OKRs: What Worked and What Didn't for Our 40+ People Team

CEO & Co-Founder
7 min read

Late in 2021, I was growing increasingly concerned that our team wasn’t rowing in the same direction.

As CEO and captain, my job is to set the vision and chart our course. I felt like I had done a good job of communicating that to the team, and our directors were doing a great job of delivering monthly updates, highlighting their wins, sharing their learnings, and detailing upcoming plans. Day-to-day, things were humming along as well:

  • Customer support was helping our users, triaging issues, and gathering feature requests.
  • Product was debating feature priorities among their group and progressing with a redesign of our web app.
  • Engineering was deep in a refactoring of our reporting feature.
  • Marketing was investing in superb content and helping tell our ​Best Work Life story.

It all felt like progress.

But as I looked deeper across the business, the work wasn’t strategic or coherent, and the metaphorical boat oars were all over the place. In many cases, team members were aware of what another department was doing but not the why. In the worst examples, product would release a feature that marketing couldn't communicate to our customers effectively, and customer support was left wondering why we invested in a specific feature versus the ten other requests we hear every day.

We introduced OKRs to track progress more transparently and unify our growing team

It’s often said that when you reach 30 team members, the systems that got you there no longer work. Departments begin to silo, and communication breaks down between them; new team members are added, which leads to existing members losing clarity in their roles. I’m fascinated by ​​Dunbar’s number and the impact of group size on the relationships between them. We were 27 people at this stage and adding a few people each month.

While nothing felt broken, I had a growing sense of unease that the cracks were forming. So I went in search of systems and processes that would create better alignment across our growing team.

If you stick around long enough in business, OKRs will find you (if you don’t find them first). There’s rarely an organization at scale, particularly in technology, that hasn't experienced them in some form. Invented by the legendary Andy Grove at Intel and made famous by John Doerr, who introduced them to Google, and published the book ​​Measure What Matters, OKRs stand for objectives and key results.

It is a collaborative goal-setting methodology used by teams and individuals to set challenging, ambitious objectives with measurable results. OKRs are how you track progress, create alignment, and encourage engagement around measurable goals.

I read John’s book and went deep into consuming references and podcasts on the topic. I spoke with our leadership team, most of whom had experienced them in their prior orgs, and decided OKRs were worth betting on. I explained my reasoning to the larger group, and we rolled out our first version late in Q4 of 2021.

Glenn introducing OKRs to the Float team.

We decided that we’d have one set of annual OKRs at a company level, which I was accountable for, and a set of quarterly OKRs at a department level, led by each director. We’d assess the objectives and their success each quarter and adjust the OKRs for the next quarter. We also agreed that individuals would not have OKRs, nor would we tie their performance to these OKRs.

Each month, I reported on progress against the annual OKRs, and each quarter, the directors commented on the departmental OKRs and shared those for the upcoming quarter. After four quarters, we shared our experience on what worked and what didn’t. By this stage we were 47 people, and had grown our team by 75%!

What worked for our team

1. OKRs force you to identify your objectives

This sounds like a simple question to answer, right? Wrong! We found that simply asking the question, “What are our objectives?” led to long pauses and many more questions than answers. It revealed that often, we weren’t clear or aligned, which led to a healthy debate on why. The quarterly deadline guaranteed we’d arrive at an answer.

2. OKRs force you to measure better

Results require measures, and we realized (particularly within product and engineering) we didn’t have a lot of good measures in place. What does success look like for a new feature release? What score defines a performance improvement in reporting? OKRs forced us to improve our methods and services to measure progress.

3. OKRs help publicize the why before the what

Any team member could view any department’s OKRs at any point. In doing so, they gained insight into the department’s focus and objectives. So when a new feature was launched or an operations benefit was published, team members were far more prepared, with greater insight into the why behind the work and more buy-in on the solution.

What didn’t work for our team

1. Introducing OKRs is a process of learning and measuring, and we didn’t allow time for both

Each quarter our team leads were simultaneously distilling if the prior quarter’s OKR was successful and if the measures they put in place were appropriate.

Leads would then present these findings and use the information to align their team’s OKRs for the next quarter. The result? Many of our Q4 OKRs weren’t being finalized until late September! It led to a lot of post-rationalization and re-stating of work we’d already planned to do.

When introducing a new process, you must allow time to execute it effectively and improve it. We simply didn't allow time for both.

2. Departmental OKRs stifle cross-departmental collaboration

Creating OKRs at a department level resulted in a natural tendency to look inward within the department to seek alignment. Rarely did teams look sideways to explore complementary objectives or learn from others.

This resulted in a set of OKRs that often felt disjointed and unbalanced.

3. We spent a lot of time debating the OKR process instead of the work

"That’s not a proper objective" was a common refrain as drafts were shared for feedback. "That’s not a measurable result," the corresponding refrain. These questions, while helpful in striving toward a stricter, better version of OKRs, didn’t contribute to adding any value for our customers. Increasingly, we were spending too much time debating the OKR process itself rather than focusing on the work that mattered.

4. Arbitrary OKR timings didn’t allow us to respond quickly to new information

Another example was key results in the operations department related to quarterly headcount growth. OKRs provided the team with a goal; however, as the market conditions for hiring changed in 2022, the quarterly process wasn’t dynamic enough to adjust to it—it felt too rigid and, therefore, outdated.

In a growing team and dynamic industry, we need our goal-setting to be adjustable in real time. That requires a framework that provides the flexibility to adapt to environmental changes and new information, allows us to focus our actions, and enables us to respond rapidly.

Introducing team principles for success

With these learnings in mind, I wondered how we could take the best parts of OKRs and make it work for us? How could we land on a simple and effective process, that would allow us to move fast and support our scaling team?

Around this time, I picked up ​​Principles off my bookshelf. It’s one of my all-time favorite reads on life and work by the legendary Ray Dalio. It made me think—could a set of principles help guide our decision-making?

A peek at Glenn's bookshelf at home.

Toward the end of 2022, I shared a proposal with leadership for the path forward: Let’s replace our OKR process with an alternate approach called Principles for Success.

These are the fundamental truths we agree on as a business that, if followed, will allow us to move closer to executing our mission. Like principles in life, they’re evergreen. They evolve as new information becomes available and can be updated in real time instead of arbitrarily.

Success for Float means producing more happy customers as a result of:

  • A motivated, world-class team
  • Creating awesome human experiences
  • Engaging more professional teams to try Float
  • Generating more team members using Float regularly
  • Supporting teams' ability to schedule more people in Float

We agreed that measuring progress was a practical outcome from OKRs, so we assigned a north star metric for each principle (that we could also track in real time). We designed an internal dashboard featuring each principle’s north star measure in a single view. And while we decided that it was important to have a department lead accountable for each, principles would deliberately not be department owned, as success requires we work collaboratively.

We shared the news with the broader team in the final weeks of 2022, and the announcement was met with both excitement and perhaps a bit of relief—no more scrambling to develop quarterly OKRs! The real-time dashboard also meant team members could immediately dig into the data and pique their curiosity, as it was no longer behind a curtain revealed every quarter.

The Float Principles for Success.

Like OKRs, our Principles for Success are an ongoing experiment.

However, I’m confident that if we follow these principles and align in our mission, we’ll create more happy customers and have a healthy, sustainable business for a long time to come.

Are you curious about trying OKRs on your team? Here are a few resources I found helpful:

Have any questions about Principles for Success? Shoot me an email at glenn@float.com or connect with me on LinkedIn.

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