Why Should You Make ‘Retrospection’ a Regular Practice at Work?


Are you tired of feeling like your team members are heading in different directions? Frustrated by the constant struggle to boost productivity and enhance communication?

Or perhaps you’ve noticed that your employees have skill and training gaps that are holding them back.

Many teams face these challenges daily. But here’s the good news: a simple yet effective solution to these problems exists. It’s called “retrospection.”

By combining retrospectives with the simplicity and team-aligning quality of the OKR framework, you can bring your team together, supercharge productivity, and bridge those skill gaps.

We bet you will want to read this one. Let’s explore!

Team having retrospective meeting

Understand ‘Retrospection’ at work with an example

In the busy business world, day-to-day urgency often overshadows the power of reflection. 

Yet, this retrospection can unlock a world of possibilities and improvements in the workplace. So, what exactly is a meaningful retrospection at work?

Let’s see a realistic example of how retrospection works. Imagine an IT project manager overseeing a complex software development project.

They’ve just wrapped up this project, but there were bumps along the way – deadlines were missed, messages got mixed up, and some team members felt exhausted.

In a systematic retrospective, the project manager gathers their team to dissect the project’s lifecycle and milestones. 

They have an open discussion and examine what worked well and what could have been executed more smoothly.

They pinpoint the exact moments where miscommunication led to delays and identify areas where team members’ skills could be better utilized.

Armed with this knowledge, the project manager and their team can make specific adjustments, implement better communication practices, and strategically allocate resources in the next project.

This is one kind of retrospection in action, transforming mistakes into lessons for progress.

Why take the trouble of having retrospective discussions and reflections?

Retrospective discussions and reflections may seem like an additional task on an already crowded to-do list, but their benefits are well worth the effort.

Let’s break it down by the three key stakeholders in an organization: top-level leaders, team managers, and employees

1. For Top-Level leaders

Strategic course correction: Without retrospection, you may remain unaware of the strategy misalignments until it’s too late. By revisiting past decisions and actions, you can make informed course corrections and ensure that the company is always heading in the right direction.

Fostering innovation: By learning from what has worked and what hasn’t, you can promote a culture of creative problem-solving and fresh ideas within the organization.

Employee engagement: By retrospecting, you can identify the factors that impact employee morale and engagement. By addressing these issues proactively, you can create a workplace where employees feel valued and motivated to perform at their best.

2. For Team Managers

Improved team dynamics: By reflecting on past projects and team interactions, you can find solutions to enhance communication, resolve conflicts, and foster a more harmonious team environment.

Efficient workflow: By analyzing the steps taken in past projects, you can identify bottlenecks and improvement areas, leading to more efficient operations and increased productivity.

Individual growth and development: By discussing successes and improvement areas with your team members, you can tailor development plans, ensuring each member reaches their full potential.

3. For employees

Personal Development: Reflecting on your work allows you to pinpoint strengths and weaknesses, enabling continuous growth and progress in your roles.

Enhanced Communication: By sharing your perspectives and experiences, you can contribute to improved team dynamics and a more transparent work environment.

Recognition and Feedback: You can use retrospectives to celebrate achievements and request regular constructive feedback. This practice can ensure that your contributions are acknowledged and that you receive the guidance needed to excel in your roles.

Types of ‘Retrospection’ you can do at work

There are many types of retrospections you can frequently do at work. Maybe you already do some of these as part of your normal operations and business:

  • Self-Assessments: Individuals reflect on their performance, skills, and organizational contributions.
  • Team retrospection: Team members collectively reflect on their collaborative processes, performance, and dynamics.
  • Project Retrospectives: They are focused on reviewing the outcome and processes of a specific project or task.
  • Customer Feedback Analysis: Organizations often introspect by gathering and analyzing customer feedback, such as surveys or reviews.
  • Skills Gap Analysis: This involves identifying employee skills and competencies gaps.

The framework we suggest in this article will help you do any of these retrospectives more objectively and effectively with proper numbers and easy-to-understand reports.

How to make ‘Retrospection’ part of your company culture?

Do you do any kind of retrospection now in your company?

Does it happen in yearly performance reviews? Or do you believe in more frequent retrospection? 

Do these retrospections happen organization-wide?

Do you have any structured practice that most of your team members follow?

Most organizations don’t have a well-designed system for this. 

The majority of HR leaders (87%) surveyed were contemplating changes to performance reviews in 2020.

If you do not do proper retrospection with your team members and want to establish this practice in your team members’ jobs, then we have a simple framework for you.

What if we told you that you can bring retrospection into your work culture without feeling it like another task in your work life?

Now, you have to approach this ‘Retrospection’ initiative in a major way. One that transforms the way you set goals, plan for these goals and execute them.

You will find out – ‘How setting and managing OKRs can help you conduct effective retrospectives at work’

1. Setting the context and goals

The OKR framework starts by setting clear and compelling Objectives, essentially your organization’s top priorities for a specific period, typically a quarter.

These Objectives act as your North Star, illuminating your organization’s path to success. They provide a high-level, strategic focus that ties everyone together under a common goal.

For example, a software development company might set an Objective like “Improve the user experience of our product.” This Objective serves as a beacon of focus for the entire organization. It’s a statement that says, “This is what matters most right now.”

Once you’ve set your Objectives, the magic of OKRs lies in the Key Results. Key Results are the specific, actionable, measurable outcomes that are the stepping stones to their Objective.

To continue with our example, under the Objective of improving user experience, the Key Results could include metrics like “Increase app downloads by 20%,” “Reduce customer support tickets by 15%,” and “Achieve a user satisfaction score of 90%.” These Key Results become the milestones that guide the day-to-day work of team members.

One of the most powerful aspects of the OKR framework is the transparency it fosters. It’s not just the leadership who knows the direction; it’s every team member.

In this context, the retrospection process becomes more meaningful and actionable. This clarity empowers retrospectives at all levels, ensuring they are purposeful, aligned, and effective in driving the organization forward.

2. The evidence (data) for your retrospective

In any effective retrospection, data is key. You need tangible evidence to assess your progress, make informed decisions, and drive meaningful improvements.

What data can okrs give you for your retrospectives

Progress tracking: With a real-time snapshot of your progress toward each Key Result, you can easily gauge whether you’re on track to achieve your goals or if there’s a need for course correction.

Outcome assessment: At the end of the quarter or project, you can objectively measure whether you’ve achieved your Key Results. This provides concrete evidence of what was accomplished and what fell short, making it the perfect starting point for a retrospective.

Historical performance: Over time, you get a historical record of your organization’s Objectives and Key Results. This record becomes a treasure trove for long-term retrospectives, allowing you to spot trends, track your organizational growth, and identify areas of consistent success or challenge.

This real-time availability means that your retrospectives can be conducted with the freshest data, allowing you to act swiftly to address any issues or capitalize on successes.

This data is available in real-t ime and is transparent and fair for all

Furthermore, the transparency of OKRs ensures that everyone in the organization has access to the same data. This levels the playing field and promotes fairness.

In retrospectives, it means that discussions are based on objective, shared information rather than subjective opinions or interpretations.

You can easily do self-assessment anytime

Since your Key Results are clear, measurable targets, you can easily assess your own progress at any time.

For example, if you’re working on a project and notice that one of your Key Results is off track, you can immediately reflect on what went wrong and make adjustments.

This ability to self-assess in real-time empowers individuals to take control of their work and growth, making retrospections a dynamic and ongoing practice rather than an occasional event.

3. Weekly OKR check-ins and retrospectives

building skills and helping people deliver

How are your OKRs coming along? Are there any blockers that could stop you from achieving your objectives?

You see the progress on a OKR software dashboard or a spreadsheet and ask Are there any obstacles that might hinder you from accomplishing your objectives?

In this step, we explore how weekly OKR check-ins and retrospectives can turn retrospectives into a dynamic process of learning, growth, and collaboration.

It is all about ‘action to get it back on track’

This regular cadence ensures that teams and individuals stay on top of their progress, identify any roadblocks, and take immediate action to keep their Key Results on track.

These check-ins are, in essence, mini-retrospectives, occurring weekly.

During these weekly retrospectives, the focus is not solely on what has been achieved or missed. Instead, the spotlight is on “what action can be taken to get it back on track.”

It’s a forward-looking, problem-solving approach. If a Key Result is lagging, the team discusses the reasons behind it and collaboratively brainstorms solutions.

Building skills and helping people deliver on their OKRs

Team members are encouraged to reflect on their performance and consider how to enhance their skills to effectively meet their Key Results.

Team members can share their experiences, challenges, and discoveries, creating a rich learning environment.

This process not only helps in achieving current OKRs but also equips individuals with new skills that they can apply to future goals and tasks.

You ask the teammates without any judgment in a candid conversation

These conversations are candid and open, free from blame or finger-pointing. Teammates are encouraged to speak honestly about their progress, challenges, and any support they may need.

This non-judgmental atmosphere promotes trust and psychological safety within the team. It encourages individuals to be more forthcoming about their struggles and, in turn, makes it easier for the team to offer help and support where it’s needed.

These OKR check-ins transform the introspective process from a static evaluation into a dynamic cycle of action, skill-building, and mutual support.

4. Quarterly retrospection and grading

This phase is crucial, as it not only wraps up the current OKR cycle but also provides invaluable insights for crafting new OKRs in the next cycle.

Let’s explore how this step refines your introspection process and helps you improve continuously.

The Purpose – To provide insights to craft new OKRs for the next OKR cycle

At the end of each quarter, it’s time to step back and evaluate your progress. You extract insights that will inform the creation of new, effective OKRs for the next cycle.

It’s your opportunity to learn from your achievements and challenges, ensuring that your future goals are well-informed and realistic.

It’s pass or fail only with the Key Results

The team or individual evaluates whether a specific goal (Objective) has been met.

In the world of Key Results (KRs), it’s binary grading. You either achieve the KR or not.

After quickly grading OKRs, it’s time to reflect and ask questions

It’s time to reflect on the journey and ask essential questions:

  • What added to our success? Start by identifying what went right. What actions, strategies, or collaborations contributed to achieving the OKRs? Recognizing these factors is crucial for replicating success in the future.
  • If we didn’t accomplish it, what barriers did we encounter? Whether it’s resource limitations, unexpected challenges, or missed opportunities, understanding what held you back helps you devise strategies to overcome similar hurdles in the future.
  • If we were to rewrite the goal, what would we change? By considering how you might rewrite the Objective or adjust the Key Results, you’re setting the stage for more relevant, achievable OKRs in the next cycle.

By asking these critical questions, you gain the insights needed to continually improve, adapt, and set more effective OKRs for the future.

This introspection loop is what propels your organization forward with purpose and precision.

5. Execution and focus on leading metrics, innovation, and improvement

The process doesn’t end with simply defining goals and measuring outcomes. It extends to executing those goals and the metrics you use to track progress.

This step is where retrospection becomes a powerful business growth and innovation tool.

Leading metrics are indicators that provide early insights into the likelihood of achieving your OKRs. They serve as proactive signals that help you make course corrections before it’s too late.

Instead of waiting for results, you’re constantly scanning for early indicators and adjusting your strategies accordingly. This proactive approach fosters innovation. 

For example, if your Objective is to increase customer retention, a lagging metric might be the number of customers retained at the end of the quarter.

However, a leading metric could be the number of customer interactions or the engagement rate, which can indicate the health of customer relationships well before the end of the quarter.

In conclusion, the execution of OKRs with a focus on leading metrics amplifies the impact of retrospectives on your business.

It encourages innovation, keeps your organization agile, and maintains a laser focus on improvement.

This constant pursuit of strategic reflection, planning, and execution sets successful organizations apart and makes retrospection a driving force for growth and innovation.


In the ever-evolving landscape of modern business, where you cannot survive without adaptability and continuous improvement, the OKR framework simplifies goal-setting and the meaningful execution of these goals throughout the organization.

More than that, it doesn’t just relegate retrospectives to a yearly or bi-yearly formal process but weaves it into the very fabric of everyday work life, making it a dynamic, forward-looking, and innovative process.

With OKRs, introspection is no longer just about assessing achievements or failures; it’s about harnessing insights to foster innovation, address challenges, and drive improvement.

author img

Gaurav Sabharwal


Gaurav is the CEO of JOP (Joy of Performing), an OKR and high-performance enabling platform. With almost two decades of experience in building businesses, he knows what it takes to enable high performance within a team and engage them in the business. He supports organizations globally by becoming their growth partner and helping them build high-performing teams by tackling issues like lack of focus, unclear goals, unaligned teams, lack of funding, no continuous improvement framework, etc. He is a Certified OKR Coach and loves to share helpful resources and address common organizational challenges to help drive team performance. Read More

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