1:1s That Make a Difference

Cal: I wanna start with a real easy question. What’s the purpose of a one-on-one?

Josh: I look at it as: it’s face time with me. I’m a busy person and I wanna make sure that the people who report to me have dedicated “this is your time”. Like, we’re not skipping it. We’re gonna make sure we make this meeting and it’s time for us to connect on a number of different topics.

It could be different, even for different people at the same level, right? For me, it’s about what they want and what they need. But I think the most important thing for me is it is scheduled, guaranteed face time between people who need to connect.

Cal: Now, when you’re conducting one-on-ones, do you have a structure for them or are they just free form?

Josh: I like to think that I have a structure for them, but it doesn’t usually hold. I think, I know a lot of my managers do have a specific structure that they follow, like: we’re gonna talk about this. We’re gonna talk about, you know, these four things, we’re gonna check in on every week and there’s potentially even like a shared notebook that is kept between those two people.

I find that my personal ones, because the people who report to me now are also quite senior, I find that they don’t have as much of a schedule to them and as much of a specific list of things to check off on. What I find at my level, the thing we talk about most is people. The thing that I want to hear about more than how a project is going, or, you know, do we need to change, a technology decision or things like that?

How is your team, how is your hiring going? That’s because we can’t do anything without the rest of that stuff falling into place. And so that’s what I, one of the things that thinking back in the past year, what is the thing that is common among all of it is how is your team: how’s your recruiting?

Cal: The last time I was doing one-on-ones, I was a director-level. So I had team leads, but I also had skip-levels that would come up and talk to me as, you know, regular developers.

Josh: I really love a skip-level. I really try and get at least two a month on the calendar.

They’re just so fun for me to be able to jump down and talk about a very specific project that somebody is excited about that I don’t even know what’s going on. And those, you know, going back to the structure, those, I very specifically say there is no agenda. We will talk about whatever you would like to talk about, this is a social call. And man, I love doing those.

Cal: So, what are some common topics that are covered in your one-on-ones? And let’s talk, first let’s talk about your direct reports and then if they differ for skip-levels, let’s talk a little bit about that.

Josh: The one that we covered already is people hiring, right? So that’s very common. I think the other aspect of that is on that career growth. You really gotta be talking about career growth and opportunity for the people that report to you.

And that’s definitely a thing that we talked about and I think at a, you know, kinda director-plus level, that’s a harder conversation. There’s not necessarily as much slots for people to move up and also it’s harder. And so a lot of that is like, okay, well, you know, you’re a director and you wanna be a senior director. Expectations for a senior director are like, that’s someone who you assume is on a track to become the vice president of engineering at some point.

We have to kind of talk about it together and say, okay, well looking at your responsibilities now, let’s write them down together and let’s look at okay, what comes off your plate as you take on these other things? And that’s a hard thing to get right. Especially – it’s like playing five-dimensional chess, when you have more than 20 people you’re talking about trying to move, and move everybody up, and give everybody that opportunity.

Obviously in a technical product delivery world, we’re gonna talk about how projects are going, we’re gonna talk about, is this on schedule? And a lot of it is – can I help get alignment? I understand that your area of this is working, do we need, in your opinion, to get together with other people? And can I help facilitate that to make sure that when you get to the end of your project and you and I are in alignment and everything’s going great that the other four people who are your peers agree and are at the same level, right?

The other thing that I see a lot that we talk about is, “Hey, I’m seeing something outside of our organization that we should talk about. You’re not in that workflow, but I am. And I think you should be aware of it so that we can go figure it out. I’m seeing this problem get solved seven times in a row, instead of giving one solution and repeating.

So that then I can say, okay, now I can have the full picture at the top of the list and say, great, we need to get this, this, this, and this aligned. And we need to get in a room, and now we need to go solve that problem.

Cal: So how should an employee approach a one-on-one? You know, do managers make sure that this is not seen as a disciplinary session or what?

Josh: You know, I hope that no one who works for me has ever thought of it that way. I’m not gonna say it’s never happened, but I would hope that people don’t think of it that way. What I want really most in the world is for people to be able to feel like it is their time.

I feel like if employees are relying on their manager to set the agenda every single time for that, or hey, we just set this agenda, we never talk about anything that’s not these four things. It turns into a status check-in, and those just aren’t super useful. It becomes a chore as opposed to, “oh, I’m looking forward to this conversation.”

I think that’s where I’m a big fan of the concept of managing up. And so, that’s an opportunity for you, a person who is doing the work and probably knows better than anyone else what your boss needs to know, to bring that conversation to your one-on-one and say, “Hey, here’s how things are going. Here’s what you should be aware of. Here’s what I’d like your help with.”

Cal: I’m your direct report? What do you expect me to come out of a one-on-one with, is it, am I just supposed to get a warm fuzzy? Or do I have action items? Or what?

Josh: If I was gonna boil it down to a word, it would be: clarity.

What I’m hoping you get out of that is if something was unclear or misaligned or it wasn’t going the way you expected or you just didn’t know, right? Like, I don’t know how we should approach this and if I can give you nothing, it’s kinda like going to a tech conference. If I go there and I spend three days and I, you know, I come away with one thing, I’m happy.

I’m not asking for you to solve it for me. I’m just verbalizing it. Like, “Hey, this is hard and we’re struggling with it and I’m not entirely sure what we’re gonna do, but we’ll figure it out.” Right? That’s a lot of what I get. “Just so you know, we don’t know the answer to this. We’ll figure it out, but we don’t know yet.” Right? It’s like, “Well, have you thought about X?” And if I can give you that X, right? If I give you that, “have you thought about thinking like this?” and you could take that away and come back and be like, “Hey, yeah, that was actually it.” Or “Hey, yeah. That was a dumb idea, but it did lead us to the correct one.” If I can just give you one nugget in there somewhere, I’m happy.

Cal: I’m gonna throw you one that’s not on the list. How do you handle the hard conversations? Do you handle rectifying that in a one-on-one? Or is that a different meeting?

Josh: Unless it’s minor, I think it’s a different meeting; it shouldn’t be a disciplinary conversation. Probably the biggest reason for that is because one-on-ones are on a schedule and if you have a problem like that, you gotta address it immediately.

But I think if it’s like, “Hey, this isn’t going well, you told me this is gonna be delivered on Wednesday for the last three Wednesdays, and what’s wrong?” That’s not necessarily a hard conversation, but it’s like, “Hey, you’re not quite meeting the expectations that we have or that you also told us to have.” Maybe a one-on-one, ‘cause I view that as a, “tell me that it’s a problem”; I can help solve if there’s something going on there. And I can get involved and help solve it. When it is a harder conversation than that, I think you gotta do it separately and you gotta do it quick.

Cal: What didn’t I ask that you think is important for people to know about one-on-ones?

Josh: One of the things that I really try and catch myself doing, because it feels natural, is you get into a one-on-one conversation with somebody and it’s going places, right? Like, yeah, that’s great, let’s talk about that. ‘Cause I wanna, I wanna talk about that problem; let’s get into it. We’ve got time. Now this one-on-one conversation, especially at the senior manager kind of up level, you start making decisions. And those are decisions that the two of you, you got it, right? Problem solved, decision made.

But now, there’s four other people who need to know about that and they weren’t there and they don’t have the context. “Hey, we’re doing X.” “Um, okay. Well, why? When did we talk about that?” I especially think that happens in remote work. It’s a big difference where that problem occurs. At the office we can be like, “Let’s just go get ’em right now and tell ’em.” And we can talk about it; that instantaneous “let’s just go get ’em and talk about it” is really hard to do digitally.

So I think that’s one of the things that I try and be conscious of is, let’s make sure that that one-on-one is about you, right? That we don’t drift into making team or other decisions that now we really should have had that in a meeting with multiple people so that everybody had the chance to participate, so that we don’t have to then re-litigate it and re-decide it again.