How to collaborate better in 2O2O

We asked designers, product managers, founders, and tech leaders to tell us about their main insights from 2O19 and share their advice for collaborating better in 2O2O.

Communicate asynchronously by default

To improve collaboration in 2020, stop putting important information in chats. It’s too easy to get missed or become lost. Use an asynchronous channel so people can respond to things on their own time. Communicate asynchronously by default and only when needed escalate to synchronous calls or meetings. Of course, we do all this in Basecamp.

Ryan Singer

Author and Product Strategist
at Basecamp

Ryan Singer on the problems with Agile today

Focus and communication trump new and shiny tools

Several trends came together in 2019, resulting in a new form of work that leaves me with mixed feelings. Specifically, the growing popularity of Slack, Zoom, and #NoCode integration surfaces (thanks to services like Zapier) enables team members to work more atomically and autonomously — at their own pace and asynchronously. This affords individuals more flexibility in their day-to-day work life, but can also introduce interruptions if workstreams aren’t sufficiently firewalled and unanticipated dependencies arise.

So, we’ve disaggregated work and given each contributor larger areas of responsibility. This offers more ownership, but can also increase coordination costs between teams. If you stumble upon these situations as a team leader in 2020, it’s important to reiterate the North Star metric. When frustration bubbles over because things don’t pan out as planned or there are blocks, it’s important to address root causes rather than overly focusing on the individual. Focus on transparency and honest communication, instead of shame. People should feel empowered to learn from the inevitable mistakes that are all part of maintaining momentum in today’s competitive environments.

As an ardent participant in the Product Hunt community, I’ve also noticed a growing trend of scalpel-sized digital tools launching to address particular pain points that larger, more generalized tools don’t solve — at least not without third-party extensions or integrations.

With this surfeit of good-looking new apps, I’ve spent an unreasonable amount of time searching for, testing, and comparing tools, hoping to uncover the Holy Grail of productivity…when really I ought to stick with the imperfect-but-familiar solutions I already know. When it comes to collaboration, focusing on tools that will get the job done and get feedback quickly is what’s important! So if I’ve learned something about collaboration in 2019, it’s that I need to be careful not to get tricked into looking for the “perfect” tool when really I just need to focus and work closely with my collaborators to maintain momentum.

Chris Messina

Hashtag inventor, speaker, and product designer

Chris Messina on building and scaling products that matter

Combine live and virtual interactions for better results

I think that we’ll see a mix between virtual and in-person collaborations and much more interactivity. Recently, one of our instructors at Product School gave an awesome webinar where people were able to answer a poll in real-time, and then discuss the results together—even though the speaker and attendees were not together in the same physical place. This is where technology takes an important role in the future of collaboration. Human connection and interaction are so simple, and yet so easy to overlook. Times are changing, and I imagine we’ll see much more of both in the new decade.

One of my biggest insights for 2020 is that when you collaborate with someone, you become a team. Even if you’re looking to get different things out of the collaboration, your goals are two sides of the same coin. Treat the person/people you’re collaborating with as members of the team. Empathize with them, make a human connection with them, but don’t be afraid to negotiate. If the way you’re communicating causes more problems than it solves, work together to find a better way to work. For example, if the email thread you’re in has turned into a confusing mess (happens to us all!) then suggest jumping on a video conference to clear things up. Or if you’re not in the same city, suggest using a digital tool that can remove the collaboration hassle from your work.

Carlos González
de Villaumbrosia

CEO at Product School

Mastering communication: a product manager’s superpower

Be remote-inclusive and embrace visual workspaces

The biggest trend I see is that everyone is remote. Information workers have lives after all, and in this day and age, it’s less of a requirement for people to be “butts in seats” for 40 hours a week. If you have a meeting with six people, it’s a guarantee that at least one person will be remote. This means there’s a huge new need for visual workspaces like Miro between offices – including home offices and even the car!

In addition to the written word (emails, Slack messages, wiki pages, etc.), people are turning to more visually focused tools in their collaborative work. The phrase “the meeting hasn’t started until someone is at the whiteboard” has never been truer in my opinion, and in asynchronous work this is also super true. It’s becoming very common to accompany the sharing of a document with a short Soapbox video (a free tool from Wistia) which adds color and the human element of explaining, which adds energy to our collaborative communications.

In 2020, I suggest trying new things! Try everything under the sun to get your team collaborating in a distributed manner, keeping the visual and enhancing the human elements of storytelling that inspire us to create and execute in the workplace.

Chris O’Donnell

SVP Product at HubSpot & bandleader at The Providers

Building a culture of innovation at HubSpot

Create space for deep work

2020 will be the year we really internalize that the recent uptick of next-generation collaboration tools (Slack, Zoom, etc) that significantly reduce the friction of collaboration has come at the cost of the ability of teams to do deep work. We’ll start to learn that not all friction in communication and collaboration is a bad thing and start to create new norms on how to effectively cope with the new reality these technologies have manifested.

Sachin Rekhi

Co-founder & CEO
at Notejoy

What every product leader should know about collaboration

Invest in your facilitation skills

We believe that in 2020, more and more classic meetings will be replaced by strategic gatherings that adopt a workshop format. This will enable teams and individuals to make better decisions faster and be more time-efficient while staying on the same page.

Remote for the win! Being able to collaborate across time zones is part of our DNA. As a company running Design Sprints, 2019 was an important milestone, as we’ve bullet-proofed our Remote Design Sprint method and shared our Miro template with our audience.

Our biggest suggestion is to stop having meetings where the outcome is just another meeting. Use Miro to document, brainstorm and align your team, regardless if you’re remote or not.

Ana Oarga

Co-founder at Just Mad

Razvan Burciu

Co-founder at Just Mad

Why innovation fails, and how Design Sprints can help

Build trust and transparency to reduce silos

One lesson I keep having to re-learn is that the most effective product development teams are those that have the best collaboration skills. When effective communication breaks down, so does the pace of value delivery.

In 2020, products that break down “information silos” are going to rise and win. Many applications, in the pursuit of becoming more specialized, are actually creating larger information silos – preventing collaboration and information sharing. General applications that solve this challenge, like Zapier (which allows data from one system to be leveraged and actioned in another system), are going to continue to expand and gain in popularity. On the function-specific side, I’d also expect to see a rise in applications that prioritize accessibility and collaboration.

My advice for 2020 is about building trust. Being able to take a hard and honest look at where your team is bottlenecked or breaking down is a crucial part of improvement – but if you don’t operate in a high-trust environment, work to improve that first instead.

Jeremy Wight

VP of Product & Engineering
at BaseHQ

A manager’s guide to distributed team leadership

Make sure you play as a team

I think in 2020, more companies will realize that successful collaboration doesn’t necessitate being side-by-side in office cubicles or being physically present together in the conference room. As a fully remote team of 35 spread across North America, we’ve learned first-hand that working remotely doesn’t have to mean sacrificing the ability to collaborate successfully. We’ve seen the investments we’ve made in practices that foster remote collaboration pay dividends in our employee engagement and happiness levels, and in our company’s success. My advice is to keep in mind that collaboration is by definition a team sport! If you’re looking to make changes or improvements to the ways you work together, ensure you gather feedback and opinions from your team. This feedback will help you implement process changes that are rooted in team buy-in. A simple survey or feedback in Google Forms will allow you to gather your thoughts and get the information you need without investing a lot of money or time.

Chloe Oddleifson

Director of People Operations
at Dribbble

Building and hiring distributed product teams

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