As a leader, I always encouraged my team to challenge the process. I actively invited them to question me and speak up when they disagreed. It was a requirement to be part of my team. Yet, despite this encouragement, it was still difficult for them to speak up.
I worked on creating as much psychological safety as possible, allowing people to share without fear of retaliation. At the same time, I expected an environment where robust conversations were valued and not avoided for “getting along”. Still, it was a challenge.
For many of my team members, it was their first experience in an environment where openness wasn’t just allowed but actively encouraged and required. Clearly, how easy is it to tell your boss her idea sucks? Many CEOs complain about never being truly challenged or contradicted by their C-Suite.
The first step toward transparent and constructive conversations is encouraging feedback. A fun example from my experience: one of my direct reports, whom I valued for his intelligence, pointed out that my facial expressions had sent the wrong message. When he shared suggestions, my face was so intense that it gave off a vibe of, “What are you talking about?” In other words, I looked unintentionally mean and scary. I was hyper-focused.
After becoming aware of this, I could feel myself making that expression again. A minor adjustment, a slight smile at the corner of my lips, was all it took to change how I was perceived. It even became a fun inside joke. Whenever he frowned, I’d say, “I’m doing it again, right?”
Leaders and managers must understand that speaking up to hierarchy is challenging, generates fear, and needs encouragement. The good news is that when trust is established and psychological safety is genuine, the courage to speak up becomes contagious.
