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When your 'square peg' can’t fit your 'round hole'

This is about performance expectations that are out of sync with capabilities and strengths. It sounds like this: “He knows what to do, so why can’t he just do it?” You’ve said it. I’ve said it. Leaders are notorious for falling into the quagmire of misreading what an individual is capable of executing and achieving. As a result, you place otherwise competent people into positions and situations where they struggle and flounder. In time, your frustration and dissatisfaction morphs a once confident and contributing employee into a demoralized and indifferent anchor whose weight is becoming increasingly difficult to drag along. The question is: When will you recognize that you just can’t get your square peg to fit in your round hole? Will you do something about it?

One of the most fulfilling aspects of being a leader is to coach and guide individuals to reach their full potential. We love to find diamonds in the rough and shape and polish them into sparkling gems. We can never allow our belief in the capabilities of others to achieve great things to be diminished. Next to our ability to dream, innovate and envision extraordinary companies, it is our belief in the human spirit that separates no-compromise leaders from mere taskmasters.


It’s when you allow your belief in the capabilities of others, shaped by your needs, priorities and objectives, without considering an individual’s actual aspirations and strengths, that you run into trouble. For example, you need a manager and you have a talented and high-performing employee. You proceed to “sell” this individual on the job, the possibilities, the income potential, that it’s the next rung on the success ladder. What you’re betting on is that the high performance and achievements that their natural strengths produced in one area will translate into high performance and achievements in a leadership role. Ladies and gentlemen - place your bets.

Recently I had two conversations with leaders who were so stuck in the square peg/round hole trap, they were allowing their companies to implode around them. One leader called me to discuss a long-term manager in whom she had invested tens of thousands of dollars in leadership and systems training. Periodic discussions to clarify expectations, concerns and next steps would show limited, short-term results. As frustration and indifference became more apparent, the manager’s attitude and demeanor deteriorated. Other employees and the leader walked on eggshells wondering what kind of mood would appear on any given day. After listening to story after story, I said, “I want to talk to that smart little voice in your head. Do you truly believe that this manager will ever be able to do the job?” The answer her smart little voice gave was, “No.” We discussed how she was stuck in the square peg/round hole trap and how, in the best interest of the manager, her team and her ability to lead, she needed to put an end to the situation so all parties can move on. She agreed.

The other conversation was with a business owner who expanded his company and, in the process, created an opportunity for a top performer to invest in the company and buy stock. The plan was to have his new partner lead one location while he channeled his attention on the new location. As in the previous story, he took his new partner through all kinds of business training. Well, the new location ramped up significantly slower than anticipated. Meanwhile, the partner found the accountabilities of being in full charge considerably beyond her natural strengths. The numbers side of the business was a black hole and leading a large team of service providers was quite different in real life. The partner struggled, employees got frustrated and departed for greener pastures, and revenues plummeted. The owner had his hands full with the new location. It was a scary and frustrating time for all.

I met with both the owner and the partner. We discussed the frustrations, challenges and leadership blockages. I coached them to build a realistic game plan. When I checked in recently, it was clear that nothing changed. The partner was the square peg and the leadership position she was in was the round hole. Once again, I asked the owner, “If you listen to the little voice in your head, what is it telling you to do?” His little voice was suggesting that it was time to save his partner (and the business) by reassigning her to doing work where her natural abilities can thrive. I’ll keep monitoring the situation to see if the decision is made.

It is so easy for leaders to get stuck in these situations and to allow them to drone on for far too long. Even with the best intentions and pre-screening, leaders can still discover that an employee is in over his or her head. It’s up to the leader to recognize the signs early and coach the employee to grow into the position. It’s the leader who must recognize and correct the situation before the damage and costs begin to pile up. Most importantly, the leader must “save” an otherwise valuable and appreciated employee from experiencing failure in a position of responsibility he or she was not prepared for and lacked the natural abilities to succeed.

Yes, leadership is a very complex game. Do you have any square pegs that you’re trying to fit into round holes?

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Neil Ducoff, Founder & CEO of Strategies and author of No-Compromise Leadership

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