“One is the loneliest number that you’ll ever do.

Two can be as bad as one, it’s the loneliest number since the number one.”

 “One” Three Dog Night

I appreciate everyone who writes to me about the blog.  In particular, I enjoy your suggestions for future blog posts and I always add them to my list of ideas.  Today, I am writing on a topic that several readers have asked me about – how to deal with being the only lawyer in the department, a/k/a the “loneliest number.”  First, I think being an in-house lawyer is the best job in the legal profession.  I say that having always been part of a good-sized legal department:  at American Airlines, at Sabre Corporation, and now here at Marketo.  The smallest department I have been associated with was my first year at Travelocity when there were five of us (one year prior to acquiring another online travel company in London which added several more to the team).  I have never been a solo general counsel or member of a really small team.  So, I have been a little hesitant to write about something where my experience is somewhat lacking.  Having thought about it, however, I think I have enough general experience to share some thoughts on what I would be looking for – or doing –  if I were to ever become a legal department of one.  I think the ideas below also work well for someone who is part of a relatively small department.

I start with thinking about what drives someone to accept a position as a solo general counsel.  I imagine that it is probably a combination of wanting to build something from scratch, of wanting to do it your way, and the potential for a substantial economic payoff down the road when the small or start-up company gets “big.”  Additionally, I suspect someone wanting the “Lone Ranger” role enjoys the rocket-like pace and the challenge of being the only lawyer at a company.  Regardless of your reasons, this edition of “Ten Things” discusses what you need to do and watch out for if you want to succeed as a legal department of one:

1.   Clarify your role.  The first thing you need to do before accepting the role as the lone lawyer is to clarify exactly what your role will be.  Are you expected to be part of the executive team and a trusted advisor to leadership and the Board of Directors, or are you simply going to be a scrivener whose job is solely to draft contracts and manage any outside counsel?  While it’s likely to be some combination of both, be sure to get your role, duties, and expectations nailed down before accepting the job.  And if you do nothing else, get all promises about your job, compensation, bonus, equity, etc. in writing.  If you are a lawyer reading this, I am sure I do not have to explain why.  If you cannot get something in writing from the company, then document back to the company your understanding of the offer and all of the promises made to you.  While not perfect, it’s better than nothing and, if unrefuted, it will be very useful in the event of a problem down the road when people start to “forget” what was promised.

2.  Gut check.  Before you say “yes” to becoming a solo general counsel you need to stop for a gut check.  Is this really what you want to do with your career?  It takes a special type of lawyer to be the only in-house counsel at a company.  First, I wouldn’t take on a job like this unless I had at least four years of experience (and more is definitely better).  Second, are you ready to give up the perks and “cushy” lifestyle of working at a law firm or a big in-house department?  In this new job, you will need to be almost completely self-sufficient and ready to work long hours to ensure everything gets done.   You may no longer have an office with a door or even a cubicle.  More likely you will sit a long table with other employees and your rank as general counsel will not mean a whole lot.  Third, get ready to fly by the seat of your pants when making legal decisions.  You will need to become the ultimate do-it-all generalist – a legal Swiss Army knife.  You will not have the time, generally, to go to outside counsel (if that’s even an option), nor will you be able to spend hours researching the problem.  On a daily basis, you will make important decisions with less than perfect information in areas of the law where you have little to no background.  Are you comfortable with this?  Fourth, be ready to take on and get comfortable with more risk than you’ve ever experienced in your legal career.  Your orientation will quickly become more “business” than “legal” much of the time.  You must learn how to analyze risk quickly and lay out the options for the business and, ultimately, live with what the business decides it needs to do.  This takes a strong stomach.  Finally, the odds are high that your compensation in terms of salary and bonus will be low with some front-loaded equity so that if the company takes off you are very well rewarded.  Can you make this type of initial financial sacrifice and wait on the “if”?

3.  Get scrappy.  Unless the situation is very unusual, becoming the general counsel of a start-up or small company means you will need to be very frugal.  Money will be at a premium and there will be tremendous pressure to limit expenses.  You may have no budget for outside counsel or what you do have will be tiny.  You will need a very fast education in how to be “legally frugal.”  Further below I identify some specific free on-line legal resources, but here are several things to focus on generally:

• Find a boutique law firm or solo practitioner.  You can seriously stretch your legal budget by ditching “Big Law” and finding a small firm or even a solo practitioner to help with legal work.  Try to find an individual who previously worked for a “Big Law” firm and then decided to step out on their own or as part of a small boutique firm.  The work will be five-star quality but the price will be drastically lower.
• Find free CLE, “boot camps,” and seminars.  If you look, you’ll be amazed at how much free CLE, “boot camps,” and seminars are available to you, either in person or via webinar.  Take advantage of these opportunities to learn and hone existing or new legal skills at no cost.  You typically get great materials, including forms and checklists by attending.  You can sign up for free client alerts on the web sites of most major law firms.  Once you do, you will often get offers for free CLE/webinars.
• Free law library.  Many law schools provide guest access hours to their collection at no cost.  Likewise, many state and federal courthouses provide access to their law library at no cost.  Large city libraries often have sections devoted to legal books and publications.  Take advantage of these if you can to make up for the lack of a library.  And if there is a book you use frequently in your practice check to see if it is available for free on Google or at a discounted price (used or new) on Amazon or eBay.
• Specialized Blogs.  You can find a lot of free guidance, information, and forms on legal blogs dedicated to the sole general counsel or start-up company lawyer.  Start-Up Company Lawyer is a great one to start with.  Also check out Start-Up Law 101 and The Ultimate List of Legal Resources for Start-Ups.

4.  Learn the business.  No surprise here, in order to be a successful in-house lawyer whether it is part of a large department or as a solo general counsel you need to learn the business of your company, most importantly how it makes money.  That said, learning the business takes on even more significance for a solo general counsel because you will be expected to know everything, vs. just the part of the business you might be responsible for as a member of a large department.  The best way to do this at a start-up/small company is the following: a) read everything you can about your company or produced by your company (especially any documents prepared for investors); b) get product demos so you can “see” what your company’s products do and how they are used by customers; c) ask questions.  If you don’t understand something be sure to ask someone to help you understand; d) make a friend or two in the business who can help guide you in learning about the company (more friends the better); and e) understand basic business finance including how to read a balance sheet, income statement (P&L), and cash flow statement.

5.  Get Practical Law.   I know I sound like a broken record in this blog when I say that the single best resource an in-house attorney can get is Practical Law.[1]  This is even more so if you are a single in-house lawyer or part of a small team.  Simply put, Practical Law can give you the guidance, research, forms, checklists, “what’s market,” sample policies, practice notes, global coverage, toolkits, etc. you need.  All in an incredibly “practical” and useful way.  Literally, everything you need to answer just about any legal question or request put to you by the business.  It’s not free, however, so you will have to pay for a yearly subscription (but I would fight for this as part of coming on board).  If you don’t already use it, my suggestion is to sign up for a free trial and get a demo.  If Practical Law is not in your budget, all is not lost.  There are several free resources out there that can provide a well of useful information at no cost (as well as some low-cost tools).  Here are just a few:

• Getting the Deal Through – GTDT is free to in-house lawyers and provides a multitude of legal guides that quickly summarize the laws of multiple nations on a particular legal topic.  For example, if you need to know merger clearance in Chile, or arbitration in France, or IP law in the USA, it’s here.  All written by top law firms practicing in each jurisdiction.  Even if you have Practical Law, GTDT is a site worth bookmarking.
• Lexology Navigator – Similar to GTDT, though not as comprehensive, this is a free site where prominent law firms write detailed articles on numerous legal topics listed by jurisdiction.  Want to know how patents work in Mexico, or employment law basics in Canada, or enforcement of foreign judgment in Norway, here you go.
• Lexology.com – The is a newsfeed service that captures the best of law firm publications and client alerts.  In its own words “Lexology delivers the most comprehensive source of free-to-access legal updates, analysis and insights. We publish in excess of 450 articles every day from over 800 leading law firms and service providers worldwide across 50 work areas in 20 languages. Our searchable archive now contains more than 650,000 articles. Our combination of timely, quality, granular information and relevant insight supported by our intuitive, innovative technology provides an unparalleled user experience.”  Go to the site, enter your areas of interest, and every day you will get an email with a ton of helpful information and top-notch analysis of those legal areas.  I read this every day.
• Justia.com – A helpful free mishmash of links to case law, law reviews, blogs, contract forms, etc.
• Harvard Guide to Free Legal Resources – Our good friends at Harvard have produced a lengthy list of links to free legal resources.  If you can’t find it anywhere else, it’s worth trying here.
• Google Scholar – Well, it’s Google.  If it’s on the web, you can probably find it here.
• Rocket Lawyer – lots of free form agreements.
• Business in a Box – Silly name, but for the nominal price of $199 you can get access to a plethora of form contracts and other documents.  All very well written and useful (I have a subscription myself).  For $100 more you can get the same in multiple languages (and two more licenses).  This could be the best $199 any in-house lawyer has ever spent.
• Artificial Intelligence – as AI becomes cheaper and more user-friendly, I would look for AI that can assemble contracts, review contracts, provide research, and/or do other tasks that will reduce the amount of “rote” legal work on your plate.  This will allow you to focus on more value-adding work with no additional headcount.  Look at tools like LawGeex, Determine, or Ross Intelligence.   AI has to potential to truly delivery on “doing more with less.”

6.  Fix the basics first.   If you’re going to work for a start-up or small company, odds are good that there is a lot to fix from a legal angle.  You must keep in mind that you cannot fix it all, certainly not at once.  So, you need to focus on the basics first.  Here is the list I would walk in with:

• Fix the basic corporation documents (i.e., articles of incorporation, by-laws, LCC documents, etc.) as it’s likely these were probably prepared by the founders using a “do it yourself” form and can use updating.
• Clean up or prepare the “cap table,” a spreadsheet or chart that shows who owns what in terms of equity of the company.  This will be extremely important as the company matures and/or takes on investors, especially when it comes to the founder’s understanding about getting diluted in the first round of financing.
• Get the right human resources policies in place as it’s likely HR has been an after-thought at the company.  This is a place where Practical Law can be a goldmine of forms and checklists.  Keep an eye on the company culture, especially if it’s basically a “frat house” which is a recipe for lawsuits down the road (just ask Uber).
• Prepare form agreements for the company’s most used contracts and install a repeatable contracting process.  For this, Practical Law, Business in a Box, or Rocket Lawyer can be a huge help.
• Get on top of data privacy and data security issues.  Watch out for the GDPR which applies to any company that processes the data of EU citizens regardless of where the company is located.  I have seen a lot of small or start-up companies be surprised when customers start demanding GDPR compliance.
• Protect the company’s intellectual property, i.e., trademarks, patents, copyrights, and trade secrets.   For many small companies, IP is the crown jewel and if it gets improperly copied or stolen then all the value of the company falls away.

7.  Build a network.  You may be a department of one, but you are not alone.  Focus on ways to build a network of lawyers (in-house or outside) that you can talk to and bounce ideas off of.  Building such a network allows you to “expand” your department without adding headcount.  Consider joining organizations like the Association of Corporate Counsel or the American Bar Association and tap into their groups and committees dedicated to small legal departments.  Look for legal message boards and listservs where you can post questions, ask for forms, etc.  Likewise, many metropolitan areas have organizations comprised of general counsel that meet regularly and discuss topics of interest to the group (and encourage members to email the group with questions or seeking forms or recommendations, etc.).  Or, create your own organization of general counsel at small or start-up companies to accomplish the same results.  The key is knowing that you can have a network of in-house lawyers in similar positions who can help and share resources.

8.  Think about the future.  You may be all by yourself today, but down the road, you may have the opportunity to expand the department and start to hire paralegals and lawyers.  You should be thinking about expansion from day one.  As you go about your daily work, keep notes about what legal issues the company is facing and – if you had the chance – how would you expand the legal department to deal with those issues.  Keep track of how much money you are spending with outside counsel and how bringing that work in-house would reduce those costs.  Or, if there are contracts that are lost or substantially delayed because you don’t have the time to deal with them, capture that cost as well.  Ultimately, you’ll want to present a compelling business analysis of why adding headcount to Legal make sense for the business.  Also check out the ACC’s Guide to Establishing a Legal Department.

9.  Prioritize/Delegate.  If you take this job, you will need to become an expert in two things: prioritizing and delegating.  As to the former, it’s obvious that you will have way more on your plate than you can possibly get done even if you worked 24/7. So, come prepared to hone your ability to decide what needs to be done now and what can wait.  Fortunately, for most lawyers, the ability to prioritize seems to be in our DNA.  It’s how we survive.  If it’s not instinctual, then brush up on the basics.  My guiding lights were always “urgent vs. important” and “value.” The more urgent and the more valuable (either in creating value or preventing value destruction) got to the top of the pile.  Similarly, even if you are the only lawyer, it doesn’t mean you cannot delegate.  Hopefully, you at least have a kick-ass assistant and in my experience assistants can do way more than answering the phone and keep your calendar.  In fact, you should tell your assistant to let calls roll to voice mail and that you will keep your own calendar.  Instead, figure out what types of tasks your assistant can take on for you.  If it doesn’t require a law degree to accomplish it is “game on” for delegating.  In addition to your assistant, consider whether there are others in the business who can take on tasks you have been saddled with.  For example, can someone in sales be trained to do contract in-take and gather all the information you need to begin to draft the contract (or if it’s a form contract, can they do the first “draft” of the form for you)?  Your pool of available people to delegate to is only limited by your imagination (and their willingness to help).  You can also reduce your workload by being a teacher and training employees in your company on things like “writing smart,” data protection, contracts 101, negotiation, and so on.  The more you can teach someone to handle certain tasks or avoid problems, the less work that will end up on your plate.

10.  Know who to please.  This is the hardest task of all, especially in a small company.  Remember that you are not the founder’s or the CEO’s lawyer, you are the company’s lawyer.  This is usually not an issue when the founder is the only shareholder and is the sole board member, but when other investors come on board you must be aware that you now, under the rules of professional responsibility, represent all the investors, “management” as a whole, and the board.  You must seek to do what is in the best interests of the company and not any one employee.  In other words, you represent the entire box of Milk Duds and no particular dud (damn, that didn’t work as well as I thought it would, but you get the point).  Doing this is easier said than done.  One way to get it right is making it part of clarifying your role before you join the company.  Regardless of who you represent, it is important to show value every day.  Most likely, you were hired because the cost of outside counsel became greater than the cost of your salary.  You must continuously show that management made the right decision.  Keep senior management up to date on what you’re working on, make sure they know your key accomplishments, and always focus on showing them how they are saving or making money by having an in-house lawyer vs. going outside.  Finally, as mentioned, the risk profile of a start-up/small company is vastly different than a large, established company.  You need to quickly get into “Dr. Yes” mode and drop “Dr. No.”  This doesn’t mean you cave on everything, rather you must be sure you understand what risks the company is willing to tolerate and then adjust your legal thinking accordingly.  Sure, it may be risky to accept uncapped liability in a contract but it may be the only way a start-up/small company can start to gain customers.  Don’t say “no,” say “we need to get some insurance!”

*****

It takes a very special lawyer to be a legal department of one.  If this is the path you have chosen (or are considering), I greatly admire you.  I don’t know if I could do it.  That said, I don’t mean to imply that every start-up or small legal department operates on a shoestring.  Many do not.  But for those that do, I think the keys for someone going into that job are fully understanding what you are getting into, turning frugality into an art form, and learning to be way more aggressive than you might normally be.  And, if you’re able to get smart fast and work at a lightning pace, this might be the life for you.  If any readers who are “departments of one” want to comment on some of the things they have learned or do to stay sane, please write a comment below or post on LinkedIn.  Your real-life experience would be very valuable.

Sterling Miller

January 31, 2018

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[1] For full disclosure, I do write a column for Thomson Reuter’s (the owner of Practical Law).  However, I do not get paid in any way -nor asked – to endorse the product, this is just my own opinion as a long-time user.