Why Hiring Is Like Playing Blackjack, And 3 Rules To Increase Your Odds of Success

Hiring is like playing Blackjack(Part II of a two-part series on Leadership and Team Building –click here for Part I)

Once I made the decision to give up the control I worked so hard to get, and become a leader instead of a micromanager, the next step was building a team that I could trust to get the job done.

Finding the “right” people has always been one of the most challenging things a leader can to, and it often can be the most frustrating, because when you get right down to it, it’s a lot like playing Blackjack in Vegas – by following the right rules and being disciplined about it you can reduce your odds of failure, but in the end, you can never reduce that risk completely, even if you think you’ve been dealt a winning hand.

Consequently, my approach to hiring has evolved into a quest to keep my batting average as high as possible, knowing I cannot do it perfectly, by following three basic rules.

The first one is something one of my old bosses said to me many years ago.   I was asking his advice on a major hire I was about to make, and as he filtered through the resumes I had handed to him, he suddenly stopped, looked me straight in the eye, and said,

“My dear boy, if you ever learn one thing about doing this, here it is: Never, ever, be afraid to hire somebody smarter than you are”

This advice couldn’t have come at a better time, because I had just come out of my “control” phase, which by its nature had put me in a place where I thought I could do everything better than anyone else.

On top of that, there were human insecurities at play – let’s face it, it takes a lot of intestinal fortitude to hire someone you consider more talented.   They are immediately a threat to your often fragile ego.

But it was a rule I knew I had to follow.

The next rule is to find people who have the courage to express their opinions, both intelligently and respectfully.

Another trap I found all too easy to fall into was putting a bunch of “yes people” around you.  It’s great to get that kind of validation, and I know I’m pretty forceful in my opinions, but I’m far from always right.    I need to be tested, and I’d prefer to have it done by those within my own team.

The type of hires that fit this description are the ones that are clearly comfortable in their own skin, with a confidence that approaches, but never crosses, the line of arrogance.  And for me, it must be combined with a “statesmanlike” ability that comes from a natural application of the Golden Rule.

Lastly, I like to hire people that set high goals and standards, and are the first ones to tell you they aren’t hitting them. In other words, they are harder on themselves than I ever could be.

I call them “self-regulators”.  They come with an additional bonus – they aren’t afraid to tell you the bad news that you really need to know.

If I can keep to these three rules, I will make good hires, although, just like at the Blackjack table, there are times when they won’t be so good in the end.  It’s just not a perfect science.  I can’t be dealt 21 every hand.

But I’ll be successful enough to easily survive the failures – and stay on the road to greatness.

And I’m confident that if you follow these rules, you’ll be able to stay on that road too.


  1. Mary Beth Wilkerson says

    I teach a hiring class at my company and would love to use this advise if youa re okay with us posting your link to our site.

  2. Joan Marie says

    The greatest challenge I find is determining these characteristics in the selection process. Not being afraid to hire someone smarter than you is ok, but how do you determine that some REALLY sets high standards/tells you when they aren’t hitting them/is a self-regulator. People in interview often will talk to this, but in reality don’t work like this, and you find this out a couple of months later after you’ve given them time to settle in. Suggestions for how to determine this in selection would be appreciated!

  3. says

    The problem with the interview process used in most companies is that it is extremely time-consuming and often ineffective. Hiring is a three step process.
    1. Review the resume’ for competencies and experience or desire to succeed.
    2. Create a form with standard questions and conduct a BRIEF 10 minute interview to get a “sense” of the individual.
    3. Administer a pre-hire assessment that measures behavioral traits and skills. We use the Prevue Analyst-Link (www.prevue.us)
    The assessment provides an unbiased “third party” opinion and allows us to focus on top candidates instead of wasting time on endless interviews. In addition we use the assessment report as part of the on-boarding and training program for new-hires. This is facilitated by their manager and is instrumental in building a “Communication Link” between the manager and new-hire. It is the key to reducing turnover.

  4. says

    Thanks Ann, Joan, Scott, Mary Beth, Wendi and Pat for your comments.

    I appreciate the kind words, and the additional thoughts (Joan, yours on “how” to determine these things in an interview is especially good – I need to address that in another post, although that’s why I likened hiring to gambling – sometimes you are just guessing)

    BTW Ann, I also advocate pre-hire assessments, but use a different one.

    Thanks again to you all, and all the best!


  5. says


    Great post! I love the first point, “never be afraid to hire someone smarter than you”. That’s a good sign of a leader – knowing that your team brings more value as a whole, not just from one perspective (the boss). Your other points hit home as well and will continue to push me to be a better leader myself.

    Keep up the great work!

    Kirk Baumann
    Campus to Career


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