Bad Bosses, Better Leadership, and Calling Your Own Shots with Steve Jorgenson

Steve Jorgenson (see bio below) has had an interesting career.

Law school. An MBA. Government contracts. Staffing and recruiting. Entrepreneurship. Hockey. Rugby. Remote work around the world.

And more than a few bosses who provided excellent examples of how not to lead.

In this conversation, Jeff talks with Steve about growing up outside Chicago, being a spectacularly unenthusiastic high school student, eventually earning both a JD and MBA, and navigating a career filled with difficult managers, big responsibilities, entrepreneurial swings, and a few hard-earned lessons.

Steve shares what it was like managing a $200 million government contract in his twenties, building trust with an employee who initially wanted nothing to do with him, and repeatedly finding himself in workplaces where truth-telling and new ideas were not always welcomed.

He also talks about launching his first company, learning some painful lessons when business partners betrayed his trust, and why those experiences helped shape his newest venture, Poach Prevent, a company designed to help businesses protect themselves from having recruiting partners poach the very employees they are being paid to help hire.

Along the way, Steve explains why the best boss of his career earned his trust by giving him room to do his job, why managers should be resources rather than roadblocks, and why great leaders give credit away instead of hoarding it like leftover Halloween candy.

This is a conversation about bad bosses, good leadership, entrepreneurship, trust, resilience, remote work, career reinvention, and what happens when you finally realize work does not have to feel miserable.

And yes, we also cover rugby in Ireland, hockey dreams, hip replacement at 35, working abroad with your spouse for months at a time, dog summer camp, signing a contract with the NHL, and canceling a $600 wing-walking adventure because apparently standing on top of an airplane without doing barrel rolls was not exciting enough.

This episode is brought to you by... Pelaccio & Partners. Ever wish your company updates could be less “quarterly earnings report” and more “late-night talk show”?

At Pelaccio & Partners, we help leaders stay connected to their people as their organizations grow. We create internal podcasts that make leadership communication more human, give employees a voice, and help build a more connected and engaged workforce. Think less corporate broadcast. More conversation people actually want to hear. Whe