Drift’s Dena Upton Wants You to Avoid 98% of Meetings. Here’s Why (And How to Do It for Yourself).

Editor's Note: The following article is an excerpt from our book Better Meetings Every Time: The Secret to More Productive Meetings in a Digital World. You can access the entire book here.

“It took being forced into remote work to realize that the assumptions we were making about the advantages of being in-office were all wrong,” she says. Those assumptions were that 1) people needed to be in the same physical space to truly collaborate, and 2) that working in an office space made people more productive.

Now, Drift has become one of the first hypergrowth companies to announce their move to Digital First – for good. That means everyone at the company will work remotely, with the eventual option to use Drift’s existing offices as Conversation Spaces once it’s safe to do so.

“We actually realized that going remote allowed people to be much more productive,” says Dena. “The last year has taught us so much about flexibility and remote work, and we’ve realized that it really works. We’ve gone through a one-way door, and knowing what we know now, we can’t go back.”

Lose the office, gain a whole lot

To Dena, making the change to Digital First signifies that Drift is learning how to thrive in a world where outcomes achieved matter more than hours in the office. “I talk to people who say, ‘I can’t believe you guys are going to make this digital, remote-first thing actually work,’ and my response is, ‘You have to! It’s the new way of working,’” she says.

Three things became clear when Drift went fully remote:

Productivity increased

“When everyone is remote, the idea of proximity is taken away,” says Dena. “We’re focused more now on outcomes and execution and how people actually do their jobs in the hours in which they’re most effective.”

Ultimately, this leads to a more productive – and more equitable – work environment. Work goes to the most qualified person, no matter where they are, and people are rewarded for a job well done whether or not they’ve put in the appropriate “face time”.

The talent pool grew

Before the pandemic, Drift was very much focused on hiring people who could be in-office.

“When we went remote,” says Dena, “We suddenly had access to a talent pool we wouldn’t have considered before, due to those in-person rigorous requirements.”

Having added over 200 Drifters in the last year alone, 40% of the team is now located outside of the Boston headquarters. Not being bound by location has allowed Drift to find the best people for the job at hand, no matter where they work. 

It was still possible to connect

With a culture that prioritized physical proximity, how would things change in a remote setting? Would it still be possible to feel connected to colleagues while working from home? Thankfully, the answer was yes – with a slight caveat. “When you’re gathering virtually you have to re-create the energy that might have come more naturally in person,” says Dena.

“We’ve really upped the production value of our meeting slides and added fun things like music to get people energized.”

Does it really need to be a meeting?

It was a relief to Dena to see that gathering virtually could still create a feeling of togetherness. 

Prior to the pandemic, each week at Drift was bookended by two meetings: Monday Metrics and Friday Show & Tell. These meetings were done in-person, and functioned as a way to keep everyone looped in on what was going on in the company in terms of sales, marketing, hiring, product, and other exciting new projects.

These meetings still exist, but are now completely virtual. “It just meant we had to up the production value,” says Dena. “When you’re not together, you have to create that energy with better slideshows and more interactive and engaging features like music, voting, and  chat.”

Being aware of what’s required to make a virtual meeting engaging has only caused Drift to double-down on a point of view they’ve long held: that there should be as few meetings as possible in any given week.

It’s an often-repeated sentiment at Drift that meetings should be avoided 98% of the time. The internal communications team has even put together a number of resources meant to dissuade people from calling a meeting in the first place. “If you really think about why you think a meeting is necessary, it often doesn’t hold up to scrutiny,” says Dena.

Fewer meetings, more collaboration

Dena has found that when meetings are discouraged, new – and better – forms of communication and collaboration step in to take their place. 

For example, if the purpose of a proposed meeting is to collaborate, this can be done asynchronously via Google Docs. Similarly, if the purpose of a meeting is to share information, maybe an update using Drift Video is a better idea, or a Wiki post, or even just a simple Slack message.

Having just expanded internationally with new teams in both Australia and London, the idea of asynchronous communication has become even more important at Drift. “We never want team members in different locations to feel like they’re a satellite office,” says Dena. 

This is much easier to achieve when people have options for how they can contribute. “Even when it comes to all-staff meetings, they’re recorded and available for consumption at any time, so the experience that someone would get attending the meeting live is the same as it would be for someone in Australia.”

Survival of the sacred

Fortunately, and in spite of the pandemic, Drift has continued its rapid growth, and Dena notes that as a rule of thumb, there’s a tendency for people to feel the need to call more meetings as a company gets bigger and more complex. Continuing to fight against this ethos has only made the existing, necessary meetings all the more sacred. 

“There are meetings you’ll never be able to replace with other tools, like one-on-ones and skip-levels,” says Dena. Likewise, sometimes problems need to be solved synchronously, with a true, real-time brainstorm.

No matter the meeting, the message is clear: “Our people know that if you’re in a meeting at Drift, it’s because someone values your feedback in that moment,” says Dena. “There’s an etiquette that’s come out of that. People are very good at shutting everything else down and not multitasking, at being present.”

Recognizing the limits of a remote-first world

Though the overall impact of going Digital First has been overwhelmingly positive, Dena admits that some things have been more challenging to iron out. “In a Digital First world, you end up working with the same eight to ten people quite a lot,” she says. “You don’t get much of a chance to see anyone else in the organization.” 

While the Monday and Friday video meetings are a great chance for everyone to gather virtually, there is still more effort required to recreate some aspects of office life, like unexpectedly chatting with someone you run into on your way to the kitchen. To remedy this, Drift is relying on things like the Slack donut bot 🍩 to randomly pair people up to have a coffee virtually.

Dena is also aware that further challenges could crop up as Drift starts making use of its Conversation Spaces (which were formerly used as offices). “Our leaders will have to set an example,” she says. “If your VP of Customer Success is in the office, the rest of the team will feel that they should be as well. It’s really important that we continue to create an equitable environment by being thoughtful about where and how we show up in person.” In other words, it’s going to take work not to fall back into old patterns.

For now, Dena is relying on regular employee engagement surveys to see what’s working and what could be revisited while everyone is working from home. Going Digital First is a big change, and it’s not something Drift is going to perfect all at once. But given the ease with which they’ve managed each stage of their growth so far, it’s a challenge they’re up for – and one they can work out using video meetings that are planned and executed with intention.

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