At some point, all of us will run into the edge of our competency; where we don’t know answers to questions, we’re tangled in problems we’re unsure how to resolve, and we’ve taken on more than we can handle with our current skills and resources. We hit that point where what got us this far isn’t what will get us through the changed context. It’s not a problem that this happens, it’s what we do next that matters. Will we grow through this this? Or stay stuck and stagnate?
To keep expanding the edges of our competency and our capacity to perform well in changing contexts, we need to keep acquiring and experimenting with new skills, language, perspectives and courage. Change is the only constant. Corny, but true.
Here are some coaching questions to put in your leadership toolkit, using Brené Brown’s Dare to Lead™ four skillsets of courage. You can use these with team members who might be struggling in a new role, have stumbled into a roadblock, or could do with some self-reflection. These are also excellent prompts for yourself as you continue expanding your daring leadership practice.
Rumbling with Vulnerability (Embracing discomfort and leaning into tough conversations)
- What fears or uncertainties are showing up for you in this role?
- How are you feeling about your performance, and what story are you telling yourself about it? What data informs your story? Where are there gaps?
- Where are you avoiding asking for help or admitting struggle?
- If you operated from courage, how would you approach this challenge differently?
Living into Your Values (Aligning actions with core values to navigate challenges with integrity)
- What personal values do you want to lean into as you navigate this challenge?
- How do your values guide your decisions and leadership in this role?
- Where do you feel a gap between your values and your current performance?
- How can you show up in a way that’s both brave and authentic, even when things are hard?
BRAVING Trust (Building trust with yourself and others to create a foundation for growth)
- What do you need to be reliable and hold yourself accountable in this moment?
- Who in your square squad or empathy seats can you turn to for honest feedback and support?
- What do you need to help you live into your integrity?
- Are you judging yourself for being stuck? How might generosity, positive intent and self-compassion help you expand to where you’d like to be?
Learning to Rise (Building resilience and getting back up after setbacks)
- What’s one setback you’ve experienced so far, and what did it teach you?
- How do you typically respond to failure or struggle? What’s been your most successful strategy?
- What small, courageous step can you take today to move forward?
- What would it look like to turn this challenge into an opportunity for growth, learning and/or experimentation?
Owning Your Story & Choosing Courage Over Comfort (Reframing the narrative and stepping into brave leadership)
- What’s the hardest part of this transition, and what do you need to say out loud to move through it?
- If you were writing the next chapter of your leadership story, what would you want it to say?
- What’s one brave conversation you need to have with yourself or someone else?
- If you fully embraced courage right now, what’s the first action you’d take?
As essayist Anaïs Nin once observed: “Life shrinks or expands in proportion to one’s courage.” Choose courage. Keep expanding!





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