Great One-On-Ones — Comp + Coffee: Ep. 22

We’ve said it before and we’ll say it again: solid communication can be the difference between a company that thrives and one that lags behind.

And we’re not just talking about company-wide communication.

For every aspect of an organization to thrive, managers and employees need to be on the same page.

That’s where one-on-one meetings come in.

On today’s episode of Comp + Coffee, the hosts are joined by Courtney Bigony, Director of People Science at 15Five.

They discuss:

  • Why should you hold one-on-one meetings, and what goals you should set for them
  • How to stay away from the status update one-on-ones
  • Why your first one-on-one with any manager or employee is different (and what to do about it)
  • How great one-on-ones can impact your team, department, and the business

And if you like what you hear, be sure to subscribe and give us a 5-star rating!


For a full transcript of the episode, see below.



Shawn: And we are live. Welcome, Bill.

Bill: Hello, Shawn. How are you doing?

Shawn: I’m excellent thank you. Another fun edition of Comp and Coffee but we have a special guest today and we are also missing a third of our normal crew.

Bill: Who is the special guest?

Shawn: Special guest is Courtney Bigony. Happy to have her. She is the Director of People Science at 15Five. Courtney, welcome.

Courtney: Thanks for having me.

Shawn: Unfortunately, we are missing Kaite today, our normal third wheel here. I call her the third wheel. Our normal third wheel she’ll be back next podcast recording. Excited to have you, Courtney, thanks for joining us today, this came up as a previous — Bill and I are famous for tangential discussions on a previous podcast and one of the things we talked about is, A, I don’t think many people conduct good one-on-ones and B. I think there is a really a strong advantage to people in competition specifically being able to better conduct one-on-ones with their employees, but more specifically for the focus today their bosses if they have [unintelligible 00:01:25] of a meeting even their boss’s boss right?

Courtney: Yes.

Shawn: I want to start basic can you give me your background Courtney, how you got into all of this you are at 15Five which is well known for one-on-ones are certainly part of it. Give me an overview of your background and of 15Five and-

Courtney: I am the director of People Science at 15Five and the most common question I get is, “What does that mean?” One, 15Five we build leading performance management software and as the director of People Science, I make sure that our software and our product is backed by the latest psychological science. Our software has objectives, one-on-ones, check-ins, high fives for recognition. I’m looking at the latest psychological science what does the science show about leading organizations and then building that into our product. The one-on-one feature or check-in feature is core to our product so this is a great topic to talk about.

Shawn: Yes that’s actually quite fascinating we can probably dive into that for 10 minutes of itself.

Courtney: Yes [chuckles].

Bill: What does 15Five mean?

Courtney: 15Five? It’s actually inspired by Yvon Chouinard who is the founder of Patagonia. His employees spend 15 minutes every week completing a weekly check-in that managers can review in five minutes to stay up to date with their employees. So people can grow and develop in their companies and become their best selves in 15 minutes a week with 15Five.

Shawn: Yes, I think it was the CEO of Patagonia’s goal to continue to live his mission to test their products so he’d be out on mountain tops in, I don’t know Chile or Argentina-

Bill: Patagonia?

Shawn: Patagonia and wanted to be able to keep up with what was going on back with his teams, so he had them assemble quick ball less– Does that sound right Courtney?

Courtney: Yes that’s exactly right, he wanted to run a company and have a life and that’s what we’re building at 15Five, employees can do amazing work and also have a life and so can managers and that rolls up to the CEO and the founders.

Shawn: And you are hiring?

Courtney: Yes we are hiring.


Shawn: [unintelligible 00:03:37] plug all the time. Let me ask you before we dive deeply into this today, how common, like across the spectrum, how common are one-to-one meetings do you think?

Courtney: I think that one-on-ones it’s something that people know is important in an organization but I don’t think that they are done well. So I think they are pretty common people have regular meetings but I don’t know how good they are and the quality is what really matters.

Shawn: Talk more about that, I mean, you hear a lot that perfect world perhaps a one-on-one meeting should not be about what their tasks are, for example, that we go what you’re working on necessarily. What do you mean when you say they are not done well? Is it that aspect or there are other things too?

Courtney: Yes, I think that’s a big part of it that most of the time people spend their really meaningful one-on-one in person or even at the job or a call time focusing on status updates and instead they should really be focusing on priorities.

Bill: That makes sense, I think a lot of times you see these one-on-one meetings are people going through the motions or they are told to or know they should have one-on-ones and then the information stops there so it’s like you and I and Shawn should have a one-on-one it’s like okay we meet but we don’t know what the point is or what we’re trying to do until you default to the easy, comfortable thing of let’s just talk about what’s on my To Do list and what’s on your To Do list.

Shawn: When you say priorities Courtney does that mean the big high-level things of well, what you want to do with your career and how can we help you get there or here is the priorities for the department that have recently changed or here is what we’re mapping through this year? How is that affecting what you do? How does that really come to life that you’ve seen work well?

Courtney: Yes. Before we dive into the science of one-on-ones, it’s important to zoom out and take a higher level view of what is the ultimate goal of a manager in a company. Then that ultimate goal is going to funnel through there that real-time feedback that one-on-ones there. They review conversations. The ultimate goal of a manager is to really unlock employees’ potential. We’re seeing this shift in the workplace from this performance only mindset where it’s about just getting out the goals and getting out of performance out of employees.

We’re shifting to this people potential mindset where the performance will be just a natural result both performance and engagement. The ultimate goal of a manager is to really understand what makes your people come alive and then find ways to channel that aliveness productively towards the company goals. That’s this larger shift that we’re seeing in the workplace and it’s trickling down into how the best one-on-ones are handled in the world of work.

Going on that new framework that we’re working towards I can dive into the science of one-on-ones and what a really effective one-on-one looks like. The literature that I’m pulling from is a positive organizational scholarship and that’s the science of driving workplaces. That research is coming out of the University of Michigan and they are amazing. When you talk about effective one-on-ones and really unlocking the potential of your people at work really understanding what it means for people to be their best selves in the workplace.

The first thing is I just want to highlight something that people don’t really get is that regular one-on-ones are made up of two parts.

According to science, there is this first one-time kickoff meeting. It’s one hour to 90-minute meeting that happens right when an employee joins an organization or say an employee is joining a new team. Just at the start of the relationship. The goal is clarity. Most people just dive into creating regular one-on-ones, their regular check-ins, but they don’t have this really important one-time kickoff meeting. There are a couple of key things to talk about in this kickoff meeting. Again, the goal of this is clarity. To really get clear on the things that aren’t made explicit.

The first piece is to look at the job description. The job description will have key pieces of an employee’s role but it’s incomplete. The first thing to do like your first check and your first one-on-one with the employee is to review the job description and fill it in with what actually happens on the job. This is important because only 50% of employees know what’s expected of them at work and when this number increases performance increases. It’s a really basic foundation.

Then the second piece of that initial meeting is to go over the rewards and the comp structure. Q And pay factors and then the career ladders. This conversation shouldn’t happen during the first the first performance review. It should happen at the first day or during the first week that someone enters the job. They need to be clear about what are the financial and non-financial incentives of the company and then how can they grow and develop in that company. What are the career ladders? That would be the first one-on-one.

Then lastly Adam Grant he’s at Wharton. He talks about having an entry interview during this initial kickoff meeting. It’s really important to do this and to just understand your employee, understand what their top strengths are, what their favorite types of projects are so you can really discover what it takes for them to do their best work.

Then you go into the recurring one-on-ones. I just want to highlight that initial kickoff meeting that’s so important that most people don’t even do.

Bill: It makes a ton of sense. Come to a couple of things in there, but it makes sense the first goal which you’re right. I do want to explore maybe one of the things you said is that the job description tends to be incomplete. This is an area that heavily overlaps with the– what we talk about which– what does the research say around that? Is that is it that way because priorities change? Is it that way because there’s always nuance to what might be at the top level jobs usually but not really how it applies day-to-day?

Courtney: Yes. I would say all of the above. The job descriptions that we’re pulling from I usually the ones in the ATF system. On the website, on your job boards so it’s poop. That job description from your job board and add it into the one-on-one as a starting point. Most people don’t even do that and then fill it in. That’s based off of the priorities of the organization. The unique strengths of the individual and the nuances of the role which are generally not accounted for.

Bill: Right. That’s interesting that it’s both job-related and person-related.

Courtney: Yes, totally.

Bill: It’s another one of the weaknesses of the whole job description world of managing and maintaining and keeping them up to date and keeping them relevant.

Courtney: Right.

Shawn: Also then too I think the key thing that I’d be surprised if most people are clear on this so it’s a good thing to cover early as well is, what are the goals not just for hopefully the department that you’re in but specifically for you? How do we get aligned around those and how do we help you make decisions between both the goals of department slash organization and where the company as a whole is trying to go?

Bill: Ready to [crosstalk] setting and clarity all at once.

Shawn: Name, its goals clarity goal.

Bill: Day one.

Courtney: Exactly.

Shawn: That makes sense. Let’s jump into that though then these regularly recurring one-on-ones, how do you really make them truly effective? A personal example I’ll share before I used 15Five so we’re going back quite some time now. Was my boss at the time a CEO would come to the meeting with, “Well, here’s the things I want to talk to you about or you want to talk to me about. We cross come here in the beginning the meeting,” and then just start to dive in. That’s gone. There’s definitely things that would be nice to have context on before walking into that as well as to your point maybe not just be deep in tasks all the time. How do you prepare for an effective one-on-one meeting and a lot of nuance to that too? How do you prepare for an effective one to one meeting when you want to manage up?

Courtney: Right. First I’ll dive into what the research shows should be included in every one-on-one meeting and then I can dive in it to how to prepare for those meetings. After you have that initial kickoff meeting, that one hour to 90-minute one, you’re going to want to schedule regular recurring meetings. That provides a sense of safety that they know that they’re going to regularly check in with their managers after that initial kickoff meeting. The research shows at least once a month minimum if not every two weeks, let’s say two hours every month but that should be customized to the person in the role. Then some key things to talk about in that one-on-one every time, these should be like recurring topics would be number one goals and objectives just like you talked about. People should be really clear on their individual objectives and also really clear on the company objectives and how those two align.

Then it’s also a place for managers to really give context and to what’s happening with a company that’ll impact their employees individual objectives. The second part of that individual objectives pieces are there any skills gaps that’s going to impact them executing on their work? To identify any learning goals. Number one thing on the agenda, goals, and objectives both the individual and the company. Then the second piece I’d have on every one-on-one agenda is wins and challenges. People need to make progress on meaningful work. It’s important that employees are recognized for wins so they’re really recognized for good work and that managers shine a spotlight on that.

Secondly, they need a place to address any roadblocks or challenges that are getting in their way and a regular place to do this which is where the one-on-one is really helpful. The point here is to really release any tremors before they become quakes. That’s why I like to think about it when it comes to the world of work. It’s also a place when you’re covering the wins really what went well the challenges, what roadblocks are you are you facing into a place for feedback as well for managers to provide feedback and managers should also request feedback from their direct reports about what they could be doing better.

Lastly, in addition to the goals and objectives, the wins and challenges, I would also create a space for the personal stuff. Anything interpersonally that’s happening at work, these things are bound to happen to bring them up early and often. Also, some things happening at home that may be getting in the way of their work. It should be a safe space to bring this up and if it’s something pressing, then just bring that to that to the beginning of the agenda. Those are the three themes that I would add in to every recurring one-on-one, goals and objectives, wins and challenges, anything personal as the key topics.

Then in terms of your second question, how do you prepare ahead, so not to plug 15five. I don’t know how other companies do this. Most companies use Google Docs, but I’m not sure how they make it incredibly effective. The key in terms of planning ahead is in 15five, we actually have the regular check-ins or the weekly check-in, where you’re really going over those key pieces that you submit to your manager. That’s where you get rid of the status update part. They’re privy to what you’re doing on a weekly basis and what’s going on. Then both people really add key items and key priorities to the one-on-one agenda, both the employee and the manager.

When you sit down for that in person or video conversation every two weeks or at least once a month, you have all those key priorities to talk about. It’s the ultimate way to plan ahead weekly check-ins and then pull those priorities into a one-on-one agenda, that you prioritize and focus on when you’re actually face-to-face in present with each other.

Bill: Say these haven’t regularly get the [unintelligible 00:16:17] about, it needs to be customized to the individual. What do you see as the effect on an organization if managers can hold these regularly, whatever [unintelligible 00:16:27] make sense and do it well?

Courtney: That’s a great question. I’m going to pull from Gallup stats, and then also what the academic literature shows. Gallup shows that managers account for 70% of engagement. 70% is a really high number. Also that employees are three times more likely to be engaged when their managers hold regular one-on-one meetings with them, so it has a huge impact on engagement.

Then the academic literature shows that it not only increases engagement but then also performance. They actually did a study with two groups and one group had regular one-on-ones, and the performance increased with those one-on-ones. Then the other group when they dropped their regular one-on-ones performance immediately decreased.

That’s a really amazing study called the Personal Management Interview as an Intervention by Wayne Boss from CU Boulder. He shows that regular one-on-ones impact engagement and then productivity and goal accomplishment. It does have a huge business impact.

Bill: Were there any thoughts as to why that might happen?

Courtney: While you’re not checking in with your folks. One, people don’t know what people are doing and they’re not removing roadblocks, and they’re not understanding wins. They’re not helping their people make progress on work. Just such a big piece.

Bill: I imagine there’s no accountability. People feel like they’re being supported, being-

Shawn: Recognized.

Bill: – recognized, that they’re able to talk about what they’re doing, and getting their bosses buy-in, and general communication. You see that the value of communication is huge to the efficiency and effectiveness of companies.

Courtney: Totally.

Shawn: If you are measuring that role that’s trying to get the best out of your employees, what are some good questions to ask to start that dialogue? You give us the cover goals and objectives managers should give context as to what’s going on the organization, decisions that are being made, work on skills, gaps, wins and challenges at the recognition part, what requesting feedback. What are good questions to ask though, to prompt those discussions?

Courtney: First, I would just keep it personal and ask how people are feeling and just do a personal check-in. Then the structure of the one-on-one will actually naturally occur because of the priorities that are already in the agenda. Those questions that I went over earlier like the goals and objectives, the wins and challenges, and the personal piece, those should already be in that check-in. Then the priorities are what you talk about.

I don’t know if I would recommend an exact list of questions to be talked about in every single one-on-one because those are really going to be determined by that regular check-in, and what the priorities that are pulled from there. It’s really just focusing on those priorities that are agreed upon and added by both the manager and employee. One thing I do want to touch on out of the research that is important since we’ve really talked about the content and what to talk about during the one-on-one, what most people don’t look at, and I love highlighting what the research shows where there’s a gap in actual practice, is it’s not only what you talk about, it’s how you show up as a manager and then also as an employee.

This is so commonly ignored. It’s called relational energy and the literature, but what it shows is that positive energizers. There’s lots of positive energizers in an organization and these are people who have a lot of high energy. They’re supportive. They bring vitality to their people, are the top performers. These managers are the top performers and also their team members are high performers as well. What the research shows is that high performing organizations have three times more positive energizers than low performing organizations.

Again, we talked about that content piece, what to talk about during your one-on-one, goals and objectives and everything and top priorities. How you show up is the second piece that I don’t think a lot of people are addressing that I think makes a big difference between the highly effective one-on-ones that are really unlocking your people’s potential. What does a positive energizer mean because it can be a big term and topic that can seem vague? I think of it as how you show up. This is not like a superficial charisma or like a false extraversion. It’s really about connecting with your people as people. What is the tone and the form of the conversation? How do people feel when they walk away from it and during the conversation? Managers, as they’re going through these priorities and as they’re going through the main topics, they really need to make people feel that they matter.

There’s a healthy amount of optimism in the conversation, people are present and they’re attentive. As a manager, you’re not on your phone or your head’s not somewhere else, you are there and you are focused with your people. You’re reliable. You don’t move your one-on-ones a lot. They could be a poor signal to employees, so always keeping your one-on-ones as a manager when you’re having these conversations you’re really open to new ideas.

You’re highlighting strengths and you’re spotting strengths and your people are expressing gratitude. Again, that goes into the celebrating wins piece. I just want to highlight that it’s not just what you talked about it’s also how you show up and the energy that occurs in the meeting which actually has an impact on performance.

Shawn: That makes sense. I find doing my one-on-ones, for the most part, I actually look forward to them and if I don’t that says something else, right?

Courtney: Yes.

Shawn: I think they tend to be good conversations. To the point that you made earlier, if you can get everybody aligned and motivate, that’s a pretty good role to play as a manager as opposed to taskmaster.

Courtney: Right. Exactly. People should walk away from their one-on-ones feeling really clear about what they’re doing and if they are experiencing roadblocks or issues clear about next steps. Also really vital and energized like, do you walk away feeling energized from your meetings both the manager and employee? I think that’s a really good barometer.

Shawn: This is more of a curiosity question and I’m asking this generally probably to both you and Bill. Is the one-on-one more of a modern construct as far as we know or have these always been happening but maybe just never called it?

Bill: That’s an interesting question. In my career, I’ve had things like one-on-ones the whole time but I don’t remember the first time it was planned, organized and labeled one-on-one.

Courtney: Right.

Shawn: You go to a meeting with your manager but-

Bill: Right. In the early days when you’re a pup fresh out of college, it’s like every day is a one-on-one with your manager because your back and forth constantly with what do I do next or how do I do it? I don’t know. Courtney, do you have any history on the one-on-one?

Courtney: Yes. I think this is a fascinating question and in order to answer it, I’d have to zoom out a little bit. What we’re talking about is communication and communication is a construct. We make constructs real in how we operationalize these things. Communication again is a really big fluffy term that feels distant and hard to grasp especially good communication.

We can make these things real with how we operationalize that. One-on-ones having a regular meeting is one way to operationalize really effective communication. Same thing with a recognition program. Recognition as a form of communication. If you have a program, it operationalizes it. To answer your question I think that we’ve always had communication, but I think it is in the recent years that we’re really operationalizing it with one-on-ones. I don’t think we’ve done it very well because we’re actually just learning about the importance of one-on-ones. I think Wayne Boss’ research goes back to 1983 so I think it’s fairly recent. Now we’re learning how to do those things well and we’re operationalizing it with technology and practices like a regular one-on-one meeting and then also training those pieces that cannot done in technology like that relational piece, that relational energy is important to train on.

Bill: Although I think back to your question, Shawn, if you deconstruct it, to use Courtney’s term, and go back to early days in my career, the keys to the one-on-one are open dialogue with your manager, the safe zone where you can talk about whatever you need to talk about, building the rapport and having that dialogue about what’s important, what you need help with, what’s going on at work, at home, whatever having that. All those things existed with the good strong manager-employee relationships.

That people were doing that all along and then I think somewhere along the line, people start to realize that those people were doing it well, what are they doing? It eventually becomes systematized. It becomes a thing, to use a Shaw term.

Shawn: It’s my term? That makes sense. I wonder too if the free agency aspect, for lack of a better way to describe it, also plays into that when it’s not guarantee– That makes 100% what you just said the people who are the best managers, who are the best teams, who are consistently performing over performing would do those things. Secondly, though I wonder there’s more free agents as people started to move jobs more often came into play, did these become more important because you’re– One of the biggest drivers of engagement I agree with this is your relationship with your manager. Well, you’re going to go find a good relationship with a manager.

Bill: Accelerate it. Make it happen better, faster.

Shawn: Just interesting trends that convert–

Bill: I also think back to bad manager relationships where you don’t feel like you can disclose the real problem to your manager or the real story or real [unintelligible 00:26:57] hear that this person isn’t easy to work with. That’s the opposite. The non-one-on-one, the non-effective communication.

Shawn: Zero on one?

Bill: Zero on one. [laughs]

Shawn: Courtney, is there anything in terms of a team size that comes into play here too? Because as these things are becoming more important, is there any of the research that you’ve seen, an upper threshold of what an effective manager can effectively manage? Not to use redundant or duplicate terms there.

Courtney: That’s a great question. It’s really important. This is drawing on Richard Hackman’s research on teams. He’s from Harvard. He says that there is an ideal team size. An ideal team size is 4-6, no more than 10 people. Once you go above 10 people, interpersonal friction, and then performance issues increase. I just think with team size because it absolutely does have an impact on your communication and how effective you can be as a leader, is to just keep it in the single digits.

Shawn: That takes into account how many direct reports correct? Like if you have a team of 60, but there’s layers upon layers, that’s not what we’re talking about here.

Courtney: Yes, direct reports.

Bill: It’s like the recipe for good dialogue, or I’m going to get laughed at for this one. It’s like how big should a good dinner party be? 6-10.

Shawn: Makes 100% sense. Otherwise, you’re divided in different conversations.

Bill: Exactly. You lose contact with everybody and it becomes less intimate more superficial.

Courtney: The science for effective– If we’re talking about dinner conversations, science for effective or the right amount of people is about four.

Bill: Four?

Shawn: Wow, I guess that makes sense too. That way everybody’s engaged and you don’t have that– Some people will feel left, some people will look to the right, some people are tuning out, is that?

Courtney: Yes.

Shawn: Interesting.

Bill: I’m probably doing all of those things. [laughs]

Shawn: At a given time though. Courtney, I think that covers the time today.I think this applies, obviously, across the board within an organization, but our goal also is to help conversation become more strategic within an organization. I think this is one of those key levers on the way there as you’re having these meetings with your boss and your employees as well. This goes both ways.


Bill: Sorry, Courtney?

Courtney: I was agreeing just like you were.

Shawn: Bill, Courtney, both you? Anything else you’d like to leave us with today?

Courtney: No. I think we jam-packed so much information into 30 minutes. I think if anyone is interested in a resource on positive organizational scholarship and the science behind effective one-on-ones, I would highly recommend a book called Positive Leadership by Kim Cameron. He really outlines a lot of what I talked about and digs in more to other pieces of effective communication such as a resource for your listeners.

Shawn: Oh, no, definitely. I just wrote that down. I’ll take a look into it. One of the earlier podcasts we did that I think this one might have come up on was on what books did you read to better educate yourself, but become a better leader as well. I’ll take a look into that one. I have not yet read it so thank you for the recommendation.

Courtney: Of course.

Shawn: All right. Well, we greatly appreciate your time today.

Bill: Yes. Thank you.

Courtney: Yes. Thank you for having me.

Shawn: Pleasure to chat with you. Check out 15Five if you haven’t already. If you don’t use them, I highly recommend them personally. That’s not a plug. I literally have used them for years now.

Bill: That actually is a plug

Shawn: All right. It’s a plug, but I’m not getting paid for my plugs. I wish.

Bill: Okay. That’s fair.

Shawn: Courtney, can we talk about some modernization of this?


No. I highly recommend the software. It’s a great utility to use to better understand what’s going on with your team, and have better conversations when it does come time for those one-on-ones. Thank you. Hope to have you back on soon. I could talk about organizational dynamics, behavior science all day. I find it fascinating.

Courtney: I know. Me too. We’re off to continue the conversation.

Bill: That’d be great.

Shawn: All right. Courtney, thanks very much. We hope to have you back soon.

Courtney: Amazing. Thank you so much.

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