I was recently talking to someone in my network that I connect with every so often, and he was lamenting that he had an every-other-week check-in with his manager scheduled for the following day. He mentioned it as a random aside, effectively complaining about how he was going to “waste” an hour with his boss instead of getting something done. I thought that was interesting because while I won’t go so far as to say that I live for one-on-one meetings with my manager, I certainly don’t dread them. I do see the point about wasted time though; I can somewhat empathize with someone wishing they were able to use time they feel is wasted on meetings productively. After all, it never feels like we have enough time to get everything done. However, if you think time with your manager when they are focused 100% on you is wasted time - I think you are framing the one-on-one conversation with your manager in the wrong way.
You and your manager are a team. But if you’re high fiving during meetings, you might want to rethink how well you’re social distancing.
I often think of this meeting as an important way to ensure that my manager and I are in alignment on what our team priorities are. I’ve found that if we use the time effectively to ensure that I understand my manager’s expectations and I communicate what my blockers and concerns are, we end up saving far more time and effort than the meeting “cost.” Additionally, these are super-valuable meetings if you’re looking to gain some clarity about the trajectory of your career. It’s quite literally the only forum where I can ask what my manager sees me doing in a year or three, and provide my input into what I want to be doing in that timeframe. Finally, it’s my manager’s job to have the relationships across the business to be able to put the work I’m doing in context. I want to hear what he’s talking about with other areas of the university so that I can ensure that our technology roadmap matches the university’s goals and strategic direction. In short, I think it’s one of the more valuable uses of an hour each week.
Still, if you find yourself dreading spending face-to-face time with your manager, I’d like to make an attempt at turning your perception around - especially if you work in IT. I don’t think that just repeating that these meetings have real value will be useful, so instead I’d like to give you a few tools, questions, and suggestions that I think can help you uncover some of the value while you’re having that conversation.
First, you should try to minimize the amount of time where you’re just sharing updates on what you’re doing and any project statuses. I have found that keeping my manager updated on what is going on is best done over an email ahead of the meeting. That way, he can read it in advance and I spend less time simply giving him a readout on what I’ve been doing. Instead, we can actually talk about it. Maybe he wishes things were going a little faster, or I have a challenge that he could help out with. I really believe the valuable part of meeting is when you’re having an interactive discussion or conversation about the topic instead of simply talking at someone about what has been going on.
Don’t skip the notes part. I spend significant effort on this part, because it saves me a ton of effort during the meeting. Also, I type mine because my handwriting is straight outta med school.
In addition to sending updates via email in advance, I also take the time to make sure I have a concise list of notes that I want to cover during the meeting. I’ve known some folks who like to write out their notes longform as if it’s a script of what they intend to say, but I greatly prefer to simply list the topic then any salient points, and (this is the important one) an ask of my manager. Sometimes I’m looking for insight, direction, or an opinion, but in order to make sure I’m not backsliding into a soliloquy on status updates I make sure I highlight what I’m asking for. Often, we won’t be able to cover everything, so I make sure that my list is prioritized before the meeting starts so that I am certain to get the most pressing or important topics covered right off the bat in case we run out of time. As a pro tip, I usually write my notes on one side of the page and leave the other half so I can jot down outcomes or additional notes as we talk. If you have a memory like a steel trap then maybe that’s unnecessary, but I recognized long ago that my memory is more of a liability than an asset; I often forget names of people in my family, so I make sure everything is written down.
One of the things that I make sure I do in my notes is to be very clear about any technical details I’m trying to communicate. In most cases, your manager will not be as technically proficient as you are in the details of your particular craft, so spend some time ahead of your meeting making sure you know how you’re going to present the details. Does anything need to be translated or defined for your manager to really get the crux of the issue during the conversation? If so, perhaps this is a good topic to put into your update email, leaving enough time prior to the meeting where they can ask clarifying questions. The last thing you want to be doing during a limited time window is spend the effort explaining the differences between an availability group and an availability zone – that can be done out of band most of the time.
Before I wrap talking about the notes, you should try to anticipate what your boss may want to hear about, and then make sure you have good notes around that topic. A great way to figure this out is to pay attention to the last few meetings. Was there a topic, project, or issue that your manager was asking a lot of questions about or spending a lot of time on? If so, you can bet that they’re probably still really focused on that topic, so make sure you have detailed thoughts around those areas. As a manager myself, I absolutely notice and appreciate if my team comes to a meeting ready to talk about the topics that I’m most interested in – it means we’re in sync, and that’s really valuable. The point here is to make sure that you don’t get in that awkward position of being asked about something that you should probably know, but aren’t ready to answer. Minimize those times as often as possible.
Okay, so you’ve sent an update email, you have some quality notes in a prioritized order, now it’s time to have the meeting. One of the things that I’ve always tried to keep in mind is that my manager has a lot of concerns that aren’t directly related to my area on any given day. For instance, perhaps the HR system is having issues, and that’s really in the front of his mind because it’s a pay week and HR is on a tight timeline. You can often tell pretty quickly, but it never hurts to start a meeting by simply asking “What’s front of mind for you today?” I’ve learned a lot about the organization I work for as well as what is coming down the pipeline by starting a conversation about what my manager is thinking.
One question that I make sure to ask on a pretty regular basis is if there is anything I can be doing to add more value or if there is anything that I could be doing better. I’ve found that many managers - despite being in a role where their job is to keep striving for better and better performance out of their team - sometimes don’t like to address anything that could be considered confrontational. So instead of putting the onus on them to say something, I open the door to feedback by simply asking for it. Do I get feedback on some stuff I need to work on? Yes, absolutely. But that’s how I know what to spend time on to keep improving. Some of the best conversations I’ve had with any manager have come after I ask what I can be doing better. On more than one occasion, it surfaced a disconnect in that something I was doing well wasn’t being noticed. In fact, one time I was told I could be better at documenting, and when I asked what they meant I was told I didn’t keep any documentation. That same day, I showed my boss my file share with a ton of documents and spreadsheets in it; just a few weeks later, my review showed that I was leading the team in terms of documentation.
My memory is exactly like a whiteboard
….that gets erased after each and every meeting.
True story: This is why I photograph whiteboards in meetings. Microsoft Lens for the win.
As my time with my boss is wrapping up, I always like to ask if there’s anything that we didn’t talk about that they wanted to or if there is anything else happening in the technology environment that I should know about. Now normally, there isn’t anything because we both came to the meeting prepared and we worked down our respective lists, so anything we didn’t get to just wasn’t pressing enough to get to the surface. However, I still ask not because I expect there to be anything - but because I’m trying to send the signal that I’m open to any other requests, projects, or feedback. It’s a simple way to make sure that we both know that the conversation is ongoing. Then immediately afterwards (and I mean immediately afterwards), I go over my notes and make sure to put any action items into my daily or weekly plan depending on when I need to have them completed by. This way, everything is fresh in my mind so I don’t miss anything – we did talk about my memory issues, right? I don’t remember for sure.
One final thought before we call this one finished: none of these tips are worth anything if you don’t regularly meet with your manager. I’ve given presentations before about how to get the most out of meeting with your boss and had someone ask how often they should be meeting. I tend to think something between weekly and every third week is appropriate, depending on your organization, autonomy, level in the org chart, etc. However, I’ve talked to a bunch of people where they have one-on-one meetings with their boss quarterly or even less frequently. One such attendee told me that they meet with their boss annually at review time. In my opinion, that’s just too infrequently to actually say you have a productive relationship. If you’re not getting any face time with your boss, it’s likely a bad sign about how important they feel that you are to their success. I would strongly suggest you get on their calendar more often, just make sure you put in the effort to make the meeting valuable so that you (and they) want a repeat!
Hopefully, if you follow through with some of these tips, you can turn your manager meeting from something you have to do to something you want to do because you see the value for your career and the organization. And if that’s a bridge too far for you, maybe you can be so overprepared for the next meeting that you get a week off.
Questions for reflection:
Do you dread spending time meeting individually with your manager? Why do you think that is?
Do you make sure you have notes ready and prioritized before a one-on-one meeting? How long would it take to do so?
How can you ask for feedback from your manager in a way that shows that you’re open and eager to grow and improve?
