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A Conversation with Alum Cary Kleinman

We recently caught up with former Stroock lawyer Cary Kleinman. He is now a managing director of global alternative investment management firm Oaktree Capital Management, L.P., and in-house counsel for its real estate group. Cary talked about his time at Stroock, lessons learned throughout his career, the benefits and challenges of working in-house, and how outside counsel can better serve corporate clients. He also shared some practical career advice for newer lawyers.

Q: Tell me about your time at Stroock. What did you enjoy most about working at the firm?

CK: Stroock was an exceptional place to work, and the people and firm culture stand out as the highlights. There are many great law firms, particularly in New York City, however, I learned over time the importance of finding a place where you really enjoy working. I have the utmost respect for my Stroock mentors, and I’ve made many lasting friendships at the firm including those in my associate class. We were all very close and those relationships remain strong today. I keep in touch with both current Stroockies and Stroock alums and I am thrilled that Oaktree is a Stroock client.

Q: You were at a few firms before you went to Oaktree Capital. What convinced you to go in-house after years of working at law firms?

CK: I knew early on that I wanted to be involved on the business side, specifically the business side of real estate. I was waiting for the right opportunity at the right time. Shortly after moving out west, the opportunity to work at Oaktree presented itself. 

Q: How did your law firm work experience prepare you for your current role? 

CK: My law firm experience equipped me with the requisite skill set for my current position. It would have been impossible for me to fulfill my job responsibilities without that experience. While some skills can be learned on the job, determining commercially reasonable positions comes with the type of exposure to deal volume, diverse issues and the sophisticated clientele that I experienced at Stroock. 

When I was first offered an in-house role, I was only practicing for about a year and a half at Stroock. I knew enough to be dangerous and I would have been expected to hit the ground running. What you gain at a firm is in part tangible, knowledge—knowing the specifics of the transactions—and part intangible, which is the confidence component. Through experience, doing the deals and handling issues, you develop the skills and confidence needed. As I see it, the associate position at a law firm is a continuation of an attorney’s legal education. Cutting that learning process short is a big mistake. The exposure to deal volume, a diverse range of issues and client interactions, and learning about market-standard terms prepared me for my current role.  

Q: What did you learn that proved to be particularly helpful when you went in-house? 

CK: Stroock prepared me to be a better negotiator, which requires a solid command of the transaction documents. I remember the advice of Lois Weinroth – “Always understand the reasoning behind the language in a contract, and never accept the answer that it is there because it has always been.”

Q: Tell me about Oaktree Capital Management and your roles as managing director and real estate in-house counsel.

CK: Oaktree is a global alternative investment management firm with over $150 billion in assets under management. I joined Oaktree in 2006 when the company was small enough for me to know almost everyone in our domestic offices. Oaktree has grown exponentially since I joined, and I witnessed the company going from a private company to publicly listed to now majority-owned by Brookfield Asset Management.   

My title is Managing Director, and my role includes both business and legal functions. My primary responsibility is to manage transaction risk across Oaktree’s global real estate portfolio. I am often the one responding to outside counsel as to which deal terms Oaktree is willing to accept. I manage the legal process and oversee asset-level litigation, deal structuring, and employment matters relating to our real estate assets. 

Q: What do you enjoy most about your job?

CK: I enjoy making the risk control decisions and working directly with outside counsel to resolve issues. I’m always learning new things working across Oaktree’s global portfolio of properties. No day is like the prior day. While there is certainly overlap, there’s always the element of surprise, of not knowing what I’m going to face on a particular day. It’s both challenging and rewarding. I often tell people that my job is like triage in a hospital. I don’t know what’s coming in next. I’m expected to deal with it, but there’s a certain level of excitement. 

Q: It sounds like a lot of uncertainty. Wasn’t that daunting when you first joined Oaktree?

CK: Absolutely. There was no easing-in period, and I was expected to handle issues that went well beyond those typically handled by a real estate attorney. I learned whom to reach out to for assistance, and over time, I looked forward to new challenges and the element of surprise that comes along with the job. 

Q: What is most challenging from a business perspective?
When I joined Oaktree, I was the sole attorney embedded in a team of investment professionals. I was tasked with occasionally having to say “no” to more senior deal team members. When working at a law firm, if the client doesn’t want to follow your advice, you may make a note in the file and move on. When you’re in-house, you’re expected to not just give advice, but to affirmatively protect the company. It took time to earn the respect of my colleagues and to align our views on risk tolerance.   

Q: As the more junior person, where did you look for guidance? 

CK: Oaktree has a large corporate legal department, however, when I joined Oaktree in 2006, I was the sole attorney for the real estate group. I often reached out to the people with whom I formed relationships while at the law firms. Brian Diamond at Stroock provided invaluable advice, and he continues to do so today. 

Q: What can outside counsel do to make the job of in-house counsel and other corporate leaders easier?

CK: The best advice I could give to outside counsel is to always provide practical solutions along with an issues list. All lawyers know how to issue spot, but the best lawyers suggest ways to resolve the issues. No one wants to look at a long list of problems without guidance on how to resolve them. The really good attorneys get through the small stuff, point out the material issues and come up with a strategy to get the deal closed. They cut through the weeds, offer practical advice and move the deal forward. 

Q: What career advice do you have for newer lawyers?
Find your passion and do work that you find fulfilling. For some, that means pursuing the partnership path. For others, it may be working as in-house counsel. Both have their challenges and perks, and many junior attorneys have misconceptions about these career paths. It is important for young attorneys to network and do their due diligence so they can make a more informed decision about their ultimate career path. 

The second piece of advice is that the person you are negotiating against may one day be your boss. The real estate community is small, and it is important to always be professional and constructive during deal negotiations.