In this candid conversation in February 2025 at The Forge, Chip discusses with Nikki the profound impact of having “Sherpas” in his life over the years. Sherpas – those guides, coaches, and mentors who offer us colliding perspectives and elevated sensemaking, model character that’s attractive to us, and who hold us in unconditional positive regard. Through their dialogue, they explore themes of vulnerability, personal growth, and the power of unconditional positive regard.
Below is a transcript from the video
Click here to read more about Sherpas from Nikki.
Nikki: I would love for you to tell me about the value you find in your Sherpas in this season of life right now.
Chip: It’s rare that I feel fully safe. As an Enneagram-type Eight, I’m constantly scanning for threats, always looking for where I have an unguarded flank. When I can be around somebody who just lets me let my guard down and be myself, process whatever I need to, and they’re not going to judge me – they’re going to say, “Okay, that’s where you are” – that allows me to be fully present and grow in ways that I can’t any other way.
Nikki: How would you say your thoughts on that have changed over the years?
Chip: When I was a younger man – and not much younger – I think my arrogance got in the way of seeking help and certainly seeking Sherpas. I knew everything. The things I believed, I believed because I looked at the available data and made a decision. What I didn’t realize was there’s plenty of other data available that I didn’t have access to. I didn’t have all the coaching perspectives, and I didn’t have anybody to help make sense of it.
If you’re in a meaningful Sherpa relationship, you’ve got to let the Sherpa lead. If you’re out in front of your Sherpa trying to climb Everest, it’s not going to go well. You need to be willing to submit to some aspect of this leadership. That doesn’t mean I submit my decision rights to my Sherpas – they’re my decisions, I have to live with the consequences. But when somebody allows me to relax, to consider all the options, it opens up choices for me. Then I can make better decisions where my ego defenses are not corrupting my view of the situation.
Nikki: Why does unconditional positive regard matter so much?
Chip: We are meaning-making machines as humans. We’re constantly trying to think, “What does this mean?” When this person is saying something, what’s really going on? I sense when people have contempt for me, and you sense when people have contempt for you. We all do. If somebody is judging me, my guard starts to go up. I can tolerate judgment, but then I have to fight. I have to be guarded against the judgment, figure out what to push against versus what to let integrate into my way of thinking. That unconditional positive regard just lets me relax to the point where good things can penetrate my heart, penetrate my soul. I can pay attention to it.
One of my Sherpas was Charlie Kelly, who passed away a few months ago from cancer. He just delighted in me, mess and all. He’d say, “Yeah, you’re a mess,” and he could laugh with me about that – he was in on the joke. I knew it was safe to be with him because he had that twinkle in his eye. He might poke at me a little bit and ask a question, but because he was in on the joke, I’d let him do that.
I also have Jackie Halstead, my spiritual director of six years. When I engage with her, she’s not aggressive like I am, not fast-paced like I am – she’s just calm. Through her, I see what better looks like. Dennis Bland is another Sherpa who slows me down. The way he engages interpersonally, I can’t go fast. That forces me to think and reflect. We have a different pace of conversation than I have with any other human being in the world. I don’t always enjoy that pace, but it’s really healthy for me.
What I see in all these Sherpas is that they pay attention to what’s deeply important in life. I can get so distracted by empire-building and things I think are important right now, but they remind me of what’s really important – relationships, the eternal, the metaphysical. They let go so easily of being offended, of attachments to particular outcomes. They seem so open-handed, while I feel like I grip and grasp so tightly in life. It’s beautiful to observe that and think, “Hopefully that’s available to me as I continue to grow.”
Nikki: I’ll just say that I have experienced that open handedness in my relationship with you.
Chip: Well, maybe a little bit. Maybe I’m just kind of like this [gestures slightly open hand] and they’re like this [gestures fully open hand]. But thank you, that’s kind of you to say.
Nikki: Thank you for sharing genuinely with this group, to help us understand what Sherpa means.
Chip: Thanks for asking me. Happy to be here.
The Forge is an informal community of chief executives of sizable organizations, gathering monthly (in-person) to elevate the vision and craft of being a CEO. Here, we do deep inner work, in community.