Escaping the Vanilla Middle in Legal Conversations

Escaping the Vanilla Middle in Legal Conversations

We have a problem I call the "Vanilla Middle".

As lawyers, we prize humility and discretion. So when a successful lawyer is asked about their work, they don't talk about what was hard for them and don't talk openly about what they did effectively.

So we get the Vanilla Middle. We ask questions like "can you talk about the importance of mentorship?" or "what advice do you have for younger lawyers?".

These are softball questions that get rehearsed answers. They're truthful, but they aren't the truth.

Vanilla Middle

The Vanilla Middle is fine if you need an uncontroversial introduction to an audience. But if you're looking for depth, the opportunity lies in the bookends.

The real opportunity lies in two key areas:

  • talking about actual challenges successful lawyers faced, then and now
  • and talking about how they made the right call for the right reasons

Real Stories

My podcast sits in those ends. You'll hear from a practice leader about how she bombed an an early deposition, took it as a call to action, and eventually became known for her deposition expertise. Or from a first-chair litigator about how she was underestimated as an associate.

But you'll also hear from a young partner who re-read a Supreme Court decision 100 times to extract overlooked insights against consensus. Or how an experienced first-chair trial and appellate litigator got his first Federal Circuit argument by finding a pro se patentee whose application raised an unresolved issue of law.

Enduring Truths

So when we sit down with successful lawyers and learn how they make decisions and what principles they use, we learn enduring truths we can apply.

We find tension points: should we diversify or focus? Should we be strategic or opportunistic?

And we connect with the real people who went through these experiences. Exceptional lawyers are simply talented people who applied an effective system we can learn.

Final Thoughts

We don't have to settle for the Vanilla Middle any more. The true insights into legal careers emerge when we move beyond softball questions and delve into actual challenges and effective decisions. This path leads to enduring truths and allows us to connect with the real people behind exceptional legal careers.

Exceptional lawyers aren't just talented; they've applied effective systems we can all learn from. The opportunity for genuine understanding lies in exploring their tension points and decision-making principles.

Whether it's a conference panel, a fireside chat, or an interview, you can choose depth.