Insider’s OKR Journey: How We Sidestepped 4 Common Mistakes

Ege Dinc
Insider Engineering
8 min readMar 28, 2023

Setting clear goals and tracking progress is essential for success in any organization. However, without a structured approach to goal setting and measurement, it can be difficult to achieve the desired outcomes. This is where Objectives and Key Results (OKRs) come in. First developed by Intel’s CEO Andy Grove in the 1970s, OKRs are a methodology for setting and tracking goals that have become increasingly popular in recent years.

At their core, OKRs consist of two main components: Objectives and Key Results. Objectives are generally qualitative statements that describe the desired outcome or direction of the organization. Key Results, on the other hand, are measurable targets that help to gauge progress towards achieving the objectives, and they represent headway for the objective they serve. Together, these two components provide a framework for aligning individual and team goals with the organization’s overall objectives, while also providing a clear sense of direction and purpose.

To give an example from our department, when our Objective is:

  • Our products will be ready to conquer the markets we are in.

A few effective Key Results are:

  • All products will have NPS > X on average this quarter.
  • Insider’s effect on selected partners' page speed to be decreased by X%.
  • Reducing Bug Score by X%. (Bug Score ≅ Bug Impact)

Note that all key results are well-defined, measurable, and relevant to the objective. Successfully completing one of these KRs ensures that the company is one step closer to achieving its objective.

There is a myriad of online resources about the effective use of OKRs. Despite their effectiveness, implementing OKRs can be a challenge. In this blog post, I intend to share some of the most common OKR mistakes we experienced and offer guidance on how to avoid them. Though they may seem simple, getting the basics right is a precondition for realizing goals in a sustainable way. I hope that this post will help others facing similar issues to successfully apply OKRs in their organizations. In the following sections, I will go over common pitfalls, and how we handled them as Insider’s Product and Development department.

If you are interested in more technical topics, feel free to check out Insider’s Engineering Blog.

1. Setting Too Vague Key Results

Vague key results can be difficult to measure and can lead to confusion around what success looks like, it can lead to a lack of clarity around what needs to be achieved, making it challenging for teams to understand what they need to do and how they will know when they have succeeded. This can result in a lack of focus and direction, making it difficult for teams to prioritize their work and make progress toward meaningful goals.

Make sure that your key results are specific, measurable, achievable, relevant, and time-bound (SMART). Each key result should clearly state what needs to be achieved, how it will be measured, and when it will be achieved. This provides a clear roadmap for success and enables teams to track progress and make necessary adjustments along the way.

To specific key results, organizations can use metrics and quantifiable data to set clear targets. The targets should be challenging but achievable to ensure that they provide motivation and a sense of accomplishment when they are met. Additionally, it is important to confirm that the key results are relevant to the overall objectives of the organization.

At Insider, we made certain that our key results were specific and measurable by creating well-defined success criteria at the beginning of each quarter. These success criteria (KR Grading) included a few weighted and measurable targets that were tied to each key result. This approach allowed us to accurately measure the success of each key result at the end of the quarter and helped our OKR program remain effective and meaningful.

To illustrate, here are two key results. One of them is from our early days using OKRs, and the other is recent. Which one do you think is easier to measure when the quarter ends?

1. Preparing for a Cookieless world by coming up with alternative solutions through research.

2. Completing smooth integrations (smoothness confirmed by both partner and CSM): 5 with Shopify, 3 with Magento, and launching 10 new integrations.

KR Grading (100% in total):

  • 5 Shopify Integrations (30% weight)
  • 3 Magento Integrations (30% weight)
  • Launching 10 new integrations (40% weight)

2. Setting Too Many Objectives or Key Results

Setting too many objectives is a common mistake when implementing the OKR methodology. While it may seem like having a long list of objectives is good, it can be counterproductive. Having too many objectives can lead to a lack of focus and resources being spread too thin, leading to insufficient progress on most of the objectives. It is safe to say that having 6 objectives and 30 key results is too much of a stretch and definitely does not help with focus or alignment either!

To identify the most important objectives, start by considering the company’s overall strategy and vision. What are the key priorities for the organization, and which objectives are most aligned with those priorities? It’s also important to consider the resources available to the team and the level of effort required to achieve each objective.

Once the most important objectives have been identified, it’s time to narrow down the list of key results (KRs) associated with each objective. It’s important to ensure that each KR is relevant and contributes to the objective it serves. One tip for narrowing down the list of KRs is to focus on the most important metrics that will have the greatest impact on achieving the objective. Another tip is to collaborate with team members to identify which KRs are most critical and which ones can be deprioritized or eliminated altogether.

Although it depends on the size and structure of the teams, it is recommended to set at most 5 objectives with maximum 5 KRs each, though it is perfectly normal to have 1–2 objectives with a few key results. Once we brought our number of OKRs from 6x5 (6 objectives with 5 KRs each) down to 4x4 (and 3x4 in the following year), we finally found our sweet spot and saw a substantial increase in the success of our key results.

Before:

6 Objectives, 27 KRs, 47% Success Rate

After:

4 Objectives, 16 KRs, 73% Success Rate

3. Not Determining KR Owners (Directly Responsible Individuals)

One common mistake that organizations make when implementing OKRs is not assigning a KR owner. A KR owner is the individual or team responsible for the success of a specific key result. The lack of clarity and direction is one of the main problems with not assigning a KR owner. If no one is explicitly responsible for a specific KR, it can be unclear who is accountable for its success. This can lead to a lack of direction and motivation, as team members may not know who to turn to for guidance, support, and alignment.

Additionally, neglect or forgetting to track a KR can occur if there is no KR owner. Without a designated person responsible for ensuring that the KR is being monitored and progressed, the KR can easily be neglected, leading to a lack of progress toward its objective.

To determine a KR owner, organizations can identify the individual or team with the most relevant expertise and resources. It is important to clarify the roles and responsibilities of the KR owner and assign them during the planning phase. By doing so, everyone is clear about who is responsible for each KR, ensuring accountability and progress tracking throughout the quarter.

At Insider, we successfully avoided this mistake by assigning a KR owner for each key result as early as possible. This not only helped us to accurately track progress and make necessary adjustments throughout the quarter but also sped up the KR writing process. By having a designated KR owner, we have been able to ensure that each KR has clear ownership, accountability, and progress tracking.

4. Lack of Regular Check-ins

One of the most common mistakes when implementing the OKR methodology is the lack of regular check-ins. When teams fail to schedule and attend regular meetings to track progress toward their objectives, it becomes difficult to have a clear understanding of how well they are doing and identify potential roadblocks. This lack of visibility can lead to missed opportunities to make adjustments and keep objectives on track.

To avoid this mistake, it is essential to establish a regular cadence for check-ins, which can be weekly, bi-weekly, or monthly, depending on the organization’s needs. This allows teams to stay up-to-date on their progress and identify any issues early on, providing them with the opportunity to address them before they become bigger problems.

To make the most out of these check-ins, it is also essential to ensure everyone is prepared beforehand. This allows teams to focus on the discussion at hand and come up with solutions to any obstacles or challenges they may be facing. By doing so, they can celebrate wins and acknowledge progress, which can help keep the team motivated and engaged.

At Insider, we have witnessed the importance of regular check-ins firsthand. We run bi-weekly OKR check-in meetings, where we come together to share progress, discuss any issues, and collaborate on solutions. This has helped us to stay on track with our objectives, and it has also provided a platform for open communication and feedback between team members and managers.

Besides regular meetings, it is also crucial for transparency to create a process for tracking progress and updating OKRs. Teams should have access to a shared system where they can easily monitor and update their OKRs, whether it is a single spreadsheet or a dedicated platform. This ensures that everyone is on the same page and has visibility into each other’s progress.

Wrapping up, the increasingly popular OKR methodology provides a structured approach to goal setting and measurement, allowing organizations to align individual and team goals with the organization’s overall objectives while providing a clear sense of direction and purpose. However, certain pitfalls may hinder the potential of this framework, such as setting vague key results, setting too many objectives or key results, and not determining KR grading as we discussed above. To overcome these pitfalls, organizations should ensure their key results are SMART, identify the most important objectives based on the company’s overall strategy and vision, narrow down the list of key results by focusing on the most important metrics, and decide on a grading system early on to accurately measure the success of each key result. By following these guidelines, we managed to boost our quarterly OKR success rate by more than 30%. I encourage you to apply these firsthand OKR tips in your organization, hoping they benefit your program as they did ours, and move you one step closer to achieving your desired outcomes.

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