Collaboration

Lessons from Building a Remote-First Async Team

Punchlist app - building an async remote first startup team - by Pete Bernardo

A behind-the-scenes look at building the Punchlist team to practice what we preach: asynchronous communication and remote-first collaboration.

As a “team of one” for a few years while coding Punchlist, I had plenty of time to dream about my ideal team. Which roles would we need? How would we organize our work? How would our office be laid out?

I always envisioned a small cross-functional team with desks and whiteboards in the same room. This allows collisions of ideas and camaraderie that lead to great products. Or at least, that’s what we all thought before the remote work revolution.

Nic Rosental joined last year as co-founder, and we had previously worked on teams like this together. Collaborating in the same room felt comfortable to us. So as we thought about how we should structure our team at Punchlist, being co-located and 9-to-5 is where our heads initially went.

But then we got to thinking if this made sense for Punchlist – an asynchronous communication tool that is often used by remote creative teams. Is this really what we stand for, or are we just on the treadmill of what we think others expect us to do?

Going async

Asking that question became an inflection point for us. It began to feel pretty hypocritical that we wanted to be in the same room to build a tool designed for people who weren’t. 

If we are developing an app that changes how you collaborate on creative projects, how can we then say the only way to build that is by using old-world practices of being in the same physical space?

We also started thinking about what we value in teammates, and the ideal culture fit for Punchlist. Which is more important: being in the same room, or hiring the very best talent you can find for the role? We ended up choosing the latter, and kicked off a bunch of decisions about how to build the best asynchronous remote-first team.

Before you hire a remote-first team

Before hiring, I think there are a couple of keys to getting the right people interested. Know your organizational values, bake them into your site and make sure you can speak to them. Make sure they are not hollow, and not just what you think others want to hear.

With a solid set of core values, write a straightforward, plain English job description. Our strategy was to nail the core expectation of the roles — both for the person applying, and what they could expect from us.

It’s also worth noting that for Punchlist, we posted four jobs and received 1,848 applicants. And that was only a matter of weeks! It was a bit of a noisy mess combing through nearly 500 applications per role, and we probably would have cut that by 90% had we not posted our roles on Linkedin. The top qualified 10% came from industry-specific job boards (e.g. AngelList), referrals, or social media channels where our community already followed us.

A few tips on preparing to hire:

  • Systems: Figure out your pipeline process for how you’ll review and schedule candidates, before you post the job. Be prepared to move fast.
  • Know your nonstarters: What are the dealbreakers? Are there any timezones from which you won’t consider candidates, even if you’re hiring remote-friendly? Or are you truly asynchronous and hiring from anywhere? What criteria can you quickly rule out when narrowing down the talent pool?
  • Core values: Write up the 3-5 qualities your teammates should embody. Make it specific to your workflow and vision. Avoid generic adjectives and “hustle” culture.

Our remote-first hiring process

In terms of the hiring process, we broke it down into a few steps for the applicants that fit our core expectation.

  1. 15-Minute Phone Screen.

    The goal is to understand if the application they submitted aligns with what they say. We also asked if they had any questions about the business, role, or process. Tip: If the candidate doesn’t have questions for you, they are not interested enough in your business! These folks just want “a” job. Not “this” job.

  2. Asana Test Project.

    This step is the unusual one but proved to be highly effective for an async remote team. If the phone screen went well, we invited them to an Asana project. The board we created had one small task outline in it that involved mostly planning and a little bit of execution.

    We gave each role the exact same task with slight variations based on the core expectation of the position. We asked them to spend a couple of hours over the course of a week, and show their thinking on how they’d approach the challenge.

    This one step accomplished a lot for us.

    • First, if you really wanted to work for Punchlist, this task let you show that. It rules out pretty much anyone who isn’t really excited about your company’s vision. And conversely, it enables both the candidate and company to truly feel what it would be like to work together.

    • Second, for a small remote team that operates asynchronously, being organized and self-sufficient is critical. Given an almost-blank Asana board, can you illustrate how you’d run the project and collaborate with the team?

    • Lastly, are you good at communicating using digital tools? Do you understand how to keep others in the loop and collaborate remotely, without requiring follow-up or “shoulder taps” in the office?

  3. One Main Interview.

    If the test project went well, we would schedule a one-hour call in which they could present their thinking around the task. We’d also talk about the role in more depth, and answer their questions very transparently.

    Toward the end of that hour, Nic or I would join each other’s calls so we could all meet and ask a couple more team-based questions, centered on culture fit.

    Please note, we do NOT do extra rounds of arbitrary interviews – just this one main interview – especially as an early stage startup. Far too many tech companies drag candidates through a month-long process, juggling timezones and Zoom calls, only to miss the boat on great talent who accepted a different offer. Don’t do this.

    A power shift is happening, and top talent is in-demand. Get synced up internally on what you’re looking for; vet for these things with one main interview slot; and see how they think on the job with the test project.

  4. Offer Call.

    If all of that went well and both sides were interested, there was a final call with a walkthrough of our offer (salary, benefits, perks etc.), followed by an email with all the formal details.

    At this point, the candidate has already done their part and the work was on us. Don’t ask them to prepare anything more for this Offer Call. Just make the offer!

This 4-step process worked exceptionally well for us at Punchlist. It allowed us to go four for four on offers accepted, move quickly, onboard all four hires simultaneously, and beat out the competition (be mindful that every candidate likely has multiple irons in the fire).

After two months of everyone working as a team, Nic and I feel very fortunate to have an all-star crew from all around the country.

Week 1: Remote Onboarding

Personally, this first week is the most critical part of a new hire. It often sets the tone on both sides for the entire employment.

How did I make them feel? Did I confirm in their mind that they made the right decision? Do they feel overwhelmed by the process, or well-supported?

This is especially crucial as a remote-first startup. Even though you’re going to be an asynchronous team, the first week involves a lot of face-to-face conversations, Q&A and going the extra mile to support your new teammate.

Each hire gets a small welcome kit right before their first day. We personally built and mailed each one. They got a couple of Punchlist T-shirts, stickers, a pin, and a note from Nic and me. Make them feel that we are treating this with personal care, and they aren’t someone filling a spot.

Sidenote: We originally thought about having each new hire come to Atlanta for their first week (where Nic and I are based). We felt this would allow for consistent onboarding, a chance to have more natural conversations, and ultimately a better opportunity to have a great first week. However, we ended up scrapping that idea because of Covid-19, and learned that a few weeks of onboarding remotely actually worked out very well.

(Plus, we flew everyone down for an all-hands retreat about a month in. More on that later.)

Agenda

For that first week of remote work, we split most days in half. 

The first half of day one was Company onboarding: Organization Mission, Vision, Values, and Product Walkthrough. The second half, free time to look through all the resources, and ask questions about what was covered.

Day two involved Department-specific onboarding. This is more focused on the role and starting a dialogue about what that department’s goals and OKRs would look like.

Then, on day three, it was conversations around communication processes, systems and tools. The back half of those days was on getting set up on the tools, or self-guided product education (poking around the Punchlist app).

Ideally, we were trying to make the information digestible while still giving each person the opportunity to process and reflect on what they were hearing. That typically led to each person having a couple of questions the next day on something they heard the previous morning.

Asynchronous comms tools we use

Here’s a quick list of our tool stack, including our own app, that we use to stay collaborative and efficient as a remote async team.

  • Notion – The “source of truth” for Company resources, documentation, research, anything that’s relatively evergreen and better-suited in database form. 
  • G-Suite – Google Docs, Sheets, Presentations, Calendar and Gmail. 
  • Slack – Our main communication tool for conversation and quick collaboration. 
  • Asana – Our main task management tool, to allow visibility across all departments, and move the work forward efficiently.
  • Loom – For quickly briefing or screensharing something asynchronously, without having to schedule a meeting.
  • Calendly – For booking anything external without extra back-and-forth.
  • Frame.io – For video reviews, and even sharing insights on customer interviews.
  • Punchlist – For reviewing / commenting on designs, landing pages, website edits and presentations. Gotta eat our own dog food, after all.

How we work asynchronously 

We took a lot of inspiration from organizations that have been doing the async thing a long time: Gitlab, Lullabot, and Twist. Then we wrote down the general themes of the things we felt were important about asynchronous work. 

  • Meetings: Do not have a ton of meetings. Prioritize action over planning. Always think about how this could be done without a meeting.
  • Availability: Work on your own schedule, but communicate progress. There are no strict “office hours” or expectation of being online 9-to-5.
  • Communication: Avoid “Are you there?” messages. Communicate more like email with enough detail to avoid back-and-forth. Loom and Punchlist projects work great for this.
  • Document: Understand how to leverage the tools we have, and update them regularly.

While trying hard to limit the synchronous meetings we have, I still think with a product as detailed as Punchlist, we need to be pretty conscious that it might take a little more syncing up at the beginning. It’s more important to get everyone unblocked and informed. Then as we evolve, we make the async workflow work better.

Team retreats

In lieu of in-person onboarding, we committed to having quarterly team retreats. For the first event, everyone flew into Atlanta, and we spent three great days together. It was the first time we had met, so the days were pretty evenly balanced between making progress on company goals and just getting to know each other.

Here are a couple of highlights from our retreat:

“You in 3”

Since we had never physically met before, one thing we pulled from Techstars was an exercise called “You in 3.” These quick presentations involve telling everyone in three minutes and 3 slides about your younger self, your culture, and something unique about you. A bonus slide was a gif about how you feel about this new adventure. “You in 3” ended up being a fantastic way to kick off the retreat and led to a lot of insightful conversations during the retreat.

Values Workshop

We collaborated to evolve our core values, framed around this idea: “What type of company do you want to work for?”

Nic and I, in the previous year, wrote the kinds of values we felt we wanted to focus on. (See: Hiring section above.) But now that we had a full team, we revisited to make sure the team’s input could shape our values further.

Guest Speaker

For the engineering team, Nic invited Brian DeShong, VP of Engineering at ShootProof to meet with the team and give some thoughts around an approach to building products with scale and stability in mind. Brian also shared advice on how to maintain a healthy engineering team. Brian’s team at ShootProof is years ahead of us, but this talk gave us an opportunity to learn from someone with hands-on experience.

Goals & Vision

We also did more typical things like a state of the product, goals for Q2, and some collaborative planning. As the founder this was my turn to share: where we started, how far we’ve come, and where we’re headed. 

This presentation ended up sparking more fruitful conversations cross-team about areas of focus, new features, and problems we need to solve together.

Overall, we’re all looking forward to the next retreat – which will take place in a different employee’s home city. 

Collaborative, Not Prescriptive

If I had to put a number to it, I’d say the team retreat was roughly 60% fun and bonding, 40% getting things done as a group. And our overall breakdown of day-to-day work is probably 80% asynchronous, 20% synchronous.

It’s valuable to have your remote team all in the same room from time to time (e.g. every 3 months), even and especially if you’re async first. And surely you’ll have weekly planning meetings and 1-on-1s that require face-to-face Zoom calls. But there isn’t a magic formula for how frequently to do this, or a one-size-fits-all agenda.

One guideline is to let your employees create the process together, and empower them to own it. Collaborate, don’t prescribe. This goes for the retreat planning, as well as other systems and workflows you’ll come up with together as an asynchronous team. It’s less about, “here’s how we’re doing it,” and more like, “How would you like it to be?”

Is your team remote & async first? Do any of these principles resonate with you? Let us know on Twitter @Punchlist and let’s chat. 

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Pete Bernardo

Pete Bernardo is the Founder & CEO of Punchlist, a TechStars Mentor, and occasional pizza maker. Former EVP at Three Five Two, Inc, Pete has 20 years of design & development experience across clients like CNN, Porsche, American Express, and Microsoft.
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