Reboot Podcast Episode Wisdom for Work #23 – Cultivating Conditions of Courage

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.


Ali Schultz

Ali Schultz

Co-founder of Reboot & Coach

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Virginia Bauman

Virginia Bauman

Coach & Facilitator

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Episode Description

How can leaders create a safe space for honest conversations, even when those truths challenge the status quo? In this episode of Wisdom for Work, Reboot Coaches Ali Schultz and Virginia Bauman unpack the concept of “conditions of courage,” exploring how fostering psychological safety within teams goes hand-in-hand with individual leaders cultivating self-awareness about the conditions that empower them to be honest. 

Through personal stories and insightful discussion, they unpack the power of setting boundaries and how embracing courage and authenticity in the workplace generates healthier relationships and boosts productivity. This episode is essential listening for anyone who wants to build stronger relationships, speak their truth, and navigate challenging conversations in the workplace.

Show Highlights

Memorable Quotes:

“What does the individual need to do to feel safe enough to say something that might upset the other leaders in the company? Because we each have that personal component of this work that plays into the organizational dynamic and pattern.” – Virginia Bauman

“If you were a founder or a CEO and you found out that an individual or several top individuals were interviewing, how would you feel? Would you worry about it? Would you have a conversation? Would it challenge the relationship’s trust?” – Virginia Bauman

“When you have the conditions of courage, it’s actually paradoxically less controlling. When you are saying this is what I need to stay here, and you’re saying what your real terms are, what your authentic needs are, that’s less controlling than when you are silent and needing them to shift for you and focusing on where the deficiencies are.” – Virginia Bauman

“We have to believe that a conversation is going to be able to be held with deep awareness and good faith for this to work. The magic of this condition, of course, is that it benefits you regardless of whether or not there’s a healthy pattern or there’s a challenging, unhealthy pattern happening. Your plan B is important regardless.” – Virginia Bauman

“Once you take on that CEO role, getting out of the CEO role is non-trivial. It’s a big role you have a lot to do, but this agenda plays out with CEOs all the time. If you don’t know what your plan B is, you also won’t be showing up to the board knowing what you need. You won’t be showing up to your executive team, knowing what you need in order to be most effective. And so paradoxically, you know, the CEO role also needs to be, it needs to be plan A, but we need to know what plan B is too.” – Virginia Bauman 

“We each have a huge role in knowing how we can create our own conditions of courage and then taking the steps that we need to take so that they’re intact and we feel safe to have very conflictual conversations with the leaders that we depend on to build value in the org.” – Virginia Bauma