Tips For Conducting a Better Interview

Cy Tidd
6 min readMay 8, 2022
Photo by Christina @ wocintechchat.com on Unsplash

For the past several years, I’ve performed behavioral interviews as my company’s version of Amazon’s Bar Raiser. I’ve interviewed over 250 people and learned a great deal. More than can fit into this article, but here are some highlights to help make your interviews better. It comes down to listening skills … and the questions.

Most interview questions are garbage

My job as an interviewer is to get enough data points from a candidate to make an informed hiring decision. It’s hard to do that if the candidate has to lie to me. Trouble is, most questions make candidates lie. Some examples:

Garbage Question #24: “Why do you want to work here?”

Answers to this question aren’t compelling. You’ll get some ego-stroking answer, “I’ve always wanted to work at your company.” Or the equally unhelpful, “I’m looking for new challenges.”

The real answer is usually “I’m going to make more money if I work for you, but it’s not socially acceptable to say that.” Or, “My current manager is terrible and I’m not allowed to say that, either.” Often it’s both. Do yourself a favor and don’t ask this question. You won’t get the real answer.

Instead, ask: “If hired, what do you want to accomplish in the first 90 days?”

This is going to tell you how much research they’ve done about your team/company and the problem space. The best answers are things like, “You’ve got X problem/challenge, and here’s what I’d do to test my assumptions / make the product better.”

Garbage Question #87: “Where do you see yourself in five years?”

I hate this question. Not because it’s goal-oriented (I hate goals). Not because a candidate has to invent a reasonable-sounding goal in the first place.

Humans rarely think five years into the future. The goals will be too small.

The things a motivated person can achieve in five years are truly astounding.

Asking this question is like telling someone to sell themselves short. Lame.

Garbage Question #99–263: “How would you-”

Every hypothetical question is junk. Don’t ask hypotheticals. As an interviewer, you are an obstacle to the candidate’s objective (a job offer). If you ask a hypothetical, they are going to tell you whatever they think you want to hear. The answer will paint themselves in the best possible light.

Instead, ask a situational: “Tell me about a time you did X”.

I don’t know the science, but I’d wager the questions access different parts of the brain. Situational questions seem to access memory, and hypotheticals appear to access storytelling.

Many times when I ask people a situational question, they’ve said, “I can’t think of an example.”

100% of the time when I asked them a similar hypothetical later in the conversation, they came up with a story. We’re wired to answer hypotheticals. We can’t help it.

I once asked the same person the same question a minute apart, about dealing with a difficult colleague. I phrased it as a hypothetical first, and the situational second. I got two different answers. They weren’t trying to BS me, and they didn’t even notice they’d supplied two completely different answers. The situational got the better response.

Garbage Question #301: “Tell me about your greatest failure.”

Remember, don’t make a candidate lie to you. Nobody is going to talk about their greatest failure in an interview. If it happens at all, they’ll do it anonymously on Reddit.

Ask about a person’s greatest failure and at best, you’ll get a watered-down hypothetical answer to what they think you want to hear. For any question that might paint a candidate in a negative light, you have to come at it sideways. For examples, see below.

Questions I Ask

Over time, my interviews have become rambling conversations. The discussion wanders wherever it wants. It’s more interesting for me, less predictable for the candidate, and generally a better experience.

The point is to get the candidate to relax. A relaxed candidate is going to tell me things they’d never say in a standard “tell me what you know” interview. I’m not doing this for sneaky reasons; I want to get a better sense of the person I’m talking to. Who are they, really?

I have five questions I tend to ask everybody:

What’s the hardest thing you’ve ever done?

This is my version of the “five year goal” and the “best professional achievement” questions. I try to get down to “brass tacks” at least once. If they’ve done it, they’ll know the gritty details.

I ask a lot of follow-ups, ranging from:

  • interpersonal relationships (the hardest problems often involve other people)
  • technical challenges (what do they know about hard stuff)
  • organizational quirks (how well does the candidate navigate cultural politics).

I get to the bottom of a candidate’s knowledge and force them to either say, “I don’t know” (this is good) — or start spouting obvious hand-wavy BS (this is bad).

If I asked your best friend or significant other to describe you with 10 adjectives, what would they tell me?

Self-aware candidates will have no trouble riffing off 10 adjectives. When they’re done, I ask them to pick “the one”, and tell me why.

What’s a decision you’ve made that went sideways?

This is a variation of the “greatest failure” question.

First, it usually avoids the guilt issue. “Failure” = “failure of character” for many people and nobody’s talking about that in an interview.

Second, they can tell me about A: how they make decisions, B: how they evaluate decision quality, and C: how they deal with uncertainty.

Third, I can ask what went wrong and see how they explain poor outcomes. Do they blame people or things?

Lots of follow-on questions in this space. Do they wait for someone to tell them what to do, or do they improvise? How do they tell if they’ve run out of room and need advice? Are they a “go from the gut” operator or do they need reams of data before making a decision? Both are valuable depending on the role, but it helps to figure that out in advance.

Who’s the most interesting person you know and why?

I ask this question to find out what a candidate truly values. It’s an indirect way to come at that information. People usually pick someone who personifies a value they hold dear.

There aren’t any wrong answers — I’ve gotten fictional characters — but the best answers are people the candidate knows personally. A family member, a co-worker, someone who has made an indelible impression on them. There’s always a story about them, and it’s fun to watch the candidate’s face light up when they explain why a person is so important to them.

What worries you the most about working here?

I love where I work but no company is kittens and glitter.

There are things wrong everywhere. I want to know what preconceptions the candidate has about our organization. What are their concerns? How can I help ease them?

This is another “tell me about your values” question.

Extra: Interviewing Managers

I tend to interview individual contributors more than managers, but the best managers:

  • won’t shut up about their current team(s) — I’m interviewing them, not their team, but it’s a good sign if they chalk up their successful deliverables to their team
  • have plenty of examples where they’ve served as a political meatshield to protect their people
  • can explain how they handle high performers and low performers
  • show how they drive outcomes instead of methods
  • can articulate how they’ve organized their team to shore up their own personal blind spots

Am I worried that a candidate might come across this article? This is a cheat sheet!

Not really.

On the rare chance that a candidate looks me up and goes further than my LinkedIn page, they might find this article.

They’ll also find my books and let’s be honest: if someone asks me about something they’ve read in one of my novels, I automatically like them.

Either way, we’ll have a good conversation.

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Cy Tidd

I write books and software. Opinions held loosely.