How to run effective 1:1 meetings – with Nicole Case, Executive & Leadership Coach

October 9, 2023

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Welcome! We're all about realistic time management designed for professional working women here in this little pocket of the internet. I'm glad you're here.

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Meetings, including 1:1 meetings, can be a big time management pain point. Let’s talk about ways to make sure that we’re making these meetings a good use of everyone’s time. 

To download your 1:1 meeting agenda from Nicole, click here: https://www.theupgradedleader.com/meeting 

You can also follow Nicole on LinkedIn here: https://www.linkedin.com/in/nicole-case-leadership-coach-and-keynote-speaker-for-women/  

And Instagram here: https://www.instagram.com/nicolecasespeaks/ 

A full transcript will appear here within two weeks of the episode being published. 

I also share actionable bite-sized time management strategies on Instagram at https://www.instagram.com/_kellynolan_/. Come hang out with me there!


Episode 24. Nicole Case

[Upbeat Intro Music]

Kelly Nolan: Welcome to The Bright Method Podcast where we’ll discuss practical time management strategies designed for the professional working woman. I’m Kelly Nolan, a former patent litigator who now works with women to set up The Bright Method in their lives. The Bright Method is a realistic time management system that helps you manage it all, personally and professionally. Let’s get you falling asleep proud of what you got done today and calm about what’s on tap tomorrow. All right, let’s dig in!


Hey hey, and welcome back! Today we’re gonna talk about meetings, and in particular, we’re gonna talk about one-on-one meetings. I mean, I don’t think it’s anyone’s surprise that meetings are a big time management pain point. Across a lot of industries, I think women who work in corporate and kind of adjacent fields like nonprofit fields and that kind of stuff, meetings can be such, such a pain point. A subset of those meetings are those standing one-on-one meetings that I know are very prevalent in these fields and serve a great purpose if done well. It is, however, an area I’m not as familiar with because I come from the legal world where we didn’t really have standing one-on-one meetings, for better or for worse.

So because I’m less familiar with it, I invited my friend Nicole Case onto this episode, and she is going to walk us through strategies on how to handle these one-on-one meetings with more purpose and intentionality, and I’ll weigh in with some hopefully helpful time management strategies as well.

So just quickly, Nicole Case is an award-winning leadership and executive coach, a keynote speaker, and the vibrant force behind The Upgraded Leader Podcast. Nicole is on a mission to close the gender power wage gap by helping women corporate leaders get the promotions they deserve, make the impact they want, all without burnout or guilt. I can definitely get behind that. With over a decade of corporate HR experience under her belt, she has the insider knowledge and insights to guide women in navigating and succeeding at that new level on their terms. Her clients and audience members walk away with the tools they need to gain visibility and influence, set healthy boundaries, and cultivate the confidence necessary to thrive in those high-stakes senior leadership roles.

Nicole is a certified authentic leadership coach and was recognized as the top ten leadership coaches to watch in 2022. She’s a devoted cat mom, professional aunt, lifelong Harry Potter fan, and beginner ballet student adding a dash of humor to her own upgraded life’s journey with her husband in North Carolina. Let’s dig in!


How Nicole Became a Leadership Coach – 2:32

Kelly Nolan: Awesome, Nicole! I am so excited you are here. Why don’t you introduce yourself and just explain how you became a leadership and executive coach.

Nicole Case: Yeah, so first of all, Kelly, thank you so much for having me on today. My story is that I grew up in a really, really small town in Western Pennsylvania, a first-generation college student, went to college, and while I worked three jobs my senior year, one of those jobs was working in the career services center at Penn State. And so, I kind of got this taste of helping people with their resumes and figuring out what they were gonna do after college. I was like, “Wow, this is a lot of fun! I should look into this as a profession.

I realized I needed to get a master’s degree, and one of the master’s degrees that people say that you can get in order to be a career counselor is in human resources. I was like, “All right! That sounds great! That’ll make me nice and marketable. If I’m ever in a place where I can’t get a career counselor job, every company needs HR.” So I got my master’s degree in HR, and then after I graduated, that’s the path that I went, and that’s the path that I stayed in my entire career.

So I worked in corporate HR in mostly high-tech and pharmaceutical companies, and the type of HR role I did was what’s called an HR business partner. And so, what these roles do is we get assigned, basically, to a senior executive, senior leader, and that business unit or those few business units are the groups that we support directly. So we are aligned to a specific business group, and we spend our time talking through strategy, talking through how to lead this team and how to run this business from that people lens. So I did a lot of coaching, a lot of guidance of senior people leaders throughout my entire career, and I realized that was some of the favorite things that I love to do. That and training and things like that, I love doing that type of work.

And so, I knew I wanted to be an entrepreneur. I knew that was the direction I wanted to go, and my parents are entrepreneurs, so that’s kind of what was always in me. And so, I realized when I was the president of a women’s networking organization where I met you, actually, Kelly, several years ago — I was the co-president of this women’s group, and I had been hosting all kinds of career types of programs, and I remember being at one of these events. I think we were talking about maybe building your personal brand or personal board of directors or something like that, and I remember an early career woman was asking another woman in the group, who was more experienced, and said, “How do you know if you’re doing this career thing right? How do you know if you’re doing all the steps and stuff like that?” And the experienced woman said, “Well, I opened my wallet,” meaning she hired a coach. I was like, “Oh, that’s what I’ve been doing this whole time for free!” I was like, “Ah, that’s the business.”

And so, I went and got coach trained and all of that good stuff. And so, I started this business back in 2018. I basically just crafted a business out of the things that I loved to do when I was in corporate, which was to coach and guide executives and leaders on how to be really great leaders for their team because I knew when I was in HR that I couldn’t necessarily talk to every single employee or meet with every single employee. There was not enough of me to go around, but I could spend my time being really, really closely aligned with those executive leaders on how to be an amazing leader, and so, that’s where that ripple effect came in where I knew I could be the most effective. Plus HR, we don’t want to get in the middle of your employee relationships. We don’t want that. We want you to be able to lead your team and manage your team without us mucking it all up in the middle of it, right?

So that’s where I just found such satisfaction was just helping leaders be amazing leaders. And so, now I’m doing that on my own in my own business, and I’m focused mostly on women corporate leaders. My business is very female focused. But I will, on occasion, take on an aligned male client if they’re ready for that.

Kelly Nolan: Well, I’m just so jealous that there are, in this corporate space, people who actually help people become managers and become very good managers because, coming from the legal space, there is no such thing, and I think that it’s such, obviously, a critical role, but no one teaches us how to do that. And so, I think that’s just so, so valuable, especially for people in fields where there isn’t that built-in internal HR helping in that way —

Nicole Case: Mm-hmm. Yep.

Kelly Nolan:  — to get that leadership training because it is so hard to be a great manager. Again, it’s like all of the things you’ve done well to get to that point aren’t necessarily what needs to happen as a manager, and I just think it’s really cool that you can support people through that.

Nicole Case: Yeah, totally. The skills that you need to be successful as that individual contributor, we would say, are not the same skills that are necessary to be a successful people leader. They’re totally two different things, and I do think that a lot of times what happens is people are really awesome at their job, they’re super, super good at their thing, and then they get tapped on the shoulder to go to the next level up, and with that comes leading other humans. That’s a whole other ball of wax, right? That’s a whole other thing.

Even if, say you got your MBA or something like that in college or whatever, had a business degree, that doesn’t mean that you were taught how to do any of this stuff at all around how to lead other human beings.

Kelly Nolan: Absolutely. Absolutely. Well, so one of the things we’re here to talk about today is one of those things that, again, no one really teaches us how to do. That is running and just holding efficient and effective one-on-one meetings.

What Nicole Means by One-On-One Meetings – 8:34

And so, before we dig into that, I think especially for those of us who don’t come from the corporate space, when we talk about one-on-one meetings, what do you mean by that? Are we talking standing meetings? Are we talking about any one-on-one meetings? When you say those words, what are you envisioning?

Nicole Case: Yeah, so when I say one-on-one meetings with your team, I am being very specific about this type of meeting. This is a regularly-scheduled, private meeting with an individual on your team. This is not a status meeting. This is not a project meeting. This is not, “Tell me how that meeting went with that client.” It’s not anything like that. It is meant for your employee to bring to you topics that they want to talk about.

I had a leader very early in my career who introduced me to this idea of a one-on-one, and he was always very clear about, “This meeting is for you. This is your meeting. Come with your agenda items. Come with your topics that you want to talk about, that are important to you.” So this is not just like, “Hey, we need to check in on this project. Let’s toss a meeting on the calendar.” This isn’t a 15-minute daily stand up. This is a very strategic, again, regularly-scheduled meeting that is kept sacred. It’s not a meeting that gets pushed or moved or canceled all the time or it’s a nice-to-have.

To me, a regular one-on-one with each of your employees is the most effective use of your time every week. If you are finding that you’re struggling, that your team is not as effective as they could be, they’re not as productive. Maybe there are some cultural issues there you’re finding. Maybe mistakes are being made or turnover or people are just not following through with maybe what you had said that people would work on. This is a great way to solve that and to be able to increase the productivity and increase the engagement on your team.

Kelly Nolan: Got it. Got it. So, from a purpose standpoint of what is the purpose of this meeting, from a manager perspective, do you ever have another purpose other than just having an open floor that’s devoted time for an employee? Is that the sole purpose or is there another one from the manager perspective?

Purpose of One-On-One Meetings – 10:54

Nicole Case: Well, of course, there are gonna be lots of different times you’re gonna meet with your employees. You’re gonna have bigger team meetings. Again, if you work very closely together on different projects and stuff like that, you’re gonna have dedicated meetings just to that. I view these regularly-scheduled one-on-ones, whether they’re weekly or biweekly. Some managers, I would say, if you have a really large team that reports into you, maybe once a month, but you’d really have to convince me that once a month is the right cadence. There Are only a few instances I can think of in my entire career where I was like, “Yeah, once a month makes sense for you.” That was because the manager had 25 direct reports, right? 

Kelly Nolan: Right. Right.

Nicole Case: And they would be spending all of their time in one-on-one meetings. We had to find some efficiency somewhere. But these meetings, first and foremost, are really meant to build trust and rapport with your employees. And so, then, under that umbrella of building trust, rapport, psychological safety, all of that, comes your ability to share clarity of expectations, for you to help people understand the broader mission of the organization, or to just help them with their own learning and growth and career development.

One of the number one reasons people leave companies — and I know there’s the saying that people don’t leave companies, people leave managers, which I absolutely believe. Probably 90% of the time I absolutely believe that. One of the number one reasons people are citing right now as to why they are leaving companies is because they don’t feel like they have enough career development and room to grow in their career in that organization. So they’re like, “Well, I’m capped out here, so I’m gonna move on.”

Kelly Nolan: Yeah.

Nicole Case: And I can’t tell you how many times when I worked in HR and I would do the required exit interview with an employee about why are you leaving, and they’re like, “I didn’t have the opportunity to grow,” and I go back to the manager to say, “Hey, this is what we talked about,” and they’re like, “I had no idea that that’s what they were looking for.”

Kelly Nolan: Yeah.

Nicole Case: And it’s like good gosh, if you would have had a regularly dedicated meeting where this could be a regular agenda item, to be like, “Okay, well, how have you learned this week? How have you grown? What are some projects that you’re working on that are helping develop you there?” Then also you just being able to continue to stay connected on that so when you are in other meetings with other leaders and you’re divvying out projects, you can say, “Oh, hey, I’ve got Kelly on my team. Kelly and I have been talking for the last couple of months that she wants to gain this experience. This would be a really great stretch project for her to get involved in,” right? You’re only gonna get to know and understand those things if you have these meetings regularly, right?

Kelly Nolan: Absolutely.

Nicole Case: Career development for your employee, clarifying expectations, and performance. If you’re finding that people are struggling performance-wise, these are really great places to give that real-time feedback and course correct if you need to course correct. So if something doesn’t stew or spin for multiple months perhaps, you’re able to kind of identify maybe issues earlier on, and you can, again, nip those if you need to, course correct where you need to.

And just finally, we as humans all just want to feel like we’re all being seen, heard, and understood, right? I can’t tell you how many clients of mine even recently have said, “I don’t talk to my boss hardly at all.” A lot of my clients work remotely, and so, a lot of them say, “Oh, I’m not connected with my boss anymore. We’re not having meetings.” Again, most of my clients are fairly senior in their career, and so, sometimes people don’t feel like they have to have these meetings anymore. But yet, then they still come and tell me, “Wow, it would have been really nice if I had a dedicated time to talk to my boss about these things.”

Kelly Nolan: Absolutely, and then from what I work on from a time-management perspective, which leads to a workload perspective, I would imagine — and maybe this is more from the individual contributors’ standpoint, but I think an important thing for managers to keep in mind is also inviting conversation around workload during these times I would imagine is a good fit. Because it’s overall workload. It doesn’t tie to one project or one thing. It’s just saying, as a manager, inviting, “I don’t know everything on your plate, and so, if you are too busy or too slow, I’m depending on you,” and I would imagine saying that a couple of times. That’s something that I advise, repeating that at least twice a year, of inviting that conversation to happen because as you were saying, whether it’s these are my career aspirations or this is my overwhelming workload, I think individual contributors, understandably, assume managers know, and managers understandably have no idea how it all stacks up on the other person’s plate.

And so, that’s another thing I can see coming up, really using this time to at least have that invitation open as a manager and have that protected time as an individual contributor to have that conversation.

Nicole Case: Yeah, absolutely. And if you’re having these meetings either weekly or biweekly, you’re able to continue to get a sense of what your team is working on because you’re so right. Managers have no idea what you’re working on. We like to think our managers always know what we’re working on, but especially the higher up we go in our career, or if our roles are just ones that are just really autonomous, that you’re just working really autonomously, you might not be working alongside your boss every single day, people might be coming to you for things and requesting things from you, and your boss just has no idea, right? They probably have multiple other people on the team they’re trying to tend to, not to mention themselves, right?

Again, the three main things for me are these meetings build trust and rapport because it’s gonna be really difficult to be as effective as you need to be as a leader and as a team if your team does not trust you or feels like they don’t know who you are. It gives you an opportunity to give clear expectations. “This is what good looks like. This is what I expect you to be spending your time on,” and it ensures that you stay aligned, right, so that you don’t have an employee going on in left field for the next three months, and you’re like, “Whoa, whoa, whoa. That project was not the top priority. We’ve let this other priority fall,” right?

I remember even just myself in the last job I had in corporate, I remember I did go into an office every day at that time, and I remember having one-on-ones with my boss. She sat right beside me, but yet I still had regular weekly one-on-ones with my boss, and I remember going in there one time just saying, “Ellen, I’m really overwhelmed right now. I have a lot on my plate,” which of course, she had no idea because she’s just like, “Nicole, go own your role.” I had a lot of autonomy, a lot of creative license to do things, which was great, but I was like, “I’m feeling really overwhelmed. Can we spend a few minutes just kind of white-boarding out everything that I’m doing and reprioritizing?” She was like, “Yeah, absolutely!”

So we spent just maybe ten minutes of that meeting that day just kind of letting her know what all I was working on and then getting her perspective on what she thought I should be spending the most time on, given her review as the head of HR.

Mistakes Nicole Sees in One-on-ones – 18:09

Kelly Nolan: I love it. I love it. So we’ve touched on some of them, I imagine, but what are some of the mistakes that you see, whether it’s managers or individual contributors making when it comes to these one-on-ones?

Nicole Case: Yeah, absolutely. Because I definitely can see that people have misconceptions about what this means or when they’re useful. The first thing that I think people make a mistake about, both managers and employees, is using it only as a status meeting. Yes, let’s spend some time talking through what you’re working on. “How’s that project going? How was that client call?” But I think that’s a different mindset on just kind of checking in to see how you’re feeling, seeing how you’re doing, seeing how things are progressing, versus, “Let’s talk about status. Let’s talk about updates.”

First of all, I hate status meetings. I think just in general those are a giant waste of time. We can give status in a whole host of other asynchronous ways that does not require everyone getting into a room somewhere to talk about that. So only seeing it as a status meeting I think is a giant mistake.

The other thing I see some leaders doing is not treating it as sacred and not treating it as a number one priority to them. So canceling it regularly, moving it around. Again, sometimes things happen, and we need to shift some things around, but if you set the expectation with your employee that, “These meetings are important to me. I’m not canceling this. I’m not allowing other things to get scheduled over it. This is important to me,” that sends a really clear message to your team about, “It’s important to me to spend dedicated time with you. We only have so many hours in the week to devote, and I want to devote this time to you personally.” That really sends a big message.

I remember one time I was supporting an executive vice president. I think he had 2,000 people kind of under his purview, and even his direct reports (and he had a lot of direct reports – he had SVPs and VPs reporting to him), he still said, “These meetings are sacred and are important.” He did not move them unless he absolutely needed to, and he always made sure they were rescheduled, so no matter what level you are, these meetings are still valuable and useful for you as a leader.

Kelly Nolan: And I would add that it really benefits you as a leader to do that because, so often, the women I work with are struggling with people who constantly interrupt them.

Nicole Case: Yeah.

Kelly Nolan: And so, if you set the expectation of, “Please hold any question that can wait, that is not a burning fire, for these standing meetings, then we will deal with them,” but that doesn’t work if you keep canceling the meeting because then they can’t trust that the meeting will happen, so they come to you with the burning question. So I really think it benefits everybody, and it’s something that I really experienced as an attorney at my second law firm. We technically had this standing meeting-type thing, but it was always canceled on me, so I felt like I was always chasing this partner down. It didn’t benefit either one of us. I could tell I was annoying him, but I was like, “You keep canceling on me, and I need these questions answered.”

Nicole Case: Yeah.

Kelly Nolan: And so, I just think it benefits everybody if you honor it because I think it will free up the rest of your — it’s kind of corralling all those questions, and then the rest of your time is freed up from those interruptions.

Nicole Case: Totally. Yeah, absolutely. And so, that’s another thing that another mistake actually is I think people don’t prepare for these meetings because they are regular. And I definitely recommend having a loose agenda. I don’t recommend having such a rigid sort of approach to these meetings. However, there’s still a level of prep that should be going into this, both on the manager side and the employee side to make sure that they’re going into this meeting making sure that they’re covering the topics that they want to talk about that week. Some weeks, you might have a fuller agenda than others, and some weeks might be super business topic-heavy, and other weeks might be more personal-heavy, just getting to know each other, talking about your families, what you’re doing over the weekend, it just kind of depends sometimes.

So by not being prepared, I think that’s another mistake that leaders and individual contributors can make going into these meetings.  

Shared Agendas – 22:28

Kelly Nolan: Do you recommend a shared agenda in that case, or how do you handle that? Sorry, I know I’m kind of moving you off what you were talking about, but when we’re talking about that preparation, I could not agree with you more about kind of corralling, having the individual contributor corral those questions, whether it’s in some sort of document or in a calendar entry, which I love. However you do it, do you then recommend sending those questions to the boss? Do you recommend just running through them in the meeting? It might just depend on the boss, too, whether they’re gonna read it or not.

Nicole Case: Yeah, I definitely think that there is gonna be an element of what’s everybody’s personal preference, right?

Kelly Nolan: Yeah.

Nicole Case: I talk to my clients a lot about giving your boss a heads up about what you’re going to talk about. So if you’re gonna walk into a meeting saying, “Hey, listen, I want to talk about the fact that I’m looking for a raise this year, or the fact that I’m looking for a promotion this year.” That’s probably not something to spring on someone. Or maybe you’re looking for feedback about something. People a lot of times don’t like to be caught off guard with those types of questions. So I usually guide people to send an email just to say, “Hey, by the way, in this week’s one-on-one I want to talk about the opportunity for a promotion for me,” or whatever it is that you want to talk about.

But you two kind of figure out what is gonna work best for each of you, but some really great ideas, Kelly like you said, maybe you keep all of your agenda items in the meeting invite, and you just update that meeting invite each week. I have a template that I provide to people that people can type right into this template and keep track of things that way. I had some leaders at companies, which I think probably the most efficient way is just truly to have a shared document of some kind that you can keep updating, and it just kind of keeps — and there’s a record of what you all talked about, any action items that maybe came out of that meeting, and it’s dated so that, as a leader and an employee, maybe during, say, performance-review time, you can go back and quickly kind of scan through your meeting notes from the last couple of months and be like, “Yeah, we talked about these things.” Like we said earlier, if you’ve got questions or need an answer about something or want to talk through something, instead of just barging into your boss’s office the moment that thought comes to you, if you just add it to the shared doc, right, then we can all make sure we spend some time looking at it, a little time before the meeting, and we can all be like, “Oh, yeah, I don’t want to forget that point. So I had already put that on there two days ago to make sure that we don’t forget to talk about this particular item.” But I do think that if you’ve never done these before, there’s an element of experimentation you just kind of have to be okay with.

I remember I was doing some leadership training with an organization a couple months ago, and this was one of the topics we talked about, and I shared with them about doing these regular one-on-ones, and this was a completely new concept for this organization, and this was a training. I kept coming back week after week for a couple of weeks. I remember coming back the very first week after we had talked about this, and some people said, “I tried this whole one-on-one thing with my team, and at first they all thought they were in trouble.” [Laughs] I said, “Yeah, if you’ve never done this before, people might think, ‘Oh, man, I’m in trouble. They’re trying to keep a close eye on me,’ or whatever, and you’re just gonna have to experiment with the cadence and the timing, the time of the week, the day of the week, how you’re keeping track of notes. You’ll just have to experiment with that and just be okay with it and just be open to trying out different things until you find what works for you and for your team.”

Nicole’s Recommendations for Starting One-On-One Meetings – 26:11

Kelly Nolan: I love it. I love it. So turning to the strategies that can help recovering mistakes. What can people do well in that affirmative way? Let’s say, as you’re saying, they’re like, “I’m gonna start this,” or “I’ve kind of been doing it, but I’m hobbling along, and now I’d like to come up with a system.” How do you recommend going about that?

Nicole Case: Yeah, I think at first, again, if this is something new for you or if you’ve just not been doing it really great up until now or really kind of sporadically, I would just let your team know ahead of time, “Hey, listen, I want to try this technique,” or “I want to try this one-on-one meeting. This is what the purpose is going to be. This is the cadence or how I think we should approach this.” So I think, again, just letting people know up front, “Hey, we’re gonna try this and see how it goes,” just so people, again, don’t panic and are like, “Oh, my gosh, I’m in trouble!”

Then the next thing is I think really, really effective one-on-ones — also, it’s important to make sure that you are in a place and it’s a time of the day where you can be truly present, right? So I had a leader one time who we would do regular one-on-ones every week, but he would sit on his phone the entire time and scroll on his phone the entire time.

Kelly Nolan: Ugh.

Nicole Case:  I mean, maybe he was listening to me. But I can tell you it didn’t feel like he was listening to me, and I felt like, “Oh, my gosh. I’m such a waste of time for him.” So my insecurities were coming out in all of that.

Kelly Nolan: Unproductive for the whole trust thing. [Laughs]

Nicole Case: Right. Exactly. Completely not a great way to build trust and rapport, right? So this is making sure that wherever you are or whatever time of day it is, you’re able to be fully present in this meeting with your employee.

I had a manager one time, she was in California, and so, she would call me on her way into the office, and that was our way of chatting. She had a long commute. And so, for her, that worked for her. I felt it worked for me too. Now, I can tell you on my end, I personally could not drive and talk to someone at the same time. I personally could not do that. But she could! That worked for her, and that worked for us. So that’s how we had our one-on-ones every week – on Tuesday mornings, when she was driving into the office in California during her long commute.

So, again, just making sure that you’re in a place that you’re able to be fully present. I don’t personally like to be at coffee shops or places where people can overhear. Again, this is a sacred meeting. This is a time where people are probably gonna bring you things that should be kept confidential. This is the opportunity for people to disclose to you that, hey, maybe something’s going on at home or they’re struggling with this relationship with another person on the team or whatever. So you want to make sure that you’re in a place where you can keep that confidentiality and that the employee feels comfortable about sharing, right? That you’re not being distracted. You don’t have other people walking by or who can hear you or anything like that.

Employee Takes Control – 29:12

Then, again, really successful one-on-ones also not only do they include business like, “How are things going? What is it that you’re working on?” The employee themselves are making sure that they are highlighting, not just the tasks that they’ve done because, again, that’s a different type of meeting in my opinion or a different type of document, I guess. They’re talking about the value that they’re bringing to the table, right? So this is a great opportunity, as an employee, to make sure you are highlighting not just the tasks, not just the meetings that you’re in but, “This is the value that I’m bringing. This is why me attending that client meeting was so successful. This is why putting this new system in place is useful for the whole team.” All of those things, let’s talk about the value that you’re bringing and raising visibility to what it is that you’re working on.

Same thing with your team. If you’re a manager yourself, and you should be having these meetings with your own manager, this is a time to also highlight your own team, right? Not just yourself, but also your team to say, “This is what my team’s working on.” So it’s almost like you’re floating that information up. You have one-on-ones with your own team, and then you’re floating that information up to your next line leader, so that your team’s getting visibility with them as well. This is also a really great opportunity to share any lessons that you’ve learned. Maybe you did make a mistake, or maybe something didn’t go as well as you’d thought. This is the time to talk about it and just to kind of do a debrief to say, “Hey, that project didn’t go very well, but this is what I learned,” to kind of show that you didn’t take anything away from that experience.

That’s your opportunity to ask questions, both as from the manager and the employee. You can ask the employee questions about what they’re thinking, their perspective. And then you can ask your boss questions about their perspective on different things going on in the organization in order to ensure that information is trickling down in the way that it needs to.

Kelly Nolan: Absolutely, and I think a lot of that highlights that need, especially on the individual contributor’s side or a manager who’s reporting up in those one-on-ones, of that prep work, and I’ll just throw out from where my brain goes from a time-management standpoint, for the person listening, is obviously the time for the one-on-one is blocked on your calendar, but also be blocking at a cadence that makes sense, with time to prepare to gather documents. If you do email the person anything ahead of time, when you’re going to do that. All of these things go into a successful meeting, and we want to make sure that, one, it’s not just up to your brain to remind you to do all of those things, and also that you’re protecting time to do that.

So just throwing that out there for whoever is listening. If you’re thinking, “When am I supposed to be doing this stuff,” it does take time. And so, just really making sure we’re protecting time to do that because I think that is how you make a valuable meeting come out of this.

How Long Are These One-On-One Meetings? – 32:16

Nicole, one question before you keep going. How long are these meetings typically?

Nicole Case: Yeah, so again, this is another place where you might need to experiment.

Kelly Nolan: Yep. I imagine it has an impact.

Nicole Case: Totally. Yeah, so some people, this might be a weekly 30-minute meeting. This might be a biweekly one-hour meeting. I can tell you that when I had a team that was also spread out, I had employees who sat in my office right next to me, and I had employees who sat in different offices, and my more experienced employee, I remember she sat in the Philadelphia office, we connected once a week outside of we had a broader team meeting that we had, and then we had a one-hour one-on-one each week.

But then I had another employee who was a little bit earlier in her career, and I asked her, “What’s the cadence?” Some of this you might ask your employee. Again, the purpose is this meeting is for them, so ask them, “What is it that you’re looking for?” She was like, “Nicole, we need to talk twice a week.” Okay, so that’s what we did. So Tuesdays and Thursdays, we met for an hour and talked through things.

The other thing was she was the only HR person at her site. She was kind of on an island by herself. So that made sense for us to have two hours, basically, every week where we connected one-on-one, and that made sense. As time went on, we didn’t always need the second check in. Again, this is a place where you’re gonna have to experiment a little bit. Again, there was a group that I supported, managers had 20/25 employees. Every Friday was their one-on-one day, and they had 30-minute blocks for their employees, but they could only get to everybody once a month.

Kelly Nolan: Yeah.

Nicole Case: When you’ve got 20/25 employees, that makes sense, right? But also knowing that if they needed them another time during the week, there were other ways for them to connect and time for them to connect if they needed additional time. So again, this is not gonna be the same for everyone, but I think, generally speaking, I’m like you need to spend at least 30 minutes once a week, and if it’s not that, it’s like an hour every other week is kind of what I think the sweet spot is.

Kelly Nolan: Yep.

Nicole Case: Again, where I see people get tripped up on this is they’re like, “Well, I sit right beside my employee. Well, my employee and I talk all the time,” and while that might be true, again, the purpose of this meeting is very specific and different than all of your other project meetings or just chatting in the break room or catching each other in the hallway or something like that. It’s different. We want to have that dedicated time where people feel like, “Okay, I can come in. I can talk about whatever it is that I want to talk about,” whether it’s business related, personal related, career related, and just trust that that time is going to be there so that if I do have things that I want to hold onto for that meeting, I trust that it’s going to be there and it’s gonna happen so that I don’t have to worry about chasing you around.

Kelly Nolan: Yeah, that makes a lot of sense. I feel like I interrupted you. Do you want to go through any more strategies on how to make these most effective?

Final Tips for Effective One-On-Ones – 35:28

Nicole Case: So final tips for having an effective one-on-one, again, we’ve talked about a lot of this already, but regular one-on-ones, again, are regular, regularly recurring, and they are rarely canceled or moved. You have some sort of an agenda. We keep it light. We keep it loose. But there is a purpose to every conversation. There are topics that we’re both coming into the conversation with. Again, we have to be fully present in these meetings, both as the employee and as the manager making sure that we are taking these meetings seriously and we’re ensuring that we’re fully present to the conversation.

I would say the final thing here is just making sure that we’re both following up on any actions. So anything that comes out of these conversations, anything that comes out of these meetings, we’re making sure that we’re closing the loop, whether it’s in the next meeting — you know, we come back to the next meeting and say, “Hey, I had that conversation with my boss, and this is what we talked about, and this is what we decided,” or “Can you share an update on that client meeting you had?” Whatever it is, right?

I think that’s a big complaint that I’ll hear from clients and hear from others is just that,
Well, I talked to my boss about it, but I don’t know whatever happened to it, I don’t know whatever happened there.” So making sure that we’re following up on any actions that we had committed to. Again, this is where a great kind of running combined/shared document can really help with those things too.

Kelly Nolan: Absolutely, and I can totally see as a manager, if someone’s listening to this in that position of, “I have 20 direct reports, and how am I gonna juggle all of this papering?” is really letting the individual contributor run with that. They can own the document, or if you don’t have a running document, they can be in charge of sending you a recap email. What I would say is for either of those things, communicate very clearly, in my opinion — it depends on culture — that they can be pretty quick and dirty, typos are welcome. It’s not polished. You’re saying to your own team, “Please don’t spend 30 minutes making this a beautiful document. It can be rough and dirty, but it just captures where we are and what we’ve discussed,” and I think that can hopefully take some of the burden off of these managers who are overseeing so many people.

Nicole Case: Yeah, 100%. I think, again, these meetings are for the employee. Therefore, put some responsibility on them to own these meetings and to own the agenda, to own the follow-ups, things like that. I think that’s absolutely appropriate, especially because you are only one person, and this is a great task to delegate out to your team, like, “Hey, these meetings are meant for you, for your growth, for your development, for your benefit. I need you to own the document. I need you to own the agenda, the follow-up emails, that kind of stuff.” I absolutely have leaders who just were super clear about that expectation, and that worked really well for them. 

Kelly Nolan: Awesome! Well, thank you so much for all of these practical tips. It’s an area that I certainly was in a lot of meetings as an attorney but didn’t have the training of what made them the most efficient, and so, I really, really appreciate it.

For the person listening who wants to learn more about what you do, Nicole, where can they find you?

Nicole Case: Yeah, absolutely! So you can find me on LinkedIn just at Nicole Case. I’m really active out there. You can also find me on Instagram. But I also have created a template for you all around having really effective one-on-ones. 

Kelly Nolan: Awesome!

Nicole Case: And this can be used both as the employee and the manager. So if you want to go out to www.theupgradedcareer.com/meeting, you can find the free template right there.

Kelly Nolan: Awesome, and we’ll put all those links in the show notes, but I really appreciate you taking the time to be here, and for the person listening, thanks for being here as well, and I’ll catch you in the next episode!

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