4 non-cringeworthy team-bonding events that people actually enjoy

Here’s what 1,000 managers in The Watercooler said their employees enjoyed most as a team-building activity.

Team bonding — known to some as “forced fun” — can bring feelings of dread and resentment to many employees. And who can blame them? When thinking of team bonding, many people picture awkward trust falls or hours spent with a facilitator asking corny questions.

However, a team does need to feel connected in some way. You can’t work well together if you don’t trust each other — let alone, know each other. And getting to know each other, while that can happen organically over time, only gets harder the bigger the team gets or the more spread out your office is.

Particularly for new employees, an effective team-building activity can go a long way. It’s rare, dedicated time for folks to not talk about work, relax, and just have fun.

I asked members of The Watercooler, our online community of almost 1,000 managers in Know Your Team, what their most successful team bonding events were. Below were the top four mentioned. Feel free to tailor these ideas to fit your own team dynamics and preferences.

Work ‘n Travel

Few experiences are as memorable and unique as traveling somewhere novel. For the past couple of years, one Watercooler member’s company spends a week together as a team, working remotely and traveling. So far, they’ve been to Lisbon, Portugal, and Poland. (And they already have their destination picked out for next year!) For them, it’s been a perfect way to spend high-quality time getting to know each other, while also getting to have a common shared experience of traveling.

Team Volunteering

Contributing to the community around you, together with your team, is a fantastic, non-cliché way for everyone to feel more connected. One Watercooler member’s company volunteered at a local food bank when everyone was in town for a company meeting. They spent the day providing thousands of meals to people in need while also bonding as a company.

3+ Lunch Fridays

Possibly the most common team-bonding event that teams seem to do is to sponsor lunch outside the office on Fridays. Several managers in the Watercooler mentioned how their company will cover the cost of lunch for groups of three or more employees if they go out to eat on Fridays. This in fact incentivizes folks to get out of the office and socialize a bit with one another.

Cereal Day

It sounds odd, I know. But a Know Your Company customer and Watercooler member shared how surprised she was that a seemingly insignificant team-bonding event had such a big effect on her team’s morale. Every month, she brings in a box of everyone’s favorite cereal to one of their most intense days of the month: The strategic planning meeting. It was a small, quirky move — not any big grand gesture – and it was a big hit with her team.



P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

How to have a good relationship with your boss when you’re working remotely

Four best practices to help you work well with your boss when you don’t see them face-to-face all the time.

What does her Slack message *really* mean?It’s easy to second-guess yourself when your boss pings you. You want to have a good relationship with your boss — but it’s not always the most natural of things. And that difficulty only increases when you’re working remotely.

When you don’t see your boss face-to-face all the time, the room for miscommunication, misinterpretation, and misalignment expands. You can’t read body language. You can’t go tap your boss on the shoulder to ask a question. You can’t even show her with your physical presence that you are, yes indeed, working.

Yet maintaining a good relationship with your boss is crucial. According to Gallup, “managers account for at least 70% variance in employee engagement scores.” You’re less stressed when things are going well with your boss — so you want to be particularly thoughtful about managing that relationship while you’re remote.

The good news is that this is a common scenario faced by 1,000+ managers in The Watercooler, our online community for leaders from all over the world. Based on their conversations, I’ve pulled a few tips on how to maintain a good relationship with a manager while working remotely…

Proactively share progress

For your manager, understanding what progress you are making on your work is surprisingly opaque. Your manager is often juggling quite a few tasks — be it working with a client or negotiating a partnership — and they want to know what you’re working on ideally without having to hover, check-in with you constantly, be “Big Brother” about it. As emphasized by leaders in The Watercooler, this desire to know what you’re working on is only heightened when you’re remote.

To help shine a light on this for your manager, proactively share as much detailed progress as you can. This can come in the form of writing up a bit more granularly in your bullet points in your weekly summary about the project. Or it can come in the form of you even volunteering that you send her a daily summary of what you accomplished that day. Helping your manager understand the results you’re achieving brings them a ton of ease and peace of mind to their job.

Play detective about their working style

Working well with someone has a lot to do with understanding how they like to work. What are their preferences and habits? What’s the way they’re used to having things done? As a remote employee, not seeing your manager face-to-face, it’s very easy to unintentionally annoy your manager or do something that isn’t within their zone of what they’d prefer. When you know their working style, you can better calibrate from afar how to communicate with them, work with them, and deliver above and beyond what they expect.

To get a sense of their working style, here are some questions you can ask them:

  • What do you value most in a coworker?
  • Who in the organization do you admire, and why?
  • Do you like time to think something over, or do you prefer to talk about it right away?
  • When do you not like to be interrupted during the day?
  • Are you a morning, afternoon, or a night person?
  • Is there anything you feel like you might be a little more particular about than most?
  • What, if anything, worries you or keeps you up at night about the company?

Try asking one (or more) of these questions during your next one-on-one conversation, when your manager asks you, “Do you have any questions for me?”

Rigorously clarify expectations

Arguably the most challenging part of any working relationship — regardless of if you’re remote or not — is to get on the same page in terms of expectations. Do you know what is expected of you, and does your boss know what is expected of her? Often times, when you’re both in-person, these expectations can be hashed out over time: You listen, observe, learn, ask others around you, and pick them up. But when you’re remote, because of limited in-person interactions, those conversations might not come up as readily. Accordingly, it’s imperative for you to ask questions that clarify, uncover, and confirm what these expectations are.

Here are some questions you can ask your boss to start to clarify these expectations:

  • What things will I need have accomplished this year for you to view me in this role as “successful”?
  • What does quality work look like to you?
  • What should standard working hours be for both of us?
  • What is the best way to contact you during those hours?
  • What form of communication should be used to communicate with you during that time?
  • What’s the expectation of how quickly I should respond when you reach out to me during those working hours?
  • What form of communication do you prefer when there’s a hard topic or conversation? (E.g., In writing, over the phone, video call)
  • If I need your attention on something urgent, what form of communication do you prefer? (E.g., Slack, an email, a phone call)
  • What do you consider “urgent” versus “not urgent”?
  • If I have any feedback for you, how would they prefer you receive it: In writing, over the phone, or during a video call?
  • If I have a suggestion about something, how would you prefer you receive it: In writing, over the phone, or during a video call?
  • If I have a questions, what form of communication should I pose the questions to you? (E.g., In writing, over the phone, during a video call)

One Watercooler member also recommended to have a small cheat-sheet with remote communication expectations with best practices like:

If you are going to be offline to take care of some personal things during the day, please notify your direct team on their Slack channel.

If you are planning to work at odd hours schedule for a few days please let everybody know up-front.

Make time to get to know them — in person or over video

When you work in the same physical location as your boss, the opportunities to build trust and rapport are plenty. You can chat with them over lunch and ask them about their hobbies, or go grab coffee in the afternoon and catch up what’s been going on in their life recently. Even bumping into them in the hallway of the office and giving a friendly “hello” fosters a sense of affinity between the two of you. When you’re remote, those moments of social interaction no longer exist. For managers who are working with remote employees for the first time, this is often a shocking and noticeably absent part of a boss-employee relationship.

In the Watercooler, leaders had some recommendations to make sure you’re still getting to know your manager on a personal level (feel free to suggest them as ideas to implement with your manager):

  • If you happen to live nearby your manager, try quarterly in-person lunches.
  • Once a month or once a quarter, have coffee over video for 30 minutes to an hour to chat about life. (Here are some icebreaker questions if you’re never really sure what to talk about or what to ask your manager.)
    Video is always on for calls (unless there is a tech reason)
  • Take a few minutes to catch up on life during the beginning of a one-on-one meeting.
  • Twice per month, during your one-on-one meetings over video, chat about whatever they want to talk about. It usually covers a bit about work or maybe just catching up on what is happening in their lives.
  • Do video chats instead of just calls. Many Watercooler members recommended this. They often ask that people turn on the video and “it makes a huge difference.”

While never easy, focusing on these four areas as a remote employee can help better your relationship with your boss tremendously. If you want, you can even use this article as an excuse to start the conversation and perhaps try a few of these ideas. (For example, you could send an email saying: “I read this interesting article about working well remotely, and thought we might want to try turning on video more often instead of just doing phone calls…”)

These tips have worked for our Watercooler members — I hope they work for you too.

P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew)

Breaking the (remote) ice: 5 tips for icebreakers in distributed teams

Our most popular recommendations for team-bonding, regardless of the distance separating your remote employees.

Believe me when I tell you that I adore running a remote company. It’s enabled me to hire and work with folks I could’ve never have hired locally. It’s helped me work with fewer distractions and greater focus. It’s given me more flexibility to see my family and spend time on side-hobbies that bring me joy… I could go on 🙂

But, I’ll admit: Being geographically disparate can also be isolating. As a remote company ourselves at Know Your Team, we don’t pretend that there are zero difficulties to running a remote team. There are quite a few — and one of the biggest is making team members feel welcome and connected to the company when they live on the other side of the country.

Think about the last time you started a new job. Do you recall feeling overwhelmed or disconnected from your coworkers? Now imagine that you’re facing all the same pressures and uncertainty but from a few hundred (or thousand) miles away.

For all the upsides to remote work, those benefits can be hampered by the loneliness that some folks can feel if they don’t get to interact with other team members on a regular basis.

Here are some tips for creating great icebreakers to help build a better sense of connection within your remote teams:

Ditch the dull general questions in exchange for specific questions.

How many times have you been asked, “What do you like to do on weekends?” or “What are your hobbies?” Eye roll. So many times. The questions feel rote, so the answers become rote. Just as when you’re seeking out meaningful feedback about the company, you’ll want to ask meaningful social questions to get meaningful social responses, too. Unsure where to start? Check out the 25 specific best icebreaker questions to ask.

Get folks face-to-face when you can.

Where were you the last time you participated in an icebreaker activity? It probably wasn’t from your home office. Just like in-office icebreakers, remote teams’ icebreaker conversations should happen via video chat, or (ideally) in person at a company retreat. One of our remote clients, Balsamiq, is known for their all-team retreats that focus getting everyone, face-to-face together to have a good time.

Schedule in the time for socialization.

Nothing happens unless you carve out the time to do it. That’s something Paul Farnell, co-founder of Litmus (another one of our customers), emphasize. He’s said that you have to “make time for socialization.” At Litmus, he describes how “a few times a year, we have company get-togethers and smaller teams meet in-person more often. Week to week, we get Coworker Coffees, drink beers on Skype, and play video games online. And we invite local employees to the office every Thursday.” Schedule in time for folks to break the ice — or else it just won’t happen.

Assign a buddy, and switch it up.

Another way to keep icebreakers feeling fresh, especially in a remote team, is to switch up who is getting to interact with who on your team. At Help Scout, another client of ours, they organize 15–30 minute coffee breaks between randomly assigned team members called Fikas. By assigning someone a buddy for a period of time, you take the hard work (and sometimes awkwardness) of leaving it up to the employees to figure out who they should get to know better. And, switching up the assignments keeps the getting-to-know-you process from becoming stale.

Keep it light.

Icebreakers are supposed to be fun — so don’t overthink them, or be too intent on “this needs to build trust in my team.” A overly forced icebreaker is never fun. Rather, reflect on your team’s personalities and interest, and consider how you might give people a reason to laugh, joke, and feel a bit more connected with one another. The best leaders know that injecting some levity in an otherwise intense work week can make a big difference. A light question such as, “What’s your favorite breakfast cereal?” yields surprising levels of engagement.

While team icebreakers can seem like a “nice to have,” in a remote team they are “must-haves.” Since your team isn’t interacting face-to-face every week, the miscommunication, trust issues, and poor team dynamics that can bubble up are only exacerbated if you’re not findings ways for your team to connect regularly. So give one or two of these tips a try, and remember how beneficial team-building icebreakers can be for a remote team.


Top 13 Leadership Lessons from AMA with Amir Salihefendic, CEO of Doist

As the CEO and founder of a bootstrapped, remote company with over 13 million customers, Amir shared his leadership lessons learned with our online community, The Watercooler.

Every few weeks, we invite one of our 1,000+ Watercooler members from all over the world to participate in an “Ask Me Anything” (AMA) session. It’s an opportunity for us fellow managers, executives, and business owners (including me!) to gain in-depth insights on how to be an effective leader.

Last month, we were honored to host Amir Salihefendic, CEO and founder of Doist — the software company responsible for Todoist, a productivity tool used by over 13 million people. Amir’s company is a remote-first, bootstrapped and independent company with ~50 team members from 20 different countries.

Originally from Bosnia, Amir grew up in Denmark, studying Computer Science. Prior to Doist, Amir was part of the founding team of Plurk, a Twitter precursor used by millions of people that to this day, continues to be one of the most popular social networking sites in Asia.

I learned a lot following Amir’s AMA. Here were the top 13 questions and answers….

Question #1

How do your project managers deal with having team members in various time zones? Specifically when it comes to project meetings, sprint planning, demos, client meetings, etc…

Amir: Most of our work happens asynchronously. We used Slack for about two years before we figured out that real-time communication wasn’t a great solution, especially for a remote-first company like ours (we have people in 23 countries, spanning most time zones).

But even for non-remote companies, asynchronous communication can be a great deal. For example, I recently became a new dad, and it’s a huge advantage that I don’t have to be working at any specific times, so I can spend a few hours in the morning with Samuel without worrying about not being at work or affecting work of others.

We do use synchronous communication at times (e.g. Hangout meetings), but our default mode of operation is asynchronous.

I would recommend reading our article that goes much more in depth: Why we’re betting against real-time team messaging

Question #2

I’ve heard companies with remote teams say that remote only works if everyone is remote. Do you share this philosophy?

Amir: I share this philosophy. Remote work (especially as we do it) is an entirely new way of working. For example, we don’t have work hours, we value a lot the written communication, we do very few meetings, and most of the stuff inside the company is transparent and available to everyone (including most numbers such a revenues, daily actives or whatever else).

Question #3

Any advice or thoughts on how to build that team culture and shared sense of purpose from your experience with Doist?

Amir: Great question, Jeremey.

A lot of open-source communities (for example, Python or Linux developers) have incredible cultures, even if most of the work is being done in a remote setting. So I am very unsure if an office environment is needed to build cultures or to build innovation (e.g., Linux has changed the world, and most things run on it).

For us, our culture centers around critical missions that unite us (this is remote-work, productivity, and mindful team communication). There’s also a general feeling that the work we do is relevant and useful to a lot of people. We are also super picky to hire people that have a passion for the stuff we do.

Apart from this, we do have random meetings around the world and a company-wide yearly retreat (which we usually do in some exotic places), but I do think our missions are much more critical than anything else.

It should also be stated that our 5-year employee retention rate is 93% (only three persons have left voluntarily in the last 5 years), so I think it’s possible to build healthy cultures even in entirely remote environments.

Question #4

I know Todoist is bootstrapped and profitable but did you use some of your personal money from Plurk to fund Todoist and build a team or did you go back to full-solo developer mode and slowly got the company into the profitability path?

Amir: I spent very little of my own money. When I went to work full-time on Todoist, it was making a few thousand dollars in revenues per month.

As I increased the revenues, I hired people. The first people that joined had very small salaries (I have no idea of how I convinced them to join :-)).

Question #5

Was it hard to get the product to a point where you were at the same level of quality of tools like Wunderlist, Trello, and Basecamp?

Amir: Competition never drove me. I didn’t know about Wunderlist until very late. I was very ignorant about a lot of things (e.g., I never did market research). This strategy isn’t something I would recommend with my current knowledge 😊

I did lose a ton of time making Plurk, but I also learned a lot of stuff I could use. For example, that I should not raise VC funding and that I should do this in an entirely bootstrapped way. I also became a much better designer and developer, which was also super useful.

What hurt most was that Todoist was built for the web and not mobile. It took us a long time to create super robust mobile apps.

Question #6

How was the decision to work on Todoist after Plurk?

Amir: Todoist was a hobby for me and something I truly cared about. It wasn’t tough to switch to it full time or to imagine working on it for ten years (who doesn’t want to work on their hobby!?)

This said it took me many years to see the real potential of Todoist. I never imagined it would be multi-million dollar business…

Question #7

Are you still involved with engineering and development these days or do you focus all your energy on business and management? And, if you are not so involved anymore, was it hard for you to make the transition?

Amir: I still spend 25% of my time doing development, and I plan to continue to do this. Here’s how I spend my time:

We don’t have any pure managers inside Doist — we expect all of our managers to be doers as well. This works, since we try to hire people that are self-managed and that don’t need a lot of micromanagement.

Development and creating stuff is something I have done since I was 12 years old and I can’t imagine stopping doing this because the general practice is that leaders just need to manage others.

Hope this helped!

Question #8

With a turn-over so small like you mentioned, I imagine that Doist probably figured that out already. I would love to hear what are your thoughts on that and how do keep your individual contributors engaged for so long?

Amir: Like mentioned before in this AMA we don’t have people that just manage other people. This choice is rooted in that we believe that our people should be self-managed and we should do as little micromanagement as possible. We also highly value individual contributors, and the salaries are similar between a fantastic individual contributor and a team leader.

Question #9

How many levels of managers/leaders do you have and how are your departments and teams organized? Do you structure the teams around different products, features, or something else?

Amir: Here’s how our structure looks like:

  • At the top, we have a CEO, COO, and CTO
  • Then we have team heads, e.g., head of Android, head of iOS, head of marketing
  • Rest of the structure is flat (e.g., developer, designer)

We are in the process of adding more roles so people can feel like they are advancing their skills and careers.

We work in dynamic squads in 6 weeks cycles (and we usually do 2–3 weeks of pause between these cycles). A squad could be a designer, a web-dev, an iOS developer and an Android developer trying to improve a specific feature.

Hope this helped 😊

Question #10

I’d love to know how your team comes up with ideas for new features/products and how things get prioritized. Do you have the traditional structure where product/data team comes up with most of the ideas or do you have a different structure?

Amir: Great question!

Anybody in the company can make a DO proposal, and currently, we have 100+ of these. These are ideas of stuff we should be working on. I am attaching an example here:

On each six week cycle we then decide what we should work on using the following process:

  1. The team heads decide on a general theme for each cycle and for each product (could be improving the foundations)
  2. Before each period, each team reviews the DOs and suggests 3 to 5 DOs for the upcoming cycle. They also list massive internal DOs they might be working on (so we can plan better)
  3. I review each team suggestion and compile a DOs RFC, which is shared with everyone, and we can comment and change stuff
  4. We decide a final RFC, and the DO coordinator starts allocating people to DO squads

Question #11

How big is the company and could give a broad percentage of the size of the teams (Engineering, Marketing, Sales, Support, etc)?

We are currently 55 people spread around 23 countries.


  • 26 Developers
  • 9 Support
  • 8 Marketing/Growth
  • 8 Designers
  • 4 Finance/Business dev

It’s notable to know that we don’t have HR or sales. We are currently hiring an HR person tho 👍

Question #12

What’s the one thing you wish you would’ve learned earlier as a leader?

Amir: Doing scheduled 1-on-1s and investing time in making them better. We started to do 1-on-1s very late. I would even recommend them if you are a smaller company.

We use Todoist shared projects for 1-on-1s. Each 1-on-1 has a prepared agenda. We also add actionable tasks that result from the 1-on-1s. This makes our 1-on-1s much more structured and actionable.

Question #13

For many companies (remote or not), hiring is their #1 challenge. What are the key traits you look for when hiring, and how do you structure the hiring process at Doist to account for them?

Amir: We have a HELL YEA rule, inspired by Derek Sivers. When we hire somebody we need either “HELL YEAH!” or “no.” (no “yes” or “maybe it will work”). This simple rule has worked wonders for us.


Top 5 Leadership Lessons from AMA with Valentina Thörner, of Automattic

In our leadership community, The Watercooler, Val shared her expertise leading a world-class, remote support team in our first ever AMA. Here are the top 5 leadership lessons learned from it.

In our leadership community, The Watercooler, we recently kicked off a series of “Ask Me Anything” (AMA) sessions, featuring Watercooler members we respect and want to garner more in-depth leadership best practices and insights from.

Our first AMA featured Valentina Thörner, Happiness Team Lead at Automattic – a 600+ person remote web-development company most known for creating WordPress.com.

At Automattic, Val leads a seven-person support team, spreading from Scotland all the way to Thailand, and spends her days helping to find blockers and identify opportunities to make their work even more impactful. She is also currently launching concierge services for WooCommerce customers and improving their ticket quality via a review strategy.

Her AMA was overflowing with inquisitive, precise questions around leading support teams, improving employee morale, and being a remote leader.

Here are the top 5 questions and answers from the AMA…

Question #1:

“What kinds of goals do you set for happiness initiatives, and how do you measure their success?”

Val’s Answer:

We have a three year plan for our Happiness division, that ties in with a three year plan for the entire company. However, since we can’t directly influence product development or marketing activities, we focus on setting up processes that allow us to serve our customers and learn from their experiences.

Since we can’t predict the future, our long term goals are based on customer experience. We’ve coded our goal into v 1.0, v 2.0 and v 3.0 knowing that sometimes things take longer, and sometimes you can take a shortcut. By focussing on outcomes and intermediate milestones,
we give ourselves the option to experiment with different tools, processes, ideas without losing sight of the long-term goal.

For example, one goal (which will resonate with many of you who are involved with your support division) is to offer consistent 24/7/360+ customer support across all product support departments. There are several milestones to make this happen:

  • Figure out how to staff for 24 hours.
  • Organize weekend coverage
  • Find solutions for holiday coverage / vacation policies.

Depending on the support channels that you offer you can then divide this down into live chat coverage, response time for tickets, video call options, social media replies (or whatever are your channels).

By plotting these milestones for each channel on your timeline (or version line), you end up with tangible goals for the next mini versions (or quarters), for example:


  • reduce ticket reply time to 12 hours
  • offer 18/5 chat coverage on weekdays


  • reduce ticket reply time to 8 hours
  • offer 24/5 chat coverage

By the way, we usually stick to the next two quarter
With these short/term goals in mind (clearly relatable to the long-term goal), you can now start experimenting — and this is when you can actually bring your support staff on board to find solutions, or to surface resource problems. For example, when branching out into 24/7 support, we’ve realized that we need to concentrate hiring on certain timezones to be ready for growth in certain parts of the world. Being a remote company helps in this regard — no graveyard shifts for anyone.

So, for every happiness initiative, it’s important to tie those in with the bigger goal. If someone proposes a new tool: how will that affect our ability to get to our version goal? If you can make a good case for it, we’ll probably give it a try. And this is valid for both bigger projects (e.g. scheduling solution for a support division of 200+ people) as well as smaller projects (testing on demand concierge services for a subset of certain customers).

Define a hypothesis about how this will take us closer to our goal or accelerate us getting there. Test it. Analyze the result and we’ll take it from there. And that’s valid for individual Happiness Engineers as well as team leads 🙂

Question #2:

When you are trying to secure funding for your initiatives, what are the business cases you are using to convince execs that it’s the best investment of the resources?”

Val’s Answer:

I am usually involved in initiatives around Customer Support. Here the main questions to answer are:

  • How will this impact our customers? How can this make their life easier?
  • How will this improve/facilitate the work of our Happiness Engineers, and in what way?

Whatever the initiative you are trying to start, you probably have a goal in mind already. See how you can translate this into numbers. For example:

  • Can this tool save time for team members so they can answer more customer queries and thus reduce response times?
  • Will this new process improve customer will it save time for your team members so they can keep up with customer satisfaction and ultimately reduce churn?

Now, sometimes it is difficult to prove these things upfront. You might have a theory, an inkling, but you don’t have numbers yet. In this case, find allies to set up a little experiment.

For example, for a long time, we weren’t sure if live chat would work for something as complex as WooCommerce. It works beautifully on the WordPress.com site, but WooCommerce stores are usually highly customized individual solutions. So, instead of trying to roll out live chat with everyone all at once, one team decided to try it. They organized an experiment to offer live chat during a set number of hours for a month. We then analyzed the changes in incoming tickets during those hours, the customer response, etc. And suddenly we had numbers to work with and to decide if and how to move forward with this experiment.

The experiment was so small that the investment was minimal, and since it was an experiment to prove a potentially bigger opportunity, no-one vetoed.

So if you don’t have the numbers yet, design an experiment small enough to go under the radar of resistance and create those numbers.
Sometimes you’ll be wrong. Or you are too early. And that’s fine. At the very least you’ll have learned something, and you’ll reuse those numbers (that did not prove your current case) in other circumstances.

Question #3:

(Okay, this is more than one question hehe…)

“What do you think are the main challenges of being in a large fully-distributed team?

Are the teams organized around timezone overlap?

What do you think Automattic does differently that makes it capable to pull off remote culture at scale, while so many others fail?

How do you do social bond events? Do you have events like company/team off-sites?”

Val’s Answer:

What do you think are the main challenges of being in a large fully-distributed team?

Time zones. For example, I am in UTC+1 and start my day pretty early (thanks, kids). One of my colleagues is in UTC-8, so we have to actively plan to catch up. If a high % of the teams is in a similar time zone (e.g., we are still quite US-centered), then it’s easy to miss discussions if you are in another time zone. We have to actively work on posting these topics and their results, waiting a couple of hours so that other time zones have an option to participate.
To account for this reality, I have shifted my schedule a bit. Once a week I work two hours after dinner, when my kids are in bed, to get my finger on the pulse of what is going on in the US side of the world (and pick the brains of my colleagues in that timezone).
Cultural differences can also be a challenge, e.g., how the US sees vacation as a privilege and Europeans see it as their right. Summer vacation planning can be stressful if one party thinks taking off more than a week is irresponsible and the other party thinks that anything less then 2 weeks is disrespectful to one’s family.

What do you think Automattic does differently that makes it capable to pull off remote culture at scale, while so many others fail?

Some things that probably influence here:

  • Communication. This includes documentation. Document everything, communicate everything, post, slack, discuss, summarize — and make sure you have a search engine powerful enough to wade through all of your internal creations (knowledge base, blogs, slack conversations, internal tools) so that past discussions can be referenced.
  • Trust. We mostly work on goals. Yes, your full-time position will most likely take you 35–40 hours a week, but no one will time track you (though, as a lead, and for productivity purposes, I’d encourage you to track yourself). We kind of trust that everyone is doing their best. And curiously, this has the effect that most people actually do do their best. And I like to think that those who don’t, don’t last too long.
  • Company — employee fit. We have a very intensive trial process during the application process. This is not only for us to find out if the person is the right fit, but also for the potential employee to evaluate whether they like this kind of work. Remote work requires a lot of self-organization and self motivation, and those coming from a “normal” corporate job sometimes realize that this environment is too lonely and too entrepreneurial (in the sense of organizing yourself). And that’s fine. We give both parties the time to figure out if this can work for both parties.

How do you do social bond events? Do you have events like company/team off-sites?

Yes we do. Once a year the entire company meets (well, let’s say 95%) for roughly a week. Each team will also have one team meeting a year, usually for about a week. Some projects and some task forces will also meet in person occasionally. These meetings are usually a mix of project work and socialization (and yes, some tourism). Outside of these meetups it very much depends on the team to organize their activities. My team does quarterly pizza parties, where we all have lunch/dinner (depending on the time zone) together and talk about stuff (anything but work). Other teams have joint challenges where they cheer on each other — it very much varies per team though.

And then, of course, there’s about 500 slack channels where you can bond with people around joint interests: dogs, cats, running, WOW, cooking, knitting, book club, toddler parents, linux users, home owners, etc etc

Question #4:

“What are the top three skills or characteristics you look for in hiring a support team member?”

Val’s Answer:

  • Ability to learn quickly.
  • Empathy.
  • Attention to detail.

Everything else can be learned.

Question #5:

“Can you share a little bit about your approach to developing and rolling our a new service offering (re: concierge services for WooCommerce)? We are trying to do something similar internally and I’m finding that designing a new service is a bit more abstract and challenging than focus on a product.”

Val’s Answer:

  1. Define your goal. For example, in our case, we want to increase renewals and reduce refunds. Boom, there are your numbers to track against.
  2. Define a test cohort. In our case that were people that have just bought product X.
  3. Depending on how many data you need, define how many people you want to include in your experiment and decide a timeline. In our case, we did a 1-week experiment past April (to find out if anyone would be interested) and are now doing a more structured 6-week test.
  4. Get volunteers to do those calls.
  5. Set up the documentation so your volunteers know what to do.
  6. Set up a booking system (youcanbook.me, calend.ly would work).
  7. Make sure you get an invitation to people that should participate (worst case: send them out manually — that’s what I do currently).
  8. Create a template so your volunteers can post comprehensive notes of their calls.

And then analyze your data after the experiment.

You might find out that people tend to have the same questions over and over again. You might find out that you have 60% no-show. You might find out that everybody asks how to pay for a second session — and then you can take it from there.

On Yonder Podcast 🎙: Best Practices for Leading Remote Teams

From communication to delegation to meetings, I speak on what we’ve observed to be the most important things for remote leaders to keep in mind.

Recently, I was interviewed by the incredible Jeff Robbins on the Yonder Podcast about best practices in managing remote teams. I had a blast. I’ve had the pleasure of knowing Jeff for several years, as he used to be a customer of ours while he was the CEO of Lullabot.

In the podcast, we chat about:

  • How do remote leaders need to communicate differently?
  • What the best practices of managing remote teams?
  • How does introversion or extraversion affect how you lead a remote team?
  • To what extent is respecting quiet, uninterrupted time important for managing a remote team well?
  • What are the advantages of leading a fully distributed team, versus a partially distributed team? Are there best practices for each?

Listen to the full podcast here.

Also, if you’re looking to become better as a remote leader, you might enjoy a few of these pieces:

Hope you find it helpful as you lead your own remote team.