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Leading, Motivating and Adding Fun With Virtual Teams, Remote Employees

Leading Virtual Teams – How to Lead, Engage and Add More Fun When Your Team Isn’t All There (Physically That Is)

One of the most frequent questions I get asked is, “Mike, how do you engage, inspire, and motivate people when they work from home or even in another city and you don’t have the same level of interaction with them as your other onsite employees?”

There’s no question, it’s a challenge engaging people who you rarely see in person when clearly face-to-face conversations trump all other forms of communication. Maintaining a feeling of team camaraderie and unity when the team is scattered across the country or even the world can feel like a hopeless task.

But there’s no getting around the fact that more and more organizations are relying on remote workers. And more and more employees want the flexibility of being able to work from home or stay in their city and not relocate when their office moves shop.

Consider just a few of the trends from Global Workplace Analytics (June, 2017):

A 2015 survey of business leaders at the Global Leadership Summit in London found that 34% said more than half their company’s full-time workforce would be working remotely by 2020;  25% said more than three-quarters would not work in a traditional office by 2020.

And really, why not? Having the option of employees working remotely can save companies considerable costs and prevent them from losing top talent. It allows businesses to hire great people from anywhere on the planet. Many top performers say they want more flexible work options and better work life balance, and part of that mix can include working remotely, at least part time. Several studies also suggest that remote employees are often happier and less stressed. Managing for results and output rather than straight hours worked at the office can end up being a huge boon to productivity. Telecommuting can also be a way to be more environmentally friendly.

Yes, there are some downsides. Telecommuting isn’t for everyone. It can be lonely and isolating.  Employees that aren’t accustomed to working alone can struggle with the lack of supervision. There can be chronic concerns around trust and communication.

But these shortfalls can be overcome. Indeed, they have to be overcome – any smart, successful leader needs to be able to lead virtual teams. It’s no longer considered a “nice to have” option but rather a growing necessity for leading in the 21st century.

100+ Ideas for Leading Remote Employees, Adding More Fun & Humor to Your Virtual Teams

Here are some ideas on how to not only effectively lead a virtual team, but how to engage a remote team and keep the fun and humor alive even when your team isn’t all in one location (and by the way,  you should be doing these with all of your employees):


  1. Set regular office hours when remote employees know they can reach you. And it’s not a bad idea to have every member of your virtual team also commit to certain hours or days when everyone on the team knows they’ll be available for phone calls or virtual meetings.
  2. Schedule one-on-one calls/virtual meetings with each member on a regular basis at a time and schedule agreed upon by both parties. Regular check-in points are crucial when dealing with remote employees and should be considered a non-negotiable time slot blocked off on your schedule!
  3. Be diligent about choosing the right communication vehicle for the right messages. E-mail is great for short, factual information sharing, but be aware, studies show that 50% of all e-mails have a tonal issue: Half the time the recipient of an email isn’t quite sure how to interpret the tone of the incoming email. The most effective form of communication with any remote employee is the telephone or even better, video meeting technology such as Zoom or Skype.
  4. Invest in on-line video training to learn the ins and outs of everything you can do with Skype, Zoom, Google Hangouts, and Slack etc. so you make the best possible use of the technology when holding virtual video meetings or communicating remotely with employees.
  5. Agree upon standard response times from all virtual employees so everyone on your team has realistic expectations about how quickly everyone can expect a response from one another.
  6. Even if you work in different time zones, try your best to schedule at least an hour or two where everyone’s schedule overlaps to facilitate easier scheduling.
  7.  One company in California creates small bobblehead dolls of every virtual team member (you can find several sources online) so that everyone has mini-avatars of each other to remind everyone, in a fun way, of the human faces behind the e-mails and telephone voices.
  8.  A small but important tip: When having difficult or important phone conversations stand up! You’ll breathe easier, have more power in your voice, and be more confident.
  9. It can be even more important with virtual employees to get to know your employees at a personal level: What are their children’s names, ages, and interests? What are their hobbies? What do they like to eat, read and watch? To build trust with remote employees you need to make an extra effort to get to know them.
  10.  Because your touch points may be less frequent with remote employees, commit to regular praise. Remember the power of emailing or phoning someone with a simple thanks without any  other agenda.
  11. Practice the power of surprise by mailing employees something fun at random times: a funny note, a funny thank-you card, a small office toy, or novelty item.
  12. Leave an inspiring or funny voice mail message for employees at the start of each week to help them kick off the week on a positive note.
  13. Send a weekly “Kick Starter” e-mail out to the team as inspiration, including an inspiring quote and one best practice tip.
  14. Have everyone send a short e-mail each Monday morning that highlights their top 3 challenges of the week ahead.
  15. Have everyone send out an e-mail at the end of each week with their top 3 highlights or wins for the week.
  16. When holding live, in-person meetings with the rest of your team at your office, use place settings or empty chairs with avatars to represent the employees that are working remotely and not able to be there in person.
  17. Open virtual video meetings or teleconference calls with your team with a short, fun icebreaker, the way you would with an in-person meeting. Create your own or read on for more of my ideas throughout this list!
  18. Since virtual employees don’t get the usual dose of “water cooler chat,” start virtual meetings ten minutes earlier than the actual formal meeting start time to allow time for personal conversations.
  19. Hold a drinking game during your video meetings where everyone must take an exaggerated sip from their coffee/tea/water every time someone uses the phrase/word/acronym of the day.
  20. Create some regular prizes that you award at the end of each virtual meeting, such as best quip or comeback of the meeting, best use of jargon, or wackiest idea of the meeting.
  21. Assign a “meeting ref” who overseas any meeting “violations” in a fun way.
  22. Rotate the role of the meeting chair: It can be particularly challenging for virtual employees to gain new experiences in workplace roles, so be intentional about looking for opportunities for them to take on new roles and assignments.
  23. Create a clothing color scheme that reflects certain moods or energy levels, so when people log in for the video meeting everyone on the team get an instant read (and hopefully a chuckle) based on the color people are wearing.
  24. Xerox is one of many companies that holds virtual employee holiday, Thanksgiving, and Halloween parties. So why not give it a try? A few wide-angle interactive camera setups and strategically placed screens as a starting point, and you’re good to go!
  25. Some companies hold virtual karaoke parties with great success.
  26. Try a round of virtual charades as an icebreaker or social event.
  27. A remote, virtual version of Pictionary is easy to do – especially if you have an interactive whiteboard.
  28. Have a quick “Everybody draw their best version of _______” and then have everyone show their work after two minutes and vote on the winner or most creative masterpiece.
  29. Hold a “Guess the voice” contest – where managers or employees have to match the voice to the employee.
  30. One office does a virtual version of the “telephone game,” where everyone whispers the start of a bland workplace memo or report, whipsering it along from person to person until the last person repeats back what they heard – usually something ridiculous funny.
  31. For virtual meetings open with an icebreaker where everyone must do a one-minute show and tell presentation with an artifact from their house/remote office that reveals something personal about themselves or their location they are currently working from.
  32. Assign everyone an alter-ego name for the meeting based on this simple formula: You alter-ego name is:  Your First Pet’s Name as a Child  + Your Mother’s Maiden Name = Your New Name.
  33. Same as above, only using everyone’s “Rock Star” name as generated at the website: Rock Star Names
  34. Same as above, only using everyone’s “Country Western” name as generated at the website: Country Star Names
  35. Same as above, but using everyone’s “Pro Wrestling” pseudonym as generated at the website: Wrestling Names
  36. Same as above, but using everyone’s anagram-generated name, as created at the website: Anagrams
  37.  Same as above, but use everyone’s “poet’s name” as generated at the website: Poet Name
  38. Pull out a coin and read the date, then have everyone talk briefly about their top memory of that year and where they were and what they were doing that year.
  39. Open with a short fun video, such as the Fun dancers video on the home page of
  40. Ask everyone an unusual, fun, or thought-provoking work-related question. Starting the meeting with this tradition not only can be fun, it encourages everyone to participate and you can learn some interesting things not only about your colleagues, but about your organization that might help you succeed. For a list of potential questions, you can purchase the e-book “Inspiring Questions for Inspiring Workplaces” at Inspiring Questions E-Book or try the following questions on for size:
  41. What celebrity would help our organization the most and why?
  42. What was the worst job you had, and what specifically made it so bad?
  43. What TV show or movie title best describes your workplace culture?
  44. If you could change one policy or rule in your workplace, what would you change and why?
  45. If you could change your job title to better reflect your role and responsibilities, what would you call yourself?
  46. What’s your most annoying workplace buzzword or jargon phrase?
  47. What’s one thing we could do to make the workplace more fun?
  48. What’s one thing we ought to be doing for our customers that we’re currently not doing?
  49. What’s something we need to do more to foster more ideas in the workplace?
  50. Who’s the most creative person you know and what makes them so creative?
  51. Go around the room and ask everyone to answer an unusual or fun personal question … something that allows participants the chance to get to know each other at a personal level. This needn’t take long; some of the questions may only require very succinct, top-of-mind answers, for example…
  52. What’s the best movie you’ve seen recently?
  53. What’s your favorite TV sitcom of all time?
  54. What’s the worst job you ever had?
  55. What’s the number one place you want to visit in the world?
  56. If you won the lottery tomorrow, what would you do?
  57. If you could play a musical instrument you currently don’t play, what would it be?
  58. What other language would you most like to speak fluently?
  59. What was your very first job?
  60. What is your favorite season?
  61. What would your “last meal” request be?
  62. What’s the funniest thing that has happened to you recently?
  63. What’s the funniest thing someone has said to you recently?
  64. Recognize whatever fun, offbeat theme day or holidays it happens to be, such as “Talk like a Pirate Day” or “Blame Someone Else Day.” You can simply announce the day’s theme at the start of the meeting and/or post it on a whiteboard or flip chart for everyone to see. For a listing of offbeat theme days, Google Fun, wacky theme days.
  65. Recognize someone on the team by sharing and praising a positive piece of news about them.
  66. Share a good news story that has happened in your organization or industry.
  67. Many organizations with a strong safety culture open their meetings with a “safety moment,” so try a spin on this by opening with a “values moment,” where you talk about one of your organization’s core values, relate a story that demonstrates how someone lived the value out loud or go around the room and have everyone talk about something they’ve done recently that reflected that core value.
  68. Share a fun fact related to your business – some weird statistic, strange historical fact, or offbeat piece of trivia.
  69. Share a quote of the day with the team – something funny or thought-provoking, or better still, both! There are hundreds of great sites on the web for quotes, and you also can find great quotes in the archived issues of the Humor at Work e-newsletter at: Humor at Work Archives
  70. Open the meeting with a “Meet ______” segment, where you introduce someone new to your organization complete with some fun, personal facts about the individual.
  71. Stupid human tricks: yes, open with a segment of stupid human tricks wherein you encourage anyone to step forward with any weird skill or talent they possess, be it ventriloquism, touching their tongue to their nose, wiggling their ears or simply arching one eyebrow in dramatic, “Spock-like” fashion. Award a small prize for the best stupid human trick as voted on by the meeting participants.
  72. Read out a rave review customer letter or raving comment by a customer.
  73. Brainstorm something fun or silly to fire up the creative juices, focus people in the present, and to remind participants of the basic rules of a good brainstorming exercise (no blocking, listen to each other, leap frog off each other’s ideas, go for quantity not quality).  Potential topics include:  come up with the most number of uses for a paper clip, create a new superhero that reflects your best business practices,  come up with 10 alternative uses for a stapler, 20 ways to add value to your customer service, or alternative names for your meeting room…
  74. Go around the room and have everyone say how they are doing on a scale of 1-10. Option b, have them not only say their number, but why they chose the number they did.
  75. Have participants share a photo or picture they drew before the meeting that best represents what is on the top of their mind right now.
  76. Have a five-minute trivia challenge game with questions related to your industry or organization. This could easily become a tradition at every meeting.
  77. Have a five-minute trivia game NOT related to your business.
  78. Open with a book review of a work-related book that someone read. This could become a rotating tradition where someone new each meeting is called upon to provide a synopsis and review of a book.
  79. In the News: Share some interesting news articles or opinion pieces from the news that relate to your industry.
  80. Open with the “stress-busting tip” of the day. This could become a tradition along the lines of the “safety moment” but instead focusing in on stress management and overall wellness topics.  The tips could run the gamut from how to get a better night’s sleep to nutrition tips; from how to prioritize your workload effectively to how to tap into your sense of humor.
  81. Open with the joke of the day. Keep it clean, and of course stay away from any sexual, ethnic, religious, or political humor.
  82. Ask everyone or anyone to share the funniest work-related anecdote that has happened to them since the last time you met.
  83. Introduce the special guests attending your meeting in spirit only: To add some fun to your meetings and to help your team brainstorm from some different perspectives, try creating a few stock, exaggerated imaginary characters who attend all your meetings. Make one an imaginary superhero – someone who represents your company values in an outrageously exaggerated way. When you brainstorm or debate a new decision, you then get to ask, “What would Super Dave do?” (Of course, I’m confident you’ll come up with a wittier, more descriptive name than Super Dave.)  Then create a character who represents your most ideal customer, and a character who represents your most powerful nemesis (perhaps your main competitor), after all, every great superhero requires a super villain! Flesh out their attributes, then use the characters as points of reference in all your planning, brainstorming, and communication efforts. Remember, the entire planet is depending on you!
  84. Open each meeting with a Top 10 list. It could be funny or merely interesting facts or tidbits about your industry. A simple one to try is a “Top-10 Reasons We’re Having This Meeting,” then create a list that intertwines the humorous with some serious reminders as to why the meeting is important.
  85. Announce the “Meeting Rules of the Road,” but since the idea is to set a positive tone make sure they are fun! You might consider announcing, for example, some fun penalties for meeting infractions, such as: Whoever is caught texting or answering a cell phone call will have to dance an Irish jig or pay a dollar into the social fund committee.
  86. Announce a “word of the day” for your meeting. Define what the word means, use it in a sentence, and then encourage people to weave it into as many conversations as they can.
  87. Announce the “weasel word” of the day for the meeting: a word or phrase that you are trying NOT to use in your workplace. Fine people a dollar every time they use it in the meeting.
  88. Open the meeting with a wacky sound that becomes your official “start of the meeting kickoff” signal: a gong, kazoo, or bagpipes would all work fabulously. Except for the bagpipes.
  89. Have everyone wear name tags revealing a word that reflects their energy level or mood.
  90. Have each person around the table take a moment to thank someone, as a way of reminding people how important it is to regularly praise employees in your organization. The person doesn’t necessarily have to be present at the meeting, it could be a simple public recognition of someone that serves also as a reminder than after the meeting everyone present at the meeting should take the time to acknowledge the individual in person.
  91. Have everyone stand and do the “fun dance” for one minute. And yes, you can do this virtually. For instructions, watch the video posted here: A Simple Guide to Fun Dancing
  92. Acknowledge any birthdays, anniversary dates, or special occasions happening in any of the meeting participants’ lives.
  93. Open with an interesting “This Day in History” fact (Google “this day in history” to find examples). Bonus points if you find a few that are not only interesting but also relevant to your industry.
  94. Have each participant come up with as many anagrams for their name as possible in one minute.
  95. Have each person stand and spell their name using only the movement of their hips.
  96. Another alter ego name generator, this one for your Benedict Cumberbatch name: Benedict Name Generator
  97. Rather than have everyone wear name tags with their names on them, have everyone wear a tag with a word on it that best describes their work situation since you last met.
  98. Open with the question: What’s one thing you have done since the last meeting of which you are most proud?
  99. Open with the question: What’s the funniest thing someone has asked you since the last meeting.
  100. Name one person who has helped you since the last meeting.
  101. What are you most looking forward to in the coming month?
  102. Open with the question: If you could start your own country, what would it be called, where would it be located, and what’s the first law you would pass?
  103. Open with the question: If our organization/team/business was a t-shirt, here’s what it would say…
  104. Open with the question: If you could be the Big Kahuna for a day in our company, how would you spend the day?
  105. Open with the question: If you were the Big Kahuna for a day, what one rule would you create or eliminate?
  106. Hold a “stand up, sit down” meeting where everyone stands for every other agenda item, as a way to change up the energy and encourage some movement/exercise.
  107. Start with the question: what was the worse job you’ve ever had?
  108. Start with the question: If you had a magic wand, what would you change instantly about your job?
  109. Start by having everyone share one thing everyone would be surprised to learn about them.
  110. Ask everyone what their unique super power is?
  111. Thank everyone for attending the meeting in a fun way

Michael Kerr is a Hall of Fame international business speaker, motivational speaker, and author of six z books, including The Humor Advantage: Why Some Businesses Are Laughing All the  Way to the Bank and Inspiring Workplaces. Michael speaks on inspiring leadership, inspiring workplace cultures, and on how businesses around the world leverage their humor resources for outrageous business results. 

Copyright © 2018, Michael Kerr. All rights reserved.
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