Ending the Week With a Win With OKRs

by Giulia Pines

Ending the Week With a Win With OKRs

by Giulia Pines

Learn how WINS meetings give everyone at Apartment Therapy a sense of collective accomplishment within an OKR cycle.


Published on 04.27.2019

It was 5pm on a Friday—a time when most office workers are thinking about packing it in. But at Apartment Therapy, things were about to get a bit rowdy. As employees found spots on a sofa or floor or ergonomic swivel chair, an office manager rolled out a cart of IPAs and cans of cider and popped the cork on a bottle of Prosecco. Apartment Therapy CEO and Founder Maxwell Ryan tested out a projection screen and a mic.

With the entire company comfortably seated, a few calling in remotely from all over the country, Ryan proceeded with an enthusiastic if somewhat self-effacing welcome: “We’ve never done this before, and it could be super awkward,” he began. “But I know it’s gonna be fun, and if you need help, we’ve got a full bar right here!” He gestured towards the Prosecco, now happily fizzing away in rows of glasses, before calling the first person to come up to the mic.

For the uninitiated, this may seem like a bizarre ritual, halfway between a boxing match and a karaoke session, akin to one of those motivational speaker conferences: six steps to becoming a better you. Actually, that last one isn’t too far off. This was Apartment Therapy’s monthly all-office WINS meeting, just one component of the goal-oriented business method Ryan has put into practice: OKRs, or Objectives and Key Results. A tool first developed by Andy Grove at Intel decades ago.

WINS meetings allow employees to celebrate their previous successes while looking ahead to the next ones, and they’re a crucial component of goal-setting when using OKRs. As a Grove disciple, John Doerr writes in Measure What Matters, “Quarterly goals establish and reestablish the areas where feedback and recognition are most valued. Transparent OKRs make it natural for coworkers to celebrate big WINS and smaller triumphs alike. All deserve their share of the limelight.” After all, how can you motivate employees to come up with new objectives if you don’t allow them the time and space to congratulate themselves on the ones they’ve already reached? The easiest way to do this is with a regular meeting that gives all members of a team the opportunity to sing their own praises.

Of course, as Ryan had found out at Apartment Therapy, that can be easier said than done. Some team leaders may not see the point of devoting an hour or more a week to what can seem like a mere recap. Some employees may be reluctant to come up with a weekly WIN, or simply uncomfortable with speaking in front of a group. The key is to read the room, and Ryan had spent several months doing exactly that before coming up with this current format. “It may not be for everybody,” he explained of his early attempts at creating an office environment ripe for WINS meetings to grow and flourish, “but the reality is, you’re relaxed at the end of the day. Some of the WINS were at 11am on Friday,” he continued, “but that’s a business meeting. This is almost off-duty.”

Indeed, there was a palpable feeling of relaxation, and not just because of the alcohol. A sense of fun permeated, as Apartment Therapy employees understood that this should feel like a celebration as much as an obligation. Operations Associate Michael Kuhn presented the team’s biggest WIN, a switch to checkless payment for freelancers, in the form of a poem with rhyming couplets—a feat so skilled it left everyone laughing and clapping at its sheer ingenuity, while also scheming about how to top his performance next time. Graphic designer Kath Nash, who had been responsible for viral images like the beloved Millennial Apartment Bingo, was celebrating her last day in the office before going freelance. She used her last WINS meeting to sum up her time at the company and offer a tearful farewell to colleagues. The general sense was that all-office WINS meetings were a way to come together, support each other, and celebrate the successes of the past month.

WINS meetings aren’t just a once-a-month thing, though. In fact, at Apartment Therapy, they now take place every Friday; a testament to the value Ryan sees in them as he shifts his company over to an OKR-powered workplace. Earlier that month the sales, editorial, and business teams had gotten together for smaller meetings, yielding WINS as diverse as a new video series called Dating Spaces (interviewing real people on their hilarious first impressions of dates’ apartments), big partnerships in the works with major brands like Casper, OXO, and Royal Caribbean, and even something as seemingly small but significant as an office manager cleaning out a long-neglected fridge. Each WIN was met with applause, imbuing each member of the team with an equal sense of value.

Even more importantly, as Ryan detailed in a phone call the previous week, teams weren’t just sticking to themselves when it came to weekly WINS meetings anymore: “They came to me and said, ‘We think the departments should mix on a weekly basis,’” he said. “We wanted to focus on content, editorial, artist development, art, video, and the creative studio. Now, on their own initiative, they’re hearing from departments they don’t know very well.” The result is an organic sense of cohesion not just within teams but across them—something many offices may find works to their benefit, as long as they’re willing to take the leap. After all, it takes a bit of trust to realize devoting time to these meetings out of a busy work schedule will yield palpable results.

For his part, Ryan has already seen great improvement in office morale: “Everyone has been calm and focused, the work that we specified is getting done, and there has been no drama,” he related with satisfaction. “There is accountability to our bigger goals. It’s keeping the whole organism of the company on track.” Perhaps that in itself is the biggest WIN of all.

Giulia Pines (@giuliapines) is a journalist, essayist, and content marketing strategist with a focus on travel, culture, and entrepreneurship.


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Get exclusive guidance from John, Ryan, and the What Matters team by signing up for our weekly newsletter, Audacious. You’ll learn week-by-week how to sharpen your OKRs and stay on track to reach your goals.