How to avoid losing a hiring manager interview

Kevin Landucci
Pass Interviews
min read

The four questions

In his book Acing the Interview, Tony Beshara theorizes that every interview contains 4 inherent questions. They aren’t spoken aloud, they’re asked and answered by the hiring manager. Since the hiring manager is almost always the most important vote of all interviewers, if Beshara’s theory is correct then the four answers determine much of whether or not you’re rejected.

The four questions

  1. Can you do the job?
  2. Do I like you?
  3. Are you a risk?
  4. Can we work out the money?

It’s a provocative and useful theory, even so, there’s an important point missing: one question is significantly more important than the rest. Candidates that focus on the key question can come out ahead.

The team

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“Can you do the job?”

It’s the job of a peer, more so than a hiring manager, to answer this question. Hiring managers are more removed from the day-to-day work of the boots on the ground, whereas peers have a better eye for a potential hire’s skills since they are in the thick of the job daily. It’s common for a hiring manager to delegate the decision of a candidate’s ability to do the job, totally or in part, to a “right-hand technical person.” While it matters if you can do the job, it’s better assessed by other interviewers, leaving the hiring manager to mainly focus elsewhere.

“Do I like you?”

This question might ruffle feathers as it’s subjective and likely biased. Nevertheless, some companies determine culture fit by asking “Is this person someone I could be friends with?” And there is research, referenced by the Wall Street Journal, that when managers encounter well-organized arguments combined with likeability, they tend to comply, even if they disagree and there’s a lack of supporting evidence. I can’t think of a better parallel than to a hiring manager interview where the candidate doesn’t check all the boxes but still passes the round.

However, likeability is not the cake (not even close), it’s the cherry on top. It may help get you over the line, but it’s not the top-of-mind factor for a hiring manager.

“Can we work out the money?”

There are only 3 moments when this question comes up: when you’re asked about compensation expectations, when an offer is made, and when you negotiate. These moments are short-lived lasting less than a few minutes, and it’s rarely the hiring manager’s job to handle these conversations. Also, the answer is usually “yes” on both sides, competitive companies can pay the right engineer whatever they want and, unfortunately, many candidates default to “yes” (regardless of the offer details) because they don’t know their worth.

Though it may be all about the Benjamins for some of us, this question is not a hiring manager’s top priority.

“Are you a risk?”

This is far and away the most important question to a hiring manager. The litmus test to sniff out would-be bad hires in interviews is to determine if they are a risk.  A bad hire is a worst-case scenario for a company; a conservative estimate for the cost of a bad hire is 1.5 – 2X their salary (source). Reference checks, background checks, and unregretted attrition exist solely to avoid false positives; an oversimplified argument is that interviewing is simply another means towards the same end.

This is backed up by behavioral science, too, a potential loss influences human decision-making 2X – 9X more than a potential gain. Since the hiring manager has so much to lose (duplicate work, avoided work, delays, morale issues, dissatisfied team members, shoddy performance reviews, PIPs, and firing), it makes sense they’d concentrate more on identifying red flags than green flags. To put it simply, they are looking for what’s wrong more than what’s right.

Common red flags (and opposing green flags)

Demonstrating that you’re capable, likable, or affordable is important, but less so than demonstrating that you’re a safe bet. Avoid red flags and signal green flags to show you’re a safe bet. There are a lot of red flag behaviors, but here are some of the most common. Every single one of these red flags comes from a quote a candidate said in a real interview.

“Do you use our product?”

Purpose of the question: Identify non-users (especially at product companies).

🚩 “I used to use an Alexa, but then I sold it when I moved to Portland.”

🏳️ 🟢 “I like Alexa lot, especially for recipes.

Tip: If you’ve never used their product, use it (even if very briefly, through a friend or even indirectly by watching others use it online) so when a company asks you about their product, you can be brief and answer in the affirmative.

Thanks to The Scribe for the photo.

“What are you looking for?”

Purpose of the question: Spot mismatches.

🚩 Tell a startup you want “mentorship”

🚩 Mention “an interest in AI” to a company that’s not an AI company

🏳️ 🟢 Tell startups: “A place to move quickly, make an impact, and work on a lot of cool stuff.”

🏳️ 🟢 Tell established companies: “Established engineering processes and best practices, and large scale problems to work on.”

Courtesy for the picture.

“Why are you looking to leave your current role?”

Purpose: Assess your level of motivation and accountability.

🚩 “I’ve been here for a while and now I feel a bit stagnant. So I’m looking for a product that makes me excited to go to work in the morning.”

🏳️ 🟢 “I’ve learned a lot here, and glad I got that opportunity. Now I’m ready for my next adventure.”

Tip: You want to avoid negativity, however minor, at all costs. The red flag answer implies that it’s the company’s (and not their own) responsibility to motivate them. And “stagnation” can be interpreted negatively implying a complaint of a general malaise.

“Why are you interested in our company?”

Purpose: For the company to find out how you can help them.

🚩 “Apple is my dream company. This opportunity would be good for me as the stocks are doing quite well and the office is next to my house. My friend works here and I’ve heard really good things. Oh, and the reviews online are strong as well.”

🏳️ 🟢 “My wife and I were university students, she was in France and I was in the States. FaceTime released this new feature called SharePlay which allowed us to watch movies together. Our relationship relied on that feature; it made us feel like a regular couple on a date night. I build great products that can have a deep impact on people’s lives as well. I was the founding engineer for a mental health app and a systems engineer on a service that shipped medicines to customers. Apple wants engineers who build great products customers love, and my expertise is building product features with real-world significance.”

“Can you tell me about this gap in your work history?”

🚩 “I took some time off for a passion project. I don’t know if you looked at my website or not, but I’ll read you the web address. I’ve also done painting, I had a big project for a church that I did and then the contract I had with The Mars Volta ended at the perfect time so I took the time to do the painting project and now we’re getting back into what I know how to do best.”

🏳️ 🟢 “Yup, I turned a two week contract into a 5 year gig working on production enterprise scale systems. Then I ran my own business successfully for 5 years. Then I had a few software projects I tried to get funding for, I didn’t but I learned a lot.”

Tip: If this is something you’re worried about getting asked, it’s better to address this before they ask. I call that “getting the elephant out of the room” and it’s covered in the next section. In the meantime: less is more. The good answers don’t meander, they spotlight your productivity.

The big takeaway: If it doesn’t help, then don’t share it. The only thing that helps you is relentless positivity (about past/current/future companies and colleagues, and yourself.) Negativity is usually found when the speaker is unaware. The best strategy is to aim for positivity especially if you genuinely don’t feel positively; when talking about a toxic workplace or person, act the opposite of what you believe. That’s not dishonest, it’s simply more loyal to your future than your past, and more intelligent.

The assumption is however you talk of your current gig is how you’ll talk about your next gig. Choose your words carefully.

Two other ways to go on the offensive

Excusing the fact that it’s about warfare, the game Battleship is quite like interviewing with a hiring manager because the ideal strategy is to both avoid destruction (red flags) and go on the offensive to win (green flags). Broadcasting green flags to common questions isn’t the only way to demonstrate that you’re a safe bet. For want of arming you with tricks for hiring manager rounds, here are a few more.

#1: Get the elephant out of the room

No candidate is perfect. All ye who enter here have at least one mark against them. Maybe they have less than 10 years’ experience with Java, never worked in banking, or have no experience with the exact database the company uses. Or maybe they’ve got a bunch of short stints on their resume.

A mediocre candidate knows they’re not perfect but is too shy to bring up the knocks against them; they simply hope for the best. That is a gamble. Concerns don’t go away when they’re ignored, they grow. Do you ever get rejected for a reason they knew before the interview started? Not enough experience in Java, not senior enough, etc. Those were marks against you when the interview started that went unaddressed and grew into  a problem. But they didn’t have to!

The elephant only goes away when you calmly point out what is on everyone’s mind.

A smart candidate knows that the hiring manager knows of their shortcomings, and can directly address them early so the concern shrinks or vanishes and the interview can focus on the candidate’s strengths. Since many interviewers mainly focus on looking for red flags,  a candidate who is upfront about their weaknesses saves time and seems refreshingly trustworthy.

This technique doesn’t have to be fancy. It can be knocked out in the first few minutes of the interview, right after the small talk:

🏳️ 🟢 “Hey before we get started, I don’t have 10+ years of experience with Java. However, Java has been my main programming language for the last 7 years. And, I do have more than 10 years with object-oriented languages.”

🏳️ 🟢 “To save you some time, I know I have a few short stints on my resume. The most recent one was because of a non-performance related layoff. And the one a few jobs back was frankly, not the right fit. I’d be happy to answer questions you have about either, because this company, and the focus on database stuff, seems like a match for my skills.”

#2: Apply a lesson from Harvard

Harvard’s Program on Negotiation says: negotiations are often decided in the first and last 3 minutes. What if the same was true for interviews?

Most engineers don’t need to do this. Still, there are situations where candidates will sacrifice a little bargaining power to get a deal done quickly. Maybe you’re on F1-OPT, you’ve been out of work for too long, or you just really like a company. If you want to push yourself over the line, and optimize for getting a deal done, reserve some time at the end of the interview for some well-orchestrated offense.

These moves are likely to feel clunky and unnatural, especially if you’re unpracticed with calculated social risks. No matter what, speak from the heart (yes, seriously), and practice before the real thing.

The first move is to ask inquisitively: “Is there anywhere in my experience or from this interview that concerns you about my ability to do this job?” Don’t ask in a dry tone, you want to sound curious. If they say “none”, that works. And if they say “Well, now that you mention it…” that works too because you get to address the point they bring up. Had you not asked, you never would have known! If this question is too scary or intimidating to ask, either soften the language or lean into practice (the best practice can be with companies you aren’t so keen on.)

This might sound ridiculous, or salesy, but the final move is to ask for the job; this video walks through how. Anecdotally, this works. I have had less than 10 clients try this, however, all of them got the job. I don’t have enough data to prove it, but I believe that because of the common problems in software engineering hiring from the perspective of companies (especially indifferent candidates who don’t do their homework or care), asking for the job is a cheat code.


Now you know not only how to avoid losing but also how to score points to win in a hiring manager interview! Avoid red flags to show them you’re not a risk. Go on the offensive by signaling green flags, proactively addressing concerns, and when the situation calls for it, asking for the job.

For candidates looking to thrive in this broken hiring system, fill out one form on ApplyPass, a human-monitored AI, and watch the interviews roll in.

Dan Klos
Co-Founder & CEO @applypass
Dan has spent the last 8 years helping software engineers level up their career. He created Outco to help over 2,000+ engineers secure top-paying job offers. Currently, his entire focus is on building ApplyPass to aid engineers in getting 40% more interviews and saving more than 5 hours per week on job applications. When he's not at work, he's deeply involved in activism, challenging hikes, and canoeing.
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