Hiring questions you probably weren’t asking, but you should

At Bolt we’ve experimented with 1000s of interview questions. It’s been trial by fire, but the result is we’ve now hired 300+ amazing people. For 5+ years, I interviewed every single candidate. Here are my 15 highest impact questions to include in your hiring process 👇
Question 1: I’ve read your bio, but how about we start sharing each other’s stories? This sounds fluffy. It’s not. It’s crucial to learn who the candidate is. The best teams are a combination of skills + incentives + personalities. Most hiring stops at the skills part.
Question 2: Give me an example of adversity you’ve had to overcome and how you pushed through? This question shows you a lot about someone’s character. We face all sorts of adversity at startups (major and minor). It’s important to construct a team of creative problem solvers.
Question 3: What achievement are you most proud of? This allows you to peer into a lot of things, but namely: – What is their bar for achievement? Speaks to excellence. – What drives their pride? Speaks to motivation. – How do they think about tradeoffs? Speaks to judgement.
Pro tip: On Question 3 you can really dig in. What part of the project did they own exactly? What was the toughest tradeoff they had to make? What went wrong unexpectedly and how did they rebound? There’s a lot of meat on this bone.
Question 4: What motivates you? Double click on the “pride” point above. It’s important to understand why someone does what they do. If you feel like you’re getting a cookie cutter response – dig deeper. Understand what motivates them on the deepest level.
Question 5: Who was your best boss? And your worst boss? Dig in. What made them so great or so terrrible? This will give you a really strong sense of what they value in leadership. You’ll also get a sense of whether there’s a good fit with your style of leadership.
Question 6: What’s the biggest mistake you’ve made? Everyone makes mistakes. For self reflective and self aware candidates, this should be a lay-up. For others, it’s actually a tough question. This also lets you know if they are comfortable talking about failure.
Question 7: What’s one thing people commonly misunderstand about you? Everyone is misunderstood in some way. That’s what makes this question so powerful. I learn SO much here. Remember, you’re not just to evaluating but also preparing yourself for working with them!
Question 8: What’s your greatest strength at work? What’s your greatest area for improvement? I’m always amazed at how accurate people are assessing their own strengths and weaknesses. Instead of beating around the bush… Ask the question directly!
Question 9: Ask about a perceived weakness During the interview, you’re evaluating in real time the pros and cons of a candidate. Instead of keeping the cons in your head, give them a shot to turn you around. Make sure to ask questions that prove or disprove the concern.
Eg if I think they’re a great executor but I’m concerned that they don’t have original ideas… I’ll ask what was the most creative or non obvious project they undertook and how they came up with the idea.
Question 10: What’s an epic hiring close you made recently? No matter the role, in a startup, everyone is a recruiter. Don’t forget this important truth. This is one of my favorite questions to ask. Credit: Tido Carriero at Segment
Question 11: Will people follow you here? To double down on recruiting… The best people bring other amazing people when they join you. It’s hard to predict this in advance, but I like asking this question directly to see what they say.
Question 12: What do you do for fun? Ah… such an easy one to overlook! I love to get the full spectrum of someone’s personality. Work is hard. You gotta work with people who keep it fun along the way. Both selfishly and for your team.
Question 13: So… what do you like about [Bolt]? THE most important question! If they’re talking to you, they should have a pretty good answer to this question. “I got an email and decided to interview” – No way. You need missionaries who believe in what you’re doing.
Question 14: What questions do you have for me? I give them at least 10 minutes to ask me questions. Don’t forget that great candidates are also INTERVIEWING YOU. Interviews are ½ evaluating and ½ selling. Don’t forget the SELLING!
There we have it! I’ve experimented with 1000s of interview questions. These are the ones I fall back on most. They are tried and true. And don’t forget: show up present and engaged in interviews. It helps you evaluate better. It also helps you leave a great impression.
I think my account is… taking off. It’s an honor to share my learnings building multi billion dollar companies, as well as my dance nonprofit, with you all. Building is easier with good guidance. If this was helpful, follow me @ryantakesoff. Let’s take off together 🚀

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