A Work in Progress: Our Team’s Journey with Goal Setting and OKRs

A few weeks ago, I published Goals Gone Wrong: Is Conventional Wisdom Sabotaging Your Success? In it, I explored how well-intentioned goals can sometimes backfire. I shared how goals, when misapplied, can lead to overly narrow focus, misaligned priorities, and even undermine overall performance. When I read Measure What Matters by John Doerr , I was curious: could OKRs offer a way to set goals that are both ambitious and healthy?

What Are OKRs (and Why Do They Matter)?

John Doerr popularized Objectives and Key Results (OKRs) after learning the framework at Intel Corporation from Andy Grove. The concept is simple:

• Objectives are what you want to accomplish. They should be inspirational and time-bound.
• Key Results are how you'll measure progress. They should be specific and, ideally, quantifiable.

OKRs aim to solve a common leadership challenge: setting direction without micromanaging the path. John outlines the "Four Superpowers" of OKRs. These four principles help explain why OKRs work when applied effectively:

1. Focus and Commit to Priorities: OKRs force you to choose what matters most. Instead of chasing every idea, you commit to a few that will make the biggest difference.
2. Align and Connect for Teamwork: OKRs create visibility. When teams understand each other’s objectives, collaboration improves, silos break down, and people pull in the same direction.
3. Track for Accountability: What gets measured gets managed. OKRs provide a structure for tracking progress transparently and adjusting as needed.
4. Stretch for Amazing: Great OKRs encourage ambition. They push teams beyond business-as-usual thinking, inviting bold goals that fuel innovation and growth.

OKRs in the Wild: What We Learned

Last year, Joseph Reckamp and I worked together to implement OKRs for our team. As part of my reflection on that experience, I sat down with Joe to revisit how the process unfolded. What follows are a few questions I asked him about our journey: what we learned, what we got right, and where we still have room to grow.

1. What resources did you use to learn about OKRs?

Joe kicked off the process by reading Measure What Matters. It helped him understand not just how to structure OKRs, but why they matter, especially when it comes to focus and transparency.

“This was probably the best resource to understand the why behind OKRs and what made them so popular.”

Rupesh's Thoughts: I read Measure What Matters and found it to be an engaging collection of stories that really shows the impact OKRs can have. That said, when it came time to actually implement them, I found WhatMatters.com more helpful. The short, two-hour course was practical and walked me through the nuts and bolts of building OKRs with a team. Everyone learns differently; for me, the website offered the clarity I needed to get started.

2. How did you set your first OKRs? What did that process look like?

Joe focused our team's initial OKRs on three core areas: financial performance, habit formation, and organizational change. He was intentional about not overloading our teams with too many goals. The primary objective is to drive revenue, so he set targets around quarterly new logo acquisition and annual recurring revenue from expansion.

Next, he wanted to instill a new habit. In a fast-paced scale-up environment, change is constant. To maintain focus, he decided to work on building one habit at a time (more on focus shortly).

Finally, he identified a broader organizational change he wanted to support and set a goal to help drive that transformation.  

We held a collaborative brainstorming session with other leaders, followed by team-wide socialization before finalizing the goals.

Rupesh's Thoughts: Collaborating with the leadership team gave me a deeper understanding of how our global organization operates. We took the time to incorporate input from teams across regions. This made our OKRs more relevant, more inclusive, and ultimately more effective, reducing the need to create separate, region-specific goals.

I appreciated Joe’s decision to structure our OKRs around financial performance, habit formation, and organizational change. This made it easier to communicate to our teams: what we were doing, why it mattered, and how it all connected. It also helped us as a leadership team stay focused on what was truly important, rather than getting lost in the weeds.

3. How did it go? What worked well?

When I asked Joe how it went, one benefit stood out right away: clarity.

“There were a lot of competing priorities. In any rapidly growing organization, new requests and shifting priorities often come from all directions, making it challenging to identify and focus on what truly matters most. OKRs gave us a way to filter those requests, align our teams, and even influence upward.”

This aligns beautifully with Doerr’s view: OKRs aren't just about marching orders. They're a tool for conversation, negotiation, and empowerment.

Rupesh's Thoughts: Something I really appreciated about our approach was setting OKRs on a quarterly cadence. When I worked in oil and gas, a slower-moving beast compared to SaaS software, we used to set annual goals. I remember thinking as a young engineer that my goals would be outdated in two months (and they often were). A quarterly cadence provides more relevant feedback and gives teams the flexibility to adapt. Even in oil and gas, things are always changing. Priorities shift. Earthquakes happen. Financial crises emerge. OKRs let us respond in real time.

4. What lessons did you learn?

As with any new process, there were a few bumps along the way. When I asked Joe about what didn’t go as planned, he pointed to one of the most common OKR pitfalls: vague or unmeasurable key results.

“We didn’t think enough about how we were going to measure them before setting them. One of our goals involved ‘having discovery calls before demos.' But it was almost impossible to track reliably.”

This echoes a warning from Measure What Matters itself: If you can’t measure it, it’s not a key result.

Rupesh's Thoughts: One of my biggest takeaways? In our effort to simplify, we may have overcorrected. We were so focused on not overwhelming the team with too many goals that we didn’t ask individuals to set any of their own. Everyone had a shared team-level OKR, but that was it. On paper, this seemed like a clean and focused approach. In practice, it led to tunnel vision. When team members couldn’t make progress on the team goal, it created discomfort, because they didn’t have alternative individual goals they could point to as evidence of progress.

Looking back, I realize we missed a big opportunity for ownership. When individuals help shape the goals, they’re more likely to connect with them, care about them, and commit to them. Next time, I’d make sure every team member has at least one personal or role-specific goal that ladders up to the bigger picture.

It’s easy to assume that less is more. Alignment doesn’t just come from simplicity—it comes from engagement. And engagement starts with involvement

5. What advice would you give to someone setting OKRs for the first time?

“Don’t expect to get it right the first time. You’re going to have to iterate and improve.”

OKRs are not a one-and-done solution—they’re a practice. And like any good habit, they get better with refinement.

Rupesh's Thoughts: Goal setting is a muscle. It takes repetition, feedback, and patience to build.

Progress Over Perfection

Reflecting on the past year, and through this conversation with Joe, I was reminded just how much learning happens through doing. Our first year implementing OKRs wasn’t perfect, but it was a start. It brought clarity, sparked important conversations, and gave us a framework we could build on. The more we worked with it, the more we realized: goal setting isn’t about getting it “right” the first time. Goal setting is about creating a rhythm of focus, feedback, and refinement. As John Doerr says,

“Ideas are easy. Execution is everything.”

We’re still learning. But that’s the point!