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How to thrive as a solo general counsel

Sterling Miller

Sterling Miller knows in-house life, from leading the legal team for Sabre Holdings’ successful IPO back during the original Internet boom to three stints as General Counsel of dynamic, nimble companies to his current role as CEO and Senior Counsel of Hilgers Graben. We asked him to share his hard-won experience and thoughts on what it's really like to sit in the big chair, to inform the next generation of first-time general counsel. Here’s what he has to say.

Being an in-house lawyer is a great job. You do not have to spend time on business development, collecting fees, or tracking your time. More importantly, you get to be a key part of the business with a seat at the table when critical decisions are made. That said, you only have one client, and you must do your utmost to keep them happy, which can be pretty challenging some days.

Most in-house lawyers are part of a team so they can share the burdens and challenges. Some teams are very large (like a regional law firm), and some are small, with only three or four people. The most challenging of all, however, and potentially the most rewarding, is taking a position as the only lawyer at the company - the solo general counsel. It is actually fairly common, as the Association of Corporate Counsel notes, that 22% of in-house lawyers are solo general counsel. Someone who accepts this role is likely looking to build something from scratch, wanting to do things “their way,” and hoping for a substantial economic payoff down the road when the small or start-up company gets “big.”

Moreover, to succeed in such a role, you must be someone who enjoys the rocket-like pace and the challenge of being the only lawyer at a company. Regardless of your reasons, there are a number of things you must know or do to thrive as a solo general counsel.

I. Clarify your role from the start

The first thing you must do before accepting the role as the solo general counsel 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 going to be a scrivener with a great title whose job is solely to draft contracts and manage 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. Get all promises about your job in writing:

  • Compensation
  • Bonus
  • Equity
  • Vacation
  • Budget
  • Severance
  • Bar dues and fees to join certain organizations
  • Resources/Technology
  • Office location
  • Ability to work remotely
  • And anything else someone told you was part of the offer that enticed you into accepting the role.

If it is not in writing, then it is likely illusory. Even something like a change in CEO or CFO, chief financial officer, can make any oral promise worthless. If you cannot get something in writing from the company, you should think very carefully before accepting the job. If you still wish to move forward, then document back to the company your understanding of the offer and all the promises made to you. While not perfect, it’s best to be prepared for what could happen down the road in the event of any problems. Additionally, consider asking that your compensation and equity be pegged at that of your peers in the C-Suite. Otherwise, you may find yourself out of the range of expected compensation. That said, it is on you to do research on what is market for the position in terms of compensation.

II. Do your due diligence

When joining any company, especially a small one or start-up, take some time to conduct due diligence to help you verify that it is financially sound and maintains reasonable ethical standards. Here are some steps you can take: 

  • Financial. Locate any annual reports and financial statements. If the company is publicly traded (unlikely in this case), you can access these online. If not, ask for copies of the last two years of financials at least. Talk with the CFO about the financial health of the company and ask her to walk you through the current P&L, cash flow statement, and balance sheet. Ask if the company has a credit rating and, if so, to see it.
  • Ethics. Search for the company in news outlets to uncover any recent controversies, legal issues, or scandals. Platforms like LinkedIn and Glassdoor can provide insights from current and former employees about the company culture, management practices, and ethical considerations.
  • Company culture and values. Ask to see the mission statement and values. Review the company's website and public documents to better understand its mission, vision, and values. Glassdoor and Indeed offer employee reviews that can give you a sense of the company culture, work-life balance, and management's approach to ethical practices. Note that you will likely see more negative comments than positive ones. Take everything you see (good or bad) with a grain of salt.
  • Use your network. Reach out to current or former employees within your network for their insights and experiences.
  • Legal and compliance check. Research to see if the company is currently involved in any significant legal battles or has a history of legal issues.

This is a big decision for you, likely coming with a lot of promises around compensation and upside. Do your due diligence so you can make an informed decision for you and your future. If the company tries to discourage you from doing so, it is likely not the right fit for you.

III. Gut check

Before you say “yes” to becoming a solo general counsel, you need to stop for a gut check. It takes a special type of lawyer to be a solo general counsel. Consider the following:

  • Do you have at least four years of experience? (And more is definitely better as we will see below). While it may sound exciting to be the general counsel, you will be making a lot of decisions on the fly and with intense pressure from the business. It is much easier to help the business get to the right decision when you have several years of experience under your belt.
  • Are you ready to give up the perks and 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. You may sit at a long table with other employees and your rank as general counsel will not mean a whole lot. 
  • 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 within your company’s budget), nor will you be able to spend hours researching the problem. Daily, you will make important decisions with less-than-perfect information in areas of the law where you have little to no background. Is this level of ambiguity something you are comfortable with? 
  • Have you thought about the level of risk you’re willing to work within? Your orientation will quickly become more “business” than “legal” most of the time. You must learn how to analyze risk quickly, lay out the options for the business and, ultimately, live with what the business decides it needs to do. This takes a strong stomach. 
  • Are you willing to change how you think about compensation? 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.

IV. Where did the money go?

Unless the situation is very unusual, becoming a solo 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.” Focus on these to start:

  • Review outside counsel and vendor spend. Get a complete picture of all the company’s legal spending over the past several years (in-house counsel and vendors). Identify the firms and vendors by name. You will likely see that the company is using the wrong size firms for legal work.
  • Find a boutique law firm or solo practitioner. If you have any budget for outside counsel, you can make it go a lot further by ditching “Big Law” and finding a small firm or even a solo practitioner to help with legal work. Even if you come from a big law firm, you will quickly realize that you likely cannot afford your former colleagues. In fact, you may wonder how anyone affords Big Law rates. Instead, try to (i) renegotiate rates to something reasonable for the company or (ii) 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 high quality, but the price will be drastically lower. If so, then you will be able to save the company a lot of money vs. what it was spending or likely would spend.
  • 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. Start with a simple internet search looking for “free CLE.” 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 websites of most major law firms. Once you do, you will often get offers for free CLE/webinars. Thomson Reuters is a great resource and has a variety of webinars that cover a broad range of subject matter.
  • Free law library. Many law schools provide guest access hours to their collection at no cost, including online access to their alumni. 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. State bar associations also have free resources you can take advantage of. 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. Here are some additional free or low-cost legal resources: Harvard Guide to Free Legal Resources, Google Scholar, Rocket Lawyer, and Business in a Box.
  • 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. The Thomson Reuters legal blog is a great one to start with. Also, check out the Ultimate List of Legal Resources for Start-Ups.

If you can negotiate resources upfront before joining as a solo general counsel, Practical Law is consistently rated as the single best resource for in-house lawyers, especially solo general counsel. Practical Law can give you the guidance, research, forms, checklists, “what’s market,” sample policies, practice notes, global coverage, and toolkits you need, all in an incredibly practical and useful way. You will find resources on everything you need to answer just about any legal question or request put to you by the business.

V. Learn the business

In order to be a successful in-house lawyer whether as 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, versus 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 or small company is as follows: 

  • Read everything you can about your company or produced by your company, especially any documents prepared for investors.
  • Get product demos so you can “see” what your company’s products do and how they are used by customers.
  • Ask questions. If you don’t understand something, be sure to ask someone to help you understand.
  • Make a friend or two in the business who can help guide you in learning about the company (the more friends, the better).
  • Understand basic business finance including how to read the Big Three: a balance sheet, income statement (P&L), and cash flow statement.
  • Meet with all the senior leadership of the company and ask about expectations, how they prefer you communicate with them and how frequently, what they want from a legal function, what they don’t want from a legal function, and how you can best help them succeed. This is also where you will have the ability to note that you are a legal department of one, with a small if any budget. There will be limits to what you can do.

VI. 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. Still, you cannot fix it all, and certainly not at once. So, focus on the basics first, i.e., where you (and the company) will get the biggest return on your time. Start with:

  • Fixing 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.
  • Cleaning up or preparing 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.
  • Getting the right human resources policies in place as it’s likely HR has been an afterthought at the company. Keep an eye on the company culture, especially if it’s basically a “frat house” which is a recipe for lawsuits down the road.
  • Highlighting meat and potatoes compliance, i.e., a business ethics policy and antitrust training to start.
  • Preparing form agreements for the company’s most used contracts and install a repeatable contracting process
  • Getting on top of data privacy and data security issues. Watch out for GDPR which applies to any company that processes the data of EU citizens regardless of where the company is located. And, remember, that more than a dozen U.S. states now have their own data privacy laws.
  • Protecting 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.

VII. Prioritize and 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 24/7/365. 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 is in their DNA. It’s how they survive. If it’s not instinctual, then brush up on the basics. A good guiding light is an “Eisenhower Matrix” where you focus most (but not all your time) each day on matters that are “urgent vs. important.”

Another rule of thumb is focusing on the highest revenue-generating contracts as those are the lifeblood of any small company or start-up. The more revenue coming in, the better for the company (and you). Similarly, even if you are the only lawyer, it doesn’t mean you cannot delegate. Hopefully, you at least have an excellent assistant who can do way more than answer the phone and keep your calendar. 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.

Also, consider whether there are others in the business who can take on tasks you have been tasked with. For example, can someone in sales be trained to do contract intake 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)? Push back on things that are not really the responsibility of the legal department. While it's pleasant to feel needed, it's important to avoid becoming the default recipient for others' tasks. Stand your ground here (and get clarity on this before you start). You can also reduce your workload by 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. Checklists are great tools here.

VIII. Get comfortable with “good enough”

Perfection is the enemy of the practical. No one likes to be wrong, but in-house lawyers — especially a solo general counsel — rarely have the time or budget to track down every possible thread that could get pulled to unravel their answer. Accept that “good enough” is usually good enough. If you can reuse material, don’t reinvent the wheel – use the wheels lying around the office. Most issues can and should be handled quickly and routinely.

There will be matters when you will need to spend more time, and it’s important to clearly identify those. If the board of directors is involved or it’s a “bet the company” issue, then you need to take the time to solve the problem exactly right. But those instances are generally rare.

Your daily responsibilities largely involve producing a significant amount of work efficiently while maintaining a balance that aligns with the company's acceptable level of risk, which may be higher than what you, as a legal professional, might typically be accustomed to. There might be an error in there somewhere (though a good checklist is a good way to avoid the most glaring errors). It happens. The sky will remain intact, so let's shift our focus and energy to the next project.

Here's what to focus on when deciding what is good enough:

  • Understand the business objectives. Recognize the business goals and how your legal work aligns with them. If you can sufficiently mitigate risk without impeding the business objectives, it can be considered good enough – additional efforts may yield diminishing returns.
  • Resource management. Consider the resources (time, manpower, budget) available. If additional effort will result in minor improvements at a disproportionate cost, it might be time to stop.
  • Deadlines and timeliness. In many cases, meeting a deadline is crucial. If additional work will cause significant delays that could impact business operations or opportunities, it might be better to prioritize timeliness. Evaluate the significance of the task. For high stakes matters, a higher level of thoroughness is warranted. For less critical tasks, go with “good enough.”
  • Ask. Talk with your business colleagues. If they are satisfied with the work and believe it meets the necessary standards, it might be fine to stop.
  • Be practical: Legal solutions should be practical and applicable. Over-analysis or striving for perfection in every aspect can be counterproductive. Use past experiences and outcomes to gauge what level of detail and thoroughness is typically required and has been successful.
  • Avoiding analysis paralysis: Be wary of overanalyzing to the point where it hinders decision-making or action. Sometimes, making a decision, even if not perfect, is better than indecision.

IX. 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. Building such a network allows you to “expand” your department without adding headcount. Consider joining organizations like the Association of Corporate Counsel groups and committees dedicated to small legal departments. Look for legal message boards and listservs where you can post questions and ask for forms. 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 seek forms or recommendations). 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. groups and committees dedicated to small legal departments. Look for legal message boards and LISTSERVs where you can post questions and ask for forms. 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 seek forms or recommendations). 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.

X. 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 lawyers and staff. 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 have the chance — how you would 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 lost opportunity cost as well. Ultimately, you’ll want to present a compelling business analysis of why adding headcount makes sense for the business.

XI. Know who your client is

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. 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. You must continuously show management that they made the right decision by hiring an in-house lawyer.

Start by simply keeping senior management up to date on what you’re working on, your key accomplishments, and showing how they are saving or making money by having an in-house lawyer versus paying for outside counsel. Finally, get into “Dr. Yes” mode fast and leave “Dr. No” behind. This doesn’t mean you cave on everything, just be sure you understand what risks the company believes are worth taking – legal doesn’t run the business. Taking risks may be the only way smaller or start-up companies can get their legs under them. You need to be ready to guide and support them as they navigate through their early stages.

Wrapping Up

It takes a very special lawyer to be a legal department of one. If this is the path you've selected or are thinking about, it could be challenging yet fulfilling work ahead. That said, not every start-up or small legal department operates on a shoestring. Many do not. But for those that do, the keys to thriving as a solo general counsel are as follows: understand what you are getting into, get it in writing, turn frugality into an art form, and cultivate a more assertive stance on risk management than you might typically consider.

If you have access to Practical Law, you will have many, if not all, of the resources needed to do the job and do the job well.

About Sterling Miller

Sterling Miller is currently CEO and Senior Counsel at Hilgers Graben PLLC. He is a three-time General Counsel who spent almost 25 years in-house. He is the author of five books and writes the award-winning legal blog, Ten Things You Need to Know as In-House Counsel. Sterling is a regular contributor to Thomson Reuters as well as a sought-after speaker. He regularly consults with legal departments and coaches in-house lawyers. Sterling received his J.D., with honors, from Washington University in St. Louis.

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