Why the Best Boss is Hard to Work For

November 13, 2018 By Alysha Willden

The best boss is not the easiest to work for. They are challengers, are results-driven, and know the capabilities of their team. Working for them is not always a walk in the park, but the growth that comes as a result of their leadership is invaluable.


As I look back on my career, some of the best bosses that I worked for were the hardest to work for. My favorite boss wasn’t the one who I most agreed with, nor was she my favorite boss at the time. But looking back, I learned and grew the most working for her.

They Are Challengers

In her book, Multipliers, Liz Wiseman details the common characteristics of effective leaders that, in turn, get more out of their teams than they ever thought possible. My favorite of these characteristics is the challenger.

Without spoiling too much, a challenger leader pushes their team until just before the breaking point. Like a rubber band stretched to the max, oftentimes this is uncomfortable for the employee, forcing them to work harder, think smarter, and ultimately learn to solve seemingly impossible problems.

This is where the growth happens. As Michael John Bobak says, “All progress takes place outside the comfort zone.” The best bosses and leaders are those that consistently force employees to step out of the comfort zone and try. That’s precisely why they’re the hardest to work for: it’s uncomfortable to work outside the comfort zone.

They Are Results-Driven

When successes occur, a good leader celebrates with their team, but also analyzes the decisions and measures that got them to the achievement. When mistakes happen, they do the same. Consequently, their team members are asked to do the same— to critically analyze the driving factors for their own successes and failures, as well as their team’s. This rigorous analysis can be tough on employees, but is what makes the difference between recurring mistakes and recurring successes.

They Know the Capabilities of Their Team

Good leaders know the capabilities of their team. The best leaders can see the potential for their employees and help drive the growth of their team to help each employe reach his/her potential. Because they see the possible, they push their team to make it happen.

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