Often, I wonder why any manager with a functioning brain would hire sycophants to surround him or her, and what this tells about the business acumen of such and individual? Of course, as we all know that a manager who surrounds themselves with sycophants is making a strategic choice — but not a smart one.
And the choice reveals far more about their psychology and insecurities than about their business acumen. In fact, leaders hire sycophants when protecting their ego feels more important than protecting the organization. If one cannot tolerate dissent, challenge, being wrong or being questioned they will hire people who will never threaten their self-image.
Let’s say that it’s emotional safety masquerading as leadership. That kind of leader is Trump and the sycophant is Rubio, or Kennedy or Hegseth to name a few. If Trump had any self-confidence he would hire strong people. Instead, our insecure president hires agreeable people that provide him with constant validation, the illusion of competence, the feeling of being in control and a psychological crutch. It’s true that being surrounded by sycophants makes daily life easier.
There are no debates, no push-back and no uncomfortable truths to hear. The cost however is enormous with plenty of blind spots, strategic errors, group-think and stagnation. A president like Trump who surrounds himself with sycophants is signaling at least one of the following traits. Poor judgment as he can’t distinguish competence from compliance, alignment from flattery and loyalty from dependency.Fragile decision-making as bad news is filtered, risks hidden and mistakes unchallenged. Lack of strategic maturity as great leaders know they need dissent, debate, diverse perspectives and people who dare say “you’re wrong”. Finally a final trait is fear-based leadership, as Trump needs flattery to function, he’s not leading he’s managing their own anxiety.
Sycophants don’t gather around strong leaders but gather around leaders who need them, and that need is the real problem.










