A Tale of Two Bosses

A Tale of Two Bosses

Paula and Alexander, two old friends who knew each other from University, meet up for dinner after realizing they've been in the same city for quite some time. They both work for large tech companies in a similar role. Paula tells Alexander that she absolutely dreads going to work and dealing with her boss and is surprised when Alexander doesn't feel the same way—he likes his boss. 

Paula is stopped in her tracks. Aren't bosses always bad?


Paula's boss, Simon, paved his way to middle management by performing well in his previous roles. His coworkers, many of whom have been there as long as him, were surprised—while Simon does get his tasks done, he never interacted with other employees, never showed any passion for the position—yet his ability to do well in his initial role pushed management to promote him.

Simon barely knows Paula. When she joined, he introduced himself, laid out the expectations of her job role, and told her to ask him if he has any questions. He is rarely around and expects Paula to get her job done in the same manner that he did—failing to recognize that her doing the job a different way is more efficient and better for both her and the team. He gives Paula constant criticism, even when she is performing well—after all, that's the way he prefers to be managed, so he figures that's what everyone wants.

After the first few weeks, Paula had wondered if there was something wrong with her—did Simon not like her? However, after talking it over with other teammates, she found this was classic Simon. He rarely communicated with the team and never held 1 on 1's. He would lay out a timeline for a project but never check back in. He never connected a project to the company's broader vision. He didn't help the employees set goals—for the company or their career, and was always shocked when things fell behind or didn't go the way he wanted to.

Paula enjoyed her role and her teammates and loved the company's mission—but she did not love Simon.


Alexander's boss, Kristen, is kind of a legend at her company. Not only did she consistently perform well in her roles, but she was always coming up with new ideas, bringing the team together, and empowering others—even in her early days when she was working an entry-level position. 

As soon as Alexander joined the team, Kristen immediately welcomed him in. Their first meeting wasn't about all the onboarding technicalities—Kristen wanted to get to know him. How was he best motivated? How did he best learn? What qualities did his previous bosses have that inspired him to do his best work? 

Kristen has kept her promises and has continued to be the best boss Alexander has ever had. The team always has a clear vision of where they are going—for every project, individual or team-oriented, Kristen always helps set goals and deadlines. She checks in on the team as needed, with frequent one-on-one's, but knows when to pull back and let her team take the reins themselves. Every project or task the team does is connected back to the vision of the company. 

Alexander enjoys his role and is even more empowered in it with Kristen as a boss. He lets Paula know that if an opening ever comes up on his team, he'll tell her. 

A few weeks later, Paula's brother has a medical emergency, and she needs to miss a bit of work. Simon shows not a single ounce of compassion—when she lets Simon know that she has to head out for the rest of the day, he grunts and tells her that this will count as a day off if she leaves early. Paula leaves anyway, and when an opening comes up at Alexander's team, she jumps on the chance to go.

As the saying goes, people leave bad bosses, not bad jobs.


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