Episode 2: Tomorrow’s Counsel, Today - Sterling Miller’s Guide to in-house growth

Over the last seven years, Sterling Miller has reasoned, opined, analyzed, and educated the legal industry with the insights he acquired from over three decades of professional experience - condensed into one transfixing, fun, and comprehensive blog - Ten Things You Need to Know as an In-House Counsel.

While most lawyers dream of becoming a General Counsel one day, Sterling has been a GC thrice over, and across diverse organizations. He has therefore been the GC who in a sense never truly retired.

Today, Sterling acts as the CEO of Hilgers Graben PLLC, is a published author of bestsellers, and unquestionable authority in the legal industry and leadership space.

For the second episode of LegalMatters by SpotDraft, Sterling takes us through efficient GC-ing, shines a light on the need for flexible managing, and leaves sound pieces of advice for legal students and upstarts who are looking to make it big in their careers.


Everyone in the industry knows about the 'Ten Things' blog. What has your experience been writing it, and how did you start?

I started the 'Ten Things' blog soon after I retired from my role as the GC of Sabre. I intended to share my experiences and help a few people navigate their careers along the way.

In my wildest dreams, I thought I would maybe be able to get across to 100-200 readers, and that I’d do it for a year or two.

Ten Things is now in its 7th year - I am still writing and the success it has had surprises me to date. The blog has led to all kinds of great opportunities and conversations with wonderful people from across the world. I receive emails from people in Japan or Korea or Argentina, asking for inputs and my experiences. 

Interestingly, while the audience for Ten Things is global, across cultures, GCs struggle with somewhat similar challenges. This solidifies my view that there is great value in sharing information and experiences.

Given these conversations, how do you think new GCs may start off on the right foot to avoid challenges at a later stage?

The most important thing when you’re starting any job, and more so if you’re starting as a GC is to talk to as many people as possible. Starting with the C-Suite, the Senior Vice Presidents, the Vice Presidents, managers to as many people as you can talk to.

You’ll want to find out what value they want out of the legal department. Is it contracts, regulatory, data issues, or something else.

The reason you want to do that, from my experience, is - lawyers tend to focus on things that lawyers like to do. And it is easy to get caught up in that thought process and get isolated from the rest of the business.

Of course, there are some crucial tasks from a lawyer's point of view, but if that's what you’re solely focusing on and exhibiting to the business as to how you’re adding value, you’re missing the boat. From the business’ perspective, these tasks might not be equally valuable to them.

Instead, take all the available information from your conversations and use them to integrate your focus with business objectives so that your legal output is relevant to business interests and generates maximum value.

The second important thing is to - ‘forget everything they taught you about writing in the law school or law firm. It has no use as an in-house lawyer.

In in-house roles, the business is more interested in finding the answer within the least amount of time.  They don’t care about the minutiae of footnotes, article titles, or case citations. This might be hard, especially for lawyers who have spent time at law firms. Law firms will give you the time to take the detailed and documentation-oriented approach. This is in contrast to corporate environments where your stakeholders want a paragraph with just the answers.

How do you effectively tie in the legal team's objectives with the overall organizational goals?

Depending on the company’s size and maturity, it might either be done collaboratively or the responsibility of the legal team to figure this out. Startups might not have the same degree of clarity with legal operations and requirements as more mature companies with more expansive operations might.

That said, if I were a lawyer at a startup, I'd focus on 2 things -

First, the contract process. Contracts are where the value is, and streamlining that process is the most important thing that you can solve for any company, even more so at a startup.

Second, a lot of problems that you see at a startup are around culture and HR issues. Establishing a company-wide culture and matching it with legal guidelines requires organization and a great deal of sophistication. Usually, startups aren't equipped with either. We've seen this adversely affect many startups here in the Silicon Valley who have been in the news because of cultural slip-ups.

Getting the culture right is important not only because it helps teams function more coherently, but also because failing to do so generates long-term repercussions - both in administration and regulatory compliance. At startups, lawyers should closely work with the HR team and integrate their expertise about the law with the general practices of culture establishment.

On the other hand, if a company has been around for 20 or 30 years, they probably have a handle on what they want from the legal team. They may even have an existing legal department that they are looking to bolster with new hires and new approaches to problems.

When you're joining a more mature business, you are looking to either enhance their operations or are helping identify unaddressed challenges. This is because established legal departments or companies tend to get caught in the trap of doing things the same way they always have even if the “old” way may no longer be the best way.

In situations like this, it is very likely that no one has sat down and added a fresh perspective in a while. Just because there has been a way to do something forever, does not mean it is the way that adds the most value. For many situations, bringing a fresh perspective would probably be the first task for a new legal hire.

How can companies, in turn, maximize the value they get out of their legal teams?

Beyond the ability to work with imperfect information, writing coherent paragraphs, and effective people and project management - lawyers also bring a diverse and transferable skill-set to the table that goes beyond solving just legal problems.

Companies can apply these multifaceted abilities to any issue that the company faces. Smart companies realize that and are the ones who keep lawyers actively involved by inviting them to be part of non-legal discussions where such skills are important.

You've been involved in operations across both law firms and in-house positions. What do you think are the most noticeable differences between the two?

The biggest difference is that in law firms - lawyers are at the top of the food chain. Since everything hinges around a lawyer billing time, they are essentially put on a pedestal. It is why firms always focus on making life easier or building more free time for lawyers so they can focus on cranking out legal work.

Contrarily, when you go in-house, you are a cost-center that they want to minimize, despite how valuable you may be. They will be looking at how you can plug in to make business processes more efficient. You are one of the many services that help run the business. As an in-house lawyer, you have to make peace with not being number one on the food-chain.

For young lawyers moving from a firm to an in-house position, the biggest change is the velocity of the work.

Since law firms bill by the hour, there is a huge incentive for them, subject to the client’s permission, to turn every rock and spend 10-12 hours on a single project.

Within business organizations, you don't enjoy the same liberty. There is a lot of imperfect information and a lack of time to dig into all the issues with equal granularity. Sometimes, you might be presented with problems that require instantaneous answers. You have to dish out the best possible solution, within given time constraints, by prioritizing speed.

But you've had a very fulfilling career as a GC. What kept you ticking? And would you recommend an in-house career to others?

I loved every minute of being an in-house lawyer. When I first considered moving to an in-house position from my job as a litigator in a law firm, I was intrigued by the fact that corporate legal departments allow you to focus on one client and dive into their operations.

In-house roles give you the specialization to understand how your client's business operates, how decisions get made, identify existing issues, and preempt problems that might be on the horizon.

When you're at a law firm, you are generally working with multiple clients, but you don't get the same degree of understanding of their operations, which you do as an in-house lawyer.

At companies that use their legal departments correctly, you might be looped into many different things.

When I was the GC at Travelocity, they had included me in the marketing discussions that led to launching the Travelocity gnome. That is an experience you do not get at a law firm. This intimate relationship with the business - being part of the team, being asked to weigh in even on non-legal matters where you might have something to add to the conversations, is incredibly appealing.

While law firms are typically involved in putting out fires, in-house professionals are actively involved in shaping the future of the company. Here you’re an advisor - helping the business proactively and avoiding roadblocks right from the start.

An interesting in-house role in the U.S., UK, or other common law countries is - 'counselor of law.' In a counselor role, you get to exercise that muscle because - you're there at the beginning, you get to have conversations on what is the best way to do something, versus jumping in when things have already gone wrong. And you can call the outside law firm and have them help troubleshoot if necessary.

Litigators are usually fighting with people all day, every day. Over time, that becomes taxing. Whereas in in-house positions, there may be some litigation but if you're working on contracts - which I particularly love - both sides are trying to get to a mutually beneficial deal. That's a much more interesting, fun, and productive way of spending your day.

This is also perhaps why no in-house opening lasts for a very long time. There are always multiple applicants and people are willing to make that shift from a law firm into an in-house environment.

Lastly, corporate legal teams generally have more consistent schedules. You don't typically have to deal with scheduling problems, permanent overtime, or working all weekend. That might be required in special cases, but it isn’t the norm.

What do you think are the biggest problems faced by a GC?

The biggest problems you have as a general counsel are - a lack of budget and a lack of resources to do all the things that need to be done. And that is because legal teams are considered cost centers. Therefore, you need to prioritize your work and often resort to finding creative solutions to get your work done.

You also have to figure a way to leverage technology to build efficiency in your operations. To that end, you need to have discussions with the CEO or the CFO about the resource requirements and build a case for those resources to be allocated to you to help you do your work.

I've always thought of the legal department as having two goals - you're there to enhance value creation, and you're there to minimize value destruction. Everything you do, you can put into one of those two buckets.

It is important for a GC to either - demonstrate the return on investment of more resources or technology when you are looking to create value, or how it will fill gaps and prevent problems when you are looking to minimize value destruction.

It is vital for a GC to position and exhibit the team's work in terms of value or ROI. It is the language that your non-legal peers are used to. Effective business-friendly communication is an indispensable skill for a GC so that the business appreciates your team's work.

That usually comes down to numbers, charts, and graphs. You have to learn to speak their language.

The second biggest challenge - one that often goes undermined - is keeping your team happy.

Of course, there are times when you might have to ask your team to work extra hours, and they will understand that. But if they're required to do that every day and every weekend, you're going to lose them.

So as a general counsel, it is important to understand - how to balance out the work, make sure that the team feels appreciated by the business, and is paid appropriately.

Also, legal teams are now more frequently dispersed across the globe. It is the onus of a GC to bring everyone together, so they feel like a part of the team.

Speaking of keeping teams happy, offices are bound to reopen after a long hiatus. What administrative challenges do you foresee ‘returning to the office’ bringing?

Number one is probably the fact that people are going to expect some ability to work remotely at least part of the time. People may have acclimatized themselves to working virtually. If you suddenly insist that everybody be in the office every day just like they used to be, you're probably gonna see a lot of unhappy faces.

You need to strike the right balance and continue to provide that flexibility within reason, in a way that works for the department.

In one of my previous jobs as a GC, teams other than legal had the option to work from home. This felt unfair to my team and we eventually shifted to a new way to work.

Under the new system, everybody could work from home a couple of days a week on rotating shifts – but each group had to have one person physically in the office. On our meeting day - which was Thursdays - everyone needed to be in the office. This system worked really well and helped keep everyone's morale high. This ability to be flexible and accommodate others' interests should be a priority now.

The second challenge is to set up the lines of communication that will directly impact the productivity and daily work of your team. 

Your team is not only more comfortable in using technology than before, but they are also actively expecting to integrate it into their everyday experience. You have to account for this and maintain efficient avenues for your team to seamlessly talk, share documents, and collaborate through an easy-to-use interface.

There is a whole new market for Microsoft Teams, Slack, or any collaboration tool. Businesses have realized that legal teams have the same needs as any other team and are including them in technology conversations. Conversely, for sellers of technology, this means an opportunity to make inroads to a previously unexplored group of professionals.

Legal teams should also be looking around and asking their peers like marketing and the CTO office what they’re using, to see if they can leverage that technology to make their lives easier as well.

Can we adapt those tools to what we do in the legal department? Absolutely. There are absolutely zero barriers to using what other parts of the company are using. It doesn't have to be labeled as a legal tool, it could be anything.

Considering such a rapidly changing technology and legal landscape, what would you advise law students who will soon be foraying into the professional domain?

Beyond reading more and acclimatizing yourself with technology, I would say - be comfortable with numbers and have some basic finance skills. You don't have to be an MBA, but just making sure you can do the basics, a balance sheet, cash flow statement, and P&L, can go a long way.

You also want to start thinking about artificial intelligence and its implications on the industry. You have to get comfortable with using it to make your work life easier and be more productive.

But most importantly - and I tell this to my daughters, one of whom is in law school - don't lose your curiosity. It is what separates a great lawyer from a good one. There's so much going on around you if you just open your eyes and pay attention!

Use that curiosity. Go beyond your KPIs and read the company’s annual reports and hunt for information. Ask people that you work with from the business side about what they do and how they got there. I've always found that to be incredibly informative and interesting.

Ask them what their challenges are, what makes them tick, and how they solve their everyday problems.

When you ask someone questions about their work and the solutions they bring to the table, they will almost always be generous with their time. They can provide new insights and solutions. Please take advantage of it. People are dying to tell you what they do and how they do it. It is a great way to build genuine connections.

In turn, people are going to like working with you and will treat you better. This mutual respect will ensure that both parties try to always find a way to be flexible for each other and cognizant of each others' challenges.

Keeping that curiosity, both for your work, what's going on around you, and the people you work with will reap huge dividends down the road.

You just have to keep your eyes open, be curious, and then ask some questions.

Lastly, if you could go back in time to when you graduated, what would be that one piece of advice you’d give yourself?

I have had a very fulfilling career, and there is not much I would do differently.

The only piece of advice I would give myself is - there will always be enough work to engage with, but you don't have to be married to your work. If you try to work all the time, you'll eventually burn yourself out.

Your number one priority should be - trying to find the right balance between work and your family.