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Product Strategy

Unlocking the Power of OKR Retrospectives

26 Sep 20234 mins read
Andrea Saez
Unlocking the Power of OKR Retrospectives
By Andrea Saez

So, you've dipped your toes into the OKR pool. Love them or hate them, OKRs are a great method to set, track, and achieve goals while keeping your team hyper-focused. Setting OKRs is just the beginning, the real magic lies in also having retrospectives. 

Annual performance reviews are so 1999. Businesses today need agility. Quarterly OKR retrospectives offer the frequent touchpoints that modern businesses need to continuously change, learn, and adapt. These periodic checkpoints allow teams to assess performance and recalibrate strategies without having to wait an entire year. It’s like updating your computer’s operating system; you wouldn't wait a year for important updates, would you? (I half joke, I know way too many people that keep ignoring theirs. UPDATE THEM NOW!) Quarterly cycles offer you the tools to make changes in real-time, based on real data.

What’s in a retrospective?

Before you dive into your retrospective, make sure everyone knows what's on the agenda. An OKR retrospective essentially breaks down into three components: Celebrating, Observing, and Improving. Each deserves its share of the spotlight. You’re looking at at least 2 hours for a workshop, so be sure to allocate enough time and provide a space for people to actively engage and stay focused.

As you start your retrospective, start with evaluating the objectives themselves. 

  • Did they encapsulate the team's goals? 

  • Next, focus on execution: Did we meet our key results? 

  • Did we aim too high or sell ourselves short? 

All these questions serve to make your future OKRs smarter, sharper, and more aligned with your goals. They are your North Star, guiding you toward an effective strategy for the coming quarter.

startup meeting

Learning from wins and losses

A scoreboard is a tracking tool that captures your OKRs' performance metrics. Think of it as your go-to dashboard for everything OKR-related. It quantifies your objectives and key results, allowing you to clearly see where you stand against your goals. Updated frequently, it serves as a tangible measure of your success—or areas for improvement.

How to Use the Scoreboard

  1. Metrics: Prioritize metrics that are tightly linked to your OKRs.

  2. Visibility: Make the scoreboard accessible to everyone involved in the OKRs to encourage a culture of transparency.

  3. Updates: Keep it updated. An outdated scoreboard defeats the purpose.

  4. Review: Set aside time during team meetings to go over the scoreboard. This ensures everyone knows their status and can discuss challenges and strategies in real time.

In reality, this should be kept up to date by tracking KPIs and the actual progress you’re making. This is how you effectively use OKRs, but based on experience, I know how easy it is to get stuck in firefighting mode and get distracted, causing you to potentially drop the continuous tracking.

It’s ok, it happens. 

What’s truly important here is to sit down at the end of the quarter and review the numbers you do have available (of course, not to say “I told you so”, but if you were keeping track of these things continuously you wouldn’t have to crunch all the numbers at the end of the quarter, now would you?) Let this also be a lesson in keeping organized.

Back to the scorecard...

A win definitely deserves a victory lap. Sure, celebrate and enjoy the win—but don’t just stop there. Analyze what specifically made it a success. Was it the strategy, execution, or perhaps a mix of both? Take those learnings and apply them to future initiatives.

Now, onto the losses. In the world of OKRs, losses aren't your enemy; they're cheat codes for your next level. Losses indicate areas requiring attention and adjustment. Rather than attributing blame, focus on what can be learned. Was the objective too ambitious? Did bottlenecks hinder progress? This is setting the groundwork for growth, so embrace any potential issues you may have encountered.

If you find that your key results are consistently unmet, maybe it's time to rethink their scale, or perhaps revisit the metrics you're using. Establish a results-driven weekly cadence to keep everyone aligned. Keep an eye out for bottlenecks or misalignments. Nip them in the bud, or they’ll turn into major roadblocks down the line. Communication should be open, transparent, and frequent. Because let’s be real, nobody ever complained that their team communicated too well.

team aligned

Benefits of conducting regular OKR retrospectives for product teams

For product teams, OKR retrospectives can be a goldmine. Here’s why:

  1. Agility: Rapid iterations and learning cycles are in the DNA of any successful product team. OKR retrospectives make this agility actionable.

  2. Alignment: When everyone knows the broader objectives, individual contributions feel more impactful. This boosts morale and drives engagement.

  3. Data-informed: You move from gut feeling to data-informed decision-making

  4. Resource optimization: One of the key benefits is knowing where to allocate resources for maximum impact. Do you have a feature that's lagging? Maybe it's time to pivot or allocate more engineering hours to it.

Tips for overcoming challenges during OKR retrospectives

Overcoming challenges during OKR retrospectives requires strategic thinking and a proactive mindset. For starters, you might encounter emotional resistance, especially if OKRs aren't met. It's understandable that the team might be demoralized. While it's crucial to acknowledge these emotions, the key is to pivot the conversation toward what can be learned and improved. 

Then there’s the issue of data gaps. Incomplete or missing data can derail your retrospective's effectiveness. To counter this, identify these gaps early on and develop a plan to fill them, whether that means better tracking mechanisms or revisiting what metrics you're focusing on. 

Finally, don’t underestimate the time commitment needed for a successful retrospective. Rushing through the agenda will compromise the depth of your discussions and the quality of your action items. Ensure that you allocate sufficient time to make the session as effective as it can be (everyone might have opinions as to what happened, but remind the room this isn’t a blame game!)



Integrating OKR retrospectives into your product development lifecycle is like adding a supercharger to your engine. Don’t add resistance to the process by thinking this is just “another meeting”. The insights you gain can directly influence your product roadmap, prioritization, and sprint planning. It goes both ways; your development process can also benefit from a regular review mechanism, becoming more agile and aligned with business goals.


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Andrea Saez

Andrea Saez

PM and PMM leader
Andrea is passionate about product management, growth strategies and community engagement. From writing to hosting talks and events, she loves having the opportunity to learn, talk, and engage with customers and apply product-thinking to scaling companies....more
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