Coaching for Courageous Cultures
By Ali Lalieu
March 2025
Over the past five years, I’ve had the privilege of taking almost 1000 people through the Brené Brown Dare to Lead ™ curriculum.
One of the questions I am often asked is “how can our leaders use a coaching approach to bring to life the frameworks taught in Dare to Lead?”
This is such a great question, because for all new learning to become ‘sticky’ we need to practice new concepts, learn from what works and what doesn’t work, and try again – all spaced over time (so our brain can form new neural pathways ~ new ways of thinking and responding).
I’d like to share a cheat sheet of Coaching Questions that might be useful for your leaders (used in context, in no specific order, and with genuine curiosity):
What was your biggest takeaway from the Dare to Lead course?
How has your learning influenced your leadership style?
What has changed the most about your leadership since completing Dare to Lead?
Where do you still feel resistance when it comes to leading with vulnerability?
What fears have surfaced as you’ve implemented this work?
How are you navigating them?
How do you hold yourself accountable for practicing courageous leadership daily?
Where do you still struggle with vulnerability in your leadership, and what steps are you taking to lean into it?
What’s the biggest challenge you’re facing now as leader?
What feedback are you getting that’s challenged you the most? How did you respond?
Where are you avoiding difficult conversations?
What’s the hardest piece of feedback you’ve had to give? How did you prepare for this conversation?
How do you check in with yourself before having a difficult conversation to ensure you’re leading with courage and empathy?
How are you helping your team develop the skills to engage in productive, courageous conversations?
How did you communicate in a ‘Clear and Kind’ way?
How comfortable are you with the vulnerability (risk, uncertainty, emotional exposure) right now?
What fears or self-doubts are coming up for you?
How can you role model leadership vulnerability without losing authority?
What are your top 2 personal values?
How can you anchor into them during this time?
What patterns are you noticing in how you become self-defensive in conversations (armor)?
What patterns of resistance are emerging?
How are you engaging with them courageously?
What recent example are you willing to share where you had to make a tough decision that aligned with your values?
How can you build and sustain trust across teams right now?
How are you handling setbacks and failures?
What specific practices help you recognize and manage shame triggers in your leadership?
How do you build resilience in yourself and your team when facing setbacks or failures?
What’s your resilience strategy?
What are your personal strategies for recognizing and managing shame triggers in leadership?
How do you help your team bounce back from failure in a way that fosters learning rather than blame?
What support do you feel you need to navigate this challenge?
How have you built trust in your team since implementing Dare to Lead principles?
What signals do you look for to assess whether psychological safety is strong or needs improvement?
How do you respond when you notice fear or defensiveness creeping into your team culture?
What behaviours do you now recognize as armored leadership, and how are you working to shift away from them?
What’s one courageous action you will take this week?
How will you hold yourself accountable?
How are you holding others accountable?
How are you actively encouraging your teams to challenge your thinking and to speak up?
What’s a NO you need to say to create space for a bigger YES?
What personal boundaries do you need to set to avoid feeling consumed by competing demands?
Of all the 7 elements in the BRAVING Trust model (Boundaries, Reliability, Accountability, Vault, Integrity, Non-judgement, Generosity), which would you identify as your strengths and which as your growth areas?
How are you role modelling self- care for your team?
A year from now, how will you know you’ve answered your ‘Call to Courage’?
Not every moment is a Coaching moment.
Train your leaders to have the intuitive sense that the conversation they’re having with a direct report/peer/boss is an opportunity to courageously connect that person to their potential.
Brené Brown’s definition of Leader is “anyone in the organisation who sees potential in themselves and others, and has the COURAGE to connect them to that potential”.
As curiosity is THE skillset of the future, this so often calls for a Coaching Approach.
Cheers Ali xo