OKRs: A CEO's Perspective

by Giulia Pines

OKRs: A CEO's Perspective

by Giulia Pines
Courtesy of Paul Barbara

An office-wide excel spreadsheet transparently levels the playing field at Apartment Therapy.


Giulia Pines
Published on 09.05.2019

Some CEOs sequester themselves in corner offices with great views. Others work behind floor-to-ceiling glass partitions in an effort to appear connected to employees. Some don’t come into the office at all; others are far too involved. But nothing levels the playing field quite like having a master plan.

That may not have been what Maxwell Ryan called it at the beginning of the year when he set up an excel spreadsheet, labeled simply, “Company OKRs” to track his company’s goals and accomplishments. But it certainly felt like one: a central place where anyone in the company could look for instruction and to stay in the know, so that no one would fall behind or feel awkward about asking for clarification. He was essentially giving the entire staff access to the inner workings of the company - a level of vulnerability that would make many bosses hesitate – and creating a blueprint for how an office powered by OKRs should run.

Overhauling management is never easy, especially when you want to encourage people to opt in, becoming doers instead of spectators in their own work lives. But that’s what OKRs expect of us, and the results can be life-changing. Getting the office on the same page can take time and dedication, and that’s why CEOs have to be on top of things every step of the way.

Courtesy of Paul BarbaraCourtesy of Paul Barbara

Of course, that doesn’t always sit well with upper management; those company leaders who have worked hard to get where they are and don’t always want to invest in learning in a new way. When Ryan first implemented OKRs in the office, he received a predictable amount of pushback from a few key staff members: “Some of them come from places where they were so enamored of their old office culture, they find this new office culture alien.”

In order to win them over, he found himself resorting to what he had learned in his previous career as a schoolteacher, recalling that the most successful classrooms operated within a reassuring structure: “They come in every morning, they shake your hand, you look them in the eye, you say ‘good morning.’ Not all children like it, but ultimately it serves as a backbone for everything you do. It moves the group to focus on their work, and pretty soon it becomes unconscious.” In offices, just as in classrooms, repetition breeds familiarity, and eventually acceptance and integration, as the routine becomes a natural part of company culture. Once there, certain practices like attending WINS meetings or filling out a master spreadsheet become ingrained, and objections fade in the face of the overwhelming evidence that these practices work.

No longer his classroom, but still with plenty of guidance to offer, Ryan began integrating the spreadsheet into Apartment Therapy’s weekly routine as well. “On Monday we take a look, and by Friday they know to update it by the end of the day, so all our numbers are fresh as we head into the weekend,” he explained. “It’s all about elevating transparency behind OKRs, tying them to a three-year goal, and making it a part of our working week that everybody looks at this page.”

Courtesy of Paul BarbaraCourtesy of Paul Barbara

But it’s even more than that: it’s part of a concerted effort on his part to put everyone on the same page, both literally and figuratively. If the CEO of a company is operating off of the same master plan as everyone else, everyone is equally vulnerable and equally powerful. That’s exactly what OKRs were designed for in the first place: to do away with power dynamics.

Part of that was leading his staff towards the “Company OKRs” spreadsheet, which is separated by quarters, months, projects, and goals, and accessible and editable by everyone. With everyone operating off the same list of goals as everyone else, everyone can learn from everyone else, and that levels the playing field in astonishing ways. “It’s a two-way street,” explained Ryan. “I have to role model all the time, so admitting a mistake is essential if I expect my employees to do the same. You can’t expect it if you don’t do it.”

One of those mistakes, in Ryan’s honest assessment, was a past reluctance to guide the ship too firmly, fearing being seen as too controlling: “I’ve been a more gentle leader,” he explained, and “I’ve deferred a lot in the past. But I came into the year realizing I’m on the hook for this whole thing and I absolutely have to tell people what we’re doing.”

After three years of practice, OKRs are central to the company’s culture. But even the best teachers realize they have more to learn. That's when the founder of Apartment Therapy, Maxwell Ryan, reached out for a virtual chat with WhatMatters.com co-founder, Ryan Panchadsaram. The coaching meeting with Panchadsaram featured only a few key players on the management team, and Ryan described how in previous years, the company would start out strong with their overarching OKRs, but then get side-tracked and lose focus after a few months. “We want OKRs to help us do more than just put out fires,” Ryan said, wondering, “Is clunky communication to blame? Are we too rigid? Are we trying to do too much or measure everything?”

Courtesy of Paul BarbaraCourtesy of Paul Barbara

Panchadsaram started off by reminding Ryan and the team that OKRs cannot replace good office culture and good leadership, what he called the “soft” part of the business. Ryan had obviously been successful at leading his team, and modeling the kind of goal-setting behavior he wanted to see among his office staff, so perhaps rigidity in long-term goals was the culprit. It’s a good idea to keep setting those big annual goals, Panchadsaram confirmed, but also to set quarterly goals that can be adjusted more easily according to the whims of a volatile media market. In other words, both annual and quarterly OKRs would allow Ryan and Apartment Therapy to complete a full marathon, so to speak, while also successfully finishing shorter sprints.

Instead of being thrown off course by market changes they had no control over, perhaps the secret is to set OKRs for each quarter and then ask, “what’s a problem we might face soon?” Anticipating the pivot that might be necessary would go a long way towards preventing those fires before they started, instead of putting them out when they’re burning.

In the coming months, Ryan and his team would have to test out exactly that theory, when Google shifted their algorithm in a way that profoundly affected Apartment Therapy’s web traffic. Instead of panicking, Ryan explained, “We did two Pop-up OKRs within the second quarter and a special reaction deep-dive to deal with SEO. We pulled some resources from other places too - we had to adjust, but it was the right thing to do.”

As Panchadsaram had explained in the meeting, and as Ryan had agreed, it was all part of a day’s work in transforming a successful business using OKRs.

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

Courtesy of Paul BarbaraCourtesy of Paul Barbara

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