Why Great Leaders and Great Entrepreneurs Excel at One-on-One Conversations
One-on-one conversations are often seen as the backbone of strong leadership, but what’s rarely acknowledged is how foundational they also are to entrepreneurship. Whether you’re leading a team within a corporation or scaling your own startup, how you show up in your 1:1s reveals everything about the kind of leader—or entrepreneur—you are becoming.
At first glance, managers and founders might seem worlds apart. One is navigating internal politics and team dynamics; the other is wearing ten hats, pitching investors in the morning and solving customer issues by night. But both roles require an almost identical mindset when it comes to people: presence, empathy, and intention.
Yet, too many leaders—whether corporate or entrepreneurial—miss the mark.
The Problem with Most 1:1s
Most managers want to have impactful 1:1s. But few have been taught how. Somewhere along the line, the true purpose of these meetings got lost. What should be a moment of connection and coaching becomes something else entirely:
- A rushed, back-to-back calendar filler
- A reactive firefighting session
- A glorified task update
- The first meeting to get canceled in a busy week
When this happens, something crucial is lost. Because 1:1s, at their core, are not about the work. They’re about the person doing the work.
What Great 1:1s Actually Do
Whether you’re a startup founder with a lean team or a corporate manager with a dozen direct reports, meaningful 1:1s are your best chance to:
- Build trust through consistency and active listening
- Uncover issues before they snowball
- Coach your team for performance, not just productivity
- Align goals while humanizing the hustle
- Retain talent through empathy and growth conversations
Leadership and entrepreneurship intersect here: both require emotional intelligence, the discipline to be present, and the humility to learn from those you lead.
The Entrepreneur’s Edge: Why Founders Must Master the 1:1
Entrepreneurs don’t have the luxury of hierarchy or departmental buffers. Every conversation matters. When you’re building something from scratch, the emotional climate of your team (or your co-founder, or your first hire) is everything. And in the whirlwind of early growth, your 1:1s might be the only real chance you get to check in—not just on progress, but on wellbeing, motivation, and alignment.
At ItsHerWay, we’ve seen this firsthand in our journey with thousands of women-led businesses across the region. The most successful founders aren’t just good at what they do—they’re great listeners, confident communicators, and emotionally available leaders.
Building Better 1:1s: How ItsHerWay Helps
Through our community, we’ve trained, mentored, and championed the kind of entrepreneurial leadership that starts with connection. Our workshops and coaching programs are specifically designed to instill the core skills that drive great 1:1s:
- Active Listening techniques for empathetic conversations
- Coaching for Growth frameworks to guide performance discussions
- Conversation Models that help shift from status to strategy
- Confidence-Building Exercises to own your leadership presence
From our Leadership Circles to our Founders Bootcamps, we embed the mindset that one-on-ones are not optional—they are mission critical.
Because whether you’re managing a team or building a company, how you lead your conversations is how you lead, period.
Final Thought: Conversations as Culture
In both leadership and entrepreneurship, culture isn’t built in town halls or vision decks. It’s built in conversations. It’s what happens in the quiet 30-minute check-ins when no one’s watching.
Make them count.
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Want to learn more about ItsHerWay’s programs for leadership development and entrepreneurial coaching? Join our community or connect with us to explore how you can grow into the leader you were meant to be.