Terrible Bosses, Culture Alchemy and Entrepreneurship

Terrible boss

That kind of boss


Before you start reading, I want to point out that I’m not describing any of the bosses I’ve ever worked for; they have all been great. I’m writing this for a friend…

I’ve often heard that corporate culture comes from the top, and, in my experience this has been true. This doesn’t mean company culture is homogenous, there can be rebel islands espousing a different ideology than that found in the rest of the cubicles. I’ve encountered organizations with cripplingly low employee morale in every department, except for the executive suite and the sales team. While employee churn was reaching all time highs, the sales team was in high spirits, hitting their numbers and enjoying their work life. This sales team was being propped up by a great leader who was deflecting the prevailing culture.

Creating a counter culture comes with it’s own complications. Corporate culture is a subtle thing, inserting foreign objects affects the whole body. In this case, the positive culture of the sales team had a negative impact on the overall organization’s culture. This negative impact would manifest in the interactions between sales and other divisions of the company: poor communication, slow turnaround times, hostile interactions, etc… This island of positive corporate culture was becoming a poison pill for the overall culture of the company!

The solution to this culture clash was just short of genius. The competent even tempered head of sales was replaced by a hostile, prevaricating, megalomanic with anxiety issues. In an instant, the island of happiness became the pit of Mordor, and the overall culture of the organization started to improve. After all, “at least my department doesn’t report to sales” was often heard whispered between newly uplifted employees. Best of all, the sales team had a 100% churn in just a few months. Out with the old.

This is a win-win story though, because the sales team that left all went on to new challenges: taking over global teams, joining successful startups, starting their own companies and more. The truth is, the first boss, though better in every way, wasn’t just propping up the team, they were keeping the team from realizing their careers would flourish elsewhere.

If I was one to beat an analogy to death, corporate culture is like a river, so, if you find yourself on an island, ask yourself if you’re going the same direction as the rest of the company.

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