Ten Things: More Effective 1:1 Meetings (Manager View)

In my last post, I dealt with the importance and effectiveness of 1:1 meetings from the viewpoint of the employee.[1]  As promised, I will now discuss 1:1 meetings from the viewpoint of the manager. The first thing you should do is go back and re-read the last post because pretty much everything on that list applies to the manager side of the equation as well, either in terms of understanding where your employee is coming from or common sense tactics that make for better 1:1 meetings regardless of which side of the table you sit.  Second, if you have never had any training on how to conduct 1:1 employee meetings do not feel bad.  You are not alone!  Coming up through the ranks of in-house lawyers, my only experience with 1:1 meetings were the ones I attended as an employee.  Some managers were really good at it and some were pretty bad.  Since most companies don’t spend a lot of time training people (especially in-house lawyers) on how to manage people, when I became a manager and started holding my own 1:1 meetings the key, for me, was to mimic the things I thought prior managers did well and not do the things I thought sucked.  Over time, and with a little research on the side, I like to think I developed a process for pretty effective 1:1 meetings (though if you worked for me in the past you may disagree!). Regardless, since it is my blog, I get to at least pretend those 1:1’s were awesome.  And now it’s time to share that big bag of awesomeness with you. This edition of “Ten Things” shares my tips on how to host effective 1:1 meetings with your direct reports:

1.  Why it matters.  Last time, I described the 1:1 meeting as one of the most important meetings any in-house lawyer will have during the week. That is doubly true for you as a manager.  Near the top of the list of why it is so important are a) it is a terrific way to improve your relationships with your direct reports and b) it is a near real-time opportunity to deliver – and get – feedback (good or bad).  Just try and think of the number of times you’ve had a really important meeting in a group vs. 1:1.  Unless you are in the cast of the movie Cats and discussing your horrible career decision, the latter likely dominates.  A 1:1 meeting is also an easy and straightforward way to give and get information, which allows you to know what is going on with your team, how your employees are progressing (or not) against goals, and whether you need to reorder priorities or propose new ones.  Moreover, I have always believed in hiring smart people and then letting them go get things done.  Regular (and well-thought-out) 1:1 meetings allow you to set and reinforce expectations around projects, give high-level guidance, and strategize, all while continuing to allow your direct report to run with the matter at hand with the least amount of supervision possible – generally something both parties enjoy.

2.  Get the details right. The details of your 1:1 meeting matter.  By this I mean that they are set up at regular and appropriate intervals (e.g., every week or every other week), that you set aside sufficient time based on the needs and responsibilities of the particular individual (i.e., some 1:1 meetings can be 30 minutes, others need 60 minutes – just don’t make it cookie cutter). Eliminate distractions during the meeting by finding a quiet place to hold it (a small conference room is ideal) and by putting down your smartphone and turning off your computer screen so that you can give your undivided attention to the person you are meeting with.  Nothing is more demoralizing than talking to the top of someone’s head while they work on “more important matters” than their meeting with you.  While you may think of 1:1 meetings as a “time suck,” when employees know they have a regular meeting with you and that they will truly have your attention, they will be less likely to bother you during the course of the week with things that can otherwise wait for the 1:1.  These meetings also allow you to focus your team on the right priorities and keep them from running off on unproductive tangents.  Consequently, you will actually have more free time, not less.  Similarly, a well-functioning 1:1 meeting process will allow you, as a manager, to spot issues (legal or personnel) before they become bigger problems as well as energize your direct reports by showing you care about what they are working on, that you value what they are doing, and that you sincerely want to help them succeed.

3.  Mind your manners.  As a manager, I sometimes forgot the impact of what I said or did had on my team.  Anyone in a position of authority needs to understand the importance of “minding your manners” with your people, as everything you say or do reverberates down through them – for good or bad. If it comes from the boss, then it is extremely important and meaningful (even if you don’t intend it to be).  In the context of 1:1 meetings, this means some fairly basic rules:

  • Do not be late for the meeting (and if you are going to be late let them know as soon as you can).  If the meeting is important to you, it will be important to them.
  • Do not cancel the meeting unless absolutely necessary.  Yes, it can be a bit of a pain to host several 1:1 meetings every week but that is just part of being “the boss.”  Just not being “up for it” is no reason to cancel a 1:1. Think about the message canceling sends, i.e., “everything I am doing and on my calendar is more important than talking to you right now.”  If you must cancel the meeting, immediately look to reschedule – do not leave that up to your employee to do.
  • Have an agenda.  Do not show up to a 1:1 with “tell me what you’re working on” as your only topic.  Take the time to prepare and plan for each 1:1 (just like you would want your boss to plan for your 1:1 with them).  Ideally, if there is something important you want to discuss with them, let your direct report know about it a day or two in advance so they can properly prepare.  While an agenda is important, do not be overly rigid about it.  If something comes up during the meeting that requires more time and attention, make that the priority (vs. ticking off everything on your agenda). If necessary, set up a second meeting to focus on that priority issue so the 1-1 doesn’t become solely about one topic.
  • Start the meeting on a “positive.”  Unless you have the worst employees of all time, everyone has done something commendable since the last time you met.  Lead with that.
  • Take notes.  Nothing says “I could care less about what you’re telling me” than you not taking notes of the conversation.  At a minimum, it will help you retain and remember what was discussed.  It also provides a written record of the next steps, etc.
  • Make sure they know that the 1:1 meetings are never a bother and make them feel welcomed and that you enjoy the discussions.  Body language and non-verbal queues are everything here.

4.  Be a teacher.  Part of your job as a manager is to help groom the next generation of leaders of the company and the legal department.  A 1:1 meeting, therefore, is far more than just an “update session.”  It provides time for one of your most important duties – coaching and mentoring.  Hopefully, one of the reasons you became a manager is because you have an affinity for working with people and helping them grow and develop (at least the company sees you in that role).  If not, you may want to rethink being a manager.  For example, if someone brings you a problem, teach them to bring along a potential solution as well.  If someone is a poor writer, work with them on honing and improving that skill.[2]  If your direct report is not consistently demonstrating one of the company’s core values, work with them on how to do so.  A small dose of caring and encouragement goes a long way.  Look for opportunities to teach habits of success, i.e., the little things every successful in-house lawyer has mastered to advance their career.[3]  It can be as simple as getting work done on time or ensuring all the administrative tasks on your plate are completed without someone having to hound you.  It can be as complex as learning how to write and present succinctly, with a heavy leaning toward the practical.  To get where you are, you have obviously done something right.  Your 1:1 sessions are the chance to share your wealth of knowledge and experience with your team.

5.  Be constructive and precise.  The easiest task in the world is to tear something or someone down.  It takes little effort or thought, just the time to start “smashing” – like an uninformed, mean-spirited early morning Tweet.  When you smash, it should be no surprise that you end up with rubble.  At your 1:1 sessions always try to be constructive, even when you are having tough conversations or when improvement is clearly needed from your employee.  A cutting word from the boss can be as devastating as any workplace encounter can possibly be.  This means spending time properly prepare for each 1:1 and thinking about what you want to say and how you are going to say it.  One fact I always kept top of mind as a manager: it far more expensive and painful to replace an employee than it is to teach them how to do it right.  Unless they are “hopeless,” it is far better to teach than to blame.  It all starts with actively listening.[4]  The single most important thing a manager can do during a 1:1 is listening to what their employee is saying (along with focusing on body language and other subtle clues everyone gives off when they speak).   Additionally, when giving feedback be sure to be precise.  Use real and recent examples to make your point.  Some managers try to avoid difficult feedback by being vague and assuming their direct report “got the drift” of what they were trying to tell them.[5]  Wrong.  Most employees welcome feedback on how they are doing, even if it is about the need to improve.  And they would rather hear honest, specific, and real-time feedback vs. you saving up examples and then blindsiding them at review time when months of time to work on the feedback has passed.  Just keep in mind that the 1:1 session is not typically a career development session/employee review (i.e., those more in-depth discussions are saved for specific times of the year).  But, you should not wait to address performance issues generally and the 1:1 meeting is the right place to catch things early and before they become a bigger issue.

6.  Plow the road.  There is a classic episode of The Simpsons where Homer buys a snowplow and becomes “Mr. Plow,” the king of snow removal.  As a manager, I adopted the “Mr. Plow” persona, not for the purpose of picking up easy cash keeping driveways clear of snow and ice but rather as the person in the legal department responsible for clearing the way for my employees to be able to do their jobs.  Part of my job was to plow the road for them.  Consequently, at my 1:1 meetings, I would ask my team what I could do to help them and whether anything was getting in the way of their ability to get work done?  For example, someone may be inundated with requests to work on small value contracts while trying to block big chunks of time needed to work on a vastly larger deal of strategic importance to the company.  My job would be to find a way to keep them from being pestered with the lower value work either by reassigning it or talking with the business leader about the legal department’s need to focus on the bigger value project for the time being (and being the one to take the verbal “beating” that sometimes comes with such a conversation).  The 1:1 meeting is the perfect place to let your employee know that you have their back and that they should come to you whenever they are faced with a problem or obstacle and need some help figure out how to handle.

7.  Work on their soft skills.  As a manager, you know that there is more to being successful in the legal department than just being an excellent lawyer.  While the technical skills are certainly table stakes, every in-house lawyer needs to master the “soft skills” of operating in a business environment.  This area is one of the biggest differences between working at a law firm vs. working in-house.  At the former, if you are brilliant or a rainmaker, you can be an asshole and there are rarely consequences.  In-house is a different story.  Being brilliant is rarely enough to survive and/or advance.  You need to bring a host of soft skills to the table as well.  Here is just a partial listing of the soft skills every in-house learning needs to possess and constantly hone:

  • Executive presence.
  • Approachability.
  • Humility.
  • Active listening.
  • Time management.
  • Responsiveness.
  • Ownership of errors.
  • Urgency/”Hustle”
  • Risks (taking too many or not enough).
  • Communication (simplicity when writing, speaking, presenting).
  • Availability.
  • Empathy.
  • Confidence.
  • Persistence.
  • Patience.
  • Humor.
  • Dealing with office politics.

Of course, the list could go on but, as a manager, you should decide what soft skills are critical for success in your legal department/company and use the 1:1 meeting as an opportunity to point out when your direct has made or missed the mark, i.e., constantly coaching them up or reinforcing the right behaviors.  One thing I did for my directs every year was think of the one soft skill they needed most to work on and then give them a card with a word or two on it that they could keep on their desk to remind them to practice that skill, such as “Patience” or “Smile” or “Listen” or “Pause.”  The latter, for example, was for someone who needed to pause more frequently when talking or presenting to give the listener (sometimes me) a chance to ask questions or give additional information or context.  Finally, and since no one is perfect, a 1:1 is also a chance for you to work on your soft skills as well, i.e., listening, empathy, patience, etc.

8.  Get feedback about yourself and the department.  It is easy to think of a 1:1 meeting as primarily a one-way street in terms of information coming to you and feedback going to your employee.  If that is how your 1:1 meetings operate you are missing out on some valuable information – feedback on yourself and the department.  Here are some important things to ask during your 1:1 meetings:

  • What can I do to be a better manager?
  • What is the one thing I can do to make this a better place to work for you?
  • What is the one thing the company can do to make this a better place to work?
  • Is the legal department/this group focused on the right things? Where should we focus our time and energy?
  • What is the pulse of the legal department/this group? Are people happy, nervous, worried, excited? What should I be focusing on in terms of morale?

It may take them a few sessions to warm up to the idea of giving feedback to their boss, but once they know you are sincere (and that there are no repercussions for honest, constructive feedback), you will gain incredibly useful information that will make you a better manager and in-house lawyer.  You will also be creating an environment where your direct reports feel their input is valued and they will naturally get more comfortable with you, which will lead to better discussions and a better working relationship.  And during these crazy days of COVID-19, asking for such feedback can help mitigate the uneasiness your employees may be feeling.

9.  Expand the pie.  Generally, your 1:1 sessions are only with your direct reports.  Consider mixing things up on occasion and going down a level or two and scheduling 1:1 meetings with others on your team, i.e., those folks that report into your directs (or even lower).  Everyone likes to feel like they are noticed by and valued by the boss and being invited to come and have a 1:1 can be a great morale builder.  Just be careful to make sure when you invite them that it is clear that they are not in trouble in any way (as some will see a surprise invite to come and see the boss as something negative, especially amongst the lower ranks).  Keep the meeting short (20 – 30 minutes) and use it primarily to get to know them better, i.e., the agenda is not the same as you have for your direct reports.  One easy ice breaker is to ask them how they got to your team (what was their career path and why did they want to come work at the company).  Another is to ask them what types of projects they enjoy working on and whether there is anything you can do to make their jobs easier or more rewarding.  You’ll be surprised sometimes by how honest these folks will be – and how much great and useful information you will pick up.  If they have done some particularly good work or passed a significant milestone, it is a chance to recognize them for that.  And, of course, this is a chance to talk generally about your expectations for the team/department as a whole – when everyone knows your expectations the team/department will run better.

10.  End strong.  Oddly, many managers do not think about the “ending” of the 1:1 meeting.  For some, they simply say “Thanks” and then quickly get their nose back into their laptop or smartphone.  This is a mistake.  Like a gymnastics routine, the ending is the most important part!  As you wrap up be sure to assign any “go do’s” arising from your discussion (including any deadlines and expectations). Additionally, if there is anything you want to discuss “next time” be sure you lay that out so your employee knows to be prepared to discuss that project or issue at the next 1:1.  Likewise, are there any “go do’s” for yourself?  Make sure you note those.  It may be that you have some resources to share or you need to check on something and get back to your direct report.  Finally, be sure to tell them “thank you” and that you appreciate their efforts and the work they are doing.  Even if there are things they need to work on, ending the 1:1 by expressing gratitude for their efforts will keep them energized and focused on improving vs. dejected or feeling undervalued.


That’s it for my two-part series on 1:1 meetings.  I hope it has given you cause to re-energize and re-imagine your 1:1 meeting process and consider whether you (as manager or employee) are looking at it with the right mindset and if you need to up your game. It may be a good time to “reset” the process.  If you are looking for more, check out The Art of the One-on-One Meeting.  Also, you do not need to incorporate everything above into every 1:1 meeting. Just look for chances to make each meeting a little better and more useful.  But, if you view these meetings as a slog and something to “get it over with” as quickly as possible (and cancel frequently), then you’ll get back as much as you put into it – not a lot.  If you see them as the critically important part of your job that they are, building on and enhancing your process will make your job easier, your employees happier, and your legal department run more smoothly.

Stay well, my friends.  Wash your hands.  And please wear a mask.

Sterling Miller

June 30, 2020

Ten (More) Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies Volume 2 is out.  It’s my second book based on this blog series.  As the ABA says, “All in-house lawyers need to own this book!”  Click here to buy it.


I have three published three other books: Ten Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies, The Evolution of Professional Football, and The Slow-Cooker Savant.  I am also available for speaking engagements, CLEs, coaching, training, and consulting.

Connect with me on Twitter @10ThingsLegal and 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, please contact me at sterling.miller@sbcglobal.net.

[1] See Ten Things: More Effective 1:1 Meetings (Employee View).

[2] One of the most important things a manager ever did for me post law school was take a red pen to one of my first briefs and mark up my writing.  A lot.  Then they sat down with me and walked through the redline and their comments.  I learned more about legal writing in that 45-minute meeting than I did during my entire time in law school.  Thanks, Chip Seigel!

[3] See Ten Things: Ten Habits of Highly Effective In-House Counsel.

[4] If you are not a good active listener (or are not sure what the hell I am talking about), check out Active Listening: The Art of Empathetic Conversion and How to Cultivate the “Silent” Art of Active Listening.

[5] See, e.g., Why Vague Feedback is So Destructive and What to Do About It.


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