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Listener Question: Can I Lead Remotely? (part 1)

Summary

This episode addresses a listener’s question about whether it’s feasible to pursue a leadership career path while working remotely. The listener expresses concerns about building personal culture, mentoring, and conducting practices like pair programming and stand-up meetings in a remote setting.

Jonathan begins by affirming that remote leadership is indeed possible, citing the existence of fully distributed companies and teams. He explains why software development is particularly conducive to remote work: talent is distributed globally, hiring remotely can be more cost-effective, and the digital nature of the work (code) transfers instantly. He also notes personal reasons why developers might prefer remote roles, such as avoiding family relocation.

The core of the discussion breaks down leadership into several styles to show which aspects are more or less affected by physical distance. Technical executive leadership (setting standards, choosing tools) is largely unaffected. Group dynamics leadership (structuring teams, pairing people) requires knowledge of personalities but can be done remotely. Principled leadership (leading by example) can cascade through an organization regardless of location. One-on-one mentoring, which the listener specifically worried about, requires consistent and predictable access, which Jonathan suggests can be achieved remotely with intentionality.

Finally, Jonathan outlines three scenarios where remote leadership tends to work well: when distribution is already part of the team’s DNA (everyone is remote), in contractor-heavy roles where relationships are shorter-term and goal-oriented, and in teams with a well-defined, predictable rhythm where remote tools can effectively bridge the gap. He promises a follow-up episode with practical tips for being a great remote leader.

Topic Timeline

  • 00:00:00 — Introducing the listener’s question about remote leadership — Jonathan introduces the episode’s topic: a listener’s question about whether it’s possible to be a leader while living thousands of miles away from team members. The listener, who wishes to remain anonymous, is considering a career path toward becoming a tech lead or senior developer but is skeptical about how personal mentoring and team culture can work remotely. Jonathan reads the listener’s email, which expresses doubt that leadership can work solely through tools like Slack and Skype.
  • 00:02:16 — Affirming the importance of relationships and introducing the answer — Jonathan starts his response by affirming the listener’s focus on personal involvement and empathy, calling it “where leadership begins.” He then gives the direct answer upfront: yes, remote leadership is possible. He mentions that there are fully remote teams and companies. He sets the stage to dive deeper into the specifics of the question, starting with why software development as an industry is particularly inviting for remote work.
  • 00:03:17 — Why software development is conducive to remote work — Jonathan explains several reasons why software development is one of the most remote-friendly industries. First, talent is distributed worldwide, expanding the hiring pool. Second, hiring remotely can be more cost-effective for companies, avoiding relocation expenses. Third, developers may prefer remote roles to avoid uprooting their families or leaving their communities. Finally, the work product—code—is digital and transfers instantly, making the actual work naturally suited for distribution.
  • 00:05:48 — Breaking down different styles of leadership — Addressing the core concern about leadership being relational, Jonathan breaks leadership into several styles to analyze their remote viability. He discusses technical executive leadership (making technical decisions, setting standards), group dynamics leadership (structuring teams, managing interpersonal pairings), and principled leadership (leading by example, establishing values that cascade). He notes that much of technical and managerial work can be done remotely, while relational aspects like one-on-one mentoring require consistent, predictable access, which he will discuss further.
  • 00:12:40 — Scenarios where remote leadership works well — Jonathan outlines three situations where remote leadership is most feasible. First, when distribution is already part of the team’s DNA—if everyone is remote, a remote leader fits naturally. Second, in contractor-heavy roles where relationships are shorter-term and more goal-focused, requiring less deep relational investment. Third, in teams with a well-defined, predictable rhythm; consistency and predictability can compensate for the lack of physical closeness, allowing remote communication tools to build strong leadership relationships.

Episode Info

  • Podcast: Developer Tea
  • Author: Jonathan Cutrell
  • Category: Technology Business Careers Society & Culture
  • Published: 2017-03-15T09:00:00Z
  • Duration: 00:19:04

References

Podcast Info

Transcript

[00:00:00] Can you lead someone when you live thousands of miles away from them?

[00:00:09] That’s the question that we’re going to answer in today’s episode.

[00:00:13] My name is Jonathan Cottrell and you’re listening to Developer Tea.

[00:00:16] I’m excited to jump into today’s episode, which is actually a question from a listener

[00:00:21] who requested to remain anonymous and partially because this person is thinking about a career

[00:00:28] change.

[00:00:28] Of course, you can ask questions to me and if you want to remain anonymous, I won’t reveal

[00:00:34] who that question came from.

[00:00:37] So that’s exactly what we’re going to do today.

[00:00:39] We’re going to cover this question and I’ll go ahead and read this email.

[00:00:42] Obviously, it’s been changed slightly to remove any identifying information.

[00:00:47] So let’s jump straight into today’s episode.

[00:00:50] The listener writes in and says, I’ve been thinking a lot about the future path for my

[00:00:55] career.

[00:00:56] And I came to the conclusion that I’d like to be a developer.

[00:00:58] I’d like to become a tech lead or at least a senior with his own responsibilities.

[00:01:04] That includes mentoring and personal care of my co-workers and especially juniors and

[00:01:09] trainees.

[00:01:10] The concept of remote positions or even completely remote and distributed teams and companies

[00:01:16] seems to be quite strong in the development industry.

[00:01:20] But I can’t grasp how a personal culture and especially a personal mentoring or things

[00:01:26] like peer programming and stand-up meetings.

[00:01:28] Might work in a remote scenario.

[00:01:32] That’s most likely because I never had any direct contact to a distributed software company

[00:01:38] or talk to anyone who was employed remotely full time.

[00:01:42] So here’s my question.

[00:01:43] Is it even reasonable or feasible to plan to be remote to interview for remote positions

[00:01:49] with my career plan?

[00:01:52] One company even explicitly offered me a home office as the day-to-day default when

[00:01:58] offering me a remote position.

[00:01:58] But I don’t see how this would work out.

[00:02:03] This cannot be working only via Slack and Skype and phone, can it?

[00:02:08] I know you’ve talked about remote work before, so I hope you can find some enlightening words

[00:02:12] for me.

[00:02:13] Thanks in advance.

[00:02:14] Signed, Anonymous.

[00:02:16] Well, first of all, let me start by saying you have your head in the right place.

[00:02:20] Personal involvement with the people you are leading is incredibly important.

[00:02:24] And having empathy and respect for the relationships,

[00:02:28] themselves, that’s where leadership begins.

[00:02:32] Servant leadership isn’t just a buzzword.

[00:02:35] It’s how leadership works.

[00:02:37] It’s what leadership really is.

[00:02:39] So now let’s talk about some of the questions more in depth and discuss scenarios where

[00:02:43] remote work could work out for leadership.

[00:02:46] And that’s really the first answer.

[00:02:48] I’ll go ahead and ruin the rest of the podcast if you’re hanging on a thread here wondering,

[00:02:53] can I be a leader and be remote?

[00:02:56] The answer is yes, it is possible.

[00:02:58] There are definitely teams that have remote leadership.

[00:03:02] And on top of that, there are teams that are 100% distributed, 100% remote.

[00:03:08] There are companies that are 100% remote.

[00:03:10] So we’re going to talk about some of this stuff, but I want to dive into a few of the

[00:03:14] things that you mentioned in this question.

[00:03:17] The first thing that you mentioned, software development is one of the most remote inviting

[00:03:21] industries in the world.

[00:03:23] And that’s for a few reasons.

[00:03:25] Obviously, talent is distributed worldwide.

[00:03:28] There are people who are doing it.

[00:03:28] There are people all over the world who have talent as software developers.

[00:03:33] Thus, the hiring pool is necessarily worldwide.

[00:03:37] If you’re looking to build a team of people who are truly talented, then opening up your

[00:03:42] possibilities to the whole world, or at least to an entire country, for example, that can

[00:03:48] greatly increase the quality of the workers that you have on your team.

[00:03:52] Finding talent, especially if you’re looking for specialists rather than generalists, finding

[00:03:58] that talent.

[00:03:58] Is much more likely, you’re much more likely to find a fit if you select from the worldwide

[00:04:04] or even a nationwide audience.

[00:04:06] In many cases, it is directly more cost effective to hire someone remotely than it is to hire

[00:04:13] them and also pay for them to move.

[00:04:16] And there’s a lot of reasons for this.

[00:04:18] Some of them have to do with cost of living.

[00:04:20] Some of them have to do with the actual relocation costs.

[00:04:23] A lot of times people are going to be willing to take a different salary.

[00:04:28] If they can stay where they are, there’s a lot of reasons for this.

[00:04:33] For example, you may not want to uproot your entire family.

[00:04:36] If you have a family and you find a job in a different city, well, moving your family

[00:04:42] to a different city can be an emotionally and financially stressful process.

[00:04:47] But if you can stay where you are, that can be hugely beneficial to your family life.

[00:04:53] Of course, friends and culture make a huge difference on these metrics as well.

[00:04:58] So.

[00:04:58] A lot of reasons why people personally want to stay where they are, even if they find

[00:05:03] a job in a different city, and that can make it financially beneficial for the companies

[00:05:09] that are hiring remote and transferring the work itself, right?

[00:05:13] The actual code, it’s nearly instantaneous, right?

[00:05:17] That’s part of the reason why software development is one of the most remote inviting industries

[00:05:22] in the world, because transferring the work from one person to another, you don’t have

[00:05:26] to wait on it to ship across the country.

[00:05:28] Because the transferring is all done digitally.

[00:05:32] So it’s incredibly powerful because this type of work lends itself to distributed companies

[00:05:38] because it itself, the work itself is distributed, right?

[00:05:44] So it makes sense that software development would be distributed.

[00:05:48] Now, if leadership is primarily a personal and relational endeavor, how can one be a

[00:05:54] leader when working in isolation?

[00:05:55] This is really kind of the email sum.

[00:05:58] If leadership is primarily a relational thing, if it’s, if it is primarily how I can get

[00:06:07] to know you as an associate developer, then how can I do that?

[00:06:12] How can I develop good relationships, deep relationships remotely?

[00:06:18] Well, first we have to start by identifying the fact that there are many different expressions

[00:06:22] of leadership that you will take on in your career.

[00:06:26] And there’s different times.

[00:06:28] Where each of these expressions is going to be more important or more pronounced than

[00:06:33] the other.

[00:06:33] So for example, technical executive leadership, this is the most common type of leadership

[00:06:40] for lead developers, because really all we’re talking about here is actually reviewing code

[00:06:47] and developing the standards that your team is going to follow, right?

[00:06:51] Deciding what types of frameworks or what languages you’re actually going to use.

[00:06:58] The actual technical leadership, making decisions, making executive decisions in the technical

[00:07:04] space, writing and talking about those standards, about those decisions and justifying why you

[00:07:12] chose those things.

[00:07:13] These are all parts of leadership that are not necessarily directly relational, but they

[00:07:20] may be a large part of your job as a technical leader.

[00:07:24] And you can absolutely execute these things remotely.

[00:07:28] There’s nothing to keep you from evaluating a tool remotely.

[00:07:33] Another type of leadership you will encounter, group dynamics leadership.

[00:07:37] This is when you are leading the structure of a group, managing the interpersonal aspects

[00:07:44] of, for example, team pairings, pairing two or three programmers together, pairing a programmer

[00:07:49] with a designer, or pairing a front-end programmer with a back-end programmer, putting the right

[00:07:55] people on a project together, right?

[00:07:57] And what you’re doing is you’re putting the right people on a project together.

[00:07:58] And while this requires a pretty extensive knowledge of the personalities of the people

[00:08:02] on the team, the practice itself is equal parts managerial and relational.

[00:08:08] So a lot of what you do when you’re managing a group, you can do remotely.

[00:08:15] Another type of leadership that you’re going to encounter is principled leadership or leadership

[00:08:21] by example.

[00:08:22] This is setting forth ideas that others elect to follow without necessarily,

[00:08:28] developing a personal relationship with them.

[00:08:31] And this is pretty much never because you don’t want to develop the relationship or

[00:08:35] because it’s a hassle, but rather it happens when companies scale.

[00:08:40] Leadership may not necessarily have a direct relationship with all of the associates in

[00:08:45] the company, but their examples and the values that they subscribe to, the things that they do,

[00:08:52] those values will have a cascading effect on the people that they lead.

[00:08:58] And you can see this when you have a company that has multiple locations and still has a leader

[00:09:04] that stays in basically one location.

[00:09:07] My guess is the person who sent this email in, my guess is that you’re not going to get into

[00:09:13] this scenario anytime soon, but that may be eventually kind of a model of leadership that

[00:09:19] you will follow is developing patterns, developing values, developing examples that you can lead

[00:09:26] by example.

[00:09:28] You can act out what you want the people that you lead to do in their own careers or to do with,

[00:09:37] for example, the code they write.

[00:09:39] Another type of leadership, and this gets more into the relational leadership that you’re talking

[00:09:44] about, is one-on-one mentoring.

[00:09:47] Mentoring is a huge topic that we can’t cover in one episode.

[00:09:51] Mentoring is not just having a relationship with someone who you think is better at something.

[00:09:58] You are in having coffee every other week with them.

[00:10:01] That’s not the totality of mentorship.

[00:10:04] Mentorship is a much more involved topic than we can cover in a single episode.

[00:10:10] But one of the most important parts of mentorship is reasonable and predictable access.

[00:10:17] And we’ll talk a little bit more about this later on in today’s episode.

[00:10:20] But that simply means that those you are mentoring have a way to be personal with you

[00:10:25] on a consistent and predictable basis.

[00:10:28] If you are a mentor, if you are leading another developer directly, if you have a relationship

[00:10:35] with another developer, you need to have a consistent touch point.

[00:10:40] You need to have a consistent time where you are spending one-on-one energy with that person.

[00:10:48] Now, whether you do this remotely or in person doesn’t always make a huge difference in the

[00:10:55] quality of those meetings.

[00:10:56] We’re going to talk a little bit more about that in a little bit.

[00:10:57] We’re going to talk a little bit more about that in a little bit.

[00:10:57] We’re going to talk a little bit more about how a remote mentoring relationship would

[00:11:02] look like in a secondary episode, a follow-up episode to this episode.

[00:11:08] Again, this is a huge topic and we can’t cover it all in one episode.

[00:11:13] So there’s all these different types of leadership or styles of leadership, aspects of leadership

[00:11:19] that you’re going to encounter as you move forward with your career, especially if you

[00:11:23] want to become a leader, right?

[00:11:25] So often when we think about leadership, we think about leadership as a type of leadership.

[00:11:27] And when we think of leadership, we forget one of the things that I listed above, or

[00:11:32] perhaps we only focus on one of the things that I listed above.

[00:11:37] But in fact, it is all of the above and much, much more.

[00:11:41] Of course, I haven’t covered all of the aspects of leadership in today’s podcast.

[00:11:45] Hopefully you know that.

[00:11:47] It’s important to understand when and how different parts of your responsibilities as

[00:11:51] a leader will be affected by your physical location.

[00:11:55] There are times.

[00:11:57] When it will be, and there are times when it won’t be.

[00:12:00] For example, a lot of the technical work that you will do as a leader is relatively unaffected

[00:12:06] by your location.

[00:12:08] Assuming that you have some kind of cloud-enabled version control system that you and your team

[00:12:13] use on a regular basis, you probably have access to the code you need and you can push

[00:12:20] it to the servers for others to have access.

[00:12:23] And it’s likely that that process is followed no matter where you are.

[00:12:27] If you’re in the office or out of the office, that you follow the same practice of pushing

[00:12:31] to that remote repository, for example.

[00:12:34] But there definitely are other aspects that can be affected by your location.

[00:12:40] So I want to cover when does remote leadership work well.

[00:12:44] And then in another episode, as a follow-up episode, I’m going to talk about what you

[00:12:49] need to do to be a great remote leader.

[00:12:53] I’ve got some really practical tips that will come in that follow-up.

[00:12:57] So I’m going to talk about what you need to do to be a great remote leader.

[00:12:57] But first, let’s talk about situations where remote leadership can possibly work.

[00:13:04] The first type of situation is if the distribution, if distributed work, is already a part of

[00:13:12] the DNA of your team.

[00:13:14] Let me say that again.

[00:13:15] If your team is already distributed, then it makes sense that your leadership is distributed

[00:13:22] as well.

[00:13:23] And the team is already primed for this concept.

[00:13:25] You’re going to notice that a lot of this is a part of the DNA of your team.

[00:13:26] You’re going to notice that a lot of this is about psychology.

[00:13:29] It’s about the pre-existing conditions of your team.

[00:13:33] And it’s important to understand what your position in that team is relative to what

[00:13:40] that team is used to.

[00:13:42] If you come in and you’re very different from everyone else, then obviously that’s going

[00:13:47] to be perceived as a change.

[00:13:49] And you’re going to have to deal with some of the side effects of change.

[00:13:52] So if distribution is already a part of the DNA of your team,

[00:13:56] if most of the relationships on your team are not co-located, then presence is not short-circuited.

[00:14:02] In other words, in the context of their professional relationships, if you can maintain equally

[00:14:08] present relationship to those you lead, as they already have with their other co-workers,

[00:14:14] it is much more likely that the quality of those relationships can be retained.

[00:14:19] So what are we saying here?

[00:14:20] Basically, we’re saying if you are going to be remote, it’s going to be easier if every

[00:14:26] one else on the team is also already remote.

[00:14:29] If you imagine a scenario where everyone else on the team is already co-located and you

[00:14:35] are the only remote person and you also happen to be their leader, well, that’s going to

[00:14:40] be a little bit more difficult to deal with, most likely.

[00:14:43] So again, remote leadership works well when distribution is already a part of the DNA

[00:14:48] of the team.

[00:14:50] Second example of when remote leadership can work well is in contractor-heavy leadership

[00:14:55] roles.

[00:14:56] This is very practical in contractor-heavy leadership roles.

[00:14:59] If your team is made up primarily of remote contractors, in other words, the working period

[00:15:06] that they’re going to be working with you has a set end date.

[00:15:10] If they have a contract that has a set end date, and if contractors are coming in and

[00:15:17] going out of projects with your company, it’s likely that your relationship with those contractors

[00:15:22] is going to be shorter-lived.

[00:15:24] And the goals of the relationship?

[00:15:26] The goals of the relationship will be different from a longer-term scenario.

[00:15:29] If you don’t have a kind of a wide-open door into the future with the people that you are

[00:15:37] leading, then it’s going to be a lot easier.

[00:15:39] So this happens a lot of the time with freelancers, with contractors.

[00:15:43] They come on for a short period of time, and then they move on to a different project,

[00:15:48] perhaps with a different company.

[00:15:50] The leadership role in these scenarios is less about relationship.

[00:15:55] Now, don’t get me wrong.

[00:15:57] It is still about relationship, but it is less about relationship than when you have

[00:16:04] a much more involved longer-term relationship like you would in a non-contractor environment,

[00:16:11] like you would with a developer who is a salaried employee on your team, who is looking to learn

[00:16:16] from you, who is perhaps early in the industry, and they’re looking to build their relational

[00:16:22] capital.

[00:16:23] These are all scenarios where…

[00:16:25] Working remotely is going to have to have a lot more investment and a lot more intentionality

[00:16:31] from your part.

[00:16:32] So working remotely with contractor-heavy leadership roles, those situations are a little

[00:16:38] bit easier, a little less energy for the remote leader.

[00:16:43] And the third and final situation that we’re going to talk about where remote leadership

[00:16:47] kind of naturally works well is in teams that have a well-defined rhythm.

[00:16:52] And really, this is kind of the theme of…

[00:16:55] The follow-up episode, but in teams that have a well-defined rhythm, a large part of leadership

[00:16:59] and really anything dealing with any type of relationship is consistency, predictability.

[00:17:06] If you are inconsistent as a leader, it is extremely difficult for the people you lead

[00:17:13] to build trust and ultimately a sense of homeostasis, a sense of safety.

[00:17:19] When an employee feels a sense of chaos, closeness becomes even more important, right?

[00:17:25] If things are kind of out of whack, then closeness becomes really important.

[00:17:29] And closeness is harder to accomplish remotely.

[00:17:34] However, when an employee feels a sense of steadiness and predictability, remote communication

[00:17:40] tools can often stand in the gap well enough to build a strong leadership relationship

[00:17:45] with those employees.

[00:17:48] So here we’re going back to what we mentioned earlier, the predictable access that you should

[00:17:54] have if you are…

[00:17:55] If you’re going to be a remote leader, that’s going to be incredibly important for teams

[00:18:01] that want to develop a consistent rhythm, right?

[00:18:04] A well-defined rhythm.

[00:18:06] That means consistent access to you as the remote leader.

[00:18:10] We’re going to talk more about this topic of remote leadership in the next episode.

[00:18:15] Thank you so much for sending this in.

[00:18:17] Once again, the sender was anonymous.

[00:18:20] Thank you again to sending this in.

[00:18:21] If you have a question for me that you’d like for me to answer on the show, please reach

[00:18:25] out.

[00:18:25] You can reach me at developertea at gmail.com.

[00:18:28] Go and check out the other shows on Spec.

[00:18:30] Go to spec.fm.

[00:18:31] The show notes for today’s episode and every other episode of Developer Tea can be found

[00:18:35] on spec.fm.

[00:18:37] But more importantly, there are other incredible shows, for example, Does Not Compute, Orthogonal,

[00:18:42] Design Details, tons of other great shows that you as a designer or a developer or somewhere

[00:18:48] in between would definitely find interesting.

[00:18:51] So go and check it out at spec.fm.

[00:18:52] Thank you again for listening to today’s episode.

[00:18:54] And until next time, enjoy your tea.

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