REVIEW: Startups Live ICYMI | The Art of Interviewing
What should you look for in a job candidate? What questions should you ask? Founders share their interviewing expertise, successes and awful outcomes.
Written by Keith Liles // Also shared on Startups.co.

“If you join the company you are interviewing with, you will be investing a large percentage of your waking hours, act as an investor — because you are one.”
–George Kassabgi, Level Up Your Interviewing Skills
Get out of your chair and show interest, do your homework, take pride in what you’ve done, brand yourself George Kassabgi advises interviewees who want to wow their potential employers. He goes on to suggest seeking mentors.
And what about the role on other side of the table? What are some of the best questions to ask? What are the truest objectives of he interviewer? What works? What doesn’t?
A startup is a different animal than an a long established company. How does this change the the interviewing process? What stays the same?
In the spirit of startup adaptability and responding to your audience, the topic of conversation was changed at the last minute today to focus on interviewing — “such a critical element of starting up” as Ryan Rutan called it. Join us as the Startups Live community turns over their interview experiences.
“Have any amazing anecdotes around a recent hiring cycle to kick us off?” Ryan asked of Michael Kassing.
“So I am on the flip side of being a difficult interviewer to interview with.”
“Haha, How so?” asked Steph Newton.
“Aren’t we all?” Ryan mused.
“So here is what I do, because I do not like the in the box thinking about looking at people. I am usually taking for granted that you know how to code or do the job you want. What I try and do is figure out if you are a good fit for a fast moving dynamic startup and if you can adult really well.”
Michael explained ‘adulting’ really well as being able to take direction and run with it. Doing your job and asking questions when you get stuck. The opposite of micro-managing. Working toward the goals of the company.
“We don’t even set a max vacation policy at the company. You are a friggen adult. If you work 10 hours a day and want to take a week off and you setup your project to be able to handle this, go forward and do it. Think and be good. Many can’t adult well.”
“Once we get past the background items we usually give a hypothetical that tests how they think. ‘We have a client that wants to display zoo information about all of the zoos in California and the animal name and types…’ They have to walk through the approach blind. We put in twists and turns to see how well they deal with issues and how they think past roadblocks.”
“The BEST and final question I usually have is: ‘Tell me a joke.’”
“Why? Just a jerk? Not at all, this tell me a joke thing comes out of nowhere in a situation that it is totally inappropriate while dealing with a high pressure situation.”
“It places so much more pressure for a quick answer and dead silence. I don’t care about the joke, I care about their reaction. How do they think, what are they searching, how do they respond with ‘I don’t know one.’ Do they fold?”
“The problem that I have with any techniques in an interview setting,” said Ryan, “is that the context is still that of an interview. I want something that breaks that environment — and gives me a chance to see them in a more natural state.”
(Note to future applicants at Startups.co — interviews may include an escape room after Ryan’s recent exposure to one.)
“Totally agree,” offered Michael. “…the goal is only to find out how their brain works and how it moves. We started to move to these other ways of interviewing after we hired someone who looked GREAT and sounded better, but once he was here, he contracted to someone in India to do his job for him at about $12 an hour.”
“Whaaaaat?”
“Yeah, it happened.”
“Amazing.”
“If he had contracted with someone who was good, we would have never known!”
“Do you think there was anything you could have done at the interview stage to uncover that?” Ryan asked. “That feels like something you can’t really plan for / process your way around.”
“And for our final question,” Steph proposed, “… any plans to outsource your job?”
“No, I don’t think we could have, he was really good at talking the code.”
Of course, everyone wanted to know how the guy was caught…
“Code review, and he could not even answer simple questions. We started digging and found that he not only used his company email to setup the contract but also his company computer.”
“We ended up making a take home exam with very limited time points to try and kill this type of person out. Totally not saying we did a proper interview on the guy. Just a stupid lesson we learned on the path. We will learn more, it’s part of the process.”
“One of those random collisions with a bad actor you chalk up to being a cost of doing startups,” said Ryan. “Luckily, in my own experience — these are rare exceptions.”
“I’ve been a programmer for over 37 years,” Mike Yearwood dove in. “I show prospective programmers 3 lines of code. If they can’t debug it, they’re out. If they think it through and solve the problem, they’re shortlisted.”
“Having an ability to objectively test is great,” Ryan responded. “This breaks down a bit outside engineering in my experience.”
“I’m not entirely sure there’s a 100% fix for bad interviews,” said Wil Schroter, “but I will say that limiting the interview time to 15 minutes (as a default) has never failed me.”
“I can’t think of many times where I didn’t know within 15 minutes (usually a lot less) whether I wanted to spend another 15 minutes.”
“The way I see it, a hard ‘no’ tends to be obvious in a short period of time — so it’s great to get those meetings done quickly. And if you really like someone, no one will complain if you go over in time. I see investors do this all the time, and it’s smart.”
Imran Siddiq went further, “Actually 10 min is enough.”
David Krock spoke up for another camp of thought. “I’m on the opposite side of this. I will interview for hours, depending on the role. I do think a quick hook if feeling a ‘no’ is usually correct, and will do the same. But fishing out an A-Player rockstar from the huge swath of average players takes time.”
“Are you saying it’s hard to separate the rock stars from the average players in a short period of time?” Wil pressed.
“I think as a rule, yes, but there are always exceptions. Usually true rockstars wow from the start, but so do a lot of average players. Some of my most productive hires have come from spending more time than less. And I’ve saved myself a few bad hires by doing the same.”
Wil looked to clarify his own position, “I’m not saying I make go-forward decisions in sub-15 minutes. I’m saying the sub-15 is how I get through obvious bad fits. I could definitely see why you would want to spend hours on your most qualified potential candidates.”
“At a previous startup,” said Steph, “I liked that the final interview was with the entire team. Granted, our team was 3 people. But I liked how everyone had some input.”
“I tend to find myself asking questions about how a person knew to do something really well in the organization,” said Wil. “In other words ‘Were you told to do that or did you determine it needed to be done on your own?’”
“If someone is told to do something, and they did it, that’s awesome. But the person I’m looking for did something no one thought to ask.”
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