Instead of hiring one Yes-man after the next, Charlie needs to invest in a respected team of “devil’s advocates”. He needs advisors who are strong, confident, honest and have the foresight to stop him before some of his bad decisions get off the ground. Charlie needs to surround himself with several leaders who’s primary job is to give him the potential negative downside of his policies rather than always painting the pretty picture. For example, employees will always find a way around poorly thought-out policies: DE&I hiring quotas, spans and layers, any reports or tally’s which are measuring and creating a competitive atmosphere around productivity/sales etc.
Charlie has fostered a Yes-man culture where those who get ahead are those who agree with him. Essentially, he keeps hiring himself over and over again.
The best leaders enjoy the intellectual sparring that comes from their peers and subordinates, where their beliefs and approaches are thoughtfully and intelligently challenged. They seek—and often demand—that their most trusted advisors regularly challenge their thinking. This is not done in some misguided notion of playing devil’s advocate just to be a contrarian, but with the expectation and assumption that their advisors will likely improve their thinking and ultimately yield a more well-rounded corporation.