To mark our business law firm’s 20th anniversary, I’m sharing a weekly articles highlighting lessons learned over the past two decades. By transparently reflecting on our journey embracing change and innovation, I hope to provide perspective applicable beyond the legal industry.  Thanks, Scott Levine.

When we started our law firm 20 years ago, we were armed with daring ideas but little experience to back them up. We were legal daredevils, willing to embrace audacious strategies and push boundaries in ways few small firms would dare. That bold ethos shaped our DNA and drove our exhilarating journey to growth and success.
I still remember the feeling of showing up to pitch our first major client, a Fortune 500 company, while we were still operating out of a tiny office space. We pulled an all-nighter preparing a slick PowerPoint presentation that masked our inexperience. But we had confidence and a vision to transform legal services that no old-school firm could match. They took a chance on us, and we faked it till we made it, learning as we went and ultimately delivering outstanding results.
Early wins like this fueled our appetite for thinking big despite our modest size. We constantly asked “Why not us?” as we pursued clients our more seasoned competitors deemed out of reach. Our commitment to pushing boundaries delivered innovative solutions no boilerplate legal shop could fathom.
One of our first daring gambits was taking on an industry giant by offering similar services at prices small businesses could afford. Lacking their resources, we worked tirelessly to prove our unique model could disrupt that segment. Within a few scrappy years we utterly transformed legal access for smaller companies in our region.
While other firms focused on narrow specialties, we forced ourselves into uncharted legal territory, expanding capabilities few would have believed possible. The thrill of leaping into the unknown kept our team inspired to defy expectations.
We knew the only way to maintain this pace was to hire audacious legal ninjas rather than risk-averse paper-pushers. Our team of misfit attorneys from diverse backgrounds became secret weapons for conjuring unconventional strategies. As one tech exec told us, “You guys don’t think or work like any lawyers I know. You actually get what I’m building here and deliver solutions tailored specifically to my startup.”
After 20 years of fearlessly bucking tradition and betting on ourselves, we’ve broken into elite ranks of clients and prestige once seen as unrealistic for our small crew. But despite our growth into a national firm, we still carry that scrappy, entrepreneurial heart.
I recall one of our first clients, a promising startup, that epitomized our fly-by-night approach. We related to their hunger despite limited resources and experience. Having just stretched ourselves to afford a cramped office, we saw kindred spirits in these legal longshots. They couldn’t afford top shelf representation, so we took a chance on each other.
Within a few years, we had steered them from fledgling dreamers to industry titans. They took off like wildfire, but because we bet on them early, their meteoric rise pulled us up with them. We graduated from that broom closet to posh corner offices, but never lost touch with our gritty roots.
In our first decade, amidst the breakneck pace, we occasionally splurged on whims like launching a side marketing firm that predictably flamed out. But balancing daring ideas with business fundamentals was part of the learning curve. Despite some spectacular fails, we racked up enough wins to stay comfortably reckless in our approach.
Eventually we realized just being expert lawyers wasn’t enough; we had to get strategic about how we structured and ran our firm too. Bringing on a CEO and separating ownership and management allowed me as Founder to focus purely on disruptive strategy. With daily operations in steady hands, I was unleashed to pilot even bolder innovations that exponentially grew our capabilities.
Fast forward 20 years, and our firm has become a major player on the national business law scene while retaining our spunky identity. With outposts now in Chicago, Southern Illinois, Denver and Tampa Bay, we punch way above our weight serving clients most firms our size cannot.
But expansion wasn’t just about geography. Finding the right partners led us into wholly new legal fields beyond our initial scope. Merging practices gave us capacity to take on more daring challenges. And becoming early adopters of legal software supercharged our productivity.
Staying true to our values, we’ve fostered an environment where legal mavericks thrive. Our attorneys are given autonomy to take smart risks that shake up stale industry norms. Individual rewards are tied directly to the firm’s overall success so everyone is invested in lifting the collective. Staff stick around for years because they actually enjoy our dynamic, fast-paced culture. Who knew law could be such an adventure?
Sure, our shoot first approach still misfires or drives us into a ditch on occasion. But as long as the wins outpace the fails, we’ll keep pushing limits few firms dare to cross. Could we play it safer? Absolutely. Yet 20 years since hanging up that first shingle, we’re still blazing our own trail – and that wild ride just keeps getting more fun.

After over 20 years of managing a business law firm, I’ve come to think of my job as akin to herding cats. Attorneys have strong, independent personalities that don’t always mesh well. However, I’ve learned these traits can actually be channeled in productive ways if handled properly. I’ll share two stories that illustrate this.

Several years ago, I interviewed an attorney who, on paper, seemed perfect for our firm. However, his references, whom I knew personally, warned he would be toxic and incompatible with our culture. I was enamored by his dazzling resume though and hired him against their advice.

Initially, he charmed clients with his experience. But over time, troubling behaviors emerged. He kept staff late “on call” in case he needed support, sending them on personal errands like food and coffee runs instead of letting them go home.

As a manager, I waited too long to take action. His behaviors hurt our culture and my reputation as a leader. Eventually he left, but the damage was done. I learned the hard way that no matter how skilled, someone at odds with organizational values will sow dysfunction.

More recently, another incident provided contrast. An “old school” senior attorney long seen as imperious began mistreating support staff. Believing junior roles existed to serve attorney needs, her temper and yelling had apparently gone unchecked for some time.

The truth emerged shocking brutality when she dressed down a staff member over email for a minor issue. When I found out, I immediately called a meeting between her, the staff member and our senior administrator. I made clear such abusive behaviors would not be tolerated, no matter her seniority.  And that she couldn’t continue to work for us unless her behavior changed.  She walked.

The staff member seemed stunned that I would confront this powerful attorney so directly over staff mistreatment.  But it reverberated for years that we prioritize the experience of all employees, no matter where they fall on the org chart. Sometimes “herding cats” means protecting kittens from nasty tabbies run amok.

These two stories illustrate sharply divergent approaches to managing strong personalities. In one, I let damaging behaviors fester, eroding team cohesion while in the other, I confronted the issue directly.

I learned that leadership means making judgments informed by principles, not credentialed resumes. And “herding cats” requires establishing mutual understanding – including what crosses the line. Clear cultural priorities allow managing even the most willful attorneys by appealing to our shared professional values of respect and integrity.

Sure, attorneys cultivate strong independent streaks and opinions. But every orchestra needs both string sections and percussion. As conductor, my aim is not whipping distinct talents into uniformity, but providing enough structure so distinct melodies harmonize.

With that insight, I embraced the improvisational spirit of jazz over rigid orchestral forms in managing our legal stable. Does this permit controlled chaos at times? Absolutely. But the right framework channels individual strengths into a symphony rather than cacophony.

There have been plenty of learning moments over the years – like the two stories shared above. At times I waited too long to address problematic behaviors that then became harder to correct. At others, decisive action reinforced cultural pillars that prevented erosion of mutual trust and respect.

Herding talented thoroughbreds is never easy – they still need room to run free and fast. But apply the right care and guidance, they can win races together rather than trip each other up on the track. So while attorneys may seem like intractable cats at times, I’ve learned great rewards come from embracing each one’s “distinctive meow”.

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