Everyone likes to know the answer to questions that come their way at work, none more so than in-house lawyers.  Lawyers take special pride in being able to respond to practically any question, on any topic, at any time.  They can do this because they are, typically, very smart, well-read, and at ease with murky situations.  However, occasionally, and usually at the worst possible moment, someone in the business will ask an in-house lawyer a question and they will have no idea how to answer it.  This happened to me on more than one occasion and it was incredibly frustrating for me and whoever was asking the question – usually the CEO or a board member.  Why were they frustrated?  Well, because like most people on the business side they believe two things that make your job as in-house counsel even harder: 1) all lawyers know everything about all areas of the law regardless of their background or specialty, and 2) that there is a “Big Book of Law” we keep on a shelf that has all the answers to every legal question and all we lawyers have to do is take it down and find the right page.  Yeah, right…. So, what do you do when you get a question you don’t know the answer to (especially when they are looking right at you across the table)?  This edition of “Ten Things” set out some strategies to help you navigate this tricky situation:

1.  It happens to everyone.  I have been a lawyer for over thirty years and an in-house lawyer for most of that time.  I can tell you from personal experience that not knowing the answer to a question happens to everyone.  Without fail and without exception.  Including me.  So, if it does happen to you the first thing to keep in mind is that it is okay to not know everything; the world will not end.  No one, not even if you graduated number one in your class at Harvard Law School and clerked on the Supreme Court, can know all the answers to every question that comes their way throughout any legal career.  It’s just not possible.  The other piece of (good) news is that, with a few dickhead exceptions, no one expects you to have all the answers all of the time.  What they really want is to feel assured that you will get them the answer and get it to them quickly.

2.  Two scenarios.  There are two ways the “I don’t know the answer” problem can erupt.  The first is when the question comes to you via email, voicemail, Teams/Slack, or a similar manner.  When this happens, you usually have the luxury of responding that you’ll get back to them as soon as you can, and then go look for the answer – having a reasonable amount of time to do so.  Nothing unusual about this.  Happens every day.  All good.  For today’s post, we are going to focus on the second way this problem can surface, i.e., you are in a meeting (or receive a frantic call) and get asked a question you do not know the answer to – or you get called up to a meeting on a topic you only have a few minutes to prepare for.  While the second scenario is slightly better than the first (because you can do some very quick research before the meeting starts),[1] they both can be problematic if you do not handle them correctly.

3.  Be prepared.  Let’s start with the basics.  Whenever you are invited to attend a meeting, even a weekly status meeting of the executive team, spend some time in advance thinking about the types of questions you may be asked.  Such as, what’s been in the news?  What’s been going on at the company?  Any big or important developments in the legal department?  Why were/are you invited to the meeting in the first place?  If you are not sure about this last point, ask. Once you understand your role and the context of the meeting, you should be able to think about what questions might come your way.  Do the following:

  • Think about who will be at the meeting and any past experiences you have had in dealing with them, their perspectives, their questions, or their method of asking questions.  For example, if you know the company is discussing layoffs you can be pretty certain that questions about what the company is legally required to do in such situations will come up at an executive team meeting. Anticipate what you might be asked about, e.g., WARN, TUPE, disparate impact analysis, severance agreements, etc.  You don’t have to become an expert but having the basics down will serve you well.[2]
  • Time permitting, jot down a few anticipated questions and the answers.  It’s not perfect by any means – you can still get 100% surprised with a question out of left field, but the more prepared you are the better.  Or if the meeting topic is broad, e.g., insider trading, find a quick source of research that you can tap before you go to the meeting (ChatGPT, Practical Law, Google, etc.) and bring whatever you can as a “cheat sheet.”
  • If you are presenting at a meeting, then you know you will be on the spot and you must spend time anticipating the questions that may come up.  Ask a colleague to listen to your presentation and come up with as many questions as they can. This is great practice. Most importantly, avoid putting superfluous information into your presentation.  Any extra information can draw questions that divert from the real point and, perhaps, you have not thought about the topic sufficiently before blurting it out on slide six and then getting stumped on the first question (what we call an “unforced error”).  In other words, resist the urge to dazzle the attendees with your knowledge as it may come back to bite you with hard questions that you have not prepared for.  Bottom line, while you cannot anticipate everything, you can do some basic prep work to get yourself ready for questions that may come your way.

4.  Don’t multitask.  In my new book on productivity for in-house lawyers,[3] I talk a lot about multitasking, mostly in terms of how bad it is for getting things done. One way you will easily be caught off guard by a question is if you are attending a meeting and simultaneously checking your phone or email, trying to read a document, or otherwise not paying full attention to the discussion.  It’s hard to get away with this level of disinterest when you are physically in a meeting (though I see it all the time) and it more likely happens when you are attending via conference call or Zoom/Teams/Google Meet.  Usually, what happens is you are focused on an email or a text and the meeting discussion is a background murmur until you hear, “What do you think, Sterling?”  Shit.  That’s not a good thing to hear, especially if you haven’t been giving your full attention to the discussion.  No matter what question was asked, you will – at a minimum – ask them to repeat or rephrase the question (see below).  At worst, you will not know the context for the question and then you are really screwed.  You may even have to fess up to being distracted by something else – making a bad situation even worse.  Again, everyone has done this at one time or another (including yours truly) but resist the urge to multitask during meetings and calls (whether you are there in person or not) and you will be in much better shape when difficult questions come your way.

5.  Make sure you understand the question.  Another thing to do when you do not know the answer to a question is ask to have the question repeated, i.e., “I want to make sure I understand the question.  Can you ask it again?”  And then maybe ask a clarifying question or two. Not only will this buy you a little bit of time to let your mind start thinking about the answer, but the person posing the question may rephrase or clarify it in a way that makes more sense to you or that provides you with a way to answer, at least partially.  Of course, as noted above, if you have been zoning out or multitasking having the question repeated may buy you a little time but it’s unlikely to save your ass.  So, just so we’re clear on this key point: STOP MULTITASKING.  You suck at it.  We all do.

6.  Don’t Bluff.  When you don’t know the answer to a question, do not try to bluff your way through it and pretend like you know what you are talking about.  Lawyers love to do this because they think that if they can just keep talking long enough eventually they will stumble on something that makes sense. Wrong.  First, the “answer” is probably wrong (which can lead to numerous problems down the road). Second, it will be apparent to everyone that you do not know the answer and that you are digging a nice, deep hole for yourself.  Not a great image to project.  Third, you will irritate the crap out of everyone by pontificating on something you clearly don’t have a clue about, and everyone will hate you for dragging out the meeting.  Instead, if you do not know the answer to a question (and have tried the “ask it again” trick), simply acknowledge that fact and commit that you will get the answer as quickly as possible. Consider a response something like this:

That is a very interesting and challenging question.  I don’t have a good answer for it top of mind.  I’d like to spend a little bit of time researching it and thinking about it and then I’ll get back to you as soon as possible as the question deserves some considered thought.

That’s about as good as you can do with the situation.  However, if there are parts of the question you do know the answer to you can give a partial answer and note that you will need to do some further research on the rest.  For example:

I know that in most states what you are proposing is generally okay, though there are some data privacy concerns here as well.  There is usually a lot of nuance to work through depending on the exact facts.  I am not sure about how courts in [State X] see it and would like to spend some time digging into that and the privacy issues and come back to you with a more complete answer.

Again, this is about as much as you do so long as you stay in your lane with what you do know and lay out the need for further research.  As long as you have been paying attention during the meeting or were caught short with a phone call, most people will be satisfied with either answer above.[4]  I caution you that if you attend dozens of meetings and you frequently respond to questions with “I don’t know,” you may be in trouble and need to rethink your meeting attendance preparation strategy.

7.  Find the answer quickly.  If you have promised to get the answer and report back, you generally need to do so quickly.  You should have your best sources of information already in mind when you leave the room or drop off the call.  Here are your options:

The last bullet contains the best sources for quick, useful research because they are curated, kept up to date, and designed specifically for this exact situation, i.e., you need the answer fast and you need it in a form that is useful and practical, e.g., a checklist, a summary, a template, etc.  In particular, if you are asked to attend a meeting on short notice and you know what the issue or topic is, you can use these sources to quickly research the issue and likely have a basic understanding of the key points in 30 minutes or less.  I have also used ChatGPT to prepare a checklist of “what do I need to know to explain the insider trading laws to business executives.”  It works pretty well – the biggest problem being there is still a “can I trust this answer” problem.  As Westlaw and Lexis/Nexis (and others) have added AI functionality to their resources, you can get a “ChatGPT-like” response but feel better that the sources used to generate the checklist or whatever are up to date and topical for legal research vs. the dumpster fire that is the internet.

8.  Stay in your lane.  A corollary to “don’t bluff” is to stay in your lane, i.e., opine on what you know and don’t weigh into areas where you do not have the background or expertise to provide a good answer. Not only is this a smart way to work, but it also complies with your ethical obligations under most state rules of professional responsibility.  Under the ABA Model Rule, Section 1.1 all lawyers, including in-house counsel, have the following obligations:

1.1  A lawyer shall provide competent representation to a client. Competent representation requires the legal knowledge, skill, thoroughness and preparation reasonably necessary for the representation.

Comments 1 and 2 to Rule 1.1 illuminate how the rule impacts lawyers in light of our discussion today:

[1]  In determining whether a lawyer employs the requisite knowledge and skill in a particular matter, relevant factors include the relative complexity and specialized nature of the matter, the lawyer’s general experience, the lawyer’s training and experience in the field in question, the preparation and study the lawyer is able to give the matter and whether it is feasible to refer the matter to, or associate or consult with, a lawyer of established competence in the field in question. In many instances, the required proficiency is that of a general practitioner. Expertise in a particular field of law may be required in some circumstances.

[2]  A lawyer need not necessarily have special training or prior experience to handle legal problems of a type with which the lawyer is unfamiliar. A newly admitted lawyer can be as competent as a practitioner with long experience. Some important legal skills, such as the analysis of precedent, the evaluation of evidence and legal drafting, are required in all legal problems. Perhaps the most fundamental legal skill consists of determining what kind of legal problems a situation may involve, a skill that necessarily transcends any particular specialized knowledge. A lawyer can provide adequate representation in a wholly novel field through necessary study. Competent representation can also be provided through the association of a lawyer of established competence in the field in question.

As an in-house lawyer, you have some leeway to act as a generalist and apply your general legal knowledge and common sense to issues that you might not fully know the answer to.  Still, you must be able to recognize when something is seriously beyond your skill set and you either need to bring in someone else from the legal department or outside counsel.  No shame in either option.[5]  The response to a question like that is something like, “This is a pretty specialized area of the law.  I am going to need to connect with outside counsel to get the correct answer for you.  I will do that right away.”

9.  Follow-up as promised.  Most importantly, be sure you go find the answer (from whatever source) and follow up quickly – no one will forget that you promised to come back with the answer, so there is nowhere to hide.  Depending on your audience, e.g., the C-Suite is a higher priority than others, slot the follow-up work into your “urgent and important” matrix and get cracking.  As you put the answer together think about the likely follow-up questions.  Try to anticipate these in your response (versus waiting for someone to ask).  The business will notice and appreciate it.  Lastly, consider whether the legal department needs to add more expertise on the topic, i.e., is the question a harbinger for more legal questions to come on this topic?  If so, start to build out the right expertise or hire it if necessary.

10.  How do you get better?  It is unsettling to not know the answer to something (or be put on the spot when you are unprepared or caught off guard).  But it happens to all of us.  In most cases, you will have time to go find the answer but not always – sometimes an immediate answer is expected and this is where you do your best to prepare in advance.  Regardless, every failure no matter how small or big is an opportunity to learn and improve.  As a long-time manager, this was always more important to me than the fact that someone didn’t know something.  What I wanted to see was improvement, i.e., better preparation for “next time” or someone working to get smarter or learn more about a topic that was unfamiliar to them.  To me, curiosity is a critical skill for any in-house lawyer.  So, if you find yourself in an “I don’t know” situation use it as an opportunity to get better, to expand your expertise, or to find areas of the law for further development.


That’s all for this post.  I hope you don’t find yourself in an “I don’t know” situation but if you do (and you will), now you are armed with some ideas to help you make the best of a tough moment.  Even if the worst happens, you will survive it.  And if you are the boss and you ask a question of someone and they don’t know the answer, pick the right path as a leader.  Work with them to help them get better.  You may be frustrated but I promise you that if you have the right people working for you, you are not as frustrated as they are about coming up blank.  Give them the chance to prove it.

Sterling Miller

April 30, 2024

Book number six is in the hands of the ABA!  I am exchanging galley drafts and the cover is basically finished (hopefully I will be able to share it soon). The book is called The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done.  It will be available this summer.  So, stay tuned for more details!  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.

Cover of Value Book

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 on sale now at the ABA website (including as e-books).

I have published two other books: The Evolution of Professional Football, and The Slow-Cooker Savant.  I am also available for speaking engagements, webinars/CLEs, coaching, training, 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] If you get a phone call while at your desk you may be able to (if necessary) stall and do real-time research while taking the call, e.g., ChatGPT, Google, etc.  This is a skill to master.  ChatGPT is my new best friend when it comes to this tactic.

[2] Even if all of this technically belongs to the human resources department, understand that anything touching on legal issues will likely come to you in some way.  It’s not fair.  But it’s how it works.

[3] The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done, coming out this summer.

[4] Except for the handful of dickheads mentioned earlier.

[5]Now you can go claim some self-study ethics credit for your CLE reporting!