What to Ask in a Weekly Remote Team 1-on-1

In today’s episode, you’re going to discover what to say when you’re in a weekly one-on-one with someone you’re leading. Make sure you avoid death by meeting and leverage the time to maximize the benefits to you and the person you’re leading.

Now, I know you might be thinking, “But Eric, I don’t lead anyone. I don’t have a team.” Well, unless you have a board of directors, you need to be sitting down intentionally with yourself every week and going through the agenda and questions I’m about to share with you.

Welcome to the Eric Dingler Leadership Podcast, a show designed to help you lead better to live better. In today’s show, I’ve got three things for you. Number one, we’re going to walk through the weekly one-on-one, what it is, what it isn’t. And I’m going to share with you four of the eleven questions I rotate through asking in every weekly one-on-one, and I’m going to share with you how you can get all eleven of them if you’re interested. Number two, I’ve got a brand new resource I’m rolling out this week, and I’m excited to be unveiling it here on the podcast. And number three, I’ve got this week’s Leadership Tip of the Week. So make sure you stick around for all three.

Okay, so start by meeting with yourself if you don’t have a board. That’s what I said at the beginning, and I mean it. Now, why do you want to do this? Well, to do this, you have to understand the intention of the weekly one-on-one, the purpose. What you want is you want to avoid death by meeting. You see, meetings can make or break you and your team’s will to live. So meetings have to be very intentional. Every meeting should have a very specific purpose, and if the purpose of that meeting can be achieved as effectively or efficiently without a meeting, then don’t have the meeting. Solve it that way.

Meeting time should be very valuable. It should be maximized for maximum benefit. And the weekly one-on-one, what you’re wanting to do is this. I think there are three main benefits here. Number one, you’re going to get and keep a pulse of your team. This is really going to help you start to gauge the impact of your company’s culture, and we know that culture trumps vision. So to make sure you’re on pace to reach your goals, you need to be having regular, consistent check-ins.

Now, these check-ins aren’t on specific tasks. They’re not project management meetings. If you have to have a meeting to ensure projects are happening, that should be a project management meeting, because one day you should be able to hand that off to somebody else. But the weekly one-on-one where you’re meeting with the people you’re leading is something you’re never going to give away, because it’s so valuable when done right. If you walk out of a weekly one-on-one and you think it was a waste of time, you’re not doing it right. So do it better.

And how do you do that with intentionality? You do it by having a plan, having an agenda that works. See, a lot of times people go into their one-on-ones and they show up ill-prepared, so they just start talking about the easiest thing there is, which is the list of ongoing projects. Where do we stand on this? Where do we stand on this? And then they’ll give an update. Both of those things are a total, complete waste of time for a weekly one-on-one. That stuff could all be communicated to a group and processed by a group. It could be done with asynchronous video. It could be done through email. There are so many ways to manage this. We use a daily check-in on our project management system, and I’ve talked about that in previous episodes.

So that when you get into the weekly one-on-one, you’re focused on getting and keeping a pulse of the business. You are also going to figure out and know the things that you need to know that you can’t find looking somewhere else. This is information that’s not available through a dashboard, that’s not available through metrics, that can’t simply be emailed to you. This is stuff you need to know to be an effective leader, and you can’t find it anywhere else. And the other benefit of a well-designed weekly one-on-one is that it’s going to move your team toward a goal, and that goal is your vision. It’s going to make sure everybody’s heading in the right direction, focusing on the right things for the right reasons.

Now, what I don’t do in these meetings: I don’t use these meetings to upskill. I don’t use them to train. I don’t use these for project management. And I don’t use these to share updates. I could have just emailed about that. What I want to accomplish in these meetings is I want to reinforce the vision, mission, and core values by modeling them over saying them. I want to get a pulse of the morale of the company. Now, we ask about this in our weekly report, but the one-on-one lets me get that individual deep check-in where I can really interpret more than just the typed words. It lets me ask questions and probe further than I could from the weekly report. That’s what I mean by it helps me get a pulse of the morale and understand where people are.

The third thing I want to accomplish in these is I want to unearth any personnel issues early. If somebody’s not happy and they’re looking for a new job, I don’t want to be blindsided, because recruiting and hiring and onboarding the right fit takes time, and I don’t want to ever be put in a pressure situation that didn’t need to happen. So it really helps me unearth personnel issues very early, and normally resolve them before they even turn into something closely resembling somebody leaving the team. And it really also lets my team know that they are valuable. I can’t just tell my team they’re important. I can’t just tell them I appreciate them. I have to spend time letting them know.

Now, some of my team requires more time in their one-on-ones than others. We know this from their appreciation language. If you’ve been a long-time podcast listener, you’ve heard me talk about that, especially in this series we’re in right now where we’re answering the five most common questions asked about leading a remote team. So make sure you go back and listen to all of the episodes in this series, and you’re going to get that.

So what does it really look like? Well, for me, this is how it works, and I’ll let you take this and put it together however it looks right for you. At the top of everybody’s note, I keep a note in GoodNotes for everybody I’m leading a one-on-one for, and throughout the week, I can jot down ideas, things I want to bring up, whatever it is. It’s very easy for me to open up and look at these, and they’re quick and easy for me to access from my phone, from my computer, from my iPad, doesn’t matter.

At the very top of this document, I have the team member’s name. I also have their work anniversary date, so I know what day they started working for the company. If they’re married, I have their wedding anniversary. If they have any kids, I have their kids’ names written down and their kids’ birth dates. And I have the birth date of the team member. I have these things because I don’t naturally remember them, and I don’t have them in my calendar. I don’t use my calendar for that kind of stuff. These dates are important because they’re important to the person on my team, and this doesn’t take long.

I posted recently about this on LinkedIn, and somebody commented that a leader they know doesn’t have time to get into celebrating this because they have to do the one-on-ones on their lunch hour with very limited time. I get it. These one-on-ones are very limited. I only allow forty minutes for them, so I don’t have a ton of time for these meetings either. They’re not limitless. But it takes less than a minute to know, going into the meeting, that it’s one of my team member’s birthdays. So I can start with a question. “Hey, isn’t little Ryan’s birthday coming up soon? How old will he be? What does a twelve-year-old want for his birthday these days? Man, I’m so excited for you, I hope you guys have a good time celebrating.” That’s it.

Now the team member knows that I see them as a person, more than just a team member. They’re a human being. They have a family. They have kids. They have things that are important to them outside of the company, in addition to what we’re trying to accomplish through our digital marketing agency. So this doesn’t take time. “You’ve got a wedding anniversary next weekend, any plans? You guys going anywhere? Got anything special planned?” Just asking questions, hearing the answer. It doesn’t take five, ten minutes for this stuff. It’s quick, and it’s just a check-in. If there’s nothing there, then I don’t worry about it.

Then I jump right into question number two, and in my GoodNotes note it just says WOY: what’s on your mind? So I ask them, “What’s on your mind today that you want to make sure we talk about?” I want to make sure they get a chance to be heard right at the beginning, not at the very end, in the last five minutes, when we’ve got to cram some big giant thing into five minutes.

Asking “what’s on your mind” does a couple of things. When you ask it every single week, they learn to anticipate it. I just tell my team, “Hey, I’m going to be asking you this every single week, so please have a list.” Some of my team have an actual list, some don’t, it depends on personality types. But I just love asking this. We don’t talk about it yet, we just list them. It might be one thing, might be four things. Could be really small, could be huge. This question had more benefit to it than I anticipated when I started using it.

Then underneath that, I have a list of “what’s on my mind.” I’ll often say, “Okay, great, so you want to talk about these three things. I’ve got three things I want to talk about, and they are this, this, and this. Let’s start with this issue you brought up, then I want to talk about two of my three things, then I want to talk about your last two, and we’ll save this last one for the end.” I just reprioritize them right there on the go. From time to time, they’ll bring up something so big and important that we don’t get to anything else in the meeting, and that’s okay. Because your team members are important, and if you can’t see them that way, then you’re not a leader, and you should be ashamed of yourself.

And if you’ve got people above you who say, “Well, I don’t get enough time,” then lead up. Model this, demonstrate this. Let them know this is important. This is why we have high turnover. This is why people aren’t excited to recommend people they know, like, and trust when we’re hiring. We’ve got an unhealthy culture because we’re not treating our people well. It’s amazing how many personnel issues can be fixed with just this simple thing.

I used to run a summer camp, and I had all this staff and this team. The benefit was, every year we started over, not with all new team, there were several returning staff members. But when I look at how things were at the end of my fifteen years versus the beginning, my retention rate of staff was much higher, the satisfaction of my team was much higher, the quality of work they did was superior. They weren’t better people. I was a better leader. I was able to get more from them and help them have more joy and encouragement in doing the work, and they wanted to come back more often because they had a great time. They realized they were a part of something. A few things stuck, and this idea of “what’s on your mind” was one of them. It gives them so much freedom and adds value to them.

So first thing on the agenda, any big things coming up that I need to know about. Second, what’s on your mind. Third, here’s what’s on my mind, I reprioritize them and I tackle through those. Then I have a list of eleven questions that I rotate through. I grab one, put it on the meeting agenda, and ask it. The next week I go in and ask the next one, and so on. I mark in the document I use to store these, it’s a spreadsheet, down the left and across the top I have everybody’s name, and I put the date of the last time I asked them this question. It’s a real easy way for me to keep on track, because people are on different schedules with these since they were hired at different times. The order that you ask these in doesn’t matter, it’s just about the questions.

So I want to share four of these questions with you, and with each question I’ll tell you why I ask it.

Here’s one: What’s been energizing you about your work lately? What I’m looking to uncover here is what gives them life, so I can help them spend more time there. This is one way we start to find out how people’s interests are shifting and growing, because the things that give them energy change for some people, and never change for others. That just lets me know I need to keep giving them more of that, and not look further.

There are people who should never be promoted, because what they do, they love. Back at the summer camp, it was very common that the lowest-paid staff were the camp counselors, and the supervisors got paid more. The thing that bugged me about that was camp counselors eat all their meals with the kids, do all activities with the kids, sleep in the cabins with the kids, they’re on all day, all the time. Supervisors had a staff house to live in and had breaks away from the kids. But supervisors got paid more. That’s just how every summer camp in the organization did it.

Until one year I decided to make a change, because there was a returning staff member I wanted so desperately to stay as a counselor. She was a great counselor. I reached out and said, “Just wanted to confirm you’re coming back this summer as a counselor.” She said, “I want to come back, but I can’t come back as a counselor.” I asked why. She said, “I need to make more money this summer. I can’t afford to come back as a counselor.” That conversation was the moment I realized our entire pay structure was broken, and I changed it. I had camp counselors after that who made as much money or more than supervisors, because they were so good at their job, and it gave them energy, and they had no desire to be a supervisor. They didn’t need the title. They were there because they loved being a camp counselor, and I made the decision to reward them for it. We started an aggressive pay raise year after year for our counselors. We were often paying our counselors more than our supervisors, upside down versus the rest of the industry. Eventually I got to the point I didn’t base salary on your job title. It was the pay for this job, based on your experience and what you could bring to it. That might sound logical, but it’s not how summer camp works, and I don’t care how it works for you.

I want to know what’s energizing my team, because when you rotate through these questions once a quarter, most of the time they don’t even remember answering it before. “Oh geez, wow, that’s a good one,” and I’m thinking, I just asked you this three months ago. I track it. I keep notes on this, because some staff, it changes, and for some people on the team, it never changes. I don’t want to go to them and ask them to take on a promotion or a new role. I want to give them a raise. I want to keep them doing the thing that energizes them, because when you’re energized by it, you’re going to do your best at it.

Another question I like to ask is, what would you have done differently last week to improve the results you got? I love this question. This is one of the questions I ask myself on a fairly regular basis. I’ll sit down and ask myself what I accomplished last week, then ask what I would have done differently to improve my results. Say I had five things I wanted to do and only got three of them done. When I sit down and ask what I could have done differently to get all five done, suddenly I start to see places where I was wasting time and energy, where I wasn’t working efficiently, and the answers help me implement changes that make me better.

I can do the same exact thing with my team. A lot of times by the time I get to this question, I already have something specific in mind, or I’ll ask about a specific project. I might ask our director of web services, Peter, “Looking back on the Acme Bait website, what would you have done differently for us to have gotten that project done faster, or smoother?” I’m not saying it wasn’t done on time, or that it wasn’t smooth. I’m just asking what could have made it more smooth. A lot of times they’ll say, “Hmm, I don’t know, I think maybe, I guess, well, we could have…” and I just sit there and ask, “Okay, how would that have made it better?”

There have been times this question in conversation unearthed something major. In fact, this question is what led to our system of “who owns the ball,” and the daily update that birthed from this question. We’ve created a system of quality control checkpoints we call “quacks.” We have all of these in place because we asked what we would have done differently to improve the results of a project. It’s one way to do an autopsy, if you will. As far as the general week goes, what you’re going to be doing is inspiring self-awareness and innovation in work habits for your team by asking this question. It’s a powerhouse question.

A third question I ask is, do you feel like you’re growing here? What I’m listening for is whether they feel stretched, challenged, and seen. Growth is one of the biggest drivers of retention, especially with millennials and young team members. They want to be growing, they love a good challenge, they love to be developed. It’s exciting to them, it’s life-giving to them, it’s something they seek out. I need to know if they feel like it’s happening here. I don’t care what they say at first. If they say yes, I’m like, “Okay, tell me something in the last several weeks that’s an example of the evidence that you’re growing here.” If they say no, “How do you feel about that? Would you like that answer to be yes? That’s okay. What can I do to help make that happen? What’s a way you could grow? Is there something you’ve heard or seen that you wish you knew how to do?” Maybe it’s not a new skill, maybe it’s new knowledge. Based on their answer, I could recommend a book, a video, a course, paid or free, it doesn’t matter.

The heart behind it is I’m looking to see if they feel like they’re growing here. Some people are going to say yes right away, and you’ve got to dig. Don’t accept “yeah.” I’d encourage you to always ask a follow-up question when you get a really quick yes-or-no answer, especially a yes. If somebody’s just agreeing with you, ask them to unpack it, ask them why. Do that a couple of times, and people are going to learn very quickly that they can’t just give you an answer they think you want to hear without thinking it through themselves. Let people know their answers are important by asking that follow-up question.

Number four of the eleven questions I rotate through is, are you getting enough time to rest and recharge outside of work? This is opening the door to talk about pace, boundaries, and what mental health looks like for them, and this is so important. I’ll ask a follow-up: “Do you feel like you’re getting enough time? What have you been doing lately? What’s that been looking like for you?” I’m going to learn about hobbies, about interests. There are times I’m like, “Oh my gosh, I didn’t know you did that, I like to do that too,” or, “Wow, I had no idea that was something that helps you feel rest and recharged.”

This is a big problem on remote teams. People work from home, and it’s so easy for them to overwork, and it’s your responsibility to make sure that doesn’t happen. This is a good question to ask yourself too. So let me ask you right now, podcast listener: are you getting enough time to rest and recharge outside of work? What do you need to do about it? How are you going to fix it? If you said you are, how are you going to protect it? How are you going to model it for others?

There’s so much that having these questions and wrestling with them can do for you. So even if you don’t have a team, you still need to lead yourself better to live better. I would still challenge you to try to answer them all at least once.

I didn’t want to take up this whole episode just going through question after question, this podcast would go on forever. So for now, if you’d like the list of all eleven, here’s how you do it. Go to EricDingler.com and look for “Five Habits That Keep You and Your Business on Track.” Now, what do these eleven questions have to do with five habits that keep you and your business on track? Well, it’s a brand new resource I’m rolling out in today’s episode, and I’m going to be promoting it for a while. When you go to the website and download it, you’re going to get an email with a link to a page of bonus resources, and the very first bonus resource on that page is the eleven questions I use in weekly one-on-ones. It’s going to say it’s from episode forty-nine.

Moving forward, as I release new episodes and pull from my own swipe file, I’m going to add to this resource page. You’re already going to be on my email list, because after today you’ve downloaded Five Habits That Keep You and Your Business on Track. So when I email you about a new podcast episode plus a new bonus added to the resource page, you’ll just click right over and grab it. If you’re listening to this in the future, whenever you download Five Habits That Keep You and Your Business on Track, you’re going to see a resource page full of resources, and each one lists the podcast episode it came from.

So today, double bonus for you. First, you’re going to get Five Habits That Keep You and Your Business on Track. Habits build outcomes. Your results right now, in every area of your life, your physical health, your emotional health, your spiritual health, your relational health, are a result of the behaviors you’ve done consistently over time. Those behaviors are habits, and they can be changed and modified, and I know that’s really hard to do. There are five habits that, if you begin to engage with them, are going to keep you and your business on track. So go to EricDingler.com, click on Five Habits That Keep You and Your Business on Track, and when you get the email, there’s going to be a link to a resource page that includes the eleven questions I ask in my weekly one-on-ones.

So with that, I want to share this week’s Leadership Tip of the Week. But before I do, would you do me a favor and review or subscribe to the episode wherever you’re listening to the podcast? Review, rate, subscribe, comment, share it. Choose one of those and do it wherever you’re listening to this episode.

This week’s Leadership Tip of the Week: leaders model focus by what they ignore. I love this. This is very much along the lines of “more is caught than is taught.” People are watching you, picking up on what you do as what’s important, and what they should be thinking is important to them too. But the same is true when they see what you don’t do. You need to be comfortable saying to someone on your team, when they bring something up, “That sounds really good, but it doesn’t need our attention at this moment because I want us to stay focused on X. Would you do me a favor and bring that up after [a given deadline]?”

A couple things with this. It lets them know you want to hear it again, but it’s also only going to come back up if it was something that was really important. A lot of times people bring ideas to you just to leave them with you, they don’t want to do anything with it, but they want somebody to do something about it. So I acknowledge it, let them know we’re staying focused on this thing right now, and ask them to bring it back up after we’ve hit a certain point, whether that’s after this project, after the first of the year, whatever it might be. Give them a time, and then you don’t have to think about it again. If they bring it back up, great.

So let’s recap some hot takeaways from today’s show. I’ve got four for you. Number one, let your team know what matters to you with the questions you ask, by pre-planning questions that will get you the information you’re looking for. So pre-plan your questions. Number two, make sure that even if it’s just a one-on-one with yourself, you get it scheduled. Have an agenda, have a plan, have questions, make it happen. Number three, create a not-to-do list. Everybody’s all about their to-do list, got to do this, got to do this. Well, I like to keep a nice, robust not-to-do list, and give your team permission to keep one as well. And finally, number four, make sure you go get the full list of the eleven questions I currently use by downloading Five Habits That Keep You and Your Business on Track over at EricDingler.com.

Until next time, pick at least one thing to take action on this week to help you lead better to live better.