“I think what’s really important in a hiring processes […] is to actually look at what are people doing when you’re not paying attention to them […] Are they advancing their skills, again, when no one’s looking? Or are they just telling you that they do all these things, in an interview process?”
Outside the Valley is back! Today we have Steph Smith, author, developer, and Founder of Integral Labs!
In this episode, we talked about the “give and take” approach in remote hiring and why you should actively hire “givers”, the three must-have aspects of effective leadership, how to be a better communicator through deliberate practice, and more!
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Topics also covered on the podcast episode:
- What attracted Steph to remote work
- The “give and take” approach in remote hiring
- How Steph learned to be a better communicator
- Can you deliberately train communication skills?
- How to encourage top-down empathy in an organization
- Why humility should be at the core of leadership
- The three must-have qualities of effective leadership
- Frameworks for remote decision making
- Is there a middle ground between “delegating” and “being hands-on” for CEOs?
- How Steph adapted to remote life and still finding time to be creative
Mentioned resources:
- Nomad(hubb)
- Eunoia
- FeMake
- Ken Weary of Hotjar – How to Regain Productivity in Your Remote Team
- Must-Have Qualities for Effective Leadership
- Best Practices for Managing Remote Teams: A Psychological Perspective
- Give and Take: Why Helping Others Drives Our Success by Adam Grant
- Jason Fried
- Basecamp
- Sam Parr
- Steph’s website
Full transcript:
Jovian: Welcome to another episode of “Outside the Valley,” a podcast by Arc, the remote hiring platform that helps you hire remote software engineers and teams easily. Here, we interview remote startup leaders, remote work advocates, and remote workers of distributed teams who thrive outside of the Silicon Valley. I’m your host, Jovian Gautama.
Here with us today, is one of the most creative thinkers and writers I’ve known when it comes to remote work management, leadership, communication and growth. She’s also a prolific programmer and indie maker, with several unique side projects such as Nomad Hubb, an exploration tool for coworker retreat, Eunoia, where you can find untranslatable words of more than 70 languages, and FeMake, the home of data on female makers.
She was also the head of publications at Toptal. Very pleased to be joined by Steph Smith. Steph, welcome to the show.
Steph: Thank you. That was such a great intro.
Jovian: Yeah, well, it’s also because, like, you just do a lot of things. So, I need that long intro.
Cool, so Steph, I usually just start with very basic, like, can you share a bit more to the listeners, about who you are and your background?
Steph: Sure. I don’t know how far back you want me to go, but in terms of what I’m doing these days, I guess you covered it. I like doing a lot of things. So, I work full-time in marketing, but I also in addition to that, write for my personal blog, which, you know, covers topics that I care about like remote work, learning to code, women in tech, things like that.
And then I also learnt to code over the last two years or so, and throughout that time, created side projects like the ones that you mentioned. So, that’s what I’m doing now. In terms of further back, I did a degree in chemical engineering, and my path here was pretty scattered. But yeah, I guess, key takeaway is I like doing a lot of stuff and getting involved in different areas.
Jovian: Yeah, what attracted you to remote work, by the way?
Steph: Yeah. So, in, what was it, 2015? I was working in consulting for, I only did it for a year, and I knew pretty much right away, that’s, you know, it’s a great job for some people, but it wasn’t really what I wanted to do.
I was commuting two hours a day, living in a city that I wasn’t a big fan of, etc. And even more than that, I was working 60 hours-ish, a week, but also like very, you know, as you do in an office job, very strict hours. And I just didn’t really have flexibility to design my life, so, I decided to look for remote work almost immediately, or pretty shortly after starting that consulting role.
But I also didn’t want to, I’d say, trade my career away, just to work remotely. Like, I didn’t wanna just find any job that would allow me to work remotely. So, I actually spent a greater part of a year looking for different remote roles, and actually, like, engaging with many of them. I think at one point, I had like four little side gigs, in addition to my consulting role, to just like, test the waters, see what types of jobs I wanted to do, but also, like, whether it would work for me.
And then eventually, I kept applying to full-time jobs as well, and eventually, I landed one, which was the job on the growth team at Toptal.
But really, what drove me to want to work remotely was to be able to, basically, redesign my life and be able to live where I wanted, work how I wanted, and things like that.
Jovian: Yeah, I think your story is a great, like, it’s a good reminder of the beauty of remote work. Like, there’s no geographical barrier. Like, theoretically, someone living in Southeast Asia, for example, if they have enough soft skills and hard skills, they can find, you know, high-paying jobs with companies or clients from the U.S. It’s just more about how do you find those, and then building up your skills to be hireable, in a sense. So, that’s pretty good.
Steph: Yeah, exactly. And I would also add on to that, that I now have a lot of people ask how to find remote jobs, because I’ve been doing this for a while. A lot of them assume now that I have many more years of experience in remote work, like I did have that experience back then, and it was much easier for me to find remote roles back then, because I, you know, I have done this for so long.
But back then I hadn’t done it at all, right? Like, I also really didn’t have very many digital skills. And so that’s what I would really emphasize to people, that, you know, it can take a lot of time. It took me around 10 months to set up the right skills, to take the initiative to learn them on my own, and also just apply, honestly, like crazy, until I could find a job that fit what I was looking for.
And so it’s not easy, but for other people who are looking for remote work, it’s okay if you don’t have the skills, yet. It’s just important that you go and learn them.
Jovian: Right. I think this is a good topic to start with one of the things that I wanted to talk about. It’s about the give and take approach that you wrote about. Because in my mind, like when you want to stand out in the digital world, so to speak, especially when you want to find remote gigs or remote jobs, you need to give first, in a way, that means like building something.
So, before we start with that, so you did write a bit about the give and take approach, when it comes to hiring. Can you share a bit more about that? Like, what was that?
Steph: Sure. So, for people who aren’t aware, “Give and Take” is a book by Adam Grant. It’s one of my favorite books, and it talks about there being three types of individuals. One being givers, the other being takers, and then matchers, which fit in the middle.
I guess this is the pretty surface level view of it, but basically, givers see the world as not a zero sum game. You know, giving to someone doesn’t hinder your ability to succeed. He actually shows in the book that when you look at many, many industries and see how people, basically, are successful within those industries, givers end up at the very bottom, and also at the very top, and then matchers, like, fill the gaps in the middle. Matchers and takers, sorry, fill the gaps in the middle.
I was really intrigued to see this, like, why are people who are giving, you know, ending up extremely successful and more successful than people who take or match. There’s many reasons for this, but it’s something that really resonated for me, because I, personally, see myself as a taker. I really try to, anytime I learned something, share it in a way that people can repurpose it, or create tools for people that aren’t necessarily monetized, is something that, you know, I just think is, like, a good thing for the world.
I think it’s especially important, as you mentioned, with hiring, because the most successful teams operate when there are, you know, a majority of takers, or at least, they over index on, oh, sorry, than givers. Because they create opportunities within the team that are mutually beneficial, versus just everything being a zero-sum game in terms of, like, takers trying to advance themselves and not, like, the greater mission of the team or the company.
But it’s hard to actually vet for givers, sometimes, because obviously, in an interview process, it’s like, how do you actually vet what someone’s intentions are? They’re going to portray their intentions pretty positively, regardless.
So, I think what’s really important in hiring processes, and it’s something that I’ve learned over time, is to actually look at, like, what are people doing when you’re not paying attention to them? As in, like, are they creating projects just to create projects, because they love doing that? Are they writing blog posts that help other people? Are they, like, advancing their skills, again, when no one’s looking, or are they just telling you that they do all these things in an interview process?
And so I think the best way, and it’s not some super straightforward process, but the best way I think, to actually find givers, is just see if you can pinpoint their behavior, whether it’s a giver or a taker, outside of an interview process.
Jovian: I really love your take on this, because…so last week, I was talking to Ken Weary, the VP of Operations of Hotjar. So, we were discussing about the importance of seeing someone’s past experience in creating something, when you’re hiring remotely, right?
So, I find, like, hiring givers, it’s not, like, an abstract thing, when it comes to remote work. Because, it really is, like if you hire remotely, if you create a product, if you routinely blog, or even you host meet-ups, like you mentioned, there is a way to, “Oh, this is what they do when not a lot of people are looking at it.”
Steph: Exactly.
Jovian: And that’s, like, a really strong signals that this person will be a good remote worker, so to speak.
Steph: Yeah, and also related to, like, remote work, it’s especially important to find people that act in positive ways when you’re not paying attention. Because when you’re working remotely, you don’t have someone always looking over your shoulder.
People do need to work really autonomously. You wanna find people that, one, are good executioners when they work autonomously, but also, you want to hire people that you, basically, trust to make good decisions, and not just good decisions for themselves, but good decisions for the team, for the company, when you’re not, literally, looking over their shoulder. Which is the reality with remote work.
Jovian: Right. So, in that article you write about givers and takers, there is this one interview question that one can use when they’re trying to figure out is someone a giver or not, which is, “Can you give me the names of four people whose careers you have fundamentally improved?” What are we trying to uncover with this question, actually?
Steph: So, at least the way that Adam Grant describes it, and this is one that he proposes, is that, and this is not, obviously, 100% foolproof…
Jovian: Sure.
Steph: …but in theory, when you ask this question, certain people will respond with people who were higher up than them, of people that they helped. Basically, when they answer that question, they’re like, “Oh, there was this, like, CEO, or my boss, or whatever, and I helped them do X, Y, Z.” It’s more of a signaling thing that, you know, they’re trying to show that they helped someone who’s higher up than them, and who’s impressive than them.
It also shows, like, in a working environment, those are the people that they’re trying to impress. You know, the whole, like, kick, what is it? It’s like kick down, praise up, or something like that.
But when someone actually responds to it in a way where they’re not just trying to, like, show off or signal that they’re impressive, or they work with impressive people, but instead, they’re trying to show, like, people that they actually helped, and the people that they focus on, if they are in a specific role, so if they talk about people who are actually, like, “under” them, or who are at different level than them in the company, then that actually signals that they, potentially, are givers.
So it’s, again, not foolproof. I think this is just, like, one example of a question or a way to, like, word something, to try to uncover how people think about the others around them, and who they actually try to help in an organization, or basically, like, how they fit into that social fabric.
Jovian: In terms of communicating, we know that it’s been almost beaten to death, by saying that communication is important in remote teams and what not. But for you, personally, how did you work on it? How did you work to be a better communicator? What were the things you have to remind yourself in order to be a better communicator along your career, I guess? Like, how have you grown?
Steph: Yeah, I think with remote work, especially, it challenged me to be a much more clearer communicator. What I mean by that is, like, when you work remotely, there’s a lot of information that is not automatic, and so often, can be context lost, or…
You just have to be much more intentional about not just how you’re communicating, but that you are communicating all of the information that someone would need to go execute a project, or to go into a meeting, or whatever. So, one part of that is just being super clear about communication.
Another apart, which is more qualitative, is just when you work remotely, sometimes not just context can be lost, but like, emotion or someone’s actual perspective, or intentions in the things that they’re saying. So, I think you also have to train yourself to almost, like, have the benefit of the doubt, assume the best in people. You do have to train yourself to do that, to work in a positive way with people and assume the best.
And then also tied to that, when you work remotely, a lot of it is very transactional. I think you do need to train yourself to be less transactional, sometimes, and be very intentional about, like, getting to know your team, and getting to know them as people. I think if you’re first starting to work remotely, you can almost, like, skip over that without realizing, and then you find yourself, like, six months in, you hardly know your team past, like, what they actually do on a day-to-day level.
So, I think being a remote communicator is about being super clear, but also picking up on these subtleties. Through that, I think, even though there are subtleties, like, you can be a much better remote communicator. And that’s really important with remote work. If not, you can very quickly find yourself siloed, or just working ineffectively with your team.
Jovian: Do you think this trait of, like, picking up subtleties, or things like this more like, soft skills in a way, you know, picking up subtleties, is this something that one can deliberately train, or this more like some, you know, some inner personality thing? I’m just curious, what’s your experience on this?
Because in my mind, like, when it comes to this, my opinion is mostly, you know, in it. Like, someone is good at getting subtleties or not. I wonder, what’s your take on this?
Steph: Sure. I mean, I think certain people are better at communicating than others, and better at forming relationships. But in this case, it’s not so much about picking up on subtleties in the sense where some people are more tuned to other people’s emotions and things like that.
It’s more just I think any remote worker needs to spend the time to be intentional in terms of getting to know others around them.
That’s not something that is unique to one set of people or another. I think it’s something that, in fact, many people who I think are typically very social, get into remote environments and forget to do, because it’s not set up to, like, automatically train people to do that.
So, I don’t think it’s about being, like, introverted, extroverted or anything like that. I just think that most people, or everyone, should remember to be super intentional about some of those things. I don’t think it’s, like, limited to certain people’s personality types.
Jovian: Right. It’s tightly related to the culture of empathy in the organization, in my opinion. I’m just curious, like, in your opinion, how can you encourage empathy from top down in the organization? So, let’s say I mean, the startup founder building a distributed team, and he or she wants to have this culture of, just like you mentioned, like, everyone to be more aware of the other remote team members.
Is this something that can be forced? It seems like not a big word, like, preach top down in the organization? So, let’s say do you feel like is this something that a leader can transmit to the direct reports, therefore, make this empathy culture spread into the whole organization? Or do you think it’s mostly about hiring the right people from the beginning?
Steph: It’s a mix of both, for sure. Like, culture is an aggregate of the people who are in the organization. So, if you hire a bunch of people, a bunch of takers, for example, like back to our first discussion, and you try to tell them to be empathetic, like, that culture will just be so strongly ingrained in the people and how they operate.
So, I think hiring is the first area that people need to pay attention to. And again, focusing outside of just how will this person execute from, like, a specific technical perspective, versus how will they actually add to or take away from the culture that you’re trying to create.
But then outside of that, what I see a lot of the time is, you know, most companies, these days, have some sort of culture page, where they try to emulate, like, the type of culture they’re trying to create. But then sometimes, the actual actions within the organization don’t match that.
The best way to, actually, past hiring, the best way to, actually, you know, encourage empathy, for example, within an organization is not to put empathy on your culture page, but to actually, as a leader, if you’re a CEO, or if you’re an executive of some sort, is to actually not just execute or show empathy yourself, but is to actually reward that.
So, are you rewarding people just based on their, like, net output, regardless of how they interact with other people or support other people? Or are you rewarding people based on, you know, how they support other people, or how they’re collectively executing as a team?
And then also tied to that one thing that I find, even more commonly, I’ve seen, is that people, it’s not just about who you reward, but also, like, who you choose to fire or remove from the team. So, it’s not just about, again, like if there’s someone who’s, like, a great individual contributor but is really hindering people around them, or actually counter to the culture you’re trying to create, you should remove that person from your organization. It’s not an easy decision.
But I guess my point is that whether you’re trying to encourage empathy or some other part of the culture that you’re trying to create, you need to actually facilitate that, not just through these, like, culture pages or, like, hypothetical tools. You need to actually execute on that with your actions. Your actions are, again, who you reward and also who you choose to not reward, or potentially, even remove from your organization.
Jovian: Yeah, you have to be vigilant, in a sense, like, and be consistent.
Steph: Consistency is so key there.
Jovian: Yeah, so we also covered a lot, in this podcast, we’ve covered a lot about leadership, because I think, in my opinion, like, when it comes to remote work…okay, I mean, good leadership works, be it both in co-located or remote teams. But I feel that there is a special thing in remote work, because you’re basically, as a remote leader, you are more constrained, in a sense. So, you have to find a way to go through that with consistency, like, you mentioned, and just, you know, just be very intentional of what you do.
So, I want to talk about leadership, a little bit. So, you have this amazing article about the three must-have aspects for quality leadership. Can you elaborate on what are those three aspects?
Steph: Sure. So, the article, and thank you, for reading it, is about, I was a leader for around a year and a half at Toptal. Prior to that, I had many bosses, and I had this perception of what may be, a good leader was.
And then I think that actually changed when I became a leader, and I realized there was all these misconceptions of leadership. I had also, like, because I entered a leadership role very early on in my career and at a young age, especially compared to some of the people I was leading, I had to force myself to actually figure out, like, people won’t just assume that I’m a good leader. If anything, they will assume I’m a bad leader based on my age, and my experience. And so I needed to really try at least, to distill what actually makes a good leader.
Like, I don’t care about these listicles that you see online that say, like, “You need to have strong conviction,” or, “You need to have X many years of experience.” It’s like, well, I don’t have that experience, so let’s figure out, like, what are the, like, from first principles, what makes a good leader?
And the three things that I came to, throughout my year and a half, which I do still believe in, the first one is have humility. The second one is to, basically, like, scrap any, sort of, agenda that you might have. And the third is to lead through influence.
I’ll quickly go through what I mean by each of those. The first one, having humility, I think is really important. I think, especially if you’re a new leader, or you’re not going to be assumed to be a good leader, you can potentially, want to fall on this concept of proving that you know everything, or trying to show that you are a confident leader and people should trust that.
But I think what, actually, is more important is, like, humility is not about saying that you’re bad at something, it’s having, like, an accurate point of view of your abilities. So, I think that’s super important, and that you don’t need to act super confident, and you don’t need to act like you don’t know anything. You should portray your actual level of ability. And you should be very okay with the fact that there will be gaps, and there will be gaps even if you have had decades of experience in the past.
So, I think the big pitfall, for many people, is when they do try to fake some level of confidence, you’re basically, like, breaking some sort of trust between your team, because realistically, they know, you know, or they will find out as they work with you, that whatever level of confidence that you’re faking is not actually proportional to your ability.
So, that’s negative, in that you’re reducing that trust, but it’s also negative for you as a leader, because if you’re acting ultra confident, you’re actually shielding yourself from the ability to improve yourself, or to seek feedback so that you can actually become the leader that you hope to be, or to actually match that confidence with the level of ability.
So, I think that’s really important. And again, I think it’s especially true with people who, like, are new to leading, like myself at the time. You can almost want to exude this level of confidence, but I think it’s actually, really detrimental in the end.
The second one is this idea of scrapping your agenda. I just think most of the time, the arc for a lot of people who go into leadership, they used to be an individual contributor, now they’re leading other people.
When you’re an individual contributor, you more so are focused on your own progression, your own career, and all these things. And then when you become a leader, you have to completely untrain yourself from that, and actually, prioritize your team’s success, and their careers, and all these things.
That sounds very obvious, but it’s actually, like, I think still, many people who are leaders have some sort of agenda, whether they realize it or not, where it’s like they want to be promoted again, or they want their team to be seen as, like, the best in the organization, and all the stuff, regardless of how it actually impacts people within their team.
So, I think again, it’s about demonstrating your character, in the sense that you are actually prioritizing people on your team, even in tough situations. So again, going back to what I mentioned, like if there’s someone on your team who, in theory, is a really good individual contributor that makes your team look good from a purely output standpoint, but is actually causing a lot of problems internally, some leaders will opt, because it’s better for them to actually keep that person because it makes them and their team look better. But I think if you really do scrap any sort of agenda, in that situation, you would need to remove that person from the team.
The third one is leading through influence. So, there’s this concept of, like, the difference between leading and managing. I think one of the keys in differentiating someone who’s a leader or manager, is that one you’re, like, inspiring them through influence. But the only way I think you can inspire a team through influence is by actually also knowing what the team is doing, like, actually having the skills and actually, like, being in there with them.
And so I think sometimes, companies will hire people with, like, again, like, piles of experience. They’ll bring them in. And these people, basically, are just, like, managing downwards or upwards. I think the best leaders are people who actually, if they needed to, like, if someone was on vacation, or someone was, you know, sick or whatever, that leader could actually fill that role. They know enough about what’s going on, and they have the skill set, that they could actually replace anyone on the team, if need be.
That’s actually, like, surprisingly rare, but I think in order to actually again, be a good leader, empathize with them, be really, in the weeds with them when need be, it requires that you have that level of understanding.
Anyway, the key takeaway of that article is that I think there’s all this leadership fluff flying around about what makes a good leader. I think, honestly, if you cover those three things, you have humility, if you really do prioritize your team over yourself, and you actually do have the skills in order to lead with influence, you are probably the top, you know, 10% or whatever, of leaders, in my opinion, even if you don’t have 10 years of experience or some of the other things that you’ll read online.
Jovian: In that article, you have this one line that you wrote that says, “You know what says ‘I’m the boss’? Literally being a boss at what you do, not what you say.” I think it’s a very badass line.
Steph: Yeah, thanks.
Jovian: It is very badass. I’m going to put it on my Twitter right now. So, as I was reading this and also listening to you just now, one thing I think about humility, because I 100% agree, that I think humility is super important to be a great leader, or even a good leader, so to speak.
But I wonder if this is something that people can create? It’s similar to my previous concern about being a better communicator, or what I say? Oh, about empathy. So, I think it’s one of those things that people will think either you’re humble, or you’re not. Like, I’ve never seen people, “Okay, my goal in 2020 is to be more humble.”
But again, like, we talked about here, humility is super important to be a leader. So, how can leaders start working towards this, intentionally? Again, “Okay, I want to be more humble.” Well, in your opinion, what’s the best way?
Steph: Yeah, it’s a good question. I think there’s, I guess, two parts of my answer. The first one is that I think it takes the awareness and almost, like, coming to terms with the fact that being imperfect or, like, not knowing things, is okay. Actually, some of the best leaders are quick to admit that they don’t know everything, and that, you know, there are these gaps in their understanding.
But I think a lot of people, again, limit themselves to even get to that point, because they want to believe that they’re great, and they think that, like, being great and being wrong are mutually exclusive. You can still be very intelligent, a great leader, all these things, and be wrong sometimes. In fact, everyone will be wrong, sometimes.
So, I think it first comes from that, but then also, putting yourself in situations where you can be wrong more often. Like, the reason that I think I have developed a sense of humility is because I have learned, from experience, that I’ve been wrong a bunch of times, whether it’s something small, like I remember back when I was on the growth team at Toptal, I used to, at the beginning, think I had…I would always know what ad copy would work the best. I found out very quickly that, like, I was wrong of a lot, like, more often than normal. And that’s something very small, right?
But putting yourself in situations where you can, like, learn that you are wrong a lot. And also, if you just, like, look around you, I think you’ll notice that most people don’t know what they’re doing. I’m not saying that in, like, with judgment, I just, throughout time have recognized that most people are just figuring things out.
So, the more you, like, put your eye on that, and also very clearly acknowledge, like I did with those ads, or like I’ve done in many other situations in my life, like, I was wrong. As you do that, I think you do develop a level of humility where you’re like, “Maybe I do think I’m still super smart and whatever, but I’m also wrong a lot.” That humility puts you in, hopefully, the right space, where you have a sense of when you might be wrong, or at least you know that you could be wrong in certain situations.
That’s what humility is. It’s just trying to get to a point where you have a more accurate sense of your actual abilities, versus some deluded sense, where you’re always right.
Jovian: Yeah, that’s a fantastic insight. I also want to add a bit. So, based on my observation, like, the best leaders are those who admit when they don’t know something, or when they wrong about something.
But you can see that there’s a core to this, to the action that he or she takes. That there’s a conviction. So, it’s like, “Okay, I’m rolling this like I don’t know this, but I know, like, and the high level thing is this is the way that we’re gonna go. But we might be wrong on the tactics.”
Because I feel like when you don’t have that, like, core belief, team members can be, like, “Okay, you don’t know this, and you don’t know where you’re going.” There’s a like…
Steph: I see your point, yeah. Well, I think it’s important to, yeah, to be very specific about where your confidence is, right? Not just have this, like, broad confidence of, like, “I know everything, we are going to be successful.” I think that can be inspiring at times, but I think it can actually be, like, really uninspiring at times, because people are like, “This seems super fake. I don’t think this person actually knows what we’re doing.”
You can, for example, I think it’s great to have, as a founder, for example, to have, like you said, a lot of confidence in a vision, right? Like, “I think this is the future. We’re creating something that’s meaningful, that’s going to impact people. But we’re gonna drop the ball a lot along the way. Like, right now we have certainty in this area, but maybe not this area. But we’re gonna find out, and we’re gonna use data, and we’re gonna do X, Y, Z to get there.”
So I think you make a really good point that you need to be very specific about where your confidence lies, or where it doesn’t, and not just be, like, hyper-confident or hyper-unconfident. It’s more about just like, again, having, like, a closer sense of reality, that you not just have yourself but portray it to others so that they understand where you stand. And they can get behind you if you have confidence where you actually have the skills to match up that confidence.
Jovian: Yeah, absolutely. Like, North Star should be clear enough for the team to see, even though the path isn’t clear.
So, yeah, so related about, you know, leadership. Leadership is a lot about making decisions, just like we talked before, like, what copy to write, what campaign should we run, how do we go about these product decisions? Making tough calls, basically. I’m just curious from yourself, how do you go about making decisions? Do you have some decision-making framework, when you’re leading a team, or even in your daily life?
Steph: Yeah, I mean, there’s all these decision-making frameworks out there. I think some are good, some are not so good. I don’t have one that I use religiously, but I think with anything I do, I’m a very analytical person, almost too much. I wrote a love letter to myself that many people have made fun of me for.
But I think with anything, you should use data. I use data, not just in classical senses where you’re, like, you know, setting up dashboards for ads, but also, like, when I was learning to code, I tracked every single day, what was I learning, how much?
Because I think, again, even though I try to be very, you know, accurate in my level of confidence, I’m wrong all the time. The only way that you can really come closer to a sense of reality, whether it’s in your confidence, or whether it’s in your progress on a project, is having some sort of data. Like, data doesn’t lie. We lie to ourselves with stories.
And so the best way that, you know, whether it’s…like when you’re creating your own decision-making framework, I think the only thing that I would say that needs to be true is there needs to be data in there, of some sort, to actually guide you in the right direction. Because again, we think we’re very pragmatic thinkers, but often, I think most people are actually not.
Jovian: Yes, I agree. So, in your previous job, you were in a situation where you felt like you were “leading too much.” But you were like, you find your skill, it’s like you haven’t used it for too long and you see your skill, your actual skills, declining.
I have this hypothesis that a lot of startup founders feel like this when their team is growing, like, you know, when you come to 10 people and they’re 50 people, and they miss being hands on with the work, whether it’s a product, or marketing, or even sales.
So, I feel like it’s a more common thing that, basically, those startup founders are less happier as the team grow, because they just miss, like, doing the “dirty work.”
In your opinion, do you think founders can find a balance between the two, or should they try to shift their mindset, or try to focus their minds to fully accept that their job is now to lead? A while ago, Jason Fried from Basecamp, I think he’s more on the latter part of it. Like, he felt like his design skill isn’t as good as before. And he’s okay with it, he accept it. My duty is as a CEO, he’s still with the company. I wonder if there’s any middle ground between these two, in your opinion.
Steph: It’s such an interesting question, because I’m not sure there’s a correct, like, all fits one solution to this, but I have a couple of thoughts on this. So one, I think the answer may be different if you are a founder, versus someone who’s just, like, leading a team within a company that’s not your own.
If you’re a founder, I do think there’s an element of, like, growing up with your company, right? You know, you started out and things are super scrappy, but you still, like, love the vision of your company, and you want to see that through, you know, to whatever size it grows to. When that happens, inevitably, your role will change very significantly.
But I do think there’s an element where that’s, like, interesting, because you are growing up with your company, and whether like with Jason seems like he used to design and now he’s a CEO or a co-founder, and he’s okay with that.
However, there are cases where you do have to just decide what you care more about. So for example, actually, at the “Hustle,” I think this is okay for me to share, but Sam, for example, Sam just loves building things. That’s why he built the “Hustle.” He loves being scrappy. He loves taking a project from the stage zero to, you know, maybe stage five, and then someone else can take it from stage five to 100, right?
And so he actually has given up some of his, like, CEO-type responsibilities to our president, Adam, because of that reason. He’s just acknowledged, like, “I’d rather be doing certain other things. Actually, I’m probably not even the best person to be doing some of those more administrative-type responsibilities.” And so he’s okay with that.
But I think what’s important there is, like, you making the decision that’s best for you and for the company. Because I think a lot of people will make this type of decision specifically, whether they realize it or not, based on some level of pride. I say that because even when I was leading a 20-person team, and I was, you know, getting reached out to as being this leader in remote work and all this stuff, and it felt really good, I didn’t really enjoy the role.
But it came to a point where it’s like what are [inaudible 00:38:02] prioritized, PPS is, like leader in remote work, or doing things that I actually really love. And then I realized it doesn’t need to be, like, one or the other. Like, I can still write about remote work, I can still be involved in the community, but also just focus on skills that I, personally, am more drawn to.
So, it really didn’t feel natural, but I really had to separate myself from this, like, role and the title, and all the stuff that made me feel good, and focus on, like, what I actually wanted to do.
So, I guess the answer that I would say is I think founders can find a balance, but it depends on what they truly care about, and how much of what they’re doing currently is something that they do want to grow into or not.
And if it’s really something that they don’t want to grow into, I would probably say that, you know, they should do something like Sam has done, or they do, like, even though it maybe feels unnatural, give up some of that responsibility to someone who may be does it better, and I’m not speaking about Sam in this case, but you know, someone who wants to do that particular set of responsibilities.
Jovian: It also ties back to the point of humility that we discussed earlier, because you have to know what you’re not good at, and what doesn’t energize you. And then you should be okay to delegate it to other people and let them take their credit, basically.
Steph: And it ties to the thing we were talking about earlier, as well, where there’s that arc where people are individual contributors, and then the next natural step is manager. People feel like in order for them to advance in their career in some way, they need to be in that management role. It feels very unnatural, and if anything, like someone is taking a step backwards, for them to be in a management role and then step back to an individual contributor role.
It did feel very unnatural, but I think if you’re focusing less on that pride and less on the storyline of, like, how your career should be, you can then just design it around, like, what you actually want to be doing, and what, yeah, like you said, I like the word, like, what energizes you?
Jovian: Yeah. Yeah, I absolutely agree with what you say, especially when the story that you tell yourself, right? It doesn’t have to be like that. It should be focused on what you like most, especially, I feel like when it comes to remote work, that this kind of thinking is more, how do you say it? Is more common, nowadays.
Steph: Mm-hmm.
Jovian: Because it’s more about how you can contribute, instead of title of climbing the corporate ladder, it’s less about that. Even though a lot of remote companies [inaudible 00:40:44] structure.
Anyway, talking about authenticity, and this is something that, like, authenticity, creativity, it is something that I’m very interested about, especially when tied back to remote work. So, starting with productivity and personal growth, so when you started working remotely, it took you a while to adapt your habits. It took you three to six months. Can you share a bit more about the process, and what are the things you remind yourself every day to get used to the flow of working remotely?
Steph: Yeah, so it did take me a while. Now, I don’t necessarily need to, like, remind myself of certain things, just because I’ve been doing it for many years. If anything, I think I’d have to, like, train myself out of working remotely, if I ever chose to switch.
But back then, it was really interesting to switch from a very structured in-person role, or non-remote role, to one that was completely remote. I switched to Toptal, which was a completely remote organization. So, they really embraced a lot of the core remote values, which is, like, “I don’t care what hours you’re working. I don’t care, you know, if you…” For example, I remember my first week, I had a dentist appointment and I like, warned my boss. I was, like, “I’m gonna be out for exactly these hours,” and he was just like, “Okay, cool.” But he really didn’t care.
Now if, you know, like when I lead a team, like, someone would do that with me, and I genuinely don’t care, not because I don’t care about their life, but just like, that’s fine. Like, go to your dentist appointment, go pick up your kids. Like, that’s great. I don’t care how your day-to-day actually looks. I just care that you’re contributing, you know, to the team and doing your work.
So, that took me a really long time to digest and actually internalize. And for that reason, especially in the first, while I was still working, like, pretty structured hours, and I didn’t really understand how to optimize my time, I was still doing a lot of things just to look like I was doing things.
I mean, I was productive during that time, but it was just, like, I wasn’t really wiping the slate clean and saying, “Okay, ignore, like, how many hours you’re working, or when you think you should be working, how do you actually, like, design your schedule, so you’re more productive, and so that you’re only working on the most high impact things?”
It really did take three to six months for me to rejig and really just design my own schedule, so that I could work more optimally. So, yeah, I think it’s just that, especially if you’ve worked, I only worked in an office for a year. So people who have worked in an office for a couple of decades, I think it might take even longer to really get accustomed to remote work. I think in certain cases, some people, it just doesn’t work for them. Like, their habits don’t really line up to remote work, and that’s completely fine.
But yeah, to answer your question, it really just took time to almost, like, unlearn the things that I had learnt in a prior role, and think about things in a way I was just designing them from the ground up.
Jovian: Mm-hmm. Yeah. Yeah, it’s really hard to. So, I’ve been working remotely, actually very recently, like, a bit more than half a year. So, yeah, it does take some adjusting at the beginning, but in the end, I feel like even right now, no, I cannot go back to the office anymore. So yeah, ironically, I’m doing this podcast in Arc’s office in Taipei, as you can see the logo behind me.
Steph: That’s great.
Jovian: I don’t have the space to record a podcast in a quiet room. Have you ever been to Taipei?
Steph: I have. My mom is, actually, from Taipei.
Jovian: Oh, really?
Steph: Yes, so I’ve been there, maybe three or four times. But only for, you know, a week or so each time.
Jovian: Yeah, Taipei is a great place. I always say to people, Taipei is a great place to live. Not necessarily a great place to, like, short term traveling, like, a week.
Steph: Yeah. I think most big cities are like that, I would say, actually. Like Toronto is, that’s where I grew up, and I would say the same thing. I’m happy that I grew up there, but whenever I hear people coming to Toronto as a tourist, I’m very surprised, because I just don’t know what they would do.
Jovian: Right. Right, right. So, another topic I wanted to touch is, like, still related to personal growth and remote work. Like I mentioned in the beginning, you are a very prolific writer and maker. You wrote this amazing piece about learning to write with confidence, which it doesn’t only touch about the subject of writing itself, but also the creativity part of it, and the mentality of making something.
I always think that one of the benefits of remote work is how it provides the headspace for one to do more creative work, in general. I’m saying this from a personal experience, just when I started working remotely, there’s, I can’t articulate this real well, but there’s some, a switch that basically, you like distance yourself from the hectic day-to-day stuff, and you can see things in a different way when you’re out of office. This triggers this creativity.
I feel like because remote work becomes more common, that’s why creativity will be, my hypothesis is that people would be more and more creative, because they have the headspace and the flexibility to do what they love.
It’s also related to what we talked about, you know, creating something, but giving to the world first, and how it can help when you’re looking for a remote job in the future. Like, the proof that you have created something.
Now, I want to dive in a little bit into how you personally find and absorb creative ideas in your mind. Do you have any particular habits or processes around that?
Steph: So, I think you make a really good point of saying that remote work is really great, in that it helps you facilitate a more creative outlet, just because it gives you the freedom to design your life in a way that you make room for that.
And so in my old job, when I wasn’t working remotely, my life was very, like, blocked, and that if, like, during, you know, nine till seven or whatever it was, I was at the office, I was thinking about just that, for that amount of time. And when you think about it, in many cases, that amount of time, for me, it was like 10 hours a day, if not more.
By the end of that period, you’re really tired and you don’t really have…you know, some people think there’s like, maybe somewhere between two to four hours of really creative, thoughtful work that you can do in a day. That’s completely drained by the end.
So, I don’t know if I have any particular habits to stimulate creativity, other than making time for it and making sure it’s not just that end of the day type thing that you’re inserting, because, like, that’s the only time you have for it when you work remotely. I think it’s really important to design your schedule very intentionally.
Actually, it’s funny, because when people hear me talk about this, they think I’m a very organized person. I’m actually extremely unorganized, from a stereotypical standpoint. I don’t schedule anything. I don’t put time on my calendar. I know many people do that. But I just make sure to give time to different things that I care about, and that includes my creative pursuits.
And then the other thing that I think is so true, and a lot of people miss, is that when you start creating things, it naturally creates an environment where you become more creative, and you get more ideas, and you become better at the creative process.
Like, a lot of people think that there’s creative people, or not creative people, or that, like, that’s something that is almost, like, an inherent trait. Creativity is a muscle that you flex as you create things. I saw that very strongly with most of my projects when I started learning to code and creating projects. As I created those projects, I’d come up with new ideas for new projects, and also just thought about things in a different way. And the same thing with my blog.
So, I think that’s really important is that one, you just make time so that you can create stuff. And then as you create stuff, you’ll be surprised that you’ll become more efficient at creating things, but you’ll also become, like, inherently, more creative as you put time towards that.
Jovian: Got it. I totally love your insight on this. So, I think that’s a good place to end this episode. Steph, thank you so much, for your time today. I really learned a lot. How can people find you online?
Steph: Yeah, so you can find me online. My site is stephsmith.io, and my blog is blog.stephsmith.io. And then also the place where I hang out the most is probably on Twitter, so my handle is @stephsmithio.
So, if people wanna reach out or jam me and have any questions, definitely, feel free to. But yeah, thanks so much, for having me on the episode. This was really fun.
Jovian: Yeah, so for the listeners, you can find Steph’s blog and Twitter on the show notes, along with the articles that I’ve mentioned here, and of other Steph’s site projects. Okay. Thank you, Steph.
Steph: Thank you.
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