

A private business owner has already seen your resume. If he agreed to meet you, your formal background passed the bar. Now he is asking a different question altogether, and it is not "is this person qualified enough?" but rather "is this my person?" Competencies, experience, accomplishments, everything that corporate hiring is built around, for the owner these are simply the price of admission to the meeting. The actual decision is made on a different plane, and this is precisely why corporate interview preparation does not work here: it addresses a question the owner is no longer asking.

What does "my person" mean in practice? It comes down to several things, none of which can be rehearsed.

First and foremost, the owner is interested in how you think. Not what you know, but how you reason when the answer is not obvious. He might ask about your industry, about his business, about a situation you clearly cannot know in detail, and watch how you work through it. He does not need the right answer; he needs to see how your mind works. A person who says "I don't know the specifics of your market, but the logic suggests that..." and then builds a coherent line of reasoning makes a far stronger impression than someone who confidently delivers a polished but shallow response.

Equally important to him is how you listen. Corporate executives often listen in order to respond. The owner wants to see someone who listens in order to understand. If he spends twenty minutes telling you about his business and your reply shows that you picked up not just the words but what was behind them, that creates an impression no slide deck could ever produce.

And finally, he cares about whether he is comfortable with you. This sounds subjective, and it is. The owner spends an enormous amount of time with his key people, sometimes more than with his family. He will not accept someone who is a perfect professional fit but a poor human one. He is not necessarily looking for a kindred spirit. He needs someone he can talk to without friction, without the feeling that every sentence is weighed and calculated. Executives accustomed to the corporate register sometimes lose precisely on this point: they say all the right things, but they say them as if they are addressing a board of directors, and the owner cannot picture himself discussing real problems with this person at ten o'clock at night.

There is a maxim attributed to Warren Buffett: when hiring, look for three things, integrity, intelligence, and energy, and if the person lacks the first, you had better hope they lack the other two as well. Buffett said this about public companies, but in private business, where everything revolves around personal relationships, it rings even truer. What the owner is really assessing is not your professional caliber but your human one: whether you can be trusted, whether you will play for the team or for yourself, and how you will behave when things get hard. The answers to these questions cannot be extracted from a resume or tested through a case interview. They surface in conversation, in reactions, in small things that are hard to control.

How to prepare

Preparation matters, and serious preparation at that, but it looks nothing like preparing for a corporate interview. You do not need to memorize answers to standard questions. You need to understand the business you are walking into and the person you will be talking to.

Start with the company: gather whatever is available through industry databases, company registries, press mentions, employee profiles on LinkedIn. There is not much public information on private businesses, but it is not zero, and the goal is not to become an expert in two days but to understand enough context to ask meaningful questions and not waste the owner's time on things you could have looked up yourself. At the same time, study the owner: where he comes from, how he started, what the business has been through. If you find an interview or a talk he gave, watch it, not for quotable lines but for tone: how he frames his thinking, what matters to him, what words he gravitates toward. This helps you calibrate before you walk in.

But the most underrated part of the preparation, oddly enough, is about you. You need to be able to explain briefly and clearly why you are here: not to retell your career from the first job, but to say why this particular role interests you and what specifically you can bring to this business. Owners value people who know what they want. A vague "I'm looking for an interesting challenge" does not cut it; everyone says that. But "I've spent fifteen years building operations in fast-growing companies, and I'm curious to try that in a different type of business" is a conversation worth having.

Owners are also very good at sensing the difference between someone who prepared and someone who memorized. The first asks questions that show he has been thinking about the business. The second recites figures from public sources and paraphrases the mission statement from the website. The first gets invited back. The second does not.

How the process unfolds

It almost never ends with a single meeting. The typical scenario runs from two to five meetings spread over a period of several weeks to several months. The pace is set by the owner, and trying to speed things up is usually pointless. He will make a decision when he feels ready, and arguments like "I have another offer on the table" do not accelerate the process so much as damage it.

The first meeting is a pure introduction. The owner is looking at what kind of person you are. You are looking at what kind of person he is. There is no need to try to close the deal: no need to list every accomplishment, no need to propose a transformation plan, no need to demonstrate what a strategist you are. Be yourself, listen, ask questions that genuinely interest you, and let the conversation develop naturally. The owner will generally steer the discussion where he needs it to go. If you seize the initiative and start "selling yourself," you break the dynamic he was building.

The second and subsequent meetings go deeper. The owner starts talking about the real problems: not the ones in the job description, but the ones that actually keep him up at night. He is testing how you react to the fact that the business is not as pretty as it looked from the outside. There is an important nuance here: the person who immediately starts offering solutions in response to a problem description often loses to the one who asks clarifying questions. Because the owner knows there are no quick fixes, and anyone who "figured it all out" in twenty minutes probably figured out nothing at all.

A separate stage, one that catches corporate people off guard, is the informal meeting. Dinner at a restaurant, a trip to a facility, a social event, sometimes just a long walk. The practice is old and universal: Mark Zuckerberg is known to take key candidates on walks through the woods, and Steve Jobs would court the right person for a year and a half before they agreed to join. Private business owners do the same thing, only without any grand philosophy: they simply take you out of the office into a setting where there are no professional guardrails. One owner I know always asks the candidate to pick the restaurant and then watches what they choose: are they trying to impress with an expensive place, or do they suggest somewhere practical where it is easy to talk. Another, and I have heard this story more than once, arrives at the restaurant early and asks the staff to deliberately mix up the candidate's order, because he wants to see how the person reacts to a minor annoyance they cannot control.

You can be skeptical about such tactics, but there is real logic behind them. A person who is polite to the waiter is polite to their subordinates. A person who handles a mixed-up order calmly will handle it calmly when something in the business goes sideways. A formal interview does not reveal any of this, because in a formal interview everyone is performing. The owner creates a situation where you stop being a candidate and become yourself. That is the moment that matters most to him.

Sometimes the owner will introduce you to someone from his inner circle: a partner, his wife, an old friend, a key employee. This is not a formal interview round and not a competency check; it is a screening through people he trusts. Their job is to tell him afterward what they think of you as a person. These introductions are worth taking seriously, but without trying to impress: these people are usually very good at telling the difference between genuine behavior and performance.

What not to do

Over the years, I have watched strong candidates lose good positions at a stage when everything depended on them alone. The mistakes are almost always rooted not in a lack of qualification, but in a misunderstanding of what is actually happening in these meetings.

The corporate pitch. Slides with achievements, a structured narrative in STAR format, pre-packaged case studies with numbers. All of this is appropriate in an interview with the HR department of a large company. In front of the owner, it looks like an attempt to hide behind a format. He does not want to sit through a presentation; he wants to have a conversation. If you cannot talk about your experience in plain language, without slides and rehearsed formulations, that is a red flag for him.

Trying to show you have already figured everything out. A candidate walks into the first meeting and says: "I've studied your business, I see three core problems, here's my plan." What the owner hears is: this person took two days to crack what I have been building for twenty years. The reaction is predictable, and it is not in the candidate's favor. Showing that you prepared is necessary. Showing that you already have the answers is harmful, and the line between the two is thinner than it seems.

Bringing up money in the first meeting. In the corporate world, discussing compensation early on is considered normal: why waste time if the range does not match? In private business, raising the subject of money before the owner gets to it himself is read differently. For the owner, it signals priorities: if the first thing you want to know is how much the job pays, you are here for the money, not the work. This may be an unfair interpretation, but it is a common one, and you have to account for it. Compensation gets discussed once both sides already know they want to work together. We will cover this in detail in a separate article in the series.

Passivity. The opposite mistake: the candidate shows up and waits for the owner to run the interview. To ask the questions, set the agenda, steer the conversation. Some owners do exactly that. But many take a different approach: they start with an open-ended conversation and see what you do with it. If you sit quietly for twenty minutes without asking a single question, he will conclude that you are either uninterested or have nothing to say. The questions you ask tell him as much about you as your answers do, and he knows it.

Criticizing the predecessor. Sometimes the owner baits you himself: he tells you the previous director did not work out and clearly expects a reaction. The temptation is obvious: explain how you would have done things differently and draw a contrast. But people who speak badly of those who came before them make owners uneasy. If he hired the previous executive himself, your criticism is an indirect hit on his own judgment. Better to focus on what you can do, not on what someone else failed to do.

What you should be evaluating

In the previous article, I talked about due diligence: how to assess a company before accepting an offer. Here I want to say something different: the selection process is not just the owner evaluating you, it is also you evaluating the owner. And the information you gather in these meetings is more valuable than anything you can learn from outside sources, because you are seeing the person firsthand.

Watch how he handles the conversation. Whether he interrupts. Whether he actually listens to your answers or is thinking about something else while you talk. How he reacts when you disagree on something: with curiosity or irritation. How he treats his phone during the meeting: if he takes three calls in an hour without apologizing, that is not rudeness, that is his style, and it is a style you will have to live with every day.

Pay close attention to what he says about previous executives. If everyone who came before you turned out to be "the wrong person," the problem most likely was not them. If he speaks of those who left with respect, even when the parting was difficult, that is a good sign: it means he is capable of seeing people as people, not as functions.

Consistency matters too. If in the second meeting he says things that contradict what he said in the first and does not seem to notice, that is not an accident but a pattern. The inconsistency you observe during the courtship phase will be considerably more pronounced once you are working together. The same goes for the process itself: if there are weeks of silence between meetings, if he reschedules three times, if the recruiter cannot get any feedback from him, all of this tells you what your daily working life with this person will look like. The hiring process is, in essence, a model of the future relationship, a smaller-scale replica of what is to come.

When the recruiter helps

If you are working with a recruiter, the selection stage is where they are most useful. A good recruiter will prepare you for the meeting: who the owner is, how he usually runs first conversations, what topics matter to him, what to avoid. After the meeting, they can pass along feedback the owner would never give you directly: "he liked you, but he felt you were too formal" or "he's interested, but he's not sure you can keep up with his pace." Without a recruiter you would simply never learn any of this, because the owner will not explain his reservations; he will just not call back. And the recruiter can be useful in the other direction as well: I have seen more than a few cases where an owner said "too corporate" after the first meeting, then changed his mind after a conversation with the recruiter and ended up hiring that very person.

Two processes at once

There is something candidates often overlook when they are focused on making a good impression. While the selection is ongoing, you should be gathering information for the decision you will need to make when the offer comes. Because if you reach the offer stage without having sorted out the key questions, you will face two bad options: accept the offer blindly, or start asking questions that at this point will look like either bargaining or doubt.

By the time you receive an offer, you should have a clear picture: what the real situation in the business is and what is expected of you in the first year, who else is involved in running the company, what happened to your predecessor and why. Not all of these questions can be asked directly, and not all answers will be complete, but the information needs to be collected along the way, not after the offer is on the table. An owner who is serious about hiring understands this and is willing to answer. An owner who deflects, makes jokes, or promises "we'll sort all that out later" warrants caution.

Buffett once observed that marrying someone with the intention of changing them is madness, and hiring someone with the same intention is exactly the same kind of madness. This works both ways. If during the selection process you see things in the owner that bother you and convince yourself that "it'll be different once I'm working there" or "I'll be able to influence that," you are almost certainly wrong. How the owner behaves when you ask uncomfortable questions now is the best predictor of how he will behave when you ask uncomfortable questions six months in.

In the next article, we will talk about the environment you are entering: how power works in private business, where the rules come from, why the corporate tools you are used to do not work here, and what "results" means in a world where KPIs do not exist.