One Year in Managing a Fully Remote Team – Here’s What I’ve learned

8:30am, Portland, Maine (the Portland that has Lobster, lots of snow, and at 68,000 people is the largest city in Maine). I’ve hit my snooze button a few times, but I’ve finally decided it’s time to drag myself out of bed, take a shower, and open my computer. This commences work. I can walk the 8 seconds to my couch, plop down with my french press, and bang out a 10-12 hr work day managing 8 people over three teams without leaving my living room.

2:30am, also Portland, Maine, but 11:30pm on the West Coast. I’m awake before my alarm rings, which at this point is a safety measure. I quickly turn the impending doom of a loud ringing off so that my wife, who’s due for rounds at the hospital in 3 hours, hears nothing. I pick up my suitcase, stuff my MacBook Pro into my backpack, do a quick check that I have everything, call a Lyft destined for a 5 minute ride to the Portland Transportation Center, and leave. At 3:15am, the Concord Lines Coach backs out of the parking lot and rolls smoothly onto I-295 South, destined for Boston’s Logan Airport. When I arrive at Terminal C, I’ve barely slept, and blew through my two bags of pretzels, but I head through security and straight for gate 42. “Passenger Strong, Nathanael” and there’s my upgrade. I basically know the gate agent who hands me my new boarding pass – we’ve been through this dance before. At 6:35am, I board the plane and am whisked off to San Francisco. I get into the office in Oakland at about 11:30pm Pacific Time, and get to my Airbnb at around 6:30pm at which time I collapse. The 8 cups of coffee I’ve had that day have all but worn off.

8:00am, Wichita, Kansas. I’m showered and ready in a button down and jeans. It’s going to be a long day, but not with calls – with driving. I’ve got to take my rental Kia Sorrento 3.5 hrs from Wichita to Baxter Springs, KS – all the way on the border of Oklahoma and Missouri. After being there for about an hour, we’ll drive all the way back to Wichita.

These are three examples of what the past year of my work life has looked like – and it’s a complete study in contrast. About ½ of the time, I’m bumming around my house for hours each day, zooming all of my employees only to be interrupted by the clicking of Slack notifications. The rest of the time, I’m either at our Headquarters, where only one of my team members actually sits, or out on the road with customers – and they’re everywhere in the US (this month alone, I’ll be in Detroit, Cincinnati, Dayton, Rural Ohio, NYC, Dallas, San Antonio, and Austin). But through that year, I’ve learned a few things about working remotely, and managing a remote team. Some of them are not surprising – in fact they may even seem repetitive. Others, I think are new learnings that hopefully will help remote workers everywhere.

To start, after managing a fully remote team, I’m still surprised that tech companies want their employees in offices so much. An average company in the Bay Area pays about $3,000 per quarter for office space per employee – and if you’ve ever worked in the Bay, you know that the desk sits empty at least 2 days a week because of the flexible work environments offered. I actually think that besides the considerable cost savings of not hiring employees in the Bay Area due to salary premiums, you could spend ⅓ of the amount spent on office space each quarter and have a fantastic team or company retreat, which as you’ll see later, is what I think is required for remote teams.

But I also said I would have lessons learned, so here they are:

Hire the Right People, Set the Right Goals
This first lesson should get a resounding “well, duh” from just about everyone. But if you think about it – we need to be reminded of this over and over again! I don’t think this is any different for remote workers than it is for office workers, but since you can’t “watch over their shoulder” so to speak, you really need to focus on this. Often the cheaper or less experienced option is very attractive, but the wrong hire can cost you dearly. I can think of one particularly disastrous hire we made – and pretty much the only person who I feel has truly taken advantage of the flexible work from home environment we have – and the failure was we thought that even without experience we could train the employee. We were very wrong.

Goal-setting, however can be very tough. Even in Sales, where you’d think it’s easy – hit the revenue goal we need, you get paid – it’s a little more nuanced. When I started managing our sales team, nobody was hitting their goal. They weren’t even getting close. Now I’ve been in several organizations where leaders just get mad that their team can’t hit expected sales goals and they either PIP, or fire whole teams of salespeople. I took a different tack.

First, I restructured the team to make them more efficient. Second, I built Salesforce dashboards that track every stage and aspect of the Sales process. Finally, I significantly lowered the sales goals for the team into “reality” territory and showed each team member how they could hit their goals with the resources that we have. It wasn’t perfect – it took a quarter for us to align, but now we have much more predictable sales, and now that the goals are in line, I can start increasing quotas. And, because all of the KPIs are measurable and public for everyone to see, we have whole-team accountability.

Buy the right technology
I love technology. Yes, in a Kip singing kind of way (#millenial reference). One of the main functions of my job is to enable my team with the right technology purchases and implementations. In fact, one of the first things that I did when I came into my job was buy Salesforce.

But what was the most interesting thing about buying Salesforce was the amount of opinions I received from people all across the spectrum (including investors) telling me not to buy Salesforce. Fortunately, I ignored everyone and made the purchase anyways. Here’s the deal – at some point down the line, we are going to need to purchase Salesforce, and it’s way better to start now and get the data in there than have to migrate 2-3 years later when we eventually make the switch.

Often I know people recommend not going with Salesforce because they know it’s a complicated process to implement and manage. And that I would agree, but that’s why every sales leader, regardless of the size of their organization should at least know how to build their own Salesforce reports and Dashboards. Fortunately I’ve been a Salesforce admin for many years so not only can I do that, but I have set up many of my own custom objects (which I’ll be talking about in later posts).

I say all of this to say that it’s extremely important that you use the right technology when managing a remote team. A lot of the standard office cross-talk that is actually productive just is nonexistent in a remote workplace. Using the right technology is essential. One of the ways that I see this is in the use of a paper notepad, which I have all but banned on my teams. This isn’t because I’m an evil tyrant, but because when you write something down on a piece of paper, it is local to that one person. And if I can’t swing by your desk and ask you questions at random, I need to be able to see what tasks you’re working on. It’s so key to have as much data in central, cloud-based technology as possible.

But, this is not an excuse for buying random technology on any whim. Be strategic – buy the right technology that works right for your team, and encompasses as much functionality as possible.

Meet Often, Keep the Video On
One of the things that keeps connecting us as a team is our intentionality with how we meet and check in. We make it extremely easy to call each other on Zoom on a regular basis (which happens all throughout the day). We also have a very strict policy of turning the video on. This is the next best thing to being there with someone in person – you can see facial cues that you would miss otherwise. You’re able to communicate in more of a real-time setting. And yes, there’s a little bit of accountability.

A lot of people think this might be a little much, but it’s so imperative and so great for our culture to have active communication with the video on. Working from home is a great thing, but doing things like having the video on is imperative to maintaining a great culture.

Get Ready for Each Day
Yes, I wear whatever I want to work each day and my commute is about 2 seconds. But regardless of what happens, I still get up at a regular time (albeit a little later than I would if I had to commute to work), shower, and “get ready” for work. I make my coffee and my breakfast each morning and sit down at my desk to work.

Does that mean that I don’t sometimes spend the day on my couch or at my kitchen table? Absolutely not. I take advantage of the environment I have around me. However, I never, ever, ever, work in bed. Make sure you stick to a routine in the morning much like you would when you go to an office, and work as if you would in a very casual office.

Also pick times to get up and walk around. Do your laundry! Take a break. Go get lunch or coffee. Breaks are a normal part of the workday, and you should not forgo them (like I too often do) when you work from home.

Remote work is becoming more and more regular. After managing a team of 8 people for more than a year, I see it as more positive than negative. It helps us be closer to our customers. It helps me recruit employees because we have a flexible work environment. And it’s nice for me, especially with a medical resident as a spouse to have breaks at home when she’s on a 3pm-midnight shift that day.

Have you worked remotely? Are you thinking about working remotely? What are your thoughts on what I’ve put here?

  1 comment for “One Year in Managing a Fully Remote Team – Here’s What I’ve learned

  1. Annie Mae Platter
    September 10, 2019 at 9:05 am

    Well written, insightful, and helpful. Thank you for sharing, Nate. I will definitely be using in my highly likely – future remote work.

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