CLIENTSPEAK: Amy Osteen, Outside CLO, PC

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The CLIENTSpeak Q&A below is from a recent interview we conducted with Amy Osteen, founder of Outside CLO, PC, a fractional General Counsel firm.

Amy currently serves as General Counsel for a Dallas-based technology company, a Michigan-based product company, and a DFW medical practice. Before Outside CLO, Amy was Chief Legal Officer of Rug Doctor with direct responsibility for multiple departments, including legal, insurance, real estate, and human resources. Before Rug Doctor, Amy was General Counsel of Zimbra, Inc., wholly responsible for all legal aspects of Zimbra's global, multi-channel, software business, and 100 million+ end users. Before Zimbra, Amy spent 10 years as Assistant General Counsel of ORIX USA Corporation, focusing on portfolio investments, litigation, IP, M&A, corporate compliance, and financial product compliance. Amy is also a member of the Texas and United States Patent & Trademark bars and on the Emerging Leaders Board of SMU Dedman School of Law.

Amy has two littles (Micah, 9 and Maddox, 7), a co-dependent Schnoodle named "Bizou," and she recently married Michael Gulley, an eCommerce programmer, in October. Just in time for quarantine!

Q: What factors influence whether you hire outside counsel?
A: Three primary factors influence whether I hire outside counsel: Project importance, Time, and Expertise. Is the project revenue generating or involve increased risk? Do we have the time to do the work in-house? Do we have the expertise to do the job in-house? If the project is a priority that can’t be delayed until a “slow spot,” and we either don’t have the time or expertise to handle the matter effectively, I turn to outside counsel.

Q: What are some things that outside counsel have done that have made a positive impression and/or impact?
A: A striking difference between practicing at a law firm and in-house is how much more each decision you make is rooted in business. The best outside counsel are those that help me seamlessly navigate business and legal issues – while teaching me so I can make better decisions. As an example, I used Eric Pfeifle (Holland & Knight) on a refinancing transaction. Even though he was busy, he’d take the time to explain why they marked something up and how the provisions worked in different business scenarios. He taught me his craft as we worked through the document, and that’s invaluable.  

Q: Do in-house counsel care if your outside counsel is a super/best/elite lawyer?
A: In my experience, not really. But, if in-house counsel doesn’t have an established relationship with the outside counsel and they need to convince the management team the selection is solid, sometimes forwarding an article or award gives management the comfort to support the selection and expense.

Q: What law firm trends are you seeing that you would like to either end or continue?
A: Fifty years ago, the ABA declared that “there are . . . approximately 1,300 fee-earning hours per year.” Yet now, many law firms expect attorneys to bill at least 2,000 hours annually. Aside from the work-life balance issues, outside counsel expected to bill 2,000 hours a year are stretched thin, prone to mistakes, difficult to reach, and often saddle their clients with tons of “billable waste”: fees paid to someone other than the attorneys performing the work. Many have learned from this time working remotely that it benefits everyone to leave behind the intense billable requirements, fancy office space, partner boondoggles, and billable waste. Adam Forest of Scale, LLP wrote an article on Medium that is a great read, Your New Remote Law Practice is Better. Why Go Back?

Q: What advice would you give to a junior associate at a law firm?
A: (1) Try to get varied experience. So many associates are forced to hyper-specialize, which often, is not fun or a long-term game plan. Try to work in multiple sections and with different partners. (2) Nobody becomes better at their craft by always asking for approval and fishing for compliments. Continuously identify areas of weakness you want to improve. Continuously identify decisions you could make instead that turn it into an area of strength. Then, consistently, make those decisions stick. Follow this process, and you’ll see dramatic changes in your legal career – and life.  

Q: Is there one resource you use over another when soliciting referrals from colleagues for outside counsel?
A: The pressure on in-house counsel to make quick and thoughtful decisions on outside counsel in an unclear and changing world would be unbearable without our networks. If I don’t have direct experience with counsel in an area, I hit up my network of in-house friends. “Hey, Brandon, you have any bad @#$ litigators in Nevada?” “Katie, when you had that case in Chicago last year, who did you use and would you use them again?”

Q: What are the biggest mistakes outside counsel can make? (What should law firms avoid?)
A: Looking at your client as a short-term project creates worlds of problems. In my experience, the most valuable attorney in the room is usually not the one who talks the most, or the loudest. It’s often not the one who strides in wearing the most expensive clothes or even the one who gives the most polished speech. More often than not, it’s the attorney who takes the time to research the client’s business (not on the client’s dime). It’s the person that asks around about the client’s market (not on the client’s dime). It’s the outside counsel that puts in the time to figure out what they need to know to be a long-term partner (not on the client’s dime).