From Building a Law Firm to Advising Founders: What Shawn Stigler Learned About Leadership (E: 002)
Shawn Stigler has spent more than 25 years working alongside founders, executives and investors through some of the most important moments in building and growing companies.
But Shawn hasn't only advised business owners. He's been one.
After starting and growing his own law firm, Shawn eventually joined Michael Best, where he now serves as Managing Partner in Colorado. That combination has given him an unusual perspective: he's experienced the responsibility of building a business himself while also having a front-row seat to hundreds of other founders navigating growth, people, risk and change.
In this episode of the Leadership Capacity Show, I sit down with Shawn to talk about the patterns he's noticed along the way.
We explore what actually builds trust, why reputation matters, the difference between being excellent at your craft and leading people, and what founders often experience as their companies grow beyond the early stages.
We also get into the future of professional work. Shawn shares how AI is already changing the legal profession, what he believes young lawyers should be learning now, and why he sees AI as a leverage tool while human judgment and conversation continue to matter.
In this conversation:
Building a law firm and learning the business behind the profession
What 25 years around founders teaches you about recognizing patterns
Why reputation and trust remain so important
The shift from being great at your craft to leading other people
What leaders are really optimizing for when making decisions
How AI is already changing legal work
Why young professionals should become students of AI
What Shawn is seeing from today's founders and startups
The inflection points that change what a growing business needs from its founder
What Shawn would tell his younger self about taking chances
Leadership Capacity is a conversation series with CEOs, founders and experienced leaders about what leadership has actually required of them—and what they've learned along the way.
New conversations every Tuesday.
#Leadership #FutureOfWork
00:00 — Preview
00:42 — Meet Shawn Stigler
01:55 — Shawn's Path Into Law & Entrepreneurship
05:37 — Building a Law Firm & Learning From Founders
10:12 — What Actually Builds Trust
17:06 — Being Great at Your Craft vs. Leading People
22:46 — How AI Is Changing the Legal Profession
25:34 — Is There Still a Future in Law?
27:37 — What Shawn Is Seeing From Founders Right Now
31:11 — The Patterns Founders Repeat as Companies Grow
34:30 — When Growth Changes the Founder's Job
35:32 — What Shawn Would Tell His Younger Self
Michael Best: https://www.michaelbest.com/people/shawn-stigler/
Shawn Stigler on LinkedIn: https://www.linkedin.com/in/shawnstigler/
Grab the Leadership Book: https://www.hilaniellis.com/hilani-ellis-capacity-the-new-advantage
Subscribe to Leadership Insights: https://www.hilaniellis.com/
Follow along on LinkedIn: https://www.linkedin.com/in/hilaniellis/