Skip to main content
Automatically keep your work and documentation completely in sync.LearnaboutDocs.

Tips for remote project planning throughout 2021

Richard Huffaker

Not sure if you've noticed, but working and planning in 2020 has been very different than years past. Video calls have replaced in-person brainstorming sessions. Slack has replaced in-person conversation. And has anyone bought even a single pack of sticky notes or dry erase markers since last February?

That's why we've gathered product and engineering leaders from Sentry, Gatsby, Shortcut, and Vimeo to share their expert advice and experience about how to best tackle remote planning for 2021 and even beyond the pandemic when many of us will likely find ourselves in a hybrid WFH / office world.

During this panel, we discussed:

- How remote work has upended the planning process.
- Advice and tips on using this forced remoteness to make improvements to communication, collaboration and visibility.
- What's worked. And what hasn't.

You can watch the full webinar below and/or read the transcript (which has been edited for length and tone) below that:

Our recorded panel, in full

Was your company remote before this year, and do you plan to stay remote once things return normal?

Dave (Sentry):

I'm the head of product at Sentry. We do application monitoring that helps 60,000 Dev teams find and fix their problems.

And although we were not remote before, we did have a couple of regional offices in Toronto and Vienna that our San Francisco HQ worked closely with. We have a little bit more practice now and I think at this point, we're really playing it by ear. It's a hard time to make predictions about what the future holds for us in terms of remote work.

Nicole (Gatsby)

I'm a senior engineering manager at Gatsby, we've actually been fully remote and distributed since before the pandemic and plan to stay that way. You actually have employees all the way from the west coast of North America to Bangalore, India. So we spend plenty of time working with people from all across the globe.

Nik (Us!)

I lead the Product Team at Shortcut working with Kurt. We've been a remote company since before the pandemic. We had a New York office, but we were always pretty distributed otherwise. And yeah, we plan on staying with that.

Tara (Vimeo)

I'm Senior Director of Engineering at Vimeo, overseeing our core product engineering organization. Vimeo is mostly located in New York, but we do have some smaller offices around the world, as well as some remote team members. I definitely miss the office and the rituals around going to the office and being separated from home. I'm hoping and expecting to do a little bit of both going in the future.

I think there's a lot of empathy that needs to kind of be built into our collaboration processes to make sure that we're taking everyone's environment and stresses into consideration as we're managing these teams.Nik Pai, VP of Product at Shortcut

Have you had any surprises, pleasant or unpleasant, while your company transitioned to working remotely during a pandemic? 


I want to echo Tara. I didn't realize how much I'd miss the literal office. One of the reasons I chose to work at Sentry is that I really wanted to work with those people and I genuinely miss the camaraderie of the office.


It's been interesting. We were already remote and I think the surprise for me is I expected that there would be no change because of that. But the truth is there were lots of changes.

For our employees, their work situation wasn't changing but their home environment was. And that presented some unique challenges. We've learned to adjust by being really communicative about what each person's situation is, and what kinds of things they might end up needing to handle throughout their day. We try to keep things asynchronous when possible, which is really hard, trying to make sure that things that don't need to be meetings don't end up being meetings.


I think there's a concept of remote first and then remote friendly. And a lot of companies that have been remote are mainly remote friendly. So you can be the person kind of left out sitting on a video while everyone else is in the conference room ideating. And now that it's all on a common playing field, you're seeing a lot more participation from people who may have felt left out prior just because they were the one person remote in a given situation.


At the office collaboration sometimes happens really local to the people who you're sitting around and your immediate teams. And I feel like shifting fully remote, we've kind of broken down those barriers of location. We actually just pulled off a release that involved, I think it was six teams around the world, and everyone meeting on video was the thing that leveled the playing field for collaboration.


Yeah, occasionally we'd have teams or one person remote or working from home for whatever reason and they tended to be much quieter in meetings.

One of our people who's in Kansas right now, he's a complete star when you put a microphone and a video camera in front of him. But that doesn't come naturally to everyone and now when we're all collaborating in the exact same way, as a little box onscreen, there is broader collaboration.


I think there's a lot of empathy that needs to kind of be built into our collaboration processes to make sure that we're taking everyone's environment and stresses into consideration as we're managing these teams.

Look at your calendar as a tool and really aggressively block off the time you need... If you don't protect your calendar, people will fill it up. Tara Feener, Sr. Director of Engineering at Vimeo

What's worked really well to help with this situation where there's an even playing field directly onscreen, but a less even one in the homes behind those screens?


Hopefully we're all sharing a great example of it in that we've been trained over the last several months we've been doing this that there's a pause, right?

[Several second pause]

Like that.

We've picked up the verbal tics that indicate "I'm done speaking" because we can't see pick up on physical cues any more.


For me, looking at my calendar as a tool and really aggressively blocking off the time I need. So like I have a toddler here and a small dog, and they both have their own schedules. I wasn't so great at the beginning to be sure to block off time that corresponded to their needs or to my partner's needs.

And then also carving out blocks for focus. And for deep thinking, I'm the kind of person who solves problems as I'm commuting into the office on the subway or during that 15 minute walk through Chelsea. Having lost that time, I've been trying to recreate those habits and create that space for marinating on ideas.

If you don't protect your calendar, people will fill it up.


As somebody who's been working from home for a long time. I've tried to develop a lot of strategies around starting and ending my day because what I found is that I actually work more from home that I ever did in an office. I tend to overwork.

I haven't been consistent about it, but I try to replicate a morning commute. So if the weather is decent, take a walk around the block, grab a coffee or something that kinda signals the start to the day. At the end of the day pre-pandemic I used to I have a class at my gym that I would go to and it was a hard stop to the end of the day. Having an online class or a non-work meetup / event of some kind can create the same feeling.

Let's talk planning. Do you feel like you've lost anything from your old process? Is anything working better? 


We were actually in the middle of a design sprint when the call came for everybody to stay at home. We were physically in a room where we were putting sticky notes and working through ideas and we had to suddenly pivot to run that whole process online to keep things going. Kudos to the engineering manager on my team who did that because she was able to pull it off in a way I don't think I could have.

Transitioning to tools that allow us to recreate some of that collaborative process has been huge. I think the barrier to picking up new tools and tools that solve the problems we have kind have in the moment has lowered significantly. I feel like years ago adopting a new tool this heavy thing that you had to really think about before getting buy in for it. But I feel like today we're literally just being creative thinking how we rely on integrations to actually tie all these tools together and bring them into our workflows and into Slack or wherever the conversation is happening.


Even though most of our planning gas always been remote for longer term plans like our roadmap, we tend to get together in person. We actually had a product summit right before the pandemic started to take hold. I was actually in Chicago, ready to get on a flight when things all started to change. Part of our leadership team couldn't even make it at that time because they were located in areas like Washington where things were already kind of serious.

Nobody really knew what was going on and we learned a lot of lessons about how to start leveraging tools like Miro was a huge one for us. The most important thing is just getting creative and trying to find ways that people can be engaged when they're not in the same physical space.


Yeah, it's I think the engagement that's a key part of it.

Stand ups are basically the same, they go on a little bit longer because everyone's sitting and you lose that forced discomfort. But then when you start getting to sort of the big strategic things where there should be healthy tension and there's a component of really I, you know, I don't so much have a business case as much as I want you to believe in my narrative that Serverless is the future or what have you. How do you recapture the magic of two smart people disagreeing with respect in front of a whiteboard. Where both people are probably 90 percent right about a big thing.


I think the strategic planning side and just getting into a room to hash things out is what has been lost. And, you know, the concept of an offsite really exists in… in some ways because it takes an hour to just to break your mind away from tactical execution. The challenge with the video is typically the energy just goes straight down as the meeting goes on. And there's no way to ramp back up the way that you might in an offsite like maybe it's a cookie break, maybe everyone just goes out for a quick coffee or something that gets the energy levels back up.

I think the other big element is that we've lost the ability to go talk directly to customers. I mean, I think it's the same thing for them to get on video to talk to you, thats very different than being able to like have lunch, have coffee, sit in… sit in, you know, their office, see how they're using your product.


Yes. As much as I begrudge my carbon footprint from visiting customers, it really is completely different. It's easier in person yo get people to not just say nice things. You just said this works for you and you pause because you wanted to say, "but it's just okay." Like the coaxing out… what people don't want to say, right? Our customers are not trained in how to give us actionable feedback, right? It's almost every customer discovery session is also a training session in terms of no no… no, no, I'm… I'm… I'm very receptive, right? Tell me what's broken and then I want to, you know, or even I want to see work right? And there's just absolutely no way to see sort of the behind the scenes about how the process comes together. So we definitely lose something there.

The more you see arguments being made with data, the more the arguments that don't have data – that are sort of just hand waving – start to be seen as inferior... but never bring data in isolation, right? Use the data as the underpinning of the emotional story you're going to tell.Dave Hayes, Head of Product at Sentry

What are some things from the past year that you're happy to take with you as we go into 2021? 


Something we've been doing a lot of in the past half-year at Vimeo is shifting to a culture of show over tell and using prototypes and diving further into the work-in-progress to get just deeper insights, really put it in front of people and get reactions. And then we're also using asynchronous communication to collect it. So it doesn't have to be a right now, real time call. But what does the screen recording of the demo look like when collecting feedback that way?


I think just doing is more of something is part of the answer. Even if you can't travel, you can do two times as many, right? So I have to be able to put together the same story from two times as many less-good interactions. And the good news (or bad) is everybody's in the same boat. We're never going to be in a place where the number of people working from home isn't significant. You can't ignore the other. non-office ways of working.


Yeah, I think industry will move in that direction. Back to your point that, you know, customers don't always know how to best give actionable feedback. I think as things change this new way of doing things will just become common practice and customers will get a little bit more used to using these new avenues versus the ones that may maybe been driven by more in person contact.


I'm also just excited to see what tools emerged from this time. Like we're already starting to see that shift and we're all talking about the tools that we've been creatively using to solve problems. So, I'm personally really motivated by what we're going to create right now, which is gonna fuel that movement even more.

How are you sharing progress with your teams?


One of the things that I think we're struggling with is that we the intersection of three things going on, right? We not only have work from home but we also have the stress of pandemic by itself, and the extra work that comes out of that with many employees needing to take care of their family or not having much extra space at home to work from.

We're realizing now just how much of our communication path might rely on one or two relationships, right? And if we make it a point where we've… we've doubled the company remotely and have twice as many PMs trying to talk to twice as many sales engineers and that grows, how do you manage the communications that come out of that growth. Things that used to work with one highly informed person talking to one other highly informed person who understood all the background now needs to spread out among people who've not been in it as long. Which is why it's over communicate. But that'd be true whether we were working at home or not.


You know, at another growing company, I think it's already been a challenge for us to share what's going on within the entire company. And also doing it remotely which we always have been... what are the ways to get people the right amount of visibility? I think it again, it comes down to tooling, but in a way that… we've tried actually to reduce the number of tools we're using because when you get too many, it actually kind of compounds the problem. So we've done things like put out higher level roadmaps and a beautiful Notion document laying everything out. And then we'll link down to things like Epics in Shortcut which will link out to an architecture document. So there's a thread you can follow depending on what level of granularity that you're looking for.

To Tare's point, I think it'll be cool when…we start to see tools built specifically to tackle all these challenges. One thing we've put together is a tool that scrapes from Shortcut the things that have shipped based on a particular label and sends that out company wide email. So people can see a high level view of what's going on and what we're shipping to customers. And if they wanna dig into those deeper levels they can follow links and breadcrumbs.


Another thing we've been doing is we're using video, really trying to use Vimeo as a means of sharing the work that we're doing to increase visibility. Every Friday we do core product demos where anybody can show anything. It could be a designer showing a design, a PM showing an insight, or engineering showing whatever they have. We record the whole thing and we add chapters. We can then link that out to anybody at the company. And that also goes into a slack channel. So people are able to follow along, see that there's new demos and watch them and reach out to the folks who sparked the idea.


We obviously use Shortcut and we have it set up in a way that gives the full transparency of what's being worked on. To Dave's side, the challenge that we have is just making sure everyone understands the context of why we're doing these things, why they got prioritized, and how they align with the larger corporate objectives. As much as we can, we try to take that context and use our virtual town halls, our demo days, and posting on slack to show it to people as many times as we can.

The big challenge that we have is this creates meeting fatigue where everyone tries to replicate some of what we've been missing by just deciding that we're going to have a meeting for it. And so now people are always conscious about adding one more meeting. We want to be able to meet with everyone to share the road map and give them the context, but we try to balance that with trying not to overwhelm the teams.


This raises a really good point, right? You can hear from all of us. We want to share, right? And I think that is something that we have to work a little bit harder in a work from home environment to say like, you know, we're not… we're not scary. I don't care if this is your first job out of high school and you've only been here for two days: you can ask me questions. I don't wanna throw a lot of meetings on your calendar, but if you see something in a demo day and you're curious about it, why not ping me? I may not be able to answer the question but your question is valid and I will route you to the person who will answer it and they will be just as eager to answer your question because if you have a question, probably 10 other people also have it.


I think that's one of the reasons that the push not pull culture is so important because as you start to put things out there, people get curious, they want to ask questions they want to get engaged. Whereas, you know, if you're just waiting for things to be surface to the rest of the company, that sort of engagement is less likely to happen.

Are the people on your teams looking at more data and tying that to how their own work is moving metrics?  


I mean, we all know what the right answer is here: obviously, yes, no one's going to stand up and say, no. We're growing, right? We're building up not only a larger customer base, but adding more people who are able to process that data. Narratives there are probably the most compelling and changing people's minds, but you obviously still have to use data. So I mean again just type back from, you know, we're growing very quickly. Obviously. So the answer has been yes, if there is an inflection point it's that this is growing slightly faster than it would be without work from home. At least I suspect that to be true.


Yeah, I feel the same way. We started using Amplitude just before everything shut down. So that helped unlock a self-serve insights and discovery kind of culture that I think the team has really ran with.

Demos that used to just be prototypes of things. And now, you know, product managers are coming with a chart or a dashboard or an insight from Amplitude. So we've seen that shift for sure. But it's hard for me to untangle it from the introduction of a self serve tool that everybody can use to explore insights on their own versus just having it presented to them.


I would echo that. I don't think anything has changed from a data strategy side, but I would say qualitative data has been more challenging. And so there's been a more uptick in our attempts and ability to try to get that signal.


There needs to be effort put into training people that this is what a convincing argument looks like, right? So people on my team know that there's a good way to win me over. There's a business case, but also really it's about making an emotional statement of fact.

The more you see arguments being made with data, the more the arguments that don't have data – that are just hand waving – start to be seen as inferior. So if the point of this question is, how do I bring more data? It's to never bring data in isolation, right? Use the data to as the underpinning of the emotional story you're going to tell.

That feels like a strong point to end on. If you'd like to learn more about our speaker's companies, visit, Gatsby.js, and And if you'd like to keep with our future webinars and events, be sure to join the ongoing conversations in our Community.

More stories from Shortcut