EP 92: The Hidden Secret to Building Trust in Business with John Hall

What does it really take to stay top of mind with clients, colleagues, and teams—without forcing it, faking it, or burning yourself out? In this week’s episode of Don’t Waste the Chaos, I sit down with John Hall, bestselling author of Top of Mind, Co-Founder of Calendar.com, Chief Strategist at Relevance.com, EY Entrepreneur of the Year, and one of Forbes’ “Top Keynote Speakers to See.”

This conversation is packed with wisdom on trust, influence, leadership, personal growth, and why the way you show up matters more than any strategy deck.

If you’re a founder, leader, or creator who wants to build real trust—not transactional influence—this episode is a must.

What You’ll Learn From John Hall

Entrepreneurship, Ego & Maturity

John shares how starting his first business in college shaped his relationship with pride, perseverance, and learning from failure.
He admits that early success can create false confidence—and how maturing as a leader requires humility, listening, and the willingness to learn from every punch in the gut.

“Entrepreneurship will kick you in the face right when you think you’ve got it figured out.”

The Mindset Shift: Trust Is Personal, Not Corporate

One of the biggest takeaways from John’s book Top of Mind is that trust isn’t a corporate strategy—it’s a personal way of living and leading.

He explains:

  • People want genuine connection, not scripted outreach

  • Trust is built through listening, noticing, and responding

  • The best leaders and brands stay top of mind by adding value consistently

  • Transactional trust-building always backfires

The Power of “Content Triggering”

John introduces the concept of content triggering—the practice of:

  1. Listening carefully

  2. Noticing small moments

  3. Following up with a thoughtful action

Whether it's sending a thoughtful gift, crafting relevant content, or simply remembering someone's needs, these micro-actions build meaningful trust that compounds over time.

“If you genuinely listen for what people value, the right opportunities to serve them appear everywhere.”

Leadership & Time: How John Chooses What’s Worth His Energy

John leads multiple companies, invests in startups, writes weekly columns, keynotes globally, and is deeply committed to family life.

Yet he says choosing what’s worth doing comes down to three things:

1. Strengths Alignment

What is John uniquely good at?

2. Company Priority

What truly moves outcomes forward for the business?

3. Outside Perspective

Who can he trust to check his blind spots?

For leaders who struggle to delegate, John openly shares the ego battle he had to overcome—realizing that just because he could do everything didn’t mean he should.

Why Culture Experiments Fail (and What Really Works)

John is known for fun culture experiments—from extravagant team outings to creative perks. But he’s the first to admit:

  • Fun doesn’t fix culture.

  • Ping-pong tables don’t keep your best people.

  • Perks don’t replace purpose.

What does work?

  • Transparent communication

  • Collaborative work environments

  • Meaningful job assignments

  • Clarity around vision, metrics, and impact

  • Leadership that invests in people, not just outcomes

In his words:

“People want to feel valued and they want to be on a journey with others—not on an island.”

The Nuance of Transparency: When Honesty Helps… and When It Hurts

Transparency is a leadership superpower—but John says it can also backfire if not delivered thoughtfully.

He shares:

  • When transparency builds trust

  • When full honesty can create unnecessary harm

  • How to communicate truth without crossing boundaries

  • The difference between being kind vs. being nice

  • Why intention matters more than technique

And most importantly:
Transparency should never be used as manipulation disguised as honesty.

Burnout, Balance & Protecting Your Mental Health

Despite his success, John openly discusses a season of intense burnout last year—even in the middle of major business wins.

He breaks down:

  • How health issues triggered mental exhaustion

  • Why your environment and support system matter

  • The power of surrounding yourself with people you enjoy working with

  • How community protects leaders from burnout

  • What personal fulfillment has to do with professional resilience

He also affirms what many leaders feel but don’t admit:
Success doesn’t erase insecurity. Growth requires constant self-awareness.

Chaos That Became a Gift

When I asked John what chaos ultimately turned into unexpected good, he shared stories from exiting his previous company—navigating identity loss, rebuilding from scratch, and the challenge of re-grounding after success.

That season of chaos eventually led to:

  • New business opportunities

  • A stronger team

  • Deepened self-awareness

  • A healthier leadership mindset

“You’re being challenged for a reason. If you stay the course, the chaos becomes part of what equips you.”

Resources Mentioned

Work With Kerri

If you’re ready to build trust, clarity, and culture inside your organization:

HR in a Box

Monthly training, tools, and templates designed for small business leaders.

Speaking, Fractional HR, or Consulting

Bring me in to strengthen your culture, align your leadership team, or support your HR systems.

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EP 93: Reinvention, Accountability & the Life You’re Not Done Living — with Matt Vincent

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EP 91: Tough Year at Work? Rebuild Trust with This 3-Part Leadership Framework