Thoughts on Hiring

Big Red Car here in the beautiful ATX. Just when you thought it couldn’t get any better, we have a day like today and a day like yesterday.

On Earth as it is in Texas!

Hiring is one of the things about building a great startup that is alluded to with a backhanded swipe of the founders’ hands.

It is an essential consideration. [Do tell, Big Red Car. Give us more, please.]

Hiring characters

Hiring is like writing a character into a novel. Your high school creative writing teacher told you that characters had to be “deep” and warned you against allowing them to have the fatal flaw of being “one dimensional.”

When you got to college, you learned that characters had obvious or exterior characteristics, traits, habits and quirks. Love those quirky traits. Things you could see with your eyes. You could tell the bad guys by their appearance, right? If you were watching a movie, you knew the bad guys were coming when the soundtrack got ominous.

But what really drove them was their backstory, their interior drivers, the meaning they attributed to life. The “why” of what they actually did. These are interior considerations.

Then you had to deal with their actual behaviors. Their actual behaviors might conflict with their exteriors and contradict or be driven by their inner demons. The conflict between their competing qualities is what made the story interesting. Storytelling is all about conflict. Creating it and resolving it. Then John Wayne gets the girl and rides into the sunset, right? Wrong.

Life is all about conflict. Good hiring is about conflict. The conflict between what the applicant thinks you want in the hire and who they really are. You want to hire the real person, not the faux, manufactured person. But how do you find that person?

Characters and applicants are complex

Characters and job applicants are a combination of:

1. Their obvious characteristics which can be viewed and sensed by the interviewer. It is what you see and the caution is this — what you see may not be what you get. The wild rebel who is going to wreck your culture may look very meek in her perfect interview dress. And guess what, you may get fooled by him. [Big Red Car crossdressing joke. Totally inappropriate but a little provocative nonetheless. When you sit in a driveway all day, sometimes you write truly stupid stuff. Sorry.]

2. Their interior driver, their personal backstory, the why of what they are and want to be.

3. Their actual behavior and whether it is consistent with their obvious characteristics and the “why” of their lives. Is it consistent? Does it contradict? Most importantly, how does it correlate with the exterior and the interior of your applicant?

OK, Big Red Car, how do we get so deep into our applicant? How do we find out their backstory and their behavior? Sheesh, Big Red Car, this is complicated. Isn’t it? Why can’t I just get them to fill out an application, talk to them for ten minutes and hire them?

Because, dear reader and CEO and entrepreneur, you will make a lot of bad hires. Hiring is one part dodging bullets and one part finding rock stars. You have to do both.

Know this, you can do it if you will harness that big brain of yours. You can do it.

How to get the exterior right

Most hiring processes — wait, you do have a “hiring process”, right? — do just fine on the exterior characteristics, the obvious stuff.  Your eyes and ears will tell you what you need to know.

The applicant’s resume — more than fifty percent of applicants will tell you a lie in writing on their resume — will help you on this matter.

Look at the above link to get a framework as to how much baloney gets baked into resumes. It is frightening. Know this.

How to get the backstory

Getting the backstory will not be accomplished by asking:

“What do you consider to be your greatest shortcoming?”

[Well, unless the question is administered using waterboarding techniques but that’s a more advanced lesson.]

“My greatest shortcoming is that I am impatient when striving for excellence and, at times, I work way too hard.”

Bullshit meter clanging at your end yet?

To get to backstory, you will have to creep up on things with questions that delve into their personal view of life. After all, you are trying to find out how they view life and what it means and how it drives their behaviors. You are ultimately hiring their behaviors. Remember that. It will ultimately be what they do for your company that counts.

“Do you read much? What books? Best book you’ve read recently? How do those apply to what you do?”

“What is your favorite movie of all time? What lesson did you take from it?”

“Is there a particular public figure you admire? Why? How would that apply to your life?”

“Favorite teacher or coach? What did they teach you and how do you use it today?”

“What would you change about your upbringing, if you could?”

“What are your favorite charities and why?”

“If you could invite anyone to a dinner party who would your first three invitees be and why?”

These questions are not brilliant, in fact, they are a little predictable and mundane but they are the way you are going to get them to talk about the things that are a little below the surface. You are looking for the “why” of each of these questions. You almost don’t care about the actual answer, you care about what it reveals as to why your applicant does things. What is driving your beloved candidate?

There is no silver bullet; there is only hard work. Remember, you are probing and if you are completely rebuffed that also tells you something.

Probing for behavior

The first quest in trying to detect how the exterior and the interior melds and drives behavior is simply checking references.

Don’t ask questions which are going to elicit knee jerk favorable or unfavorable answers. Probe with questions that will elicit anecdotes or descriptions of behaviors. Get their former employer to tell you what they did.

[Pro tip: Make damn sure you know why the applicant left every job and how they got their next job. This junction at the end of former jobs and the beginning of new jobs is a critical point of observation. It may be a pivot or inflection point and the answers may provide incredible insights into the “why” of it all. Know the answers.]

Ask “what if” questions that force the applicant to come up with answers that are based on their instincts and inclinations. You are probing for how their exterior and their interior will work together in a real world situation. In some ways, this is a lab experiment.

“If you were faced with this situation, how would you deal with it?”

“Someone did this in reaction to this, would you do the same thing or how would you do it differently?”

Make the situation very close to the actual job they will likely be doing. Follow their most instinctive answer, don’t pay too much attention to what bubbles up five minutes later when they’ve quashed their instincts and are trying to model what they think you want to hear.


The Big Red Car counsels that job interviews should be a little structured and process driven. Not that the applicant is going to know this.

Write out your questions and group them under the appropriate headings — exterior, backstory, behavior — and weave them together in such a way that the applicant doesn’t figure out: “OK, here come the backstory questions. Must have read that goofy Big Red Car blog post.”

Remember always you are hiring complex people but you are hiring their entire story — their characteristics, traits, habits, quirks; their backstory and drivers; and, their behaviors. The first two just combine to become their behaviors.

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car. Hire well. Be kind to yourself because you, my friend, you are a very complex character and you are the one writing this story. Hire well.






14 thoughts on “Thoughts on Hiring

  1. Best interview I ever received was in a background investigation for a b.s. state dep’t internship I had one summer in college. The interviewer was a retired FBI agent who said he did this on contract for extra income, and was not that busy. So in spite of the nearly complete lack of access to any classified material on my part, he spent the better part of 4 hours having coffee with me and gradually working up to the tough questions. I’m pretty sure by the end of the interview, I had divulged my deepest, darkest secrets. Which, being 21 at the time, were not that deep or dark. But still, I would not have opened up without that skillful manipulation.

    I’ve subsequently been interviewed several times as a reference for friends pursuing various agency jobs, and have been sorely disappointed with the quality of the supposedly professional background reviewers. Most seem to just go down a list of check-the-box questions.

  2. Yes, we want to hire effective people and
    realize that some of what makes a person
    effective is their personality
    ‘internals’. So for a candidate in the
    hiring process, we want to understand
    those ‘internals’ and then use that
    understanding to predict the candidate’s

    Some concernes:

    (1) Understanding such ‘internals’ is
    difficult under the best circumstances.
    E.g., a Ph.D. in clinical psychology with
    20 years of experience and an hour a week
    for a year with a candidate usually has
    difficulty. A hiring process stands to
    have more difficulty.

    (2) Even if we have some of the best
    understanding of the internals, a standard
    remark in the social sciences is that such
    understanding has little predictive value.

    I came to understand (1)-(2) after “paying
    full tuition”.

    So, at this point I’m guessing that a
    better approach is to design the jobs so
    that we do not really need to have good
    predictive value from understanding
    personality ‘internals’. If this guess is
    correct, then mostly we should design jobs
    so that the work that needs to be done,
    the background needed to be able to do
    that work, and our ability to evaluate
    that work are all relatively simple so
    that trying to understand personality
    ‘internals’ and getting predictive value
    there is less important.

    I’m reminded of the movie ‘Moneyball’
    where the scouting and coaching staff keep
    giving long lists of subtle things wrong
    with various players in style, their
    personal lives, etc. but the General
    Manager Billy Beane keeps saying “they get
    on base” and don’t cost very much and
    ignoring nearly everything else.

    Thus I conclude that the interview process
    is mostly to look at education and
    experience. Sure, if there are some
    obvious, serious red flags, then look at
    those and maybe let them be a reason to
    reject the candidate. But trying to
    understand and make good use of deep
    personality ‘internals’ in the interview
    process I have to chalk up as nearly

    To some extent we can evaluate the
    internals and make good predictions based
    just on what we can clearly observe about
    just how well something works; if it works
    well, then, if we wish, we can conclude
    that the internals must be at least good

    So, if a candidate has done well with
    education and experience and there are no
    obvious red flags, then that is about as
    much as we can hope to know about the
    internals and their predictive value.

    But maybe I see two ways to get by without
    much attention to personality internals:

    First, one of my suspicions is that most
    people need a good, maybe even formal,
    structure where they know in fairly clear
    terms what they are to do and how they
    will be evaluated and get praise and
    approval and financial, career, and
    emotional security.

    Second, in addition most people can do
    much better given some good leadership.

    One question would be, what does the US
    military do about understanding
    ‘personality internals’?

    There were some interview questions.

    Q. “What is your favorite movie of all
    time? What lesson did you take from it?”

    A. In movies, I like (A) history that
    explains things, especially some
    surprising causes, (B) characters that give
    examples of how people can be, especially
    women, (C) stories with intricate puzzles.

    So, ‘Gone with the Wind’ shows Scarlett
    O’Hara being a surprisingly determined to
    be an extreme Southern Belle and
    narcissistic, ditsy, destructive bimbo, Rhett
    Butler being surprisingly slow to see how
    bad Scarlett really was, and how fast and
    foolish the South was to pursue the war.

    ‘Fat Man and Little Boy’ for how
    Oppenheimer did really well through lots
    of silly, practical obstacles just getting
    it DONE.

    ‘Winds of War’ to see how shockingly eager
    the German people were to support Hitler,
    how determined Hitler was to be a total
    nut job, how foolish he was in
    overreaching, and how have to suspect that
    he expected to fail and even pursued
    failure, how content Goering was to have
    only a short range air force, how well the
    German army fought while being asked by
    Hitler to do too much too fast with too
    little, how many submarines Germany lost,
    how bad the Germans were at cryptography,
    how bright the supposedly ‘stodgy’ British
    were at code breaking, radar, fighter
    planes, and long range bombers.

    ‘Tora …’ on how slow the US was to make
    use of the rock solid intelligence they
    did have. Or, why the heck bother to try
    to detect the enemy coming if are going to
    assume that any detection signal is a
    false alarm? This lesson has fairly
    general utility. Heck, taking the
    detection seriously, the US had a good
    shot at shooting down all the Japanese
    planes and then going after the Japanese
    carriers, especially since the US carriers
    were already at sea.

    ‘Midway’ on how much the US got from code
    breaking, how bad the Japanese were at
    intelligence, cryptography, and making
    good command decisions quickly under
    broken plans, and how determined the US
    Navy was to exploit the code breaking and
    resulting intelligence, take risks,
    emphasize winning, and accept the costs.
    More of interest was in just how bad the
    US Navy planes were at navigation and
    having fighter cover for the dive bombers
    and torpedo planes. Some of the US
    execution was really bad; bad execution is
    bad stuff quite generally.

    ‘The Sting’, ‘The List of Adrian
    Messenger’, and ‘Witness for the
    Prosecution’ for some tricky puzzle

    ‘Captain Kidd’ (1945) for a master class
    in manipulation and duplicity or what the
    heck the other guy might be doing to you.

    ‘The Adventures of Robinson Crusoe’ (1954)
    for insight into what a man might go
    through when alone for a long time.

    ‘Back to School’ for how a bright,
    determined, successful guy in business
    swaps some of live’s lessons with a
    college faculty.

    ‘Absence of Malice’ for how eager people
    can be to convict a son due to what his
    father had done and how silly, foolish,
    lost, confused, driven, and destructive
    the ‘feminist’ reporter was — good
    lessons on what might happen.

    ‘Moneyball’ for how much determination and
    guts it took for Billy Beane to set aside
    traditional baseball evaluations, how
    clear was the depiction of the resistance
    of baseball to anything new, and how
    clearly the owner of the Red Sox saw the
    lessons of Beane’s example. Those lessons
    likely apply to more than just baseball.

    ‘Khartoum’ for the suggestion from Gordon
    that being afraid of death gives up a lot
    of power; that point has to apply both to
    self and to adversaries.

    The old ‘cinema noir’ ‘Impact’ for the
    extreme contrast of the two women, one who
    pulled miserable defeat from the jaws of
    magnificent victory, all for no good
    reasons, and the other who pulled
    magnificent victory from the jaws of easy
    defeat, for all the best reasons. Another
    lesson was that the poor guy was a dummy
    not to see the truth about both of those

    Q. “Is there a particular public figure
    you admire? Why? How would that apply to
    your life?”

    A. D. Eisenhower for how important it is
    to have integrity, determination,
    prudence, and insight into people and to
    keep up with history and technology.

    Q. “What are your favorite charities and

    A. Mike Bloomberg’s — he has a shot at
    helping really significant progress in
    medical science. James Simons, for his
    help pushing forward interest in
    mathematics and science.

    • .’
      Once you start to hire at the education level of someone like you, the rules change a bit. My advice is intended for the startup world in a general sense.

      Having said that, your responses to those questions would have been sufficiently enlightening — not “sufficiently” perhaps “perfectly” is the better word — that I would have been interested in hiring you because of the clear depth of your mind and the quality of your ability to see into the intellectual depths.

      Now if you didn’t have that one gun charge . . .


  3. It can look like a big red car, but does it drive like one? At the end of the day, only a long drive will tell about the real engine, even a mechanic can be fooled. A luxury we often do not have while hiring !

    • .
      Nothing drive like a Big Red Car.

      Use probationary employment periods of 90-180 days to ensure that you have a good fit.

      Firing fast is almost as important as hiring well in the first place.

      Resist the temptation to do missionary work. If it doesn’t work, move on and don’t wring your hands as to why. Treat everyone fairly but cut the ties and move on.


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