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Staff & Training

How to Keep Your Team Motivated During Uncertain Times

Ryan Chan

Over the past few months, we have seen many companies, including UpKeep, announce that they are transitioning to work from home as the worldwide spread of COVID-19 accelerates. At UpKeep, we have overcome the first hurdles of moving our team completely remote: ensuring everyone has the necessary tools and supplies, defining the new processes, and encouraging best practices for working efficiently at home. But, this is the first step towards creating an effective work environment for remote employees. The next critical question we had to ask ourselves was: how do we motivate our team who now work from home during these uncertain times?

In our webinar, “How to Keep Your Team Motivated During Uncertain Times”, our CEO, Ryan, and Chief of Staff, Caitlyn, share their tips and tricks on this topic. You can watch the full recording here:

Below, we have also recapped this session and provided further reading.


How to Communicate During COVID-19

Send Daily Emails

The first thing we realized is that this crisis called for over communication. 

We have always had an incredibly tight-knit team here at UpKeep and we saw each other every day in the office.

Working all remote was different and we didn’t have the same in-person cadence we had previously.

We wanted to maintain the culture and the community that we all had. So, we brainstormed ways to over communicate to bridge the gap between those small, but incredibly important “hallway conversations” we had in passing.

We decided to send daily emails to the team updating them on wins and progress we’ve all made. This made a huge difference!

Those emails include:

  • General company updates
  • Company wins
  • Specific examples of how we’ve personally helped our customers overcome hardships
  • Employee spotlight
  • Photos of the day that were shared on Slack
  • Our NPS score
  • Self-care tips and valuable messages about the outbreak from our HR Director

And to spin it in a positive light, in many ways, it actually became something that we improved on which ultimately became a big positive for the entire company. Now, instead of those hallways conversations amongst 2 or 3 people, we had it in writing where everyone can stay updated at the same time and we could all share the wins across the entire company.

I think it has actually helped us in the long term to be better at documentation and communication amongst the entire company.

Answer Every Question

From those emails and through Slack, questions started flowing in.

With the team’s help, we’ve addressed every question that have come across our desks. We made answering questions a priority to keep everyone calm, focused and educated.

Keep Positive and Upbeat

Everywhere you turn, the news is negative. We hear about more deaths and the spread getting worse. It’s important to take a break from all the bad news and think about something else. 

We purposefully use a positive tone in every communication we send. On Monday, our CEO’s brother had a baby, and he shared that with the team. 

Our Head of Customer Success, Joe Schmitt, sends an email to his team on Mondays to kick off the week sharing good news about our customers. 

Don’t get us wrong, we aren’t ignoring the crisis. But, we’re trying to remind everyone that we can always find something positive to focus on. 

We’ll reiterate as well – we don’t think that it is business as usual prior to the outbreak. We, as a team, have simply focused on things that are within our control. Our attitude, our effort, and our impact to the community.

Focus on Company Mission

At UpKeep, our goal is to empower maintenance teams to become twice as productive and allow them to receive recognition for the meaningful work they do. 

Our Core Values are:

  • We choose customers over revenue.
  • We choose progress over perfection.
  • We choose grit over prestige.

We chose these core values with direct contrasts, which help guide our team choose between two very good potential options.

Difficult times like today are exactly why our values matter. And with every communication sent, I remind the team of our core values and mission. 

COVID-19 doesn’t change who we are, why the company exists, and what our mission is. The only thing that matters is that we stay focused on our mission and values, and we continue to provide value to our customers to help us achieve our goals.


How to Keep Employees Focused While Working From Home

Ensure Employees Have Everything They Need

First, you’ll want to ensure your employees have everything they need.


The day we sent everyone home to work, we allowed them to take their computers, monitors, headphones, etc. 

Once home, many had hurdles to overcome. We discovered many employees didn’t have great Internet, and calls were dropping or cutting out. We’ve supplied personal hotspots to solve for that.

Others found that the chairs they were sitting in were quite uncomfortable. We encouraged them to go back to the office and grab their comfy office chair. 

We’ve shipped monitors too. Anything our employees need to be successful we’ve provided. We don’t know how long we’re going to be working from home and we want them to be as productive as possible.

Set Expectations

We use Slack at UpKeep which is a messaging app that enables you to bring your team together and create channels for specific topics. On Friday the 13th, our first day WFH as a company, we created a WFH Slack channel and posted the following to set expectations:

How we will work together as a company:

  • Lunch meetings
  • Town halls
  • Happy hours
  • COVID-19 slack channel

How we will work together as a team:

  • Biweekly stand ups
  • Virtual stand ups daily
  • Maintain 1:1 schedule

How we will work together as individuals:

  • Have a designated work space
  • Attend all scheduled meetings
  • Keep teammates in the loop when unreachable
  • Keep calendar visible
  • Over communicate
  • Make sure your contact information is updated

Spelling it out really helped all of our employees understand what was expected of them through this period of working from home. 

Schedule Two Daily Syncs

Our Operations Team keeps things running smoothly by holding two daily syncs. One in the morning and one in the afternoon. 

During the morning sync they discuss tasks the team is working on, and Caitlyn, their manager, asks if they have any blockers and how she can help them overcome those blockers. 

In the afternoon, they all share what they are grateful for and a new tactic they tried that day.

It’s so easy to never stop working when you work from home. There isn’t a specific time to quit. The days and nights can sometimes run together. But, the afternoon sync allows them to transition into the evening and gives them permission to stop working to think about something else. 

Organize Social Impact Task Force

As a team we’re helping our communities navigate the COVID-19 crisis.

To date we’ve:

  • Sent flowers to our retirement home customers thanking the men and women who work there for protecting one of our nation’s most vulnerable populations.
  • Started a job board for maintenance and reliability professionals that have lost their jobs.
  • Created infographics to promote actions people can take to support frontline workers.

Our task force gives our employees the opportunity to help others and think of something besides the bad news they hear about daily. 


How to Maintain Company Culture

Engage Everyday on Slack 

This is a fun one! First off, we encourage everyone to communicate via Slack. Each team has their own channel, and besides work updates, they’re encouraged to post advice as to how they’re successfully working from home. 

Organize Daily Competition

We engage our entire team every day on slack through competition and then award the winner.

Here are some examples:

  • Share a picture of your coffee cup for a chance to win a Starbucks gift card!
  • Share a jam that perfectly encapsulates work from home life for a chance to win!

  • Share the funniest/most creative (safe for work) Zoom Video background for a chance to win a case of LaCroix!

  • Submit a “Sunshine Selfie” AKA a selfie of you out for a walk for a chance to win an Amazon gift card!
  • Share a video of your pet for a chance to win a Petco gift card!

Assign Pen Pals

Every day someone from the Operations Team is encouraged to organize a Zoom lunch and reach out to employees.

We assigned everyone in our company an “Ops Buddy”. And, the Operations Team checks in on their buddies every week to see how they’re holding up. It’s been a great way to get to know someone you’d otherwise never speak to, while playing some fun games and having a nice conversation! 


Those were all of our tips and tricks! We hope you found this helpful in keeping your team motivated during these uncertain times!

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