Listener Question: Can I Lead Remotely? (part 2)
Summary
In this episode of Developer Tea, host Jonathan Cottrell continues answering a listener’s question about whether it’s possible to lead a team remotely. He acknowledges that while remote leadership is feasible, it requires specific strategies and mindsets to overcome the challenges of physical distance.
Cottrell begins by emphasizing the importance of being explicit about the value of remote work. Leaders must recognize and communicate the benefits of remote arrangements, such as flexibility, diversity of team interests and locations, time-shifted work schedules, and results-oriented efforts. He warns against treating remote work as handicapped or blaming remote arrangements for problems, as this creates resentment. Instead, leaders should focus on highlighting the parallel quality and advantages of remote work compared to co-located work.
The second critical tip is establishing a predictable rhythm. Cottrell distinguishes between habits (unconscious, situational) and rhythms (intentional, conscious). Remote leaders must create reliable patterns of availability, such as consistent daily schedules and punctuality for meetings and calls. This predictability builds trust and reliability, which are even more crucial in remote settings where casual, in-person interactions don’t occur naturally. He notes that while these principles apply to all leadership, they require more conscious effort in remote contexts.
Finally, Cottrell advocates for getting real face time whenever possible. He recommends bringing remote teams together in person once or twice a year, either at company headquarters or on retreats. These gatherings should include both collaborative work sessions and social time. Working together in the same space demystifies remote colleagues’ work habits and builds trust by creating shared memories. These anchor memories help team members visualize each other positively when they return to remote work, reducing suspicion and negative assumptions about productivity.
Recommendations
Newsletters
- Soft Skills Weekly — Jonathan Cottrell’s weekly newsletter curating approximately seven resources per week focused on soft skills, including conversations, articles, interviews, podcasts, and books.
Websites
- spec.fm — The platform hosting Developer Tea and other podcasts; mentioned as a place to search for past episodes about mentoring by using the search term ‘mentor’.
Topic Timeline
- 00:00:00 — Introduction to remote leadership challenges — Jonathan introduces the episode’s focus on whether it’s possible to lead a team remotely, acknowledging that leadership is relationship-oriented. He references a listener question from the previous episode about transitioning to leadership roles and the feasibility of remote leadership. The episode will provide practical tips for being a great remote leader.
- 00:01:33 — Recap of leadership types from previous episode — Jonathan recaps the three types of leadership discussed in the previous episode: technical/executive leadership (reviewing code, setting standards), principled leadership by example (establishing values at scale), and one-on-one mentoring (the most common and important type for listeners). He notes that mentoring is too complex to cover fully in one episode and directs listeners to past episodes on mentoring.
- 00:03:21 — When remote leadership works well — Jonathan discusses scenarios where remote leadership is effective: teams with distribution already in their DNA, contractor-heavy teams with fluid membership, and teams with well-defined rhythms. He suggests that most listeners likely want to build teams with clear rhythms, setting up the discussion of what it takes to be a great remote leader.
- 00:04:01 — Tip 1: Be explicit about the value of remote work — Jonathan emphasizes that remote leaders must understand and articulate the value of remote work, not treat it as invisible or inferior. Benefits include flexibility, diversity of team interests and locations, time-shifted schedules creating 24-hour momentum, and results-oriented efforts. Critically, leaders should not blame remote work for problems or treat it as handicapped, as this breeds resentment.
- 00:05:48 — Tip 2: Establish a predictable rhythm — Jonathan stresses that leaders must consciously establish rhythms, not just let habits form accidentally. For remote leaders, this means creating predictable availability (e.g., set daily hours), reliability, and punctuality for meetings and collaboration. This predictability is crucial because remote teams lack casual ‘water cooler’ interactions; leaders must intentionally create touchpoints.
- 00:08:47 — Tip 3: Get real face time with your team — Jonathan recommends bringing remote teams together in person once or twice a year. These gatherings should include both collaborative work sessions and social time. Working together in the same space demystifies remote colleagues’ habits and builds trust through shared experience. These ‘anchor memories’ help team members visualize each other positively when apart, reducing suspicion.
- 00:12:41 — Conclusion and key takeaways — Jonathan concludes by acknowledging the complexity of remote leadership and summarizing the core principle: consistency and availability, eliminating unpredictability, are key for remote leaders. He promotes his new newsletter, Soft Skills Weekly, and thanks listeners for tuning in.
Episode Info
- Podcast: Developer Tea
- Author: Jonathan Cutrell
- Category: Technology Business Careers Society & Culture
- Published: 2017-03-17T07:00:00Z
- Duration: 00:13:59
References
- URL PocketCasts: https://podcast-api.pocketcasts.com/podcast/full/cbe9b6c0-7da4-0132-e6ef-5f4c86fd3263/3729b75f-5c12-4f30-ac5e-fadf7ab5a0fe
- Episode UUID: 3729b75f-5c12-4f30-ac5e-fadf7ab5a0fe
Podcast Info
- Name: Developer Tea
- Type: episodic
- Site: http://www.developertea.com
- UUID: cbe9b6c0-7da4-0132-e6ef-5f4c86fd3263
Transcript
[00:00:00] What do you need to do to be a good leader if you are a thousand miles away from your team members?
[00:00:12] We’re going to talk about that in today’s episode. My name is Jonathan Cottrell. You’re listening to
[00:00:17] Developer Tea. In the last episode, I got a question from an anonymous listener who’s
[00:00:23] interested in getting into a leadership role. They’re looking to change their career up.
[00:00:29] Part of the reason why they decided to send in the question anonymously. And they asked whether
[00:00:36] or not it’s possible to lead a team, which they know that leadership is highly relationship
[00:00:44] oriented. They asked if leading a team remotely is even feasible, if it’s possible to lead a team
[00:00:51] as a remote worker. And the answer is yes, but there’s always caveats to these situations
[00:00:58] because they’re not going to be able to do that. And they’re not going to be able to do that
[00:00:59] because relationship is so important to leadership. And there’s always going to be
[00:01:03] things to consider. And that’s what we’re going to talk about on today’s episode. Specifically,
[00:01:08] I’m going to give you tips on things that you need to do to be a great remote leader.
[00:01:12] In the last episode, we talked about different aspects of leadership. And we also talked about
[00:01:17] different scenarios where remote leadership is going to be more appropriate than other scenarios.
[00:01:23] In today’s episode, I’m going to give you really just some practical tips about being a good
[00:01:29] remote leader. Real quick, let’s recap what we talked about in the last episode.
[00:01:33] We talked about the different types of leadership, for example, technical executive leadership.
[00:01:39] This is reviewing and writing code and developing standards. Principled leadership,
[00:01:44] by example, setting forth ideas and talking about your values from a kind of a distant perspective,
[00:01:51] rather than doing that in a one-on-one meeting. You set these up as values that your company or
[00:01:58] that your team has. And then you set these up as values that your company or that your team has.
[00:01:59] The department wants to follow. And then people attach themselves to those values without you
[00:02:05] having a personal relationship with them. Once again, that happens mostly at scale. And it’s
[00:02:09] not likely that you’re going to find yourself in that scenario. And really,
[00:02:13] you shouldn’t be pushing for that scenario until it’s absolutely necessary.
[00:02:17] The last type of leadership that we discussed, and perhaps the most common and most important
[00:02:23] type of leadership for the people listening to this episode is one-on-one mentoring. And we
[00:02:28] discussed the fact that it’s almost impossible to talk about one-on-one mentoring in a single
[00:02:33] episode of Developer Tea, both because this podcast is intentionally short, but also because
[00:02:39] really a five-hour podcast on the topic wouldn’t even be enough to talk about it. There’s a lot
[00:02:45] that goes into effective mentoring. We have talked about mentoring in past episodes of Developer Tea.
[00:02:51] If you just go to spec.fm and search the word mentor, you’ll see a couple of episodes there
[00:02:56] where we have talked about mentoring. And we’ve talked about mentoring in the past episodes of
[00:02:58] So we talked about all these different aspects of leadership. Again, you’re going to have different
[00:03:03] balances of all of the aspects of leadership beyond this list. And you’re going to have to
[00:03:09] learn how to balance those different aspects. And some of those things are going to be more
[00:03:14] affected by whether or not you are remote than others. After that, we discussed when remote
[00:03:21] leadership works well. For example, if distribution is already a part of the DNA of your team,
[00:03:28] a contractor-heavy team where people are coming in and coming out, coming into projects as
[00:03:34] contractors and then leaving a few months later, and then also in teams that have well-defined
[00:03:40] rhythms. And really, that’s the type of team that most of you are probably wanting to build,
[00:03:45] the type of team that has a well-defined rhythm. So let’s talk about what it takes.
[00:03:52] What do you need to do to be a great remote leader?
[00:03:58] One thing that you need to do, and we’re going to stick on this one for a few minutes,
[00:04:01] be explicit about the value of remote work. If you are going to be a remote leader,
[00:04:08] you have to understand and talk about the value of being remote. It can’t go unnoticed.
[00:04:17] Remote work is absolutely different. And it’s important to recognize the differences explicitly
[00:04:24] with your team. At the same time, it’s important to recognize the
[00:04:28] added value provided by remote work. For example, flexibility and diversity of team interests,
[00:04:35] diversity of team locations, time-shifted work schedules. It kind of gives you a 24-hour
[00:04:41] sense of momentum, results-oriented efforts, and the list goes on and on and on.
[00:04:46] Don’t treat remote work as if it’s the same type of work done in a co-working space.
[00:04:52] And perhaps most importantly, don’t treat remote work as if it is
[00:04:57] handicapped.
[00:04:58] This is really the point here. If you talk about remote work as if the remote portion of that
[00:05:05] is only detracting from the work, if you blame the remote nature of your work or the remote
[00:05:13] nature of your leadership for the problems you are experiencing, then people will always resent
[00:05:19] the remote work until you are working in a co-located space. Instead, focus on the benefits
[00:05:28] of the remote work. This is super important, just from a psychological level, for people to
[00:05:33] understand the value and the equality, or at least the parallel quality, of remote work to co-located
[00:05:42] work. The second thing you have to do, and this is just matching right up with our previous episode,
[00:05:48] you must establish a rhythm. This is your job as a leader. You can’t expect a rhythm to suddenly
[00:05:56] establish itself.
[00:05:58] You can’t expect a rhythm to come out of nowhere. You will establish habits accidentally, but you
[00:06:05] will not establish a rhythm accidentally. What does that mean? Well, a habit is something that
[00:06:11] kind of depends on your situation. A rhythm does not depend on your situation, right? That’s kind
[00:06:17] of the primary difference. Habits are done unconsciously, or perhaps even accidentally,
[00:06:24] whereas rhythms, intentional rhythms,
[00:06:27] are executed on purpose, consciously. We already said this in the previous episode,
[00:06:33] but good remote leaders establish a predictable rhythm, especially with access. If you are a good
[00:06:40] remote leader, you are going to be available on a regular basis, perhaps eight hours a day,
[00:06:48] starting at an exact time in the morning and ending at an exact time in the afternoon.
[00:06:53] This access, this predictability,
[00:06:57] rhythm is the most important part of remote work. Being predictable and being reliable,
[00:07:05] being on time for conference calls, being on time for screen shares and pair programming from a
[00:07:13] remote perspective, that punctuality and predictability and reliability is incredibly
[00:07:19] important to your team. Not only do you need to be available, but you need to also be reaching out
[00:07:27] and being able to engage with your team. You need to be able to engage with your team. You need to be able to engage with your team.
[00:07:31] This is hugely important. All of this stuff is important for non-remote leaders. Let me just
[00:07:39] say this for a second. If you’re listening to this episode and you’re just kind of logging this stuff
[00:07:44] away in case one day you become a remote leader, but right now you’re not a remote leader,
[00:07:51] that’s not a license for unpredictability, right? That’s not a license for
[00:07:57] being late to meetings, or for not developing one-on-one relationships with the people that
[00:08:03] you lead. Absolutely the opposite. All of these things are important in co-located spaces. They
[00:08:11] just happen a little bit more easily, habitually, in co-located spaces. You still need to be
[00:08:18] consciously aware of these things, but when you are remote, it’s extremely important to be even
[00:08:24] more consciously aware because you don’t have, for example, water cooler conversations. Those
[00:08:29] personal touch points only happen when you make them happen as the leader. So that’s why we are
[00:08:35] touching on this so heavily. Establishing rhythm is so important. And the last thing that you need
[00:08:42] to do, the last thing we’re going to discuss that you need to do as a great remote leader is you
[00:08:47] need to, if possible, get real face time.
[00:08:54] Get people in the same room face time. And no, we’re not talking about calling each other on
[00:08:59] face time on your iPhones. If possible, get your team, all of your team, not just you and one other
[00:09:06] person, but get all of your remote workers in the same place from time to time, once or twice a year
[00:09:13] maybe, or more often if it’s possible. But get those people in the same room from time to time.
[00:09:19] When you meet, split your time between working together
[00:09:23] in the same room and working together in the same room.
[00:09:24] In the same space and simply being together.
[00:09:27] Some people may push back on this idea of working in the only time that you get to hang out with
[00:09:33] each other, right? You may think that you need to spend all of that time developing personal
[00:09:39] relationships with each other. But here’s the interesting thing that happens. When you work
[00:09:45] together in the same space, this pulls back a curtain of mystery and it builds trust.
[00:09:52] Let me explain what I’m talking about. When you work in the same space together,
[00:09:57] let’s say you’re not on a remote team. You know how other people work. You know what their habits
[00:10:03] are. You see when they pick up and go home for the day. You know what kind of music they listen to,
[00:10:08] what kind of places they go to lunch to. All of this stuff is added information, right?
[00:10:15] And when you have someone who works remotely from you, it’s hard to picture how they work.
[00:10:23] And oftentimes where there is mystery, we have a bad tendency as humans to fill in the blank with
[00:10:29] negative things. Even if your team has strong levels of trust between the workers, creating
[00:10:36] this environment where you’re working in the same space even once or twice a year, we’re going to
[00:10:43] tend, this is a psychological reality, we tend to remember people in the same state that we left
[00:10:50] them. In other words, if you work together in the same space, you’re not on a remote team.
[00:10:52] In other words, if you work together in a space, the next time you’re working remotely from each
[00:10:56] other, you’re going to picture that person the way they were working when you were in the same
[00:11:02] space together. And now the negative mystery that could have existed because of the remote nature of
[00:11:09] your workers, that negative energy is largely relieved. It’s kind of a weird psychological
[00:11:14] thing, but I want you to try it. I want you to see how this works. I’ve seen this work
[00:11:19] in remote workers that I’ve worked with personally in the past,
[00:11:22] and I think you will see this as well. Misconceptions and suspicions about other
[00:11:27] people’s work habits, they tend to clear up in these scenarios. Workers will tend to refer to
[00:11:32] the memory of working in the same room when their mind pictures their teammate working next week
[00:11:38] whenever they all go back home. On the flip side, of course, the second half of this FaceTime is
[00:11:44] equally important. So you need to spend time getting to know each other on a personal level.
[00:11:50] There’s nothing that can replace it.
[00:11:52] Even for remote workers, there’s nothing that can replace it. So if you’re going to lead a team
[00:11:58] that is 100% distributed, I would challenge you to find a way to bring all of those people
[00:12:04] to the headquarters of the company, or perhaps take a retreat together as a team once per year,
[00:12:11] or once even every other year if you plan to stay at that company for a long time.
[00:12:17] These kind of connecting points are going to create anchor memories for you. They’re
[00:12:22] going to create really what stands out as a person’s identity or their personality and how
[00:12:29] they have a space in your brain. That’s going to be largely impacted by the memories you create
[00:12:35] in those moments where you have FaceTime together. Thank you so much for listening to today’s episode
[00:12:41] of Developer Tea. I know this is kind of a heady subject in some ways, and it’s really difficult
[00:12:46] to really nail down all of the important aspects of remote work. We certainly didn’t cover everything
[00:12:52] that was involved in this episode, but I hope you enjoyed it. If you did, please subscribe to our
[00:12:52] channel. We could have covered, but if you walk away with nothing else, remember that consistency
[00:12:57] and availability, eliminating as much volatility as you can, right? Eliminating as much
[00:13:05] unpredictability as you can. That’s going to be absolutely key for you as a remote leader.
[00:13:11] Thank you so much for listening to today’s episode. Again, we didn’t have a sponsor for
[00:13:16] today’s episode, but I’ll take this opportunity to encourage you to go and sign up for a brand
[00:13:21] new newsletter.
[00:13:22] That I’m curating on a weekly basis. It’s called Soft Skills Weekly. You can find it at
[00:13:27] softskillsweekly.com. It’s going to be about seven resources per week, give or take, depending on how
[00:13:34] I’m feeling that week. But it’s all based on soft skills stuff, conversations, articles, interviews,
[00:13:40] podcasts, books, whatever I feel like putting in that week. So go sign up, use a good email,
[00:13:46] because this is going to come straight to your inbox. Thank you so much again for listening,
[00:13:50] and until next time, enjoy your tea.
[00:13:52] Thanks for listening to Soft Skills Weekly, and I’ll see you next time on Soft Skills Weekly.