The Mid-Career GPS Podcast

The Art of an Enhanced Check-In Meeting

July 01, 2023 John Neral Season 1 Episode 6
The Mid-Career GPS Podcast
🔒 The Art of an Enhanced Check-In Meeting
Show Notes Transcript Chapter Markers

Subscriber-only episode

Are your check-in meetings just ticking off a list, or are they fostering growth, connection, and alignment within your team? My name is John Narrell and in today's episode, I'm peeling back the layers of these vital gatherings, sharing personal experiences and practical tips to transform these meetings into pivotal points of career advancement. 

The first part of our discussion revolves around the check-in meeting as a two-way street - a platform for learning, mutual growth, and increased accountability. Drawing from my own experiences, I'll provide advice on how to turn these interactions into opportunities for meaningful dialogue and better results. The second part focuses on enhancing these meetings with your team members. From setting goals to providing timely feedback, learn how to use these meetings to foster trust, motivate your team, and align individual goals with organizational needs. 

However, check-in meetings are not just about managing down; they're also about managing up. In the final part of the episode, I give you a blueprint to maximize check-in meetings with your supervisors, turning these interactions into partnerships that benefit everyone. And as we wrap up, I introduce you to the concept of a Mid-Career GPS - a guide to navigating and enhancing your professional journey. Remember, it's not just about where you've been or where you're headed, it's about how you SHOW UP along the way. Find more resources on

Thank you for listening to The Mid-Career GPS Podcast.
Please leave a rating and review on Apple Podcasts here.

Visit to download your free guide, "5 Mistakes Mid-Career Professionals Make (And Need to Stop Doing) and more information about your leadership and career transition. And other free resources at

Connect with John on LinkedIn here.
Follow John on Instagram & Threads @johnneralcoaching.
Subscribe to John's YouTube Channel here.

John Neral:

Welcome to The Mid-Career GPS Podcast Plus. I'm your host, John Neral. This is the subscriber or paid version of my podcast And once again, thank you for your support. My goal here is to go deeper with you on specific topics and share knowledge and information to help you navigate and build your mid-career GPS more intentionally and effectively. As always, the content shared here is for information only, and I'm here to offer that information to help you build your mid-career GPS to whatever is next for you and your career. Now, my friends, as you get ready for the 4th of July holiday or you're coming back from it, i hope it was a safe and enjoyable time for you and your family and friends. For Richard and me, we're going to spend some time with friends and we'll also be welcoming some dear friends, who we truly call our family of choice, to celebrate Christmas. Yeah, i said Christmas because, due to various circumstances and I got COVID again back in December we weren't able to celebrate Christmas on Christmas Eve, when we normally do. So we are literally going to do Christmas in July. Well, for this month's episode, i want to talk to you about the importance of check-in meetings and whether you currently have direct reports or are conducting regularly scheduled meetings with team members, or maybe you're attending check-in meetings with your supervisor. The tips I'm going to share with you are intended to help you have more effective check-in meetings that ultimately drive better results and create greater accountability. Depending on the language in your organization, the people who you manage or lead they may be called direct reports. They may be called team members. I tend to use those terms interchangeably, so whatever those words are that describe the people who you sit down and meet with, just go with that. Now here's the thing And this is a big topic of conversation I have with all of my coaching clients is that check-in meetings are extremely important. Now, for me, why I enjoyed them so much was that I always looked at it as a time for me to sit down with somebody who I was going to learn from. It could have been a department chair, a supervisor, a manager, an administrator, but I always looked at that as an opportunity to learn And, admittedly, i felt a little disappointed when I walked away from that meeting and didn't get a whole lot of it. A whole lot from it, and what I initially thought as my career was developing was that I was being let down by the people who were leading me And on some level, i'm going to acknowledge that's true. But there was also more I could have been doing, and when I started managing and leading teams, having an opportunity to check in with them was something I also looked forward to. I wanted to know things about their work and what was going on with them, and I wanted to honor and protect that time as much as possible. So the first thing that I want to offer you today, as we talk about building this full-proof check-in meeting, is that you have to honor the importance of the check-in meeting, whether you are the manager or you are the direct report. The reason why these check-in meetings are important is that they're designed to move you forward. They're intended to share some information, work out some problems, celebrate successes and then set up accountability structures that, as you move on to whatever is next, you have clarity in terms of what you are doing. So I don't talk about this story a tremendous amount, but I'm going to share this with you here. When I was studying for my master's degree my master's of arts and teaching at the same time I was going to get a minor in mathematics because that was going to be the subject area I taught And in order for me to fulfill the requirement of getting to 30 credits, i needed to take Calculus 3 as an independent study. Okay, just groan with me here, because Calc 3 is, it's intense. And I ended up taking the course from a professor at the university who wrote the book, and it was his book And I thought, well, okay, this is, i can do this, i'm smart and I can figure this out, and I have him for questions And so every week at an assigned time I would go to his office hours and we would work through whatever problems I was having difficulty with. So I go the first week and I'm like it's probably not great, but let me clear up some questions. I go the second week and I don't get a whole lot from him And I'm thinking to myself okay, i don't really want to get behind the eight ball here too much And I don't want to have to drop this course because I need to graduate on time with my master's in teaching and my mathematics certification, so I can strategically position myself to get a really good teaching job. And I go in the third week and I am floundering And this man looks at me and he says to me why do you repeatedly come in here and bother me with the same questions, week after week? And I just looked at him And I was so taken back by what he said that I was like wait a minute, hold on. And they didn't really know what to say. And so, in the opportunity of having a pause, he looks at me and he goes maybe you should just drop the course because you can't handle it. And I sat there in his office that, like most college professors, offices, in my opinion, are messy, but they know where everything is And I folded up his book and I handed it back to him and I looked at him and I said, finally, you said something to me. I understand. And I walked out of his office. As I often say, being from New Jersey is part of my charm, and sometimes it's not part of my charm, but excuse the language for a second I was so pissed. I was so pissed that he wasn't taking any ownership in this relationship and that I was quote unquote bothering him. Well, i dropped the class. I didn't graduate with my minor in mathematics. I actually ended up getting a great job and I finished my mathematics minor my first year of teaching, and when I talk about honoring the check-in meeting, what I want you to take away from this part of this episode here is that it needs to be important to both parts. Both parties need to be able to come to the table ready and willing to be engaged. Nobody is being bothered. If you are being bothered, then you need to check the reasons why around that. Looking back on that whole situation, there are things that I learned from that that changed the way I approached check-in meetings and how I conducted check-in meetings. And so to help you with this foolproof plan for your next check-in meeting, let's talk a little bit about what should happen before the check-in meeting. So this is coming from the person who is coming to you. They're a direct reporter or a team member. They're coming to you for the meeting. This is the expectation I am offering that you should set with them. What I'm going to offer you here is to communicate to your team members that, at least 24 hours before your scheduled check-in meeting, they send you an agenda. It doesn't have to be anything formal, it can simply be an email, but in that email it needs to communicate the things they want to discuss with you and work through during that check-in meeting. It serves two purposes. One, it helps them be more intentional about what they're coming to discuss at the check-in meeting with you. But secondly, it helps you be prepared. Let's acknowledge, you're busy, you have a full plate, you're taking care of a team and you also do not want to let anybody down. And in not letting anybody down, you want to be prepared. So if you know what somebody is going to come to with questions ahead of time, even if you just briefly read the email when you get it, you'll think about it. You'll think about it as things come up. So this is about helping you be prepared. If the role is reversed and you're going for a check-in meeting with your supervisor, i want to offer you to do the same thing 24 hours before your meeting send them an email that says, hey, really looking forward to our conversation, just to give you a heads up. Here's what I want us to talk about. Agendas set the stage for what you want to talk about, and it helps both parties prepare for the meeting so they can show up at their best. And if you're like well, i don't really do this with my team members and this is going to be a really hard lift to implement this. It's not. You can communicate this at your next team meeting. You can send an email to everybody, or you can just send an email to your team member that's going to come meet with you and say, hey, i'd love to know what you're thinking about in prep for the team meeting. Before the meeting, 24 hours beforehand, just send me a few talking points. I just want to be more prepared. You can totally do that, but agendas help set the stage. Now, when you get to the actual check-in meeting, here's what I want to offer you to do. First and foremost, you set the goal or objective for the meeting. When I have a coaching session with somebody, one of the first questions I'll say to them is how can I help you today, or what's your goal for today's session? I ask them that question because I want to hear from them what is pressing on their mind. What do they want to work through? Now, my clients are prepped that they pretty much know when they come to a session, they've got things for them to work on that they want to discuss, and so part of that is to help me frame what their goals are, and then I know how I can help them move towards success during that coaching session Right? So when we set the stage and the expectations for what we want to discuss and the resolutions we want to have by the end of the meeting, we frame the conversation right off the bat. This is why check-in meetings do not have to be long 20 minutes, 30 minutes. I know some people that do 45-minute check-in meetings and to me that is dreadful. When I was managing a team and I had 11 direct reports, i did not have the time to do 45-minute check-ins with people. It was 20 or 30 minutes and I scheduled them on certain days. Boom boom, boom, boom, boom. Here we go. It's important for me to also share with you here that when you schedule these check-in meetings, let's acknowledge, sometimes things come up. This may come up on your team member's end, they may come up on your end. Look, if you're pulled into a meeting with the EVP or the CEO of your company, you're going to drop everything to go to that meeting. What I want you to remember here is to not drop the check-in meeting. So I always made agreements with my team members that said, hey, if for any reason I need to cancel our check-in meeting and I don't reschedule that meeting within 24 hours, remind me. I want to make sure we meet on a regular basis. Sometimes we would and other times they'd be. Like you know, i got a lot going on. Can we just skip it this week? Okay, but like that rule about never missing twice, we never missed a check-in meeting twice. So now, when you're in that check-in meeting and you have the agenda, what are you going to discuss? Well, a lot of times you're discussing business matters. These might be technical issues, personnel issues, there might be things around their professional development or their project management. It's also a time to communicate feedback. I'll do another episode at some point about feedback. But the thing about feedback it has to be timely and relevant And we need to all be better at giving and receiving feedback. In a check-in meeting where you are building trust and creating a safe space, it's a fantastic environment for you to be able to give feedback to your team members, especially if you are the person who is in charge of writing their mid-year or annual review. Nothing should ever be a surprise at those performance appraisal meetings. I've done a number of episodes on the podcast specifically about that and helping. So keep in mind that feedback you give can absolutely be around how they led a meeting, how they contributed in a meeting, where their technical skills are improving or where they might be lacking in certain things. Check-in meetings are not rah-rah meetings. Check-in meetings are times for you to have intentional conversations that move your relationship with your direct report further. The other thing that I want to acknowledge here in terms of setting up your check-in meetings so you have the agenda, you have business matters that you're going to discuss. The third piece here is what kind of development are you doing for your direct reports or your team members? So, asking them questions like what do they need to do their job better? What do they want to do? Is there a stretch goal or an edge move that they want to be able to do? but you may be able to partner and support them. How are you checking in on their professional needs that ultimately meet the organization's needs? When we think about retention, this is a huge part of it. When we think about retaining employees, it is about making sure that they're seen, heard, acknowledged and validated and they have opportunities to grow And not everybody gets promoted. But if they're not on a promotable track or they're not promotion eligible, more than likely they're going to get frustrated and they're going to leave. So using check-in meetings as a way to keep people engaged I've seen this firsthand. There are times when I had check-in meetings with people and let me tell you it was about pulling them off of the proverbial ledge because they were so frustrated at other things that were happening. You are not a fixer. You are not a therapist in any way, shape or form, but you are their most immediate support in their organization. When people think about how they feel at work, you, as their manager or leader, you're going to be one of the first people they think about. In terms of developing, there are opportunities where you may develop skills. You may also have career development conversations, and sometimes those conversations can be pretty difficult. For example, you may be talking about how likely it is for them to get promoted within the organization. Or you may have somebody come for a check-in meeting and they may share with you that they're really frustrated. They don't feel like they're ever going to get promoted there, and you may have to have that intentional conversation with them that simply says I can understand you feeling that way And part of me needs to simply say that we value you, we appreciate you, you're doing really great work, but you're also 100% responsible for your career And if this place isn't fulfilling the needs, then what are you considering? I can share with you that there have been several times across multiple organizations where I have had a similar conversation like that with a team member or direct report whom I simply said to them great, so this place may not be the best place for you. How do I help you so you can strategically position yourself as you move out? That is a conversation I will tell you. I never went to my management and directly said, hey, by the way, they're probably going to leave. I never did it like that, but it's so important that we honor where somebody's developmental goals are and how we support them. I was having a conversation recently with a client and one of the things I said to them was I know you like the job you're in and the company you're at. I really hope that is not where your career ends. And they looked at me and I said your growth is determined by what you're doing right now And when you think about moving forward and you think about the people you're leading, more than likely the same team that you're leading right now is not going to be the same team a year from now or five years from now, and you're not going to be the same person either. So your development is important as well. We get people, we get to manage and lead for a very, very short period of time. It's one of the greatest gifts and privileges I believe we have in our work when we get to lead people. So sometimes we have to have those conversations that really are about their career trajectory and what that looks like. Additionally, in the check-in meeting, you can get a ton of stuff done, as long as you both hold each other accountable to being focused and on task. Additionally, to help you with this foolproof meeting, i want to offer that it can't be all about work. So find to ask them something that's personal and appropriate about them in their lives. Maybe it's what they have an upcoming vacation planned or what their interests are. Or you know, hey, do you have a good weekend? Do you do anything fun? Are you watching anything interesting on TV? Or you might say, hey, have you happened to check out this restaurant or do you have any good recommendations in the area? Something like that, where it's not all work that in part they get to know you a little bit more and you get to know them. When we think about how we build know, like and trust factor, it's about that connection we create. So if we're not creating that strong of a connection, you as the leader, that's where you're falling short. Creating that kind of connection does not mean you are this super extroverted open book and you're just going to expunge all of your deepest and darkest secrets. You should not do that. That's completely inappropriate. You should not do that. But let them in a little bit. You know, for me it was always about what I was watching on TV or sharing about a recent bowling tournament or where I traveled over the weekend Things like that. Find a way to engage. You're going to find when you do that, you have some very interesting people on your team. Here's another question you can ask Tell me something about you. I don't know already. That could be a lot of fun. Now, as you go to wrap up this check-in meeting, you must set accountability for whatever next steps are going to be as a result of this meeting. Setting up accountability does three things. One it is absolutely vital to continuing the conversation. In that accountability you don't have a way to check in between meetings or it leads to report back when you come back to that next meeting Hey, here's what's happened since we last met. Secondly, it helps build rapport and trust. Remember that trust is repeated behavior over time. So when you hold a team member accountable, you have an agreement about what that accountability looks like and you follow through on it. You're building trust. Right, trust doesn't have to be where you go to their boss and they say something to you like hey, i'm thinking about leaving in two months. I just want to give you a heads up. Can I trust you to keep that to yourself? No, that's not what trust. Yeah, it can be, but it's not what I'm talking about here. I will tell you, i have known bosses who have been given that information quickly. It was like oh, someone's going to leave. You have to really make sure you know you can trust them with that stuff. It's why I always say keep your cards close. Don't show them all your cards. That's another topic for another time too. But the last thing is is that when we set up this accountability, you actually strengthen the relationship because they get to see you more as a trusted resource, technical or subject matter expert and somebody whom they know is in their corner. So accountability is huge. So, as we move into the check-in meeting and what happens after it, one, you have to follow up on the accountability. But I want to offer you here that the accountability really needs to be owned mostly by your team member, so they're going to be the ones to follow up, circle back and keep you informed. This can be a dangerous pitfall for you as a mid-career leader and manager, because if you've got, say, six people on your team and they're like, okay, well, email me about this and have me check in, you don't have enough time to do that in your schedule, you don't? I only say that because I tried it. It failed miserably. So what you want to do is say, great, by close a business on Thursday, i want you to give me an update And I'm going to look for an email from you that's going to have this, this and this. If, for any reason, i don't get that email from you and close a business on Thursday, i'm just going to ping you, be like, hey, don't forget to give me an update. That you can do, because all you're going to do is you're going to make a little mark in your calendar. That's going to be like follow up with team members on accountability You block off 15 minutes and it's done, so I want to make sure you get their accountability in Then. Whatever you need to do as a result of that is accountability steps that have been set up. You can figure that out later and take care of that Additionally. After the check-in meeting. You are always there for support, but that check-in meeting, that check-in meeting is sacred time. I cannot begin to tell you how many people I have coached or talked to that when they have expressed frustration on their job or their previous job, that one of the biggest complaints was their boss never honored their check-in meetings. They never had time to talk to them. I hear things like they don't care about me, they can't be bothered, i don't know what I did, but they don't talk to me. I never, ever, ever want anyone to feel like they're being dismissed. So you may be the kind of leader that gives and gives and gives and is always there for your team, and if you're listening to this podcast, chances are you are exactly that kind of leader. But let's talk about you and the relationship you have with your supervisor. Sometimes we talk about you have to manage up, and my thoughts on managing up are it's all about helping your manager, because they're overwhelmed and overworked too. So if you can make their job easier, it's better. So when you need to manage up to your supervisor for your check-in meeting, here are some things you can do. Number one be proactive about an agenda for your meeting, even if they don't require one. 24 hours before you meet with your supervisor, send them an email. Here's what I want to discuss with you. Number two ask for development. Where do you want to grow stretch? What do you want to move toward? What kind of opportunities are you looking for? Looking for development and being clear about what it is that you want. Please don't go into that meeting and say I'd really like more responsibility. You have to identify it. I'd like more responsibility with this project, this client. When there's a new project coming on board, i want to be the one to lead it. Asking for those kind of development opportunities are clear and cleaner, so your boss or your supervisor can decide whether or not you're the right person for that. Additionally, you want to be able to seek feedback, just like in asking for development. Be very specific about the feedback you want. I remember very vividly working with an executive who was so frustrated that their team members kept coming into their meetings and saying how am I doing? Am I doing okay? Am I going to get promoted? It frustrated the heck out of them because they were like do you know how many people I interact with every day? I want to give them a good answer but I can't. I said to them have you considered asking a more specific question? They were like what do you mean? I was like when they say how am I doing, just say with what. They were like huh, i'm like yeah, two words totally shifts the tone of the conversation. Hey, i'm wondering how I'm doing with what. The more specific you can be about the feedback you're looking for, the better your supervisor can help you with that Because, remember, you don't know if they're good or what you probably do. Like how good are they at giving feedback? but some supervisors aren't great at it. So if you can give them something specific to look for, you're making their job a little bit easier in that regard. But the accountability steps that come after that again, the clearer and cleaner you are about what the follow-up looks like is key to the success of that check-in meeting. But here's the other piece I want you to take away from this episode When we think about this foolproof method. I've outlined for you what happens before the check-in meeting, during and after, and the same goes true for when you go to have a check-in meeting with your supervisor. I want you to commit to this for a minimum of three months, and in doing that, you are going to test and see how well this process is working for you, your team and your supervisor, and after three months you can take a step back and reevaluate and say, hey, how good is this working? Do I keep it as is? Do I change something up? But that's so important, it's so important for us to give things that we're implementing a little bit of time to see if it works. Let me know what you think about this. Let me know how this process is going for you. Let me know what's working for you with this and what isn't. Ultimately, at the end, you, as the manager or leader or executive, must own the check-in meeting. You're creating structures in place to delegate certain responsibilities and protocols that are giving ownership as well to your team members and direct reports. I always looked at this check-in meeting as a partnership. You come to the table with things, i come to the table with things. We're going to discuss them. Creating an agenda means those are the things they want to talk about. You can also share your agenda with them as well, going into the meeting. You can do that too, but in that, always think about this as a partnership, because when you go through that meeting and you create those accountability steps, it is you and your direct report working in tandem on whatever you have agreed on. You have an agenda as well, but that agenda should always be about maintaining behavior that your direct report is doing, maintaining performance or shifting that performance And that may either need to be a course correction or an acceleration. You're doing really well with this. Let's increase some responsibilities, but we're always taking that check-in meeting and moving things forward, all right. Thank you so much for spending some time with me today on this premium episode of the mid-career GPS Podcast Plus. If you have any questions, you can certainly follow up with me. You can contact me at johnandjohnnarrowcom or direct message me on LinkedIn. That's the best place to find me. You can also find me on Instagram and Facebook at John Narrow Coaching. But until next time, my friends, remember this We build our mid-career GPS one mile or one step at a time, and how we show up matters. Make it a great rest of your day. Have a great summer. Happy Fourth of July as well. Take care, bye-bye. Thank you for listening to the Mid-Career GPS Podcast. Make sure to follow on your favorite listening platform And, if you have a moment, i'd love to hear your comments on Apple Podcast. Visit johnnarrowcom for more information about how I can help you build your mid-career GPS or how I can help you and your organization with your next workshop or public speaking event. Don't forget to connect with me on LinkedIn and follow me on social at John Narrow Coaching. I look forward to being back with you next week. Until then, take care and remember how we show up matters.

Effective Check-in Meetings for Career Growth
Effective Check-in Meetings and Development
Maximizing Check-in Meetings With Supervisors
Building Your Mid-Career GPS