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Technically Human

A connection-based approach to 1:1s for remote teams

David Kyle Choe
May 31, 2021

Technically Human Ep 6 Ft. Tim Whitacre, Engineering Manager at New Story - How transitioning to remote work has changed his perspective and strategy to connection-centric 1:1s

David Choe: Alright!. I thank you guys. Thank you everybody. Welcome to a, another episode of Technically Human. We have a very exciting episode today. I'm with one of our very own customer advisory board members, Tim Whitacre. Before we do that, I want to introduce myself. I'm David Choe the co-founder of Staat and the host of Technically Human.

This is Tim Whitaker, I'll let you introduce yourself to Tim.

Tim Whitacre: Yeah, thanks for having me. Yeah, my name's Tim. I am an engineering manager at a nonprofit called new story charity. We're based here in Atlanta, Georgia, and we have a office in San Francisco as well, and we work to end global homelessness specifically focused in Mexico right now.

David Choe: Awesome. Can you tell the people a little bit more about what it is you actually do? Because what the company does? Because I think when I first heard about New Story, I was blown away at the work you guys are doing. So I think people would love to hear more.

Tim Whitacre: Yeah, sure. So we our, our, our, our biggest, our biggest effort is to pioneer solutions to end global homelessness.

So we, we are as much of a tech company as a nonprofit. Our goal is to figure out what solutions we can use that will maximize our efforts and maximize any donations that we get to The fight against homelessness. Our company is also we also have a a hundred percent model, meaning that a hundred percent of every dollar donated goes directly to the work we do.

And then our overhead, like our salaries and travel and things like that are funded by a group of Really generous donors.

David Choe: That's awesome. Very similar to the charity water model, right?

Tim Whitacre: Correct. Yep. Yeah. Awesome. We're good friends with those guys.

David Choe: Oh, that's great. Yeah, that makes total sense. And I mean, as much as I'd love to talk more about news story, what we're here to talk about today is actually.

Really, you know at a topic that comes up a lot more often than you think, and that's one-on-ones and Tim has a pretty unique approach to one-on-ones with his team at New Story. And so Tim, I'd love to hear from you about, you know, what it is you, how you approach one-on-ones and what, what advice you might be able to give to our audience?

Tim Whitacre: Yeah. I think the first thing I'll start off by saying is we definitely have a one-on-one structure, like a pre COVID. Post COVID one-on-one structure. You know, before COVID, when we were still in the office, you know, our, I think our goal was to have them every other week or every other third week, something like that.

And oftentimes they ended up being like, Hey, let's go, let's grab it. Let's go walk to the coffee shop and grab coffee, which I think is good sometimes, but it lacked it lacked a structure and it lacked something where we could like, Like have anchor points in the conversation that we can come back to in the future.

And so when we when our team went fully remote, you know, about a year ago, we realized pretty quickly that we needed to have a better structure. And so we actually started doing a one-on-one weekly one-on-ones And we, we tried a few different formats, but the current format that we landed on is essentially I think they're scheduled for about 30 to 45 minutes.

Some of them take some of the people on my team. It takes 30 minutes. Some take more like 45. And we spend the first bit just kind of catching up. We'll do something like red, yellow, green, or some other sort of a really simple format of just basically like, how are you? How's life how's work. How are your goals?

Yeah. You know, it could be as simple as I slept terrible last night because my kid was up all night or something. And then, and then from there, we'll kind of dive into looking at, you know, what was, what are some things you wanted to accomplish last week? How did you do it's less like a standup or a check-in and more of just a conversation.

But we found that they've been really beneficial to both the team and myself as an, as a manager. Right. And then the last part of it, we have a section where our. It's kind of like a transparency section where the team member can, you know, we have a list of like potential topics, but they could, they could talk about anything from, you know, career growth to goal, to raises to really anything that they want.

And we, we make sure we have a section. I would say that probably gets that section probably gets filled in and talked about maybe like once every two months. But we make sure we have like a dedicated time for that in our structure.

David Choe: How many people are you managing right now? Roughly?

Tim Whitacre: Right now I'm managing three.

So we have a pretty small team on the engineering side. Yeah. Well, we're hiring for two more, so.

David Choe: And so can you talk a little bit about kind of the, the structure before COVID and the structure after like, you know, what, how did you guys. Think about one-on-ones in what place did they have in, in your workflow and, you know, in the overall career progression and it being a little more informal, what was the impact of that versus a more formalized approach now?

Tim Whitacre: Yeah, I think the informal side of it was It definitely. There was definitely, it was nice sometimes because like I said, we would, you know, we, we work in an area where we could go for a nice walk outside, go to the coffee shop. But it often, sometimes you'd realize you'd, you'd spend the entire time talking about a show you watch the night before or something going on in each person's life, which is not always a bad thing.

And sometimes that still does happen in our new format. Right. The difference is that Having a structure in place means that both sides, the manager and the and the direct support can they can act, they actually know that like they have time on a calendar to speak into the things that they want to want to know, want to have answers to.

So, yeah, I think that was the biggest shift. That made things better. Also consistency is good. So I think at one point in time, it was, you know, especially early in the, early on when I moved into management role at new story it would be a thing where I would kind of look at the calendar. Oh, I haven't had a one-on-one with so-and-so in a few weeks now I would Slack them and say, want to go grab coffee.

And that would kind of check the box, which is definitely not the , right. It's the right way to do it. So.

David Choe: So, how are you kind of like managing all of the inputs? I'm sure a lot of people are saying things that you need to capture and record and keep on file. Do you have like any system or preferred method there?\

Tim Whitacre: As far as, so as far as managing or like capturing the info, like the conversation, the, one of the ways we do it is every team member both on my team and then a company-wide they will fill out a. Kind of a standard template at doc every like the end of their week on a Friday. So I do my one-on-ones on Monday.

Got it allows me to kind of set the stage for the week. And so then the team, they fill out their, they thought their document which should only take them about maybe, maybe 10 minutes at the most, but I fill it out by the end of the day, Friday, which means they kind of like reflect on their week.

Look forward a little bit to the next week. And then so that way we can always go back and look and see. So if there's, so for instance, if there was ever an employee who was really struggling, I would be able to go back and look and see like, okay, did they accomplish their goals every week? No, no, no.

But, but that's all, it would be a lot of work to go back and do that, you know? So we're still, we're still figuring that out, but yeah, we do it now.

David Choe: Part of it, I think, you know, in my, in my time being managed I remember having very similar one-on-ones we would do what was it? Start, stop, continue.

So I think very similar to green, yellow, red and it would be such a mess for me cause I, you know, sometimes I would write notes on a piece of paper or write down on my computer or whatever, whatever I had in front of me. And I would just completely lose track of what I was supposed to do or let you know the toll, the totality of progress, which I think is, I think is really interesting because, you know it, you have to take these kinds of.

Moments, these minutias these weekly check-ins and basically create a narrative around a person's progress, cumulatively holistically. Do you have any kind of advice on that? Cause that is a really daunting task, I would say.

Tim Whitacre: So, so on are on like the, the page that they document their their weeks on. We also do have their quarterly goals around there and we use, we use OKRs. And one of the ways that we track that is how, like your percentage complete towards a goal. So we, we try to make sure our, OKRs are very.

Did they have some trackable metric to them? Like, you know, from something as simple as, you know, launching three new features on a product to a more complex of like having, you know, 80% of support tickets closed within 24 hours, you know? So then we can go and look up that information and we can track the progress towards the goal.

So I think that with the weekly dialogue Has has really helped a little bit or helped a lot, actually. Yeah. Yeah. One thing we did recently started doing is we've added in basically, like a larger personal growth metric, which is, you know, our OKRs are quarterly, the conversation piece is weekly, but then this personal growth thing is it could be six months.

It could be a year. It could be five years. It's kind of like, you know, if I said, David, what is your goal in. You know the next, like, what is your goal at the company? And if you said, Oh, I want to be, I want to be a senior manager. I want to be a lead principal architect. You know, it's like, okay, now we have a goal that we're working towards.

Right. Let's continue to talk about this every, you know, every few weeks, every few months, and like, see like, what are the steps that you need to continue to work on in order to go there? Some of those, it could just be. Time, like you have to be at the company so long. But it also would be like, you know, if your goal was to be a lead mobile developer and you were only touching mobile a few times a week, that could be a problem.

Right. So

David Choe: no, those are great points. I think, you know, one thing I'm interested to hear is like, I think your, you touched on it a little bit before, but the, the in, I think a lot of managers might be drawn to the, informality of like, Check-ins that are just kind of like walk and talks or coffee chats or whatever, because it takes the pressure off.

Right. And at the same time build some level of, I think, trust and like, it doesn't feel like this corporate structured thing that is kind of another one of my managers tasks that I have to partake in or participate in. How do you maintain like that that's that level of camaraderie or like just that level of informality and trust and transparency that may be, you know, Was was more apparent in, in the former version of, of the one-on-ones.

Tim Whitacre: Yeah, that's a great question. Quick side story. When I first started in tech back in the 2007, 2008 the company I worked for had a ping pong table and every couple of days our managers walk through and just be like, let's go with ping pong meeting, and then you'd have a go out and you'd play ping pong and you'd talk.

And, and that would be your, that would be like your growth set, your personal growth conversations, but sometimes it's great, but sometimes also hard to, you know Yeah. So I think one of the ways that we, because when we started talking, you know, we went remote and we had that conversation of how do we have something a little bit more formalized to really make sure we understand how the team is, but also keep the level of personal connection there.

And so, and that's why when we set up the structure of our. So at the structure of our meeting, we actually call our meetings, CATs: C-A-T and so C stands for connection. And so the first part of the first part of the meeting, which could be five minutes for some team members could be 30 minutes for others is really about connection.

Like, how are you doing as a person? This is less about, did you meet your goals? Did you do that? It's more of like. How are you doing? And so we make sure we carve out time for that. And that's the first thing we do. And then A stands for accountability. And that's where you talk about goals. And then the T like I mentioned earlier, is transparency where you can talk about your future progress.

David Choe: Wow. That's really helpful. And is that something that, did you say that you recently used CATs as a framework or is that.

Tim Whitacre: Yeah, we started that. I would say probably in may of 2020 of last year, we, you know, shortly into like work from home pandemic life. We, we had tried to like mash up some formulas that we'd found all over the place and we realized that we needed to create our own.

And so that was kind of where we, where we landed. And we've been doing that for almost a year now.

David Choe: Wow. I love that. That's really helpful. Actually. I think, I think most people are doing "ATs". You know, and then missing that the first C there. Yeah. No, that's that's really good. No, yeah, this, this has been amazing.

Is there anything else that you, you know, I think something that we kind of talk, want to hear more about is how first-time managers should approach these scenarios. Because I think like, A lot of folks aren't trained, they're not, they're just kind of put into a managerial role from IC perspective and, you know, kind of left to their own devices.

So I'd love to hear from you, like, you know, any mistakes you made along the way as it relates to one-on-ones or, you know, stories you can share for, for first time managers up.

Tim Whitacre: Yeah. I think, you know, one of the. That's some piece of feedback that I got really only about, about, about a year and a half ago, was that as a manager, one of your, one of your key roles is to advocate for your team is to advocate for what they need.

Whether it's a personal growth thing, or even something as simple as like, you know, somebody needs a new computer or a new mouse or keyboard. And so. I realized very quickly that like, okay, somebody needs a new mouse. Like that's a conversation, right. But if somebody is struggling or if somebody is not doing their best work, there is most likely a reason behind it.

And it's not that they hate their job. I mean, let's hope it's not that they hate their job. It's that maybe something is going on in their personal life or something is going on where they are feeling like, you know, maybe imposter syndrome at work. And so I think. Keeping the, the connection piece open and just being very, very empathetic to the fact that, you know, people's nine to five is not their whole world.

I think that really changed everything for me. Wow. Yeah, we've we've, we've had people that have struggled, especially when they were so used to coming to a vibrant office every day. And now, you know, for a long time they're forced to work from home. Right. So we really had to make sure that. You know, we really dialed up the empathy in that time.

And I think that's what saved a lot of us, so yeah.

David Choe: That's really good. Yeah. It's it's, I think it's, that's a really hard lesson to learn is like where you start your assumptions and conversations. Do you start them from a place of, like you said, Oh, this person hates their job or they're incompetent.

That's why they're doing X, Y, and Z versus a complete different unrelated factor. So I think that is incredible advice. Yeah. This has been an awesome time. I think our listeners are really gonna appreciate your insights and have a lot to think about and take away. So thank you so much.

Tim Whitacre: Yeah. Thanks for having me.

David Choe: Awesome. Thank you so much, listeners for tuning into another episode of Technically Human, please check out Tim. I'll link out his LinkedIn and other relevant links out there. Please check out new story. They are doing incredible work. So yeah. Thank you guys so much tune in next week. All right, we'll see.

Bye.

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