Hippie CEO Life #15 - Staying Connected in a Remote World

July 22, 2022

Over the last two years, a large portion of the workforce was introduced to the concept of remote work for the very first time. In the very early days of the pandemic, companies were unsure how to handle the change, employees setup temporary work spaces on kitchen tables, and work continued (as best as possible) under the thought that this was only temporary.

Two years later, employees are still at kitchen tables, leadership is unsure what to do next, perhaps holding out hope that we are on the verge of things going back to the way they used to be, but those days are gone. The way we work has changed forever and we now find ourselves in a world where employees are demanding the freedom and autonomy that comes with being detached from the office.

But….being detached from the office, where it was much more natural for us to connect with others in our companies, comes with some very real challenges that must be met with deliberate solutions. If our strategy is one of “hope”, meaning we just hope things will organically work in this new digital first world, then we are lost. Only through deliberate design and action, will companies and employees flourish in this new digital first way of working.

We have been a digital first company since day 1 (3,399 days and counting) yet we don’t feel like we have all the answer, we never will. We are in a constant state of trying and learning how to be a more connected company. Some things we have tried failed spectacularly, others have proven the test of time to help bond the team together.

Here are a few things we are doing as a company to stay connected in a remote, digital first world:

Weekly 1:1’s

i have made a personal commitment to have a 30 minute, 1:1, with every member of the team, every week. “But Jason, how do you have time to do that every week?”

How do i not have time? i imagine if we were all together in the office, i would be randomly walking the halls and talking to everyone anyway and probably for a lot longer than 30 minutes each per week, so it only makes sense for me to invest this time in staying connected with everyone on the team.

If you are leading a team and you simply can not afford to spend 30 minutes talking individually with every one of your direct reports, then your team size is too big.

Again, this can’t be an organic thing where you hope team members will show up to chat with you when they need to feel connected, you have to be deliberate in making this happen on a routine cadence.

In-Person Time

As much as we have created a digital first environment where the team feels connected to each other, nothing replaces being together in-person. Before the pandemic hit, we would get the entire team together in Las Vegas, around an industry event, and use it as a time to celebrate, bond, and just have fun together. That time together was priceless and we have missed it the last two years.

Part of the team recently got together in Las Vegas to support one of our team members, Jenn, who was presenting at an industry conference. It was great to feel that in-person connection again but it wasn’t complete with half of the team not there.

For us, we committed to once a year but for you and your team, maybe it’s quarterly, maybe it’s every month. You have to figure out the right cadence for you and your team but prioritizing in-person time is critical for staying connected in a remote world.

Virtual Events

We have talked with several companies that create virtual events for digital first companies. Think of it as a company offsite, yet it’s done virtually. While this will never replace being together in person, it is a creative way of being together in-between the times you are actually together in person.

We are currently in the planning stages of hosting our first virtual event for the entire company, something fun where we will all participate in a shared activity together. i’m not going to talk about the specifics too much in case anyone else from 33 Sticks is reading this as i don’t want to spoil the surprise 😊

Photo Bonding

Our central hub for communicating with team members around the world is Slack. It’s here where the traditional “water cooler” conversations happen.

We have a dedicated Slack channel titled #where-is-33-sticks that team members use to share their view of the world.

i really love seeing Jon’s food photos as he explores the Bangkok culinary scene.

This week, we introduced a new Workflow in Slack that prompts team members to share photos every Friday, we call it Photo Bonding Friday

Whether it feels like your team naturally bonds remotely or not, it is in your best interest as a leader to prioritize time to think about, and be open to continual experimentation and learning, how you can be deliberate in creating an environment that is open, welcoming, and encourages your team to truly connect in a digital first world.

✌🏼💛