Mining Our “Misfits” For Maximum Impact

I admit that what I’m about to write is a little weird, but its my weirdness so I think I’ll have a little fun with myself.   I woke up this morning (or maybe I was still dozing and dreaming) and thinking about the phrase “square peg in a round hole”. I turned it over in my mind and wondered why we don’t talk about a “round peg in square hole”.  This is where it gets weird … did I tell you I have a degree in mathematics? 🙂

As I was lying there, I started trying to figure out whether a square peg occupied more of the space in a round hole than a round peg in a square hole and began to work out the equations in my head.  Thinking about it now I seriously question whether these are the thoughts of a normal human being!! The winner, in case you are interested, is the round peg in a square hole, covering 78.5% of the area.  A square peg only covers 63.7% of a round hole.  Okay enough of the geeky stuff!

The idea of the phrase is also fascinating.  At, it is defined as follows:

A misfit. Its origin attributed to the 19th-century British philosopher and cleric Sydney Smith, the phrase has been used in a business context to describe someone who doesn’t fit in to corporate culture, isn’t a team player, and therefore stands little chance of corporate advancement.

When it comes to people, there is no such thing as a “perfect fit”.  When we go looking for people, we do try to look for people that align with our culture.  Yet we recognize that each is an individual and will have their own unique characteristics, similar to being a different shaped peg than the cultural hole we are seeking to fill.

I recognize this as a great thing.  If it were possible to find perfect fits then we would have no deviation from any norm.  That would be okay if our organizational culture were also perfect, but we all know that is never true.  I’m not trying to say that any existing organizational culture is anything like Nazi Germany (and I even hesitate to mention that part of history), but just imagine what might have happened if there were no Oskar Schindler‘s in that culture?

The questions we have to ask ourselves are along these lines. How much deviation from a perfect fit are we able to tolerate?  What shapes are acceptable to us and which ones aren’t? What do we need more of right now?

Let’s go back to our initial square and round peg examples and extend the metaphor.

  • SquareIf we select square pegs for round holes what do we get? First, we know that we get less coverage of our cultural norm as the math above proved.  We also get sharp corners or rough edges on the peg that may cause significant friction as it turns within the culture.  That’s the downside.  But when a square peg turns within its round hole, it is actually able to cover the entire area of the circle, meaning it can engage with the entirety of the culture and its values.  A square peg is more likely to be a change agent that will continuously challenge the culture to renew and refresh itself.
  • RoundThe counter example of a round peg in a square hole gets us different results.  The math works out better for us in this case because we get a better overlap between candidate and culture as the round peg fills more of the cultural hole.  When the peg turns it does so more smoothly and is likely that there is a lot of harmony in its relationships. But as it turns it covers the same ground and doesn’t reach into the corners of the culture.  The round peg has blind spots with respect the culture hosting it. That aside, such an individual can be an amazing cultural ambassador.

What this leads me to is our role as leaders.  We are the ones that make the hiring decisions, but are we executing those responsibilities with an awareness of cultural fit in mind?

  • Do we deliberately hire both round pegs and square ones, knowing their value to the organization?  Do we know what we need more of at any point in time?
  • Do we see our role as shaping of talent rather than direction of it, helping each with managing rough edges and blind spots?
  • Most importantly, do we know our own rough edges and blind spots and continuously work on managing them so we can be even better at helping others do the same?



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Ian Munro @

Ian Munro is a leadership and vitality coach with a primary passion for working with senior professionals who wish to improve their connection to and vitality in their career, or who wish to make a transition to a meaningful and rewarding retirement. His methods are focused on helping clients understand why they present as they do in day-to-day life, discover their authentic self and give themselves permission to build a meaningful and rewarding future, both professional and personal. Ian’s love for this work has developed naturally as he built his career as an executive and leader in the IT services industry, serving in many roles and facets of this industry over 25 years. As he reached the pinnacle of his career he began to search more deeply for meaning and alternate rewards from his own career and to begin to plan for his own “first retirement”.

One thought on “Mining Our “Misfits” For Maximum Impact

  1. Intriguing post. Early on in my business career I would hire people because of their skill levels. Sometimes there would inevitably be this clash with other staff members or management. I gradually understood how important it was that the hired person also should fit the corporate culture – especially ethics, morals and tolerance.

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