Getting hired at a startup series: Ask the right questions in the interview, close the deal, and get an offer (4 of 5)

Tip #4a: Ask the right final questions

There’s nothing worse than being an interviewer, opening up the interview to questions, and getting…. nothing….

“Nope, I think you answered everything I was going to ask you.” is the kiss of death for me for an interview. You could have ACED the rest of the interview… but if you aren’t curious enough to dive in deeper and peel back another layer, you’ve demonstrated you do not value one of my core values which is being curious… a student of the game.

I've always lived on a two-way street. Give and take. And in an interview, remember that the two-way street principle applies. You're going to be asked a lot of questions by the interviewer. But you should also ask questions in return to help you see if it's a good role for you. If you're great at what you do, then people should be DYING to hire you. Literally DYING. Like sticking knives into their heads. Or shooting themselves in the kneecaps. Or... well, you get the idea.

You can review a list of questions I already typed up that are good end-of-interview questions to ask. And here are a few below as well:

  1. Vision: What is your vision for the business? Where do you see it in three years? 

  2. Growth: Can you tell me about the growth of the business, and what are your goals for your org? Are you hitting them? Where are you not succeeding? And how do you see me being able to help influence those goals?

  3. Culture: What are the qualities you look for in a new hire on your team? (If you’re in Product Management and you’re being interviewed by someone from engineering, this is a particularly good question to ask since you’ll be working alongside engineers 24/7.)

  4. Org: Can you give me a quick flavor for the org structure here? How many teams, approximate size, etc? I’d like to understand how the company is resourced from a personnel standpoint?

  5. Leadership: Where do you see the organization needing to strengthen from an executive leadership perspective in the future? And does the company put emphasis on developing leaders internally? How?


Make sure that the job is a great fit for you. Ask questions. If the answers you get back from everyone really suck, or if you are not believing the people there, or if there are contradictions, or if you're getting weird vibes... Prod more. It's far better to walk away than accept a job that you have a really shitty feeling about before you get the job, only then to realize that it's not a fit for you down the road. Don't settle on something you don't believe in. Ask questions so that you know what you're walking into.

Tip #4b: Ask for the job

And finally. Close the deal. After your questions, always end with some variation of the following: “I’m really excited about this opportunity. It would be great to work alongside you.” When I interviewed at Wayfair, I was even more direct. At the end of the interview, I said: “I want this job. Will you hire me?” How’s that for direct?

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Getting hired at a startup series: Do what others are not willing to do to get the job (5 of 5)

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Getting hired at a startup series: Get the 411 up front… Ask who you’re interviewing - know their motivations and skillsets (3 of 5)