The 7 Questions Every Entrepreneur Must Be Able to Absolutely Nail

As an entrepreneur, you’ll get questions about your business all the time – from friends, customers, suppliers and investors. Your answers – and how you answer them – say a lot about you as a leader, and you need to easily be able to respond with conviction, confidence and brevity.

Practice your answers. Say them out loud. Practice in front of a mirror. Think of them as job interview questions – ones that can be asked by anyone, anywhere, anytime.

Here are the 7 questions you need to absolutely nail.

For each, I’ve included example answers for my first, smaller company (TravelPost) as well as for HotelTonight.

What does your company do?

This is your elevator pitch. Explain not only what your company does but also why someone should use it.

TravelPost: We’re a hotel review site that shows you reviews from people like you to help you make more informed decisions about your travel.

HotelTonight: We’re an app for booking last-minute hotel deals that saves you time and money and makes booking a hotel way more fun.

How is it going?

You should always project optimism – even if you’ve just had the worst day ever. Combine that positive attitude with some hard facts to hit your point home.

TravelPost: We’re growing like a weed. We crossed 500,000 unique visitors last month.

HotelTonight: We’re killing it! Just hit 10 million downloads and opened our 400th city.

How many people are at your company?

People tend to be really curious about the size of your company. To project greatness, include both full-time employees and contractors. I also like to use my response to this question to highlight good news and ask for help.

TravelPost: 10 – it’s the most passionate team I’ve ever worked with. We’re looking to hire a front end developer right now – know anyone great?

HotelTonight: 130. We just brought on one of the best Rails developers I’ve ever worked with. We’re hiring like crazy in engineering and supply operations.

Do you have funding?

How much you’ve raised and who you raised it from is a yardstick of your success. If you haven’t raised much, focus on the future.

TravelPost: We’ve raised some funds from friends and family. We have all we need for now – we’ll be raising a Series A in the spring, and we have a lot of interest from investors.

HotelTonight: We’ve been fortunate enough to have raised over $80 million from some of the best travel and technology investors.

Why should I use you vs. the other guy?

This is the competitive differentiation question – and it should be a slam dunk.

TravelPost: On TripAdvisor, you’ll see hundreds of reviews for a hotel, but it’s hard to tell if a review is from a retiree in Florida or a 20-year-old in LA. We’ll show you reviews from people like you, so you can make more informed decisions. Give it a spin for your next trip – I think you’ll like it.

HotelTonight: Unlike the legacy online travel agencies, we built our company from the ground-up for mobile so our apps are a lot easier and more sleek and fun to use. Not to mention that we have better rates on better hotels. You like saving time and money, right?

How did you get the idea?

The inspiration for the company should have a personal element to it, while also describing the problem you wanted to solve.

TravelPost: I love to travel, and I’ve worked for internet companies my whole career, so I combined those interests into a business that helps people go on better trips.

HotelTonight: I’d been in online travel for 7 years with various startups, so I spotted the last-minute mobile opportunity for both consumers and hotels early. And the existing travel apps were so lame I knew we could build a significant product, brand and company.

What’s next?

Here’s your chance to get the asker excited for the future... so they’ll become a customer now.

TravelPost: We have a lot of product innovations in the works – sign up and we’ll keep you posted.

HotelTonight: It’s an amazing time for HT – we have some major announcements coming this fall, and our summer travel deals have never been better.

Any other questions/answers you think every entrepreneur should have at the ready?