Building Psychological Safety, Leading Across Generations, and Building Trust with a Skeptical Team [Office Hours #020]

Your questions. Answered.

👋 Welcome to a 🔒 subscriber-only edition 🔒 of our Office Hours newsletter. Every Tuesday, we tackle reader questions covering the most demanding challenges of management and leadership. (We share our best free content on LinkedIn).

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In this week's edition, we answer:

1. How do you build psychological safety on a team where people are hesitant to speak up or challenge ideas?

2. How do you effectively lead a team made up of multiple generations, each with different work styles and expectations?

3. How do you earn trust as a new leader when the team has had a bad experience with leadership before?

Let’s get started…

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Question 1:

Natalie from Johannesburg
How do you build psychological safety on a team where people are hesitant to speak up or challenge ideas?

Response:
Dear Natalie,

Psychological safety is the foundation of innovation, inclusion, and engagement. When people hold back their ideas or concerns, you’re not getting their full contribution—and over time, trust and morale suffer. Creating safety doesn’t happen with one speech; it’s built through consistent signals that say, “You belong here, your voice matters, and it’s safe to be real.”

1. Model Vulnerability and Openness

As a leader, your behavior sets the ceiling for how open others feel they can be. Share your own learning moments, doubts, and adjustments:

"I missed the mark on how we handled that last sprint—I’ve reflected and I’m adjusting our approach."

This shows that imperfection is not only tolerated—it’s part of growth.