Lessons from an Enterprise Rollout Gone Well

How one org used quarterly cycles, pilot teams, and the right tool to help scale OKRs

Sponsored by

Hey folks, 

Josh Seiden and I have recently revamped the website for our upcoming book on OKRs, Who Does What by How Much? Not only is it a new design, but it also showcases the cover for the book. What do you think? Hit reply and let me know. 

As part of the new book, we’ve sourced a series of case studies that highlight various ways companies have overcome the challenges of OKR implementation. I’m sharing one of those case studies in this newsletter. It’s about how a large enterprise used existing structures and some common sense to get their scaling efforts off to a good start. 

Have you seen these ideas work in your environment? I’d love to hear from you. 

- Jeff

Article: Lessons from an Enterprise OKR Rollout Gone Well

In advance of the new book, Josh and I spoke with a UK-based mass media and telecommunications company with more than 60,000 employees about their efforts to implement OKRs at scale. The organization started their org-wide OKR rollout with their London office. While they’ve had their share of obstacles, they shared three specific things that have made their scaled OKR journey ultimately successful: quarterly cycles, pilot teams and choosing the right tool.

1. Quarterly Cycles – Use the scaffolding you already have in place.

Prior to using OKRs, the company already used quarterly cycles as their standard check-in timeframes. Teams and leadership alike were used to them. When they began to work with OKRs, they decided to keep the same cycle length. This reduced confusion for teams as they took on new ways to set goals. 

It also reduced the risk of any team going too far down the wrong path since, in a worst case scenario, no team would spend more than 12 weeks chasing goals that didn’t make sense. While even 12 weeks may sound like a long time, in an enterprise setting, it often takes at least this long to collect the feedback needed to determine whether a team is on track or not. 

By minimizing the number of changes the teams were taking on at the outset of using a new process, the operations team increased the likelihood of broad OKR adoption across the organization.

2. Pilot Teams – Test the process before scaling broadly.

Changing thousands of people’s goals is a daunting and risky endeavor. The operations team running the OKR transformation recognized this and decided to start small—to run a “process experiment”—and roll out OKRs to what they called a “change team.” This change team was small by their standards—only 600 people, led by six executives—and was primarily made up of software developers who were already working on customer-facing products and services. Choosing a part of the business where OKRs would likely find an easy fit further increased their chances of successful OKR adoption. This part of the organization was already familiar with the quarterly cycle, and their direct access to end customers made setting and measuring goals more obvious. 

The operations team’s first big learning from the pilot effort came from asking the change teams to come up with their own goals. This enabled alignment and focus at the individual team level, however, it didn’t align any of the change teams to the broader organizational strategy. Without top-down strategic direction to point to, each team just did their own thing. After one quarter working with this bottom-up OKR approach, the operations team had to go back to the leadership team and ask them to prepare their own goals, align amongst themselves and then share their agreed-upon direction with the pilot teams. Once they had those high-level OKRs, the pilot teams could improve their own goals to align with the organization’s strategic focus, which increased alignment and allowed them to focus on the work that was most important, rather than who was “shouting the loudest” or “zombie projects,” as they were known, that weren’t going anywhere. 

Working with the pilot teams taught the company a lot about rolling out OKRs widely. For one, they learned that the change teams were not, in fact, ready to work on their own right away without specific direction and alignment coming from the top. For two, after the leadership team provided strategic direction and alignment between the change teams improved, the organization tried to start rolling out OKRs more broadly—and, as they learned, prematurely. While the change teams were indeed working well at that point, they still had enough doubts and challenges that required a high level of attention from the operations team to resolve. After attempting to add more teams to the rollout, the ops team realized they should have more thoroughly “de-bugged” the process with their pilot teams before beginning org-wide implementation. 

Ultimately, using pilot teams allowed the company to de-risk the rollout of OKRs with a smaller group and learn from their mistakes before implementing the framework at scale.

3. Choosing the Right Tool – The right tool increases transparency and work quality.

Generally speaking, we’re agnostic when it comes to tools. Use whatever works best for your team, organization and culture. In the case of this organization, though, we learned that choosing the right enterprise-level OKR management tool—Workboard, in this case—made a significant difference in both the quality of the OKRs they wrote and the success of the broader rollout. 

The operations team told us that at the beginning of the company’s OKR journey, the change teams often made features and other “output” part of their key results. But when they started using Workboard, the tool prompted them with specific questions about their goals—questions that made it clear to the team that their answers (and, thus, their goals) didn’t align with the input Workboard expected. The tool’s questions asked for outcomes, but the teams were using outputs. It was instantly evident that their OKRs had to change to get the right goals—ones that focus on outcomes—in place and align the teams more effectively. 

Workboard’s prompting for outcomes-based goals also changed how the company’s leadership assigned work to the change teams. Instead of telling them exactly what to do and how to do it, leadership left the execution up to the teams. After all, the goals were no longer about shipping a specific feature but rather about changing the behavior of customers visiting their physical and virtual stores (among other things). Leadership didn’t inherently know how to drive those behavior changes, so handing down lists of features wouldn’t work anymore.

Finally, the tool the company chose to help with their OKRs gave leadership visibility into the quality of the OKRs being written as well as what work choices the teams were making to achieve the new goals. It highlighted which teams were doing good work and which needed more attention. The executive team now uses the tool to check on the performance of each business unit (rather than the individual employees). They’re learning they’ve set too many goals, which has created dependencies that have slowed the change teams down. This kind of transparency has been invaluable to the continuous improvement of the company’s OKR efforts.

What I've been up to

February always seems to fly by. Highlights for this month include the debut of a couple of new keynotes focused on OKRs. I gave one at this year’s OKR Forum, a fun online event with a strong international audience. It focused on the idea that everyone has a customer and how that affects organizational strategy and, ultimately, execution. I debuted the second one, which shares the same name as our new book, Who Does What by How Much?, at a local Product Tank meetup. With nearly 200 people in attendance, it felt a bit like trial-by-fire to see how the new material would be received. 

Overall, both talks seemed to land pretty well. There’s always room to refine, sharpen and get punchlines just right, but it was a strong start. And it felt so good to be in front of people, speaking again. As much as I love working from home, there’s nothing like the “real world” energy you feel when presenting in person.

Beyond that, Josh and I have closed a handful of new training clients this year for our Product Management and Lean UX classes. If you’d like to get on our calendar for the first half of 2024, get in touch or just hit reply.

Watch, Listen, Read

Watch: Schitt’s Creek – Again, I’m late to this. Not sure why I overlooked it for so long given the amazing ensemble cast. If you’ve not seen this comedy series about a down-on-their-luck wealthy family trying to make it in the “real world,” you’re missing out. There are 6 seasons, and I am binging all of them.

Listen: Little Simz – British rapper with smart lyrics backed up by smooth beats that she plays bass on. What more could you want?

Read: The Moon Is a Harsh Mistress by Robert A. Heinlein – A sci-fi classic that was just added to my book club’s list a week ago. I’ve not started it, but it looks amazing. Can’t wait. Anyone read it?

What’s new on the blog

Use OKRs to Focus Your Release Strategy Figuring out release strategies for new products and software can feel complicated. So many ideas, so little time. Thankfully, OKRs offer a few key questions that can quickly guide which of the ideas and tasks on your backlog you should prioritize doing now, and which you can save for a later date. Learn which questions to ask in this piece.

OKRs for Transformation Efforts – When companies go through big transformations, what happens with OKRs? Who owns the transformation goals? In brief, the team or high-level executives in charge of overseeing the transformation should set OKRs that directly focus on the goals behind the transformation, and that team or exec needs to own those OKRs. For the less brief version, check out the blog.

Interested in working together? Please reach out. 
In case you need it, here's a description of what I do.


or to participate.