Building leadership confidence through diverse perspectives and curiosity

Executive overview

Moving from operational expertise to executive leadership creates a confidence crisis: the metrics that defined success disappear. The work shifts from doing to enabling, and leaders lose the tangible evidence that they're adding value.

Diverse peer communities — across industries and backgrounds — normalize this struggle and break the assumptions that narrow expertise builds. Structured curiosity practices replace the habit of jumping to answers.

The core insight: leadership confidence grows not from having answers, but from asking better questions across diverse perspectives.

The operational-to-executive transition

• Operational excellence creates a false baseline — daily patient counts or completed tasks feel like proof of impact
• Executive roles remove that tangible feedback, creating "unrest in the soul": am I enough, am I doing enough
• The shift is genuinely a different job, not just a bigger version of the same one
• Seeking peers who feel the same thing is a legitimate strategy, not a sign of weakness
• New executives commonly assume everyone else has it figured out — they don't

Introversion as an executive

• One-on-one interactions surface more information and build deeper understanding than large-group formats
• Introverts in executive roles must still be visible — physically present, on camera, network-building
• "Meeting before the meeting": engaging board members or peers individually before large forums gets better input and reduces in-room anxiety
• Asking a trusted peer "what do you think I'll bring to this meeting?" validates strengths rather than fishing for praise
• The goal is balance: play to one-on-one strengths while deliberately building large-group presence

The value of cross-industry peer cohorts

• Industry-specific groups default to talking shop; cross-industry groups are forced to discuss people and leadership
• Hearing from leaders running world games, owning businesses, working outside the US, or building consulting practices breaks industry-specific assumptions
• All groups converge on the same core: wanting to make an impact, improve communities, grow as leaders
• The wave pattern: surface-level diversity → normalise shared goals → learn from different assumptions → broaden perspective
• Relationships persist years after the cohort because the learning is personal, not transactional

Practicing curiosity

• Default behaviour for operationally expert leaders: pattern-match quickly and jump to solutions
• The silence after a question feels painful — that discomfort is the practice
• Daily commitment: ask one more question before offering a solution
• Key phrase: "Help me understand what that looks like for you" — even when you think you already know
• In group settings, explicitly invite the dissenting voice: "That's a different perspective — tell us more about why you feel that way"
• Surfacing one dissenting view can change the entire decision in the room
• Watching direct reports adopt the same behaviour is the clearest signal the habit is working

Building confidence with senior stakeholders

• Pre-meeting conversations with peers shift the question from "do I belong?" to "what does this audience need?"
• Walking in and simply being present — knowing you belong — is itself a skill that requires practice
• Fear before high-stakes interactions is a signal of caring, not incompetence; it stops being paralyzing with repetition
• Post-meeting debrief: identify two or three things learned; pair with gratitude
• Use objective evidence from each meeting to counter the stories the mind manufactures before the next one

Connecting diverse communities as a leadership strength

• Health equity work requires convening people who would never naturally be in the same room
• Connector leadership: identifying people with complementary talents across industries, geographies, and demographics
• Early discomfort in cross-sector groups mirrors the cohort experience — it gives way to better problem-solving
• Saying out loud what needs to be said about disparities, then asking "what do you think and who do we get together?" — that courage is what moves the needle
• Modelling willingness to try and fail visibly makes you a more credible leader than projecting certainty

On changing your mind

• Expert-domain thinking is a trap: it makes leaders solve non-domain problems with domain-specific mental models
• The lesson relearns itself repeatedly — stepping back to think as a leader (not as a nurse, engineer, or operator) unlocks solutions
• "Lessons earned" rather than lessons learned: the discomfort of growth is the price of the lesson
• Translatable problem-solving skills cross all dimensions once you stop filtering everything through professional identity