Sunday Musings Curate The Right Environment

Happy Sunday Friends!

Hello Friends! Here is 1 quote I’m musing on this week, 2 ideas, 3 of my favorite things from the week, and 1 question. If you find it useful or interesting, please start a dialogue with some friends or others! I’d love to hear about it.

One Quote I’m Musing

“A wise man can learn more from a foolish question than a fool can learn from a wise answer.”

| Bruce Lee

Have you ever stopped to consider whether your work environment is truly as supportive and empowering as you believe it to be?

Often what we think, and the reality of our workplace culture can be two very different things. We might think we've fostered a space where people feel confident, secure, and empowered. But the true test comes in high-pressure moments when people either trust the system—or hesitate.

I've been traveling for the past two weeks (DC x2, Maryland, California), and in my travels, I encountered a situation that spotlighted this. A person responsible for a small (but essential) aspect of our trip was unusually cautious, they needed additional documentation and approval from someone else before proceeding.

This was a key identifier in my mind. This wasn’t about mitigating actual risk—nothing in the process suggested that an additional review was needed. Instead, their reluctance seemed rooted in fear—fear of making the wrong call, of stepping outside the lines, of making themselves vulnerable rather than embracing the trust the system was designed to provide.

This behavior isn’t uncommon. It’s a symptom of an environment where psychological safety is lacking. People in these environments hesitate to ask questions, admit when they don’t know something, or make decisions confidently. They play it safe—not to protect the mission, but to protect themselves.

How Do We Recognize These Symptoms?

• Hesitation & Bottlenecks – Employees constantly seeking approval, even for minor decisions.

• Fear of Mistakes – A reluctance to take calculated risks, leading to stagnation.

• Lack of Initiative – People doing only what is required, nothing more.

• Silence in Meetings – An absence of questions or challenges, signaling a culture where people don’t feel safe to speak up.

What Can We Do About It?

1. Model Curiosity and Vulnerability –We openly ask questions, admit when we don’t know something, and encourage others to do the same. When people see leadership embracing learning, it normalizes intellectual humility.

2. Reinforce Psychological Safety – Encourage decision-making within defined frameworks. Provide constructive feedback when things go wrong, focusing on growth rather than punishment.

3. Clarify When to Take Risks & When to Ask for Help – Not every decision needs sign-off. Set clear guidelines on what requires escalation versus what is safe to act on.

4. Reward Initiative – Recognize those who take ownership and make thoughtful decisions, reinforcing that confidence is valued over unchecked caution.

5. Understand Risk Thresholds - Inculcate holistic understanding of what risks can be assumed at each person’s level, and how to lead up when an action may require assumed risk on the leadership’s part. Good leaders will underwrite honest mistakes and risks.

When people feel empowered to operate at their natural best, they don’t just perform better—they thrive. Take a moment to reflect: does your work environment support this kind of confidence? If not, what small change can you make today to move in that direction? And in that, the entire organization rises.

Two Ideas From Me

1. Micro-Moments Shape Macro-Culture. Culture isn’t built through mission statements—it’s built in our everyday interactions, decisions, and responses. The way an organization responds to failure, disagreement, or uncertainty determines whether its culture is one empowerment, or something less.

2. People don’t need to get what they want, they need to feel heard. We all know it’s not always going to go our way. Sometimes things need to change for the organization, for the team. Take a little time to gain insights from the affected persons before moving forward, it might not change anything except their perception, but that’s no small thing. John Ortberg once said that “Leadership is the art of disappointing people at a rate they can stand.”

Three Favorite Things This Week

1. Tool - Loom | Take a step into the wild future where you can communicate with clarity, efficiency, and impact—without the bottleneck of endless meetings or email chains. Leverage asynchronous video, to provide direction, reinforce strategic priorities, and foster a human connection at scale, while giving your teams the flexibility to engage on their own time. | More

2. Podcast - Learning Leader w/ Daniel Coyle – The Secret Of Highly Successful Groups | Ryan and Dan talk the hallmarks of great teams, conditions for excellence, and sustaining excellence for the long game | More

3. Book - The Fearless Organization by Amy Edmondson. | Amy explores how the ability to speak up, take risks, and admit mistakes without fear of retribution is the key to high-performing teams. Fostering trust and open communication, unlocks innovation, engagement, and long-term success in any organization.

A Question for the Week Ahead

If you were new to your company, would you feel safe speaking up on day one? If not, what needs to change? Do you feel empowered to take initiative, or are you navigating caution out of fear?

Have a wonderful week,

I’ll see you Sunday.
​-e