It’s nearing the end of the interview and you’re asked “do you have any questions for me?”. Now is your chance to take the reins of the interview, and this part deserves some preparation too!

At Nested I interviewed over 100 candidates and saw a large variation in the quality of questions asked. People who asked me the best questions got me really excited and definitely left me feeling more confident about the candidate’s potential impact.

Before jumping into great questions, I want to share a few pieces of advice on how to avoid bad questions:

  1. Skip any questions where you could find the answers yourself. You won’t come across as very prepared if you ask questions that are easy to answer. Have a look on the company website, read a few relevant news articles, then turn to Google. If you can’t find a solid answer then it should be a valuable question to ask in the interview.
  2. Be careful if you’re turning the tables. I’ve sometimes had candidates ask a “typical” interview question of me, e.g. “What are your strengths?”. If not done well, it can be quite off-putting. If you have a clear reason for asking the question (e.g. you’re being interviewed by your potential manager, and you want to understand their approach) then I’d recommend stating your intentions clearly. “I’d love to understand how you operate as a manager. What do you think your strengths are in managing the team?”

There is no quick recipe for success with asking great questions. I’ve put the soft skills to one side (e.g. tone, body language, etc) and written some tips that should help you prepare. It’s worth noting that your questions don’t have to tick all these boxes (e.g. you may want to ask about the person’s experiences, which means you’re not displaying understanding about the company).

  • Display your understanding about the company. I’ve written an article about 6 areas to research before interviewing at a startup. This preparation should give you plenty of ideas for questions around the company: the market, competitors, customers, business model, etc.
  • Use open-ended questions. When you start questions with “How..? Why..? What if..? What do you think about..?” you’re allowing a conversation to open up. This then gives you the opportunity to shine and show your insight. I also think open-ended questions require fewer assumptions, so they’re less risky. I’ve had candidates launch into closed questions before and they were completely wrong. e.g. “Do you find it hard to value houses if you don’t visit them in person?” (My answer was a quick “We do visit them in person, so we get lots of data points there. Is there anything else about valuations that I can tell you?”)
  • Be ambitious. “Nothing is off limits” is a bit too extreme as a piece of advice, but I’d encourage you to find the level of boldness you’re comfortable with. An example of a bold question would be “JP Morgan are spending $3 billion on developing products that are meant to beat challenger banks. Why is Revolut going to survive?”.
  • Make them relevant for the interviewer. Have a think about the areas the interviewer will feel confident answering, as this will lead to a better conversation. This doesn’t mean you have to ask the CEO deeply strategic questions, but she is in a unique position to answer where the company is headed in the next 2 years.
  • Have follow up questions/thoughts. The best questions open up discussion, and I always appreciate when candidates know the area well enough to follow up with more questions or thoughts. I’ve seen the opposite where candidates ask good questions, which make them sound informed, and then they are uninterested in my answer. This is very easy to spot! Most companies want employees who are curious and inquisitive, so don’t risk your question falling flat by not being able to enter the discussion.
  • Find the right level of specificity. I would recommend avoiding bland questions. An example I always use to explain this is “What is the culture like?”. I find that question really tricky to answer as it’s not specific enough: it doesn’t tell me much about what’s important to you. A more specific question would be “Do you share notes from important company meetings, such as the board meeting? I’m interested to see how companies are run”. This one allows me to tailor my answer and gives us more of an opportunity to have a discussion.
  • Ask something personal that makes the interviewer reflect. There’s a powerful moment in an interview when you think “oh that’s a good question”. Personal questions like “What are the people like here?” are okay, but a question such as “What keeps you at [company]?” gets the interviewer really thinking. Most people like telling their stories and speaking about themselves, so you’re leaning on a bit of positive psychology here.

Here are some generic questions that I’ve enjoyed being asked as an interviewer, and left me thinking positively about the candidate.

About my experiences

  • What opportunities for growth have you had since joining?
  • What does [company] do better than other companies you’ve worked at? What does it do worse?
  • What’s the most interesting part of your role?

About the company (generic)

  • What’s the biggest challenge the company is facing right now?
  • What company poses the biggest threat to [company]’s success?
  • What does success look like for 2019?

Here are some specific questions that have worked well when I’ve been an interviewer.

About the company (specific to Otta)

  • How are you thinking about partnerships? For example, with university careers services.
  • Why did you start Otta when alternatives like AngelList exist?
  • What is your approach for expanding into new segments of jobs? E.g. More senior roles

About the company (specific to Nested)

  • What will your approach be if Brexit causes the property market to crash?
  • Please would you help me understand how you finance the cash advance?
  • How will you expand outside of London where it’s harder to value properties, for example my grandparents’ cottage in the countryside?

This is a brief tour of how to ask great questions in an interview. It’s definitely a skill in itself to ask great questions. If you need more help with interviewing, please email me at