Congrats – you’ve been promoted and now you are leading a team! Does that mean your dream of working remotely has gone up in flames? In my experience, absolutely not!

Leading a Team from Anywhere - Photo at Falls Lake NC August 2018

For this post I want to focus on how to transition to remote work if you have a lot of “people” dependencies in your role. In the prior post I covered Overcoming Challenges in an Autonomous Position, which should cover you if you don’t have these dependencies.

Here’s a quick recap of the 5 key tips from the last post:

  1. Establish a dedicated space
  2. Block your schedule in a highly effective system
  3. Portion out the work
  4. Make at least 50% of your working time overlap with the rest of the organization/team
  5. Over communicate your status

You can read the full post here, but let’s dive in to the new stuff now!

Alignment is Key

Unlike that role in 2004, in 2014 a motorcycle accident forced me into remote work. I was leading a team of 5 at Zenefits that was critical to fueling the companies growth.  This was certainly not the ideal time to be laid up or out of the office for an extended time. Startups stay lean by intentionally eliminating overlap or duplication of skills/work.

The culture at Zenefits was very spur of the moment/walk by conversation/informal which created some unique challenges to my prior experience working virtually. I will tell you right now, if the company/team isn’t on board and you’re in this type of role – it will be nearly impossible to succeed. That means your first step is to get the team on board with your transition. I was very candid about my limitations, inconsistency in my schedule/availability, and uncertainty of what I would be able to do.

A huge upside to the small company/startup environment is that people are familiar with change – it’s the norm so this was just the change of the week (months) for most of the team.

Once everyone, including our CEO, was aligned and understood the situation and plan I started on the real tasks of leading the team from afar. The first real task was to break down recurring tasks and delegating everything possible. I needed to shift from being primary to being backup for things that happened often and were mission critical. This meant rebalancing the work and focusing on my employees and spending a good bit of time on video calls training them up on how to do things.

Removing/Limiting Dependency on Recurring Tasks

With mission critical tasks handled, my schedule was cleared enough to focus on other things. I spent the time I had focusing on the infrequent and strategic tasks that could not be handled by the existing team.

Creating Visibility while Leading a Team

One of the challenges I faced while focusing more explicitly on the strategic tasks is that there aren’t interim deliverables/documents when you’re in the midst of process design, new campaigns, establishing new vendor relationships and those types of things. Also, while my manager was very understanding about why I couldn’t be there, he didn’t always appreciate the time it took to do something the right way and had trouble focusing (aka reading emails) with updates.

To overcome this challenge, I deployed a series of different touch points, primarily informal with a few more formal ones mixed in. This combination ended up working well for a lot of other leaders that I worked closely with.

  • Instant Chat check-ins
  • Use Instant Chat Program status
  • Weekly team video meetings
  • Bi-weekly individual 1:1s
  • Video updates/tutorials

I’ll briefly describe each of them for you here but if you’d like more detail on anything just leave a comment below – just don’t want to bore anyone taking the time to read this!

Instant Chat Program

The Zenefits culture frowned upon email for internal communication. We relied heavily on Google Hangouts and Slack for almost all internal updates. I used these programs just like I was in the office to pop by and ask key people how things were going and if they needed anything or to let them know what I was working on if it was potentially going to impact them or their team. The easy ability to take a chat and turn it into video or voice on the fly without the formality of scheduling a meeting/blocking time on someone’s calendar worked much better for our company culture.

I also used status messages to let people know if I was away or working heads down on something. Instead of the standard Available/Away/Busy response I used custom statuses like – With Physical Therapist or Working on XX Campaign. I also made sure that everyone knew that when I was online and available, it meant I really was online and available.

This took reinforcement and repetition so don’t expect instant recognition when you change your behavior. Over time people really started to understand they could depend on these messages. Dedicate the personal discipline and ensure messages are always up to date and that you sign out when you end your day.


During the course of my recovery, I added people to the team and we restructured responsibilities. This led to increased interdependency and complexity between individuals. At the time, Zenefits used a video conferencing platform called High Five but it wasn’t available in every single conference room in the offices. Part of what I always did for any meetings that I scheduled was to ensure that there was a video link or dial-in information in the invite as well as a clearly stated objective and agenda. This set expectations for the team and allowed us to keep meetings shorter and more focused.

If you’re invited to another person’s meeting that doesn’t include virtual connection information, simply create the links and send them to the organizer and ask them to update the invite. People will quickly catch on and develop this same approach without you saying anything. Do the same when the topic is vague, or the attendees don’t make things completely clear. I would often have someone from my team join the meeting in person as well, so they could get the information firsthand if it was something I was going to assign to them or was related to something else they were already working on.

Challenge the person in the room to lead and represent the team. Assure them that you’re there for support and chime in when necessary, but try to have the majority of the coaching done away from the larger group in your 1:1s. This establishes their authority with other teams in projects and ensures they’re seen as the resource on the topic. Preparation also helps junior members of the team build confidence which is key to credibility and internal relationships.

Video Updates

Another thing I did a lot when training, troubleshooting, or trying to relay more complex information was to record quick screencast videos with voiceover instructions. Doing this eliminated the need for so many meetings or the duplication/repetition to lots of different people. A frequent scenario was around new campaign launches. These often required slightly different inputs from the sales team for tracking and attribution. As teams grow it becomes more and more complex to get time (and more importantly- attention) with the full team. Regardless of whether you are in the office or remote these quick videos were a powerful tool. They always focused first on the benefits for the rep and were as short as possible.

What next?

I eventually left Zenefits and went to lead marketing at another startup, TripActions. Sadly the bone infection reared its ugly head again so I found myself remote for 6 months again as a member of the executive team. It was no surprise to me, although it was to the team, that the same process worked well once again. I’ve battle tested these principles and guarantee they’ll get you off to a great head start in your remote venture!

Please let me know your thoughts and if you agree or disagree! I’d love to continue the conversation. If you enjoyed this post, perhaps someone else in your network would too – why not share it with them?!