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  • Writer's pictureMax Wenneker

[Management 101 Podcast] How to have effective 1-on-1s

[Transcript from original podcast episode edited for clarity]

Hello, and welcome to another edition of Management 101. I am your host, Max Wenneker. Thanks for joining again. Today we're going to talk about 1-on-1s. I'll talk about what a 1-on-1 is, what a 1-on-1 isn't, best practices for those 1-on-1s, how to make sure that you get the most out of them, how to structure them effectively, and some tools we'll talk about at the end to ensure your 1-on-1s are effective. Before I get to that I first wanted to thank the maybe two to three people who listened to my first episode and just want to call out the almost 100% audience engagement in terms of ideas for names for this podcast. By the way, I'm still out there looking for the most punny name possible for this podcast. I got “Somehow I Manage”, which is a “The Office” reference. Unfortunately, there's already a podcast by that name and it's actually about “The Office”, so I can't steal that one. But still open to ideas.

What is a 1-on-1?

Anyway, so what's a 1-on-1? First, let's just define it. A 1-on-1 is an interaction between a manager and a person who is reporting to them. And generally in my podcast, I'm going to talk about people reporting to a manager as “direct reports”. That's the term that I have heard used in my career, so that's the term that I will use here. I'm going to talk a little bit about what I've heard from managers and their direct reports about 1-on-1s. There's definitely not one single definition. And I definitely don't think it's well understood exactly the value of 1-on-1. This is interesting because, in my experience, 1-on-1s are probably the most important tool that you have as a manager to effectively lead your team in ensuring they're doing the work that is expected of them.

So what have I heard about 1-on-1s from managers? Certainly many I've talked to do not understand the point. Some have never even heard of the concept. I'll quote a manager I spoke with once who said, “usually I just cancel them because I don't have anything to talk about”. And another one who said, “my direct report never has anything to say. So it's just awkward”. So obviously there are managers who are familiar with 1-on-1s, but we've all, I'm sure, had managers who did not prioritize 1-on-1s, or who very clearly didn't have a good understanding of what 1-on-1s were.

The same goes for direct reports. We've all had managers before. We've all been direct reports. Here's what I've heard from some folks who have reported to me or were reporting to me for the first time. Again, a number of them have not ever heard of the concept. Certainly very few of them even find them beneficial. A former direct report of mine at Uber said, “I thought this time was for my manager to tell me what to do”. Just a spoiler alert, that is not the case.

So why don't we talk about what 1-on-1s are supposed to be? I think 1-on-1s are really about four things. One, it's a forum for a direct report to escalate problems to their manager.

Two, it is a forum for a manager to provide updates on company and team priorities. Three, it is a forum to build trust between a direct report and their manager. And four, it is a forum to problem solve. Generally speaking, that fourth one, the problem solving, is what should normally take up most of the time in your 1-on-1 interactions.

What makes a good 1-on-1?

So you're a manager, you're saying, okay, I guess it makes sense to me that I need to have 1-on-1s, but what needs to happen for those 1-on-1s to be good? I guess some ground rules first for you as a manager about 1-on-1s. One is, keep them scheduled regularly. They should be recurring meetings between you and your direct reports. I also want to call out that they should take first priority. Unless you're going on vacation, 1-on-1s need to happen basically every week. And nothing else is quite as important, at least in the workplace. So where possible, I think it is really important to keep 1-on-1s. Sometimes these are the only forums in which your direct reports can actually bring up issues they're experiencing.

If you end up canceling 1-on-1s repeatedly, you do a couple things. One, you show that that direct report is not important to you. But two, you also stop some of these problems from getting solved because it's very possible you are the blocker to that solution occurring or even that solution being thought of. To be clear, that doesn't necessarily mean they have to happen at the same exact moment every week. I think it's okay to move them around as needed. But beyond them being regularly scheduled, I think it is also important that they happen on a weekly basis, more often if someone is new to your team or the company, because they're just going to need more guidance, they're going to run into more blockers and potholes and they're going to need your help just getting onboarded.

How to structure a 1-on-1

Personal check-in

How do I like to structure 1-on-1s? There's an order of three or four major topics or areas that I cover. First and foremost, when I show up to a 1-on-1, I like to check in on my direct report as a human being. Obviously they're not just a professional. They have a life outside of, outside of work. At least, I certainly hope so. Even at work, we're all human beings and things affect us. We're not robots in the workplace. So I like to just check in on them and see how they're doing.

This does a few things. One, it shows that I care, which I do. I think it's very easy as a manager to care, but the direct report doesn't realize that you care. And so checking in on them is a way to show that you care. Two, it builds trust between you and that direct report because you are asking about them and engaging with them, and that inherently helps build trust in the relationship. Three, it reflects to your direct report that you know that they're more than a worker. There's more to them than that. You're calling out that they're a human being with your actions and your words. So we'll talk through that, and sometimes folks have a lot to say about what's going on with them. I like to ask follow up questions and like to just get to know people on a personal level. And I know that's not every manager's style, but I have found it really effective in ultimately building a strong relationship and getting the most out of that person long term, because it's allowing me, by checking in on them, to manage the whole person, which I think is a really important aspect of being a manager.

Ask what’s on their mind

Next, the thing that I focus on is what, what do they want to talk about? Some direct reports come to meetings with laundry lists of things that are problems that they need help with, or questions they want to ask about what's going on in the company or the team, or they're looking for a sounding board, you name it. I like to kick it off by just asking what is on your mind? The reason I ask that versus “what do you want to talk about” is that while some direct reports do come in with a laundry list of activities or things to discuss, not all of them do. And oftentimes, particularly early on in a managerial relationship, people don't always have a whole lot to say. Again, not all of them are even familiar with what a 1-on-1 is supposed to be. So when I ask “what is on your mind?”, the goal is to not just ask them what they want to talk about, but rather just have them check in literally on their brain and see what they're thinking about. That often sparks conversation that can lead to an exchange of information and decisions and solutions that that just started with such as, “oh, I'm having this thought”, or “this thing is bothering me”.

I can't claim to take ownership of “what is on your mind?” as a question. First of all, it's probably not trademarkable, but I borrowed this from a book that I highly recommend for managers, particularly first time managers who have not been in a 1-on-1-type setting before. The book is called The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever. It's by Michael Stanier. It covers seven questions that are really important questions to ask as a manager on a consistent basis, because they're the questions that help you as a manager get the right information from your direct report and help lead them to the right place.

Check on work since the last 1-on-1

We've now asked them what's on their mind. We've gotten some good tidbits of information about what's going on with them in the team, with their work, et cetera. And now it's time to dive a little bit deeper into the work itself. I want to call out here that I think as a manager, it's important that you don't act as a dictator, but rather, particularly in 1-on-1s, as a partner. You and your direct report, first of all, are literally on the same team, but second of all, from a work and productivity perspective, you two as partners make a lot more sense than one of you doing the work and the other just telling that person what to do. So when I do this check-in on a team member's work, I'm trying to do it from the perspective of being a partner of theirs, a thought partner, and also someone who can help get things done.

I start with just checking in on what are the major things that they accomplished over the last week, both things that they had committed to, as well as other things that came up that they maybe got done. And then I like to ask about what they didn't get to. What had they committed to last week in your 1-on-1 with them that they were not able to ultimately accomplish? More importantly, what caused those things not to happen? I can remember a time that a direct report, after a number of 1-on-1s, the consistent theme was that he had not been getting done the things that we had talked about in almost every 1-on-1. To the naked eye, it might have seemed like he was a slacker, but that was definitely not the case. And the reason I figured that out was we literally went through each of these items that he didn't get to each week and discovered that the reason was he had a bunch of requests coming up from other stakeholders that he was just saying yes to because he was trying to build good relationships with them. Those requests were derailing his normal priorities that he had committed to each week with me, and therefore distracting him and causing him to be unable, in a reasonable amount of time at work, to get all of the things done that he wanted to. And so what we ultimately dug down to was his problem was not that he wasn't getting the right stuff done, it’s that he was actually just incapable of saying no.

We had to come up with a system. He had an intake process where instead of just saying yes to a stakeholder, he would first try to understand why they needed X or Y piece of work. He would try to estimate its necessity or impact versus the other things he had on his plate. And then we would discuss together whether it made sense to prioritize that thing instead of what he was doing, or whether it made sense to say no or delay that work such that he could continue doing the work he'd already committed to. The only way that I would've discovered that those things were happening was by asking what else was going on, what caused him to be unable to get the work done that he had been committing to. Ultimately I think it was a great development experience for him where he set up a system where he could say no more effectively and he was significantly more productive and delivered much higher-impact work.

Discuss plans for the coming week

We've talked about what are the major things that the person accomplished last week and also what they did not get to. Now it's time to talk about what is going to happen this coming week. This is a combo of asking them what they want to get done, talking to them about things that you see needing to be done, and then discussing how to get those all accomplished, in what order, and what the various priorities are.

Problem deep-dive

Now it's time as manager to dive a little deeper. What problems did they run into last week that stopped them from getting things done, or even just caused their experience at work to be suboptimal? The reason we have to ask these questions is, like the example I gave earlier, it's important not just to understand what happened, but why and how. If there are problems that the individual is running into that's stopping them from getting things done it's really important for you as a manager to understand that because you're actually the one who needs to help solve for that long-term and block and tackle for them so that they can get their work done. You're knocking things out of the way to enable them to get good work done.


The last question I'd like to ask is w what, what you, or what I, as their manager can do to help them accomplish their goals this week. I've gotten some interesting answers to this. Sometimes the person just says “I’d really appreciate it if I could just have some more non-meeting time. I'm in 20 meetings this week and I really need some time to get work done.” And then we'll take a look at their schedule and try to figure out what to prioritize and what to deprioritize. They've also said “I'd really appreciate if you could sort out this problem I'm having with this stakeholder. It seems like maybe our two teams aren't aligned.” That's, that's my job as a manager to figure out how to make that happen. Basically to block and tackle, get the problems out of the way such that they can just do work. Sometimes when a team member escalates something to me, it makes sense to see if it's a problem they can solve, but sometimes it really just makes sense for you to step in as a manager and get that problem out of the way for them.

Org updates

The last topic I like to cover is just providing the team member with relevant team and company updates. Are there major projects or initiatives starting that might impact this team member's work? Is there any change in company priorities that could be relevant to this team member? And then are there any new pieces of work that it makes sense for this person to own? I don't necessarily mean just assign it to them, but bring it up conceptually:

“Hey, this is something that I've talked to the leadership team. We believe it needs to get done. I think you are the person who makes the most sense to take on this work, but I want to see what your workload looks like, such that we can prioritize it in the right way against all the other things that you're doing.”

A good 1-on-1

Now I want to talk about some examples, or maybe some guidance as to what a good 1-on-1 looks like versus a bad 1-on-1. A good 1-on-1 is a discussion more than anything. It's not a set of directions. It's not necessarily just a vent session, although sometimes it can be. We'll talk about that in a second. It's a discussion. You are asking questions as the manager to foster that discussion. And that discussion ultimately leads to both of you ending up with more information than you had before, and therefore better decisions being made.

So a 1-on-1 is a discussion and an exchange of information, and ultimately is a working session to solve problems that exist in the team and in the work.

It is definitely not your job in a 1-on-1 to tell your direct report what to do. It's kind of like giving advice. When someone doesn't ask for advice and you give it to them, it's reasonably unlikely that they'll either take it with a grain of salt or not take it into account at all. Whereas if the person learns that lesson on their own, they're much more likely to internalize it and remember it. So your job is just to ask the team member the right questions so that they can figure out what to do. Instead of saying, “this is how you solve this problem,” you can say, “what are some ways that you could solve this problem?” or “Which of these do you think makes the most sense to do?”, “What are the trade offs?”, “What do you see as the potential downsides of trying this solution?”, “What are some other solutions that might make sense to try?”, “Are there other people we should talk to to come up with good solutions?”

Sometimes 1-on-1s require just a lot of listening on your part. Just sitting back and listening. There are times, because we are human beings, where direct reports are just going to need to vent or they have other things going on. When your direct report is in a bad headspace, it's much like when your significant other is. It's not going to be very helpful to try to actively solve the problem with them because they may just not be capable of it right now. They may need to vent and express their frustration or negative emotion around whatever's going on at work or not at work that's really taking up their brain space. And at that point, your job as a manager is just to listen and to empathize. You can only discuss the solution once they've moved past whatever's going on. If you try to force a discussion of a solution, they're either not going to be open to it, or they're going to feel unheard, which is a problem long-term for your relationship with your direct report. Sometimes when folks are in a bad headspace and they need to vent, it's your job to just listen, acknowledge what's going on, and then later you can discuss that solution to the problem once they've cleared it up and moved on.

A bad 1-on-1

A couple big no-nos in 1-on-1s. I want to call out that there's a difference between a 1-on-1 as I define it here, and a development check-in. 1-on-1s are much more tactical. They're about the day-to-day. Development check-ins are about the person's career trajectory and how they're doing in a larger sense in the role. So 1-on-1s are a really bad place, generally, for substantive feedback. These are things beyond,”I noticed these slides were missing this piece of information that we discussed.” That's a very tactical piece of feedback. Providing feedback like, “I think you're struggling in your ability to get stakeholders on board with your vision” is probably not a great place to talk about this because it's very bizarrely juxtaposed with talking through the specific things that need to get done each week. There often isn't enough time and the person is not in the right headspace to be talking about deeper feedback that's more pertinent to them as a person in some ways than just the work they're doing.

I also want to note, it's very easy to end up in a place when you developed a close relationship with a direct report for them to feel comfortable bringing up concerns about other team members to you. That's potentially okay, though I think generally it's good to try to keep that discussion productive. I really cannot stress enough the importance of avoiding talking poorly about other team members or other teams. You as a manager, much like as a parent, are kind of setting the example for your direct reports because you're likely the person who they take the most influence from in the workplace. And if you're going to be shit-talking other teams, they're going to take that to heart. I definitely learned that lesson the hard way early in my career, and I just cannot stress it enough. Avoidance of shit-talking is really important to maintaining productivity and positive attitude and morale within the team.

Tools for 1-on-1s

Okay, we're going on 23 minutes now. Hopefully I haven't poured too many people to death. I just want to spend another couple minutes talking through some good tools for 1-on-1s. So first, the point of tools in 1-on-1s is to just have a place where you can both put items you want to discuss throughout the week. Sometimes I'll come up with a topic that I want to talk about with my manager. It's helpful to have a place to note that so I don't forget about it. This place is also to keep track of commitments that you're both making and, by the same token, to track follow-ups from previous 1-on-1s. Over time you can easily check in on what you are accomplishing each week and what you were committing to each week. It gives you a really good sense of the team member's performance.

There are a few different tools that I've used, all of which I like for different reasons and all of which have their downsides. The first one that I used in my most recent full-time role was 15Five. 15Five is a tool that allows a few different things to happen. It's great for each individual team member submitting a pulse check just to see how they're doing and also to track items that each of you wants to discuss. You have a page where all the things you want to discuss come up and then you can check them off as you talk through them. And anything you don't get to gets automatically pushed to the next time. You can also add stuff throughout the week. The problem with 15Five in my experience is that it's not nearly as good for tracking follow ups. It's really hard to look over time at due dates and what people were supposed to be doing or committed to. So I don't like it as much for that reason.

Another option is a typical project management tool like Trello or Asana. That's really good for tracking progress on individual items. And you can also set it up to make it pretty easy to add items that you want to talk through throughout the week. I think the downside is they're somewhat involved tools and my experience in a bunch of startups is that people feel very passionately either positively or negatively about these tools. It's very rare for an entire company to be on the same page about which of these tools makes the most sense.

The simplest thing that I like to do is just create a Google Doc that's shared with my direct report. It's “Max + direct report 1-on-1,” and each week is its own section header, and then under it you have topics that you each want to talk about and you can both access it throughout the week. You can both put follow ups there. You can comment things like due dates or assign things to each other. It's really lightweight and takes very little effort to ramp up to. But I think the most important thing is just having a tool that you're both on board with more than anything.

Thanks so much for listening to my talk about 1-on-1s. I hope you found this useful and that you can implement some of these ideas in your own work with your direct reports. Once again, as I mentioned last time, please feel free to reach out to me on, on LinkedIn or on my website. I love meeting founders and managers and providing guidance. I have a lot of fun helping people become better leaders and would certainly love to help you if you're interested in just getting a sounding board or a thought partner for being a better manager and leader.

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