How To Lead A Remote Team Effectively, According To The Experts

Six top takeaways from a new webinar series on how to manage remote teams.
  • The coronavirus pandemic is forcing teams to work remotely, causing fresh challenges for managers.
  • Questions like: “how do I measure performance?”, “how often should I check in with my team?” and “how do I onboard new starters remotely?” are gaining traction on Google.
  • Allwork.Space attended a webinar by Help Scout, a remote help desk software company, and identified 6 top takeaways.

Managing a remote team for the first time can be challenging.

Managing a remote team for the first time during a pandemic, with no phased transition or proper planning time, can be nothing short of daunting!

The coronavirus outbreak has forced many businesses into the remote environment virtually (no pun intended) overnight. Understandably, this has left a lot of business leaders feeling anxious and wondering what to do next.

Questions like: “how do I measure performance?”, “how often should I check in with my team?” and “how do I onboard new starters remotely?” are gaining traction on Google.

Fortunately, there are a number of remote-first businesses out there willing to share their pearls of wisdom. One such company is Help Scout, a global remote help desk software company with headquarters in Boston, Massachusetts.

Over the coming weeks, they’ll be tackling the big topics relating to telecommuting, including how to survive when working from home with kids, through live Q&As.

We tuned into the first in the series which focused on how to take your team remote

Here’s what we gleaned.

1. Acknowledge that we’re operating under suboptimal circumstances

A lot of us are worrying about how to stay productive at the moment. When we feel like we’re not doing enough, a helpless (and unhelpful) sense of guilt sets in. 

First and foremost, it’s important for business leaders to acknowledge that we’re not operating under normal circumstances, explains Help Scout’s CEO Nick Francis.

“The crisis we’re going through worldwide right now is unique, so when it comes to being productive, I’d encourage other founders and leaders to think about productivity in the proper context and know that none of us are going to be fully productive.

“The first part of being successful in this sort of environment is just acknowledging how ‘not normal’ this is.”

Nick also admits that even though telecommuting is in his company’s DNA, they’re still struggling with the challenges the current circumstances are posing. Leaders need to remember that many people are juggling work with other things, like parenting.

“Encourage your team to take a deep breath. 

“Try to show real empathy and compassion for what might be going on psychologically and whatever stress they may be feeling as a result of this, not to mention any health challenges they may be feeling themselves or on behalf or their friends and family.”

Morgan Smith-Lenyard, Help Scout’s People Ops Partner, points out that establishing a routine from the get go can be really helpful, even if it takes a while to find what works.

“It took me a good 10 variations before I found at least two or three routines that worked for me regularly.

“Your routine should factor in the breaks you’d take in a co-located environment, whether it’s going to get water or coffee, chatting to the person in the cubical over – just do whatever you need to do to get that space.”

Morgan also admits that the list of goals she set herself this week was intentionally short. 

“Set goals for yourself but don’t be too overly ambitious; be kind to yourself and to others on your team,” she advises.

Morgan Smith-Lenyard advises establishing a routine from the get go, even if it takes a while to find what works.

2. Accept that kids come first and plan around them

“I start my day with coffee and end it with wine!” jokes Morgan. (I’m sure many of us do!)

She says that the transition into remote working for parents will depend on, for example, the age of their child(ren) and the type of work they’re doing.

“The short of it is my kids come first and I feel blessed to work for a company that understands and celebrates that.

“What’s worked best for me is to know that work can wait, but also finding areas where I know that I can fit work in, such as nap time – that’s when I try to make most of my calls.”

Setting expectations is also important. Morgan operates a clear expectations and rewards system. For example, after lunch she tells her children that she’s going to work for 30 minutes and then they’ll take a break and play soccer.

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“Also, it’s cute if kids pop into a meeting every now and again!”

Does anyone remember this viral video?

3. Focus on and properly fund the culture side of your business

Nick emphasises the importance of team culture when it comes to leading a remote team successfully. Tools are useful, but human interaction is key. 

“Dharmesh Shah, co-founder and CTO of HubSpot, says your company has two different products – one is the product itself and the other is the company culture. 

“What I’ve observed over the years is that not only is Dharmesh right by saying that, but a lot of the companies I talk with don’t necessarily invest in the culture at the same pace and with the same aggression as their product.

So when it comes to building engagement within your team, you need to give people the space to dedicate their time to it.”

“One of the best things we did in the early days of Help Scout was to overinvest in people ops. Out of our first 30 people, three were dedicated to people ops.”

In other words, your company culture will have an impact on how connected people are remotely, so you need to invest in it.

Nick also notes that in a physical workspace, information gets passed along by osmosis, so leaders need to think about how they are going to communicate information more consciously in a remote context.

“In a remote culture you have to be so intentional about simulating how information carries. Replace the water cooler moments through events like online Fikas and one-to-ones. 

“You have to be so intentional about it; it’s not going to happen naturally as it would in a co-located environment.” 

“Make those one-to-ones useful by asking the difficult questions and get beneath the surface so it’s not just a status update; it’s about building trust and your relationship with that person.”

4. Celebrate achievements with individuals and your team

It’s important to celebrate achievements and give people the validation they need in different ways. Here are three things Help Scout is doing right now:

  • The company has a Slack room called Warm & Fuzzy in which anyone can celebrate anyone else in the company. (Unstructured, accessible)
  • They took their annual retreat virtual this year and a dozen members of the team shared videos of themselves talking about the contributions another team member had made. (Public)
  • Help Scout runs an ongoing programme for spot bonuses whereby managers have the authority to give their team members a bonus of up to $500 when they go above and beyond. (Personal)

5. Be open about mental health

“Making yourself an organisation that feels strongly about talking openly about mental health and removing any stigma is important,” says Morgan.

She also highlights that there are some great remote therapy options out there.

“Imposter syndrome can become an issue as people don’t get the same level of validation at home. This causes people to feel like they’re not working enough so they work harder,” explains Nick. 

“But this means they don’t give themselves as much grace or as much of a mental health break. Contributors need to know that this is common and be able to recognise it.

“As a manager you need to be looking for signs of imposter syndrome and burnout and give people the validation and certainty they’re looking for about their performance. Also, encourage your team members to take breaks regularly.”

6. Focus on getting to know people when onboarding new employees

Morgan suggests that getting that face-to-face time in via videoconferencing, while giving people space, is what business leaders should focus on when onboarding remotely. Set goals centred around getting to know the business, team and customers. 

Talking to people can make people feel like they’re not “achieving” a lot, but, as a manager, you should “really hit home that this is the work and it’s what’s important right now,” Morgan explains.

She adds: “Create opportunities for people to build relationships and get to know each other. The work really is secondary.”

Finally, Nick believes that to lead a remote team successfully, business leaders need to be transparent about where the company is at. Even if the information being communicated is sometimes difficult to digest, your team will appreciate your honesty and the clarity it brings.

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