A few months back I took some swings at meetings in general, i.e. Escaping Meeting Hell. But, as I noted, not all meetings are “bad” and many are necessary, especially for in-house counsel. Of the meetings in-house counsel must attend, none should rank higher than your 1:1 meetings with your boss. You may think it is just more administrative nonsense you have to make time for during your already crowded week – and you would be somewhat correct. But, it is important administrative nonsense and the administrative part of being an in-house lawyer is just as critical as the substantive legal work. Not only is a one-on-one meeting a way to keep your manager informed of what is going on, it is also a key ingredient of the “soup” that is served up as part of career development and advancement.
So, grab your spoon and get ready to dig in as this edition of “Ten Things” discusses what you can do to have more effective 1:1 meetings with your boss:
1. Why it matters
Though it may seem like a fairly mundane meeting, as a long-time manager of people I can tell you that a 1:1 is one of the most critical meetings you will have during any week. For starters, and as I have written many times in this blog, in the in-house world you are constantly being weighed and measured by senior management who want to know if you have the “right stuff” to move on to the next level or higher. A 1:1 meeting is often one of those measuring sticks. This means you need to take it seriously and do the things necessary to maximize the value of the opportunity, both for you and your boss. While a 1:1 is generally about keeping your boss informed and staying aligned (i.e., “no surprises”), it is also a way to build your personal relationship with your manager, including gaining their trust and allowing them to see the full value you bring to the department and the company – as a lawyer and as a team member. Outside of a formal review, it is one of the best ways to get feedback on how you are performing (either on a specific project or overall at that point in time). Finally, it’s a chance to discuss topics that don’t often come up in the normal day-to-day exchanges between manager and employee, e.g., career development opportunities or things blocking your ability to get something done. In short, if you are fortunate enough to have a manager who schedules regular 1:1 meetings with you, take advantage of it!
2. Set a regular cadence
I participated in weekly 1:1 meetings as an in-house lawyer pretty much from my first day in the American Airlines legal department way back in 1994. The process carried over to Sabre Corporation, Travelocity, and Marketo. So, for me, weekly 1:1 meetings were and are the norm. Based on conversations I have had with many other in-house lawyers, it appears to be the norm at most places. But, such meetings are not the norm in other parts of the business, i.e., those employees and managers have 1:1 meetings on a more ad hoc basis. I cannot explain the discrepancy, but I can tell you that it is imperative to set a regular cadence for your 1:1 meetings. Generally, it should be the same day, at the same time, at the same place every week (or every other week if that is preferable). A cadence is important because it gives you a framework to plan around, e.g., if your 1:1 meeting is spur of the moment then it is highly doubtful you are going to get the most out of the meeting due to poor planning alone (though never pass up any type of meeting with your boss – the more the better generally). And if you or your boss cannot make your scheduled meeting, get it rescheduled as soon as possible – even if it’s later that same day. I would work with my manager’s administrative assistant to reschedule (vs. leaving up to him or her). Moreover, find a place to have the 1:1 that is conducive to an open discussion. An office or small conference room is ideal. If not available, sometimes a table in a crowded cafeteria can actually be more private than a discussion in an open area.
3. Prepare an agenda
As a manager, I was surprised by the number of times some of my direct reports would come to their 1:1 without any apparent agenda of items to discuss. Not only did that make it a more of a short “shoot-the-breeze” session, it also made it a missed opportunity for them because a) coming to a 1:1 with nothing on your list makes a terrible impression, and b) inevitably I would get an email later in the day from them saying “I forgot to tell you about …” (which probably meant another meeting for just that topic, which was awesome). To be sure you are maximizing the time you have with the boss, to ensure you’re not forgetting anything, and to force yourself to think through everything you want to raise and how you want to raise it, prepare an agenda for every 1:1 meeting. Leaving the content of the meeting solely up to your manager is a sure way to get the meeting cancelled on a regular basis. And start the agenda a day or two before your meeting, not 10 minutes before. To keep track of potential topics, I created a folder in my email called “1/1” and I saved emails, notes, etc. into the folder to remind me of things to put on my agenda. It’s also an excellent idea to ask your manager a day or two in advance if there is anything in particular they want you to be prepared to discuss. Lastly, when planning for the meeting, you must properly prioritize the items on your agenda as it is likely that your meeting may get cut short or you simply may not get to everything. This is a hint that you should only include the most important matters to discuss at your 1:1 as no one is interested in everything you are doing – not even your mom. So, figure out what is truly urgent or critical and start with that.
4. Be present
Given what’s a stake, the very least you can do is be “present” for your 1:1 meeting. By this, I mean that you are giving your full attention to the discussion, you have eliminated distractions (like checking your phone or laptop), and you are ready to fully engage with your manager. I always tried to leave at least five-to-ten minutes before my 1:1 to clear my head and leave behind any issues or concerns that were not germane to my 1:1 meeting. Try a few deep-breathing exercises and get yourself in the right frame-of-mind for what should be a positive and energizing discussion (or to deliver bad news if that is the case). Also, be sure you have prepare updates that are crisp and to the point. If you have some elaborate, meandering story to tell about Project Y, maybe you need a meeting just for Project Y or, more likely, you need to tighten up what you are going to say during the 1:1. Finally, if your 1:1 is remote (as is typically the case these days), use video most if not all the time. Video forces you and your manager to pay attention to each other and not try to multi-task.
5. Actively listen
You may think your 1:1 with the boss is mostly about you talking. Wrong (well, somewhat wrong). You should give equal attention to listening to what your manager is telling you. Despite our best intentions, sometimes we only hear what we want to hear and we are not good active listeners. Don’t try to anticipate or interrupt what your boss will say next or “think” that you already know what she means. Slow down and let her finish her thought or sentence and then let it sink in for a few seconds. It may be something clearly good (or bad) or it may be a subtle hint about something they want you to do or want you to improve on. Listening carefully also gives you a chance to think through what you are going to say in response (a skill we can all work on) or improve the “pace” of the meeting; in particular, to slow things down so it is a discussion vs. a race to tick items off your agenda. And it allows you to focus on the non-verbal cues from your boss as well as improving on your own, e.g., eye contact, sitting up straight, strong presence, and so forth. One good trick for learning how to be an active listener? Take good notes! Seriously, you should be writing down plenty of notes from your 1:1 session. The act of taking notes forces you to listen carefully and absorb more, and – since there is no way you’ll remember everything said – you can save yourself the embarrassment of having to go back and ask just what exactly she wanted you to do again on that one assignment.
6. Ask for feedback
One common missed opportunity during a 1:1 meeting is the chance to ask for and get feedback from the boss. Believe it or not, many managers are uncomfortable being the one to start the “feedback” discussion because they think their employee is going to react negatively to the feedback. Make it easy on them – it is worth the effort because feedback from the boss is one of the most helpful pieces of information an in-house (or any) lawyer can get. I would simply make sure that at some point during my 1:1, I asked my boss whether “there was anything I could have done on assignment “X” to do a better job” or “is there anything I can or should be doing to be a more valuable part of the team or to help out with anything.” Regardless of the phrasing, the fact that you asked for feedback should not only get you valuable input from the boss, it will also make him or her more comfortable proactively giving you feedback in the future and it makes clear that you are someone who is coachable and willing to improve. Two great characteristics for any in-house lawyer.
7. “Will over skill”
Let’s face it, no one is the complete superhero in-house lawyer (I struggled sometimes just to get to sidekick status). No one knows everything, no one has zero weaknesses, and no one is so busy that they cannot learn new things. Your 1:1 meeting is the perfect time for you to emphasize “will over skill.” In other words, showing your boss that you are ready and willing to take on new assignments, to learn and do things out of your comfort zone, to be a leader in the department, and to lend a hand to anyone that needs some help. As most managers know, you can teach skills, but you cannot teach drive. I will take someone with drive and general smarts over someone with skill but a bad attitude any day of the week. Here’s what I looked for during 1:1 meetings with my direct reports:
- Shows leadership (someone who does not always have to be led, but can step up to lead – wants to lead).
- Takes ownership (someone who “owns” their projects and doesn’t need to be micromanaged – gets things done, does the little things, looks for more, thinks beyond the task at hand).
- Willing to learn (takes failure in stride and as an opportunity to get better, learns from the mistake, not defensive, no job too small or too big, has good habits).
- Is an ambassador (can help “market” the department to the business, is easy to work with, articulate, empathetic, can put in a room with senior executives and not be a wallflower).
8. Sample Topics
For the most, finding things to discuss at their 1:1 is not a problem (prioritizing is). Still, if you make the discussion only about what you are working on, you are not fully considering all that is “on the table” when you get the chance to talk with the boss (hint: it’s not just a status update). Here are a few things to consider discussing or asking about at every 1:1 meeting – and you can work the high-level ideas here into your 1:1 agenda outline:
- Raising critical projects you are working on (and do not put anything on your list that you are not truly prepared to discuss. Nothing looks worse than you raising a topic and it becoming quickly apparent that you have not thought through everything).
- Noting any roadblocks you are facing getting things done.
- Sharing your wins!
- Asking whether “there is anything you feel is critical to discuss today so I can be sure to address it here at the beginning?”
- Requesting feedback on specific assignments (or generally).
- Asking how you should prioritize your workload.
- Showing how you are progressing vs. any individual KPIs or yearly goals.
- Noting the pulse of the team (i.e., what you’re hearing in terms of morale or any major issues – good or bad).
- Pointing out problems you’ve spotted and potential solutions (never bring just problems to the table).
- Recognizing others for their work (both inside and outside the department).
- Raising at least one thing you are doing or considering that you think is “strategic” in nature and/or value-generating for the company.
- Volunteering for projects/tasks, or expressing your willingness to take on more/different types of projects.
- Reporting back on any “go do’s from prior 1:1’s (or any other assignments the boss has given you).
- Raising immediate career goals if the opportunity to discuss arises, e.g., different types of projects you are interested in, helping out with the administration of the department, etc.
You don’t have to discuss every one of these topics at each 1:1 meeting, you can make some “always-on” the agenda and others as they naturally arise.
9. Closeout strong
It’s smart to end your 1:1 meetings on a high note if possible. Always prepare one piece of “good news” to share with your manager. Typically, they mostly hear about problems and complaints, so bringing them something “good” can be a strong way to end the meeting. Likewise, be sure to clarify any assignments where you may not be 100% sure of what is being asked of you. The 1:1 meeting is the perfect place and time to make sure you are headed in the right direction. Likewise, ask the boss how she/he is doing and whether there is anything you can do to help them. Also, I always made sure I knew and remembered a lot of personal information about my bosses, e.g., spouse’s name, children, where they went to college or law school, favorite sports team, birthdays, anniversaries, etc. (the company website and LinkedIn are great sources). And then I was sure to ask them how their family was doing or if they caught the “Giants” game that Sunday. Just a question or two on a personal note can go a long way to helping build a better relationship with your manager, one that can help you transcend the typical small talk and launch you into their inner circle of trusted advisors.
One thing that always frustrated me as a manager was the lack of follow-up by someone. Your manager should not have to chase you for a status report or even whether you actually finished the assignment or not. Keep a clear record of any “go-do’s” coming out of the 1:1 – or other asks from your manager – and make sure you report back to them on the status during your next 1:1 (or sooner if the circumstances warrant). You don’t want them to suddenly realize a month or two down the road that you never reported back on something they had asked you to do – that is not a fun discussion.
So, there it is. My pitch for everyone to reconsider and refocus on the importance of 1:1 meetings and the things you can do – as an employee – to drive better and more productive discussions with your manager. All of which will reflect positively on you – regardless of where in the world you practice. Of course, there is plenty more to talk about regarding 1:1 meetings but this is a blog, not Moby Dick. But, you can easily find more material on effective 1:1’s via an internet search. More importantly, recognize that there is an incredible amount of value you can unpack from a 1:1 meeting if you properly prepare and give it the level of attention it deserves. If you are fortunate enough to have such regular meetings, don’t let the opportunity go to waste. If your boss isn’t a fan of 1:1 meetings, try to convince him or her otherwise. Next time I’ll discuss 1:1 meetings from the perspective of the manager (and maybe you can show them that post to get them over the hump). Until then, stay well, wash your hands, and keep wearing a mask (we’re not out this woods yet).
June 17, 2020
 See my thoughts on this in the post Ten Things – Career Killers – Things Not to do as In-House Counsel.
 Multi-tasking is a fool’s errand and a way to get less done. If you don’t believe me see https://www.directive.com/blog/why-multitasking-doesn-t-work-and-what-to-do-instead.html
 For more on non-verbal cues in the workplace see https://www.thebalancecareers.com/nonverbal-communication-in-the-workplace-1918470 and https://ucpathjobs.org/working-at-uc/nonverbal-communication-matters-workplace/.
 Remember, a 1:1 is not your formal performance review. So, don’t make every 1:1 meeting about your career development. And when you do raise it, be specific about what you are looking for or want to try, i.e., the burden is on you to advance your career as much as is it on your manager.