A Job Interview for the Startup Founder

Vikas Joshi
January 24, 2018

No kidding. There is a job interview that every startup founder must go through. Although its intent is identical to other job interviews—to find the fit between the candidate and the company—there are some differences, which I will outline in a minute. What got me thinking about this topic was a conference in town last weekend, where students from many different b-schools came to present their papers on entrepreneurship and innovation. The conference organizers asked me to pick a topic that would be of interest to graduating students, and to deliver a talk.

Now, job search and placement interviews are top-of-the-mind for people in that phase of student life. Say, you want to take up a career in marketing. You might prepare for an interview with a media firm, or a consumer goods company. Maybe you want to get into investment banking. That’s a whole different game, and you might prepare to meet those bankers and answer their questions.

That’s when the thought occurred to me: What if you wanted to be on your own? Who might interview you, and how would you prepare?

If you have any familiarity with the startup action—especially in the tech world, you will think of all kinds of interviewers a founder may face: angel investors, incubator COOs, early customers, accelerator program directors, venture capitalists, strategic investors, or even bankers. You might then think of the elevator pitch, the pitch-fest presentations, the product sales pitch, and so forth, right up to the business plan presentation. Aren’t those the kinds of interviews you need to prep for?

Indeed yes, but not so soon. Even before you start answering questions from others, you have to face the most critical interviewer: the founder of your business; and that would be you!

Why is that? One possible answer, which is really simple, goes this way. When you join a company, someone from that company interviews you. They decide if you are a suitable person to join that company. Why not use the same logic for your company? Shouldn’t your company have a chance to decide if you are a suitable candidate for it? If you agree, that begs another question: Who will interview you on behalf of your company? The answer again is, of course you will. Why? Because you are the founder. So, there it is: the Startup Interview.

Humor me, by the time you read through this piece, maybe the idea of Startup Interview may not sound all that crazy to you.

What is Different about the Startup Interview?

This is one interview in which you have to ask the questions and you have to answer them as well. Answering tough interview questions is bad enough, but asking yourself tough questions is even more painful.

On a lighter note, Startup Interviews come with their pluses. For one thing, there is no suspense about the questions: You know them beforehand. There is no risk of embarrassment: No one else is looking.
Also, just like when your parachute lands after jumping off a plane, you’ll instantly know whether or not you made it. The results are immediate.

So, What Questions do I Ask Myself in the Startup Interview?

Okay, now we are talking business. The questions will vary depending on your situation and the kind of startup you want to build. I can get you started with three questions, and you can add more to the list.

1. Why do I want to start this business?

This is a soul-searching question.

Do I want to start this business because that is a cool thing to do? Or because I would like to be the boss? Or because I would like to be different?

Do I want to start this business because I am not finding a job? Or because I cannot imagine working for someone else?

Do I want to start this business because there is a great market opportunity? Or because I want to make a lot of money? Or because I want to make a difference?

There is no right answer. In fact, at some level, the answer does not matter.

The inspiration behind YouTube was that its founders were unable to share video footage of a dinner party due to e-mail attachment limitations! Your reason need not be profound or impressive.

What matters is that you know the answer. Don’t hide it from yourself.

2. How do I feel about serving customers?

Most would-be founders are badly mixed up here. To them, being on their own means they have nobody to serve. Remember, you are talking about becoming an entrepreneur, not an emperor. Your startup exists for customers.

Cynthia Montgomery of Harvard puts it beautifully: Imagine that your business vanishes from this planet. Who will miss you? If your customers won’t miss you then, why do they need you now?

You must uncover the purpose that drives you to this business. It can be as simple as saying: People staying away from home crave for home-made food. I want to build a brand for home food, delivered wherever you are. When that happens, it will really make me feel good. Or it can be something like: Ambulances take too long to reach patients in busy traffic. I want to build a motorcycle-based service that will provide bare minimum first response much faster. I will feel happy if that saves lives.

3. How do I feel about stretching myself to learn new things?

No matter how qualified you are and how skilled you are, the business will always demand more. You will encounter situations that you have not seen before. All of a sudden, someone needs to negotiate with a tough customer, put together a new marketing campaign, or hire a new key employee. And there is no one but you who has to do it. Are you ready to learn and do what it takes?

Unlike large companies, where there are plenty of resources and clear job descriptions, startups are scrappy and messy. And often the buck stops with you. That is why learning new capabilities is so vital.
There is another reason why learning really matters in startups. You can rarely have a fool-proof plan laid out in advance, and follow it to success. The startup journey is full of failed experiments. You need to learn from failures and change course quickly. The ability to learn is therefore critical.

Done with the Startup Interview. Next, how do I evaluate the candidate?
This is the trick question. You do not evaluate the candidate. Why? Because you are not evaluating yourself. You are only trying to get a sense of the fit between you and the business you wish to start. Is this business something you will enjoy? Do you look forward to building the skills and capabilities this business will demand? Do you feel this business can fulfil your dream? If the answers are yes, yes, and yes – then you know what to do next.


Far too many businesses never really take off. There is no shame in failing, but who doesn’t want to succeed? In spite of your best planning it is nearly impossible to know ahead of time the obstacles you will face. There will be tough times ahead. Those are times when your passion for the business is all you have to hang your hat on. Before you start, it will be good to ask yourself a few tough questions and see how strongly you feel committed. The Startup Interview is a tool that helps you there. That way, you will have one surprise less as you move forward.