What Makes a Testifying Expert Witness Credible in Complex Litigation?
With guest Joseph Tedeschi, Eleven Canterbury Consultant, and Former General Counsel at Citi, and moderator Dan Martin, Eleven Canterbury Program & Relationship Manager
Summary
What does life after a high-level corporate legal career really look like?
In this episode of Chapter Two: Creating New Beginnings, Joseph Tedeschi, former General Counsel for multiple divisions of Citi, shares how he built a second chapter that combines expert witness work, nonprofit leadership, teaching, and the arts.
Joseph discusses the transition from serving as in-house counsel at one of the world’s largest financial institutions to serving as an expert witness in complex litigation matters. He explains the difference between advocating for an organization as general counsel and providing focused, independent analysis as an expert witness, where every opinion, explanation, and assumption may be challenged by lawyers, economists, regulators, and courts.
The conversation offers a rare inside look at how expert witnesses contribute to litigation involving mergers and acquisitions, contracts, financial markets, and corporate transactions. Joseph also explains why expert witness work requires experienced executives to return to first principles and to communicate highly technical concepts in ways that judges, tribunals, and non-specialists can clearly understand.
But this episode is about more than law and litigation.
Joseph also shares how his second chapter created room for longtime personal passions, including nonprofit leadership, teaching, and the arts. As Chairman of a nonprofit dance company and a leader with Volunteer Lawyers for the Arts in New York, he reflects on building a portfolio career that blends intellectual challenge with personal meaning.
Topics discussed in this episode include:
• Transitioning from General Counsel to expert witness work
• How law firms select expert witnesses
• The difference between advocacy and expert analysis
• M&A and corporate transaction expertise in litigation
• Explaining complex financial and legal issues in court
• Portfolio careers after executive leadership
• Nonprofit leadership and second chapter careers
• Balancing professional achievement with creative purpose
For executives considering consulting, board service, expert witness opportunities, or a broader career transition after corporate leadership, this conversation offers an honest and thoughtful look at what comes next.
Joseph Tedeschi is one of more than 3,000 senior leaders in the Eleven Canterbury network serving organizations worldwide as expert witnesses, interim executives, board advisors, and strategic consultants.
About the Series
Chapter Two: Creating New Beginnings explores how accomplished executive leaders reinvent themselves after traditional corporate careers. Through candid conversations, the series examines career transitions, portfolio careers, leadership, purpose, and the realities of building a meaningful next chapter.
Transcript
Dan Martin: My guest today is Joseph Tedeschi. We’re going to talk about his second chapter, following a really successful career as general counsel for various parts of Citi. Now he’s morphed into an expert witness with Eleven Canterbury, and he’s the Board Chairman for a dance company.
When people start their second chapters, sometimes they go into things that are kind of related to what they did. You would guess that being a general counsel and being an expert witness are somewhat related. How did you get into expert witness, and do you like it? How does it differ from your experiences?
Joseph Tedeschi: Great question. Thanks for having me, Dan, and thanks for the question.
Actually, I got into being an expert witness when one of my former colleagues at Citi, who is also an expert witness, she has an expertise in compliance, not law, reached out to me after I had left Citi and said, I think you’d be really ideal for this kind of work and role.
From her experience as an external witness, I guess she believed I had whatever skills were necessary for this. So, she introduced me to Eleven Canterbury. I’ve been part of the team here for a couple of years, so it was really an introduction through a colleague who was also moving into, as you referred to it, Dan, the second stage of her own career after a very successful and senior career in compliance at Citigroup.
Dan Martin: How does it differ? It seems that when you’re a general counsel, you’re representing the position of the organization you’re working for. When you’re an expert witness, you’re a bit more unbiased.
Joseph Tedeschi: It’s a great question. I think what I would do is lean a little bit on those words.
First of all, as a general counsel, I have always taken that relatively seriously. You have to have a lot of general areas of expertise. And you have to provide counsel. It’s that simple. But you are allowed to be biased, as it were. You’re supposed to be explaining issues and risks and backgrounds, but you do represent an organization, and your duty is to that organization. So you’re helping them navigate the various rules, regulations, decisions, what have you, entering into contracts, understanding risk.
As an expert witness, you’re being asked to take the experience and knowledge you have and cast it in a very narrow way. You’re working with very specific instructions that are given to you by either the law firm or the group of economists you’re working with, and they’re not really asking you for general counsel advice or how to navigate a contract. They’re asking you to apply your knowledge and experience to a very specific question, perhaps, within the strictures of the directions they are giving you. So even if there is a very broad question about your area of expertise, the law firm or whoever hires you is focusing you, and drilling down to very specific questions that you need to address. Now, that happens sometimes as a general counsel, but it’s just a very different kind of expectation and a very different process.
Dan Martin: Kind of interesting, but it seems that you’re also dealing with people who know less about the subject than you. Right?
Joseph Tedeschi: That depends. The law firms and the economists who reach out to Eleven Canterbury, at least as far as I’ve seen, and for my colleagues at Eleven Canterbury, we’re dealing with pretty rare air. So, the people I work with are extremely expert in their areas. And it is very complimentary, but they needed someone with my additional expertise in one aspect of it.
One of the challenges, and one of the things I really enjoy about this is that your knowledge, your experience, and your ability to communicate it are under scrutiny from very, very serious experts in their field.
It’s not so much that anyone knows more or less, but it’s a very interrelated set of expertise addressing a question. I was an M and A lawyer, and it’s very complimentary in the way that when you practice in mergers and acquisitions, often when you’re the lead lawyer, you’re the hub and spoke because you’re bringing together expertise in tax, and HR, and finance, and accounting, and regulatory.
And so expert witness work is similar except I’m one of the spokes now, trying to address a very large issue or question that may be before a court, or a tribunal, or otherwise.
Dan Martin: So, basically, it’s as you’ve said, relying on very detailed knowledge. It just always struck me as a little bit challenging. You’re trying to convey something to people in the court who don’t know about the subject in an environment where you’re not exactly controlling the way the information goes. Somebody else is asking you questions, and you really have to be kind of careful.
Joseph Tedeschi: Yeah, you have to be very careful, and I would say the prime lesson I’ve learned is, and this goes back to your original question, Dan, as a general counsel, it is generally expected that you are going to give an answer. You are going to find a way to navigate and actually say, I suggest we do this, or I suggest we do that, or, these are the risks you need to understand, and this will help you inform your decision. When you’re an expert witness, the expectation is you’re not the tribunal. You’re not conclusory. You’re not looking at the facts and saying this is the answer. What you’re doing is you’re looking at the questions and the facts and saying, based on my expertise, this is how, for example, people acting in the market would understand it, or this is how people in similar situations in corporate transactions that I’ve worked on would understand the provision of a contract.
So what you’re trying to do is provide a useful and valuable perspective to help others make a decision. But you’re not, you can’t put yourself in the shoes of the tribunal or the court or even of the law firms, right? They ask you a question, and you’re applying your knowledge to that answer.
The other difference then is, when you’re a general counsel, it’s rare that one of your clients would ask you what a contract is, or what equity is, or, you know, what a specific term is. But when you’re an expert witness, you have to go back almost to that academic side and really explain things at their most basic elements because you have to justify your expertise.
So, if you’re an M and A lawyer and you’re sitting across from another lawyer and you’ve been working on these things for 20 years, no one is asking you to go back necessarily to those fundamentals you’re acting in the market. Here you really, really have to go back to fundamentals to justify your expertise, and that’s a real challenge because people like myself who have been practicing for a long time, again, you become a practitioner, and here you have to go back and really, really go back to first principles of your expertise. I personally really enjoyed that, actually. I felt like I was back in law school, in a sense, or writing a law review article.
Dan Martin: It sounds kind of cool. It reminds me a little bit of people moving from being an operating executive to being on the board, where it’s a different skill set, and you have to think about things in a completely different way. Even though they’re sort of still involved in the successful operation of an organization.
Do you like the fact that the work as an expert witness is episodic? I think in your case, you’ve done a fairly extensive engagement, but you also have time for being on the dance company.
Joseph Tedeschi: Well, that’s a great point. I mean, I’ve always balanced my work in the corporate world and things like that with a passion for the arts and trying to do as much as I can in nonprofit work. So actually, it’s two things. I’m on the board of an organization called the Volunteer Lawyers for the Arts in New York, and there we are the largest network of lawyers who provide pro bono work to nonprofits and artists engaged in art. The dance company is much more personal for me. My wife happens to be a choreographer and a dancer, and I used my expertise in nonprofits to help her career. And so together we formed a nonprofit dance company that we’ve been operating together for about seven years now, although her career is longer and more illustrious than the nonprofit itself. But yeah, it’s very interesting. I go back and forth between these different activities, but, you know, that’s the stuff of life. That’s what makes it interesting. In fact, much like an expert, a couple of weeks ago, I taught a class at Fordham Law School for dancers and choreographers, trying to help them to understand the basics of how to navigate a complicated world of contracts, employment law, and intellectual property that they face as artists. So I like mixing the practical with the academic and the theoretical, for sure.
Dan Martin: Well, it sounds like you’ve found a wonderful way to celebrate the next chapter. Thank you very much, Joseph.
Joseph Tedeschi: Dan, I appreciate you and the opportunity to do this work and to talk to you about these interesting issues. Thank you very much.
