How to Run a Remote Team

in less than 4 hours of meetings/week

skritswap
skritswap
Mar 13 · 22 min read

by: Melissa Kargiannakis, Founder & CEO of skritswap

The winning recipe for remote work is a huge helping of autonomy, a dash of accountability, a generous helping of flexibility, and a pinch of structure.

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The limit doesn’t exist, because the technology DOES exist! Zoom, Google Meet née Google Hangouts, etc. It’s there. It works. Use it. (And yes that is a Mean Girls reference because this is not your average tech blog post and I don’t feel like referring to sports or superheroes).

1. Intro

Remote work is the unintended benefactor of the global Coronavirus/COVID-19 pandemic. Everyone is doing it and everyone is talking about.

This is a tactical manifesto on how to run a remote team.

People usually write from the employees’ perspective on how to time manage or survive the lack of social interaction. What’s missing is the managers’ guide to keep work running smoothly.

Below, I’m sharing a step-by-step guide on how to run a remote team; and in less than 4 hours of meetings per week. I will detail everything. From the meeting times and structures, to the questions you ask your team. From the tools we use, to the operational approaches.

I’ve been managing teams for a decade and our fully remote team since Jan 2018. We’ve had these structures since it was 3 of us. We’ve iterated a little to achieve this smooth rhythm. Now there’s 6 of us in 4 cities and 2 time zones.

The winning recipe for remote work is a huge helping of autonomy, a dash of accountability, a generous helping of flexibility, and a pinch of structure.

First, read what Andreas Klinger says to determine what type of remote team you are. Skritswap is a Remote First Team by his definition. He gives us the theory and philosophy that grounds my practical tips here.

Once you master “remote work” you’ll never go back to a full 5 days in the office every week. I promise.

Table of Contents

6 key sections:

  1. Intro
  2. Meetings
  3. Tools We Use
  4. OKRs: Objectives & Key Results
  5. In Real Life (IRL) Matters
  6. Mindset

2. Meetings

🕓 Cadence

Here’s our overall meeting layout <4 hours/week:

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Overall skritswap meetings each week.

📈 Structure & Accountability

Team Huddle Tues (7–12 mins):

Purpose: accountability, connection, communication, learning. We hear what everyone else is working on to offer ideas and keep up with one another.

Who — everyone:

  • Founder & CEO
  • Executive Assistant
  • Senior Full Stack Dev
  • Full Stack Dev
  • Comp Ling
  • Plain Language Expert

Prep : every Monday the whole team fills out these specific Qs in a slack channel before Tuesday:

  • Blockers
  • Highlights
  • Lowlights
  • Completed
  • Working on Next

Agenda:

  1. Each person shares their Blockers & Working on Next (20 seconds ea.)
  2. Group highlights (people shout ’em out if they got ‘em)
  3. Learning on the job: validates we are all growing and learning. 1–2 people describe something they learned that is a transferrable skill. Because 80% of learning is done on the job not in a course (2 mins)
  4. End with 3-minute guided meditation. This is so that we end the meeting peacefully and go back to work engaged and ready to go. Science shows meditation improves performance and productivity.
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Slack /remind notification for our Team Huddle Tues

Team Huddle Thurs (12–20 mins):

Purpose: strategy, alignment, communication. What I call “compass calibration” where we align our goals and mission. We check-in on each area of the company and how it is performing against our OKRs and overall company strategy.

Who — everyone:

  • Founder & CEO
  • Executive Assistant
  • Senior Full Stack Dev
  • Full Stack Dev
  • Comp Ling
  • Plain Language Expert

Prep ❓: I need to refer to the minutes from different meetings

Agenda: It’s where I as the solo founder, will present key decisions from each area of the company:

1. Overall company strategy — say it once, twice, 5x over. That is how you will get people on the same page always.

2. Management

3. Development

4. Comms/marketing

5. Sales — I’m not really accountable to “anyone” for sales activity, just sales outcomes to our investors. I report to my team each week about who I’m calling, what deals I’m working on, how big they could be, etc..

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Slack /remind notification for our Team Huddle Thurs

Feedback Fridays (3 -12 mins):

Purpose:

  • Manage each team member individually
  • Give people a private space to address concerns (leads to psychological safety)
  • Share ideas in case they are too shy to share in the group meetings (helps folks who are more introverted and then we can come up with a plan to help them share it with the team or I share it and give them credit)
  • Tell me how they think they are doing
  • Hear my evaluation of their performance
  • Tell me how they think I’m doing. Share what I need to continue, stop, and start. Staff can share any feedback for me, whether they saw something or it was a direct interaction with us. I encourage people to call out: “when you said X to Y” or “when you said X to me”
  • Also gives me the time/space to discuss behaviour, attitude, and performance, in the spirit of “praise publicly and correct privately”.

Who:

· Founder & CEO (me)

· each team member individually 1-on-1

Prep : Every week on Thursdays before we meet on Fridays, my team will individually rate the following in a slack message just to me.

Rate each item for the week on a scale from 1–5:

1. Output

2. Results

3. Personal Growth/Professional Development

4. Motivation

5. Feedback: What would you like me to start, stop, continue? (free form answer)

Agenda: discuss the above

Development Meetings Mon & Thurs

Purpose: product planning, performance tracking, product usage, user feedback, etc.

Who — development (product) team:

· Founder & CEO (acting as product manager)

· Senior Full Stack Dev

· Full Stack Dev

· Comp Ling

Prep ❓: whoever is showing Amplitude has to be ready and logged in before the meeting starts. Everyone has to ensure trello is up to date before the meeting. We take light notes in the #dev slack channel but most of what we discuss gets recorded right in trello cards and made actionable immediately. More on that in a minute.

Agenda:

  • Mondays we look at our Amplitude Data, we alternate who logs in and leads us through the data each week
  • Thursdays we check-in on how we are doing with our OKRs

How does this schedule interplay with product deployment schedules?

  • Deploy Thurs am before the dev meetings. QA and test Fri and Mon am
  • An iteration note: we used to do 1 dev mtg/week and had 2-week sprint cycles. I suspect we will go back to 2 week sprint cycles in the next 8–12 months. Currently, we have 2 meetings/week and 1 week sprint cycles. I suspect the increased frequency is at least partly due to being remote first.
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Actual screenshot of my calendar. Shows only the core meetings. Clearly a lot of whitespace to get work done.

🖥️📲 Ad Hoc “in-the-moment” Meetings

We have this thing where we “jump in” to different meeting links.

“Hey can we jump in for a second?” = “Hey can you come take a look at this?”

We say: “can we jump in for a second?” in Slack and send a Google Meet link. We “jump into” the link and share screens to figure things out.

We treat it just like “can you come look at this?” if we were in the same office, which we are not.

Google Meet, Zoom, etc. the medium is almost irrelevant though the ability to screen-share is usually necessary for these meetings.

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Actual screenshot from a meeting where we “jumped in” to look at this doc together quickly.

🤫 WORK BLOCK

Put WORK BLOCKS in your calendar. Everyone needs time to do work. Block it or lose it. You need at least 4–12 hrs/week.

Other than the internal Development Meeting, Monday is a full WORK BLOCK day for me. I know some people, like the talented Jen Couldrey of the Upside Foundation (Canada’s version of Pledge 1%) who grind out the bulk of their work on Friday. Just pick your day and block it.

You don’t have to do all of your work blocks alone. We will do silent work blocks together on Google Meet. In fact, my assistant and I will spend 2 whole days each week in quiet work blocks together. Doing this reduces loneliness and increases camaraderie.

Sometimes it’s 2 full days in a row or one full day (usually Monday) and then 2 half days throughout the week. These aren’t meetings because we aren’t talking through an item.

We are working together again as if we were in the same office. We are all on video, on mute, working together. We come off mute to ask quick Qs.

It’s best with multiple monitors so you can keep faces on 1 screen and work on the other. Shopify is doing a great job of supporting staff to get their home offices set-up.

Here’s roughly how my calendar works each week

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Another actual screenshot of my calendar with all my weekly recurring holds for WORK BLOCKS and Sales etc.

Am I perfect at this every week? No.

There are times when I schedule to do a particular task during a WORK BLOCK and then I move it over and over again for 2–3 weeks. It happens. Be kind to yourself.

📖 Guidelines

A few more quick tips coming soon!

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3. Tools We Use

The tools themselves are irrelevant. How you use them is everything.

Here’s a tool-agnostic version:

  • ✉️ Email — external communication
  • 💻 Messaging — internal communication
  • Time Tracking — time management
  • 📰Project Management — sharing to dos between teammates & individual time management
  • 🗃️ File Storing/Sharing — all files live here

(Upon reflection you could probably consolidate messaging and project management and file storing into Basecamp. This continues to speak to: how you use the tools being more important than what tools you use).

Our specific tools:

  • ✉️ Gmail — external communication _____@skritswap.com
  • 💻 Slack — internal communication
  • Harvest — time management (key for tax credits offered in Canada like SR&ED and other funding programs like IRAP)
  • 📰 Trello — sharing to dos between teammates & individual time management

Everything in Trello has a deadline. This is helpful because as soon as you know you won’t meet a deadline — whether it’s in 2 weeks, 2 days, or 2 hours — you immediately update the card and the team can see that it is moving/changing. If you have a card without a deadline it goes in the parking lot.

When we work through our Development Meetings we work right in Trello, which always keeps it up to date and helps clearly define tasks.

  • 🗃️ Sync — all files live here. I give team members access to some shared folders including: development, research, brand, fonts, logo, and other relevant folders for each role. Everyone has their own folder that I, as the Founder & CEO, have access to. Their own folder is where drafts or misc. items live before they are filed in the proper development or communications or clients folder.

The file system matches Harvest time tracking projects & tasks so it’s easier to maintain nomenclature and structure/systems. Our system is a bit old school: there’s no multiple people editing docs at once or comments you can see without opening the file. I chose Sync because it’s Canadian and allegedly more secure than traditional file sharing vendors. I’ve used almost everything on the market and am happy with Sync.

Some of Slack

Slack is very powerful. You can read other blog posts to figure out how to use it best. I know we haven’t fully optimized it yet. I am sharing some of our key channels that we use for accountability.

Accountability and trust are the lifeblood of remote work. Trust is the human component of accountability.

Slack has commands: “/action” where you can get the machine to do something for you. You could remind yourself about a message or to do something later.

Slack has integrations too, where you can record voice memos, link to other tools, etc.

Slack has #channels: where you can chat with a group of people about a specific topic.

Slack allows you to message people directly: “@person”. We try to keep all of our communications here. In 2 years, I have only texted people’s personal phones after hours no more than a dozen times. This is usually where we will say to each other “let’s jump in” and move to a quick Google Meet because it is faster than typing to each other.

/Actions

/remind will change your life. It makes performing certain simple tasks so much easier.

We have recurring reminders for our Team Huddles in group channels so it pops up with the Google Meet link right before the meeting.

I also have the team set-up individual reminders for their reporting on Monday in the #TeamHuddle channel and in their private chats one-on-one with me on Thursdays before Feedback Fridays.

/record is fantastic — I love to talk things out. I make the most sense when I’m speaking vs writing; but that’s really hard for folks to remember. Enter: the voice memo. More on this below.

#Channels

#office — community — we do have an office and will post when we are going there to overlap/coordinate schedules

#Harvest — accountability — This is where we post our time tracking every day. We all post a screen shot, not because I care how many hours someone worked, but so that we are ALL accountable to each other to keep our time sheets up to date. We each need to see each other post our timesheet each day. RE: leading by example, the team absolutely drops off on doing this when I miss a day or two. Extra accountability for me!

#TeamHuddle — accountability — key! This is where we post our blockers, highlights, lowlights, completed, and working on next every Monday before our Team Huddle Tues meeting. It’s a great way to keep accountable.

#humansofskr — community — HUGE!!!! This is probably the MOST important thing for team building — it’s the water cooler chat or coffee convo that we don’t have as a remote team. We post pictures out and about for the weekend. Pets. Family. Things we’re excited about. We have some pretty artistic folks who also post their creations, which are AMAZING!

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Posts from our #humansofskr Slack channel where we engage with each other as human beings.

Fav Tool

Our favourite tool dates back to 1876: the phone. ☎️

CALL EACH OTHER!! When you have overlapping work hours between time zones — don’t slack, just call.

If they can answer, they will. If they are busy, they won’t. Then you can slack and wait.

No amount of infinite slack messages can replace a phone call.

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SOPs: write it down & repeat it 5x

Standard Operating Procedures (SOPs) are helpful to any business. They can seem cumbersome, but they are critically important.

If you don’t write something down, how will anyone else know how to do that thing? Perform that function/task? If you materialize your processes in writing early then you will onboard easier, delegate easier, and unify knowledge across your team.

There’s also research to show that you remember better when you write things down.

We automate our SOPs through Obie.ai — another great Canadian product. With Obie you can ask a Q in Slack and it will answer it right there. Questions like:

  • Where is the office?
  • What time is the Team Huddle?
  • How do you onboard someone?
  • How do I prepare for the OKRs planning meeting?
  • What does Melissa like calendar invitations to include?
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Tweet from a Sara Mauskopf, who is a female founder I admire.

But what if you’re more of a talker than a writer? I am.

Yet my team has asked me to put more in writing over time. I try to quickly write a few key points in Slack. Then, I use /record to share a voice memo with greater detail that is easier for me but still meets their written requirements.

This is especially critical with regards to product. Even better, we don’t write slack messages for product fixes or updates. I create a trello card with all the details, deadlines, labels, etc. and when I share the link to that card with the team in the #dev channel then I include the voice memo with /record for more info.

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Voice Memos are your secret weapon since the early 1900s.

They make it faster and easier for everyone with more nuance.

Voice memos are best when paired with written instructions.


4. OKRs: Objectives & Key Results

I can’t take full credit for this section. Emily Key taught me about Objectives and Key Results (OKRs). She’s the reason my team read the book below. We are very lucky to have Emily on our Advisory Board sharing her operational wisdom. I am blessed that Michael Dingle introduced us.

We’ve all heard: “what gets measured gets managed” as attributed to Peter Drucker, one of the most influential business management teachers and authors. Since we implemented OKRs in July 2019 we have seen significant performance improvements and toward the right goals.

I’ve found the best cadence is measuring on a weekly and quarterly basis.

What are OKRS?

Objective and Key Results (OKRs). OKRs help you focus. Buy a couple copies of: Radical Focus by Christina Wodtke. Have your whole team read it. Your read it too, of course. Debrief the book together.

Every new hire should read it as a part of onboarding and debrief it with their manager and core team.

Refer to it when you make your new OKRs every quarter. I still refer to pages: 5, 6, 7, 8, 9, 76, 77, 80, 81, 88, 89, 110, 111, 112, 113 of Radical Focus every time we plan our OKRs each quarter. I send pictures to the team as reminders too.

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When do we plan OKRs?

3 weeks before your new quarter plan your new OKRs. 2–3 days before your OKR quarter ends, review your actual performance against the next set of OKRs that you designed a couple weeks prior.

How to plan your OKRs:

Have everyone come to the OKR planning meeting with their ideas of what is mission critical. Everyone brings 1 company objective. For their team or specific area of domain expertise, have them come up with 1–3 key results too.

In start-ups the mission critical focus and activities are easy for the entire team to see. Having your Team Huddle Thurs reinforces and shares information with everyone. The key question for a start-up is simply: what activity will keep the company in business for another quarter?

When the planning meeting starts, everyone posts in Slack and we review them in order. As the manager, you post and speak last.

This method makes our company goals a group activity that bubbles up from the grassroots.

It has also been super helpful in preventing me from dictating what we need to do. I only help recalibrate or tweak with extra knowledge or repeating information. Typically, everyone knows what we need to do and each team member is spot on with that they bring every quarter.

Key Elements of OKRs:

3 simple parts:

  1. set inspiring & measurable goals
  2. make sure you and your team are always making progress toward that desired end state
  3. set a cadence that makes sure the group both remembers what they are trying to accomplish and holds each other accountable. (pages 5 & 6)

“KRs should be difficult, not impossible. OKRs are always stretch goals.” (page 112) On our first few rounds of OKRs we fully meet 30% of the KRs we set. On the remaining 70% of KRs we did not meet, our numbers were halfway to the goal number for each KR. While it may not sound good, it’s corrected based on the aggressive framework. Using OKRs this way, we are able to 3x some metrics in 1–2 months. Which is great, even if it’s only 50% of your original KR goal.

Key Results should focus on:

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Page 76 & 77 from Radical Focus.
  • Growth
  • Engagement
  • Revenue
  • Performance
  • Quality

Measurable/Quantifiable — “more sales” is not a KR. $250k or $2M or $20MM by a specific date are KRs.

Time Bound — As I mentioned before, I find the best cadence weekly and quarterly. But sometimes if we have big external forces on the horizon, we will measure weekly for a focussed 2 months.

Truthfully, we only use Health Metrics the way the book says to sometimes.

Linking OKRs to Meetings

Do you see how the OKRs roll into our weekly Team Huddle updates on Tuesday? Where we share with the team what we are working?

Our OKRs show up in all of the other structures we’ve put in place. That’s what makes this step-by-step guide so useful.

I can’t tell you how many times we will be in a Development Meeting making a decision on what goes into the sprint, when someone says “ya but that doesn’t really serve our OKRs for this quarter, whereas this other thing does”. Fantastic! I love when we all work together to stay on track. No need to be distracted by shiny things.

TIME TRACK DAILY

Anything you want your team to do, you must also do. Lead by example in every way.

This goes for time tracking too.

Want to know how you’re doing toward your weekly and quarterly goals? Track what you do daily. Retrospective reporting bias is a real thing. Track your time, all day, every day.

As mentioned in our tools section, track through Harvest. I like the ZEI because I’m a very tactile person. I flip the physical device and it tracks my time, quick effortlessly. It syncs to Harvest too.

The days I time track are significantly more productive than when I don’t time track. And I end up working on the right priorities when I’m time tracking in the moment compared to the days when I backfill from my calendar.


5. In Real Life (IRL) Matters

At the beginning, I promised that you’d love remote work so much, you’ll absolutely abandon 5 days / week in the office. But that doesn’t mean you’ll get rid of being in-person time altogether. Maintaining in real life moments are key.

We are remote first, but half the team lives within a 1.5-hour radius, so they work out of shared office space 1–3 days/week.

Spending the money to bring the whole team together ever quarter, or at least semi-annually, helps maintain team cohesion as well as build trust and psychological safety.

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Paras Jamil teaching the team about linguistics at Team Time in May 2019.

What do we do together IRL?

  • 1 whole week together Mon — Fri
  • Fly/Train in Sundays
  • Fly/Train out Fri after 1:00pm
  • Mon = work day
  • Tues = work day (or work am + Team Teaching Time pm)
  • Wed = facilitated time + Advisory Board Dinner evening
  • Thurs = facilitated am + activity pm
  • Fri = work am + depart pm

· First 2 days (Mon & Tues) and last half day (Fri am) we work together: in-person, shoulder-to-shoulder, to get a vibe for each other as workers.

· On the 2 facilitated days we:

  • Facilitators should use their creative ideas through play, movement, drawing, building, and outdoor adventures etc. to bring out different ideas related to your OKRs or thinking about a company challenge in a new way.
  • As Founder & CEO I work with facilitators in advance to think through our next milestones or key challenges creatively. We make sure that whatever interesting activities they have planned will relate to our work/OKRs or help unlock some new way of thinking/working together. It is an amazing experience when well-planned and relevant.
  • Bring experts in 1 afternoon. I brought in body language expert and leadership coach, Cindy Dachuk. She worked with the team on body language in the context of sharing the company’s elevator pitch (which all early employees need to know how to do well). It was one of our highest rated sessions ever: the team loved it and found it very valuable.
  • We have something we call “Team Teaching Time” that is often on the same afternoon that we bring an expert in. Team Teaching Time is for each team member to share our internal expertise. Each time we come together we rotate 2–3 team members to teach us anything. It can be related to work or not.
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  • 1 daytime fun activity with physical movement (and accessible accomodations) like bowling, ping pong, board games, archery, etc. from 3:00pm-5:00pm to be inclusive of families.
  • 1 evening dinner with the Advisory Board if they are in the area so that they can mix and mingle with the Team; it’s good for both of them to learn from each other.
  • Personal development. Some of the sessions can just be about helping your team grow. Remember this conversation Peter Baeklund imagined:

>> CFO asks CEO: “what happens if we invest in developing our people and they leave?”

>> CEO asks CFO: “what happens if we don’t and they stay?”

· We try to have our Team Time about a month after we hire new people so that it helps with onboarding.

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skritswap Team and Advisory Board at dinner for Team Time in Nov 2018 celebrating winning the Top 20 Most Innovative Companies in Canada.

How do we make IRL Team Time happen?

  • Schedule 2 quarters ahead so people can plan 6–8 months out.
  • If someone needs to bring their family, pay what you can to enable them to bring their family or for childcare back at their home. Be inclusive.
  • Have childcare/include children available on site that week. We’ve had babies join us for our activities at Team Time.
  • Have facilitators so that managers and assistants can participate.
  • Get facilitators to take notes and make reports on what happened etc.
  • Provide meals and eat healthy. Light lunches, like vegan food or salads, can be equally as tasty as Italian or Indian, but won’t zap your energy as much. Copper Branch is one of our favourites.

6. Mindset

Now that you know how to run a remote team, with all the granular details, let’s look at the best underlying mindset 🧠 and beliefs ❤️ that guide teams to work remotely successfully. This is for you whether you manage 1 person or 100.

1. Anything you want your team to do, you must also do. Lead by example in every way. Lead with accountability, work ethic, taking breaks/vacation, etc. “The way you are is how your team will be” — I have to thank my Executive Coach Hans Phillips of Ontoco for that line.

2. Remote work empowers families, facilitates a diverse team, and helps women overcome barriers. We have 2 young families and a grandparent on our team who all value flexibility. These team members often overperform without overworking. Which is a key difference to know and appreciate.

3. Mindset really matters as a manager. I see myself as the defender of my team. It is up to me to:

i. maintain internal cohesion,

ii. minimize internal friction,

iii. and to protect the team from any negative outside influences.

When you believe you are the defender of your team, it is up to you as the manager to protect their time from distractions or “busywork” that doesn’t align with your mission critical OKRs.

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As the Founder & CEO, I am the defender of my team.

When you believe you are the defender of your team you will ask what processes and structures they need to produce their best work. Then, once you know, you will move mountains to make that work environment possible.

How our Values match our Mindset for Remote Work

I will briefly touch on our values here. I pulled together our first 4 team members in Nov 2018 to co-create our values because we all know, if you aren’t intentional about your culture, it just happens. And usually, it “just happens” in a bad way. I have yet to hear of a serendipitous culture that was just great!

Together we created the values:

  • Considerate
  • Communicative
  • Sustainable
  • Impactful
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Considerate is all about being someone your teammates can trust. Doing what you say you will, by when you say you will. Being dependable. Someone your team can rely on.

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Communicative is KEY for us because we chose to be a remote first team from the beginning. For us, if we feel like we are over-communicating then we are communicating just enough. As the Founder & CEO, I make sure that I repeat core concepts and direction alignment 5x before I consider it truly communicated (i.e. in our Team Huddle Thurs “compass calibration”).

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Sustainable is about sustaining our people — beyond the environmental use of the term. Start-ups are actually a marathon, not a sprint. How are we working in a way that is sustainable long-term? How are we setting OKRs and external expectations that allow us to work sustainably?

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Impactful the whole company’s mission is to make worldwide impact on billions of people. You learn more about that vision here.

You don’t need to share our values to learn from our processes. Our values ground our actions to core beliefs that facilitate remote work well.

To live our values, you will frequently hear us say things like:

“To be in alignment with our value of being considerate, I completed that task for you 2 days early.”

Or things like: “You’ll notice my list in my Team Huddle post is quite long again this week. As I reflect on being sustainable, this means I’ll need to lighten my load next week.”

We also have also lightly oriented our culture around It Doesn’t Have To Be Crazy At Work by the Basecamp Founders Jason David Heinemeier and Jason Fried. It’s hands down the best business book I’ve ever read. It’s up next on the team reading list.

If you’re doing remote work well, you’ll also hit the markers for a top performing team according to Google.

1. Psychological Safety

2. Dependability

3. Structure and Clarity

4. Meaning

5. Impact

Running a remote team will makes it easy to fulfill items 2 and 3. Our unique mission at skritswap and being a small start-up makes it easy to achieve 4 and 5 as well. We achieve 1 through leadership and some of our structures like Feedback Fridays, in particular.


THE END.

Thank you for your attention till the very end.

As you can see, I love being an operator. I am thoughtful about it and work with my team to find what works for all of us. It’s been a pleasure to compile and share this with you.

I know this guide will help you love being an operator too, and make you a more effective leader. It will also empower your team to work remotely; whether for the next month or two, or forever!

And remember:

The winning recipe for remote work is a huge helping of autonomy, a dash of accountability, a generous helping of structure, a pinch of flexibility, and a spoonful of trust.

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