Hunger & Heart with Kaila Colbin
Jul 7, 2026 · 57 min · 12 segments
Nobody is born good at hard conversations. Not even the people who teach them. I’ve spent years running Brené Brown’s Dare to Lead™ programme. I built the Courageous Communication™ programme…
Kaila ColbinHost
Hannah HudsonGuest
I want to start with a little story, which is a few months ago, I was having a conversation with one of my advisors, and I was feeling very... salty and grumpy, that the whole world had not bent itself to my will and that things seemed difficult and that all of the doors hadn't kind of magically opened before me.

And I was particularly feeling hard done by because I was telling myself a story that I was not allowed to have a hard time because I'm the dare to lead person and that therefore I have to always show up gracious and open and appropriately vulnerable and clear and kind and, you know, not grumpy or resentful or anything.

And so I said to my advisor, I was like, you know, why do I have to always be so good at this? Can't I just throw myself on the ground and bang my fist and kick my feet and throw a tantrum? And she goes, you absolutely can.

And it was such a moment for me of this realization that I don't have to do anything.

No one's forcing me to try to be this kind of leader that sometimes I'm okay at and sometimes I stumble at.

that I choose to try to do this because I think it is a better way to lead and that sometimes that is hard.

I think, oh, this is such a great place to start because I think with difficult conversations, it's so like, it can get kind of, especially when you're talking about teaching it rather than the realities of implementing it.

I think there's so many times that people are like, and it's all rainbows and unicorns and look how amazing it is.

And like the reality is that, often it sucks like it sucks to have to have that like moment of courage where you're like yes I am going to do this and I'm going to say the hard thing and it like I think the end result builds more of the type of world that we want to have.

And making that choice that you're like, this is hard and I'm going to do it anyway, is such a big part of this journey.

like it's it's not the like zen um like happy hippie like um uh domain that i think that it could be easy to um kind of sometimes box this um type of work into

And one of the things that I hear sometimes is people kind of saying they want to have an organizational culture that is high trust, where everyone's willing to talk about hard things.

And what we know, what I know, lived experience every single day is that that is the culture that requires the discipline and the commitment and the willingness to be uncomfortable.

I want to start with a little story, which is a few months ago, I was having a conversation with one of my advisors, and I was feeling very... salty and grumpy, that the whole world had not bent itself to my will and that things seemed difficult and that all of the doors hadn't kind of magically opened before me.

And I was particularly feeling hard done by because I was telling myself a story that I was not allowed to have a hard time because I'm the dare to lead person and that therefore I have to always show up gracious and open and appropriately vulnerable and clear and kind and, you know, not grumpy or resentful or anything.

And so I said to my advisor, I was like, you know, why do I have to always be so good at this? Can't I just throw myself on the ground and bang my fist and kick my feet and throw a tantrum? And she goes, you absolutely can.

And it was such a moment for me of this realization that I don't have to do anything.

No one's forcing me to try to be this kind of leader that sometimes I'm okay at and sometimes I stumble at.

that I choose to try to do this because I think it is a better way to lead and that sometimes that is hard.

I think, oh, this is such a great place to start because I think with difficult conversations, it's so like, it can get kind of, especially when you're talking about teaching it rather than the realities of implementing it.

I think there's so many times that people are like, and it's all rainbows and unicorns and look how amazing it is.

And like the reality is that, often it sucks like it sucks to have to have that like moment of courage where you're like yes I am going to do this and I'm going to say the hard thing and it like I think the end result builds more of the type of world that we want to have.

And making that choice that you're like, this is hard and I'm going to do it anyway, is such a big part of this journey.

like it's it's not the like zen um like happy hippie like um uh domain that i think that it could be easy to um kind of sometimes box this um type of work into

And one of the things that I hear sometimes is people kind of saying they want to have an organizational culture that is high trust, where everyone's willing to talk about hard things.

And what we know, what I know, lived experience every single day is that that is the culture that requires the discipline and the commitment and the willingness to be uncomfortable.
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