Master tough interview questions with 3 simple ideas

Master tough interview questions with 3 simple ideas

If you’re ever again going to walk into an important and tough, challenging interview, you should listen to the story of how three nutcases (aka the Close founding team) made it through the worlds’ most prestigious startup accelerator interview.

Challenging interviews are set up to catch you off guard. Interviewers want to see how you do when things don’t go as planned, or they just want the interview to take a turn that’s not in your interest.

What’s the most important thing you can do to prepare for a challenging interview?

Decide in advance what the most important thing is you want them to remember about you!

More specifically: what are the three most important things you want them to remember about you?

Just three.

Not four, not five, not ten. More isn't always better.

There are probably many awesome things you would like them to remember about you. But it’s better to choose the three most powerful ones.


Think of it as a chain that is only as strong as its weakest link.

Make these things memorable, and repeat them several times throughout your interview. You want them to stick in the interviewers’ minds.

Our Y Combinator interview

When we applied for Y Combinator, we actually didn’t apply with Close or ElasticSales. At that time we were building a very different startup: Swipegood.

Swipegood allowed you to sign up with your credit card, and then round every payment you made up the next full dollar. So $19,95 got rounded up into $20, and you made a $0,05 donation. At the end of each month, the accumulated roundups would be donated to a charity of your choice.

We decided in advance that we wanted the YC partners who interviewed us to remember these three facts about us:

  1. We were growing 20% week over week since launch day.
  2. We’d learned that the average roundup amount per consumer is $20 per month. Charging a 5% fee, we could make $1 and give $19 to charities every month for every user.
  3. We had our first successful distribution channel already. We had partnered with five charities, created a custom landing page for them, and they would send tens of thousands of their members to our page, telling them to sign up with Swipegood so they would donate to their respective charities. We saw an average 20% conversion rate on that traffic.

There were many more things we wanted them to know about us but we knew we had to be disciplined. We knew these were the things that would make the strongest impact, and we wanted to maximize their effectiveness.

Make this your doctrine

We were prepared to answer any question the interviewer would throw at us with these three facts.

This is the important point.

Most people feel obligated to answer questions in the way the interviewer intended them to be answered. But in an interview situation, you have to be able to still control the direction and focus of the conversation on the things you want them to know about you.

Example 1: The challenging question

What if the interview had asked us, “Well, I don’t think charities are really the right vehicle for change. They’re usually, at best, inefficient and wasteful, and at worst cause more harm than good. Do you really think they should be getting more support?”

We could have directly answered such a question, and gotten involved in a philosophical discussion about the validity of charities per se. We could have pointed out great examples of charities that were wonderful agents of change for the better.

But would that really have furthered our cause?

If a person holds such a view about charities, what do you think the chances are of you being able to change their opinion during the course of a short discussion in an interview? How often have you actually changed another person’s opinion about a topic the other person felt strongly about during the course of a discussion?

Instead, we stayed focused on the three most important facts we wanted them to know about us:

  1. “That’s a great question. What we've found is that people want what we've built, because we’ve been growing 20% week over week since we launched.”
  2. “The other interesting thing that we've found is that people give on average $20 per month in roundups, which means that we can create real change for charities, give them sustainable subscription revenue, which could change the way they have impact on the world.”
  3. “And the third really interesting fact is that non-profits are starving for this kind of thing, and they jumped on the opportunity to drive their memberbase to our landing pages. We've partnered with five non-profits that have sent us tens of thousands of visitors, and gotten an average signup rate of 20%.”

See how the original question isn’t really about this originally, yet we managed to transition to these three facts by packaging them within the answer?

Example 2: The total left-field question

What if the interviewer would have asked us something that’s totally unrelated to our idea or charities?

What if they would have, for example, objected to us as a founder team and said: “Well, you as a team don’t really have a history together, this is the first thing you’ve worked on together, and you don’t seem to be a great team. We don’t find your track record that impressive, so why should we invest in you?”

How to answer a question like that? That’s just a direct attack on us. How to tie in our three facts into that?

Here’s how:

  1. “Well, it’s interesting that you’re asking that question about us being a team and how we can work together. Since we’ve launched, we’ve been growing 20% week over week."
  2. “We found out together that people create about $20 a month in roundups on their credit card charges, so we can generate one dollar in revenue every single month per user, and give $19 to charities around the world.”
  3. “And we as a team have already convinced five charities to partner with us and drive tens of thousands of visitors to our site, converting 20% on average. So I think that we’ve proven that we as a team can build things, ship things and grow things. I think that’s what you’re really looking for in a team.”

Rather than directly telling them, “No, you’re wrong, we’re a great team! We work so well together!” And getting in a discussion where they try to prove that we’re not a great team and we try to convince them of the opposite, we used the three most important ideas we want them to remember about us as a proxy to demonstrate why we’re a great team.

Example 3: Like a politician

Let’s say it’s a question where you really, absolutely, in no possible way, can package your facts in an answer to a question, just do what politicians do with these kinds of questions.

“You know what, that’s a great question. Before I answer it, I want to make sure that you guys know 1, 2, 3.”

Works even better if you deliver it with the nonchalant composure of a true statesman.

Clarity = power

No matter what kind of questions an interviewer throws at you. If you yourself have clarity about the three things you want to share about yourself, you can use pretty much every question to focus the conversation on that.

Action steps

Think about the next time you’re going to be in a situation where other people can challenge you (be it an interview, a presentation, a sales call, a meeting, virtual or in real life), and ask yourself, “What are the key three things I want people to remember?”