“What we need in these times is a new style of leadership that's more focused on empathy. You know, we still want to find ways to be effective at getting things done. But empathizing and [00:17:00] understanding, the stress that people are dealing with and how that, plays into their overall effectiveness at work is a new sort of nuance skill that I think everybody is having to deal with. You really have no choice"

Welcome to ALL HANDS by Lattice, where we believe that People Strategy IS Business Strategy. I’m your host -- Katelin Holloway. For the last decade, I’ve been a People & Culture executive at some of the internet’s most beloved startups, but my fascination with building true people-first cultures started many, many years ago. From film to tech (and a few interesting layovers in between), the one common denominator remains: I am most passionate about enabling people through belonging to create beautiful, innovative products.

On All Hands, I talk with CEOs and other c-level leaders about how being a "people first" company is a strategic advantage. Join us while we chat with these top leaders about how a “people first” approach isn’t just good for people -- it’s good for business too.

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[Music fades out]

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In this episode, we're chatting with Nick Caldwell, VP of engineering at Twitter. Once upon a time, Nick and I shared an executive table at the then fourth-largest internet destination in the United States, reddit.com. Nick joined the Reddit team as VP of engineering after a 15 and a half year stint at Microsoft.
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His experience helped us to scale our technology and team as well as our commitment to ensure we hire and nurture a diverse organization.
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After our work together at Reddit, Nick joined the Lookr team and led them through a successful acquisition by Google. Ready for his next challenge -- and a big one at that -- he joined Twitter in early 2020. Nick, welcome to All Hands.

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Nick Caldwell:  Thanks for the invite. Happy to be here. Happy to reconnect with you as well. Uh, since our Reddit days, um, Katelin, Katelin deserves a lot of the credit for the goodness that that happened at that company, that during those years. So I'll throw it right back at you.

Katelin Holloway: Well, thank you kindly, sir. I am so grateful for this, this opportunity to reconnect and really, um, share and amplify all that is Nick, You have so, so much to be proud of in your career. Um, and, and you, your path continues. And so, you know, it's funny, I think back to when I first met you the very first time I met you, uh, you were sitting in the smallest, most awkward, crappy little room [inaudible] in the old Reddit office.
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I don't know if you remember that super awkward room.

Nick Caldwell:  Yeah, the storage room with the turf that had been added to make [00:02:00] it themed. That was bad.

Katelin Holloway: It's funny to think about how far Reddit has come, how far we both have come and how our journeys have kind of unfolded in front of us.
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But thinking back, I, I just remember walking in the room and seeing you sitting there. And you were easily the best-dressed human in that entire building. Like, easily.
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And I know that we aren't supposed to do this as people leaders, but I met you and within the first five minutes, I was like, this is it okay. If we can just chat now, like I'm good. This is, this is the human to do this for us.
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We, we built, we built so much. Um, and, and that was amazing. I'm so proud of the work that we did together, and I'm so proud of what that team became. Um, but can you take us back further? Let's, let's go back to your early days. Can you [00:04:00] tell us a little bit about yourself and your own journey leading up to that point in time and then take us beyond bring us up to speed?

Nick Caldwell: Yeah, sure. I mean, I, I guess I, uh, the most interesting sort of career inflection point is sort of that. Moment you're describing. And I guess leading up to it was, I had been at Microsoft for a long time. Uh, about 15 years working my way up through kind of this, I don't wanna say it was on rails, but you know, in a big company, you've got a pretty well defined career track.
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And I was thinking about how to grow my career in one, particularly Microsoft defined, narrow way.   I was fortunate to, to be asked to work on a product called Power BI. I was on the founding team of that. And, um, we grew that over the course of three years from kind of a 15 person organization up to around 300 people and it became Microsoft's I believe fastest growing product for 2016 is currently, uh, the number one BI [00:05:00] product in the world.
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And that was an amazing experience for me because of what I learned. I learned how to execute, et cetera, but it also opened up sort of a, a big obvious question, mark, which is, Hey, uh, you just created a brand new product, family worth multiple billions of dollars inside a large company uh, and you got some promotions for that, but, um, maybe there might be another way that you could have done this. So, uh, I think it was around that time when I was working on, on power BI that I started to think about  making a move, uh, into, into startup life and also during this time I got my MBA at the same time. Cause I think at that time I thought you might need an MBA to be an entrepreneur. That was wrong.

Katelin Holloway:  Oh, silly.

Nick Caldwell:  Yeah, that was, that was an incorrect assumption. But one thing it did do, because I got my MBA in, in, uh, in Berkeley, I was flying from Seattle down to the Bay area every [00:06:00] weekend. For a couple of years, I got exposed to a very, very different network in the Bay area.
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And that was valuable. Like that was worth the entire cost of my MBA. Just forcing myself to meet people who approach their careers in wildly different way, to discover how venture capital networks work. And then to realize that the skills that I had  accumulated at Microsoft, working in large teams and building large organizations actually translates extremely well to what people need and startups.
So the the flip side of, of most startups is that they typically don't have people who understand how to build a large skill organizations. They, but they do have the innovative spirit. They understand what's bleeding edge. So I think For me, it's been, an amazing journey. So when I, when I was interviewing and eventually ended up at Reddit, I believe that was what we primarily talked about. It was how do you take a kind of scrappy, small startup and add sort of [00:07:00] rigor of execution and scale without breaking the fundamental culture. Right? And so, you know, doing that, uh, with, with you at Reddit over two years, that was one of the most fun things I've done in my life.
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And it was a great decision to take that leap. And I was terrified, but it turned out, uh, okay. Now later on I had the folks from Looker. Looker is another business intelligence company. And they, uh, knocked on my door and said, Hey, Nick, we actually have a different challenge for you to take on.
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And here we want you to come in and, uh, uh, take on the chief product officer role. I ran product engineering, design, product marketing, and a couple other functions at, at, uh, Looker. But the interesting aspect of this was, was Looker was. At that time, seriously thinking about IPOing, or ultimately we got acquired and being a part of that journey, seemed incredibly [00:08:00] fun.
And also difficult. Yeah. I won't go into detail about what needed to be uh, addressed at Looker other than the say, you know, okay, well, you know, this you're, you're an HR, anytime you're hiring an external exact, there's usually something that they're missing internally that they want you to come in and fix.
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And Looker was, was no different. I had a ton of time, a ton of fun kind of diagnosing that company and helping them on their path toward, uh, an acquisition. And, um, we landed in Google. A lot of the, uh, uh, we're looking for what to do next. For me, at this point in my career, I, I wanted to do some, another big challenge.
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Of course, I love jumping in the fire and doing difficult things, but I think also I wanted to do something that would be very meaningful. And so I spent a lot of time exploring different and opportunities and, uh, ultimately Twitter came along and Twitter has this nice intersection of things I was looking for as my, as my next move.
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One is, uh, going back to what I was talking about [00:09:00] earlier, big organizational scale challenges here at Twitter.  I'm looking into to providing some of that same rigor that we brought to Reddit at larger scale, helping them fix some of their, uh, technical challenges and tech deck concerns.
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But stepping back from that, Twitter is mission is the way they talk, talk about it as the mission is to serve the public conversation. Um, and the way that I interpret that is Even before I got this job, I was thinking to myself like, how's the world changing? And one aspect in way the world is changing right now is that social media is becoming increasingly the way that people understand what's happening in the world.
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Uh, not just from an event based perspective, but also how they interpret and make sense of what's going on in the world. Every era has had perhaps a different communications mechanism, you know, from the printing press being invented to, to radio, to [00:10:00] TV. And I think this eras, you know, mode of communication, the thing that we have to discover how to harness and make available in the right way is social media. And Twitter, more than any, uh, any company is, uh, at the heart of live events, news, and how people process the world. And I thought to myself, like, that's a mission I could bite into it and it's important to society.
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And before I got the job, I was thinking, well, I'd like to join and see what I could do in order to help the company get prepared for the election, because that would be, it'd be really important. And then I think like COVID came and then we had COVID. Then we had black lives matter. And we've since come to decide, is that, yeah, it's not even the election.
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It's just continuously like the, my belief that Twitter was going to be the way that the world kind of processes and understands what's happening in the world. That's already happening and accelerating right now. So I think I've made the right call [00:11:00] from that mission perspective.
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I'll just suffice to say um, the, the company as a whole is learning a lot from these last three months. I mean, the whole industry is, but I'm really proud of how Twitter in particular is addressing a lot of what's going on with COVID, remote work, black lives matter, et cetera.

[Music up]

So much of this resonates with me. One thing about Nick that has always inspired me is the way his leadership style has developed over the years. When Nick moved from Seattle to San Francisco there were several people that packed up their homes -- and their families -- just to work with him again. Seeing that made me realize the power of the relationships we build.

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[Music fades out]

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Katelin Holloway: And then, now just to flash forward to, to how you've paid it forward. Not just inviting people into your organizations again over time, but the, the way in which you're giving back to your community, I smile when I see your shirt, which our audience cannot. It's your dev/color. I remember, you know, we, we both were  introduced to that organization around the same time. And I, uh, I actually, I had talked with them for several years prior wanting to partner, and I did not meet the requirements as an organization, and then you came along and you were able to help us build and develop and grow that. And you've taken that with you for the last, you know, three gigs, um, because it's about the people.

Nick Caldwell: That's exactly [00:14:00] right, yeah. In the long run, I think people matter more than anything. I tell, I tell folks those, um, you know, as a technologist, Your job is ultimately to, to build things, but you're building sand castles, all, all of this, this techgets, if you're, if you're building something that's of any utility as tech changes, so will the code that you've written.
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So will the products, it will just get redone, but the thing that has repeating rewards and value in the long run is your network. And the people that you invest in and particularly for leaders, I think there's a certain stage in your career that you get to where you understand that your goal is really just to develop more leaders.
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So I always tell people leaders make new leaders, and I have. A particular passion for building structure and opportunities that will systemically do this and allow people to grow and flourish. And nothing makes me happier. This is an odd thing to say cause I think most companies don't want you to [00:15:00] talk about career development this way, but many of the people that you're referring to, like, you know, that came with me to Reddit have since gone on to other executive roles at other companies. And to me, that is amazing. Well, I guess it means that I brought them up to another level, gave them access to opportunities they wouldn't have otherwise had. So I think like all leaders have to have, you know if they're going to be as successful as possible, a philosophy around developing, uh, developing new leaders. The give-back aspect is incredibly important too.
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I think dev/color it's personally important to me because of my career trajectory through Seattle. So, I mean, it's, it's a good organization, but it's really resonated with me because, um, You know, one thing I sort of glossed over my 15-year career at Microsoft was that, you know, Seattle is relatively not a diverse place.
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I went through [00:16:00] all of my Microsoft career without seeing another black tech exec. And, you know, mentally, I have to kind of put up guard rails to this. So you can't be thinking about it all the time or you won't be effective at your work.
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So I kind of push that to the side. And when I moved to San Francisco, the first I'm meetup I went to was a dev/color event and a dev/color for, for those who don't know is a network for black engineers to who try and help each other achieve their career goals. So, the first meeting I joined 300 other black engineers of   levels, and abilities from new grads, all the way up to other execs. And for me, this was just a light switch, transformative mind-blowing moment. I didn't even know this sort of thing was possible.

It's sort of two parts, like one is, I want to make sure folks don't have to go through the same sort of feeling of isolation that I had for a big chunk of career. So for companies that are maybe too small to have their own employee resource groups, devcolor can provide that, that feeling of connection.
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The second thing is dev/color is really about. Helping folks achieve their career goals. So it's not just a network. You come and hang out with people you know, and have fun. You have to set goals and hold each other accountable.
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So in a world where  technology is really the best source of opportunity in the wealth creation and it is unfortunately inequitably, distributed. Organizations like dev/color, I think are essential to closing the gap. And that's why it's so critically important to me. So thank you for letting me complete that rant.‍

Katelin Holloway: No, no, I love it. you know, we, we've been talking about how our networks and our ability to leverage our networks it's not just self-serving necessarily, although it is helpful, you know, the example of getting your MBA and how what's more important to you that, that diploma, that, that hangs on your wall or the relationships that [00:03:00] opened up doors for you to, to come to the Bay area and experience something new, you know, take that leap of faith after 15 plus years of working within one organization.
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And, and then now the opportunity to really give back and to build more. And I, I knew the dev/color is just one example for you. So I think that that's an incredible way to demonstrate leadership and also to demonstrate that, you know, the jobs that we have, I love the description of we're building sandcastles. That's all this is that's all any of us are doing right, truly. Um, but our relationships and the, the dynamic that we have with others and the way in which we enrich our communities, both from, within our organizations and the, and the power that we have there and outside of our organizations, the community, you know, the communities in which we live. So, I appreciate you, you sharing more about that one because it is a phenomenal organization and too, that's just one example of how we can better connect and how we can better serve as leaders as we move through this world.

Nick Caldwell: Yeah, absolutely. I mean, sometimes I [00:04:00] worry that I may be too high up Maslow Maslov's hierarchy, but I think that's, uh, at this point and at an early stage in my career, I would have answered you differently about what's important. I think people early, people early in their career. At least for me coming, coming from a, uh, where I grew up was PG County, Maryland. I don't think we were necessarily the most affluent family and the earth and, and early in my career, it was super important, uh, to build wealth. And then once I had a handle on that, the second phase of my career was, was more about freedom and trying to give myself more opportunity and moving to Reddit and understanding how venture world works and startup works as part of that. And now I'm thinking more about legacy and how I give back and what I'm going to leave behind. And I want that to be an easier path, uh, for the next Nick Caldwell who comes up behind me.

Katelin Holloway: Let's switch gears a little bit and bring you up to, uh, Twitter. So you, you've only been at the company for just a few months now.  You talked a little bit about this, um, in your, your journey part of the story. Um, but what was it like choosing a new role, a new company, in the middle of a pandemic? I adore your, your wife who also works in the industry as a technologist. Was this a, a big decision in your household or, you know, not knowing now the barrel of here?

Nick Caldwell: So my wife knows me pretty well. And so I remember I came home from work, uh, One day at, [00:06:00], you know, this was after we'd been acquired and I'd largely, uh, integrated Looker into Google. And she asked me how my day was. And I was like, it was pretty easy. And I remember the next day she was like, when are you leaving? And I like, she knows me well enough. It's like the, the instant, I start to feel comfortable. She knows I'm not happy. And, uh, so she totally got it and it wasn't a surprise I think for her that I was interested in doing something new.
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And when she found out that I was interested in Twitter, I think she knew immediately that I was going to take the job. The funny thing is I accepted the offer before. Uh, before COVID really spun up.
And so I didn't know what to expect, like [00:07:00] joining, joining as a, uh, as a leader in these times, you know, it's already hard to do the traditional expectations. Like when you come into a new role, you're dealing with a all-new cast of characters, you have to build trust and relationships with. Like any exec job I've come into, I've been given sort of an early mandate or a set of things that the company wants me to address. And, um, with COVID, it's all of that plus dealing with a set of challenges that, uh, I hate to say unprecedented, but I'll just say it , you know, I guess we'll, we'll just keep throwing it around.
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There's we got to come up with a new sentence, but it's totally true. And I, I worry about this a lot because, because we're dealing in a series of situations where people don't don't know what to do exactly. We're trying to figure out changes, not just at the workplace, but, in the next room over my niece is doing PE for school.
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Could you imagine, like a year ago, if someone had told me that the next door, my niece would be doing remote physical education ain my living room like that's insane. Right? So a lot of, a lot of this is being worked out in near real-time.
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And I think it, it puts a, a whole set of challenges on, on all leaders, uh, to, to overcome like understanding, the unprecedented levels of stress and anxiety that people are dealing with, not just related to COVID, but I mean, black lives matter, we're at a time of real societal change right now, and that is all adding up to, uh, new behaviors, new ways of, of empathy, new ways of giving people time to recoup and recover. Uh, all of this is being learned in, in real-time. So in, uh, in one respect, this is [00:09:00] fascinating, like as a person who loves thinking through org design, as well as, uh, how, how to best, uh, lead people.
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In some sense, this is the best learning opportunity that I've had in a while cause I think it'll result in longterm changes that we got at the end of this will come out a lot better. Like I'm, I'm actually fairly optimistic for example, about where remote work is going to end up. This has been one of Twitter's values for a long time. I'm told since joining, I can see it in person, but I'm told that for a while, the company has been trying to push toward a more than 50% outside of San Francisco, decentralizing in a way that brings, that builds new offices around the world and, and, you know, pushing hard for remote work.
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So, the cool opportunity here is like all of that's going to be accelerated. The problem and the difficulty is going through it. It's all the, it's all the change and uncertainty in the middle, which is the, is the tough part.  and I guess the other thing [00:10:00] just onboarding, I mean, like COVID was like a bunch of uncertain, we have to try new things and empathize, but, uh, the second week on the job was really when black lives matter, started to kind of really kick in and I, you know, separate from Twitter. I mean, just any like any black person in the United States who was going through this was dealing with, I mean, just why, I mean, I, uh, I can't even describe the amount of despair that I was feeling while simultaneously trying to onboard and put on a, put on a brave face for the organization. I think the, the great thing about that though was, at least at Twitter and I also saw this at many other companies too, like the outpouring of support and empathy, uh, was high and it helped a lot.
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Uh, I think that we're still dealing with this problem in real-time, but I remember the second week I was on the job, [00:11:00] Jack Dorsey, our CEO, was having sort of listening sessions where he, uh, we had, uh, uh, Bernice King, Martin Luther King's, uh, daughter, uh, come and talk about the situation Jack himself was talking about how he was giving away a significant portion of his personal wealth to both COVID relief and Black Lives Matter.
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I actually suggested a charity, after I found out he was doing this, I suggested the charity to Jack and he donated to the, to that charity a few weeks later, which made me feel pretty good. I mean, he, he put, he put his money where his mouth was.  Twitter, Twitter has an ERG called blackbirds, which started hosting a series of events internally and externally.
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Some of them, some of them were honestly just huge venting sessions, but, but it was, it was what we needed at the time. And now we're still in the thick of this, but I, I think I've had time to reflect on all the ways we can also leverage that opportunity as well. And I think some of [00:12:00] what we need to make sure that happens with black lives matter is that, that feeling that change needs to occur, uh, translates into real, tangible action. I've been, uh, uh, trying to find ways to work with, uh, for example, exec recruiting firms who are looking to, to do better and connect them with up and coming Black and Latinx uh, engineers.
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Uh, I think in many ways we just have to make sure that we don't lose this opportunity for change in, uh, in inclusion and diversity that all of this. This unrest and anxiety and energy actually results in lasting change. So yeah, I could go on, but I would simply say that like the, the actions, uh, of Jack and the Twitter family, blackbirds, uh, have been, you know, both emotionally helpful for me, but also just practically speaking, tangible. I expect tangible changes to, [00:13:00] to come out of all this as well, which in the long run will, will matter more.
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[Music up]

I’m so grateful that Nick shared this with me --- the ways that Twitter is leading the conversation around supporting your people is a great example of how a company can be inclusive. Inclusion isn't a feeling, it's an action. Belonging is the feeling. That's how you know when your inclusion and diversity initiatives are doing what they’re supposed to.

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[Music fades out]‍

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Katelin Holloway: I want to dive a little bit more deeply into, uh, the, the support side of things. So I think that, you know, work from home is a, we, we talk about it as a policy. Uh, but really it's a, it's a practice. It is the way in which we [00:16:00] allow flexibility for people to be able to work and for people to be included for us to attract a more diverse workforce. And right now it's, it's, it's a mandate., but beyond policies, how do you sense in yourself or feel that all of these things, all of these compounding events are shifting and changing you as a leader? How are you showing up differently than, than you did before?

Nick Caldwell: You know, I think, you probably know me from my time at Reddit where I was largely brought into to help execute. And as a leader, I think particularly now, but I also learned this at Looker as well, which had a, a culture that needed certainly the ability to execute.
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But what we need in these times is a new style of leadership that's more focused on empathy. You know, we still want to find ways to be effective at getting things done. But empathizing and [00:17:00] understanding, the stress that people are dealing with and how that, plays into their overall effectiveness at work is a new sort of nuance skill that I think everybody is having to deal with. You really have no choice. If you want to come into today's environment with sort of the hard charging. You know, I, I started my career at Microsoft where it was, you know, you have bill Gates and Ballmer, like banging on throwing tables through windows and stuff like that just doesn't fly anymore.
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Like, you know, the, the pendulum has swung toward a world where. Uh, empathy is the high order bit. And you use your connections with people to build trust, and that translates into effective execution as opposed to the older world where you simply demanded execution. And that, that is only doubly true in COVID times where I think, uh, it's not that you want to get into a mode where you're walking on eggshells around your employees, [00:18:00] coworkers. It's more that you want built checkpoints and systems into your room, regular routines. So that there's an opportunity to detect if, if people are potentially at risk for burnout or stress, like one of the things I like that has happened here at Twitter is Jack, uh, has started to give people effectively a day off a month to kind of rest and recuperate.
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The other thing that they've done, which personally helped me quite a bit was, um, meeting free Fridays across the company, which I desperately needed. Like, you know, this, this extra time uh, is very important, to, to just let people process what's going on. I think it's also important from the perspective of preventing burnout.
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That is to say, now [00:19:00] that folks are largely gonna use to work from home and some of the issues related to, uh, childcare, I don't think they're fully resolved, but they're starting to. We're starting it to a world where people are able to manage that additional workload. What are starting to emerge is that for certain types of work, work from home ends up being, um, Equally, if not more productive and, uh, you don't have to deal with commute times as a whole.
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You don't have to deal with walking between offices and so forth and So on. So you're getting, uh, perhaps equal productivity, uh, and at the same time, people are stuck in the house. So like mathematically, that means you have to, you have to let people cool down. Yeah. And so, you know, I don't know if Twitter has done this intentionally or unintentionally, organically, but, um, this additional time to cool down has been incredibly useful.
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And I think in the long run, like in a post COVID world, I think certain aspects of this people will want to retain. Uh, and that begs the [00:20:00] question, like what do we do with, uh, offices in the future? Um, I think remote guaranteed. I, I, I read, uh, uh, sorry a series of tweets from another leader who, who would disagree with me.
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Uh, they want to get back into the office as quickly as possible, but I think that's right. That's crazy short sighted. Like I know we're dealing in a time of unprecedented change, but we have to be able to imagine a world posts COVID and not lose some of what we've learned through this, this whole situation.
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And what I'm learning is that remote works really well. Gives us potentially equal or greater productivity and access to diverse talent anywhere on the planet. You know, Twitter, like, obviously we want to be a global platform for communication. And the only way we can achieve that is we have, is if we have representation from around the world.
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So maybe I'm just being an optimist. Uh, you know, I know that we're deep in the thick of a lot of bad stuff happening, but [00:21:00] just to, to point out one thing that like, we will take away from this whole experience on the other side, right. Is leaning into remote work so that when we get to the other end of this, we have the tools and methodologies for allowing people across the planet to work at one company.

Katelin Holloway: I am equally as excited as you about all these opportunities. I think that from a, a position of creating a more diverse and inclusive workforce, I I'm right there with you. I think that something that, you know, the leaders we're really pushing for the let's everyone, I can't wait to get butts in seats again, um, perspective is that, you know, that was okay before, because we were all just trudging through it.
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And that was the normal. We didn't [00:23:00] know any different, we didn't know any better and it's not just the exception to, Oh, Hey, this works. It's also the fact that we're all coming out of this as changed people.
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And I think that companies like Twitter, who are able to pivot and are able to be agile around, what does this look like? Who are comfortable, um, and supportive of people, breaking paradigms, these are the companies that will win. If done really well, will be the ones who win, [00:24:00] who come out the other side and it has actually made them stronger than what they went in.
Alright Nick ---- Time for the rapid-fire questions!  it is fun and it's quick and it's rapid-fire for a reason. So answer quickly!

Nick Caldwell: I'm the worst at these. Whenever I do a podcast that I always get stuck on these rapid-fire questions, you know, you know, I can't answer any question then less than like three minutes. So I will, I will try my best Katelin.

Katelin Holloway: Okay. First one is a hotdog a sandwich?

Nick Caldwell: A hotdog is not a sandwich. A, uh, I'm not sure what it is, but it's been debated by philosophers since time immemorial. Nobody actually knows what it is, but it is definitely not strictly a sandwich. Probably it depends on context.

Katelin Holloway: You are such a Redditor.

Nick Caldwell: Everyone at Reddit has read the debate on is a hot dog a sandwich.

Katelin Holloway: It's true. [inaudible] please. Okay [00:26:00] here, here's a Twitter, rapid fire. Retweets, add a quote or just straight up old school retweet?

Nick Caldwell: I I'm a fan of the quote suite because I want to add a little bit of my own sauce to the tweet. I think, I think that's what people expect. You know, they want a little bit of extra spice on the original tweet.

Katelin Holloway: Next question, uh, is deeply personal. What is your favorite sneaker in your shoe collection?

Nick Caldwell: So my absolute favorite is a pair of, uh, Uh, re-issued Chicago One Jordan’s, they're, they're my absolute favorite. I just got them last year.  I'm a sneakerhead. I think you probably knew that from my blog post, but-

Katelin Holloway: I have not asked anyone else this question.

Nick Caldwell: Number one the Chicago's followed closely by the, um, Taxi [00:27:00] Twelves, the, the, those look really great. So I'll stop there.

Katelin Holloway: The good news is that was the warmup. I mean, maybe it won't be so easy, but if you want to expand on them, you may know no hard, fast rules here.

Nick Caldwell: Okay. Let's do it.

Katelin Holloway: Company culture: family, or sports team?

Nick Caldwell: I think it's in the middle. Like I get asked this question a lot, actually. so your company is not your family, because you can't fire your family members, uh, at the same time, the sports I've seen companies that have, do done the, like we're a sports team sort of, [00:28:00] um, analogy and the challenge there is um, if you treat everyone like a free agent, they ended up having a sort of mercenary attitude, which doesn't lead to long term loyalty. So I think that the right answer is in the middle. It's like you do want to be able to hold people accountable for high performance, but at the same time, it's, it's better for everybody if you can do that in a way that provides teamwork and long term stability. So I think it's somewhere in the middle.

Katelin Holloway: I would agree with you. Okay. Next question. Getting the right people in the right chemistry is one of our most difficult tasks as a people leader. How do you know when you have the right people assembled to build something?

Nick Caldwell: Oh, that's a, that's a really tough one. I think there's a, there's no magic solution to this. I think every, every process, project needs a different sort of jazz band to be assembled, to play the right notes. So it's, it's hard to predict without getting people into those situations. [00:29:00] But I would say like, you know, in, in the highest performing teams that I've work with and built, you see a level of, um, I just, I don't want to beat this jazz band analogy to death, but like in a, in a jazz band, people play off of each other. And, um, everyone has sort of a unique thing that they do well, but they don't do it independently, they do it in service of the overall group.
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And it's the collection of these unique individuals, but working together toward a combined mission which is what makes the, the outcome great. So, you know, the way that you measure this is from an engineering and product perspective, the way that you measure this in a quantitative, you know, way, is, is that team ship, you know, meeting metrics and OKRs and Yada, yada yada, but, but I don't think that captures like the true spirit of what a high performing team is because it's hard to measure the more qualitative aspects of like, Hey, these people actually [00:30:00] like each other. And I think where you see that kind of playing out, going to what you were saying earlier is teams that persist, wanting to work with each other over time, regardless of what the underlying project is, and that's harder to measure. But I think that, you know, over time is how you would see that.

Katelin Holloway: I love that. I like the jazz band analogy.

Okay. last question. And this one is designed to be a trick question and to be very challenging. Um, and we've gotten very, very interesting answers over the course of the season. Uh, when I asked this and I'll give you a little context before I ask it, um, outright, and this is the [00:31:00] question that I have asked of every, uh, potential leader that I am considering working for.
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Um, This, I'm not asking for a job just to be clear, but this is something that is really important to me to understand, um, what drives them, what motivates a human at a particular stage in their life. And so the question for you, Nick, is when was the last time you wanted something so badly it hurt?

Nick Caldwell: Uh, I think that I tend to have those moments quite frequently. Some are, some are personal and some are more work related.
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I think the last thing I wanted so badly at her from a work perspective was the opportunity to have this role that I'm in right now because, [00:32:00] Oh, this is going to sound lame, but the mission, and impact that I can have here, if I'm able to succeed in, it will allow me to meet, not just all the cool building, neat products and so forth, but I'm at the stage of my life where I want to leave something behind and leave a legacy and like, what I'm, I'm not leaving Twitter anytime soon, but when I do someday in the future, what I want to leave behind is the most diverse engineering organization in the history of Silicon Valley. And I also want to have left back a product and technical capabilities that allow Twitter to, to achieve its full potential. And the moment I realized that this was like during the interview process where I was kind of playing around with the recruiters and, you know, you gotta do your little back and forth and negotiate.
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And they were like, well, Nick, we got another candidate as well in the final interview. And it was that [00:33:00] moment. I was like, no, no, no, actually this is, this is my destiny. You know, Katelin you used to always talk about destiny and, and, you know, everything happens for a reason. And for me right now, like Twitter is that destiny. I want to see, you know, uh, how I can use this opportunity to leave my mark on the world. And I think from a professional perspective, I can't think of anything I'd rather be doing.

Katelin Holloway: That's awesome, for what it's worth, that's actually the answer that I, I seek when I am talking with, with, you know, leaders of organizations, it's, I want to understand and know that they are doing the right thing at the right time., and it shifts and it changes, and more than that, I also want them to hear that they, they have personal things, even if they aren't in a position to share in that moment, or it's not appropriate to share in that moment, but understanding that they are a person who has wants, needs and desires outside of, what is in front of them. And so, you nailed my interview, Nick.

Nick Caldwell: Thanks, Katelin.

Katelin Holloway: I [00:34:00] appreciate it. So, one, one final question though. The rapid fire ruse is done. I want to bring us back to today and to current event, uh, you, you obviously have a lot of really incredible work ahead of you to do that. You were excited to do, you are at right place at the right time with the right people, uh, which is all, any of us could ever ask for.

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But what advice would you give to founders and people leaders out there who are trying to make sense of this moment in history? How can they really use this as the opportunity to build a better organization for this next chapter?

Nick Caldwell: So, I mean, it's, it really comes down to two things that you have to do right now. Like you will regret having missed this opportunity or, or look foolish if you don't do these two things, like one is you have to lean into remote work. It's just obvious. That doesn't mean like necessarily giving up your, your headquarters, if you, if you like having your HQ in beautiful downtown San Francisco, but you must aggressively at this moment in [00:35:00] time, think through a strategy where future employees are going to want to work from home or remotely. It is the way that the world is going to change and you have to  get on that trend right now.
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the second thing is  there's never been more of a time where you could lean in to, uh, work on inclusion and diversity and get results. So I, I think for a long time in the history of inclusion and diversity work to be quite blunt. Like, you know, people would look down on, on folks who were doing that as like, Oh, it's like a side gig. It doesn't have anything to do with like the main, the main job of getting your work done. I think that was always wrong and today if you were afraid for whatever reason, to, to take a stand and, and start, uh, I don't wanna say doing the right thing, but trying to, to work toward goals related to [00:36:00] inclusion diversity, not only is now the safest time to do it the most appropriate time to do it,you have momentum behind you, but you can push even farther. Like one of the things I'm pretty excited about here, Twitter is it's, you know, we've got tons of ERGs and so forth and so on, but we have quantitative goals associated with inclusion and diversity work, like specific metrics that we want to hit, that the whole company is aware of.
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So if you're sitting on the fence right now and your company doesn't have these things, do it now, like we have the momentum, like that was the time to, to, to take, uh, take a stand and do what's going to be proven right in the long run I guarantee you.

Katelin Holloway: I love that. I think that's a beautiful note to end on. Nick, I'm so grateful for the opportunity to reconnect. I'm so excited for, for everything that is yet to come for you and for your beautiful bride Tia and everything, uh, that you, you are going to build. I am so excited to be supportive and to, to watch what happens. And, um, I'll be right there cheering on [00:37:00] with my rapid fires. Watch out.

Nick Caldwell: Thanks Katelin. This is, this is awesome. And it's great to reconnect with you as well. I really enjoyed my time here.

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[Music]

Katelin Holloway VO:

And to you, the listener! Thanks so much for joining me on this week’s episode of All Hands, brought to you by Lattice. I’m your host, Katelin Holloway.
This episode was produced by Pod People: Rachael King, Eliza Lambert [AH-liza], and Samantha Gattsek [GATT-sic]. Special thanks to Annette Cardwell. Learn more about how Lattice can help your business stay people focused at Lattice DOT com or find us on Twitter @LatticeHQ. Don’t forget to subscribe to All Hands, wherever you get your podcasts.

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Join us next time!

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