4 Secrets to Building and Managing Successful Remote Teams [Webinar Recap]

Michael Roberts

Remote working is becoming more popular than ever… 

But it’s challenging to manage remote employees and create cohesive teams.

That’s why Joe Martin, VP of marketing and strategy here at CloudApp hosted a recent webinar that aired in February and featured two experts on remote working and employee management:

John Knightly, the CMO of BlueJeans, a video conferencing SaaS company. 

And Gaetano Di Nardi, director of demand at Nextiva, a business phone system SaaS company.

Joe, John, and Gaetano provide proven strategies and best practices for building high-performing remote teams. 

We’ve taken those insights out of the webinar and reprinted them here. This is part 1 of 2 parts covering the 4 secrets of building and managing successful remote teams. 

Let’s dive in!

1. How to Recreate “Watercooler” Moments Remotely to Maintain Personal (And Professional) Relationships

The Balance of Creating Professional & Personal Relationships


John

One of the things that we've done is kind of recreate that water-cooler effect.

We have a monthly meeting we call a “straight talk.”

There are no powerpoints allowed and it's really not meant to be a business-oriented meeting, it's meant to be fun.

We’ll play a game where we choose what animal represents you best or ask about holiday plans and that sort of thing. 

We found that that's been a great way to just get people talking.

Maybe there's something on their mind about the company or their personal development, and this is an easy atmosphere for people to ask those questions and get to know each other beyond just work.

Gaetano 

We have in-person meetups once a quarter, but sometimes, I have employees who feel isolated. What I tell them is, let's just digitally work and hang out at the same time.

As weird as that sounds, we'll be on a screen share and we may not even be saying anything to each other, we're just typing and working. 

Then someone will make a comment like, “Oh! Did you see the latest algorithm change?”

“Yeah, oh man, I saw that. Oh, by the way, did you notice that our ranking increased…”

And we'll just start talking about random stuff. We'll leave it on for two hours and digitally hang out and work. It’s an odd but satisfying connection when you're working remotely with someone and you can't see them. 

Joe

One thing we try to do here is to create connection points that people may talk about informally.

Not everybody's into sports, but we have some remote workers in Mexico, and some in Europe, and they know nothing about college basketball but they filled out March Madness brackets because we gave away an Amazon gift card to the winner.

So, it kind of gets everyone connecting and creates a nice informal connection point. Oscar predictions or a Slack book club are other things we try to do here.

Gaetano

We have a random Slack Channel and the rule is to drop random crap in there that's interesting and sparks non-work-related discussion. Sometimes it's good to include humor, even in an Asana thread. It lightens the mood and spices things up rather than just saying, “Okay, task completed, move on to the next task,” like a robot.

I would just say, work is kind of personal now, so don't be afraid to get involved in the personal lives of your team members.

For example, one of my employees just texted me and said that their grandfather is sick and may not be alive much longer.

I said, “well, just go home, be with your family.” 

That's the reality now.

I feel good about my team members being open with me to be able to say stuff like that, even though it's heavy.

When you allow that, there's more trust, more openness, and it's just easier. You don't have to beat around the bush about stuff, you can just take care of what you got to take care of and move on.

John

That's a really good point.

Trust is a huge piece of making this remote work thing...work.

Two weeks ago, Gallup released a stat that said, the most engaged employees were employees who worked three to four days remotely. 

A lot of it is about establishing trust with your peers.

If they're counting on you to get something done, you're going to get it done.

2. How to Set Expectations for Hours Working, Availability, and Communication

The Importance of Setting Expectations for Hours, Availability, and Communication


Joe

I think a big piece of this is trust, it's understanding when people are going to be available and also understanding that we all need breaks, we're not robots. 

Gaetano

I think every culture kind of creates their own version of this.

There probably is not one blanket rule that will work for every company, but I will tell you that with our team, we don't have many rules around this at all.

It's just, get your work done.

If there's a huge window throughout the day where you're not responsive, we'll just assume you're in meetings or we'll assume that you’re head down doing some deep work.

I'm a huge believer in deep work and I don't want to create the kind of culture where everyone has to time block.

I fully trust our team. They can work around the clock if they want to.

I'm a night owl, so I have a very weird workflow and everyone knows that. I'm the kind of person who's gonna be in a sauna at 2:00 a.m. leaving comments and cleaning things up, but that doesn't mean I expect them to be responsive, that's just what works for me.

The area where we do keep a time balance is in our AdWords schedule because there are peaks throughout the day where traffic is high and bids are high, and we do need somebody on that monitoring it during the times that are really high volume for us.

Joe

Let's go a little bit deeper before we go over to John. 

Gaetano, what’s your process for management? Is it weekly or quarterly checking in on goals? Or something else?

Gaetano

We're scrum weekly, so we have weekly sprints we operate in the same way that a development team will operate and we have a huge kind of wave of different things that we need to accomplish on a weekly basis.

There's brand, SEO, lead generation, advertising and we have to work really closely with creatives. There's a lot of collaboration that has to happen between many different departments and marketing products.

We have a sprint planning session on Mondays and a sprint conclusion session on Fridays, and then that obviously has to align with our monthly goals, and we have daily marketing.

Our team has a daily quota and a monthly quota, so we keep track of where we're at on our commitment to sales, and if we're falling behind, that's when we call audibles and see how we can make it up.

But we do have responsibilities. If you're not going to commit, if you're not gonna be able to make what you commit to by Friday, you need to speak up by Wednesday. That's pretty much how we run things and we love it.

John

We also have scrums and sprints for certain of our projects. 

The other piece is finding time to get together and have unstructured planning sessions. We have a few of those on a weekly cadence and then one-on-ones to make sure that people have a chance to bring up things that they might not be comfortable talking about in a broader meeting context.

John

If someone texts by phone or if it's a Slack notification, then I know someone needs something sooner than if they had sent an email. 

It's a bit of a balancing act.

Gaetano

Not everybody is gonna use Slack. I think we're trying to seriously move all communication to Asana and we're doing pretty good at that.

We did have a problem at one point of some people using Slack, some people using email, and so on. 

But we all rallied around the idea to keep all task-related discussion in Asana and big-ticket things in email, and then for quick little things, use Slack. 

Joe

I do a lot of work with our designers on our website and landing pages, and setting up webinars like this.

Instead of having to type out a massively long email, I use CloudApp to take some screenshots or record my screen and point out where I’d like some icons, for example, or what typos and errors need fixing. It’s really nice to just annotate on the screenshot and do it visually. 

3. Tools for Managing and Communicating Remotely

Managing Tools & Communication


Gaetano

Obviously, we use Nextiva, which is a business phone service and cloud communication app.

The thing that I love about it is, I don't have to have my phone at my desk. I don't even need a desk phone or my cell phone near me.

Besides Asana and Nextiva, we're using Google Sheets and Google Docs. We also use Evernote.

John 

Slack is a major one for asynchronous chats. We use some of the Atlassian tools, like JIRA and stuff.

We also use Airtable for content collaboration. All of our content projects are on Airtable.

We have office 365 as well.

Joe

I don't know exactly how to ask this but what's the best way to connect your tool stack so that it is being used effectively? 

John

If the information is only in that tool and you need that information, you're going to be incentivized to use it.

A lot of it is about integration. At BlueJeans, we've integrated with Slack. The same with Outlook or Google Calendar.

Not every tool needs to integrate with every other tool, but we try to integrate them where it makes sense for a seamless workflow. 

Gaetano

We have Wednesday learning workshops where we’ll deep dive into a specific subject, i.e. how to use Ahrefs to do keyword research or how to understand a Hotjar heatmap.

That type of collaboration - even though it's through cloud - helps team members feel more confident using these tools, resulting in a well-oiled machine.

4. How to Motivate a Remote Team


Joe

How do you motivate yourself and your team to get up every morning and get ready to conquer the day and keep growing on each goal?

Gaetano

One person on my team gets very motivated when I have one-on-ones and do deep dives with her. She’s motivated by knowledge. Another team member is motivated by money.

I'm down here in beautiful Miami, Florida. It’s enough for me to wake up, look out my window, see sunshine and palm trees. I’m motivated.

What it comes down to is, you gotta know what motivates each individual person and use that as the carrot to inspire them.

John

I think Gaetano said it well: everyone has different motivations that get them excited to work. We have a couple people who are intense skiers in our group and we've worked it out so they can live in the mountains, they don't have to be here in California.

The other thing is, figuring out what's next in your career.

What skills do you need to build? What experiences do you need to have? What’s the reason for staying at this job? 

Zero in on that and then find ways to carve out projects for people so they can take ownership over learning a new skill or anything else career-development related.

Joe

I encourage my team to have quarterly chats with me, where it's not tactical, it's asking questions like, “how's your career?”  “How are you feeling about CloudApp?” “What can I do better as a manager?”

I try to support candid conversations, especially those that require preparation beforehand, such as, talking about salary and benefits.

How to Communicate With Your Remote Team so They Listen and Execute

A visual communication tool is the most important means of communication for long-term success in managing a remote team. 

At CloudApp, we believe fast and easy collaboration is key to keeping employees productive - boosting your bottom line and strengthening your company culture.

That’s why we’ve built a tool that brings HD screen and webcam recording, GIF creation, screenshots and annotations to the cloud in an easy-to-use, enterprise-grade app so you can quickly create and share visual content.

We’ve also been ranked by G2 Crowd as one of the top sales enablement tools.

Find out how CloudApp can help you build and manage remote teams today.


Read part 2 of the recap here.

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