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How to Manage a Remote-First Team

When I hired my first employee for Her First $100K in 2019, I knew off the bat that giving my employees the benefit of remote work was a huge priority for my business.

The tides of change were shifting even then, and I realized there were so many pluses to me as a business owner and to my employees by creating a remote-first work culture. Having trouble with convincing your boss to let you work remotely? Here’s my guide to negotiating a work-at-home job and what to do if they say no.

I recently met with my core team at the sleek and stylish Hotel Interurban in Tukwila, Washington (just south of Seattle for you non-PNWers) for a three-day-long mid-year check-in and planning retreat. I try to plan at least two of these a year because I find them SO valuable for spending some quality time with the team and brainstorming the subsequent incredible launches we have coming your way.

Aside from these retreats, we remain a fully remote, worldwide team.

There are, of course, difficulties in having a remote team –– sometimes communication takes longer or can be murky, and with team members in different time zones scheduling meetings can be tricky. Overall, I’ve found a few tried and true ways to help my employees feel connected while also giving them the flexibility they love.

Building Better Systems

So much of the struggles of remote teams has to do with muddy communication –– but there’s a wealth of technology and innovation available to business owners that help keep things streamlined and communication pipelines clear.

We utilize project management software, Trello, that allows us to communicate within the platform on important projects and due dates. Our project manager keeps this system clean and updated, so everyone on the team has clear-cut goals to help us succeed.

During our retreat, we sat around the conference table in our private conference room at The Interurban and talked frankly about ways to improve communication, especially as our team gets bigger and becomes even more global. Some new ways we’re approaching this that may help your team, too:

• Getting specific in our Slack communications about deadlines, priorities, and details

• Using our Slack bio area to put our day-to-day availability and time zone

• Adding more details to our google calendar invites, especially if we’re taking half days or heading out on vacations

• Streamlining our Trello process to establish each of our preferences in task assignments

• Opening the door for frank and honest conversations about our workloads

Self-starter Culture

Over dinner and drinks at Hotel Interurban’s Waterleaf Restaurant and bar, we tried to keep the business conversation to a minimum, but the relaxed atmosphere struck up some of our creativity, and we couldn’t help but start to discuss the next meme we should use or the topics for next season’s Financial Feminist.

As we shared a bottle of the Waterleaf staff’s recommended rose, it struck me how much I love that I’ve built a team of ambitious self-starters –– an attitude that I think any remote team, especially in media space, needs to have.

When building out my team, I let potential employees know right off the bat that sometimes, because we are all remote, they’ll need to be willing to throw ideas into the ring and execute them with little feedback. We work in collaboration as often as we can, but sometimes it isn’t possible with the restrictions of zoom and schedules.

As we sat under the Waterleaf patio’s string lights, Mt. Rainer’s dusted peaks gleaming in the backdrop, we toasted to this team of kick-ass women and all that we’ve been able to do in the last year as a remote team.

Planning Retreats

It’s less expensive for me as a business owner to fly my employees out for these retreats than it is to rent or buy a full-time HQ (though I’ll never rule it out –– could you imagine how cool a Her First $100K headquarters would be?!). So, I take care in choosing locations that are fun, convenient, and optimized for working as a team without interruption. 

For this past retreat at Hotel Interurban, we started our mornings in their cozy coffee shop with our smattering of caffeinated beverages (and a few mouth-watering cinnamon rolls –– I highly recommend). Then, we headed into our private conference room, where we spent the day strategizing the next six months at Her First $100K.

We also took a dip in the hotel’s indoor pool on our final retreat day when we needed a good excuse to take a break and relax. A few of us even got a few laps in!

Staying at a hotel allowed us to have fun and get a lot of work done all in the same place, making coordinating meetings and events a breeze. In three days, we were able to plan six months of content and dream about the next several years here at Her First $100K.

Having Fun is a Priority

Staying in Tukwilla was a great escape from the hustle and bustle of downtown Seattle, but we couldn’t help but head into town for a night of fun and team bonding at an escape room called Quest Factor.

Like I said above, flying my team out for retreats is way more cost-effective, and because it is so cost-effective I get to spoil them with fun activities like escape rooms and dinner at Matt’s in the Market. 

Booking an Escape Room proved to be not only incredibly fun but a great bonding activity where each of my team members showcased their skills and communications styles. We naturally gravitated towards certain puzzles or riddles and were able to win two rooms before time ran out. It was a hilarious and challenging experience and provided some great stories and retellings throughout the rest of the evening (I f*cking lost it over a puzzle at one point lolz).

Another way we discussed having fun as a remote team is starting a virtual happy hour once a month to connect on a totally non-work level and build some community together. It’s no escape room, but it’s a fun way to “get together” like an in-person team might.

We had such an incredible time at Hotel Interurban, and when it came time to leave, the airport was a quick and convenient Lyft ride for those that flew in. As we said our goodbyes, I remembered once again how lucky I am to have a fully remote team who loves the community and mission at Her First $100K as much as I do.

A very special thank you to the team at Hotel Interurban who gifted us this stay. Their staff went above and beyond to make our visit exceptional, and their on-site restaurant is worth a visit even if you’re not staying with them (the dessert was especially divine).