“Interview your bloody bosses!”

I was at a conference, speaking about the pitfalls of working at a startup. It wasn’t easy to do so, as it was a 100 + audience of startup enthusiasts, so saying that I was treading on a minefield, would be putting in lightly. In the audience, was my previous boss. We were working on something really interesting, but it required a lot more effort and capital, and so I eventually quit.

I kept glancing at him, as he had an attentive smile on his face, and quite honestly, I knew he would have a question for me. As if I didn’t have enough on my plate already! Surely, towards the end of the talk, his hand did go up, and he asked me if he could come on stage. By now, I was defending the brickbats, but much to my surprise, he came to my aid, and agreed that things can go horribly wrong while working for a startup. To avoid this, he had an impressive suggestion -

“Interview your bloody bosses!”

Now that’s a first. How many of you have actually interviewed your boss?! Until that point, neither had I. But given the circumstances, I think a startup founder should be at the receiving end from a probable hire. Startups, in most cases, are attempts at building sustainable businesses in places where other’s hadn’t thought that businesses could exist. The entrepreneurs are treading on uncharted territory, and while the idea might hold promise, there is no certainty that the startup might succeed.

So, if you’re applying to a startup, here are 5 essential questions, you must ask the founder of the company

1) What was he/she doing before this and why did they start the company?

This gives you a good idea on what they’ve put at stake. You usually hear of people who have left lucrative jobs to start up. While this isn’t a measure of whether the startup will succeed, it is a great measure of the amount of belief the founder has on the startup idea.

2) Find out how the company makes money

This is important, especially if you’re a developer, because the robustness of the startup’s business model is directly proportional to the size of your paycheck. Know the business significance of what you’re going to be working on and more importantly, see if it is a viable and scalable way to make money.

3)  Ask about the team

Find out who your peers are, and where they came from. Ideally, your interview process should get you to interact with them, but if that isn’t the case, know as much about the team you’re going to be working with. In startups, personal dynamics are very important and see if these are people you’ll get along with. Also, see if there are accomplished people in the team - sometimes, the experience of working with someone who has worked on an awesome project elsewhere, can offer you much more than what a higher salary can give you.

4) Characteristics of success and failure

Even if a company is funded, it is important to understand people’s experiences in the company. Ask them who their top employee is and who their worst employee is/was. Now ask them to describe to you their key characteristics. This is an important question, as generally asking them to describe an ideal employee, will give you a generic answer - must be hard working, must be self motivated etc etc, which isn’t very helpful. Rather than this, asking them to describe people in their company will give you a good idea of where exactly you lie in the scale of what the company values.

5) Why me?

If you’ve got all of these things sorted, ask them why they want to hire you. If it’s a cool startup, you’re probably not the only one they interviewed (be very worried if you are :D). Ask them to be brutally honest about why they want you on board. It will give you a great idea on what the company considers your strengths and you know what is expected of you, if you were to join the company.

Of course, you can ask about things like what the company culture will be like, and what is their grand vision of the company is. But I think these are 5 questions you can ask a company based on their past and present.

Have you interviewed your boss before this? Tell us what that was like.

About the Author

Raghu Mohan
Raghu is an engineering grad handles Marketing at HackerEarth. Prior to this, he was an editor at YourStory.com. When he’s not working, you can find him at the nearest music shop having a jam session.