Office Hours: 3 GC's Answer Your Burning Questions Sterling Miller And Deborah Solmor (E68)

In this #OfficeHours episode, 3x general counsel and author Sterling Miller joins Deborah Solmor, 3x General Counsel and Founder of Ready Set GC to answer listener questions about life in #TheLegalDepartment.

Topics include: the transition from Deputy GC to General Counsel, how to advocate for budget and headcount, how to set goals, how to get board experience when you’re not the GC. Deborah and Sterling also tackle a sticky political issue in the c-suite.

If you have an Office Hours question, please contact The Legal Department at hello@legaldepartmentpod.com

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Listen to the podcast here

About Deborah Solmor

Deborah Solmor, the visionary founder of Ready Set GC, has redefined the narrative of empowering women in the foundational years of their General Counsel role. Motivated by her firsthand experiences navigating challenges and identifying gaps in support, Deborah stands as a trailblazer dedicated to reshaping opportunities for women in pivotal positions. Currently serving as the General Counsel for WARF, the independent nonprofit technology transfer organization serving the University of Wisconsin–Madison, Deborah continues to demonstrate unparalleled legal and leadership skills.

About Sterling Miller

Sterling Miller is CEO and Senior Counsel of Hilgers Graben. He has enjoyed a wide and varied 30-year legal career. He is a three-time general counsel, having served in that role at Marketo, Inc., Sabre Corporation, and Travelocity.com where he managed international teams handling a myriad of complex legal issues including “bet-the-company” litigation, M&A, IPO, corporate secretarial, data privacy, government affairs, and commercial agreements.

Out of law school, he was an associate at Gallop, Johnson, and Neuman in St. Louis. He began his in-house career in 1994 at American Airlines. He led the legal team for Sabre Holdings’ successful IPO in April 2014. In January 2019, after leading the legal team that worked on the successful sale of Marketo to Adobe, he returned to the Dallas office of firm Hilgers Graben PLLC for a second stint as Senior Counsel, focusing on commercial matters, litigation, and data privacy. He has published six books.

Sterling earned his J.D. degree from Washington University in St. Louis (Order of the Coif/Law Review) and his bachelor’s degree from Nebraska Wesleyan University, where he was student body president among other honors. He is certified in data privacy/security by the International Association of Privacy Professionals (CIPP/US). He is a highly sought-after speaker for legal department offsites and for legal and industry panels including presenting at the South-by-Southwest conference in Austin, TX and keynoting several ACC events. Under his leadership, Inside Counsel magazine named the Travelocity Legal Department one of the “Ten Most Innovative” legal departments in the United States (with the Sabre legal department later winning honorable mention under his tenure). He has been a multi-year finalist for the Dallas Business Journal’s “Best Corporate Counsel” award.

Sterling serves on the Board of Directors of Terrasoul Superfoods and the advisory boards of Travefy.com and Kyte. He publishes a widely-read and award-winning legal blog entitled “Ten Things You Need to Know as In-House Counsel.” The ABA published four of his books: “Ten Things You Need to Know as In-House Counsel: Practical Advice and Successful Strategies” in 2017, “Ten (More) Things You Need to Know as In-House Counsel: Practical Advice and Successful Strategies (Vol II)” in 2019, “Showing the Value of the Legal Department: More Than Just a Cost Center” in 2021, and “The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done” in 2024. His third book – a cookbook titled “The Slow-Cooker Savant” – came out in late 2018. Sterling’s first book, “The Evolution of Professional Football: 1920 – 2015”, was published by Mill City Press in 2015.

You can follow him on Twitter @10ThingsLegal and LinkedIn where he regularly shares his commentary and insights on cutting-edge legal issues.

Transcript

Welcome to Office Hours, a very different episode of The Legal Department. In this episode, I’m going to be joined by Sterling Miller who is the CEO of Hilbers Graben and also author of the in-house blog Ten Things You Should Know As In-House Counsel, and Deborah Solmor who is General Counsel of the Wisconsin Alumni Research Foundation and Founder of the Ready Set GC program. We’re going to be noodling your questions.

You’ve reached out to me in various forums and I thought this would be a great opportunity to answer those questions in a way that benefits all of us. If you have any questions for me, please reach out to me at Hello@LegalDepartmentPod.com. Without further ado, here’s my conversation with Sterling and Deborah.

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Deputy GC Dilemma: Should I Go For GC Or Stay Put

Deborah, I’m going to start with you because you just did Ready Set GC program for deputies. Here’s the question. “I’m the deputy GC at a company that is going through a transition. It has given me an opportunity to think about my next step. I’m debating whether to look for another DGC role or to “go for it” and seek out a GC position. How do I know I’m ready and how should I approach this decision?”

Such a great question. I think before I dive into that, I’ll start with something we talked about at our Ready Set GC Aspiring GC program. It’s really starting with the why. Whoever you are, you should be starting with the why because this question has two components in my view. One is how do I go about finding my GC role, but also how do I know I’m ready? I think that’s really the step back and ask why do you want to be a GC and trying to figure out is it that you want the title? Is it that you want the job, do you want the roles and responsibilities?

If you’re well set in terms of knowing what does a GC do and how will it be different than your DGC job, then we can move on to answering the question. I definitely think that anybody who’s aspiring to that role really needs to step back and first ask that question of why, I’ll date myself and say, we get on the hamster and the habit trail wheel and it’s the next step on that in-house journey. First, trying to figure out I want this job, but why? I have got lots of thoughts about the question, but I’ll stop there and we can discuss those.

Sterling, thoughts?

That is a fantastic answer to a great question. It goes so far beyond just legal work. If you’re not ready to deal with the paperwork part or the people part or the managing the board and the C-suite part, it can be a real challenge. Understanding why do you want to do this? Having a real honest assessment of where am I with my skills Personally, I knew I wanted to be general counsel at some point. If there was an opportunity that I thought looked fun, I would apply for it, even though I knew in the back of my head I probably wasn’t ready.

I found that going through that process of interviewing, in a way, was a version of that assessment that you created, Deborah, because I would hear, “How about this?” I go, “No, I’m not ready for that.” Understanding what you’re ready for and what you want and then just being prepared for a much more difficult and challenging job is that mental part that has to be there before you go down that path.

We’ve talked about this on the show before, that it is a different job and I think that lawyers are achievers, you get really focused on the career progression but it is a different role. Deborah, I wonder if you could just be a little more granular about what is the GC role as compared to the DGC role.

With the caveat that different organizations, the GC does different things and the role will differ depending on what type of an organization you’re in, the size of the team that you have available. I’ll speak in generalizations, but I think one of the most important things that I found in my GC career, so to speak, is being a good lawyer is table stakes. Nobody’s evaluating you when you’re going through the interview process about whether you are a great lawyer.

If you’ve gotten that far, chances are you’ve got great critical thinking skills and you know how to do the legal work. I think as you transition to a GC role to a C-suite role, it’s your soft skills that become your superpower, which is how is it that you communicate with people? How do you instill confidence? How do you show up? How do you think past the legal issues?

I think soft skills and then the other thing is the job is about being a business enabler. It’s really about how to support your organization and how to drive their strategic initiatives forward. Every article that’s written about this, every podcast I listen to, every time I speak about it, I say these things and I think it starts to sound a little bit trite. Of course, it’s that. I’d love to hear Sterling’s thoughts on this. It really is about that. It is absolutely a different job. It’s using your legal skills and thinking about risk management in a very different way.

Soft skills, 1,000% correct, Debora. No one knows how good of a lawyer you are. They assume you’re a good one, but no one’s going to really focus on that was a great memo or that was a great ana legal analysis. They will focus on is Sterling easy to deal with? Is he curious? Is he hardworking? Can he communicate well and simplify things? That last one is probably one of the most important skills you can have.

What I found surprising when I first became general counsel is the lack of familiarity with legal issues among the other members of the C-suite. You think legal’s really important, everybody’s going to understand it and then you start talking about things like litigation, we have discovery and then their request for admissions. You realize if they haven’t said it themselves, they have no idea what you’re talking about.

You have to reorient yourself to understand that if I’m going to be explaining something complex and legal first, I have to make sure I can simplify it in a way that they understand it. Also, not just bring them a problem. I have to also bring the solution to whatever it is that I’m talking about. You don’t always have to do that when you’re lower in the legal organization. You can go to the GC or the DGC and say, “I have a problem, here’s what it is,” and you have a discussion and maybe the senior person is leading, “Here are some options.”

If you just go to the board meeting or the C-suite meeting and go, “Yeah, we have a problem,” and stop talking, that’s a bad time to be in that room because like, “Well, and?” You really have to think it through what your issue is, what you’re proposing.

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As you alluded to, on the critical thinking skills, Deborah, is also spotting things that are important. There’s so much that goes on in the room that doesn’t have anything to do with the legal issue, but they expect you to weigh in on it and you need to have a position and a take and the ability to weigh in on things that aren’t necessarily legal problem A or legal problem B. That was all a real surprise to me.

Yeah, Sterling, I think that was a really good illusion you made that there’s really not a buffer, like in the DGC role, there’s a buffer, which is the general counsel and you can nerd out and be lawyers and talk about all of the different aspects. When you’re in the room as GV, like you are the ambassador, you’re the legal representative and you need to communicate in a way that people understand you so you don’t get to nerd out.

I want to pivot to a related question, but first I want to remind the readers, if you do have questions, you can always reach out to me at Hello@LegalDepartmentPod.com. I love having these Office Hours conversations. I love to hear from you. The related question, because you mentioned the board and I think depending on the size of company, a DGC may or may not have boardroom experience.

Cracking The Code: Demystifying The Boardroom Experience

I do get folks that reach out to me about specifically boardroom stuff. Here’s a question from one audience member. “I’m interested in becoming a GC one day and I understand that board experience is a requirement. I’m somewhat early in my in-house career and don’t have exposure to the boardroom. How can I get this experience? Also, what takes place in the boardroom? It seems shrouded in mystery for those of us who haven’t been there yet.” Sterling, why don’t we just pick up with you and talk about what is the boardroom?

The mystical boardroom. It’s like any other meeting except the issues are, as you alluded to, very high level, very important really to the strategic direction of the company. Solving strategic problems. There are certainly set meetings that occur regularly. Compensation-type meetings, governance, whatever committees are set up. Those will usually meet before the regular board meeting. Those subcommittees then are going to report into the main committee what happened at those subcommittee meetings.

The regular board meeting has a pretty set agenda, depending on the company, that they follow. You go down, there are different people who are coming in and out of the meeting to give presentations, to be there for different conversations. If you are the general counsel, you are there for all of that. For the most part, maybe on occasion, they will go into what’s called executive session and that’s a very limited number of people, directors, maybe the CEO. If you’re the corporate secretary, sometimes that’s combined, sometimes that’s not.

You’re certainly there for virtually all of it because you’re taking minutes. What’s going on, what are the decisions that are being made by the board. It is intimidating the first time you go in because you don’t know really the personalities. You don’t even know where to sit. You’re waiting to see how this is going to play out.

I was fortunate. The first time I went to a board meeting, I was not the general counsel. I was taken to the meeting and the GC spent some time with me beforehand saying, “Here’s how you dress, here’s where you’ll sit. Here’s the layout of the room, here’s the order that things happen,” and spent some time with me just explaining all the logistics. I would say the easiest way to get the experience that the writer of that question was asking are two things.

One, if you can volunteer for a board like a charitable organization, those board meetings are similar. They’re not 100% the same, but the process is the same. Any type of experience you can get on being part of or serving on a board is fantastic. That will help you when you actually have the responsibility. The other way, the reason how did I get into the first board meeting without being general counsel is I was always volunteering for the administrative stuff. “Let me help you with the budget, let me help you with the department goals, let me help you with that stuff.”

It is crucial to eliminate the perception of the legal department as a cost center or a non-revenue-generating entity. We need to remove such phrases and language from our vocabulary. Share on X

Not necessarily realizing that was a path to the board, but it was because the board is interested in what is the legal department doing? What’s the legal department’s budget? If you’re the subject matter expert, you probably are going to get taken along to the meeting and that may be your very first experience sitting in the room with the GC then saying, “Sterling’s going to walk you through the goals of the legal department or the budget for the legal department,” whatever year it is. There are different ways to get there other than the shock of just being the general counsel and having it be your very first experience with the board. That would be tough. Hopefully, you’ve had an opportunity to do something board related before then.

Yeah. Great tips. Deborah, I especially want to talk to you about this because you just joined a new organization as the GC. Thankfully, you’ve had the board experience, but talk about that relationship with directors. The GC role can be uncomfortable because your boss is the CEO and the board directors are their boss and you have a relationship with both of those people. Talk about just the experience being the GC with the board.

I think, again, another really great question and before I jump into that, Sterling, those are great suggestions about how you get that experience. The first question to understand is what does the board do? What does the board’s role? Why do you have the board? For most organizations, and again, it’ll differ by organizations, the board of trustees, the board of directors, they’re there for oversight of the organization. They have the fiduciary responsibility to look and see what is the organization actually doing. A lot of these meetings that we have are really to update the board and let them know at a high level what’s going on. They’re not there to manage the day-to-day affairs of the organization. That’s really done by the leadership and the employees and people in management.

I think that’s first and foremost, if you really have no experience with the board, educate yourself on what does the board do. In every organization, there are certain things that will be the same, but depending on your organization, public, private, non-profit, for-profit things will be different. Also, I think getting yourself acclimated to the board before any of these wonderful opportunities that Sterling is talking about presents themselves.

Read your corporate governance documents, read your organization’s bylaws. If the committees have charters, read the charters. If someone will give you copies of the minutes, read the minutes. Even though you’re not in the room, it’ll give you a little bit of better understanding what does the board do, what do the committees do? Who’s on the committees? How do they operate? Here I can look and see what they did in the past.

That’s a really great way to get yourself some free, “I get to go in the boardroom learning,” but to your question, yes, it can often be very difficult because one of the things that always fascinates me about the board is we each have probably a single boss. The CEO, their boss is the board. It’s not like one person, it’s this organization. When you’re in front of the board, you are in front of, generally, your CEO’s collective boss.

To your point, Stacy, trying to thread that needle of making sure that you build relationships with your board of directors, which is hugely important for the GC. Also, understanding how you manage the relationship between the CEO and the board, your relationship with your CEO, that triangle. I think soft skills, good relationship skills, listening and understanding.

In my career, I’ve been very fortunate. I haven’t had many of those sticky situations where you might have to be threading that needle between giving advice to the board and giving advice to the GC, but I’ve had 1 or 2 of them. I think that’s really where having built good relationships will serve you well. Your role as the general counsel is to the organization. It is not to any one person. I think sometimes, that’s where the rubber hits the road and you think of yourself as reporting to the CEO, but your job is to manage the legal affairs of the corporation. I think that’s what you are getting at in the question. Sometimes that’s tricky.

For sure it can be tricky. I’ve personally had situations where board members will take me aside and ask me for an opinion about something the CEO did or about the CEO. That is awkward.

One piece of advice I would give is when you get to that position, having a conversation with your CEO about how he or she wants you to manage those relations. I’ve been in three different organizations and I would say had varying degrees of, ‘If you talk to a board member, CEO, I need to know don’t reach out to board members on your own and if you feel you need to let me know.”

I’ve also had the other side, which is it’s really a great thing for you to develop relationships with the directors. Talk to them, eat with them, go out with them, meet them, get to know them. I think knowing what your CEO’s expectations are, just generally, and the board chair, talking to the board chair about what the board chair’s expectations are and then trying to find a way, if they don’t align, to help them align.

That is great advice because it is always best to know what does the boss want you to do.

You mentioned being in a new role. I just had a situation where I wanted to communicate something to the board and I did ask my CEO, “Do you want to see a draft? Do you want me to communicate?” He said, “You don’t have to get permission from me for your communications to the board.”

Sterling, anything to add on there?

No, having those conversations absolutely critical because if you do it in a way that the CEO of the board doesn’t like, you’re going to hear about it. It’s far better to just have that chat. I have the same experience Deborah’s had. Whatever you think you need to do, just go do some, “I want to know everything, everything they say to you every time they communicate with you,” vice versa. How do you deal with that? It can be tricky.

Setting Meaningful Goals For A Legal Department

Knowing upfront is a good thing. I’m going to pivot a little bit and Deborah, this is building on your comment about being a business enabler. This audience member asks for help in setting goals for the legal department. They ask, “Our company requires all departments to set annual goals. They’re supposed to be aligned with the company’s goals. Since legal is a service provider, we don’t generate sales, for instance.”

“I’m struggling to identify goals for our department. This is one of those management expectations that I struggle with.” I got to say, I don’t disagree. This is one of those things where you’re like, “I’m just managing the legal work. I’m trying to limit risk or I’m trying to get our costs under control.” How do you recommend somebody tailor their goals to match the company?

I think this is something that many GCs struggle with and that this question, probably you’re going to have many readers go, “I can’t wait to hear what Deborah and Sterling say about that.” I’ll give the caveat that the first part of my answer is really an easier said than done. That said, I think it’s hugely important to stop thinking of the legal department as a cost center, to stop thinking of the legal department as non-revenue generating.

Eliminate those phrases and that language from your vocabulary when you’re talking to your CFO when you’re talking to your CEO. We all know that we do drive value and you can’t put a price or you can’t put a KPI on all the things that didn’t happen because of the great work you and your team did. The contracts that you negotiate that have great indemnity in it or termination clauses that let people out.

The way you manage litigation the way you oversee diligence on a deal. These are things that are really hard to put into KPIs. I think part of the answer to that question is messaging. You are the messenger. You are control of the narrative for your team. The more you can fit the legal department into just another department in the business, I think that’s really important.

If you walk around talking about your own department as a cost center, that’s really not a really great narrative. I think that that’s probably the first place I would start. As I said, easier said than done. Sterling, I’ll turn it over to you. We can start talking about how to set kpis, how to do a quarterly report, how to report out what your team is actually doing. I think first and foremost, it’s how you shape the narrative around what you believe your function in the organization to be.

Yeah, Sterling, let’s hear your take.

I’ve written several blogs on this topic, including one just on setting goals because I had the same experience the writer of the question had and I know both of you had is there’s this vague legal go set goals, but no one gives you any assistance, no one gives you any real detail. If they want smart goals, smart, measurable, it’s really hard to do that for the reasons that Deborah set out. A lot of the things you do are hard to measure, so you have to figure out what to do.

What I did is I got tired of the process and I realized that it was more of an exercise on the part of the business versus a command and control on the legal department. Once I figured that out, as Deborah said, I’m going to tell a story about the legal department and it’s going to be a great story about how awesome we are and all the great things that we’re doing. If there’s something specific that the company wants me to measure or report out on, I will do that. If you don’t tell me exactly what I have to do, then I get to pick the things that I’m going to talk about.

What I’ve had was every year we started with five main goals. We talked about people, what we’re going to do with our people, what we’re going to do about the budget, what we’re going to do about contracts. That’s really the one of the most important functions of a legal department. What about strategic transactions? Things that were really important to the future of the company and then how are we going to defend and protect the interests of the company. That’s really litigation or government affairs, compliance. If you have a framework like that and then you start to plug in the things that are going to go under that, the place you start is you go talk to the business.

What is important to you? What should we be focused on next year or this year or this quarter? Whatever timeframe you’re trying to measure or at least set out what you’re trying to do. It’s hard to do that in a vacuum because what may be important to you as lawyers may not be important to the business.

You need to have the things that are important to the business on your list. It can’t always be that because some of the things you do, the business just doesn’t care about. They have to be done. For the most part, have you spoken to the head of sales? Have you spoken to the CFO? Have you spoken to whatever the different groups are? What is it that you need from the legal department? Help us help you. Setting those out and then when you’re reporting on them, tell the story.

That’s a lawyer superpower, telling story. Tell a great story and you’re probably going to have a pretty good story to tell, which means you are more than a cost center, you’re delivering value. I used to see all those announcements go out about, “We got this deal,” whatever. They would congratulate all these people. They would never congratulate the legal department.

I would call the CEO or the corporate communications. I go, “Things got done unless legal was involved. Can we get just a bone here?” You have to be willing to blow your own horn in a good way, in a positive way, not a jerk way. You can’t let stuff like that slip by because people won’t know what the legal department’s doing unless you are your best advocate. I’m pretty sure Deborah’s going to say the same exact thing on that.

I think this is a great point and it really ties in both what you both are saying, which is to enable the business, you need to know what the business needs to do and wants to do. Building your goals backwards, Sterling, I thought that was a great suggestion to meet with all of your business colleagues and find out what’s on their goals. For our organization, every year we do top goals and I just figure out where are the ways that legal is going to contribute and then I go to those business unit units and find out like, “Is this something we can do together? Can we partner?”

Let me tell you, achieving goals helps drive incentive comp. Together we’re better. I do think that there is a little bit of overwhelm with like, “I’ve got to show some metric. We increased turnaround time or we’ve reduced costs,” or something that’s super measurable. I think those aren’t necessarily strategic goals. Those are just metrics that are measurable. Deborah, you look like you were going to say add something in there.

I was. You’re inside my head right now because I think Sterling’s explanation about ways to approach it is perfect. I would only add that as you’re meeting with people, you need to step back and, and have a perspective of what you think they want. Not necessarily that might not align with what you think. Exactly what you said, I think legal departments tend to focus on metrics because they think that’s what the business wants.

How many contracts did I review? How long did it take? It might turn out as long as you get the work done, nobody cares how many contracts your team reviewed or how long it took or how many changes you made. I think it’s really making sure that what you are telling the business aligns with the things the business wants to hear. Sterling, your suggestion about meeting with them and really understanding their goals, because I think sometimes, we have it these blinders on, like these are the way we can contribute KPIs. Your business may not care about those KPIs.

The other thing I was going to say is tooting your own horn and getting visibility. I think it’s also important to get visibility for your team if you have one. One thing I have learned in my GC role where I did supervise a larger team was that when I got there, I don’t really think the CEO had an understanding of what all those lawyers did.

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We had a lot of conversations at the beginning about the people on my team as I was trying to assess them. It dawned on me that he really didn’t know what they did all day long. Understandably, that makes it difficult to know should you have that many lawyers. How do you get more head count if they don’t know what the people are doing? When you’re tooting your own horn and your legal department’s horn, you are only a success because if you have a team, they are successful. Make sure you give them visibility into the organization.

Budgeting Challenges: Outside Counsel Costs & Headcount Approval

Thank you for the perfect segue into another question. I get a lot of outreach on budget setting. I can’t tell you, I get so many people that ask. I’ve been trying to figure out how to do an episode on that. If either of you have suggestions on guests or ways to cover this topic, let me know. There’s a specific question. “I need help setting regarding setting a budget. So much of our work is out of my control. How do I accurately estimate our outside counsel budget? Also, any tips for convincing the CFO for more headcount?” Sterling.

Lots in there. I actually wrote about this setting a budget. When I was general counsel at a company called Marketo, the first budget I had to write and I was just going through my normal process and I thought, “I could turn this into a blog.” What I would do is on a big whiteboard first, look at everything you’ve spent last year or the current year you’re in. You’re just figure out where’s the money going, to outside law firms, to vendors internally, whatever the case may be. You cannot set a budget unless you have some understanding of what you have spent historically. The more data you have, you can go back and get it. We’ll help you at least start to estimate what it’s going to take in the different parts, the different things that the legal department’s going to do.

Go talk to your team. If you have a team, hopefully, what do you see coming next year? What do you see coming in whatever period you’re trying to budget for. Odds are pretty good, even if you’re the best general counsel in the world, you’re still not going to know everything that’s going on that may be coming up in in the next few months.

It’s primarily about information gathering, looking at historical trends and then trying to say, “If I get exactly the same amount I had last year, how would I allocate it? If I could get 5% more, what would I do? If I get 5% less, what would I do? I’m going to go in with, “I want 5% more.” Always ask for more, even though in your heart you go, “I’m probably going to get flat or I may even get cut.” Don’t start there because you may go backwards even further. Put your number there.

Also, relationship building with the CFO.

The value that we added. Why we were spending what we were spending? Probably the best thing and then I’ll stop and I’ll turn this over to Deborah. We had a monthly meeting within the legal department where we went through all the legal spend. Why do we think we’re going to spend next month? We have all the paperwork, all the law firms, and we had our law firms estimate, “Why do you think you’re going to spend in the next 30 days, next 60 days?” We had some rough idea. I included the person from finance who was responsible for the legal budget in those meetings. I didn’t do that because I thought they were the coolest person in the world. We needed to have them. Sometimes, it turned out to be the case.

I wanted them to hear in real time what we were spending the money on and why. “Okay, this case, there’s only two firms in the United States who do this work. Unfortunately, that means the rates are unbelievably high, but there’s no one else who can do it. That’s why we got to hire these guys. Okay, finance person, did you understand that? That’s why we’re hiring this.” We have all this litigation or whatever the case might be because when the budget gets set, people in the room are generally the CFO, the CEO, and all the minions of the CFO.

If there’s no one in that room who’s advocating for the legal department, you’re not in a good spot that is. I wanted to have someone on the inside who was intimately familiar with how the legal department was thinking about the budget. When something would come up, “You can’t cut that. Legal needs that,” because they know and they understood and they appreciated being brought in. That was I think one of the coolest things that we ever did because we figured out have someone on the inside advocating for the legal department.

Masterclass. Deborah, anything to add on there? I’m going to start doing that, Sterling. That’s a great suggestion.

That is a really good suggestion. I think I’d add the person who asked the question is right. It’s really difficult. It’s hard. Pending litigation, you can work with your outside counsel to try to budget, but you get sued, you get sued and you can’t really predict for that. I guess the other thing I would suggest is make sure that you’re thinking ahead for what are some strategic projects you may want to do that you need to put in your budget, you have to think over the course of the year. For example, in one role that I was in, we hadn’t had our insurance coverage program looked at in a long time and I wanted to hire outside counsel to really go through all of our policies, do a review, help us where we could negotiate, try to negotiate more favorable terms.

Sometimes, silence is a superpower. Share on X

I had to get an idea of how much is that going to cost so I could put it as a line item in my budget. Really thinking about are there things that you want to do that may be out of the ordinary would be one thing. Another thing, if you’re a new GC and you’re going into an area where you haven’t been before, how do you think about having your outside counsel to lean on for help?

Maybe a general guidance fund where you can access those funds really for no particular reason other than, “I have a question and I really could use help.” Think about the categories in your budget. One of the nice things I think about the legal department is when you look at our budgets versus some of the operations budgets, there aren’t a whole lot of line items. It’s much easier to advocate for those line items you want because there are so few of them. If you have a team, getting your team involved and don’t sit in your GC space and not get help from the people on your team who can really help guide your budget.

The last thing I would say, and I think, Sterling, you alluded to this with your conversations with finance and with the CFO, is get your business partners. Find allies in the organization who support initiatives that you may be wanting to do. This is good for all of us. If it’s a marketing review. There are so many examples I can come up with, but don’t silo yourself and don’t be isolated. Go out because then, when you have to defend your budget, to your point, Sterling, you have other people in the organization.

Maybe the chief marketing officer, maybe doing an HR audit, chief HR officer who says, “Yeah, we really got to find space in the budget for that.” Maybe if you’re lucky, they’ll even agree to split it with you. I think it’s really finding allies in the organization. You should not be setting your budget in a vacuum great or siloed.

Navigating C-Suite Politics & CEO Relationships

Everyone knows my number one thing is build relationships. I think both of you, those are really great examples of how to incorporate colleagues in and outside of the legal department in that budget process. The last question’s a political one. This is such a sticky question. I reviewed it with a podcast guest, Tricia Timm, who is in episode 66. I think that there’s a number of different takes. As we round out this conversation, really hoping you guys can help this audience member figure out to how to navigate this sticky relationship.

“I’m new to my GC role and I’m still getting to know my colleagues in the C-suite. All are very nice and welcoming but I’m noticing that we all seem to have different relationships with the CEO. Our chief administrative officer in particular seems very close to the CEO. He also leads HR, so supports the CEO and management of the C-suite team, including me.”

“The chief administrative officer has made comments to me about my compensation or how I’ve “worked” the CEO, suggesting that I’m overcompensated, I suspect he may be undermining me with my boss. What can I do to address this situation and preserve my relationship with the CEO?” All right, what say you?

A couple of high-level things. Number one, this is where, we talked about earlier, your soft skills come in. This is not about legal guidance, this is not about risk management, this is about, Stacy, your favorite thing. This is about relationship building. First and foremost, and maybe this is like mom advice, is I would step back and really assess the situation. We all come to these situations with our own narratives. We all have our own insecurities. Really trying to figure out what is the basis of believing this? When you step back from it, does the data point in the direction that this is happening? Really make sure you understand the situation before you start acting on it. Also, what is your relationship with the CEO? If your belief is your relationship with the CEO is good, maybe you should be trusting that relationship.

You don’t know what the narrative is of the person that you think is undermining you or causing these problems. I would really step back and really assess the situation from a non-biased or looking down over yourself perspective. This question really goes to, one of the things I always say about being a GC, I use the pie chart analogy. I have this pie and there are these slices of the pie. On any given day the slices are likely the same, but how big the slice is changes. Lawyer, finance person, politician, diplomat, counselor, psychiatrist. I think this is one of those ones where you’re really leaning into how to be a diplomat, how to be a problem solver. I would start there by really assessing it.

I don’t mean to be punting on what you should actually do about it, but I do think really having a transparent conversation with your CAO, if you really think this is the case, really just having a conversation which is transparent and say, “I’m getting some vibes here,” or like, “I want to talk to you about an issue,” and see where it goes. Remaining productive and forward thinking, not defensive or accusatory and really just trying to lean into really good relationships skills.

Also make a plug for reading any of like super communicators, difficult conversations. These are great resources to try to help guide you and really get into what I was talking about earlier, which is making sure that you’re viewing the situation accurately. Whoever you are, I am not trying to undermine or minimize the story that you’re telling. However, before you act on it, let’s make sure you’ve done everything to assess the situation. I guess that’s where I would start.

All right, Sterling, now you’ve got to really solve the problem, not just assess, like Deborah says.

Three things. If I really felt this was what was going on, first, have the conversation with my boss, the CEO. You could play it two ways. “I want to be easy for you to give feedback to,” or, “If there’s issues that I need to address, overcome both on the what’s going on in legal or just interactions with people in the C-suite, if there’s an issue, I want you to let me know.” You’re giving that person, the CEO, an opportunity to tell you. You could even be more upfront about it as Deborah suggests and say, “I’m getting some bad vibrations here. I just want to make sure it’s nothing, but here’s what’s going on. Do I need to do anything? Do I need to be concerned?”

Can I ask you, are you saying to have that conversation with your boss, the CEO, not with your colleague?

I’m going to get to that. Am I being undermined? That’s where you will find out. If you’re really being undermined, I think you’re going to know it because you’ll be hearing things coming back from the CEO’s mouth that tells you someone is raising doubts about what’s going on in legal or my ability to run the legal department. With the CAO, though, can I win that person or can I set up some time and go, “How can I help you? What can we do in the legal department to help you meet your goals? We’re here to help. What can we do?” You’re trying to see if you can pull them over to your side. You may not be able to. Sometimes there are people you can’t win over. When you realize that, you just have to accept that that’s part of the real world.

If that person made a comment to me about being overcompensated, I would say, “That’s really interesting. Can I set up some time with you to talk about it? I don’t think that’s the case, but I’m happy to show you the data,” because you can get data to support just about any compensation place you want to be both good and bad. I would rather go in fully armed and go, “Here’s the data that I’m looking at and I’m right in the middle,” or I I’m actually on the low side.”

Why not go, “I think I should be getting more.” You don’t have to accept someone telling you that they think you’re overpaid. You can go argue the facts or whatever facts you can marshal. That’s a separate conversation than trying to win the person over. All those conversations, this is where your soft skills come in. You can’t go in like you’re fearful or you’re scared or being off-putting in any way. You have to really think about how do I want that conversation to unfold and how do I want to bring my soft skills to the table because it could go sideways on you if you approach it in the wrong way.

I’ll just say this is a really good, tough, real-world situation. The three of you, you, Sterling, Deborah and Tricia Montalvo Timm, my last guest, the same elements are there, which are make sure you’re not telling yourself a story, you’re dealing with the facts, that you’re direct and leaning on those relationships and then advocating for yourself.

The last thing I would just throw in there, if you don’t mind, is that’s great advice, Sterling. Sometimes, though, also silence is a superpower. Figuring out whether you need to raise the issue at all. We don’t really know the full details, but I think sometimes you have to assess, “Do I say anything at all?” Sometimes, silence is awesome.

That is a very valid option. Absolutely.

Thanks so much for being here, you guys. This was again my first full episode dedicated to audience questions. I want to, again, remind folks that they can reach out to me at Hello@LegalDepartmentPod.com. I think they should check out both of your resources. Sterling, your blog and your books are, I would say, the masterclass in in-house practice. Thank you so much. Deborah, your contribution to help women aspiring GCs and new GCs is really inspiring to me personally. Thank you both for being here.

My pleasure. Thank you for having us.

Office Hours: 3 GC’s Answer Your Burning Questions Sterling Miller And Deborah Solmor (E68)