Holidays Around the Corner? Boost Your Remote Team’s Morale With 27+ Expert Suggestions (Tried & Tested)28th Nov 2022 –
When given the chance, almost everyone jumps at the opportunity to embrace some form of remote work. On average, 87% of workers work 3 days a week from home.
Buffer’s research even found that not only do 97% of employees want to continue working remotely but would also recommend it to others.
But conversations about remote work may be singularly focused on the “work” aspect of it and not the unique modifier of “remote.” Studies about how remote work doesn’t affect productivity are all the rage but discourse about how important it is to create a remote working culture needs to gain more steam.
With a skewed emphasis on work output, you can end up with disengaged employees who feel cut off from their team and alienated from company values. From GTM execution to thousands of business decisions taken every day, these core values form the backbone of all operations and processes.
For companies that only went remote during the pandemic, this is a legitimate concern, especially with the holiday season around the corner. The seismic shifts we’ve seen in the workplace induced by the pandemic have brought about a flurry of changes that most organizations are ill-prepared for.
This is where you can profit off learnings from remote companies who’ve been there, done that for a long time now.
Holiday season, as luck would have it, is also often the busiest time for companies, in terms of business, profitability, and growth.
While employees shuffle between meeting deadlines and planning family gatherings for Thanksgiving and Christmas, managers struggle to keep them motivated. Plus, research shows productivity levels drop between mid-December and New Years.Ananya Mahapatra, Consultant Specialist in the Department of Psychiatry, Baba Saheb Ambedkar Hospital & Medical College
At Convert, we’ve always been remote-first and believe that organizations bear the majority of the responsibility to induce a feeling of camaraderie given the turbulent times and recession-mongering cries on the horizon. Integrate a positive culture in remote work settings with these 27 tried and tested practical suggestions.
Understand What Connection Looks Like In a Remote Team
Matthijs Keij, CEO at WithLocals for Business, shared in a webinar with Running Remote that while an office or a co-working space has its value, you don’t actually need an office to do work.
This sentiment was also echoed in Spotify’s Work From Anywhere announcement:
“Work isn’t somewhere you go, it’s something you do.”
Borrowing from the 6 components of company culture from HBR – Vision, Values, Practices, People, Narrative, and Place – Matthijs explained why People, Place and Practices are the main challenges of working remotely.
- Place – The in-office spontaneous chats or socializing at the watercooler can be hard to recreate in a remote setting but it’s important to find ways to help forge those connections.
For instance, you could use Donut to pair employees at random so they can meet and learn about each other. Or have an open Zoom call that anyone can hop on to when they want to socialize.
- People – Remote employees feel isolated, have more anxiety and stress, and are emotionally exhausted. At WithLocals for Business, Matthijs focuses on building meaningful connections to improve the overall well-being of employees. Companies are bringing online workshops, experiences and events to their employees in an effort to help connect people.
- Practices – Matthijs explained a lot of companies put their practices like diversity and exclusion on hold. In fact, it’s more important than ever to keep these values intact. For instance, you can create affinity groups on Slack and share DEI updates with the entire company periodically.
Watch the whole webinar here!
If You’re New to Remote, Bring Your Existing Team Culture to the Virtual Setting
We made the choice to be remote but many others didn’t.Matt Davey, COO at 1Password
In Matt’s webinar with Running Remote, he stressed that “being remote” shouldn’t become your company’s culture. It is just a lens through which you look at culture.
Matt offers 3 suggestions to bring your existing culture and apply it to a remote setting:
- Look at what your team talks about and recreate it virtually – Create small communities on Slack so employees can discuss shared interests like music, books, pets, or gardening.
- Reaffirm the inside jokes and make them inclusive – Inside jokes or memes can help bond a company.
- Document everything – It’s imperative for a remote company to have internal documentation for all your company’s rituals and processes so new hires can look them up.
Check out the webinar here.
Then Create a Repeatable Process to Energize Your Remote Team
The goal is not to recreate the office.Ryan Chartrand, CEO at X-Team
Ryan shared his top tips for energizing remote teams with Running Remote:
- Help employees do more of what they love – Support employees with resources and motivation so they can do what drives them outside of work. X-Team does this by encouraging team members to play games, purchase gym memberships, get a co-working pass, buy courses and books, and discover new restaurants to dine in.
- Find who needs to be energized and guarantee value -Not everyone working from home needs the same level of stimulation. Identify employees who do and conduct virtual social events. For instance, X-Team conducts a 24-hour steps competition where the winning team can win prizes.
- Make virtual happy hours predictable and consistent – Don’t just jump on a Zoom call. Plan happy hours consistently so more people join in. X-Team puts on a show, or lets employees play an arcade game.
Watch the full session here!
27+ Practical (and Doable) Suggestions to Spread Cheer in a Remote Team During Festive Season
The impetus to build a remote team that can take the mental buffeting of the holiday season needs to be top down. Having a Chief Culture Officer may be practical but a single person can’t drive lasting change especially when topics inevitably veer into uncomfortable territory like mental health.
Convert’s CEO Dennis van der Heijden has always led the charge from the front:
Bringing topics to the table and normalizing them is important for me. I share publicly that I’m going to therapy or couples therapy. I often share podcasts and articles that I think will help me better my relationship with my wife. Podcasts like “The Dads Edge” are shared often on Slack. Mental health and well-being like diets, fasting, sports all pass by and are shared often. As a leader, I feel an obligation to overshare to set an example.
Stephan Baldwin, Founder, Assisted Living Centerconcurs:
The holiday season brings along unpleasant memories and emotions for some people. Not to mention the weather and low temperatures are gloomy on their own.
It’s not uncommon for some employees to be affected by seasonal affective disorder (SAD) or depressed during November to late January.
Poor mental and emotional health adversely impact productivity. While clinically happier employees generate higher quality output within their roles, employees struck by seasonal blues tend to slack off and have lower workload tolerance.
This is where employee coworking sessions come in: huddle together regularly so people can hold each other accountable. Joining a virtual meeting room with other colleagues can motivate employees because they feel like they have a community to support them along the way.
Employees need more than the obligatory message from the CEO thanking the team for their hard work and a bunch of OOO notifications. They need to feel connected, cared for, and know they can bring their full selves to work.
Now that you’ve got the tools to set up the foundation for your team’s engagement, let’s draw inspiration from remote brands’ playbooks on making a diverse and remote team work.
Crucial: Take Care of the Mundane
Organization is still key when winding down for holidays. While spontaneous socializing is encouraged, some scheduled fun can go a long way. But don’t forget about getting work done. You want to set reasonable yet concrete project deadlines.
Something Volodymyr Shchegel, VP of Engineering, Clario, is all too familiar with:
This may sound like something Scrooge would do but to keep a remote team engaged over the holidays I find it best to really lay down hard deadlines leading up to time off.
While they also have fun holiday activities planned, Clario found that people prefer finishing off work so they can focus on family. This makes sense considering remote workers can set their hours instead of being stuck in an office and clock mandatory hours.
And Volodymyr isn’t alone in adopting this idea.
Jonathan Zacharias, Founder, GR0, takes a unique approach to keep his remote team motivated — winning their competitors’ business.
Taking advantage of other people who slack off during the holidays helps keep me and my remote team motivated. If our competitors are taking it easy, then that provides us the opportunity to win their business.
Jonathan stresses that the holiday season is all about family and with a little scheduling magic, remote employees can excel both at work and at home.
Gates Little, President/CEO, altLINE Sobanco, shares a fine example of how to get this delicate balance right.
Having planned weekly activities centered on teambuilding and holiday themes keeps everyone engaged when the excitement and busyness of the season is understandably distracting.
Secret Santas, watching a classic holiday episode of a show together, or having a couple hours aside to share our holiday traditions helps ease the workload while bringing us together as a team.
Quick tip courtesy of Mikaila Read, Remote Experience Manager at Mezmo (from the Running Remote community):
“Elfster is a great way to set up Secret Santa (or Secret Snowflake, as I prefer to call it) — gift exchange that is low effort and fun for remote teams.”
Another key organization tip comes from Alex Mastin, CEO and Founder, Home Grounds:
People want to know how they will be spending their holidays, and when they’ll see their loved ones and family members. Being as organized as possible and making this a system where people can discuss and request their time off can show the company is actively considering how to make it work.
Alex shares that coming up with a ‘holiday roster’ towards the end of October helps everyone stay on the same page and feel heard. This is especially crucial for small remote teams where all holiday time off requests cannot be approved.
Gamify the Holidays
Gamifying work and employee engagement builds team morale, keeps people engaged and relieves stress.
So what does that look like in practice?
Demi Yilmaz, Co-Founder, Colonist.io has the answer:
As a business that creates games, it’s safe to say that our love for all things gaming pushed us to rethink our employee engagement practices and how we could use games to make things a little more interesting.
For example, you could create a leaderboard that tracks various metrics such as who responds quickest to customer inquiries or who generates the most sales leads. Each week, announce the winners on a team call or in an email and offer prizes like gift cards or extra vacation days.
Sucharith Menon, Head, People & Culture at LeadIQ, is also no stranger to this idea:
At LeadIQ, we start with an engagement event. This year, we are running an online game show (LunaPark).
Jonathan Duarte, Founder, CEO, GoHire, Inc has had a similar experience with gamified experiences at work:
Having led remote teams for over 20 years, the most successful holiday meetings I’ve experienced are gamified, on zoom, with video, and have nothing to do with work.
Engagement is critical for teamwork. But building a high-functioning team, instead of a group of individuals, requires relatedness.
We’ve done meetings where everyone gets turns on their video on Zoom, shares stories about themselves, their family, their pets, hobbies, or sports. We’ve found team members that went to the same high school but now live in different countries reconnect. Or, team members who have similar passions, or hobbies find a community.
Another great example of gamification? Holiday-themed quizzes.
We hold a small holiday season-themed quiz each day. Each morning we send out an email to all the team members with 5-6 questions to be answered and the team has until the close of business to submit their responses.
On Monday morning along with the questions, we send a list of the winners of the previous week’s quizzes. Each daily winner receives a small value gift voucher to be used at an online store, the scores are accumulated through the week, and the weekly winner gets a larger value gift certificate.
As a finale, on the last day before we break for the holiday, a prize is awarded to the person with the highest score over the month, but everyone who has taken part gets something.Colin Toh, CEO, Headphonesty
Alexandrina Danifeld, Talent Acquisition and Talent Management Lead at Liv.ithas a truly epic idea you can poach: Ginger bread wars.
Someone on my team had the epic idea of organising “ginger bread” wars as an online team activity. The winner is … (you guessed it) the person that made the most creative ginger bread house.
At TurtleOS, more play is encouraged over the holiday months.
Vlad Lokshin, CEO & Co-Founder at TurtleOS, gives a glimpse into how this all goes down:
Last year, we played Among Us, a game of teamwork and betrayal and talked about anything but work. We learned so much about each other in ways that were never possible in normal “work”. We’re looking for something similar this year!
We bought some team members Oculus Quests last year. It was fun, but it’s a bit of a pain to get everyone together with headsets and ample space for VR games.
Also, we’re the 2nd year into running a creative workshop through a company called 28muses. Last year was a music “drawing” class, this year we just did a workshop on Chinese character calligraphy — first learning some history then inventing our own characters. It was so fun to guess who drew each character.
Quick & easy tip: Host a “Slack avatar” contest like Mikaila Read did. Invite people to showcase their festivity and love of the holidays and skip the rules, or prizes — just focus on the fun.
Here’s a sneak peek at what that looks like in practice:
Focus on the Holiday Spirit
While holidays can be a joyous occasion, it’s very easy to get caught up with everything going on in the world. Between family obligations and staying positive in the current environment, it can feel like learning to walk the tightrope.
Rika, co-founder at Kosmo understands this and shares how Kosmo is handling this dilemma:
We’re sending out personalized holiday cards to team members to show our appreciation and to encourage them to take time off to be with loved ones.
We’re also offering flexible working hours to make traveling to family easier. To bring everyone together, we’re hosting a holiday-themed virtual happy hour where team members are encouraged to share their favorite holiday recipes, drinks and traditions.
Maja Kowalska, Community Manager, Zety, believes instead of trying to force people to push through the lack of motivation, we should embrace the holiday season.
A great way to do that is adding festive elements to the usual online meetings. It can be as simple as suggesting setting a cheerful winter or Christmas-themed background on the Zoom call, or wearing a red Santa’s hat. The key here is not forcing it, but rather leading by example. When employees notice your positive attitude and fun antics, they’re more likely to join in and add their own festive twist. While this may seem silly, it is a surefire way to get some energy back in the tank and feel motivated to work.
It’s important to remember that a remote gathering isn’t the same as an office party in the real world setting. Largely, the visual cues are missing. So it’s crucial to circumvent any unintentional awkwardness and improve engagement.
Rudy Rees, an expert at delivering participation in workshops has a pro tip to achieve this:
Organizers often seem to forget that not everybody loves speaking in front of a group of others. Indeed, a New York Times survey placed death third in the list of people’s biggest fears – the top two responses were walking into a room full of strangers and speaking in public. Yet online parties routinely kick off with cringeworthy “ice breakers” and/or introductions where everyone has to speak to the whole group. Don’t do that!
In contrast, when arriving at an in-person party we begin by observing others, being welcomed as an individual, and perhaps by saying “hello” to a small group of one or two people. Kitchen conversations are often where the real fun starts.
So, design your online gatherings with plenty of space to move, where people can drift between small-group conversations. You can set this up in Zoom or use a purpose-built tool like SpatialChat.
Curious to learn how other companies celebrate the winter holidays? Kasia Triantafelo, Head of Community at Running Remote shared a great resource you can check out on Notion.
Opt for Low-Key Activities
Limited bandwidths during the holiday season means not everyone wants to be on a 3-hour Zoom call even if it is a fun activity. Akin to asynchronous work, some companies opt for unstructured social time where people can participate when they want.
Michael Alexis, CEO, TeamBuilding shares a few more examples of low-key team building exercises:
For example, a leader might post check-in questions or holiday-themed icebreaker prompts on a Slack channel, or ask teammates to share pictures of their pets dressed in their holiday best or their desks decked out for the holidays. Perhaps a team member asks the channel their favorite Christmas carols and makes a team playlist.
Zoom meetings are only reserved for movies, games or coloring sessions where people can unwind instead of having to actively engage in an activity. Planning low-maintenance activities prevents teammates from getting needlessly stressed.
David Watkins, EthOS, holds the same belief and shares how the team communicates via Slack:
We share holiday pictures, family traditions, recipes, and holiday activities in a special slack channel. It allows us to see what’s going on in our coworkers’ lives and learn more about their significant others, kids, and other holiday rituals that differ between employees.
We also hold a virtual secret Santa gift exchange, where we pick names from a hat, and each person mails a gift to another employee. We then open them together via a slack call and post pictures of the exchange in the holiday channel.
Finally, we watch a classic movie like Home Alone, It’s a Wonderful Life or Miracle on 34th Street while snacking on popcorn.
Quick tip courtesy of Kaylie Boogaerts, Director of People at Checkly, via RunningRemote’s Slack:
If you’re not keen on paying for a platform to host Secret Santa or Secret Elf like Kaylie calls it, here’s a simple idea. Use a Google form and let people opt-in to Secret Elf and drop some hints about what they like.
Step Outside the Comfort Zone
Low-key activities have their place but depending on your team members’ temperament, you can encourage them to step outside their comfort zone in fun and seasonally appropriate ways.
John Ross, CEO, Test Prep Insight, shares an awesome idea that you might want to steal:
I was trying to come up with ways to keep the team engaged as we headed into the Christmas season, and I came up with a remote murder mystery.
We did a Santa Murder Mystery last year, and it was awesome. The team absolutely loved it. It works like a normal murder mystery party (if you’ve partaken in one), except it was remote. I secretly tagged one of our employees as the killer, and it was up to everyone else to figure out who “killed Santa.” Every day for two weeks, from December 10th until Christmas Eve, I released one clue, which was intended to be cryptic and thought provoking.
On Christmas Eve, everyone emailed me their guess as to who it was, and whoever got it right got a $300 Starbucks gift card. Though a small part of everyday operations, it kept everyone checked in during an otherwise “check out” time of year. People were sending around messages on Slack and getting a laugh out of it. I plan to do it again this year.
Ugly sweater parties have been a holiday staple. Leanna Serras, Chief Customer Officer, FragranceX took that idea and adapted it for a remote setting:
Our annual ugly holiday sweater championship is a bit of seasonal fun that also helps our team members bond so we can enter the new year as a stronger and more cohesive unit. The rules are simple. Everyone has to wear their ugliest holiday sweater, and we shine the spotlight on each member in turn for the appreciation of the rest of the team. Then we all vote for the winner who gets a bottle of fragrance for their prize. It’s loads of fun and there’s always lots of laughs all round.
Bring Team Members Closer. Always a Hit!
While the entire point of spreading holiday cheer is to bring teams closer, it can feel like an abstract idea.
Fortunately, we’ve got some tangible ideas you can emulate.
Victoria Harrison, Chief Engagement Officer, Convert, shares how you can get started and how Converters get into the holiday spirit:
Being part of a remote team gives you the opportunity to learn from other people who may not live in the same city, or even the same country as you. And this is especially true during the holidays.
Choosing a theme and asking your team to share their thoughts on it can be a great way to spark conversation and celebrate. Food, music and local traditions are great topics for video and photo sharing.
It can even be as simple as sharing a little bit about you that your colleagues might not know.
At Convert, we made short videos with little bits about our lives as a way of celebrating during the holidays.
Holiday gift exchanges also work well. For example, send a holiday food item to a colleague in another country you’re randomly allocated. Follow it up with a tasting session where you come together to try the foods in a video call.
Want to do something more fun? Mikaila Read, Remote Experience Manager at Mezmo, did something last year you can try.
I started “Holiday Hot-Takes” which consisted of silly conversation starters and polls delivered to our #community channel to promote fun and cheer.
I also used Polly and invited people to add their own options as answers, some questions included:
- “No end of year is complete without…” (Die Hard, Family Time, Charity, Eating Gelt…)
- “What’s your holiday drink of choice?” (Eggnog, Hot Cocoa, Mulled Wine, Salep…)
- “Share the soundtrack of your holiday! Thread those tunes.”
Nunzio Ross, Owner and Head Director, Majesty Coffee shares an effective engagement strategy to bring everyone together:
We encourage our remote workers to give us a tour of their in-season decorations every year. It’s an exciting time for everyone at work, especially our remote team, to get into the festive spirit in their home offices. Everyone is more than happy to exchange greetings and share their holiday experience with a cup of hot cocoa on the side.
Marina Vaamonde, Real Estate Investor & Founder, HouseCashin goes all in with Secret Santa:
Everyone loves receiving mail, especially as a gift from a thoughtful co-worker! The trick to making this fun rather than yet another holiday obligation is giving your team plenty of notice. With ample time to prepare, teammates can find out about their recipient’s interests, plan, buy or create, and mail their gifts well ahead of your set mailing deadline. Then, ask employees to wait to open their gifts until the big holiday reveal – a big unwrapping party over Zoom!
Be Generous With Incentives
You can’t go wrong with rewarding people for their work, especially during the holiday season. That could mean year-end bonuses, more paid time off, or a cash gift.
Maciek Kubiak, Head of People at PhotoAiD, shares how it’s done:
On top of end-of-the-year bonuses, we are organizing a secret Santa party over Zoom for our remote teams. We asked everyone to submit their wishlist a few weeks ago and our team has been working hard to match everyone up. Each person will have $50 to spend on their assigned secret Santa.
We’re also giving out prizes for the best dressed, or the best decorated Zoom background during our scheduled hang.
Abe Breuer, CEO, VIP To Go, stresses how important it is to incentivize teams like customer service that have to work less-than-desirable hours during the holiday season.
We give cash bonuses at a flat rate. We become extra generous during these times, considering that employees must focus and work hard while everyone around them is in a holiday mood.
Holger Sindbaek, Founder & CEO, Online Solitaire offers an earlier start date for vacation for added motivation:
I’ve found that people work much more effectively when you give them something to work towards. So at the end of November, I write a list of things that I’d like my remote team to accomplish before the holidays. If they achieve them before time, they start their holidays two days beforehand.
Give Back To The Community!
Since the holiday spirit is all about giving back and spreading joy and kindness, companies use this time to donate to charities chosen by employees or raise awareness for social cause team members care about.
Victoria Harrison, Chief Engagement Officer, Convert shares how Convertors accomplish this:
We randomly assign people in the team and make a fixed donation to that person’s charity of choice. It is interesting to learn why they chose that charity and what makes it important to them.
Arthur Worsley, Founder, The Art Of Living, has proof of how social responsibility improves employee engagement.
Social responsibility initiatives have been shown to improve employee engagement by over 8%, while also bringing down turnover rates.
Each employee gets to pick a cause of their choice in their local community. They can make a short video that highlights this cause and why it matters to them. With their permission, we post these short clips on our Slack workspace, and also on the company website as well as its social media profiles to help raise support for their chosen cause. The company also makes a $120 donation to each of the causes chosen by the employees in their names.”
And while you’re giving back to the community, don’t forget the one right under your nose.
Max Wesman, Chief Operating Officer, GoodHire, knows gifts make remote work a pleasant experience during the holidays.
Anything that makes the remote work experience easier and more seamless will go a long way. Gifts like noise-canceling headphones, a lap desk, or even a Spotify subscription are great examples. They can be used in and out of the workplace, time and time again. In my view, it’s one of the best ways to show your appreciation over the holiday season.
Achievements & Awards Seal the Deal
Michael Scott may have had a point hosting The Dundees every year.
Recognition can make employees feel seen and valued. At the same time, they feel motivated to continue to do their best.
Jonathan Merry, Co-founder & CEO, Crypto Monday, echoes this sentiment:
We’ve been hosting virtual award ceremonies for the past two years now. During these events, managers acknowledge team members’ accomplishments and show their appreciation with company-sponsored awards. This is a great way to motivate employees by making them feel valued for their contributions. Our employees look forward to it each holiday season, and it’s a great way to kick off a new year on a positive note.
At Livit, everyone participates in a year-end celebration. Alexandrina Danifeld shares how this online event works:
We round up all our team members, as well as our partners and most beloved clients (this is the twist). We gather them all in Butter and host a long event during which we present our achievements of the year, have a couple of rounds of “table hopping”, and some games.
Colin Palfrey, Chief Marketing Officer, Crediful, knows how remote teams can feel unappreciated sometimes, especially during busy spells. Here’s his pro tip:
Take some time to talk to each employee individually to thank them for their efforts and congratulate them on all their successes. Then, bring the team together in a video call to discuss all that they have achieved and hand out thank-you gifts. Make certain to leave no one out.
Tying It All Together In Time For The Holidays
Getting through 27+ tips can be overwhelming. So we did some math to see which tips are the most popular and possibly worth your time:
Our last tip comes from Vartika Kashyap, CMO, ProofHub.
(Best TL;DR if you just skimmed through the post!)
- Organize a Get-Together for Employees
One great way for ProofHub to spread the holiday cheer to its remote employees is by having a Halloween or a Christmas party and inviting everyone to gather in a specific location for an enjoyable holiday party. It provides a chance for the remote team to interact personally, get to know one another, and have fun! These kinds of activities improve teamwork and employee morale both on-site and remotely.
- Host Holiday Competitions
We hold enjoyable competitions to celebrate the holidays with the remote team in between work assignments. It might be honoring the employee who completes the most tasks over the week or recognising the team member who is the most festive. They often run entertaining mini-contests where the prizes are free things and basic presents like gift cards.
- Post Interesting Pictures in Chat
The remote team is encouraged to submit images of their celebrations in our company chat tool. Each team takes part in ProofHub, where they post these images and engage in conversation with one another through comments. It’s a fantastic method to keep things interesting and banish festival blahs.
- Plan Team-Building Activities
Team-building activities are a good method for teams to get closer. And our company makes a point of organizing it on a regular schedule. Teams are created within the organization as a part of it, and competitions are held amongst them. Being in a squad with people from all different departments allowed them to get to know one another better and learn how to operate together.
From everyone at Convert, we wish you happy holidays. May your toast never fall buttered side down and your cocoa stay hot.
Oh and in case you’re new to remote work, check out how we made “remote work” work for us. And the Running Remote community for all things remote.