🚲 What Riding Bikes Taught Me About Leadership 🚲

This past week was my little sister’s birthday, and as I was looking through old photos, I found one that really made me pause. It’s a picture of us as kids, riding our bikes. I’m in front, glancing back over my shoulder, and she’s behind me, looking up and following my lead.

That simple image spoke volumes about leadership. It’s not about barreling ahead, assuming others will catch up. It’s about staying aware of who’s riding alongside you and behind you, making sure they’re supported on the journey. As lawyers and legal professionals, we’re often in motion,  but let’s not forget to check in with our teams and colleagues along the way.

Here are five reflections, with practical ways to apply them in your leadership every day:

1. Look Back to Lead Forward

Good leadership requires situational awareness - not just of goals and deadlines, but of people. Taking the time to "look back" helps us notice who might need a little extra support, who’s excelling, and who might be falling behind silently. Regular check-ins aren’t just a nicety; they’re essential for keeping your team engaged and aligned.

Try this:

• Schedule short, regular one-on-ones that are focused on well-being and growth, not just work progress.
  

• Use simple check-in questions: What’s one thing you’re excited about? What’s one thing you’re finding challenging?
  

• Watch for non-verbal cues of stress or disengagement in meetings and conversations.
  

• Create space for open feedback, and genuinely invite it (and don’t forget to act on it as well!).

2. Pace Matters

Everyone moves at their own speed, especially in high-performance environments like law. As leaders, we need to be sensitive to where people are in their development and balance the urgency of the work with the reality of human capacity. Adjusting your pace (where you can) shows care and helps prevent burnout.

Try this:

• Match project assignments to team members' experience levels to build confidence gradually.
  

• When things are moving fast, offer extra clarity: lay out priorities and avoid overwhelm.
  

• Model healthy pacing yourself by setting boundaries and respecting downtime.
  

• Recognize that new team members may need more time to get up to speed and normalize the learning curve.

3. Encourage Along the Way

A well-timed word of encouragement can be the fuel someone needs to keep going. People thrive when they feel seen and appreciated, especially in demanding environments. Celebrating small wins fosters momentum and keeps morale high.

Try this:

• Send quick notes or messages of appreciation when you notice effort, not just results.
  

• Celebrate milestones publicly - big or small - in team meetings or emails.
  

• Acknowledge growth: “I’ve noticed how much you’ve developed in this area — keep going!”
  

• Encourage peer-to-peer recognition to build a culture of shared support.

4. Lead with Empathy and Presence

Leadership is relational. Being present and empathetic builds trust and psychological safety, allowing your team to perform at their best. Especially in fast-paced legal environments, it’s easy to get task-focused and miss emotional undercurrents - stay connected!

Try this:

• Start meetings with a quick personal check-in before diving into the agenda.
  

• When someone shares a challenge, listen fully before jumping to solutions.
  

• Share your own experiences vulnerably to model openness.
  

• Recognize external pressures (personal or professional) and offer flexibility when possible.

5. Enjoy the Ride Together

Our legal work is serious, but it doesn’t always have to be solemn. Creating moments of connection and levity strengthens relationships and sustains teams over the long haul. Leadership is more rewarding when we enjoy the journey with the people around us.

Try this:

• Build moments of fun into your team culture, like casual virtual coffee chats or in-person lunches.
  

• Celebrate birthdays, milestones, and even just making it through a tough week together.
  

• Share moments of gratitude regularly - what you appreciate about your team or colleagues.
  

• Remember to pause and acknowledge progress as a group, not just individually.

  
  

As I reflect on that photo of my sister and me, I’m reminded that leadership isn’t just about where you’re going; it’s about who you’re traveling with and how you make them feel along the way.

Happy Birthday, Sis! I’m so proud to be your big sister — and grateful for all the ways you’ve inspired me to be a better leader in life and work. ❤️🚲

Recommended Recourses

[Article] “The Best Leaders are Great Teachers” by Sydney Finkelstein | Harvard Business Review

[Article] How Self-Reflection Makes You A Better Leader by Lyssa DeHart | Forbes

[Article] The Importance of Employee Recognition: Low Cost, High Impact | Gallup

[Video] Everyday leadership by Drew Dudley | TED-Toronto

[Video] Lead like the great conductors by Italy Talgam | TedTalk (I loved this one as it connects being a conductor of an orchestra with being a great leader - I know there are many musicians in our EsqurieWell community, but this is applicable to everyone!)

Feel free to download, share, and use these quotes to inspire yourself and others!