Leadership and Main

Bettering Others and the World You Live In

Square Peg, Round Hole

square peg round hole

Square peg, round hole is one of my go to phrases in moments of frustration.  It enters my mind and accelerates to the tip of my tongue in those moments.  I am grateful that it tends to stay there…most of the time! 

There was a toy that most of us played with in our infancy.  It was a simple, wooden toy.  The toy set included a wooden mallet, three different shaped pegs, and three correlating holes.  The set is complete with a round peg, round hole; star peg, star hole; and square peg, square hole.  The intention is that each one fits in its respective hole. 

We are going to focus on one of those pegs with a misshaped hole in this week’s post.  Let’s dive into four things we can learn from the experience of trying to fit a square peg into a round hole:     

Forcing Things

You are not going to squeeze a square peg into a round hole unless you force it.  You can take the hammer and bang away at it until one of three things happens: the peg breaks, the hole breaks, or the entire toy breaks. Forcing it just won’t work.  It defeats the objective of the toy and takes way too much effort as well.

It is easy to try to force things in leadership. Why? Because we want our desired outcome so bad that we will do whatever we can to make it happen. We will use tools like persistence, control, and pride to try to force the outcome we want. The more we press, the more damage we do to the end result.   

Complicating It

This toy is designed for small children. Toys like this are intended to be simple, not complex. The round peg, goes in the round hole…star peg, star hole….and you guessed it, square peg, square hole. As simple as it gets, no other combination works.

I have long considered to put one of these toys on my desk. That way whenever the team or I complicate things too much, we just simply pull it out as a reminder that we are overcomplicating things.

In the world of leadership, we do a really good job of complicating things. We make mountains out of mole hills.  When simplicity is the solution, we drift into complexity. There is a lot to be said about the adage, “Keep it simple, keep it stupid.”  Solutions are found in simplicity.

The Right Fit

The objective of the toy is to find the right fit. Placing the right peg in the right hole makes utilization of the toy much easier.

In the world of leading people, finding people that are the right fit for the team is critical to organization success.  From a culture standpoint, if someone isn’t the right fit, you are trying to fit a square peg into a round hole. It ain’t going to work.  Both you and the team member will end up frustrated, guaranteed.

This is why it is so important to work hard up front to make sure the fit is right.  I once heard that you should hire slow, fire fast.  Taking the time in the hiring process significantly increases the chances the prospective team member fits.  Then, if you realize the person doesn’t fit the culture, be prepared to make a tough decision.   

Repeating Bad Decisions

I have coached youth wrestling for a long time. In wrestling, an excellent example of repeating a bad decision is reaching back. When you reach back from the bottom position, you tend to get pinned. Getting pinned is not good. 

After a few times of the same kid counting lights in the gym, I would remind them of this little example.  I asked them, “if your mom or dad is cooking dinner, you reach up, touch the stove, and burn your hand, would you reach back up there and touch it again?” After a little bit of awkward silence, I tended to answer the question for them with, “no you wouldn’t!”

Ever catch yourself or your team repeating bad decisions or drifting back into bad habits? Albert Einstein once said, “The definition of ‘insanity’ is doing the same thing over and over again and expecting different results.” Pride, control, curiosity, or whatever the cause, we just keep trying to fit the wrong peg into the wrong hole, wasting time and energy. As humans, we just can’t help but reach up and touch the hot stove one more time.  Insanity!


Now, whenever you reach your moment of frustration, just remember, square peg, round hole!  It’s almost therapeutic, trust me!  Just use your inside voice when you say it, that will keep you out of trouble!

I am a big believer that leaders need to create space.  Space is created in simplicity, not complexity.  Too often leaders find themselves in a world of busyness that inhibits their ability to create space. 

The beauty of being a kid is life is simple.  There are no bills to pay, no responsibility, no pressures of time, and no people to lead.  We grow up, become leaders, and lose the ability to simplify our worlds.

Slow things down and put the right peg in the right hole.  If the peg fits the hole, it frees up the time and energy we need to lead our teams well.  When our worlds get complex, just remember…square peg, round hole.      

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