If it seems like it has been a while since I wrote a “Ten Things” post,[1] that’s because it has been!  I have been out on the road for most of October and November speaking at conferences, off-sites, street corners, church pulpits, casinos, bus stations, or wherever they will have me.  One thing I enjoy about doing this (other than the glamor of flying)[2] is getting to meet so many in-house lawyers and talking about what is on their minds. And that is where the inspiration for today’s post comes from. While on the road, I heard from many people that one of the hardest parts of their job is “dealing” with business executives, from front-line managers all the way up to the C-Suite.  In particular, people asked me why it is such a chore to get executives to focus on legal issues or take legal issues as important problems to solve vs. something that the lawyers are “dealing with” down in the basement but somehow requires them to spend part of their limited time helping with: “Why can’t you just make it go away and stop bothering me?”  I get it.  I had similar problems when I was starting out as an in-house lawyer and when I was general counsel, i.e., it never changed. I just got better at dealing with it.  How?  Because I spent a lot of time thinking about the best way to make an impact with my business colleagues.  And, over time, I figured out a number of things I could do to solve what is, apparently, still a very common problem even here in 2025. 

It will come as no surprise that it starts with understanding that working with business executives as an in-house lawyer is different than working with them as outside counsel. And, for those who arrive at the in-house world from a law firm, understanding that you are not the center of the universe.  If you are lucky, you may be the demi-planet Pluto or a large asteroid.  For many, this is a shock to the system, and some never recover or adapt.  We call those people former in-house lawyers (or really bad ones).  Second, and even more importantly, being successful at it requires a change in tactics and expectations.  I have compared the process to visiting the island of the “Wild Things.”[3]  And like Max, you must prepare yourself for a wild rumpus!  So brace yourself as this edition of “Ten Things” discusses how to best deal with the Wild Things… uh, I mean business executives:      

1.  In-House is different.  One of the biggest mistakes in-house lawyers make is treating their internal clients like they are fellow lawyers or how they treated clients when they were outside counsel, and usually, had the buffer of in-house lawyers between them and the client to translate. The reality is that advising as an in-house lawyer is fundamentally different, in expectations, incentives, and manner of communication.  Why is that?  Because, in my experience, business executives:

• Have a low comfort level with legal issues and concepts.
• Frequently lack the context of why certain compliance or legal issues matter.
• Operate with urgency and generally prioritize speed.
• View risk-taking as part of the business model – zero risk is not the goal (in fact, it is counter-productive).
• Want solutions, not just a list of problems.
• Need practical answers or solutions that show you understand the business.
• Prefer simple and concise over the complicated and wordy.
• See legal advice as part of a business discussion, not as an edict from on high.

In short, executives just want your best answer – short, clear, and actionable.  This means your job is not merely to spot the legal issues and risks, but to help the business weigh them, contextualize them, and navigate them (and do so in a language they understand).  Specifically, what is your advice on what they (the business) should do, and why do you feel that way?  This is generally very different than operating as an outside lawyer, where you lay out the risks and let the client decide what they want to do.

2.  What does success look like?  The above make for a difficult row to hoe.  The most successful in-house lawyers do the following:

• Are integrated into the business (act like part of the team and marry legal skills with a deep understanding of the company’s goals, operations, culture, and risk tolerance).
• Enjoy being part of the decision-making process (they make or assist with judgment calls about acceptable risks and how best to support the company’s overall objectives because they understand the business and the risk tolerance levels of the company).
• Feel a sense of ownership over the outcomes of legal decisions (they know they are responsible for more than just providing legal advice).
• Translate complex legal issues into something the business can understand (they don’t talk and write like lawyers).
• Operate with a high tolerance for risk and uncertainty (embrace stepping into the grey with the business).
• Give advice and counsel and always give their recommendation on the best course of action).
• Give context and background to legal problems to help the business decide on the best course of action.
• Are hyper-focused on the practical (and the simplest solutions).
• Move fast when necessary and aren’t afraid of being wrong.
• Focus on what’s important (and ignore the rest) and relay the “bottom-line” to the business – including actionable steps the business can take now.
• Realize that the legal department doesn’t run the business.

None of this is easy or even natural to people trained in the law, where risk tends to be all bad and legal analysis requires days of painstaking research with the ultimate output being a lengthy memorandum with perfect “blue book” citations, footnotes, and plenty of Latin phrases.  But the sooner you start moving toward the list above and away from your law firm roots, the more successful you will be in-house.  In other words, you need to learn how to solve problems differently.

3.  Learn the business.  If you have been reading this blog or any of my ABA books,[4] you have heard this bit before: You cannot advise executives effectively unless you understand how the business works, i.e., its structure, its finances, its products/services, its strategy, its competitors, its vendors, and its pain points.  If you have not mastered this fundamental task, this is now number one on your list of goals for 2026.  Think of it like this, few if any in the business will have any idea about how good or bad of a lawyer you are.[5]  They assume you have the necessary legal skills or you would not be in the legal department.  What they will focus on is how well you understand the business and do your solutions and advice reflect that understanding.  If not, they will tend to dismiss you (or worse bypass you[6]).  So, it is critical that you spend time learning how everything works at your company.  This means understanding things like:

• How the company makes money
• Who the deciders are and how decisions get made.[7]
• How the budget gets made.
• What the sales cycle looks like.
• What keeps the executive team and key leaders in the business up at night.
• Why customers buy the company’s products or services.
• The company’s strategic plans (current year, three-year, and five-year).
• The marketplace in which the company operates (may be more than one).
• How to read a balance sheet, P&L, and cash flow statement.

This is how you earn credibility with business executives.  And, more importantly, it is how you earn their trust, i.e., if you don’t understand the business (beyond the corporate brochure version), you cannot give useful practical advice, contextualize risk, or influence decisions.  How you go about doing this is actually fairly simple.  Get a company organizational chart (company and employee).  Meet with business leaders and ask them what matters to them and how the legal department can help (or get out of the way).  Attend town hall meetings,[8] staff meetings, sales kick-off meetings, and any other operational or strategy-focused meeting you can get invited to (or crash).  Read strategy documents, business plans, public filings, analyst reports, industry reports, and check out the company’s website and YouTube channel.  You don’t have to do it all tomorrow, but start identifying what might be the best sources of information and start to work them into your routine.

4.  Get to the core of the problem.  Executives typically don’t present problems to the legal department fully formed. They often present fragments, symptoms, and opinions.  Part of your job is to figure out what the real issue is, what the facts are (vs. opinions), and the “root cause,” i.e., what the hell is really going on?  Only when you have teased out the real issue can you help solve the problem.  It may be easy or it may be really hard.  Regardless, I have found having a set of questions designed to help you dig in is a critical tool in your hands.  Here is the list I came up with a while back as an in-house lawyer:

It is not a perfect list but it does several things: a) it shows business executives that you’re thinking like they do (note that there in nothing “legal” on this list); b) it helps ensure that you identify the real problem you need to help solve (which speeds things up); and c) it helps you tailor your advice to what actually matters.  Business executives appreciate lawyers who get to the essence of a problem and not just the noise around it.

5.  Be practical.  If there is one complaint from business executives that frequently rings true to me, it is that the legal department does not always give practical advice.  By this I mean advice that solves the problem in the most straightforward manner and takes into account the realities of operating the business (e.g., costs, business strategy, business priorities, etc.).  The goal isn’t to win an academic debate; it’s to help the business achieve its goals.  Lawyers like to play chess with legal problems, but most of the time you only need to play checkers.  Keep it simple – play checkers when you can and chess only when you must.  In short, this means you are practical:

• With your advice – it works in the real world and is fine-tuned by your deep knowledge of the business
• With your assessment of risk – you know the company’s risk tolerance levels and, for example, you are not going on about a million-dollar fine when a fine in that amount has never been issued.  More on this below.
• With your work product – you are not giving the business a seven-page email when all they need is a phone call or a Slack message.
• With your time – you are focusing most of your day working on things that matter to the business (because you are in tune with the business or you simply asked for their priorities).

Executives respect practical advice because it creates action. It pushes things forward. And it demonstrates that you understand the operational realities they face.  Practical lawyers get invited into strategic discussions early.  Academic lawyers often get avoided because they make things too complicated and no one wants to deal with that bullshit.

6.  Embrace risk.  Business executives live in the grey – a netherworld of uncertainty and risk.  A place where the real Wild Things live and thrive (or perish). If you can’t operate there, you will struggle in your dealings with the business.  Why?  Because most lawyers come from a world where the safest answer is always to minimize or eliminate risk. That mentality simply doesn’t work in the real world of business. Taking risks (big and small) is just part of operating a company. Wearing your aversion to risk on your sleeve as an in-house lawyer can be fatal to your credibility and your ability to get things done.  As in-house counsel, your job is to embrace risk, not to eliminate it.  The latter simply isn’t possible in the real world. Business executives embrace lawyers who can articulate and balance risk rather than simply point out that things are “risky” and scurry off feeling they have done their job.  They haven’t.  The good news is that (as far as I know) there are only six things you can do when it comes to risk: a) ignore it; b) reduce it; c) avoid it; d) exploit it; e) embrace it; and f) transfer it.  To embrace the grey and figure out which of the six you think should apply, you need to know three things, i.e., (a) the company/business unit’s business goals and strategy; (b) the company/business unit’s risk tolerance; and (c) the right questions to ask the business.  As for the latter, here are the questions I always ask (in no particular order):

• What do you want to do and why do you want to do it?
• Who’s involved?  Who else needs to be involved to get the full perspective of the risk?
• What are the downsides (what are you most worried about)?
• What are the upsides (what are you most excited about)?
• What can we do to minimize the downsides and/or maximize the upside?
• How much risk are you comfortable with?
• What do you need from me to help answer this?
• What is the likelihood and impact of downside?
• What alternatives achieve similar outcomes with less downside risk?
• Where does this sit on the company/business unit’s risk-tolerance continuum?

There are certainly more/different questions you can ask, but having a repeatable starting list of questions is incredibly helpful.  If you haven’t done so already, create your own list tailored to the company/business unit you serve.

7.  Stop writing like a lawyer. There is an eye-opening MIT study from a few years back that gets to the root of the problem lawyers face when they write to the business in the manner they were trained in law school and at the law firm: no one can understand what the [!@#$] you are talking about:

“In a nutshell, they find that legal writing is different in several ways, and those differences lead to significantly lower rates of comprehension and recall when these texts are read and interpreted by the general public. Lawyers can be drawn to this style of writing based on a feeling that it conveys more accuracy and precision, or simply because it fits with the expectation to sound “legal.” But too often, the legal style fails at the most basic language function of reliably conveying meaning.”[9]

There is literally nothing in the passage above that is good news for in-house lawyers unless they learn to write like business people and not lawyers.  It starts with understanding that you are a business person with a law degree, write like it.  Next, keep in mind these fundamentals:

• Shorter is better – keep it simple.
• Write like you are speaking to the reader.
• Always consider the business context.
• Prioritize conveying information (not the legal details) – focus on the “so-what?”
• Solutions over risk!
• Answer upfront.
• Use bullet points (make it “skimmable”).
• No one needs case citations or footnotes.[10]

As for the first bullet, my rule of thumb is that if I cannot explain it simply, then I do not understand the problem well enough to advise on it.  Just in case you need a bit more on this, below is a chart I created to show the key differences between writing like a lawyer and writing like a business person:

8.  Talk to the business.  Complex issues don’t get resolved through long email chains – they get resolved through conversations.[11]  While email (or Slack/Teams chats) can be a useful tool, relying on it as the exclusive way to communicate with the business is a mistake.  Find time to talk with them directly, on the phone, over Teams video, over coffee, at a rodeo, or whenever/however. Business executives value clarity, brevity, and relationships. Voice or face-to-face conversations deliver all three.  Why?  Because talking directly to the business does several things:

• Builds rapport/relationships.
• Builds trust.
• Clarifies issues.
• Clears up misunderstandings quickly.
• Shows confidence.
• Allows you to ask deeper questions.
• Prevents escalation.
• Gets to solutions faster – reduces “friction.”

Sometimes email is all you will have to work with and that’s fine.  But getting away from long email back-and-forth communication as much as possible will serve you well in-house, i.e., knowing when email stops being productive and dialogue is required is a skill to hone. The sooner you develop this instinct, the more effective you will be.

9.  Master the soft skills.  As mentioned above, most of your business colleagues will have no idea how good (or bad) of a lawyer you are.  They will know how good of an in-house lawyer you are based on something other than your technical legal prowess – they will know based on the soft skills you project.  They do this because soft skills are easy for them to understand.  For in-house counsel, my list of soft skills to develop and hone is long, but here are just a few that really matter when it comes to dealing with business executives:

• Humility.
• Active listening
• Curiosity.
• Emotional intelligence (EQ).
• Self-awareness.
• Adaptability.
• Quick learner.
• Proactive.
• Grit.
• Communicate clearly.
• Decisiveness.
• Calm under pressure.
• Good judgment.
• Approachability.
• Self-starter.
• Problem solver.
• Respectful.
• Responsible (takes ownership and delivers as promised).
• Gets shit done.

The most important soft skill?  In my opinion (and other than getting shit done), it is having a positive attitude. There are many things you cannot control, but you can control how you show up at the office – excited and ready to go or wishing you were anywhere else.  In short, soft skills determine your influence far more than your legal acumen.[12]  If you want business executives to seek your counsel, they must trust not only your big legal brain—but your ability to maneuver and interact in the corporate environment.  Being a dickhead might work at the law firm, not so much with your business colleagues.

10.  Lead with “yes.”  No one likes being told “no” – business executives included.  Unfortunately, many lawyers, especially those new to in-house fall back on something that they learned at the law firm – just tell the client “no, that’s not possible” and move on.  It’s easy, cheap, and prevents anything bad from happening (including the law firm getting sued for malpractice).  Again, what works (or is encouraged at the law firm) is not what is needed in-house.  Successful in-house lawyers always try to lead with “yes” (no matter how bat shit crazy or stupid the idea may be).  Learning to lead with yes starts with recognizing that you are in place to serve the business.  This means working hard to not substitute your risk tolerance level for that of the business.  There are, of course, times when the answer must be no, but those are rare (i.e., it’s criminal, violates the law, violates company policies, causes you to violate the rules of professional responsibility, etc.).  Otherwise, as long as the right person, with the right level of authority, is deciding to take the risk after everything has been laid out for them, then your job is to fall in line and help the business execute the strategy as best you can.  In other words, it’s time to go out on a limb and step into the grey!  To be sure, by “leading with yes,” I do not mean that the first words out of your mouth must be “Absolutely, yes we can do that!”  Rather, I mean not shutting down the conversation immediately just because you think (or know) the idea is problematic.  For example, my favorite was this: “That’s interesting.  Let me think on that a bit and see how we can try to make that happen.”  I did not lead with no, and I (hopefully) bought myself a bit of time to think through it and see if there actually is a way to make it happen.

Leading with yes also builds on one of the soft skills I noted above – approachability. This means making business executives feel welcome to bring their ideas to you (no matter how crazy) and knowing that you will try to figure out a way to get it done.  This means:

• No eye-rolling
• No exasperated sighs
• No demeaning/sharp language
• Use proper (friendly) tone
• Show correct body language

Lastly, here are some other ways to say “no” without actually saying it:

• Reframe the conversation: Instead of saying, “No, we can’t do that,” say, “Here’s an alternative that could help us achieve the same goal with fewer headaches.”
• Offer conditional approval: “We can move forward with that, but we should add these contract terms to reduce potential liability.”
• Risk-based approach: “This approach carries a good level of legal risk, but if we implement some additional safeguards, I think we can minimize it. Are you comfortable with this level of risk?”
• Provide a range of options: “Option A is legally safer but may take longer. Option B involves more risk but could be faster. I like ‘A,’ but which approach do you prefer?”
• Use the “right” language: “It may be challenging to proceed with this under the proposed structure, but if we adjust ‘X’, I think we can move forward with fewer problems.”

The bottom line here is that you don’t need to be a punching bag and say “yes” to everything.  Rather, consistently lead with a “get to yes” attitude and a willingness to not simply shut things down without at least thinking through the possibilities.  That’s the difference between the Department of Yes and the Department of No.

*****

As you start to focus on goals for the department and yourself for next year, consider a review (and potential overall) of how you are dealing with business executives at the company.  There is always room for improvement.  Every executive I’ve ever worked with wants their lawyers to be two things: trusted advisors and pragmatic business partners.  This requires you to balance legal rigor with business practicality.  When you do this, you gain not only influence but impact, i.e., you become part of the strategic guts of the company, not just a checkpoint.  For many lawyers, especially those trained at large law firms, this can feel uncomfortable and even counterintuitive. But if you want to thrive as an in-house attorney, learning how to work effectively with business executives is not just helpful, it’s essential.

Sterling Miller

November 29, 2025

My new book (number seven), More Slow-Cooker Savant, comes out on December 16 and is available for pre-sale right now!  Just in time for the holidays!

The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done, is available for sale.  You can buy it here: Buy The Book!

My fifth book, Showing the Value of the Legal Department: More Than Just a Cost Center is available now, including as an eBook!  You can buy a copy HERE.

Two of my books, Ten Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies and Ten (More) Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies Volume 2, are also on sale at the ABA website (including as e-books).

I have published two other books: The Evolution of Professional Football, and The Slow-Cooker Savant.  My second cookbook, More Slow Cooker Savant, is at the publisher and should be available to buy in October or early November – just in time for the holidays!  I am also available for speaking engagements, webinars/CLEs, coaching, training, pet sitting, bartending, and consulting.

Connect with me on Twitter @10ThingsLegal and on LinkedIn where I post articles and stories of interest to in-house counsel frequently.  

“Ten Things” is not legal advice nor legal opinion and represents my views only.  It is intended to provide practical tips and references to the busy in-house practitioner and other readers.  If you have questions or comments, or ideas for a post, please contact me at sterling.miller@sbcglobal.net, or if you would like a CLE for your in-house legal team on this or any topic in the blog, contact me at smiller@hilgersgraben.com.

[1] The last one was my annual “Cool Tech for In-House Lawyers” post.

[2] Sarcasm alert!

[3] My favorite book as a child: Where the Wild Things Are by Maurice Sendak.  If you have never read it, do so now.  If you have a copy, read it again (and take notes)!

[4] If you haven’t read my ABA books, consider helping a guy out and buying a few (dozen).  It’s the holiday season and they make the perfect gift to yourself or every single person in the legal department.  You can find the links at the end of the blog.  Now back to learning the business…

[5] Which helped me a lot because I made Judge Wapner look like Chief Justice John Marshall.

[6] Being bypassed sucks for many reasons, starting with the fact that they problem you are dealing with today would have been much easier to solve if you had known about it six months ago.

[7] Hint: it is not like Schoolhouse Rock! and “I’m Just a Bill (on Capitol Hill).”  It is as messy and weird as you can imagine(and sometimes it is a contact sport) – just like how laws really get made in the USA.

[8] And pay attention when attending town hall meetings – they are throwing out gold nuggets of information (you can crush candy on your phone later).

[9] Dr. Ken Broda-Bahm, “Limit the Legalese, and ‘Legalese’ Isn’t Just Jargon” (accessed November 27, 2025).

[10] If you are an in-house lawyer and you own and use the “Blue Book” you are in trouble.  Throw it in the trash right now, set it on fire, and bury the ashes with garlic and a crucifix so this evil never walks the earth again!  And if you are asking why you are reading this in a footnote, I simply say, “Pay no attention to that man behind the curtain!”

[11] I call this email tennis, i.e., you are just batting something back and forth between you and never really getting anything done.

[12] See “10 Essential Skills Every Attorney Should Know in 2025” (accessed November 29, 2025).