How to Interview and Not Screw It Up

Interviews are tough. You might hire someone who is terrible and have to deal with that, or if you’re the candidate you put in all of this time to maybe not get the job. I was talking to a friend yesterday who owns a small business and is walking through a painful departure of an employee who was a bad fit. We got to talking about interviewing, and I think there is some low lying fruit for all of us to consider whether we are hiring or being hired.

Let’s boil it down to the absolute basics. An interview is a quick date to determine if you should say yes to a long term relationship. That’s insane. No one does that. For many of us, we will spend far more time working with our team than even talking to our significant others, making it even MORE critical we get this right. And yet, how many of us have spent time working on our interview strategy?

Here is a simple strategy for both Interviewers and Candidates. Interviewers: figure out what you need to know, then tailor your questions around that. Candidates: let yourself become a known entity, and prove you can add more value than you destroy.

For Interviewers —

I have made a lot of hiring mistakes, and they all started as interview mistakes.

You typically only get 60 minutes to determine if someone should join your company. How do you maximize every second of that meeting to make good decisions about the people you bring on? Hint: just shooting the breeze with someone is a terrible strategy, as is asking them to recite their pre-recorded list of “weaknesses”. You will not find out what you need to know.

We should back up and start with this: what DO you need to know? When I’m interviewing someone, I want to know the following:

Does this person have the ability to do this job?

1. Do they have the experience I need
2. Will they be able to handle the velocity of the role?
3. Are the able to endure the responsibility of the role?

Will this person gel with the team?

1. Will their skillsets compliment what we already have?
2. Do they raise the bar of talent?
3. Will they inspire others around them?
4. Will they fit culturally?
5. Will they support their teammates?
6. Are they going to try and make the team better?

Does this person work hard??

1. Will they need to constantly be pushed?
2. Will they be self motivated?
3. Will they demoralize teammates by not pulling their weight?

Will this person grow?

1. Do they have an ego?
2. Do they display humility?
3. Are they receptive to feedback?
4. Can they admit they were wrong?
5. Are they self-aware or will I have to spoon feed them all their feedback?

And that’s just the bare minimum of what I’d like answered before I offer someone a job. It’s a lot.

Of course, some of those are more important than others. But for people that have checked every one of those boxes, those have been exceptional employees that I would hire again. And that is the goal of what you want to be able to say: “I would hire this persona gain in a heartbeat.”

How do we get an honest assessment of all of these in just one conversation? It’s difficult, and I would always recommend having multiple people interview a person to assess for various aspects of the above. But most people, are overly gracious with how they rate someone’s interview. Some of the worst hires I have made were when I relied too much on someone else’s opinion of a candidate in their interview with them. You need to assess for yourself, and you need to be brutally honest. For most roles, you need to leave your empathy at the door.

Getting your interview/questions dialed in is incredibly important, and will make or break how well you understand the answers to the questions above. Build questions around what you need to know. Try them out on friends to see if they work. Refine them over and over until you are happy with the results. My questions have taken me years to develop. Steal them, make sure you know how to use them, and know WHY you are asking them.?

1. What is your superpower - gives you a first glimpse at how they perceive themselves and their level of self awareness. I typically ask this like “if you are standing in a room with 100 people, what are you going to be better at than anyone else naturally?” This type of unique question will force them to stop and think, and while the answer may not be very inspiring (and likely wrong) you won’t get a canned response, and will understand a bit more about who they are naturally.
2. What do you do in your free time - if someone is running a non-profit/business on the side while chasing 5 kids around vs. playing video games, you’ll get some idea of what is important to them. Understanding what people value will tell you a lot about how hard they will work.?
3. How conflict averse are you on a scale of 1-10 - all of these answers can be manufactured, but you might be surprised at how honest people are when they don’t know why you’re asking. Some people think it’s better to be higher on this scale, others think lower is best. Most people just don’t know, and will give you an honest answer. I personally like hiring people who are willing to have conflict. Bottling frustrations will lead to issues, not to mention it could hinder their growth as a worker or as a member of the team.
4. How much of a perfectionist are you on a scale of 1-10 - this is something I like to know that speaks to their work ethic. Anyone can slop together a 1 out of 10. And while people that are 10’s could have a hard time moving fast enough because they could be obsessive about details that don’t matter, I want people that produce quality, and that makes me look for people at the upper end of this spectrum.
5. What’s the hardest thing you’ve ever done - hard work produces calluses that enable future hard work.?
6. What is a weakness you have that you often forget about - I like asking this to look for self-awareness, but also where they struggle to change. It’s nice to understand baggage you’re inheriting with a new teammate, without having to learn about it the hard way.
7. Tell me about a time you were wrong - answers to this vary wildly, and I don’t have one particular one I need to hear. What I look for in these is what they did about it during and after. You can learn a lot about how someone works within a framework of a team, their humility, and if they learn/grow by just listening to these responses. If someone can’t come up with something, or blames everyone else that was involved, don’t hire them.
8. What overwhelms you - this is my nice way of asking someone when I should expect them to lose it while working for me. Understanding what makes your people tick (and break) is EXTREMELY important for good people leaders. Knowing these things as early as possible is critical to understanding if they can do the job as you need them to, and get along with the team.?
9. What is your default mode when you are stressed - everyone handles stress differently. Like question 8, it’s very helpful to know what to expect so you aren’t blind sided when things are going sideways. A good leader is going to anticipate what is around the next corner AND how their people are going to respond/react/freeze.
10. What demoralizes you, and how do you fight through it - most people don’t actively try to pull themselves together quickly. When there is a team relying on you, it’s great to know if someone has a framework in mind for how they remain focused and keep working hard, even when they don’t feel emotionally in it. Everyone gets demoralized at some point.
11. Are you ever intimidated to give your opinion - use this one carefully! This can often sound like a trick question to people who aren’t sure if they should question authority or not. I ask this to ensure that this person will not be afraid to share things that could help the team. Are we going in the wrong direction? I want to know. Are they going to try and make this team better by speaking up? People can be intimidated by their leaders to a degree that keeps them from speaking up, but WE as leaders can control that by working to make it clear we welcome feedback. So if the environment is friendly, will they still remain silent??
12. What are a few ideas you disagree with? Steel man one for me - this might be my favorite thing to ask. I typically frame it as “Give me three ideas you disagree with.” Then, I pick one of those ideas, and ask them to argue for the position they disagree with. If someone can’t get into an opposing parties shoes to understand why they think XYZ, then they won’t do it on my team. This speaks to their humility, and what they will be like as a teammate. I don’t want people that have blinders on all the time. I want people who know how to be empathetic. I’m not hiring them to teach them empathy.
13. How do you keep learning - I want my teams to be so good, that in a few years after I start building them, I wouldn’t be able to get a job on the team if I applied. The only way to do that is to keep up leveling the talent. People that have an insatiable desire to learn, and have habits formed around it, are going to grow, and they will keep raising the bar internally.?
14. What’s something you had to work on for a long time - work is tiring, and it’s easy to get disenchanted with projects that take months or years to complete. Depending on the role, you really need someone to have the grit to be able to handle that type of long term work. I love hearing about people’s stories of something that took a long time to achieve. The hardest workers will have a few of these stories. Pro tip: current/former elite athletes are absolute gold mines when it comes to people that know how to WORK and work hard.
15. How do you feel when your work is critiqued - this is a hard question to get an honest answer to, because everyone knows the right answer. I’ll still ask it sometimes though to try and keep uncovering how they’ll gel with their team, and how comfortable with humility they really are. The exact response here, and all of the non-verbals really matter.
16. How do you approach a problem you’ve never solved - if you’ve ever read about large tech company hiring practices, you’ve likely heard of some of these abstract questions they ask like “how many tennis balls can you fit in a limo.” I’d recommend making up your own version of this pertinent to your company. The goal here is to gauge how independent a person can be, how they approach abstract problems, and how they break down a challenge. You will also get a front row seat to how they handle pressure in real time.
17. Describe your ideal leader - people tend to answer this based out of their bad experiences. I like this to learn where people’s scar tissue might be. You can learn a lot about a persons growth potential and potential team dynamic based on what they hate.
18. Tell me about a time you had to build up a coworker - if they can’t think of one, massive red flag. You want people who add positively to the culture of your team. There is nothing worse than someone who doesn’t have the humility to elevate others good work. When I’ve hired people like that, they have never worked out long term. Ever.
19. Why do you want to work for us - answers to this can speak to their fit for the role and work ethic (to learn enough about the company pre-interview to have a thoughtful response). It’s very obvious when you are just a paycheck to them. I always prefer to hire people excited about contributing value to THIS thing. They’ll be more satisfied, and happier long term if they’re emotionally invested.
20. Why should we NOT hire you - I ask this at the end of every interview I do, regardless of the role. If someone cannot evaluate the role and themselves well enough to see where there could be some area that isn’t a perfect fit, I worry about their self awareness. This question also flusters nearly everyone, because they think you’re asking them to hurt their chances in the role. When in reality, you’re asking them to see if they are introspective and can follow directions, even when they don’t understand why they’re being asked something. It’s the final test.

These questions… are not normal. And most of them don’t have a right answer. The “answer” you are looking for is HOW they answer the question in many respects. This strategy requires incredibly careful active listening and engagement with the candidate. It’s not easy. But done well, you will make fewer hiring mistakes if you can learn the types of things these questions elicit.

Now, I don’t ask all of these questions in most interviews. Depending on the role, there might be a few others. But I do try to get through all of them in 45 to 60 minutes. Candidate response times will limit that, so I try to warn them that I have a lot of questions to get through. I am also a firm believer in getting their questions answered as well, but I typically start with those, as I am usually the last interviewer in the hiring process and they have questions by that point.

Remember, these questions are not prescriptions, but merely the ones I use to uncover what I want to know about everyone coming to work for us. I’d strongly suggest making your own list of things you want to know, then forming questions around those things. Remember. We’re talking first date, to long term relationship. Don’t sugar coat ANYTHING. If you don’t leave the interview dying to hire them, you should pass. Read that again, then STICK TO IT.

For Candidates —

Now, most of you reading this, are the Candidate! If you made it this far, you’re already demonstrating good work ethic! This is a great start. But why is your section so much shorter if there are way more of you?! Because once you understand what companies want, you simply need to show you can provide that. Your job then, is NOT to answer their questions. It is to prove you will add more value to their team than anyone else.

There are a million articles and YouTube videos about how to interview well. I won’t go into all of the things you should do to operate professionally. If you are still working on showing up on time, putting your best foot forward and being polite, I would focus there and ignore everything above. Those are table stakes. Nail those down.

For the rest of you, reverse engineer all the feedback above for Interviewers. At its core, it is a long process of getting to know someone, the value they will provide, and the possible value they will destroy. Your goal then, in every interview, is to prove that the value you will provide is exponentially higher than the value you will destroy.

What is value destruction??

• Are you difficult??
• Arrogant??
• Argumentative??
• Not easy to get along with??
• Will you require hand holding because you can’t operate autonomously or in a trustworthy fashion??
• Will you have to be reminded to do things multiple times??
• Is your new team going to hate working with you??
• Do you think you have no where you need to improve??
• Are you unreliable?
• Do you think everyone should adapt to you??
• Do you feel like you are entitled to a long list of things?

That’s value destruction. It sucks the life out of people and teams dealing with it, and asymmetrically counts against all of the positive things you bring. For what it’s worth, I would pick a C+ talent person who is humble and teachable, over an A+ talent who is a self-absorbed, jerk. That person is a net loss to the team, regardless of how brilliant they are.

Focus on describing how you will add value out of the gate. Reveal yourself and your character during your interview, so they feel like they know you, and you will leap ahead of 99% of other Candidates in their pipeline. Now do that better than the rest of the 1%, and you will get the job.

Poorly executed interviews are so easy to avoid. Be intentional with the questions you ask. Show the value you will bring an organization. That’s it. That’s how you hire well, and that's how you get hired.