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Interview Questions to Hire for Character

UnrealCreative

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As the old adage goes...

"You can Train for Skill, but you can't Train for Character."

Disclaimer: I've only hired 5-6 different freelancers over the past year.
However, the quality of the Freelancers dramatically improved after utilizing these interview questions.

In fact, every hire that came through this process ended up being the best people EVER to work with, and are all incredibly happy to work with me.

Before...
(One of my old hires. He was given 48 hours to complete project and did not advise me upfront of being sick. This project was due the next hour):

Screen Shot 2018-05-13 at 6.11.04 PM.png

After...
(New Hire Utilizing this List. Asked if there was anything I could improve on as a manager):


Screen Shot 2018-05-13 at 6.10.40 PM.png

If you're just starting off hiring and want amazing people to work with who will never stab you in the back...this will be a good filter. Feel free to take and re-use on your own whim.

Here are the questions pulled directly from one of my job posts,
plus the thought process described below:

-> Asking for Sample works they've done.

-> Basic questions related to the work

Shows their experience level and performance/efficiency in performing a task.
If they take an enormous amount of time to complete a project, they're either inefficient or inexperienced. Likely both.

-> What are you most excited about this position?

Shows their interest level and potential commitment to your project. "Just need a job" or "Need some cash" are red flags for me as they won't perform their best and are not loyal.

-> What concerns do you have about this position?

Helps me understand my own positioning and make the job offer more enticing based on their 'wants' from the last response.

-> Describe a Time when a project you've worked on before went badly.
What went wrong and how was it handled?


Tells me a LOT about their character. Do they take ownership or point blame?

-> Describe a Time when you did not perform to your abilities.
What was the situation, and how was it handled?


Similar to the previous question, but worded differently.
Another integrity test for lying. Nobody is a perfect employee.

-> Describe a Time when you went above and beyond for a client.
What did you do? How was it received by the client?


Now we're looking at the positive sides of their character.
The 'How was it received' part is big because the difference between SAYING you deliver value and ACTUALLY delivering value to a client is night and day.

-> What is the top lesson you have learned in life so far?

Another character question.
Really brings interesting info to the surface

-> What is the biggest misconception others have of you?

This helps me know how self-aware someone is, and how well they're able to gauge other's responses to their work habits and adjust accordingly.

-> What was the best boss you've ever had? Why?

I'm looking for "The one that pushed me and helped me learn a lot" sort of answers. For me, it gives me an idea of how prideful they are. Literally had an applicant badmouthing his previous boss. Something along the lines of "I never liked any of my bosses that's why I'm a freelancer" is a red flag for me. They could have been the most skilled applicant, but this type of person will stab you in the back later.

-> What type of people do you have difficulty getting along with?

If they respond along the lines of "lazy / irresponsible people", I'll know he's the exact opposite.

-> Type 'watermelon watermelon watermelon' in the header of your cover letter.

This shows me that an applicant read the entire ad all the way to the end. If they say they're 'detailed oriented' but fail to type this, I know they're lying...and their application gets trashed immediately :)

Also, be sure to check out @csalvato's thread below:
GOLD! - Building a team around you that will follow you to hell and back.

Chris' thread and slide deck is very good at outlining the hiring process as a whole.
Consider this supplemental material that goes into the mechanics of the interview, coming from someone who has implemented it with moderate success.

If you have any questions or something to add, feel free to reach out!

edit: Mods, can you fix for formatting? I'm getting big paragraph breaks (gaps) in this post and have zero idea why it's happening. @Andy Black
 

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OP
OP
UnrealCreative

UnrealCreative

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Awesome! So glad your hiring process has turned around!
Thanks Chris! The difference was night and day.

As a side note, I think the biggest lesson taken from this entire process is that It's always worth taking more time to process candidates. Candidates have to jump through a dozen hoops to get hired.

"Hire Slow, Fire Fast" -- Otherwise the bad apples will continue to be a headache.
 

AfterWind

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watermelon watermelon watermelon

I'm just kidding. Really helpful questions to ask. I feel much more confident now if I were to hire someone. Especially in the IT industry where, most employers, give you all sorts of useless tests about what you currently know and they focus mostly on that... They could learn A LOT from this.
 

csalvato

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watermelon watermelon watermelon

I'm just kidding. Really helpful questions to ask. I feel much more confident now if I were to hire someone. Especially in the IT industry where, most employers, give you all sorts of useless tests about what you currently know and they focus mostly on that... They could learn A LOT from this.
I'm actually against the random-hidden-word-in-the-job-description thing because it's kind of demeaning.

Instead I make it required to answer a meaningful question, instead. If they ignore the question, they're out.

For example, I say to answer this question when they send over their application: "What makes you excited to work at <company>?"
 
OP
OP
UnrealCreative

UnrealCreative

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I'm actually against the random-hidden-word-in-the-job-description thing because it's kind of demeaning.

Instead I make it required to answer a meaningful question, instead. If they ignore the question, they're out.

For example, I say to answer this question when they send over their application: "What makes you excited to work at <company>?"
Good points -- Definitely hear where you're coming from.
These questions are all geared to look for depth of character, and understanding applicant's "whys." Their responses will reflect that depth.

That being said, this was Upwork and people are notorious for copy + pasting the same proposal without considering what they're actually applying for. I don't have statistical evidence to back it up, but it seems like an effective method for screening out those who are not truly invested.
 

ApparentHorizon

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As the old adage goes...

"You can Train for Skill, but you can't Train for Character."

Disclaimer: I've only hired 5-6 different freelancers over the past year.
However, the quality of the Freelancers dramatically improved after utilizing these interview questions.

In fact, every hire that came through this process ended up being the best people EVER to work with, and are all incredibly happy to work with me.

Before...
(One of my old hires. He was given 48 hours to complete project and did not advise me upfront of being sick. This project was due the next hour):

View attachment 19451

After...
(New Hire Utilizing this List. Asked if there was anything I could improve on as a manager):


View attachment 19452

If you're just starting off hiring and want amazing people to work with who will never stab you in the back...this will be a good filter. Feel free to take and re-use on your own whim.

Here are the questions pulled directly from one of my job posts,
plus the thought process described below:

-> Asking for Sample works they've done.

-> Basic questions related to the work

Shows their experience level and performance/efficiency in performing a task.
If they take an enormous amount of time to complete a project, they're either inefficient or inexperienced. Likely both.

-> What are you most excited about this position?

Shows their interest level and potential commitment to your project. "Just need a job" or "Need some cash" are red flags for me as they won't perform their best and are not loyal.

-> What concerns do you have about this position?

Helps me understand my own positioning and make the job offer more enticing based on their 'wants' from the last response.

-> Describe a Time when a project you've worked on before went badly.
What went wrong and how was it handled?


Tells me a LOT about their character. Do they take ownership or point blame?

-> Describe a Time when you did not perform to your abilities.
What was the situation, and how was it handled?


Similar to the previous question, but worded differently.
Another integrity test for lying. Nobody is a perfect employee.

-> Describe a Time when you went above and beyond for a client.
What did you do? How was it received by the client?


Now we're looking at the positive sides of their character.
The 'How was it received' part is big because the difference between SAYING you deliver value and ACTUALLY delivering value to a client is night and day.

-> What is the top lesson you have learned in life so far?

Another character question.
Really brings interesting info to the surface

-> What is the biggest misconception others have of you?

This helps me know how self-aware someone is, and how well they're able to gauge other's responses to their work habits and adjust accordingly.

-> What was the best boss you've ever had? Why?

I'm looking for "The one that pushed me and helped me learn a lot" sort of answers. For me, it gives me an idea of how prideful they are. Literally had an applicant badmouthing his previous boss. Something along the lines of "I never liked any of my bosses that's why I'm a freelancer" is a red flag for me. They could have been the most skilled applicant, but this type of person will stab you in the back later.

-> What type of people do you have difficulty getting along with?

If they respond along the lines of "lazy / irresponsible people", I'll know he's the exact opposite.

-> Type 'watermelon watermelon watermelon' in the header of your cover letter.

This shows me that an applicant read the entire ad all the way to the end. If they say they're 'detailed oriented' but fail to type this, I know they're lying...and their application gets trashed immediately :)

Also, be sure to check out @csalvato's thread below:
GOLD! - Building a team around you that will follow you to hell and back.

Chris' thread and slide deck is very good at outlining the hiring process as a whole.
Consider this supplemental material that goes into the mechanics of the interview, coming from someone who has implemented it with moderate success.

If you have any questions or something to add, feel free to reach out!

edit: Mods, can you fix for formatting? I'm getting big paragraph breaks (gaps) in this post and have zero idea why it's happening. @Andy Black
That's a lot of questions for UpWork. I'd never apply to this tbh (coming from programming perspective)

I've only hired programmers, and they get 1 question: Write a program/script/function that does XYZ.

The way they answer determines if they're hired.

1. Most will say yes they can do this, with a copy pasted cover letter
2. A few more will actually write out the function
3. One or two will write it out, explain it, and give suggestions for other situational solutions

Number 3 always gets hired, and it hasn't failed me yet, for quality work and punctuality.
 

Real Deal Denver

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Number 3 always gets hired, and it hasn't failed me yet, for quality work and punctuality.
My bosses did me the greatest favor, although it wasted years of my life. They played cover their butt, and if anyone showed initiative or exceptional skill, they were "dealt with accordingly." The directive must be followed at all times, and the number one rule is to make your boss look good at all costs. That means that they get credit for my work. After the credit has been doled out, I am fortunate to be treated as a "favorite" for doing such a good job.

I have little to no respect for middle managers. I've encountered so many bad ones. I can absolutely assure you that the peter principle is very much alive and well.

So here I am. It was a hard road to get here, but I made it.

I thought about applying for positions for the fun of it. I would bring my own questionnaire to the interview. What? That would raise some eyebrows. Starting with - why do you think someone would want to work for your company, compared to your competition? How do you feel about whistle blowers that are looking out for the good of the company, even if it means ratting out a supervisor? Is it possible for an exceptional employee to "jump line" and be promoted over other employees that have more time in grade? Are you insulted that a lowly potential employee would dare to bring their own questionnaire for you to fill out?

I might do this. It could be a lot of fun. I assure you that no managers would be harmed in the process - I am strictly in it for the sport, so I practice catch and release.

If managers could have recognized talent along the way, I'd be a happy corporate employee today. Still in the matrix. Unknowing, and liking it that way. That's how it goes. Never quite according to plan, for some reason.

I'm not bitter. I'm in a much better place, by far. Just thought some here might like to hear that there is another side to the story. That seamy underbelly of business that lurks in the shadows... which we must never call by name.

And no, the movie rights are not for sale. Don't ask. Okay ask - I'm easy. LOL.
 

ApparentHorizon

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I thought about applying for positions for the fun of it. I would bring my own questionnaire to the interview. What? That would raise some eyebrows. Starting with - why do you think someone would want to work for your company, compared to your competition? How do you feel about whistle blowers that are looking out for the good of the company, even if it means ratting out a supervisor? Is it possible for an exceptional employee to "jump line" and be promoted over other employees that have more time in grade? Are you insulted that a lowly potential employee would dare to bring their own questionnaire for you to fill out?
Bringing the right questions to the interview is key. I'd think that asking about whistleblowers makes most HR depts nervous. Not that they're shady, but that it's more work for them.

A few more to add:
- In what ways would you consider the person who is hired for this position, a success?
- What key metrics have to be hit under what timeframe?
- What possibilities for knowledge expansion are available?

Your story reminds me of this valedictorian who came to the cold realization that it's all just a system to be gamed:
 

Digamma

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This is a pretty good resource that I will definitely try.

It works as a filter for stupidity, too - I have been a freelancer for a long time and I would nail all these questions because the spirit behind them is really transparent. If you fail them, you are not a genius.
 

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csalvato

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External locus of control immediately disqualifies a person for me.

That is a BIG one. You can usually tell in conversation if you're looking for it.
I definitely agree that looking for folks with an internal locus of control is important.

This can be tough, though, because most people looking for a full time job are likely coming from a situation in which their ability to control outcomes in the workplace was diminished. They felt powerless, or their complaints about things that were truly out of their control went unheard.

As a leader, it's important to empower your people and to look for the distinction between those who look to blame others, and those who are looking for something new, because the culture in which they operated was caustic (like @Real Deal Denver mentioned above).

If, as a leader, you can create an environment where empowered people can feel safe to complain about things with an eye to improving the company/situation, you'll see huge amounts of success.

A lot of people confuse complaining with a "victim" mindset, or someone who is "unsupportive", when really those folks can be the most valuable, introspective forces in your org.
 
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Kak

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I definitely agree that looking for folks with an external locus of control is important.

This can be tough, though, because most people looking for a full time job are likely coming from a situation in which their ability to control outcomes in the workplace was diminished. They felt powerless, or their complaints about things that were truly out of their control went unheard.

As a leader, it's important to empower your people and to look for the distinction between those who look to blame others, and those who are looking for something new, because the culture in which they operated was caustic (like @Real Deal Denver mentioned above).

If, as a leader, you can create an environment where empowered people can feel safe to complain about things with an eye to improving the company/situation, you'll see huge amounts of success.

A lot of people confuse complaining with a "victim" mindset, or someone who is "unsupportive", when really those folks can be the most valuable, introspective forces in your org.
I read this book a few years back and a lot of it's principles stuck with me. I found myself rereading it more recently.

https://www.amazon.com/dp/0470139889/?tag=tff-amazonparser-20

It helped me come up with a plan for opportunity ownership for my growing companies. Casually observing job folks, most companies have a system of hierarchy where people are kept in their place instead of encouraged to be better. They refuse to rock the boat. This is how you end up with GE and Sears.

At any KAK organization, my employees will be encouraged to create money saving, profitable and time saving initiatives. People all see the world differently. Sometimes all it takes is a change in perspective on one little thing to make a company way better. I'm never going to be too smart to hear my employees out about these initiatives and in fact I make it very clear that they will flat out share in the quantifiable improvements for the rest of their lives. Talk about a sweet retirement plan.

In contrast, managers that suppress or try to take credit for grassroots initiatives can F*ck off with no letter of recommendation.

I strongly believe in surrounding yourself with people smarter than you. Do it and listen to them.
 

Real Deal Denver

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Your story reminds me of this valedictorian who came to the cold realization that it's all just a system to be gamed:
Thanks for posting this. This guy is a genius. He realizes he was not the perfect candidate, and cites his weaknesses. By doing so, he actually demonstrates that he IS the perfect candidate. I just found a role model!

External locus of control immediately disqualifies a person for me.

That is a BIG one. You can usually tell in conversation if you're looking for it.
You don't think there are valid reasons for that? That kind of reminds me of when I was young, and I would seek help to deal with a bully. I was often times scolded myself, although I was the victim. Nobody likes a tattletale. What? Now that I'm an adult, I recognize this very flawed way of thinking, and I have called people out on it and call it what it is - a cop out. Shunning a helpless child to manage a situation beyond his control is nothing short of hideous. Doing it as one adult to another is pathetic. Nevertheless, that's what happened. Portraying that as external locus of control, if that might happen, is also a cop out. I would hope that you would probe into matters deeper before making a rash decision about that. Perhaps if I were smarter, I would be less honest about situations - and I know that - but I choose to be as honest and non-partial as I can be.

In contrast, managers that suppress or try to take credit for grassroots initiatives can f*ck off with no letter of recommendation.
That's rare indeed. At least in the parts of the world I come from. What usually happens is the best workers leave. The younger optimistic ones stay and suffer the incompetence. But only for a while.

I did experience a top sales person being demoted to running the warehouse in one company that had an exceptional CEO. He messed with people, and grew accustomed to having a teflon coating, and thus being above any reprimand. He did well for the company and himself, as he was very talented. But one time too many he crossed the line, and the boss lashed out. And draw blood he did. We were all very shocked at the severity of the decision. Everyone did better work from that point on because they now realized that punishment could be swift and severe. And everyone also had greater respect for the boss from that point on too! Unfortunately, the opposite (peter principle) is usually the norm.
 
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Kak

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Thanks for posting this. This guy is a genius. He realizes he was not the perfect candidate, and cites his weaknesses. By doing so, he actually demonstrates that he IS the perfect candidate. I just found a role model!



You don't think there are valid reasons for that? That kind of reminds me of when I was young, and I would seek help to deal with a bully. I was often times scolded myself, although I was the victim. Nobody likes a tattletale. What? Now that I'm an adult, I recognize this very flawed way of thinking, and I have called people out on it and call it what it is - a cop out. Shunning a helpless child to manage a situation beyond his control is nothing short of hideous. Doing it as one adult to another is pathetic. Nevertheless, that's what happened. Portraying that as external locus of control, if that might happen, is also a cop out. I would hope that you would probe into matters deeper before making a rash decision about that. Perhaps if I were smarter, I would be less honest about situations - and I know that - but I choose to be as honest and non-partial as I can be.



That's rare indeed. At least in the parts of the world I come from. What usually happens is the best workers leave. The younger optimistic ones stay and suffer the incompetence. But only for a while.

I did experience a top sales person being demoted to running the warehouse in one company that had an exceptional CEO. He messed with people, and grew accustomed to having a teflon coating, and thus being above any reprimand. He did well for the company and himself, as he was very talented. But one time too many he crossed the line, and the boss lashed out. And draw blood he did. We were all very shocked at the severity of the decision. Everyone did better work from that point on because they now realized that punishment could be swift and severe. And everyone also had greater respect for the boss from that point on too! Unfortunately, the opposite (peter principle) is usually the norm.
Just saying it like it is... You just know when someone isn't going to be a good fit. External locus sticks out to me like a sore thumb. I don't want that shit infiltrating and infecting my workforce.

You have highlighted a very specific set of circumstances. There are absolutely situations that are out of our control. Recognizing that doesn't necessarily mean the persons locus is external.
 

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It helped me come up with a plan for opportunity ownership for my growing companies. Casually observing job folks, most companies have a system of hierarchy where people are kept in their place instead of encouraged to be better. They refuse to rock the boat. This is how you end up with GE and Sears.
Possibly out of scope of this conversation, but I have a hypothesis that, given enough time, a large for-profit organization will begin to look more like government. Hopelessly bogged down by bureaucracy, zero incentive for people to perform, bullshit goals created by micromanagers, and no true mission to speak of beyond keeping their jobs. This doesn't even include the effect of having the entire American job-working 401k-stuffing public as your shareholder. The reason is multifaceted but a non-trivial one is hiring the type of people who are likely to want to build bureaucracy and call it 'productivity'.

Good insights, OP. One of the most frustrating things with freelancers is that the large majority of them, even if they have the skills, are complete BS.
 

Kak

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Possibly out of scope of this conversation, but I have a hypothesis that, given enough time, a large for-profit organization will begin to look more like government. Hopelessly bogged down by bureaucracy, zero incentive for people to perform, bullshit goals created by micromanagers, and no true mission to speak of beyond keeping their jobs. This doesn't even include the effect of having the entire American job-working 401k-stuffing public as your shareholder. The reason is multifaceted but a non-trivial one is hiring the type of people who are likely to want to build bureaucracy and call it 'productivity'.

Good insights, OP. One of the most frustrating things with freelancers is that the large majority of them, even if they have the skills, are complete BS.
Agreed. Good post.
 

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It all depends on what kind of work and project should be entrusted to a freelancer.

The available budget is the main discriminator to consider.

Up to a certain small amount it is better to choose by rating and portfolio directly published on the various sites of these services because it is a small risk.

I do not look at the character of the person but at the professionalism of the portfolio.

When the budget becomes important, the use of frelancers must be done with great care and parsimony.

I prefer to assume that dealing with freelancers for important projects for
the commandment of control.

In this case, the strategic questionnaire is welcome.
 

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