The Remote Show

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Company Website


Tyler Sellhorn (00:02):
Hello everyone. My name is Tyler Sellhorn and welcome to another episode of The Remote Show, where we discuss everything to do with the remote work with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire.
Today, we are blessed to be learning out loud with Jen Dennard. Jen is a co-founder at Range. Jen is passionate about team and workplace dynamics, and improving the day-to-day experience at work. Prior to Range, Jen worked in organizational development at Medium and other technology companies. Jen resides in Colorado and is overly enthusiastic about Sour Patch Kids, hiking, and bad fantasy books. Jen, tell us. What problems are you trying to solve at Range?

Jennifer Dennard (00:47):
Range is focused on improving the day-to-day experience at work. We do that through a focus on teams and how they communicate. Thinking about how you build a better asynchronous foundation of communication, so you can reduce your meeting load, how you can actually improve the facilitation and engagement in your live meetings, and how you really connect and build team cohesion through small moments of team building and culture. Through that, we really empower and strengthen teams.

Tyler Sellhorn (01:14):
Super cool. I love that you are drawing out those three buckets of, "Time," or, "Not time," or, "Not at the same time." You mentioned communicating, and then right away you talked about asynchronous communication. Then, you talked about live meetings. And then, you also talked about team bonding. Maybe the thing that I'm curious to learn more about as you all think about that at Range is to say, "What is the right balance between those things?"

Jennifer Dennard (01:45):
It's a really interesting question. Unfortunately, a lot of teams are like, "Give me the recipe." Two hours a day, live meetings.

Tyler Sellhorn (01:54):
Guilty. Here I am asking the same question.

Jennifer Dennard (01:57):
Not at all. It's what we all crave. I think each team to some extent finds their own balance. But a lot of what we think about at Range is approaching it from two lenses. One is, "What is the purpose of the communication that you're trying to have?" For instance, if you are trying to have a brainstorm. Often, you can break that brainstorm down into different pieces like sharing context.
Sharing context is something that can be done really well async. We might say, "Cool. Send out an email or a doc in advance of your brainstorm." To have everybody get up to speed on what you're going to be talking about. And then, you might have the part where you're sharing individual ideas, and finally the part where you're building off each other's ideas. Really, that last part is what's really helpful to be done live, but a lot of the individual parts can be done async.
And so, when you break down this idea of a brainstorm or a specific meeting down to the specific purposes of what you're trying to do, you can start to really see what's a good part to be served by async communication and what should be done live. The other lens, I would say, is providing optionality. Some aspects with, for example, team building is that you can do a lot of team connection asynchronously through answering questions, sharing how you're feeling.
You can also do a lot live through social game times, or audio-only meetings. Different teammates prefer different options. And so, actually having all of those in small doses can be really powerful for a team. And so, we think of it as, "There's a healthy mix." You need to build the muscle of knowing when async or live communication is the right approach.

Tyler Sellhorn (03:42):
Well, I definitely appreciate the invitation or the option to become more purposeful in our communication. You mentioned that there are certain behaviors that are best served with an asynchronous moment. You mentioned sharing context and using an email or a document, and then saving that live serendipity of building on each other's ideas for a synchronous moment.
How do we learn that? You mentioned the optionality or which options go when. Or building the muscle to know which things are which. How do we do that well inside of a team? To say, "I know that this communication is best in the meeting pre-work. And I'm going to save this part for the actual meeting." How do we teach one another how to do that well?

Jennifer Dennard (04:30):
It's a great question. Because I think it's something we've all been faced with the last couple years, and sometimes have learned how to do it okay, but not necessarily well. And so, the way I think about it is starting off with a simple foundation of some of the things that are maybe more obvious to move asynchronous. Where Range really started was in providing the ability to do written status updates or, "Check-ins," as we call them.
That really provides a day-to-day moment for the team to share in a written asynchronous format, what they're up to, and how they're feeling. Putting in place something simple like that really starts to build the habit of sharing information asynchronously. What you'll start to see over the first few months or few weeks even is ... In a few instances, someone shares a status update and you are going back and forth in comments for 20 minutes of, "Hey. Is this what you mean? Or is this?"
That is a great signal of, "We need to hop on a call. We need to have a live moment to discuss this." But you can't actually figure that out for your team until you start to put in an asynchronous foundation. And so, that's where we really recommend starting with something simple, like your team status updates or stand-ups, and moving those to an asynchronous format. And then, you start to build that muscle over time.
Because honestly, you'll just find yourself wasting time writing. You're like, "I think this would be way faster on a call." Great, so have a call. Have a meeting. And then, the key point there is to make sure you're documenting notes or key decisions, so that other folks who may be on different time zones or couldn't attend that ad hoc meeting can still get the information or understand what was discussed and decided.

Tyler Sellhorn (06:17):
Okay. I love the idea that we're going to use the trigger, so to speak, of a back-and-forth deep in the thread. That probably needs to go up a level at least. Right?

Jennifer Dennard (06:29):
Or if you find yourself frustrated. Frankly, a moment that I often use ... If you feel like you're in a moment where you're like, "This person just is XXX. They don't understand my work." You know what? We are writing. We don't actually know how they're feeling and what they're thinking. Maybe we should take a step back and actually have a call. Because it's way harder to have that type of misunderstanding when you're actually having the real time back-and-forth.

Tyler Sellhorn (06:54):
Plus one to that feeling of, "I am not understood." I'm going to center the other person's response. I'm going to say, "You know what? I'm going to believe the best about them." It's not that they don't understand me. It's not XXX, as you describe. They really do want to work with me. I'm going to believe that about them, whether or not they deserve it. Let's just be generous to people even when they don't deserve it.
Maybe the thing that I'm wondering is, what are some of those other triggers for us to go up a level with people? Obviously, there's that feeling that you described. And then, there's the literal going back and forth deep in the thread. What are those other things that we can be on the lookout for? To be like, "Maybe we should schedule a call?" Or, "Hey. I need to send them a voice note." Or, "There's not enough context here. I need to flesh this out in a bigger document." What are those moments for us to pay attention to? To feel for ourselves?

Jennifer Dennard (07:51):
One that we often highlight is uncertainty. When there's a high degree of uncertainty in terms of what you're doing or what you're going to be doing, that can be a good signal that a live discussion is helpful. Because oftentimes, you sit down to write the project spec or to start drafting the email ... What ends up happening is it becomes an epically long email. Or it's taking you a really long time to figure out what to say.
That suggests that even just a 15-minute call with someone else or scheduling time with the whole group, depending on the group that you're working with or the team, can be really helpful. Because the degree of uncertainty of where you need to go next and what you need to do is too high. Sometimes you know that in advance. And so, it's really easy to be like, "Cool. We need a call to kick this off, because even what we need to do to start is unclear."
And so, that's something that we often use as a trigger when we work with teams within Range, to help set up meeting agendas, and to facilitate those types of discussions where people can raise those ad hoc topics. The other thing, I would say, that personally I use is nuance. Sometimes the time to value of writing something down versus explaining it to someone through recorded audio or through a Loom or through a live meeting ... It's so much faster.
Because you're drawing connections between maybe three or four or five different points. When you say it out loud and can make that discussion, it's really easy for someone to grasp. But when you write it down, it changes the meaning of what you're saying. And so, that's where I think it can be really helpful to do that live. When there's a high degree of nuance. And then, once you've come out with a decision or something that's more clear, that's when you can then go back to async or back to writing. You want to make sure to do so, so that others are staying in the loop.

Tyler Sellhorn (09:52):
That's awesome. To start building the thresholds for our teams. To be thinking about, "When is there too much uncertainty?" When are things unclear? When is there a large amount of nuance that needs to be navigated before we can communicate a decision?

Jennifer Dennard (10:08):
One of the things I was going to say that also comes up is, "To what extent do you have shared context with the person or the team that you're communicating with?" One of the benefits of using a tool like Range to have your meeting notes sent to Slack, or to have your asynchronous check-ins and that foundation is ... There's a high degree of shared context about what's happening on the team and how folks are doing. Now, when you work with another leader or a different team, sometimes that shared context of what you're trying to do, what's been happening recently, just isn't there.
And so, that process of catching someone up can be really hard if you don't already have a good asynchronous foundation. And so, that's where I think that's a good question to ask oneself, which is a little bit different than, "Is it uncertain?" More like, "Does this person have any idea where I'm coming from?" Ideally, over time, as you're establishing more async and written context sharing, that starts to become more and more frequently, "Yes."
But early on, it can be a good thing to be like, "Cool. This person has no idea that the project went off its wheels last week." And so, when I send them an email that's saying, "This deadline is pushed," they're going to have a strong reaction. Whereas, if I can have a quick Loom recording and explain what's going on with the team, they might actually have an ability to have a conversation about that. Or schedule time with them. That shared context is another cue that I use.

Tyler Sellhorn (11:37):
Thank you for that cue as well. I think one of the things that I'm hearing you say is rhyming with ... The Mount Rushmore of remote work, for me, it includes Lisette Sutherland. One of her phrases is the idea of, "Working out loud." That's how we can get to that shared context. To say, "It's not a secret what I'm working on or why I'm doing things."
It's because I'm telling everyone. I'm telling you. I'm telling everybody in public channels, rather than just in the DMS. I'm recording my screen. I'm recording my voice. I'm using the transcripts of those messages. I'm formatting my messages clearly and centering your response to them. These are things that are really important. You even mentioned the idea that we're going to have meaning agendas and topics before we're going to get into a call. I think that's really important invitation too.
Just to segue back to something you said at the beginning. Talking about optionality. It's really important to be thinking about the idea that we're going to maintain a certain level of an invitational way of operating together. Providing options and allowing for idiosyncrasies to exist. Maybe I'm inviting you to talk some more about what you mean when you say, "Optionality."

Jennifer Dennard (12:55):
One of the things that Range really encourages with teams is thinking about the weekly, monthly cadence or rhythm of your team. If you think about, let's say, a traditional scrum team. The sprint meetings that they have. Backlog grooming, planning, retro. Those really make up the rhythm and cadence of their work. For other teams, it might be a weekly team meeting on Mondays. An all-hands, once a month.
We actually profiled a lot of teams and their cadences in Range's How Teams Work series. When you have this foundation of, "This is how we work from an asynchronous communication perspective. We share goal updates every two weeks. And these are the meetings that you can come to get help." That really starts to lay-in this foundation of where people know where to bring certain topics. Having the ability to communicate in these different ways.
Then, when you start thinking about optionality, what you have is someone can bring a topic ... Let's say, they could raise it in Slack. They could send out an email. They could raise it in a team meeting. It's really about making sure that the team knows those options and when to use what. That way, they have basically the tool set to solve their own problems. A lot of the way that remote work is pushing companies, which is really powerful, is to be more empowering of teams.
To be empowered, people need context, as we discussed, but they also need to know where to take their problems. Having the solution be, "Have a one-on-one with your manager," and that's the only option ... That's really confining. It means that the manager is going to be overworked and overwhelmed, and that the individual's going to be slowed down in their work. Because they're not going to be able to get help for two weeks until they have that next one-on-one.
Whereas, if you have options to take it to a team meeting and add it to the agenda in advance, or to share it in your Slack channel, or to send an email, and you know what type of problem should be raised where ... That really starts to empower individuals to move quickly and really speeds up how productive and effective the team can be. Plus, your team is happier, because they're actually able to get help and support from one another. Not just relying on a manager.

Tyler Sellhorn (15:17):
Well, shout out to the scrum teams for showing us the ways to build habits and routines and rhythms to our work. I think what that does, as you described, it's giving us clear containers for certain topics.

Jennifer Dennard (15:33):

Tyler Sellhorn (15:33):
You've done the study, and I'll try to get the link from you to include your series of How Teams Work. But I think the moment that you described, where you're saying, "When to use what." You were touching on it there at the end. Why is it that knowing when to use what really does accelerate our work? Really gives us the speed of ... I like to say, "Complete communication is much more important than fast communication."
Clear communication, as we've been talking, is the main driver of strong bonds between teammates. Giving each other the space to be successful and being invitational. These are all themes that we've been talking about, but you use the phrase of, "When to use what." Tell us more about how we can be clear about that with our teams.

Jennifer Dennard (16:27):
Some of the simple techniques here are writing up a communication guide. That might sound heavyweight, but it can be three bullet points to start. And then, you can expand over time. It could be like, "Slack is for urgent stuff. Email is for things you don't need a response that day and there's a lot of context. Range is for sharing your regular goal and status updates." It can be that simple.
Over time, you add more to that. "Cool. Here's how we use our team Slack channels. Here's how we document notes and where we keep them from meetings. Here's what a project spec template looks like." That is something that you can build out over time, but it really starts with just, "Off the top of your head, if you had a new hire, what would you tell them about how your team communicates?" Put that in a doc and start using that to iterate on.
What that does is it reinforces for the team, "This is how we do things." Also, it gives you the opportunity to be like, "Wow. That's how we do things and that's not great. Let's evaluate and start to improve that." Because sometimes, when you are stuck in the soup of feeling a little overwhelmed as a maybe newer remote leader, your team is feeling a little disconnected. You may not have a great sense of always what's happening.
It can be really hard to figure out, "Where do you start? What do you do first?" Sometimes just writing down, "This is how we work," is really helpful. It's just, "Cool. Let's document what's happening now." Because you can't change it all immediately and that helps illuminate where to start. That starts to create the options that you'll want over time for different places for people to go and communicate.

Tyler Sellhorn (18:17):
Well, thank you again for inviting us to reflect and to observe the soup we might find ourselves in. To find out just how lost in the sauce we might be. I think it's really interesting to hear you say, "Just start with three bullets." Say, "Do this here, do that there, and do the other thing in this other place." And then, iterate. There's probably a spot to say, "How do we scope a project? Here's how we start with a brief."
These are not new ideas. But unless we are intentional about what we're doing, we're never going to be able to look at it together and say, "This is where we are right now. This could be better, but this is how we're going to start." I think the invitation to start and to look and to observe, and then to take action from there is really the best thing.
I think it's really interesting to hear you say that you're passionate about team and workplace dynamics. That's in the service of improving the day-to-day experience at work. How do all these things that we've just talked about .... Connect the dots to that experience of working in a remote team. How does this all serve that mission that you've expressed?

Jennifer Dennard (19:29):
When you think about your daily experience at work, often from an HR perspective or company leadership, they think about ways to support individuals through ... Don't get me wrong. Super valuable things like flexibility of schedule, salary, benefits. Making sure that people have access to mental health resources. I am by no means opposed to those. We do a lot of that at Range and try to increase over time.
But the other aspect of whether you enjoy your day-to-day experience is just, "What is it like to work on your team?" That often gets overlooked when we're thinking about improving an employee or teammate's experience. We don't think about the seven, eight hours a day they spend working with the people on their team. And if that experience is frustrating, exhausting, isolating, then you are consistently frustrated, exhausted, and isolated.
That's what leads to burnout and what leads to retention issues. Just a negative loss of the human potential. And so, when we think about dynamics, that's really what I mean. What are your interactions like with your team and with your work? How do you improve that over time? And so, a lot of the testimonials we hear from Range customers at Twitter and New Relic or Turnitin are things around ... Range helps them connect with their teammates, helps them know what's happening, and just really improves that day-to-day team experience.
And so, that's the types of things I mean. When you start your day, do you feel like you have the ability to say hello to your teammates? Do you feel like you know what you need to do each day? Do you feel like you know what you're being held accountable to for your team? That's what adds up to our daily work experience and whether or not we enjoy that experience which makes up so much of our lives.

Tyler Sellhorn (21:31):
Jen, thank you for going deep on the workplace dynamics of our remote lives these days. I'm so interested to hear more from you about this favorite question of mine just recently. To zoom out a bit and look at the periods of time that we have been living through here recently. To say, remote work before the pandemic. Remote work during the pandemic as, fingers crossed, things continue to wind down here.
And then, talk about a future that is post-pandemic and maybe has some amount of people returning to the office and others choosing a remote-first workplace. How do you see those different periods of time? The ways that they are similar and different. Maybe talk about those different epochs as it were.

Jennifer Dennard (22:17):
I think before the pandemic, a lot of the workplace dynamics issues that we see today existed within companies. But to some extent, there was a learned helplessness and a feeling that, "That is how work is." For instance, oftentimes, you were maybe in the same building with your teammates or other coworkers, but they were six floors away from you. Or they were in entirely separate buildings. And so, the communication experience was actually quite similar to what we experience today with remote work.
Many folks didn't feel empowered in terms of their own work. Or in terms of flexible schedules and having to be in the office. What was true then was that many folks questioned the ability for remote work to be successful. With the pandemic, it's one of those events like many in history where our collective understanding and learning shifted. We had this, "A-ha," moment that some of us maybe predicted, but others truly weren't aware of.
We can be effective when we're communicating virtually. And that with intentionality and how we approach that, it can be actually even more powerful for your individual teams and for companies. I think it was Airbnb who recently announced that they were shifting to entirely remote moving forward. Or the option to be remote. And that they'd had the most productive two years of their company history.
That's the type of things we're seeing. At the same time that's happening, people are moving to be closer to family. They're able to see their children more. By no means am I dismissing how painful the pandemic has been, and the loss of life and ability for many. What I see coming down the pipe, so to speak, is now we have people returning to the office.
And so, the next learning is that it's possible to have both. And it again requires that type of intentionality. What's so powerful now is that the secret is out of the box. Employees know, and they're willing to demand and ask for the flexibility of remote work. That's new. And that's what is really powerful is that people have that knowledge and awareness that other companies are willing to offer that to them.
It's really giving a lot more power to the employee. You see this in lots of ways in the environment right now. With the increase in unions being started, joined, and things of that nature. But that shift is really powerful. I see that continuing over time. And so, it starts to become companies who have a competitive advantage if they're doing remote work well. You see currently people who are looking for jobs starting to see that as a differentiator.
When they ask in interviews, "What's your policy. How does this work?" If they don't have thoughtful answers, and they aren't using best-in-class remote tools like Range or Loom or these different other things, then folks are starting to turn companies down for that. That's what I think is going to continue driving this trajectory where we have flexibility. Where people can go into the office if they want to. Or can be remote and working from wherever.

Tyler Sellhorn (25:26):
Thank you for walking us through that and inviting us to let go of our learned helplessness. To unlearning that learned helplessness, and also learning of our powerfulness. Being invited to say, "Hey. What's it like to work there?" When we say that, we mean, "What is it like to work there as a remote-first? What do you mean when you say a remote policy?"
Not just, "You can work remote." Or, "We're remote-friendly." But what does that look like as a workplace? How do you work together? Maybe that's the thing that I would invite you to conclude here with. What do we say as hiring managers to those people that are asking the question, "Hey. What is it like to work there?" Or, "Are you going to be remote long-term?" How do we answer that in the affirmative in ways that satisfy those remote job seekers that we're hoping to include in our teams?

Jennifer Dennard (26:23):
Ideally, your company and HR team has a policy that's actually set of what remote work is going to look like. In terms of which locations are allowed and things like that. But often, that's outside of the control of the day-to-day manager, the director who's got their team. And so, the way I think about it there is laying out for the potential hire, "Here's how we work. Here's how we ensure that people who are in the office or are at home can connect."
You're really talking about solving their basic work needs in some ways of, "Do you have a sense of connection with your teammate?" Being able to tell them, "Here's what we do day-to-day, week-to-week. We have game times. We have communication practices that ensure we can connect with each other emotionally, not just about work."
They might also want to know things around, "How does the actual work get done? Is it more about live collaboration? Am I going to be in Zoom meetings all day?" And so, thinking about the basic needs that someone needs to know about and addressing that with how you work. You could potentially even document that ideally. Where it's like, "Hey. Here's how we work as a team, so that you have transparency into what you're joining."
Even if someone disagrees with a small aspect of that or wishes it were different, oftentimes the knowledge that the team has thought about it and is open to adjusting that over time or engaging it ... That's what closes the deal, so to speak. Because it shows the thoughtfulness and the intentionality behind it. That really makes the difference for new hires or recruits.

Tyler Sellhorn (28:00):
Thank you so much, Jen, for learning out loud with us today. We really appreciate the time you've taken to show us what it is to be an excellent remote team.

Jennifer Dennard (28:10):
Thanks so much for having me. It's really been a wonderful conversation.

Tyler Sellhorn (28:14):
Thanks so much again for listening to the show and be sure to check out weworkremotely.com for the latest remote jobs. And if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone we should talk to, any advice you have, or if you'd like to advertise on the podcast, please reach out to us at [email protected]. That's [email protected]. Thanks so much for listening and we'll talk to you next time.

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