The Evolving Lawyer: Sterling Miller On Lessons From The Game Of Life

 

Sterling Miller has spent decades turning real-world experience into wisdom that every lawyer can use. From his early lessons in Nebraska to leading major legal teams and mastering AI for lawyers, Sterling’s journey shows how curiosity and courage shape lasting success. In this conversation with Joseph Schohl, he reflects on the pivotal moments that defined his career—from learning to follow his own instincts to saying yes when others said no—and how his love of writing, teaching, and sharing continues to impact the legal world. Whether he’s breaking down complex ideas, mentoring the next generation, or exploring new technology, Sterling reminds us that growth begins when we decide to keep learning, no matter where we are in the game of life.

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The Evolving Lawyer: Sterling Miller On Lessons From The Game Of Life

My guest isSterling Miller. You’re going to love this one. Sterling is a true renaissance man. We talk about his GC path, his books, his blog, the latest developments in AI for lawyers. This one has a lot. Stay with me to the end and I’ll share my biggest takeaways. Here’s Sterling’s a very brief bio. Sterling Miller is a 7-time author, 4-time General Counsel and Writer of the Ten Things You Need to Know About as an In-House Counsel blog.

He has been practicing law for over 30 years and has seen the evolution of the in-house lawyer role from a lonely backwater to strategic C-suite partner. Sterling is a sought-after speaker and GC Whisperer. I highly encourage you to check out his blog if you haven’t already seen it. It’s at TenThings.blog. All right, let’s get right into the interview.

 

 

All right, great. Welcome,Sterling.

I’m glad to be here. I’m excited talk GC.

From Poli Sci To Law: Sterling’s Unexpected Path

Absolutely. It’s great to see you. I want to talk about your origin story as and then work our way towards the many interesting things that you’ve been doing inside and outside the GC world. If we can go back in time, I’m fascinated to see that you would a Poli Sci degree with a minor in Mathematics. Tell me how those two go together, how they went together for you.

It’s a painful memory here dredging up. It’s interesting. I always wanted to be a lawyer since I was about eight years old. When I got through high school, the guidance counselor said, “What do you want to do? Are you going to go to college?” “Yes, I want to be a lawyer.” “Lawyers are a dime a dozen. You don’t want to be a lawyer. You want to be an electrical engineer.” Being an impressionable young man, first generation to go to college, certainly to go to anything beyond that, I said, “Okay, well I’m going to be an electrical engineer. What do you need to do to do that?” “You’ve got to take physics and math and chemistry, and all these science classes.”

Where was high school for you?

High school was in a small town in York, Nebraska, population about 6,000. Pretty small.

Where in Nebraska?

It’s in the Eastern part. About an hour West of Lincoln, Nebraska. It is about an hour West of Omaha. Hopefully they’ve heard of Omaha, at least, but it was a great place to grow up. I loved growing up in Nebraska. It was really great.

The Great Plains.

Yeah, the Great Plains, for sure. Very flat. I said, “Okay, great. I’m going to be an electrical engineer because why not?” I didn’t know better. I get to college and the fortunate part of this story is I went to a small liberal arts school called Nebraska Wesleyan University in Lincoln. I did not go to the big university. Of course, I started off in all the science classes, all the math classes, and I was okay at that, but I was in great. The bane of my existence was math and this was Advanced Calculus.

I took a lot of math because I had to but I was in the third semester of calculus which was just something called Differential Equations and that involves aquariums spinning and water coming in and out and you have to calculate all these things. This is really painful, but at the end of the first week of that semester, must have been sophomore year, the teacher got up with a piece of chalk on a chalkboard because that’s how old I am and wrote 96 and 12. She said, “This is the range of scores on the first exam.”

I was sitting there. I looked back at my buddy behind me and I said, “If you got a twelve, you should just pack your stuff and leave because you’re never going to make it.” She hands out the papers, I opened it up, there’s the twelve and I literally put everything in my little backpack and I walked out. I went down to the registrar’s office and I said, “I don’t want to be an engineer. I want to be a lawyer. Can you help me do that?”

They were so great. Absolutely. We changed all my classes over to things like political science and history and that’s how I became a Poli Sci major. “What do you want to do?” “I want to go to law school.” At that time, they were like, “Poli Sci is the major that you want to take,” which I regretted when I actually got to law school and realized it didn’t matter what your undergraduate degree was. There were people who were Music majors and Theater majors and everything else. I could have done anything else.

I had so much math credit that I had a minor in Math by default and a major in Political Science, but it just goes to show, follow your heart, what do you really want to do with your life and don’t let other people pigeonhole you or tell you what you should do. You should figure that out for yourself and it’ll be a better decision by far.

Follow your heart. What do you really want to do with your life? Don't let others pigeonhole you or tell you what you should do; figure that out for yourself. Share on X

It sure does. Thanks for sharing that. I had no idea when I stumbled upon that interesting thing on your resume that it would lead to such a profound story.

The Game Of Life: How A Board Game Sparked A Legal Career

My daughters love that story because, first, it shows that their dads are more on and then, secondly, it underscores what we were trying to teach them, which is make up your own mind, do something that you want to do that you really love and things will be far better for you. Dual purpose.

You wanted to be a lawyer in early age. I don’t want to leave that on asked. What prompted that at eight years old?

The Milton Bradley Game of Life, which is still around, I think. I know I played it when our daughters were young. One of the cool things about the game is to drive a little car around the board and you can get different pieces of paper. Some are pieces of insurance. One piece of paper was stock. I was fascinated by this piece of paper called stock. What is it? I asked my dad, “How do you get stock?” He said, “I think you have to be a lawyer to work on stock.” He didn’t really know, of course, but that’s what triggered, “Lawyer, stock. That’s what I want to do.”

I can remember pretty shortly after that, my younger brother and I created a lemonade stand and we had a Big Chief tablet. You have to be old enough to remember Big Chief was a writing tablet and we drew in crayons Stock in the Miller lemonade stand. We sold them for $1 apiece to our friends, in the neighborhood, so we had capital to start the lemonade stand, which of course, it went bankrupt quickly because we drank literally all the inventory. It was a hard lesson for lots of people but I would pay that $1 back if someone had a copy of one of those stocks certificates still.

Yeah, there’s probably a recession or something available, if anybody’s reading.

I don’t know what the statute of limitations is on that. It could be longer than I think.

Sterling’s offering a recession. Lessons from The Game of Life. I’ve loved that game. When I’d be playing with my kids, I’m like, “The goal is to load up the car with bunch of kids. Have some that don’t even fit in the car.” They’re like, “No, dad. It’s about making the most money and having the profession” I’m like, “No.” Everybody finds the way. Okay, great. How did you find law school? I mean, how did you find it to show up there?

I turned left at Lincoln.

What was your experience, exactly? Did you enjoy it?

I loved law school. I had such a great time. For me, reading and writing are is natural as breathing air. To go to a school where 90% of your day is reading or writing was heaven for me. I did not particularly like, the Socratic method. I found that to be not conducive to how I like to think through things. I like to take my time.

Being put on the spot, obviously, you have to adapt to that over and I have over time, but at the time, I really didn’t appreciate that piece but I really enjoyed the intellectual challenge. I liked being surrounded by really smart motivated people. It was great. The professors were terrific. I really enjoyed the experience a lot. I don’t know if I’d go back but having done it was certainly enough.

From Litigation To In-House: American Airlines & The Single Client Focus

That led to your first job, which was in litigation.

That’s right. Actually, another lesson here. I wanted to be a corporate lawyer. Remember, I wanted to do stock. When I went to law school, I ignored all the litigation classes and I took everything that had to do with corporate. Corporate formation, contract drafting, any seminars I could take. Anything that touched on corporate, that’s what I wanted to do. I got a job at the time at one of the largest law firms in St. Louis but it was only about 80 lawyers. If you can think about that now, that would make them a boutique shop and I was in the corporate group and I really enjoyed it.

I was doing all the things that I wanted to do. We had this really small litigation group, maybe twelve lawyers, and they had a case that was fairly large for the firm. They needed bodies to do discovery. This is when you went to the warehouse or wherever and you looked through paper. There was no relativity. There were no scan. There was nothing like that. You went box by box, and you had Post-it notes and you flagged the documents that you wanted and they needed people to go do that.

“I’ll do it,” so I did that. While that task wasn’t particularly interesting, what was interesting to me were the discussions about the case and the strategy and how were we going to do X, Y, and Z. What did we need to do next? Before you know it, I went to the head of the firm and I said, “I think I would like to be in the litigation group versus the corporate group.”

Once again, I’ve been so fortunate throughout my life and my career, it wasn’t no. It wasn’t, “What are you thinking about?” It was, “Yes, we can figure out how to do that. Let’s figure out what it’s going to take.” After a year or so of corporate, I moved over to litigation which I took to like a fish out of water. I loved going to court. I had no fear of standing up in before the judge or for a jury. I got first chair. Jury trial experience. I was only five years out of law school. I really enjoyed it. That’s how I got to litigation.

How does that lead you to your first in-house opportunity?

Of course it goes completely the opposite direction later on. As an outside litigator, I worked a lot with in-house lawyers and I was always fascinated by this process. Pick up the phone, call them, “Here’s what we think you should do. Here’s why. What do you think?” We’d have this conversation and they would go, “Let me go run that by some people and I’ll come back to you and tell you what we want to do.”

I was interested in what happened when that person he or she went and talked to whomever and they came back with, “We agree. We disagree.” That really fascinated me along with how much better could you get at your job if you just had one client, if you could really focus on all your energy on that business? I thought that would be really cool.

The third thing was I got married and my wife, I met her in St. Louis, but she was from Dallas. After we got married, we said let’s move by one of the sets of grandparents. Dallas, York, Nebraska, opportunity on the scales. It felt like Dallas was going to be the right choice, and it was clearly was. I ended up in-house at American Airlines which was and is a terrific company. One of the most amazing collections of lawyers, I think, you could ever have assembled in one place, certainly for an in-house legal department. Incredibly talented people.

I was in the Litigation and Regulatory section. The regulatory stuff really became the hook because part of the business that we supported was this travel technology business, that was regulated by the Department of Transportation. All the contracts came to this group. Basically, anything to do with this business came to the Litigation and Regulatory group even though it wasn’t litigation. I got back into doing contracts again. “You know what? I really do like this.”

I’m still doing the litigation but I really focus more of my time on the corporate side. American spun that business out. I was there for a couple of years and they asked, “Do you want to stay here in American or do you want to go form the Sabre legal department?” I looked around. There’s a lot of talent here. It’s going to take me a while.

How big was the department of American Airlines?

Sixty-five lawyers, something like that. It was really big.

Who was GC during that time?

Anne McNamara was the general counsel and Bob Crandall was CEO, who is legendary CEO. I saw him in action any time and learned a lot, mostly to keep my mouth shut, unless you had something that you knew you needed to say. It was exactly right. Otherwise, you were taking your career in your hands if you were going to just try to wing it Bob or with Anne. Anne was great. Great teacher about being prepared. If you’re going to go meet with the business, the importance of being prepared.

As much as I loved all the people that I was with at American, the small group that we spun out there, about six of us that spun out, and we formed the legal department at Sabre. I got in on the ground floor, I was in charge of litigation and regulatory, but a lot of other stuff. One of the things I learned that would be helpful in in-house career is never say no. Never turned down a combat assignment. That was something I read in a book calledThe Right Stuff and that was just meaning, if someone asked you to do something, the answer should be yes and figure out how to do it later.

We decided. I had a small team and I said, “We’re going to be the garbage men of the legal department. If someone does not want something or something doesn’t have a home, we’re going to take it. We’re going to drive our truck around, put it in the back.” We had immigration, we had bankruptcy, we had sweepstakes, data privacy, anything that no one wanted, we took. I had a really wide experience of different things, which not only was great from a learning standpoint and also keeping the job interesting, but I got to meet so many people in the company.

People in the marketing department, people in different groups because they needed immigration support or whatever the case was and meeting those people and understanding their different parts of the business prepared me as much as anything for when the opportunity came to become general counsel because I knew so much about the business, far more than anyone else in the legal department and far more than anyone they could bring in from the outside all because I just said, “Yeah, we’ll do it. We’ll take it. We’ll figure it out.” You can, unless it’s ERISA Or tax. I think lawyers are capable of learning any area of the law pretty quickly because you’re just naturally adept at learning that stuff.

 

 

Climbing The GC Ladder: From Sabre To Travelocity

You moved over with the group of six, then what did that ascent to the GC world look like?

The first opportunity, the general counsel that came with us, the lawyer from American who became the general counsel, great guy. His name was Andy Steinberg. No longer with us, but what a great lawyer and a great boss. He left around 2000 and they said, “We’re looking for general counsel. If you’re interested internally, let us know. We’re also going to look externally.” I was pretty young then.

It’s refreshing being invited to throw your hat in the ring. I work with folks who would like to become GCs and they’re at companies and the GC job opens and they have to put their foot in the door and edged their way in, which is always like if they wanted you, you’re hiding in plain sight, and I’m always surprised more companies don’t invite that.

That person’s not ultimately going to get the job at that point just to have that conversation expose them to the board. Anyway, it’s an aside, but I love that they did that.

Yeah, because not only did you get the experience but it’s such a morale boost for the department as a whole that a lot of times, they just say, “I have been part of this. I’ve seen this. We’re just going to look outside. Don’t even bother.” That is a crusher for the people who have been there for a long time and really know the business, like, “No one here is good enough to even interview?” It’s terrible message to send.

I did get the opportunity. I didn’t get the job. The person who got the job was a lawyer at an outside law firm who was in-house at American and was the person who hired me on his litigation and regulatory team. He was the first person that was in charge of litigation and regulatory for American. One level below Anne McNamara, the general counsel. We laughed about that because that was just pretty funny that he was someone. I was bossing around the week before because he was doing litigation for the company. Now he was brought in as my boss and said, “All those crappy cases you gave me are now yours again.”

I think, “Okay, fine,” but I learned a lot by going through the interview process and what happened then was a couple of years later, Sabre owned Travelocity. Travelocity needed a general counsel and that was my first opportunity to be general counsel. “Would you like to go?” They had one, he had left. They needed someone to take over how to small team there. Of course I said, “Yes, I would love to do it on the condition that I would not have to report to the person that had hired me at American and was currently my boss. I wanted to report to the CEO.”

“I’m happy to report what’s going on but I don’t want you to be my boss. I wanted to be autonomous,” and they agreed to that. I reported to the CEO. That was another incredible experience. She really brought me into the C-suite in a way that I wasn’t expecting. I thought I would be over here as the lawyer, but her vision, which is something that was rare at the time, but I think you see now is really prevalent was the legal skills are just the ticket to come here and work.

“I want you to be a strategic advisor. I want you to be part of the executive team. I want to hear what you have to say,” which, of course, forces you to up your game yet another level because that’s very different than just spotting legal issues, and weighing in on the legal issues. That was great experience. My first general counsel role was that Travelocity. My claim to fame at Travelocity was when they were creating the Roman gnome commercials. The Little Gnome dude. They previewed that for the executive team and they went around the table. “What do you think of this?”

They got to me and I said, “This is the dumbest ad ever. People are going to hate it. It’s never going to go anywhere. I would not do this.” Of course, not only does it become to be one of the most popular commercials ever, it’s in the advertising Hall of Fame. It is why I’m not in marketing. I appreciated being asked, but anyway, not a shiny moment for me, I guess. I was like, 12 to 1. Everyone else loved it. I remember in business school in marketing class being repeatedly told, “You’re not the client. You’re not the target. Think like the target not like yourself evaluate it through your eyes.” They’re absolutely right. Another lesson learned.

I would have turned down the gnome as well. It was annoying.

I have some around the house here. I have to go have to go look.

Mastering Business Acumen: The Language Of Numbers For Lawyers

Coming into that job, what did you not know that you didn’t know and that you had to learn to be successful? How was it different from what you had done before?

Very first C-suite meeting all the executive team is there. The very first thing they do is they throw out the P&L for the company and then they do the balance sheet and then you do the cashflow statement and they’re talking all the EBITDA and the gross profit, net profit, cogs, all these different things. I had no idea what they were talking about. I had accounting back in college. I think I sat pretty much in the back and just got through it. I remember nothing and I went, “I’m going to have to learn math. I’m going to have to learn business math, not calculus.”

There were a couple of things I could have done. I’m sitting there thinking I can raise my hand and go, “What’s EBITDA? What’s this?” That just felt career limiting, my little Spidey sense was tingling. What I did was I had a notebook, which I still have somewhere in a box and I started writing, “Things Sterling doesn’t know.” Very long note. I started writing down any term, anything that I didn’t understand, and then I would go find whoever presented on it. I would say, “Would you please spend a few minutes with me and explain why is this important? Why does this matter? How does this work?”

I never had anyone say no. I think being humble enough to admit you don’t know everything and you’re going to go to whatever source you can to find the answer if its first year finance person or the CFO or whatever the case may be, A, is a great look for the legal department because they tend to have the opposite view of lawyers and B, I learned a lot because I was humble enough to say, “I don’t understand this. Can you explain this to me?”

Be humble enough to admit you don’t know everything, and be willing to go to whatever source you can to find the answer. Share on X

I also did a lot on YouTube and a lot of reading, but I taught myself basically how to read financial statements and how to understand all that, which was really important because that’s the language of the business. It’s numbers. If you don’t speak that language, you’re just a tourist. You’re just hanging out and maybe you get a little bit of it, maybe you don’t. If you really want to be at the table, if you really want to be impactful, not only do you have to have legal skills, but you have to understand the business and you have to be able to talk that number language.

All legal advising within a business organization is risk reward cost benefit. If you evaluate that from a financial perspective, which is how score is kept, it’s not very helpful. I love that because then, of course, when you’re talking about legal things, which it’s hard to believe but not everybody has the same background. They’re hearing what you’re saying in a clear way but they may not have the background understand it. Now you’ve opened the door to them coming to you outside the meeting and asking questions and not feeling like they’re going to look dumb.

Effective Communication: Bridging The Gap Between Legal And Business

Yes, it is an invitation. If I’m going to ask you, you are more than welcome to ask me and I’m happy to teach you and explain things. That’s another lesson I think in-house lawyers need to learn generally especially when you’re presenting to the business or talking to the business is, they don’t necessarily love legal issues and most of them spend as little time as they can dealing with them. You can’t walk in and assume they understand anything at the level close to what you do.

Even if you walk in and go, “The plaintiff and the defendant,” they may not raise their hand but they probably don’t know what you’re talking about. Who’s the plaintiff? Who’s the defendant? What does that mean? We’re in discovery. What’s discovery? You have to recalibrate to not be condescending or talking down to them but to understand one of the very first things you need to do is make sure you are presenting the information in a way that they can understand so they can do what they need to do which is make a decision, give you authority, whatever it is that you’re trying to get out of that interaction with the business, presenting it in a way that they understand it.

They’ll also appreciate it because they’ve dealt with lawyers who have talked to them as though they are fellow lawyers and they really don’t like it, but they rarely speak up and say anything about it. When you talk to them in their language, they will tell you, “That was a really excellent clear explanation of the problem. Thank you.” What they’re really saying is you didn’t talk like a lawyer and if you’re writing things for the business, if you’re using footnotes, secondary sources, talking about dicta, you’ve missed the boat so far, you are drowning in the sea by that point.

If you have a blue book, chuck it in the trash. We’re never going to use it. You need to understand these things and learn those things. I learned that the hard way. Meaning, I screwed it up and then I figured it out. “Why am I doing it this way? This is what they want. This is what they need,” and adapting to them versus trying to force the business to adapt to the lawyers, which is how outside lawyers are.

I was just going to go there. These are essential lessons for in-house lawyers. If you’re going to be successful in-house, you either figure this out or you’re going to need to figure it out. Outside lawyers, who are reading, and I know outside lawyers read this, this is 100% equally true. When you’ve been in-house and then you go back, like you are, advising companies from the outside, having had that perspective is so helpful because as an outside lawyer, you’ve made a conscious decision to do what maybe all the people around you aren’t doing. You’re going to be behind on that. There’s a huge opportunity for outside lawyers to have a competitive advantage by either having served in-house role or at least adopting the mindset of an in-house lawyer.

You’re seeing more in-house lawyers go back to law firms. I wouldn’t say it’s a tidal wave or tsunami, but more law firms are figuring out, “If I have someone on the team who’s been in-house, they can help me relate better to the client communicate in a way that maybe we haven’t been communicating with the client.”

Sure, I can take whatever, an in-house lawyer, whatever super complex stuff you give me. I can convert that into something the business can understand but I really appreciate if you’ve already done that and said earlier, “This is some really complex stuff. I’ve written this in a way that we can share with the business without you having to do a lot.” I love that.

I write this blog. One of the blogs I wrote a long time ago is what in-house lawyers really want from outside lawyers and listed those things. When it was me, yes, I appreciate your super smart. You went to Harvard, I get all that, but give me something that I don’t have to spend an hour fixing that I can use with the business. That is someone that I will keep going back to.

How does Travelocity end for you?

Horribly. No.

That’s still there.

One of the interesting things, just a quick aside, I talked about all the talent at the American Airlines legal department and particularly in the litigation regulatory section. The four biggest online travel agents, this would have been mid-2000s, 2006, ’07, something like that, Travelocity, Expedia, Orbitz and Priceline. The general counsel for Travelocity was me. For Expedia, it was someone who was in the legal department with me at American and same with Orbitz.

We were all in the litigation group together. We were laughing at the fact that it was like a staff meeting. We got together. We were doing some lobbying in Washington and we all got together. Just an amazing amount of talent and amazing coincidence. What happened with Travelocity, it was partially public, partially private, and Sabre was getting bought by private equity. This was around 2008.

The private equity guys, “If Sabre owns Travelocity, why do they have two legal departments?” Of course, it made a ton of sense. That’s exactly the right thing to look at. The general counsel at Sabre was going to retire once the transaction was completed. They said, “Sterling, would you like to be the general counsel for Sabre?” Now, I had been all over the company. I had so much knowledge about the company, I had met so many people, the board, all those opportunities that you get as a general counsel were really paying off. I said, “Yes. On one condition. We bring all Travelocity back under one legal department, and I get to manage it.”

At that point, it was global. I had lawyers in the US and Singapore, Mexico, France, London, several cities in the US. There’s one other place I’m leaving out. It was another uber talented group of people that I got to be responsible for. I went back, we went private, which was actually a relief after being public because being publicly traded, as you probably know, your readers know, there’s a lot of stuff you just have to do from announcing things, paying attention, all the whole cycle of earnings, releases and quarterlies, proxies. It’s a lot and you don’t really get to do a lot of lawyer stuff per se.

Anyway, so that was a nice respite for a while. I went back and I’m in charge of the same legal department. My first board meeting, fall of 2008. What had happened in the fall of 2008? That was the housing banking crisis where the markets just collapsed. My very first board meeting, we were talking about how many people we were going to have to let go, how we’re going to cut costs, which is not a pleasant thing to go through.

I’ve experienced that many times in my career now, the highs and the lows. I was in travel when 9/11 happened and it was a pretty shock to the system moment when you wonder how the company is going to survive. It’s amazing, the resilience of some of these entities, these companies, but you got through it. My first meeting was not a lot of fun and it wasn’t high five, “Welcome, Sterling.” It was, “Here’s what we’re going to do to get our costs in line with the new reality of the economy.” A real eye-opener.

Navigating Crisis: Antitrust Battles & Taking Sabre Public

You wind up in that job for many years.

Yeah, about 6 or 7 more years.

What are the highlights?

I can tell you the lowlights. It was a great experience. We came out of the 2008 recession. Over time, things got back to normal. Travel business was rolling again in 2010. We then got into these huge antitrust fights with American Airlines, our former owner. A lot of my friends, very unfun experience. We had cases in federal courts, state court. We had a DOJ investigation. I had another airline that sued us for Anti-Trust.

I have to tell you, I tried to avoid a couple of things in law school. One was Tax law and the other was Anti-Trust law and I had to learn both as part of being general counsel and Anti-Trust law was the least favorite because not only is it a complex and weird subject very counterintuitive in a lot of ways, but the risk is unbelievable because it’s trouble damages. They can prove $1 billion. Basically, they could destroy the company.

Yeah, it’s damages and the threat of prison, right? It doesn’t get anywhere serious than that.

We had a couple of years on believably hard litigation. Weekends, holidays, it didn’t really matter. We were just working because everything was on the line and you feel the pressure of 12,000 employees around the world. If we don’t win this case or resolve it in a way that works, you literally could see the company declaring bankruptcy. It just wipes everything out for everyone, including myself, but that didn’t happen. We got through that. That was actually on October 30th of 2012. We settled on that day.

It’s imprinted in you. That’s amazing.

We went from that into we think we’re going to take the company public. We had to reorganize, we sold off some bits and pieces. That was a lot more interesting and more fun, but it was a lot of work. We’re getting the company ready to go public and then we took a public in 2014. I was fortunate enough to go. I’ve been there twenty years. I’m going to take my IPO and go and I went. I retired.

The 10 Things Blog & Beyond: A Prolific Author’s Journey

Here comes a bunch of interesting stuff for you. You write a book. Is this when you launched the blog or had you already done that? Tell us about your blog.

I had not. Very last day at Sabre, 2014, I had committed to doing CLE in Downtown Dallas, part of a whole day thing. I’ll still do that even though I wasn’t going to be the general counsel the next day. Afterwards, we’re doing at the cocktail hour, which all good CLEs have a cocktail hour, that’s the best part. These young in-house lawyers were coming up to me, and asking me, “If I wanted to be general counsel, what would you do with this, or how would you treat this?”

They were just asking me questions, which was fine, but they were writing it down on napkins and little scraps of paper and I thought, “If anyone’s going to write down what I experienced as an in-house lawyer, it should be me.” I had no idea how to write a blog and never thought about it in the past. I did some research and the very first one was November of 2014. I called it Ten Things You Need to Know as In-House Counsel because whenever we had an issue that was new or we didn’t really understand it I would grab whoever business people, legal people, whoever I thought I needed. “Get in this room and we’re going to whiteboard ten things we need to know about this. Go.”

It was a brainstorming tool, and we would just start writing down, “We need to know this. We’ve got to figure out this.” I just lifted that concept and I said, “If I had a legal issue, what are the ten things that I need to know about it in order to at least get my arms around it and start to be able to be effective,” and that’s it. I just pick a topic and I write, “Here are ten things you need to know,” and it was that simple. I thought I might do it for a year. My mom might read it. I never imagined I’d still be doing it. Close to 20,000 subscribers now.

If anybody’s reading who hasn’t checked that out, you’ve got to check it out. It’s such a great framework. Everybody loves a list of ten things.

It’s very practical because I’m writing it from being in the chair of the in-house lawyer, which is something that I think law firms miss when they write their client alerts. Either they’re written in a way that’s not very useful or they don’t give you the useful piece. I understand why they do that. They call us. If you’re at an outside counsel, you will get more calls if you actually give them something useful that they can look at and go, “This was really helpful. I’m going to call that person next time I have a problem,” then leading them all the way up to, “If you need this, call me.” They’re not going to do that. Some will, but most people won’t. I’m just throwing that out. That’s free advice for your outside lawyers.

Give them something useful. I love checklists, sample clauses. All that stuff is incredibly valuable to an in-house lawyer. They’re not going to use that as a substitute for outside counsel, I can tell you that, but if they find it useful, and they appreciate the fact that you gave it to them, they will come back to you. That I do know firsthand. That is certainly how it works.

I started doing that and then I was reading this book on the 1925 Pottsville Maroons, which were an NFL franchise in 1925. The book was about the controversy over the NFL title in 1925 where it was based on percentages. The teams could play whoever they wanted, high school teams, college teams, guys from the brewery. It didn’t really matter but all those games counted. They were all rigging the standings. It was really fascinating, but what really fascinated me, what happened to all these teams. The Dayton Triangles, the Portsmouth Spartans, all these, where did they go? I couldn’t find a book that just walked you through the evolution of the NFL.

I thought, “I’m sitting around. I’m not doing anything. I’ll just write one.” I didn’t know how to write a book. I just started going year by year. Here’s the NFL. I love the research. I got to live and breathe football, which I love. For me, it was a real joy. I found a publisher and that was the first book. The blog becomes so popular, the ABA reached out and said, “Would you like to do a book based on the blog?” That’s was the first book I did for the ABA. I’ve done four for them now, including the last one, which is on productivity.

The irony of writing a book on productivity is finding the time to do it. I used a lot of the things that I write about in the book and I write about it as an in-house lawyer. These are ways that you can get more out of your day without working longer. I screwed it up at first but I figured out over time, these are things that you can do that add up. Some add up really big. Some are only small, but if you add all those small things together, you can get a big chunk of time back. That’s what I wrote about that one.

The most popular book is the cookbook. I wrote a cookbook on using a slow cooker, a crock pot, maybe what people hear about. Far and away the most popular. Book number seven comes out. It’s a whole new cookbook on slow cooker recipes. That’ll be out in November and then I think I’ll go back to writing another one for the ABA after that.

The new slow cooker book, how is it different from the first one? Is it just additional recipes?

Additional recipes and the first one focused on a lot of really traditional things that you can make like a pot roast, beef stew, things that are really familiar. I thought what I would do is maybe make it a little more exotic. One of the things I realized about cuisine in the United States of the last 5 or 10 years is people like things spicier than they ever did and I think that’s a lot of influence of people either traveling or coming to the US, sampling cooking or bringing their cooking.

I have a lot of recipes from Brazil, from Portugal, from all around the world that I found that you can make in a slow cooker and just tastes awesome. They’re so easy. That is the thing I love about. It takes a little bit of prep time, but once you put it in and you turn it on, eight hours later, you come back and it’s just awesome. It’s a little more exotic. We’ll put it that way.

When do you write?

I will schedule time to write on my calendar. I’m a big believer and scheduling not just meetings with other people, but scheduling tasks or times on your actual calendar so it’s blocked out. I’m also a really early riser, so I can write in the morning, I can write late, I can write on airplanes, I can write waiting in the lounge for the airplane. Wherever it is, even if I only write for 15 minutes, that’s 15 minutes of the book done.

What are your tools for writing? Are you typing?

I use Word is primarily. I loved Word Perfect. I wish it was still around but I got over that.

You got your laptop?

I use a laptop. I also write on my phone occasionally. If I have an idea, I’ll just about something or write as much as I can if I’m just waiting for something and I’ll just email to myself and I can cut and paste it into the master document. Primarily, it’s a laptop and just finding time to sit. The only tool I use in addition to just writing is Grammarly. I find that to be really helpful in reviewing what I’ve written and spotting things.

If you write a lot, and I know lawyers definitely know this, you see words that aren’t there because you’re reading a line and you either have to step away or sometimes you just need a tool and I find Grammarly to be the best. It just goes and says, “You’re missing a word here.” How did I miss that? Other than that, it’s just doing some research and just sitting down and doing the hard task for most, but not necessarily for me because I love to write. It’s just to sit down and do it and just get going.

I talk about this in the productivity book. I learned this from one of the mentors when I was at that first law firm in St. Louis. Don’t try to come up with the perfect paragraph, the perfect topic sentence, just barf it up. Get it out, write it down. If you’re doing anything right, you’re going to go back and edit it. If you just sit there and try to come up with the perfect sentence, it just takes forever like, “I know I want to write about this.”

Don’t try to write the perfect paragraph or topic sentence—just get it out. If you’re doing anything right, you’ll go back and edit it anyway. Share on X

Sometimes, I’ll write about all the things I want to put into this paper or section or blog. What’s the easiest thing? I’ll start there. If I have ten things, what’s the easiest one? I’ll do that one. It gets you started and all those little things. I usually write the blog over the course of several days. I do 1, or 2 topics today, 2 or 3 tomorrow, mush them all together, edit it, all that stuff, but it’s rare that I would just sit down and write the entire blog. That would take a lot of time.

How often are you posting on the blog?

About once a month. It was every two weeks for the first few years and then I went back un-retired and went to the law firm and then I went back in-house and then we sold that company. I went back to the law firm. That was really the big decision point, stay in-house or go back to the law firm. I went back to the firm and now I’m the CEO. Your time gets harder, shorter and shorter. Once a month is good. That works pretty well.

First, I thought people were going to write me going, “How come you’re not writing twice a month?” They’re going to chastise me and I was feeling preemptively guilty for not publishing twice a month. Every once in a while, I’ll throw in one because I just have an idea and I’ll just do it and it’ll be. For the last couple of years, it’s been about once a month, though. I think it’s blog 190, this next one.

AI In Law: The Future Of Legal Practice

You’re literally the productivity expert. You’ve written the book on it for in-house lawyers. I want to talk about AI in the last couple of minutes we have here, but if anybody hasn’t listened To Stacy Bratcher’s interview of Stuart, go listen to it because what I want to do is I listen to that and this must have come out in late August 2025. I followed up on some of the ideas that you set forth in there, some of the products that you mentioned. I did a bunch of demos and have integrated into not only my daily practice, but that of my firm.

I’m leading this charge within the firm and on behalf of our clients and it’s hard to remember what it was like before. It’s that revolutionary, I think. I think of it as like it’s a 30-40-30 thing where it’s like the human is 30% up front, you turn it over the machine for 40% and then you got to finish it off. It’s great and way better than me in a lot of things, but GC AI, as great as it is, hasn’t actually been a GC.

You’ve got to still have that human element but together, you can create and do things that neither the machine or the human could do without. My question to you is, because things are moving fast, is there anything you would update from your talk with Stacy on things that you’ve learned or come across?

 

 

I would say the main theme of what I talked about with Stacy and they were right about this in the productivity book because that’s when I realized how powerful generative AI is as an assistant or tool for lawyers, especially in-house lawyers because we’re completely aligned with the time saving versus maybe the outside lawyers are having to get the money for their work when they’re using AI. Different thinking. Nothing wrong with that. That’s fine.

It’s the prompt. It’s the question that you asked and the follow-up that you do. That’s number one. That’s exactly what you were describing. Prepping the question, getting the answer and then taking that and honing it. What’s really exciting now is the agentic AI and those are tools that will complete tasks for you. It’s like If This Then That, which was an app that came out years ago. If this thing happens, it’s going to trigger another app. It’s going to do something. No, artificial intelligence, look at my calendar. If you see meetings for this, do the following or create an agenda, book dinner, whatever but it’s acting as an agent for you and doing things proactively. That is really exciting.

What was the word for that?

Agentic. They call it agentic.

Now the computer is having agency and being productive.

I told my daughters, both of them are gainfully employed now, one is a paralegal, one is a lawyer, “Be the person who understands how to use these AI tools.” I say that to any young lawyer, anyone from law school reading this, in-house, law firm, it doesn’t matter, because there are going to be plenty of old lawyers who all they’re going to want to do is find the person who knows how to do this. “Get me that person who knows how to write the prompt. Get me that person who can help me set up this agentic AI stuff.”

That will make you incredibly valuable to whatever organization you are in. If it’s an in-house legal department, if you’re the person who can help understand how prompts work, how to improve them, how to use AI, you are now what I was many years ago. I was a person raising my hand, “I’ll do the budget, I’ll help do the board slides.” I’ll do all those tasks because those were needed. This is what’s needed now, someone who understands that. I think that is the biggest change I’ve seen, how that’s going to permeate everything that we do. How can you use that to make the legal department or the law firm more productive and yourself more effective? That’s the next big one.

I 100% agree with all of that and I think the one of their thing that I know is implicit but I’m going to state it out loud for people, especially younger lawyers, is also to know its limitations. The ability to know how to use it and what its limitations are because I think there’s a risk. You or I, with all the experience we have, can tell when it’s not quite right or it’s missing something. I think by nature of our personalities, we’re always going to know that we don’t know everything. AI used the wrong way can make you think it knows everything when it doesn’t and I think that can get people in trouble.

That’s an excellent point. Not learning how to use it is a great corollary, understanding what its limits are. It’s not a substitute for you understanding the law. If you’re using it to write a brief, you need to read every case. If you’re not doing that and you’re turning that over to the partner, or worse, to a client or even worse, to a court, you are committing malpractice. It’s just a tool. You cannot do that.

It’d be the same if you have a really smart intern or a summer associate, you would never go, “Some associate wrote this. I’m just going to file it with the court as is.” You would never do that. Same thing. You can’t use it as a substitute for learning what’s going on. If I was using it maybe to draft a contract, I would still, as a young lawyer learning contracts, “What are indemnity provisions and how do they work? What are limitations of liability provisions and how do they work? When do I use examples?”

All those are things that you should be learning and asking questions about. Can you use AI to help? Maybe do a draft or maybe do things faster? Yes, but if you’re just going to sit back and push a button and expect it to do your job for you, A, they don’t need you because you’re adding zero value and B, it’s probably not going to be correct. It’s problematic.

Thanks for diving into that. I’m going to ask you one more question. We’ll leave it there. What are you personally most looking forward to?

I would say retirement but I retired twice so I don’t think that’s it. I think it has to be the AI. I am fascinated with how it works and the amazingly different types of outputs you can get from charts and graphs memos to emails translations. Where are we going to be in ten years? I don’t think we’re going to replace lawyers. I still don’t believe that. You’re not going to have a laptop in the boardroom and they’re all going to get a circle around it and ask it questions. They want that person there.

I think the lawyers who know how to use AI will always have a place. The lawyers who don’t, you’re the ones who are in trouble, or if you’re just doing something so rote that it can be written out. Where is that going to be in ten years from now? That’s probably when I’m done and I’m really not really going to worry about it as much but I will just be interested in how that plays out. I think that is the single most impactful change we’re going to see in the practice of law in probably the next 30 years. It was the computer the years ago and now it’s AI. We’ll see where it is in ten years and then beyond that, who knows what’s coming? I’m going to stick with AI.

The lawyers who know how to use AI will always have a place. The lawyers who don't are the ones in trouble. Share on X

We’ll leave it there and we’ll look forward to seeing what’s next for all of us. Thank you, Sterling. It’s been a real pleasure.

It’s been my pleasure. Thanks for having me on.

Take care.

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Key Takeaways: Never Say No, Keep Learning, Stay Cutting Edge

Thank you for reading. This episode was chock-full of lessons for inside and outside counsel. I’m just going to hit three main takeaways that I took for the interview with Sterling. Number one, never say no. Sterling became GC for the first time by being willing to do the work that others wanted to avoid. That helped leverage him into his first GC role. That role is leverage for everything that followed in his career.

Number two, keep a notebook for learning. He calls his Things Sterling Doesn’t Know, which is a great title. I call mine The Learning Notebook. When you stop learning, you stop growing and when you stop growing, your career begins to die. The discipline of keeping a notebook is something that many could benefit from and few people actually do. If something is newer interesting to you, you record it in the notebook and you’ve got a placeholder that you can then go back and review so that it begins to stick. Spaced repetition is what leads to learning having the notebook, is the antidote to things coming in and out of your brain without being retained.

Number three, stay on the cutting edge of your field. In this case, the most important thing happening in in-house lawyering is AI. Sterling is already established himself as a leader in the field and he’s leading, by example. He’s been a great example for me and my adoption of AI tools for myself and on behalf of my firm. Until next time. I’d love to connect with any in-house lawyers, or outside lawyers serving in-house lawyers, who are interested in maximizing their potential or learning new things. Please reach out to me onLinkedIn and let’s start a conversation.

 

 

Important Links

• Sterling Miller
• Ten Things You Need to Know About as an In-House Counsel
• The Right Stuff
• Joseph Schohl on LinkedIn

 

About Sterling Miller